LV12605B - EDIBLE OXOSIN AND THIASIN-OXOSOLIDINONES AS ANTI-MICROWAVE - Google Patents

EDIBLE OXOSIN AND THIASIN-OXOSOLIDINONES AS ANTI-MICROWAVE Download PDF

Info

Publication number: LV12605B
Authority: LV; Latvia
Prior art keywords: oxo; fluoro; phenyl; oxazolidinyl; methyl
Prior art date: 1993-09-09

Application number

LVP-00-142A

Other languages

English (en)

Latvian (lv)

Other versions

LV12605A (en

Inventor

Michael R. Barbachyn

Steven J. Brickner

Douglas K. Hutchinson

Original Assignee

Pharmacia & Upjohn Company

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.)

1993-09-09

Filing date

2000-10-20

Publication date

2001-05-20

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26817181&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LV12605(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2000-10-20 Application filed by Pharmacia & Upjohn Company filed Critical Pharmacia & Upjohn Company

2001-01-20 Publication of LV12605A publication Critical patent/LV12605A/xx

2001-05-20 Publication of LV12605B publication Critical patent/LV12605B/en

Links

239000004599 antimicrobial Substances 0.000 title abstract description 4
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 12
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 title description 3
150000004893 oxazines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 84
-1 thiazine oxazolidinone derivatives Chemical class 0.000 claims abstract description 37
241000186367 Mycobacterium avium Species 0.000 claims abstract description 7
241000186359 Mycobacterium Species 0.000 claims abstract description 6
241001148536 Bacteroides sp. Species 0.000 claims abstract description 5
241001112696 Clostridia Species 0.000 claims abstract description 5
241000295644 Staphylococcaceae Species 0.000 claims abstract description 5
241000187479 Mycobacterium tuberculosis Species 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
229910052739 hydrogen Inorganic materials 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
208000015181 infectious disease Diseases 0.000 claims description 6
125000003282 alkyl amino group Chemical group 0.000 claims description 5
230000000813 microbial effect Effects 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
FKZUTWSVQLXKQE-OAHLLOKOSA-N 2-[[(5s)-3-(3-fluoro-4-morpholin-4-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]isoindole-1,3-dione Chemical compound FC1=CC(N2C(O[C@@H](CN3C(C4=CC=CC=C4C3=O)=O)C2)=O)=CC=C1N1CCOCC1 FKZUTWSVQLXKQE-OAHLLOKOSA-N 0.000 claims description 2
230000000699 topical effect Effects 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 5
229940047583 cetamide Drugs 0.000 claims 4
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
GCSBYWTVHSKTNC-UHFFFAOYSA-N 1,3-oxazolidin-5-one Chemical group O=C1CNCO1 GCSBYWTVHSKTNC-UHFFFAOYSA-N 0.000 claims 1
QTPKDDZMDOCKAR-UHFFFAOYSA-N 2,2-dichloropropanamide Chemical compound CC(Cl)(Cl)C(N)=O QTPKDDZMDOCKAR-UHFFFAOYSA-N 0.000 claims 1
OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims 1
SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000002757 morpholinyl group Chemical group 0.000 claims 1
MBVRUJBHHUCNLT-LBPRGKRZSA-N n-[[(5s)-3-[3-fluoro-4-(1,3-oxazolidin-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1COCC1 MBVRUJBHHUCNLT-LBPRGKRZSA-N 0.000 claims 1
125000000160 oxazolidinyl group Chemical group 0.000 claims 1
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 abstract description 4
244000052769 pathogen Species 0.000 abstract description 3
241000894007 species Species 0.000 abstract description 3
241001148470 aerobic bacillus Species 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 146
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 70
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
239000007787 solid Substances 0.000 description 66
235000019439 ethyl acetate Nutrition 0.000 description 52
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 34
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
239000010410 layer Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 15
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
229940079593 drug Drugs 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
239000000463 material Substances 0.000 description 10
239000012267 brine Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
150000001540 azides Chemical class 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
238000001819 mass spectrum Methods 0.000 description 7
239000008194 pharmaceutical composition Substances 0.000 description 7
238000010992 reflux Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
239000005909 Kieselgur Substances 0.000 description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000013058 crude material Substances 0.000 description 5
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 4
ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000012359 Methanesulfonyl chloride Substances 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 4
230000000845 anti-microbial effect Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
YSZMSIBWWSWHEB-UHFFFAOYSA-N 3,5-difluoro-4-morpholin-4-ylaniline Chemical compound FC1=CC(N)=CC(F)=C1N1CCOCC1 YSZMSIBWWSWHEB-UHFFFAOYSA-N 0.000 description 3
NVZIFMAZKAYQJR-UHFFFAOYSA-N 3-(aminomethyl)-1,3-oxazolidin-2-one Chemical compound NCN1CCOC1=O NVZIFMAZKAYQJR-UHFFFAOYSA-N 0.000 description 3
ULZHNLWXQZVHLN-UHFFFAOYSA-N 4-(2,6-difluoro-4-nitrophenyl)morpholine Chemical compound FC1=CC([N+](=O)[O-])=CC(F)=C1N1CCOCC1 ULZHNLWXQZVHLN-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
239000002253 acid Substances 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
235000011089 carbon dioxide Nutrition 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
201000008827 tuberculosis Diseases 0.000 description 3
RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 2
OQFUNFPIPRUQAE-UHFFFAOYSA-N 1,4-thiazepane Chemical compound C1CNCCSC1 OQFUNFPIPRUQAE-UHFFFAOYSA-N 0.000 description 2
ZUAQRABPYFPGML-UHFFFAOYSA-N 3-fluoro-2-morpholin-4-ylaniline Chemical compound NC1=CC=CC(F)=C1N1CCOCC1 ZUAQRABPYFPGML-UHFFFAOYSA-N 0.000 description 2
ZEQCFSSBZPZEFJ-UHFFFAOYSA-N 4-(2-fluoro-4-nitrophenyl)morpholine Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1CCOCC1 ZEQCFSSBZPZEFJ-UHFFFAOYSA-N 0.000 description 2
PUZPGWLYSCSDBO-UHFFFAOYSA-N 4-(2-fluoro-4-nitrophenyl)thiomorpholine Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1CCSCC1 PUZPGWLYSCSDBO-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
241001630921 Chlorida Species 0.000 description 2
244000182691 Echinochloa frumentacea Species 0.000 description 2
235000008247 Echinochloa frumentacea Nutrition 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical class [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
108010059993 Vancomycin Proteins 0.000 description 2
230000009471 action Effects 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
150000001448 anilines Chemical class 0.000 description 2
125000005228 aryl sulfonate group Chemical group 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036765 blood level Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
230000003139 buffering effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000010445 mica Substances 0.000 description 2
229910052618 mica group Inorganic materials 0.000 description 2
WNRIDZUNMXATND-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-(1-oxo-1,4-thiazinan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCS(=O)CC1 WNRIDZUNMXATND-ZDUSSCGKSA-N 0.000 description 2
DPWACSJLQZCNLC-PYMCNQPYSA-N n-[[(5s)-3-[3-fluoro-4-(thiazepan-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1C1CNSCCC1 DPWACSJLQZCNLC-PYMCNQPYSA-N 0.000 description 2
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125000004076 pyridyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000004897 thiazines Chemical class 0.000 description 1
230000008719 thickening Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- C07D417/10—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 linked by a carbon chain containing aromatic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

LVP-00-142A 1993-09-09 2000-10-20 EDIBLE OXOSIN AND THIASIN-OXOSOLIDINONES AS ANTI-MICROWAVE LV12605B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US11927993A	1993-09-09	1993-09-09
US22615894A	1994-04-11	1994-04-11

Publications (2)

Publication Number	Publication Date
LV12605A LV12605A (en)	2001-01-20
LV12605B true LV12605B (en)	2001-05-20

Family

ID=26817181

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-00-142A LV12605B (en)	1993-09-09	2000-10-20	EDIBLE OXOSIN AND THIASIN-OXOSOLIDINONES AS ANTI-MICROWAVE

Country Status (20)

Country	Link
EP (1)	EP0717738B1 (fr)
JP (1)	JP3176630B2 (fr)
KR (1)	KR100301269B1 (fr)
CN (1)	CN1057087C (fr)
AT (1)	ATE185804T1 (fr)
AU (1)	AU687866B2 (fr)
CA (1)	CA2168560C (fr)
DE (2)	DE69421285T2 (fr)
DK (1)	DK0717738T3 (fr)
ES (1)	ES2139093T3 (fr)
GR (1)	GR3031809T3 (fr)
IL (1)	IL110802A (fr)
LV (1)	LV12605B (fr)
MY (1)	MY115155A (fr)
NL (1)	NL300079I1 (fr)
NZ (1)	NZ271805A (fr)
PH (1)	PH31634A (fr)
SI (1)	SI0717738T1 (fr)
TW (1)	TW293817B (fr)
WO (1)	WO1995007271A1 (fr)

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CN114957232B (zh) *	2021-05-28	2023-06-30	四川大学	一种苯并二氢恶嗪类化合物及其制备方法和抗结核的用途

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1994
- 1994-08-13 MY MYPI94002115A patent/MY115155A/en unknown
- 1994-08-16 DK DK94925765T patent/DK0717738T3/da active
- 1994-08-16 TW TW083107479A patent/TW293817B/zh not_active IP Right Cessation
- 1994-08-16 CN CN94193313A patent/CN1057087C/zh not_active Expired - Lifetime
- 1994-08-16 EP EP94925765A patent/EP0717738B1/fr not_active Expired - Lifetime
- 1994-08-16 AU AU75570/94A patent/AU687866B2/en not_active Expired
- 1994-08-16 KR KR1019960701191A patent/KR100301269B1/ko not_active Expired - Lifetime
- 1994-08-16 JP JP50866595A patent/JP3176630B2/ja not_active Expired - Lifetime
- 1994-08-16 DE DE69421285T patent/DE69421285T2/de not_active Expired - Lifetime
- 1994-08-16 AT AT94925765T patent/ATE185804T1/de active
- 1994-08-16 NZ NZ271805A patent/NZ271805A/en not_active IP Right Cessation
- 1994-08-16 SI SI9430287T patent/SI0717738T1/xx unknown
- 1994-08-16 CA CA002168560A patent/CA2168560C/fr not_active Expired - Lifetime
- 1994-08-16 WO PCT/US1994/008904 patent/WO1995007271A1/fr active Search and Examination
- 1994-08-16 DE DE10299007C patent/DE10299007I2/de active Active
- 1994-08-16 ES ES94925765T patent/ES2139093T3/es not_active Expired - Lifetime
- 1994-08-22 PH PH48830A patent/PH31634A/en unknown
- 1994-08-29 IL IL11080294A patent/IL110802A/xx not_active IP Right Cessation
1999
- 1999-11-10 GR GR990402902T patent/GR3031809T3/el unknown
2000
- 2000-10-20 LV LVP-00-142A patent/LV12605B/en unknown
2002
- 2002-01-24 NL NL300079C patent/NL300079I1/nl unknown

Also Published As

Publication number	Publication date
CA2168560A1 (fr)	1995-03-16
KR100301269B1 (ko)	2001-10-22
AU687866B2 (en)	1998-03-05
AU7557094A (en)	1995-03-27
ATE185804T1 (de)	1999-11-15
CN1057087C (zh)	2000-10-04
DE69421285D1 (de)	1999-11-25
DK0717738T3 (da)	2000-05-08
CA2168560C (fr)	2001-08-14
CN1130379A (zh)	1996-09-04
EP0717738B1 (fr)	1999-10-20
DE10299007I2 (de)	2008-09-18
JPH09502436A (ja)	1997-03-11
NZ271805A (en)	1998-02-26
DE10299007I1 (de)	2002-07-04
SI0717738T1 (en)	2000-02-29
MY115155A (en)	2003-04-30
NL300079I1 (nl)	2002-04-02
LV12605A (en)	2001-01-20
JP3176630B2 (ja)	2001-06-18
KR960704866A (ko)	1996-10-09
EP0717738A1 (fr)	1996-06-26
GR3031809T3 (en)	2000-02-29
IL110802A0 (en)	1994-11-11
TW293817B (fr)	1996-12-21
WO1995007271A1 (fr)	1995-03-16
IL110802A (en)	2000-09-28
PH31634A (en)	1999-01-12
DE69421285T2 (de)	2000-02-24
ES2139093T3 (es)	2000-02-01

Publication	Publication Date	Title
LV12605B (en)	2001-05-20	EDIBLE OXOSIN AND THIASIN-OXOSOLIDINONES AS ANTI-MICROWAVE
US5688792A (en)	1997-11-18	Substituted oxazine and thiazine oxazolidinone antimicrobials
US5547950A (en)	1996-08-20	Oxazolidinone antimicrobials containing substituted diazine moieties
CA2174107C (fr)	2005-04-12	Esters de derives de substitution d'hydroxyacetyl-piperazinyl-phenyl-oxazolidinones
US20030065175A1 (en)	2003-04-03	Novel heterocyclic compounds having antibacterial activity: process for their preparation and pharmaceutical compositions containing them
US20010047004A1 (en)	2001-11-29	Oxazolidinone thioamides with piperazine amide substituents
US20040077626A1 (en)	2004-04-22	Difluorothioacetamides of oxazolidinones as antibacterial agents
CA2614105A1 (fr)	2007-01-11	Carboxamides d'oxazolidinone contenant de l'azetidine et du cyclobutane utilises en tant qu'agents antibacteriens
US20040102494A1 (en)	2004-05-27	Novel heterocyclic compounds having antibacterial activity: process for their preparation and pharmaceutical compositions containing them
US6420360B1 (en)	2002-07-16	Sultam and sultone derived oxazolidinones
US20040072842A1 (en)	2004-04-15	Difluorothioacetamides of oxazolidinones with a glycoloylpiperazine substituent