SK1842003A3 - Novel heteroaryl derivatives and the use thereof as pharmaceuticals - Google Patents

Novel heteroaryl derivatives and the use thereof as pharmaceuticals Download PDF

Info

Publication number: SK1842003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; radical; substituted; alkylamino; unsubstituted
Prior art date: 2000-07-21

Application number

SK1842003A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Emig

Eckhard Gunther

Jurgen Schmidt

Bernd Nickel

Bernhard Kutscher

Original Assignee

Zentaris Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-07-21

Filing date

2001-07-18

Publication date

2004-10-05

2001-07-18 Application filed by Zentaris Gmbh filed Critical Zentaris Gmbh

2004-10-05 Publication of SK1842003A3 publication Critical patent/SK1842003A3/sk

Links

125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 12
239000003814 drug Substances 0.000 title claims abstract description 8
206010028980 Neoplasm Diseases 0.000 claims abstract description 9
238000004519 manufacturing process Methods 0.000 claims abstract description 3
-1 phenylethoxy, nitro , amino Chemical group 0.000 claims description 334
229910052736 halogen Inorganic materials 0.000 claims description 119
150000002367 halogens Chemical class 0.000 claims description 117
125000000217 alkyl group Chemical group 0.000 claims description 113
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 80
125000003282 alkyl amino group Chemical group 0.000 claims description 73
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 72
229910052739 hydrogen Inorganic materials 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 68
125000001153 fluoro group Chemical group F* 0.000 claims description 57
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 56
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 52
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 51
125000003118 aryl group Chemical group 0.000 claims description 46
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 43
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 33
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 31
125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 29
150000003254 radicals Chemical class 0.000 claims description 28
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 27
150000003248 quinolines Chemical class 0.000 claims description 26
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 25
229910052731 fluorine Inorganic materials 0.000 claims description 21
239000011737 fluorine Substances 0.000 claims description 21
125000003545 alkoxy group Chemical group 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 17
125000004043 oxo group Chemical group O=* 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000005915 C6-C14 aryl group Chemical group 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
RPBWZBPLNQWXMX-UHFFFAOYSA-N [C].N1=CC=CC2=CC=CC=C21 Chemical group [C].N1=CC=CC2=CC=CC=C21 RPBWZBPLNQWXMX-UHFFFAOYSA-N 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
150000001412 amines Chemical class 0.000 claims description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
150000005840 aryl radicals Chemical class 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
150000003536 tetrazoles Chemical class 0.000 claims description 2
PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 claims 1
125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims 1
229910052727 yttrium Inorganic materials 0.000 claims 1
210000004027 cell Anatomy 0.000 description 13
239000000203 mixture Substances 0.000 description 9
239000013543 active substance Substances 0.000 description 5
238000003556 assay Methods 0.000 description 5
239000000243 solution Substances 0.000 description 5
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230000001028 anti-proliverative effect Effects 0.000 description 4
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238000002474 experimental method Methods 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
210000004881 tumor cell Anatomy 0.000 description 4
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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230000000694 effects Effects 0.000 description 3
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229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
244000144977 poultry Species 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- C07D401/06—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 only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Hematology (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK1842003A 2000-07-21 2001-07-18 Novel heteroaryl derivatives and the use thereof as pharmaceuticals SK1842003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10035928A DE10035928A1 (de)	2000-07-21	2000-07-21	Neue Heteroaryl-Derivate und deren Verwendung als Arzneimittel
PCT/EP2001/008261 WO2002008192A1 (fr)	2000-07-21	2001-07-18	Nouveaux derives heteroaryle et utilisation en tant qu'agents pharmaceutiques

Publications (1)

Publication Number	Publication Date
SK1842003A3 true SK1842003A3 (en)	2004-10-05

Family

ID=7649980

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1842003A SK1842003A3 (en)	2000-07-21	2001-07-18	Novel heteroaryl derivatives and the use thereof as pharmaceuticals

Country Status (23)

Country	Link
US (5)	US6890926B2 (fr)
EP (1)	EP1305290A1 (fr)
JP (1)	JP2004504381A (fr)
KR (1)	KR20030022287A (fr)
CN (1)	CN1443171A (fr)
AR (1)	AR033678A1 (fr)
AU (2)	AU2001279757B2 (fr)
BG (1)	BG107508A (fr)
BR (1)	BR0112589A (fr)
CA (1)	CA2353369A1 (fr)
CZ (1)	CZ2003415A3 (fr)
DE (1)	DE10035928A1 (fr)
HU (1)	HUP0300838A2 (fr)
IL (1)	IL153361A0 (fr)
MX (1)	MXPA02012565A (fr)
NO (1)	NO20030298D0 (fr)
NZ (1)	NZ524154A (fr)
PL (1)	PL358788A1 (fr)
RU (1)	RU2265602C2 (fr)
SK (1)	SK1842003A3 (fr)
TW (1)	TWI228505B (fr)
WO (1)	WO2002008192A1 (fr)
ZA (1)	ZA200210180B (fr)

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CA2712500A1 (fr) *	2008-01-24	2009-07-30	Vitae Pharmaceuticals, Inc.	Carbazate cyclique et inhibiteurs du type semi-carbazide de la 11beta-hydroxysteroide deshydrogenase 1
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WO2009117109A1 (fr) *	2008-03-18	2009-09-24	Vitae Pharmaceuticals, Inc.	Inhibiteurs de la 11-bêta-hydroxystéroïde déshydrogénase de type 1
JP5451752B2 (ja) *	2008-05-01	2014-03-26	ヴァイティーファーマシューティカルズ，インコーポレイテッド	１１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状インヒビター
US8592410B2 (en)	2008-05-01	2013-11-26	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
TW201004945A (en)	2008-05-01	2010-02-01	Vitae Pharmaceuticals Inc	Cyclic inhibitors of 11beta-hydroxysteroid dehydrogenase 1
BRPI0911764A2 (pt) *	2008-05-01	2015-10-06	Boehringer Ingelheim Int	inibidores cíclicos de 11beta-hidroxiesteroide desigrogenase 1
TW201016691A (en)	2008-07-25	2010-05-01	Boehringer Ingelheim Int	Inhibitors of 11beta-hydroxysteroid dehydrogenase 1
EP2687525B1 (fr)	2008-07-25	2015-09-23	Boehringer Ingelheim International GmbH	Inhibiteurs cycliques de la 11-bêta-hydroxystéroïde déshydrogénase 1
JP5679997B2 (ja)	2009-02-04	2015-03-04	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	１１β−ヒドロキシステロイドデヒドロゲナーゼ１の環状阻害剤
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MA33216B1 (fr)	2009-04-30	2012-04-02	Boehringer Ingelheim Int	Inhibiteurs cycliques de la 11béta-hydroxysteroïde déshydrogénase 1
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US8927539B2 (en)	2009-06-11	2015-01-06	Vitae Pharmaceuticals, Inc.	Cyclic inhibitors of 11β-hydroxysteroid dehydrogenase 1 based on the 1,3-oxazinan-2-one structure
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2000
- 2000-07-21 DE DE10035928A patent/DE10035928A1/de not_active Withdrawn
2001
- 2001-07-18 BR BR0112589-3A patent/BR0112589A/pt not_active IP Right Cessation
- 2001-07-18 PL PL01358788A patent/PL358788A1/xx not_active Application Discontinuation
- 2001-07-18 SK SK1842003A patent/SK1842003A3/sk not_active Application Discontinuation
- 2001-07-18 CZ CZ2003415A patent/CZ2003415A3/cs unknown
- 2001-07-18 WO PCT/EP2001/008261 patent/WO2002008192A1/fr not_active Application Discontinuation
- 2001-07-18 JP JP2002514099A patent/JP2004504381A/ja active Pending
- 2001-07-18 KR KR10-2003-7000707A patent/KR20030022287A/ko not_active Withdrawn
- 2001-07-18 RU RU2003105278/04A patent/RU2265602C2/ru not_active IP Right Cessation
- 2001-07-18 NZ NZ524154A patent/NZ524154A/en unknown
- 2001-07-18 CN CN01813158A patent/CN1443171A/zh active Pending
- 2001-07-18 IL IL15336101A patent/IL153361A0/xx unknown
- 2001-07-18 EP EP01957978A patent/EP1305290A1/fr not_active Withdrawn
- 2001-07-18 MX MXPA02012565A patent/MXPA02012565A/es unknown
- 2001-07-18 HU HU0300838A patent/HUP0300838A2/hu unknown
- 2001-07-18 AU AU2001279757A patent/AU2001279757B2/en not_active Ceased
- 2001-07-18 AU AU7975701A patent/AU7975701A/xx active Pending
- 2001-07-20 AR ARP010103481A patent/AR033678A1/es not_active Application Discontinuation
- 2001-07-20 CA CA002353369A patent/CA2353369A1/fr not_active Abandoned
- 2001-07-20 US US09/910,141 patent/US6890926B2/en not_active Expired - Fee Related
- 2001-07-23 TW TW090117947A patent/TWI228505B/zh not_active IP Right Cessation
2002
- 2002-12-17 ZA ZA200210180A patent/ZA200210180B/xx unknown
2003
- 2003-01-20 NO NO20030298A patent/NO20030298D0/no unknown
- 2003-01-30 BG BG107508A patent/BG107508A/bg unknown
- 2003-11-14 US US10/713,859 patent/US7056912B2/en not_active Expired - Fee Related
- 2003-12-19 US US10/741,310 patent/US6936615B2/en not_active Expired - Fee Related
2005
- 2005-04-14 US US11/105,622 patent/US7026310B2/en not_active Expired - Fee Related
- 2005-06-14 US US11/152,599 patent/US20050245523A1/en not_active Abandoned

Also Published As

Publication number	Publication date
RU2265602C2 (ru)	2005-12-10
US6890926B2 (en)	2005-05-10
MXPA02012565A (es)	2003-09-22
DE10035928A1 (de)	2002-03-07
PL358788A1 (en)	2004-08-23
US20050176744A1 (en)	2005-08-11
JP2004504381A (ja)	2004-02-12
KR20030022287A (ko)	2003-03-15
US7026310B2 (en)	2006-04-11
CA2353369A1 (fr)	2002-01-21
US6936615B2 (en)	2005-08-30
US7056912B2 (en)	2006-06-06
HUP0300838A2 (hu)	2003-07-28
US20040097530A1 (en)	2004-05-20
AU7975701A (en)	2002-02-05
CN1443171A (zh)	2003-09-17
US20050245523A1 (en)	2005-11-03
ZA200210180B (en)	2003-02-12
AR033678A1 (es)	2004-01-07
AU2001279757B2 (en)	2005-05-26
US20040132747A1 (en)	2004-07-08
BR0112589A (pt)	2003-05-20
TWI228505B (en)	2005-03-01
NZ524154A (en)	2005-02-25
CZ2003415A3 (cs)	2004-05-12
WO2002008192A1 (fr)	2002-01-31
US20020103214A1 (en)	2002-08-01
EP1305290A1 (fr)	2003-05-02
NO20030298L (no)	2003-01-20
BG107508A (bg)	2003-09-30
IL153361A0 (en)	2003-07-06
NO20030298D0 (no)	2003-01-20

Legal Events

Date	Code	Title	Description
2010-08-09	FC9A	Refused patent application

Publication	Publication Date	Title
SK1842003A3 (en)	2004-10-05	Novel heteroaryl derivatives and the use thereof as pharmaceuticals
RU2267488C2 (ru)	2006-01-10	Производные акридина, способ их получения и фармацевтическая композиция на их основе
SK1942003A3 (en)	2003-12-02	Novel heteroaryl derivatives and use thereof as anti-tumour agents
RU2262339C2 (ru)	2005-10-20	Производные индолил-3-глиоксиловой кислоты - соединения, обладающие противоопухолевой активностью, фармацевтическая композиция, противоопухолевое средство (варианты)
JP2978967B2 (ja)	1999-11-15	新規ピペラジン誘導体、その製造方法及びそれを含有する組成物
RU2270196C9 (ru)	2007-11-27	Производные индола, способ их получения, лекарственное средство и способ ингибирования роста опухолевых клеток
US6346520B1 (en)	2002-02-12	Cyanoguanidines as cell proliferation inhibitors
SK161199A3 (en)	2000-06-12	Cyanoguanidines as cell proliferation inhibitors
JP2000502988A (ja)	2000-03-14	放射線活性化サイトトキシン療法
US12128015B2 (en)	2024-10-29	APE/REF1 inhibitors for the treatment of cancer
NZ500953A (en)	2001-07-27	Cyanoamidines as cell proliferation inhibitors