HU213099B - Process for producing 2,8-diazabicyclo[4.3.0]nonan - Google Patents
Process for producing 2,8-diazabicyclo[4.3.0]nonan Download PDFInfo
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- HU213099B HU213099B HU9301002A HU100293A HU213099B HU 213099 B HU213099 B HU 213099B HU 9301002 A HU9301002 A HU 9301002A HU 100293 A HU100293 A HU 100293A HU 213099 B HU213099 B HU 213099B
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- alkyl
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- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
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- 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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- C—CHEMISTRY; METALLURGY
- 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
- C07D407/14—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 three or more hetero rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Fodder In General (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Amplifiers (AREA)
Description
A találmány tárgya eljárás az új 2,8-diazabiciklo[4.3.0]nonán előállítására.
Ez a vegyület közbenső termék az antibakteriális hatású 3-kinolin-karbonsav előállításához. Számos 3kinolin- és naftiridon-karbonsav vált ismertté, amelyek a 7-es helyzetben pirrolidinil-gyűrűvel vannak helyettesítve (lásd a 3 318 145 számú német szövetségi köztársaságbeli szabadalmi bejelentést a 106 489 és 153 826 számú európai szabadalmi bejelentéseket).
Az új vegyület a (IU 1) képlettel jellemezhető.
A (ΠΙ 1) képletű vegyületek az alábbi eljárással állítható elő:
Piridin-2,3-dikarbonsav-N-benzilimidből indulunk ki és (III 1) képletű vegyületet kapunk a 12. reakcióvázlat szerint.
Az alábbi példákkal a találmány további részleteit világítjuk meg.
/. referencia példa
-Metil-oktahidro-pirrolo[3,4-b]pirrol (2-Metil2,7-diazabiciklo[3.3.0]oktán)
a) 1 -Benzil-3-(/2-klór-etil/-amino)-pirrolidin-2,5-dion
74,8 g (0,4 mól) N-benzil-maleinimidet [Arch.
Pharm. 308,489 (1975)] és 52,0 g (0,4 mól) /2-klór-etiVmetilamin-hidrokloridot 400 ml dioxánba helyezünk, és
40,4 g (0,4 mól) trietil-amint csepegtetünk hozzá 20 ’C hőmérsékleten. Ezt követően 5 óra hosszat forraljuk visszafolyató hűtő alatt, majd az elegyet 2 liter jeges vízbe öntjük, háromszor extraháljuk 400 ml kloroformmal, az extraktumot vízzel mossuk, nátrium-szulfát felett szárítjuk és rotációs bepárlón bepároljuk. A maradékot (101,1 g) Kieselgélen kromatografáljuk, etilacetát:petroléter 1:2 arányú elegyével eluáljuk. 56,8 g (51 % kitermelés) olajat kapunk.
Rrérték: 0,33 (Kieselgél, etilacetát/petroléter = 1:2)
b) 5-Benzil-4,6-dioxo-l-metil-oktahidro-pirrolo(3,4b)pirrol
7,2 g (0,24 mól) 80 %-os nátrium-hidrid-szuszpenziót ásványolajban 150 ml vízmentes dimetil-formamidban (kalcium-hidrid felett szárítva) szuszpendálunk, és 62 g (0,22 mól) l-benzil-3-(/2-klór-etil/-metilamino)-pirrolidin-2,5-diont csepegtetünk hozzá 50 ml vízmentes dimetil-formamiddal készített oldatként szobahőmérsékleten. Ezt követően habzás közben exoterm reakció lép fel. További 50 ml vízmentes dimetil-formamiddal hígítjuk, 1 órát keverjük szobahőmérsékleten, majd jeges vízbe öntjük, és diklór-metánnal extraháljuk. Az extraktumot vízzel mossuk, nátrium-szulfát felett szárítjuk és rotációs bepárlón bepároljuk. A maradékot kovasavgélen etilacetát és petroléter 1:2, majd 1:1 arányú elegyével kromatografáljuk. Azt követően először 16,4 g kivonatot nyerünk vissza, majd 17,2 g (a reagált kivonatra vonatkoztatva 44%) olajos terméket izolálunk. Rrérték = 0,26.
(kovasavgél, etilacetát:petroléter =1:1).
c) 5-Benzil-l-metil-oktahidro-pirrolo[3,4-b]pirrol
1,52 g (40 mmól) lftium-alumínium-hidridet 30 ml vízmentes tetrahidrofuránba helyezünk, és 4,9 g (20 mmól) 5-benzil-4,6-dioxo-l-metil-oktahidro-pirrolo[3,4b]pirrol 15 ml vízmentes tetrahidrofuránnal készített oldatát csepegtetjük hozzá. Ezután 3 óra hosszat fonáshőmérsékleten keverjük, és egymás után 1,5 ml vizet, 1,5 ml 15%-os kálium-hidroxidot és 4,5 ml vizet csepegtetünk hozzá, majd a csapadékot leszívatjuk és tetrahidrofuránnal mossuk. A szűrletet rotációs bepárlón bepároljuk, a maradékot desztilláljuk. 3,1 g (72%) színtelen desztillátumot kapunk, amely 0,07 mbar nyomáson, 80 ’C-on forr.
d) 1 -Metil-oktahidro-pirrolo[3,4-b]pirrol
6,49 g (30 mmól) 5-benzil-l-metil-oktahidro-pirrolo[3,4-b]pirrolt 100 ml vízmentes dietiléterben oldunk, és 5,2 g foszforpentoxid fölött szárított hidrogén-kloridot vezetünk be. A keletkezett hidrogén-klorid szuszpenziót vákuumban bepároljuk, a maradékot 100 ml metanolban felvesszük. Ezután 2 g 5%-os palládium-csontszén katalizátor segítségével 4 óra hosszat hidrogénezzük 80 ’C hőmérsékleten és 50 bar nyomáson. A katalizátort ezután leszűrjük, a szűrletet bepároljuk, és a maradékot 30 ml 40%-os nátriumhidroxiddal és 50 ml dietiléterrel elegyítjük. Az éteres fázist elválasztjuk és a vizes fázist 2 x 50 ml dietiléterrel extraháljuk. Az egyesített szerves fázisokat nátrium-szulfát felett szárítjuk, bepároljuk és desztilláljuk. 1,3 g (34%) színtelen olajat kapunk, amely 12 mbar nyomáson 65-66 ’C hőmérsékleten forr. Tisztaság: több mint 99%.
II. példa
Oktahidro-pirrolo[3,4-b]piridin(2,8-diazabiciklo[4.3.0]nonán
a) 6-benzil-5,7-dioxo-oktahidro-pirrolo[3,4-b]piridin
47,6 g (0,2 mól) piridin-2,3-dikarbonsav-N-benzilimidet (1 086 637 számú nagy-britanniai szabadalmi leírás; Chem. Abstr. 68, 95695w) 400 ml glikolmonometil-éterben 15 g ruténium/csontszén katalizátoron (5%) hidrogénezünk 90 ’C hőmérsékleten, 100 bar nyomáson, amíg a számított hidrogén mennyiség fel nem használódik. Ezután a katalizátort leszűrjük, és a szűrletet rotációs bepárlón bepároljuk. 44 g olajos nyersterméket kapunk.
5%-os palládium-csontszén katalizátorral a megfelelő hidrogénezéssel kvantitatív termeléssel kapjuk a tiszta terméket, amely 67-69 ’C-on olvad.
b) 6-Benzil-oktahidro-pirrolo[3,4-b]piridin
Az Ic) példa szerint 44 g (körülbelül 0,18 mól) nyers vagy tiszta 6-benzil-5,7-dioxo-oktahidro-pirrolo[3,4-b]piridint 15,2 g (0,40 mól) lítium-alumíniumhidriddel redukálunk 390 ml vízmentes tetrahidrofuránban 10 óra leforgása alatt. A desztilláció során
24,4 g színtelen olajat kapunk, amely 0,06 mbar nyomáson 93-95 ’C-on forr.
c) Oktahidro-pirrolo[3,4-b]piridin g (0,32 mól) 6-benzil-oktahidro-pirollo[3,4b]piridint 450 ml metanolban 90 ’C hőmérsékleten, 90 bar nyomáson hidrogénezünk 7 g 5%-os palládium csontszén katalizátoron 3 óra alatt. A katalizátort leszűrjük, a szűrletet bepároljuk, és a maradékot desztilláljuk. 33,8 g (84%) színtelen szilárd test keletkezik, amely 65-67 ’C-on olvad és 78 ’C-on forr 9 mbar nyomáson.
Claims (1)
- SZABADALMI IGÉNYPONTEljárás (ΙΠ 1) képletű vegyület előállítására, azzal jellemezve, hogy piridin-2,3-dikarbonsav-N-benzil-imidet katalitikusán hidrogénezünk, majd a kapott vegyületet komplex hidriddel, előnyösen lítium-alumínium-hidriddel vagy nátrium-bór-hidriddel redukáljuk és a védőcsoportot hidrogenolitikusan lehasítjuk.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3824072 | 1988-07-15 | ||
DE3906365A DE3906365A1 (de) | 1988-07-15 | 1989-03-01 | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
Publications (3)
Publication Number | Publication Date |
---|---|
HU9301002D0 HU9301002D0 (en) | 1993-06-28 |
HUT65936A HUT65936A (en) | 1994-08-29 |
HU213099B true HU213099B (en) | 1997-02-28 |
Family
ID=25870143
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU9301002A HU213099B (en) | 1988-07-15 | 1989-07-14 | Process for producing 2,8-diazabicyclo[4.3.0]nonan |
HU893578A HU208130B (en) | 1988-07-15 | 1989-07-14 | Process for producing 7-(1-pyrrolidinyl)-3-quinoline and naphthyridinecarboxylic acid derivatives and antibacterial agents and fodder additives comprising such compounds |
HU95P/P00442P HU211472A9 (en) | 1988-07-15 | 1995-06-26 | 7-(1-pyrrolidinyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives as antibacterial agents and feed additives |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU893578A HU208130B (en) | 1988-07-15 | 1989-07-14 | Process for producing 7-(1-pyrrolidinyl)-3-quinoline and naphthyridinecarboxylic acid derivatives and antibacterial agents and fodder additives comprising such compounds |
HU95P/P00442P HU211472A9 (en) | 1988-07-15 | 1995-06-26 | 7-(1-pyrrolidinyl)-3-quinolone- and -naphthyridonecarboxylic acid derivatives as antibacterial agents and feed additives |
Country Status (24)
Country | Link |
---|---|
US (4) | US4990517A (hu) |
EP (2) | EP0350733B1 (hu) |
JP (2) | JP2771853B2 (hu) |
KR (1) | KR0156238B1 (hu) |
CN (3) | CN1027165C (hu) |
AT (2) | ATE292127T1 (hu) |
AU (5) | AU616277B2 (hu) |
CA (1) | CA1340114C (hu) |
CY (1) | CY2111B1 (hu) |
DE (4) | DE3906365A1 (hu) |
DK (1) | DK170404B1 (hu) |
ES (2) | ES2240984T4 (hu) |
FI (1) | FI94251C (hu) |
GR (1) | GR3024841T3 (hu) |
HK (1) | HK1000938A1 (hu) |
HU (3) | HU213099B (hu) |
IE (1) | IE81144B1 (hu) |
IL (1) | IL90940A (hu) |
LU (1) | LU90645I2 (hu) |
NL (1) | NL300111I2 (hu) |
NO (1) | NO168889C (hu) |
NZ (1) | NZ229914A (hu) |
PT (1) | PT91165B (hu) |
TW (1) | TW270119B (hu) |
Families Citing this family (140)
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US5190955A (en) * | 1987-01-28 | 1993-03-02 | Bayer Aktiengesellschaft | Antibacterial 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
JPH0674261B2 (ja) * | 1988-06-21 | 1994-09-21 | 塩野義製薬株式会社 | キノロンカルボン酸誘導体 |
DD285601A5 (de) * | 1988-07-15 | 1990-12-19 | Bayer Ag,De | Verfahren zur herstellung von 7-(1-pyrrolidinyl)-3-chinolon- und naphthyridoncarbonsaeure-derivaten |
DE3906365A1 (de) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
US5140033A (en) * | 1989-04-03 | 1992-08-18 | Bayer Aktiengesellschaft | Antibacterial 5-alkylquinolonecarboxylic acids |
US5252734A (en) * | 1989-04-03 | 1993-10-12 | Bayer Aktiengesellschaft | Antibacterial 5-alkylquinolonecarboxylic acids |
ES2079391T3 (es) * | 1989-04-17 | 1996-01-16 | Bayer Ag | Procedimiento para la obtencion de 2,7-diazabiciclo(3.3.0)octanos. |
US5241076A (en) * | 1989-04-17 | 1993-08-31 | Bayer Aktiengesellschaft | 1,4-diazatricyclo [6.3.0.0]undecanes |
US5177210A (en) * | 1989-04-17 | 1993-01-05 | Bayer Aktiengesellschaft | Preparation of 2,7-diazabicyclo(3.3.0)octanes |
SE8902076D0 (sv) * | 1989-06-09 | 1989-06-09 | Pharmacia Ab | Derivatives of quinoline-3-carboxanilide |
US5214051A (en) * | 1989-08-01 | 1993-05-25 | Pfizer Inc. | Thiazolyl and oxazolyl[5,4-c]piperidyl-substituted quinolone-carboxylic acid and related analogs thereof having antibacterial properties are disclosed |
US5266569A (en) * | 1989-08-16 | 1993-11-30 | Pfizer Inc. | Azatricyclo carboxylic acids useful as anti-bacterial agents |
KR950005301B1 (ko) * | 1990-09-04 | 1995-05-23 | 주식회사대웅제약 | 신규한 퀴놀론 카르복실산 유도체 |
DE4032560A1 (de) * | 1990-10-13 | 1992-04-16 | Bayer Ag | 7-(2,7-diazabicyclo(3.3.0)octyl)-3-chinolon- und -naphtyridoncarbonsaeure-derivate |
HUT64058A (en) * | 1990-12-05 | 1993-11-29 | Synphar Lab Inc | Process for producing 7-substituted-6-fluoro-1,4-dihydro-4-oxoquinoline-3-cqrboxylic acid compounds having antibacterial effect and pharmaceutical compositions comprising such compounds |
US5342846A (en) * | 1990-12-05 | 1994-08-30 | Synphar Laboratories, Inc. | 7-substituted-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid compounds and 7-(substituted triazolyl pyrrolidin-1-yl) 4-oxoquinoline-3-carboxylic acid derivatives useful as antibacterial agents |
WO1992021659A1 (en) * | 1991-05-28 | 1992-12-10 | Daiichi Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivative |
DE4120646A1 (de) * | 1991-06-22 | 1992-12-24 | Bayer Ag | 7-isoindolinyl-chinolon- und naphthyridoncarbonsaeure-derivate |
DE4121214A1 (de) * | 1991-06-27 | 1993-01-14 | Bayer Ag | 7-azaisoindolinyl-chinolon- und -naphthyridoncarbonsaeure-derivate |
US5468742A (en) * | 1991-07-19 | 1995-11-21 | Bayer Aktiengesellschaft | 8-vinyl- and 9-ethinyl-quinolone-carboxylic acids |
KR950014567B1 (ko) * | 1991-08-01 | 1995-12-08 | 주식회사대웅제약 | 신규한 퀴놀론 카르복실산 유도체 |
EP0549857A1 (en) * | 1991-12-31 | 1993-07-07 | Korea Research Institute Of Chemical Technology | Antibacterial quinolone carboxylic acid derivatives |
DE4200415A1 (de) * | 1992-01-10 | 1993-07-15 | Bayer Ag | Enantiomerenreine 2-oxa-5,8-diazabicyclo(4.3.0)nonane sowie verfahren zu ihrer herstellung |
US6004956A (en) * | 1992-01-10 | 1999-12-21 | Bayer Aktiengesellschaft | Enantiomerically pure 2-oxa-5,8-dizaabicyclo[4.3.0] nonanes and process for their preparation |
TW209865B (hu) * | 1992-01-10 | 1993-07-21 | Bayer Ag | |
KR960003616B1 (ko) * | 1992-07-23 | 1996-03-20 | 재단법인 한국화학연구소 | 우수한 항균작용을 갖는 신규한 피리돈 카르복실산 유도체 및 그의 제조방법 |
KR960003611B1 (ko) * | 1992-07-23 | 1996-03-20 | 재단법인 한국화학연구소 | 신규한 디아자비시클로 알켄 유도체 및 그의 제조방법 |
DE4232172A1 (de) * | 1992-09-25 | 1994-03-31 | Bayer Ag | 7-(Aminomethyl-oxa-7-aza-bicyclo[3.3.0]oct-7-yl)chinolon- und Naphthyridoncarbonsäure-Derivate |
DE4234078A1 (de) * | 1992-10-09 | 1994-04-14 | Bayer Ag | Chinoloncarbonsäuren |
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US4859776A (en) * | 1988-03-11 | 1989-08-22 | Abbott Laboratories | (S)-7-(3-aminopyrrolidin-1-yl)-1-(ortho, para-difluorophenyl)-1,4-dihydro-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid and method for its preparation |
JPH0674261B2 (ja) * | 1988-06-21 | 1994-09-21 | 塩野義製薬株式会社 | キノロンカルボン酸誘導体 |
DE3906365A1 (de) * | 1988-07-15 | 1990-01-18 | Bayer Ag | 7-(1-pyrrolidinyl)-3-chinolon- und -naphthyridoncarbonsaeure-derivate, verfahren sowie substituierte (oxa)diazabicyclooctane und -nonane als zwischenprodukte zu ihrer herstellung, und sie enthaltende antibakterielle mittel und futterzusatzstoffe |
DD285601A5 (de) * | 1988-07-15 | 1990-12-19 | Bayer Ag,De | Verfahren zur herstellung von 7-(1-pyrrolidinyl)-3-chinolon- und naphthyridoncarbonsaeure-derivaten |
FI95130C (fi) * | 1988-07-20 | 1995-12-27 | Sankyo Co | Menetelmä lääkeaineena käyttökelpoisten 4-oksokinoliini-3-karboksyylihapon johdannaisten valmistamiseksi |
JPH0259388A (ja) * | 1988-08-25 | 1990-02-28 | Canon Inc | 中間調画像記録方法 |
HU208005B (en) * | 1990-02-19 | 1993-07-28 | Kyorin Seiyaku Kk | Process for producing optically active 8-methoxy-quinolone-carboxylic acid derivatives and pharmaceutical compositions containing them |
DE4301246A1 (de) * | 1993-01-19 | 1994-07-21 | Bayer Ag | Chinolon- und Naphthyridoncarbonsäurederivate |
-
1989
- 1989-03-01 DE DE3906365A patent/DE3906365A1/de not_active Withdrawn
- 1989-06-19 AU AU36594/89A patent/AU616277B2/en not_active Expired
- 1989-06-29 NO NO892715A patent/NO168889C/no not_active IP Right Cessation
- 1989-06-30 DE DE58909894T patent/DE58909894D1/de not_active Expired - Lifetime
- 1989-06-30 DE DE1999175060 patent/DE19975060I2/de active Active
- 1989-06-30 ES ES96113744T patent/ES2240984T4/es not_active Expired - Lifetime
- 1989-06-30 AT AT96113744T patent/ATE292127T1/de not_active IP Right Cessation
- 1989-06-30 US US07/375,434 patent/US4990517A/en not_active Expired - Lifetime
- 1989-06-30 DE DE58909622T patent/DE58909622D1/de not_active Expired - Lifetime
- 1989-06-30 AT AT8989111950T patent/ATE135354T1/de not_active IP Right Cessation
- 1989-06-30 ES ES89111950T patent/ES2109219T3/es not_active Expired - Lifetime
- 1989-06-30 EP EP89111950A patent/EP0350733B1/de not_active Expired - Lifetime
- 1989-06-30 CN CN89104574A patent/CN1027165C/zh not_active Expired - Lifetime
- 1989-06-30 EP EP96113744A patent/EP0757990B1/de not_active Expired - Lifetime
- 1989-07-12 NZ NZ229914A patent/NZ229914A/en unknown
- 1989-07-12 JP JP1178218A patent/JP2771853B2/ja not_active Expired - Lifetime
- 1989-07-12 IL IL9094089A patent/IL90940A/en unknown
- 1989-07-13 FI FI893403A patent/FI94251C/fi active IP Right Grant
- 1989-07-13 PT PT91165A patent/PT91165B/pt not_active IP Right Cessation
- 1989-07-13 CA CA000605572A patent/CA1340114C/en not_active Expired - Lifetime
- 1989-07-14 HU HU9301002A patent/HU213099B/hu unknown
- 1989-07-14 IE IE229389A patent/IE81144B1/en not_active IP Right Cessation
- 1989-07-14 HU HU893578A patent/HU208130B/hu unknown
- 1989-07-14 DK DK350089A patent/DK170404B1/da not_active IP Right Cessation
- 1989-07-15 KR KR1019890010217A patent/KR0156238B1/ko not_active IP Right Cessation
- 1989-07-18 TW TW078105496A patent/TW270119B/zh active
-
1990
- 1990-09-10 US US07/580,906 patent/US5059597A/en not_active Expired - Lifetime
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1991
- 1991-07-30 US US07/737,631 patent/US5416096A/en not_active Expired - Lifetime
-
1992
- 1992-01-16 AU AU10283/92A patent/AU650316B2/en not_active Expired
- 1992-09-22 AU AU25286/92A patent/AU658667B2/en not_active Expired
-
1994
- 1994-01-21 CN CN94100328A patent/CN1036005C/zh not_active Expired - Lifetime
- 1994-04-19 AU AU60557/94A patent/AU668287B2/en not_active Expired
- 1994-09-15 AU AU72991/94A patent/AU671386B2/en not_active Expired
-
1995
- 1995-03-20 US US08/406,448 patent/US5607942A/en not_active Expired - Lifetime
- 1995-06-26 HU HU95P/P00442P patent/HU211472A9/hu unknown
-
1996
- 1996-04-12 CN CN96103664A patent/CN1143080A/zh active Pending
-
1997
- 1997-09-24 GR GR970402480T patent/GR3024841T3/el unknown
- 1997-12-19 HK HK97102516A patent/HK1000938A1/xx not_active IP Right Cessation
-
1998
- 1998-01-08 JP JP10013154A patent/JP3001848B2/ja not_active Expired - Lifetime
- 1998-09-14 CY CY9800027A patent/CY2111B1/xx unknown
-
2000
- 2000-09-27 LU LU90645C patent/LU90645I2/fr unknown
-
2003
- 2003-01-20 NL NL300111C patent/NL300111I2/nl unknown
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HPC4 | Succession in title of patentee |
Owner name: BAYER HEALTHCARE AG, DE |
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HPC4 | Succession in title of patentee |
Owner name: BAYER HEALTHCARE AG, DE |