SK8662000A3 - Triazine angiogenesis inhibitors - Google Patents
Triazine angiogenesis inhibitors Download PDFInfo
- Publication number
- SK8662000A3 SK8662000A3 SK866-2000A SK8662000A SK8662000A3 SK 8662000 A3 SK8662000 A3 SK 8662000A3 SK 8662000 A SK8662000 A SK 8662000A SK 8662000 A3 SK8662000 A3 SK 8662000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- triazine
- diamine
- phenyl
- biphenyl
- triazin
- Prior art date
Links
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title description 3
- 239000004037 angiogenesis inhibitor Substances 0.000 title description 3
- 229940121369 angiogenesis inhibitor Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 204
- 238000000034 method Methods 0.000 claims abstract description 75
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229940002612 prodrug Drugs 0.000 claims abstract description 7
- 239000000651 prodrug Substances 0.000 claims abstract description 7
- -1 spiroalkyl Chemical group 0.000 claims description 77
- UBPQITZLYDWRFS-UHFFFAOYSA-N 3,4-dihydro-1H-triazine-2,4-diamine Chemical compound NC1NN(N)NC=C1 UBPQITZLYDWRFS-UHFFFAOYSA-N 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052727 yttrium Inorganic materials 0.000 claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 230000002491 angiogenic effect Effects 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- FFDPAFDJEZFMCD-UHFFFAOYSA-N 6-(3-bicyclo[2.2.1]heptanyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2C3CCC(C3)C2)=N1 FFDPAFDJEZFMCD-UHFFFAOYSA-N 0.000 claims description 5
- GAAPEHOATNFBOJ-UHFFFAOYSA-N 6-(4-phenylnaphthalen-1-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C3=CC=CC=C3C(C=3C=CC=CC=3)=CC=2)=N1 GAAPEHOATNFBOJ-UHFFFAOYSA-N 0.000 claims description 5
- YXJYSVRMWCERIB-HAQNSBGRSA-N Nc1nc(N)nc(n1)[C@H]1CC[C@@H](CC1)c1ccccc1 Chemical compound Nc1nc(N)nc(n1)[C@H]1CC[C@@H](CC1)c1ccccc1 YXJYSVRMWCERIB-HAQNSBGRSA-N 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- WVKMYNCTNPSPKI-UHFFFAOYSA-N n-[4-acetamido-6-(4-phenylphenyl)-1,3,5-triazin-2-yl]acetamide Chemical compound CC(=O)NC1=NC(NC(C)=O)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 WVKMYNCTNPSPKI-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- OEVGRXXNVFAVND-UHFFFAOYSA-N 1-[4-(4,6-diamino-1,3,5-triazin-2-yl)phenyl]-3-phenylurea Chemical compound NC1=NC(N)=NC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 OEVGRXXNVFAVND-UHFFFAOYSA-N 0.000 claims description 4
- ZPGRSTWWAOXITL-UHFFFAOYSA-N 2-n,4-n-dimethyl-6-(4-phenylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound CNC1=NC(NC)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 ZPGRSTWWAOXITL-UHFFFAOYSA-N 0.000 claims description 4
- BPMBNLJJRKCCRT-UHFFFAOYSA-N 4-phenylbenzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=CC=C1 BPMBNLJJRKCCRT-UHFFFAOYSA-N 0.000 claims description 4
- JGLAWBDTRPIJEB-UHFFFAOYSA-N 6-(1-azabicyclo[2.2.2]octan-4-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C23CCN(CC2)CC3)=N1 JGLAWBDTRPIJEB-UHFFFAOYSA-N 0.000 claims description 4
- QXUKDKFCTWKYAQ-UHFFFAOYSA-N 6-(1-benzylpiperidin-4-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2CCN(CC=3C=CC=CC=3)CC2)=N1 QXUKDKFCTWKYAQ-UHFFFAOYSA-N 0.000 claims description 4
- ITIHKNWGVRAVEQ-UHFFFAOYSA-N 6-(1-phenylcyclohexyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2(CCCCC2)C=2C=CC=CC=2)=N1 ITIHKNWGVRAVEQ-UHFFFAOYSA-N 0.000 claims description 4
- YLQTUNLFLWOYEG-UHFFFAOYSA-N 6-(1-phenylpiperidin-4-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2CCN(CC2)C=2C=CC=CC=2)=N1 YLQTUNLFLWOYEG-UHFFFAOYSA-N 0.000 claims description 4
- XJDFXAGIOYZICS-UHFFFAOYSA-N 6-(2,3-dihydro-1,4-benzodioxin-6-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C3OCCOC3=CC=2)=N1 XJDFXAGIOYZICS-UHFFFAOYSA-N 0.000 claims description 4
- QJTMOUNSVMGWQA-UHFFFAOYSA-N 6-(3-pyrrol-1-ylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C(C=CC=2)N2C=CC=C2)=N1 QJTMOUNSVMGWQA-UHFFFAOYSA-N 0.000 claims description 4
- UGHGIHCMBAYXFC-UHFFFAOYSA-N 6-[1-(4-phenylphenyl)piperidin-4-yl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2CCN(CC2)C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 UGHGIHCMBAYXFC-UHFFFAOYSA-N 0.000 claims description 4
- RSPNBRFOPXUYIQ-UHFFFAOYSA-N 6-[4-(2-nitrophenyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(=CC=2)C=2C(=CC=CC=2)[N+]([O-])=O)=N1 RSPNBRFOPXUYIQ-UHFFFAOYSA-N 0.000 claims description 4
- OFAFETHKOUXIOT-UHFFFAOYSA-N 6-[4-(2-phenylethynyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(=CC=2)C#CC=2C=CC=CC=2)=N1 OFAFETHKOUXIOT-UHFFFAOYSA-N 0.000 claims description 4
- ZHRAYTRAZFABSD-UHFFFAOYSA-N 6-isoquinolin-1-yl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C3=CC=CC=C3C=CN=2)=N1 ZHRAYTRAZFABSD-UHFFFAOYSA-N 0.000 claims description 4
- NNTYOEXOTVCMGO-UHFFFAOYSA-N 6-quinolin-2-yl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2N=C3C=CC=CC3=CC=2)=N1 NNTYOEXOTVCMGO-UHFFFAOYSA-N 0.000 claims description 4
- ZLRYWZMZVKFOLI-UHFFFAOYSA-N 6-quinolin-3-yl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C3C=CC=CC3=NC=2)=N1 ZLRYWZMZVKFOLI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- FHMRBIALTGFRNJ-UHFFFAOYSA-N n-[4-acetamido-6-(4-phenoxyphenyl)-1,3,5-triazin-2-yl]acetamide Chemical compound CC(=O)NC1=NC(NC(C)=O)=NC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 FHMRBIALTGFRNJ-UHFFFAOYSA-N 0.000 claims description 4
- KAAUHJIYJFHBRA-UHFFFAOYSA-N n-[4-amino-6-(4-phenoxyphenyl)-1,3,5-triazin-2-yl]acetamide Chemical compound CC(=O)NC1=NC(N)=NC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 KAAUHJIYJFHBRA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- GVMLSTSZZWVGGW-UHFFFAOYSA-N 2-n,4-n-diethyl-6-(4-phenylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound CCNC1=NC(NCC)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 GVMLSTSZZWVGGW-UHFFFAOYSA-N 0.000 claims description 3
- PRLSQDUKCNHPCS-UHFFFAOYSA-N 6-(2,2-dimethylchromen-6-yl)-1,3,5-triazine-2,4-diamine Chemical compound C1=C2C=CC(C)(C)OC2=CC=C1C1=NC(N)=NC(N)=N1 PRLSQDUKCNHPCS-UHFFFAOYSA-N 0.000 claims description 3
- BLMMGZAMOFVULF-UHFFFAOYSA-N 6-(2-phenylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 BLMMGZAMOFVULF-UHFFFAOYSA-N 0.000 claims description 3
- AJYIIQHOGSLLEA-UHFFFAOYSA-N 6-(4-phenoxyphenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 AJYIIQHOGSLLEA-UHFFFAOYSA-N 0.000 claims description 3
- JDZMWANIXJLYCP-UHFFFAOYSA-N 6-(4-phenylsulfanylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(SC=3C=CC=CC=3)=CC=2)=N1 JDZMWANIXJLYCP-UHFFFAOYSA-N 0.000 claims description 3
- GYXOQMHEMGDKMJ-UHFFFAOYSA-N 6-(4-piperidin-1-ylsulfonylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(=CC=2)S(=O)(=O)N2CCCCC2)=N1 GYXOQMHEMGDKMJ-UHFFFAOYSA-N 0.000 claims description 3
- BLEJYLKFVPGPDH-UHFFFAOYSA-N 6-(5-bromopyridin-3-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=C(Br)C=NC=2)=N1 BLEJYLKFVPGPDH-UHFFFAOYSA-N 0.000 claims description 3
- STPVTZHLAUBVDJ-UHFFFAOYSA-N 6-(5-phenylfuran-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2OC(=CC=2)C=2C=CC=CC=2)=N1 STPVTZHLAUBVDJ-UHFFFAOYSA-N 0.000 claims description 3
- JXPHBAMKLSIDNB-UHFFFAOYSA-N 6-(6-methoxy-1,3-benzothiazol-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=NC(N)=NC(N)=N1 JXPHBAMKLSIDNB-UHFFFAOYSA-N 0.000 claims description 3
- OCZVVHYNNZCBCI-UHFFFAOYSA-N 6-(6-methylpyridin-3-yl)-1,3,5-triazine-2,4-diamine Chemical compound C1=NC(C)=CC=C1C1=NC(N)=NC(N)=N1 OCZVVHYNNZCBCI-UHFFFAOYSA-N 0.000 claims description 3
- JUJQABXAYGPDQQ-UHFFFAOYSA-N 6-[1-(4-methoxyphenyl)cyclohexyl]-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(OC)=CC=C1C1(C=2N=C(N)N=C(N)N=2)CCCCC1 JUJQABXAYGPDQQ-UHFFFAOYSA-N 0.000 claims description 3
- IETLEQAPYLPHFH-UHFFFAOYSA-N 6-[1-(4-methoxyphenyl)piperidin-4-yl]-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(OC)=CC=C1N1CCC(C=2N=C(N)N=C(N)N=2)CC1 IETLEQAPYLPHFH-UHFFFAOYSA-N 0.000 claims description 3
- IHYCVHLOPBITOS-UHFFFAOYSA-N 6-[4-(4-azidophenyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)N=[N+]=[N-])=N1 IHYCVHLOPBITOS-UHFFFAOYSA-N 0.000 claims description 3
- ZYGRNMCCKSCGAD-UHFFFAOYSA-N 6-[4-(4-pentylphenyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(CCCCC)=CC=C1C1=CC=C(C=2N=C(N)N=C(N)N=2)C=C1 ZYGRNMCCKSCGAD-UHFFFAOYSA-N 0.000 claims description 3
- OGKRYYZQFSFRKX-UHFFFAOYSA-N 6-[4-(benzenesulfinyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(=CC=2)S(=O)C=2C=CC=CC=2)=N1 OGKRYYZQFSFRKX-UHFFFAOYSA-N 0.000 claims description 3
- YNBGVMFZMGHALH-UHFFFAOYSA-N 6-[4-(benzenesulfonyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)=N1 YNBGVMFZMGHALH-UHFFFAOYSA-N 0.000 claims description 3
- NXKGSRVQERUNNC-UHFFFAOYSA-N 6-[4-[5-(trifluoromethyl)pyridin-2-yl]oxyphenyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(OC=3N=CC(=CC=3)C(F)(F)F)=CC=2)=N1 NXKGSRVQERUNNC-UHFFFAOYSA-N 0.000 claims description 3
- VJNYZFKSPRAFPN-MGCOHNPYSA-N Nc1nc(N)nc(n1)[C@H]1C[C@@H](C1)c1ccccc1 Chemical compound Nc1nc(N)nc(n1)[C@H]1C[C@@H](C1)c1ccccc1 VJNYZFKSPRAFPN-MGCOHNPYSA-N 0.000 claims description 3
- PBAGBOBUENHGGT-UHFFFAOYSA-N [4-(4,6-diamino-1,3,5-triazin-2-yl)piperidin-1-yl]-phenylmethanone Chemical compound NC1=NC(N)=NC(C2CCN(CC2)C(=O)C=2C=CC=CC=2)=N1 PBAGBOBUENHGGT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000004419 alkynylene group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- BIYSZWTXIOWPRR-UHFFFAOYSA-N n-[4-(4,6-diamino-1,3,5-triazin-2-yl)phenyl]benzenesulfonamide Chemical compound NC1=NC(N)=NC(C=2C=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=2)=N1 BIYSZWTXIOWPRR-UHFFFAOYSA-N 0.000 claims description 3
- DYQGHDRTIQOJTH-UHFFFAOYSA-N n-[4-(4,6-diamino-1,3,5-triazin-2-yl)phenyl]naphthalene-1-sulfonamide Chemical compound NC1=NC(N)=NC(C=2C=CC(NS(=O)(=O)C=3C4=CC=CC=C4C=CC=3)=CC=2)=N1 DYQGHDRTIQOJTH-UHFFFAOYSA-N 0.000 claims description 3
- GSCBNLVSYKDLSU-UHFFFAOYSA-N n-[4-acetamido-6-[4-(benzenesulfonyl)phenyl]-1,3,5-triazin-2-yl]acetamide Chemical compound CC(=O)NC1=NC(NC(C)=O)=NC(C=2C=CC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)=N1 GSCBNLVSYKDLSU-UHFFFAOYSA-N 0.000 claims description 3
- VMQQSAVNKJMMFV-UHFFFAOYSA-N n-[4-amino-6-(4-phenylphenyl)-1,3,5-triazin-2-yl]acetamide Chemical compound CC(=O)NC1=NC(N)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 VMQQSAVNKJMMFV-UHFFFAOYSA-N 0.000 claims description 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
- AZMWJIWSYRGLGF-UHFFFAOYSA-N 6-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(N2CCC3(CC2)OCCO3)=N1 AZMWJIWSYRGLGF-UHFFFAOYSA-N 0.000 claims description 2
- FZWISDKYXBCTGO-UHFFFAOYSA-N 6-(2,3-dihydro-1,4-benzodioxin-3-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2OC3=CC=CC=C3OC2)=N1 FZWISDKYXBCTGO-UHFFFAOYSA-N 0.000 claims description 2
- DNIYXWVXIIXAFF-UHFFFAOYSA-N 6-(4-thiophen-2-ylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(=CC=2)C=2SC=CC=2)=N1 DNIYXWVXIIXAFF-UHFFFAOYSA-N 0.000 claims description 2
- ALBGUUBQTYPQEG-UHFFFAOYSA-N 6-(5-phenylthiophen-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2SC(=CC=2)C=2C=CC=CC=2)=N1 ALBGUUBQTYPQEG-UHFFFAOYSA-N 0.000 claims description 2
- KVSXOUHHXNNOPA-UHFFFAOYSA-N 6-[4-(4-pentoxyphenyl)phenyl]-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=2N=C(N)N=C(N)N=2)C=C1 KVSXOUHHXNNOPA-UHFFFAOYSA-N 0.000 claims description 2
- BVSYOXAEHGFKTL-UHFFFAOYSA-N 6-[4-[(4-chlorophenyl)methoxy]phenyl]-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC(OCC=3C=CC(Cl)=CC=3)=CC=2)=N1 BVSYOXAEHGFKTL-UHFFFAOYSA-N 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 208000002780 macular degeneration Diseases 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- FTHXGGWZAFNJEY-UHFFFAOYSA-N n-[4-amino-6-[4-(benzenesulfonyl)phenyl]-1,3,5-triazin-2-yl]acetamide Chemical compound CC(=O)NC1=NC(N)=NC(C=2C=CC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)=N1 FTHXGGWZAFNJEY-UHFFFAOYSA-N 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- YTKMHWQDZHCWRA-UHFFFAOYSA-N 2,5-dichloro-n-[4-(4,6-diamino-1,3,5-triazin-2-yl)phenyl]benzenesulfonamide Chemical compound NC1=NC(N)=NC(C=2C=CC(NS(=O)(=O)C=3C(=CC=C(Cl)C=3)Cl)=CC=2)=N1 YTKMHWQDZHCWRA-UHFFFAOYSA-N 0.000 claims 2
- BTKMCIVGDIYEEG-UHFFFAOYSA-N 6-(1-benzhydrylazetidin-3-yl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C2CN(C2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 BTKMCIVGDIYEEG-UHFFFAOYSA-N 0.000 claims 2
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- QYYZHXHYNLXWAW-UHFFFAOYSA-N trimethyl(2-phenylethynyl)stannane Chemical compound C[Sn](C)(C)C#CC1=CC=CC=C1 QYYZHXHYNLXWAW-UHFFFAOYSA-N 0.000 description 1
- ZHXAZZQXWJJBHA-UHFFFAOYSA-N triphenylbismuthane Chemical compound C1=CC=CC=C1[Bi](C=1C=CC=CC=1)C1=CC=CC=C1 ZHXAZZQXWJJBHA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
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US99011997A | 1997-12-12 | 1997-12-12 | |
US09/209,396 US6150362A (en) | 1997-12-12 | 1998-12-10 | Triazine angiogenesis inhibitors |
PCT/US1998/026369 WO1999031088A1 (fr) | 1997-12-12 | 1998-12-11 | Inhibiteurs d'angiogenese a base de triazine |
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SK866-2000A SK8662000A3 (en) | 1997-12-12 | 1998-12-11 | Triazine angiogenesis inhibitors |
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EP (1) | EP1037886B1 (fr) |
JP (1) | JP2002542144A (fr) |
KR (1) | KR20010032998A (fr) |
CN (1) | CN1290264A (fr) |
AT (1) | ATE239012T1 (fr) |
AU (1) | AU1818599A (fr) |
BG (1) | BG104584A (fr) |
BR (1) | BR9813468A (fr) |
CA (1) | CA2313776A1 (fr) |
DE (1) | DE69814151T2 (fr) |
DK (1) | DK1037886T3 (fr) |
ES (1) | ES2198088T3 (fr) |
HU (1) | HUP0202076A3 (fr) |
IL (1) | IL136339A0 (fr) |
NO (1) | NO20003018L (fr) |
PL (1) | PL344861A1 (fr) |
PT (1) | PT1037886E (fr) |
SK (1) | SK8662000A3 (fr) |
TR (1) | TR200001690T2 (fr) |
WO (1) | WO1999031088A1 (fr) |
Families Citing this family (30)
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US6943161B2 (en) | 1999-12-28 | 2005-09-13 | Pharmacopela Drug Discovery, Inc. | Pyrimidine and triazine kinase inhibitors |
FR2804113B1 (fr) * | 2000-01-26 | 2004-06-18 | Lipha | Derives animes de dihydro-1,3,5-triazine et leurs applications en therapeutique |
AR029489A1 (es) | 2000-03-10 | 2003-07-02 | Euro Celtique Sa | Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento |
AU2002247402A1 (en) * | 2001-03-23 | 2002-10-08 | Chugai Seiyaku Kabushiki Kaisha | Flt-1 ligands and their uses in the treatment of diseases regulatable by angiogenesis |
US6864255B2 (en) * | 2001-04-11 | 2005-03-08 | Amgen Inc. | Substituted triazinyl amide derivatives and methods of use |
AR037233A1 (es) | 2001-09-07 | 2004-11-03 | Euro Celtique Sa | Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento |
AR036873A1 (es) | 2001-09-07 | 2004-10-13 | Euro Celtique Sa | Piridinas aril sustituidas a, composiciones farmaceuticas y el uso de las mismas para la preparacion de un medicamento |
US7169785B2 (en) | 2001-09-21 | 2007-01-30 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
IL160984A0 (en) * | 2001-09-21 | 2004-08-31 | Reddy Us Therapeutics Inc | Triazine derivatives and pharmaceutical compositions containing the same |
US7112587B2 (en) | 2001-09-21 | 2006-09-26 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7163943B2 (en) | 2001-09-21 | 2007-01-16 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7132423B2 (en) | 2001-09-21 | 2006-11-07 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7173032B2 (en) * | 2001-09-21 | 2007-02-06 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
AU2002342018A1 (en) | 2001-10-12 | 2003-04-28 | New York University | Trisubstituted triazines compounds with antitubulin activity |
US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
US7015227B2 (en) | 2002-06-21 | 2006-03-21 | Cgi Pharmaceuticals, Inc. | Certain amino-substituted monocycles as kinase modulators |
AU2003245669A1 (en) * | 2002-06-21 | 2004-01-06 | Cellular Genomics, Inc. | Certain aromatic monocycles as kinase modulators |
US20050014753A1 (en) * | 2003-04-04 | 2005-01-20 | Irm Llc | Novel compounds and compositions as protein kinase inhibitors |
US7335770B2 (en) | 2004-03-24 | 2008-02-26 | Reddy U5 Therapeutics, Inc. | Triazine compounds and their analogs, compositions, and methods |
US7592451B2 (en) | 2005-06-23 | 2009-09-22 | New York University | Treatment for diabetes and obesity as well as method of screening compounds useful for such treatments |
FR2896161B1 (fr) * | 2006-01-13 | 2008-04-04 | Merck Sante Soc Par Actions Si | Utilisation de derives de triazines pour fabriquer un medicament ayant un effet cicatrisant ou angiogenique. |
KR100761869B1 (ko) * | 2006-07-07 | 2007-10-04 | 김현기 | 트리아진 유도체 화합물 및 이를 포함하는 암 치료용조성물 |
DE102007054416A1 (de) | 2007-11-13 | 2009-05-14 | Studiengesellschaft Kohle Mbh | Verfahren zur Herstellung von 3,6-Dihydro-1,3,5- Triazin-Derivaten für die Behandlungen von Erkrankungen, die mit dem Insulinresistenz-Syndrom assoziiert sind |
EP2300483A1 (fr) * | 2008-05-23 | 2011-03-30 | Wyeth LLC | Composés de triazine formant des inhibiteurs de pi3-kinase et mtor |
WO2015003360A2 (fr) * | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Composés thérapeutiquement actifs et leurs méthodes d'utilisation |
US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
CN106632000B (zh) * | 2016-12-19 | 2019-04-26 | 湖北工业大学 | 二芳基甲酮化合物在制备抗肿瘤药物中的应用 |
TWI846700B (zh) | 2018-06-06 | 2024-07-01 | 瑞士商梅萬特科學公司 | 治療患有慢性腎臟病之糖尿病患者之方法 |
US11813362B2 (en) | 2018-06-14 | 2023-11-14 | Poxel | Film-coated tablet comprising a triazine derivative for use in the treatment of diabetes |
CN111686113B (zh) * | 2019-03-15 | 2022-12-30 | 北京大学 | Sonic Hedgehog抑制剂及应用 |
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DE2358856C3 (de) * | 1973-11-26 | 1981-05-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Stabilisierung wäßriger Formaldehydlösungen |
DE2919496A1 (de) * | 1979-05-15 | 1980-12-04 | Degussa | Neue bisguanamine |
US4555532A (en) * | 1983-10-14 | 1985-11-26 | Hitachi, Ltd. | Epoxy resin composition |
AU9097991A (en) * | 1990-12-20 | 1992-07-22 | Nippon Shinyaku Co. Ltd. | Anticancer composition and compound |
JPH04300832A (ja) * | 1991-03-29 | 1992-10-23 | Tsumura & Co | 2,4−ジアミノ−1,3,5−トリアジン誘導体を有 効成分とするロイコトリエン拮抗剤 |
JPH04300874A (ja) * | 1991-03-29 | 1992-10-23 | Tsumura & Co | 新規2,4−ジアミノ−1,3,5−トリアジン誘導体 |
TW328955B (en) * | 1993-05-14 | 1998-04-01 | Cytec Tech Corp | Process for preparing bis- or tris-carbamate functional 1,3,5-triazines, substantially halogen contamination free crosslinker compositions and new bis-or tris-carbamate functional 1,3,5-triazines |
DE4423138A1 (de) * | 1994-07-01 | 1996-01-04 | Hoechst Ag | Elastisches Einkomponenten-Epoxidharz-System mit hoher Lagerstabilität |
-
1998
- 1998-12-11 AT AT98963082T patent/ATE239012T1/de not_active IP Right Cessation
- 1998-12-11 JP JP2000539012A patent/JP2002542144A/ja not_active Withdrawn
- 1998-12-11 CN CN98813592A patent/CN1290264A/zh active Pending
- 1998-12-11 WO PCT/US1998/026369 patent/WO1999031088A1/fr not_active Application Discontinuation
- 1998-12-11 IL IL13633998A patent/IL136339A0/xx unknown
- 1998-12-11 EP EP98963082A patent/EP1037886B1/fr not_active Expired - Lifetime
- 1998-12-11 KR KR1020007006350A patent/KR20010032998A/ko not_active Withdrawn
- 1998-12-11 HU HU0202076A patent/HUP0202076A3/hu unknown
- 1998-12-11 PT PT98963082T patent/PT1037886E/pt unknown
- 1998-12-11 PL PL98344861A patent/PL344861A1/xx unknown
- 1998-12-11 ES ES98963082T patent/ES2198088T3/es not_active Expired - Lifetime
- 1998-12-11 CA CA002313776A patent/CA2313776A1/fr not_active Abandoned
- 1998-12-11 BR BR9813468-0A patent/BR9813468A/pt not_active IP Right Cessation
- 1998-12-11 DE DE69814151T patent/DE69814151T2/de not_active Expired - Fee Related
- 1998-12-11 TR TR2000/01690T patent/TR200001690T2/xx unknown
- 1998-12-11 AU AU18185/99A patent/AU1818599A/en not_active Abandoned
- 1998-12-11 SK SK866-2000A patent/SK8662000A3/sk unknown
- 1998-12-11 DK DK98963082T patent/DK1037886T3/da active
-
2000
- 2000-06-13 NO NO20003018A patent/NO20003018L/no not_active Application Discontinuation
- 2000-07-06 BG BG104584A patent/BG104584A/bg unknown
Also Published As
Publication number | Publication date |
---|---|
HUP0202076A2 (hu) | 2002-11-28 |
IL136339A0 (en) | 2001-05-20 |
DE69814151T2 (de) | 2004-03-25 |
EP1037886B1 (fr) | 2003-05-02 |
CA2313776A1 (fr) | 1999-06-24 |
PL344861A1 (en) | 2001-11-19 |
PT1037886E (pt) | 2003-09-30 |
ES2198088T3 (es) | 2004-01-16 |
HUP0202076A3 (en) | 2003-12-29 |
TR200001690T2 (tr) | 2001-05-21 |
JP2002542144A (ja) | 2002-12-10 |
CN1290264A (zh) | 2001-04-04 |
NO20003018L (no) | 2000-08-04 |
DE69814151D1 (de) | 2003-06-05 |
EP1037886A1 (fr) | 2000-09-27 |
BR9813468A (pt) | 2001-11-13 |
BG104584A (bg) | 2001-01-31 |
DK1037886T3 (da) | 2003-08-25 |
KR20010032998A (ko) | 2001-04-25 |
AU1818599A (en) | 1999-07-05 |
WO1999031088A1 (fr) | 1999-06-24 |
NO20003018D0 (no) | 2000-06-13 |
ATE239012T1 (de) | 2003-05-15 |
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