KR840006660A - 6,7-디하이드로-8-(이미다졸-1-일)-5-메틸-1-옥소-1H,5H-벤조[ij]퀴놀리진-2-카르복실산 및 그 유도체의 제조방법 - Google Patents
6,7-디하이드로-8-(이미다졸-1-일)-5-메틸-1-옥소-1H,5H-벤조[ij]퀴놀리진-2-카르복실산 및 그 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840006660A KR840006660A KR1019830005377A KR830005377A KR840006660A KR 840006660 A KR840006660 A KR 840006660A KR 1019830005377 A KR1019830005377 A KR 1019830005377A KR 830005377 A KR830005377 A KR 830005377A KR 840006660 A KR840006660 A KR 840006660A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- methylquinoline
- imidazol
- halogen
- carbon atoms
- Prior art date
Links
- ADMBBALCZAJCGV-UHFFFAOYSA-N 8-imidazol-1-yl-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5(13),6,8-tetraene-3-carboxylic acid Chemical compound C1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)CCC3=C1N1C=CN=C1 ADMBBALCZAJCGV-UHFFFAOYSA-N 0.000 title 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical group 0.000 claims 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- UNSLQFMTPYHZDA-UHFFFAOYSA-N 2-methylquinolin-5-amine Chemical compound NC1=CC=CC2=NC(C)=CC=C21 UNSLQFMTPYHZDA-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- -1 alkylaminoalkyl ester salts Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical compound NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 claims 1
- JZICUKPOZUKZLL-UHFFFAOYSA-N 2-methyl-1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2NC(C)CCC2=C1 JZICUKPOZUKZLL-UHFFFAOYSA-N 0.000 claims 1
- LDLOWDQNZPNYOK-UHFFFAOYSA-N 5-imidazol-1-yl-2-methyl-1,2,3,4-tetrahydroquinoline Chemical compound N1C(C)CCC2=C1C=CC=C2N1C=CN=C1 LDLOWDQNZPNYOK-UHFFFAOYSA-N 0.000 claims 1
- PIHIJUMQCZXUSO-UHFFFAOYSA-N 5-imidazol-1-yl-2-methylquinoline Chemical compound C=1C=CC2=NC(C)=CC=C2C=1N1C=CN=C1 PIHIJUMQCZXUSO-UHFFFAOYSA-N 0.000 claims 1
- ZPFVEPGWACXJLR-UHFFFAOYSA-N 5-isothiocyanato-2-methylquinoline Chemical compound S=C=NC1=CC=CC2=NC(C)=CC=C21 ZPFVEPGWACXJLR-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 150000005690 diesters Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/03—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/04—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing quinolizine ring systems directly condensed with at least one six-membered carbocyclic ring, e.g. protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing a quinolizine ring system condensed with only one six-membered carbocyclic ring, e.g. julolidine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- 하기식의 화합물과 에스테르, 아실클로라이드, 알킬아미노알킬 에스테르염, 이미다졸 링에 질소 원자를 함유한 염 및 약학적으로 허용되는 카르복실레이트 염으로 구성되는 기로부터 선택되는 이의 유도체의 유효량과, 약학적으로 허용되는 담체로 구성되는 제약조성물.상기식에서, X는 수소 또는 플루오로, 염소 또는 브롬으로부터 선택되는 할로겐임.
- 하기식(Ⅱ)의 N-(2,2-디알콕시에틸-N′-(2-메틸퀴놀린-5-일)티오우레아를 고리화하여 하기식(Ⅲ)의 5-(2-메르캅토이미다졸-1-일)-2-메틸퀴놀린을 제조하고, 제조된 하기식(Ⅲ)의 5-(2-메르캅토)-이미다졸-1-일)-2-메틸퀴놀린을 탈황시켜 하기식(Ⅳ)의 5-(이미다졸-1-일)-2-메틸퀴놀린을 제조하며, 이를 환원하여 하기식(Ⅴ)의 5-이미다졸-1-일)-1,2,3,4-테트라하이드로-2-메틸퀴놀린을 형성하며, 형성된 하기식(Ⅴ)의 5-(이미다졸-1-일)-1,2,3,4-테트라하이드로-2-메틸퀴놀린을 하기식(Ⅳ)의 알콕시메틸렌말론산의 디에스테르와 축합 반응시켜 하기식(Ⅶ)의 중간물질을 제조하고, 제조된 하기식(Ⅶ)의 중간물질을 고리화 및 탈에스테르화하여 하기식(Ⅰ)의 6,7-디하이드로-8-(이미다졸-1-일)-5-메틸-1-옥소-1H,5H-벤조[ij]퀴닐리진-2-카르복실산을 제조하는 단계로 구성되는 것을 특징으로 하는 하기식(Ⅰ)의 6,7-디하이드로-8-(이미다졸-1-일)-5-메틸-1-옥소-1H,5H-벤조[ij]퀴닐리진-2-카르복실산을 제조하는 방법.상기식에서, X는 수소 또는 할로겐이며, R1은 각각 1-4개의 탄소원자를 함유한 알킬기이며, alk는 1-4개의 탄소원자를 함유한 알킬기이고, R2는 각각 1-4개의 탄소원자를 함유한 알킬기이거나 또는 함께 이소프로필 라디칼을 형성함.
- 제2항에 있어서, 하기식(Ⅷ)의 5-아미노-2-메틸퀴놀린과 하기식(XI)의 2,2-디알콕시에틸이소티오시아네이트를 축합시켜, 상기식(Ⅱ)의 N=(2,2-디알콕시에틸)-N′-(2-메틸퀴놀린-5-일)티오우레아를 제조하는 방법.(R1O)2CHCH2NCS (XI)상기식에서, X는 수소 또는 할로겐이며, R1은 각각 1-4개의 탄소원자를 함유한 알킬기임.
- 제2항에 있어서, 상기식(Ⅷ)의 5-아미노-2-메틸퀴놀린과 티오포스겐을 반응시켜 하기식(Ⅹ)의 5-이소티오시아네이토-2-메틸퀴놀린을 형성시킨후, 이를 하기식(XI)의 아미노 아세트 알데히드 디 알킬아세탈과 반응시켜 상기식(Ⅱ)의 N-(2,2,-디알콕시에틸)-N′-(2-메틸퀴놀린-5-일)티오우레아를 제조하는 방법.상기식에서, X는 수소 또는 할로겐이며, R1은 각각 1-4개의 탄소원자를 함유한 알킬기임.※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/441,246 US4472406A (en) | 1982-11-12 | 1982-11-12 | Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives |
| US441246 | 1999-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840006660A true KR840006660A (ko) | 1984-12-01 |
Family
ID=23752115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830005377A KR840006660A (ko) | 1982-11-12 | 1983-11-12 | 6,7-디하이드로-8-(이미다졸-1-일)-5-메틸-1-옥소-1H,5H-벤조[ij]퀴놀리진-2-카르복실산 및 그 유도체의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4472406A (ko) |
| EP (1) | EP0109285A1 (ko) |
| JP (1) | JPS59101467A (ko) |
| KR (1) | KR840006660A (ko) |
| AU (1) | AU2118283A (ko) |
| ES (1) | ES8702405A1 (ko) |
| FI (1) | FI834148A (ko) |
| GR (1) | GR79367B (ko) |
| IL (1) | IL70199A0 (ko) |
| NO (1) | NO834094L (ko) |
| NZ (1) | NZ206234A (ko) |
| OA (1) | OA07585A (ko) |
| PL (1) | PL244509A1 (ko) |
| PT (1) | PT77650B (ko) |
| ZA (1) | ZA838439B (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3471308D1 (en) * | 1983-10-17 | 1988-06-23 | Synthelabo | Imidazoline derivatives, their preparation and therapeutical use |
| DE3411997A1 (de) * | 1984-03-31 | 1985-10-17 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue redox-indikatoren |
| US4550103A (en) * | 1984-07-20 | 1985-10-29 | Warner-Lambert Company | Antibacterial 1-oxo-benzoquinolizine-2-carboxylic acids |
| US6750224B1 (en) | 1999-05-07 | 2004-06-15 | Wockhardt Limited | Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment |
| EP1175217B8 (en) * | 1999-05-07 | 2009-03-18 | Wockhardt Limited | (s)-benzoquinolizine carboxylic acids and their use as antibacterial agents |
| US6514986B2 (en) | 2000-11-22 | 2003-02-04 | Wockhardt Limited | Chiral fluoroquinolone arginine salt forms |
| US6608078B2 (en) | 2000-05-08 | 2003-08-19 | Wockhardt Limited | Antibacterial chiral 8-(substituted piperidino)-benzo [i,j] quinolizines, processes, compositions and methods of treatment |
| US7098219B2 (en) | 2000-08-01 | 2006-08-29 | Wockhart Limited | Inhibitors of cellular efflux pumps of microbes |
| US6964966B2 (en) | 2001-04-25 | 2005-11-15 | Wockhardt Limited | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| US6878713B2 (en) | 2001-04-25 | 2005-04-12 | Wockhardt Limited | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| US6664267B1 (en) * | 2002-05-28 | 2003-12-16 | Wockhardt Limited | Crystalline fluoroquinolone arginine salt form |
| WO2005023805A1 (en) | 2003-09-04 | 2005-03-17 | Wockhardt Limited | Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate |
| US10815224B2 (en) * | 2016-07-14 | 2020-10-27 | Bristol-Myers Squibb Company | Monocyclic heteroaryl substituted compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE793524A (fr) * | 1971-12-30 | 1973-06-29 | Riker Laboratories Inc | Acides benzoquinolizine-carboxyliques et leurs derives |
| JPS6019910B2 (ja) * | 1979-10-11 | 1985-05-18 | 大塚製薬株式会社 | ベンゾ〔ｉｊ〕キノリジン−２−カルボン酸誘導体及びその製造法 |
| JPS5630964A (en) * | 1979-08-22 | 1981-03-28 | Kyorin Pharmaceut Co Ltd | Novel substituted quinolinecarboxylic acid and its preparation |
| NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
| JPS5788182A (en) * | 1980-11-21 | 1982-06-01 | Dai Ichi Seiyaku Co Ltd | Pyrido(1,2,3-de)(1,4)benzoxazinecarboxylic acid derivative |
| AT380250B (de) * | 1980-12-18 | 1986-04-25 | Otsuka Pharma Co Ltd | Verfahren zur herstellung benzoheterocyclischer verbindungen |
| US4404207A (en) * | 1981-11-06 | 1983-09-13 | Riker Laboratories, Inc. | Antimicrobial 8-substituted benzo [IJ]quinolizines |
-
1982
- 1982-11-12 US US06/441,246 patent/US4472406A/en not_active Expired - Fee Related
-
1983
- 1983-11-09 NO NO834094A patent/NO834094L/no unknown
- 1983-11-10 ES ES527165A patent/ES8702405A1/es not_active Expired
- 1983-11-10 OA OA58155A patent/OA07585A/xx unknown
- 1983-11-11 PL PL24450983A patent/PL244509A1/xx unknown
- 1983-11-11 ZA ZA838439A patent/ZA838439B/xx unknown
- 1983-11-11 EP EP83306909A patent/EP0109285A1/en not_active Withdrawn
- 1983-11-11 FI FI834148A patent/FI834148A/fi not_active Application Discontinuation
- 1983-11-11 NZ NZ206234A patent/NZ206234A/en unknown
- 1983-11-11 AU AU21182/83A patent/AU2118283A/en not_active Abandoned
- 1983-11-11 JP JP58212305A patent/JPS59101467A/ja active Pending
- 1983-11-11 GR GR72948A patent/GR79367B/el unknown
- 1983-11-11 IL IL70199A patent/IL70199A0/xx unknown
- 1983-11-11 PT PT77650A patent/PT77650B/pt unknown
- 1983-11-12 KR KR1019830005377A patent/KR840006660A/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO834094L (no) | 1984-05-14 |
| OA07585A (fr) | 1985-03-31 |
| ES527165A0 (es) | 1987-01-01 |
| IL70199A0 (en) | 1984-02-29 |
| AU2118283A (en) | 1984-05-17 |
| US4472406A (en) | 1984-09-18 |
| NZ206234A (en) | 1986-10-08 |
| ZA838439B (en) | 1985-06-26 |
| JPS59101467A (ja) | 1984-06-12 |
| FI834148A (fi) | 1984-05-13 |
| PT77650A (en) | 1983-12-01 |
| GR79367B (ko) | 1984-10-22 |
| ES8702405A1 (es) | 1987-01-01 |
| PL244509A1 (en) | 1985-01-16 |
| FI834148A0 (fi) | 1983-11-11 |
| PT77650B (en) | 1986-03-27 |
| EP0109285A1 (en) | 1984-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840006660A (ko) | 6,7-디하이드로-8-(이미다졸-1-일)-5-메틸-1-옥소-1H,5H-벤조[ij]퀴놀리진-2-카르복실산 및 그 유도체의 제조방법 | |
| KR910000657A (ko) | 옥사-또는 티아-졸린 유도체 | |
| KR830006219A (ko) | 아미노산 유도체의 제조방법 | |
| KR830007685A (ko) | 세팔로스포린 유도체의 제조방법 | |
| KR870003998A (ko) | 퀴나졸린 유도체류의 제조방법 | |
| KR840008021A (ko) | 4-치환된-2-아제티디논 화합물의 제조방법 | |
| KR920701174A (ko) | 퀴나졸린-3-알카노산 유도체, 이의 염 및 이의 제조방법 | |
| KR850002964A (ko) | 심장병 치료제의 제조방법 | |
| KR860006452A (ko) | 피페리딘 화합물의 제조 방법 | |
| KR830007570A (ko) | 아자비시클로-옥탄-카복실산의 제조방법 | |
| KR910004590A (ko) | 특정 벤조피란 및 벤조티오피란 유도체 | |
| KR860008173A (ko) | 치환된 n-[(4-피페리딘일)알킬]비사이클축합 옥사졸아민 및 티아졸아민의 제조방법 | |
| KR850004585A (ko) | 신규 아미노과니딘 유도체의 제조방법 | |
| KR850007427A (ko) | 항균 화합물의 제조방법 | |
| KR840006482A (ko) | 디히드로피라졸로 [3,4-b]피리딘 유도체의 제조방법 | |
| KR840000534A (ko) | 디히드로피리딘 화합물류의 제조방법 | |
| KR880000450A (ko) | 세팔로스포린 유도체의 제조방법 | |
| KR910016689A (ko) | 우레아 유도체 및 이의 염, 이를 함유하는 약제학적 조성물 및 이의 제조방법 | |
| KR890000456A (ko) | 폴리옥시겐화된 라단유도체 이의 제조방법 및 이의 약제로서의 용도 | |
| KR890009858A (ko) | 카바조일 유도체 | |
| KR850002274A (ko) | 지방산 유도체의 제조방법 | |
| KR830007683A (ko) | 7β-[2-(2-아미노-4-티아졸릴)-2-(신)-메톡시 아미노 아세트 아미도]-3-세펨-4-카복실산의 에스테르의 제조방법 | |
| KR860007266A (ko) | 알켄아미도 세팔로스포린 에스테르의 제조방법 | |
| KR900004708A (ko) | 카르바진산 유도체, 그 제조방법 및 용도 | |
| KR840005453A (ko) | 펜엠 유도체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SUBM | Surrender of laid-open application requested |