KR850001199A - 1,8-나프티리딘 유도체의 제조법 - Google Patents
1,8-나프티리딘 유도체의 제조법 Download PDFInfo
- Publication number
- KR850001199A KR850001199A KR1019840004455A KR840004455A KR850001199A KR 850001199 A KR850001199 A KR 850001199A KR 1019840004455 A KR1019840004455 A KR 1019840004455A KR 840004455 A KR840004455 A KR 840004455A KR 850001199 A KR850001199 A KR 850001199A
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- South Korea
- Prior art keywords
- formula
- compound
- ester
- carbon atoms
- lower alkyl
- Prior art date
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- 150000005058 1,8-naphthyridines Chemical class 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000002148 esters Chemical class 0.000 claims 11
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical class C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- 238000003795 desorption Methods 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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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- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Saccharide Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- (i) 일반식(II)의 카르복실산 또는 그 에스테르와 일반식(III)의 피롤리딘 유도체를 반응시켜, 일반식(I)의 화합물 또는 그 에스테르를 제조하거나, (ii) 일반식(IV)의 피리딘 유도체를 염기 존재하에 폐환시켜, 다음 일반식(V)의 화합물을 생성시키고, 이어서 탈수소하여, 다음 일반식(I')의 화합물을 생성시키고, 필요한 경우에는 가수분해하여 일반식(I)의 화합물 또는 탄소수 1내지 5의 저급알킬에스테르를 제조하거나, 또는, (iii) 일반식(VI)의 β-아미노아크릴산에스테르를 염기 존재하에 폐환시켜, 일반식(I')의 화합물을 생성시키고, 필요한 경우에는 가수분해하여, 일반식(I)의 화합물 또는 탄소수 1내지 5의 저급알킬에스테르를 제조하거나, (iv) 일반식(VII)의 화합물 또는 그 에스테르를 보호기의 탈리반응에 의해 일반식(I)의 화합물 또는 그 에스테르를 제조하거나, (v) 일반식(I)의 1,8-나프티리딘 유도체의 에스테르를 가수분해하여 일반식(I)의 화합물을 제조하거나, (vi) 일반식(I)의 1,8-나프티리딘 유도체를 에스테르화하여 일반식(I)의 화합물의 에스테르를 제조하거나, (vii) 일반식(VIII)의 화합물 또는 그 에스테르를 염기 존재하에 알킬화하여, 일반식(IX)의 화합물 또는 그 에스테르를 생성시키고, 그 화합물의 보호기를 탈리시켜, 일반식(I)에 있어 R1이 탄소수 1내지 5의 저급알킬기인 화합물 또는 그 에스테르를 제조하거나, (viii) 필요한 경우에는 일반식(I)의 1,8-나프티리딘유도체 또는 그 에스테르를 산, 염기 또는 금속염으로 처리하여 일반식(I)의 화합물 또는 그 에스테르의 염을 제조함을 특징으로 하는 일반식(I)의 화합물 또는 그 에스테르 또는 그 염의 제조방법.(식중, R1,R2및 R3는 각각 같거나 다르며, 수소원자 또는 탄소수 1내지 5의 저급알킬기를 의미함.)(식중, X는 후기하는 피롤리딘 유도체(III)와 치환할 수 있는 관능기를 의미함.)(식중, R1,R2및 R3는 상술한 바와같음.)(식중, Y는 같거나 다르며, 탄소수 1내지 5의 저급알킬기를 의미하며, R1,R2및 R3는 상술한 바와같음.)(식중, R1,R2,R3및 Y는 상술한 바와 같음)(식중, R1,R2,R3및 Y는 상술한 바와 같음)(식중, Z는 할로겐원자를 나타내고, R1,R2,R3및 Y는 상술한 바와 같음.)(식중, R4는 보호기를 의미하고, R1,R2및 R3는 상술한 바와 같음.)(식중, R1,R2,R3및 Y는 상술한 바와 같음.)(식중, R1'은 탄소수 1내지 5의 저급알킬기를 의미하며, R2,R3및 R4는 상술한 바와 같음.)※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58-133,000 | 1983-07-27 | ||
JP58138000A JPS6028978A (ja) | 1983-07-27 | 1983-07-27 | 1,8−ナフチリジン誘導体 |
JP138000 | 1983-07-27 | ||
JP59117266A JPS60260577A (ja) | 1984-06-06 | 1984-06-06 | 1,8−ナフチリジン誘導体 |
JP59-117,266 | 1984-06-06 | ||
JP117266 | 1984-06-06 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR850001199A true KR850001199A (ko) | 1985-03-16 |
KR900006750B1 KR900006750B1 (ko) | 1990-09-20 |
Family
ID=26455408
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840004455A KR900006750B1 (ko) | 1983-07-27 | 1984-07-26 | 1,8-나프티리딘 유도체의 제조법 |
Country Status (16)
Country | Link |
---|---|
US (1) | US4649144A (ko) |
EP (1) | EP0132845B1 (ko) |
KR (1) | KR900006750B1 (ko) |
AT (1) | ATE33494T1 (ko) |
AU (1) | AU565898B2 (ko) |
CA (1) | CA1327580C (ko) |
CS (1) | CS274601B2 (ko) |
DD (1) | DD228256A5 (ko) |
DE (1) | DE3470420D1 (ko) |
DK (1) | DK160276C (ko) |
ES (2) | ES8603501A1 (ko) |
FI (1) | FI77862C (ko) |
HU (1) | HU194561B (ko) |
PH (1) | PH21696A (ko) |
SU (2) | SU1482527A3 (ko) |
YU (3) | YU43371B (ko) |
Families Citing this family (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5281612A (en) * | 1982-09-09 | 1994-01-25 | Warner-Lambert Company | Naphthyridine antibacterial agents |
US4665079A (en) * | 1984-02-17 | 1987-05-12 | Warner-Lambert Company | Antibacterial agents |
DE3574380D1 (en) * | 1984-02-17 | 1989-12-28 | Daiichi Seiyaku Co | 1,8-naphthyridine derivatives |
DE3508816A1 (de) * | 1985-01-10 | 1986-07-10 | Bayer Ag, 5090 Leverkusen | 6,7-disubstituierte 1-cyclopropyl-1,4-dihydro-4-oxo-1,8-naphtyridin-3-carbonsaeuren |
US4663457A (en) * | 1985-01-23 | 1987-05-05 | Warner-Lambert Company | 1-cyclopropyl-6,7-dihalo-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid and their esters, useful as intermediates for preparing the 7-amine substituted naphthyridines |
JPH0635457B2 (ja) * | 1985-06-28 | 1994-05-11 | 杏林製薬株式会社 | ピリドンカルボン酸誘導体およびその製造方法 |
AU594983B2 (en) * | 1985-10-29 | 1990-03-22 | Dainippon Pharmaceutical Co. Ltd. | Novel quinoline derivatives and processes for preparation thereof |
JPH089597B2 (ja) * | 1986-01-21 | 1996-01-31 | 杏林製薬株式会社 | 選択毒性に優れた8‐アルコキシキノロンカルボン酸およびその塩並びにその製造方法 |
US4692454A (en) * | 1986-02-03 | 1987-09-08 | Warner-Lambert Company | Opthalmic use of quinolone antibiotics |
US4840956A (en) * | 1986-02-18 | 1989-06-20 | Warner-Lambert Company | Novel disubstituted-7-pyrrolidinoquinoline antibacterial agents |
US4771055A (en) * | 1986-07-28 | 1988-09-13 | Warner-Lambert Company | 7-[[3-(aminomethyl)-3-alkyl]-1-pyrrolidinyl]-quinoline-carboxylic acids |
US4954507A (en) * | 1986-10-08 | 1990-09-04 | Bristol-Myers Company | 1-tertiary-alkyl-substituted naphthyridine carboxylic acid antibacterial agents |
US4775686A (en) * | 1986-10-15 | 1988-10-04 | Schering Corporation | Naphthyridine derivatives and method for treating allergic reactions |
US4916131A (en) * | 1986-10-15 | 1990-04-10 | Schering Corporation | Naphthyridine derivatives and method for treating allergic reactions |
US5037826A (en) * | 1986-10-15 | 1991-08-06 | Schering Corporation | 1-substituted naphthyridine and pyridopyrazine derivatives |
FR2607504B1 (fr) * | 1986-12-02 | 1989-01-27 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
FR2607506B1 (fr) * | 1986-12-02 | 1989-01-06 | Rhone Poulenc Sante | Nouveaux derives de l'isoindolinone, leur preparation et les compositions pharmaceutiques qui les contiennent |
US4962112A (en) * | 1987-08-04 | 1990-10-09 | Abbott Laboratories | 7-(2-methyl-4-aminopyrrolidinyl)naphthryidine and quinoline compounds |
US4920120A (en) | 1988-01-25 | 1990-04-24 | Warner-Lambert Company | Antibacterial agents |
US5585491A (en) * | 1988-01-25 | 1996-12-17 | Otsuka Pharmaceutical Co., Ltd. | Antibacterial agents |
US5173484A (en) * | 1988-02-05 | 1992-12-22 | Bayer Aktiengesellschaft | Quinolone- and naphthyridone carboxylic acid derivatives, process for their production, antibacterial compositions and feed additives containing them |
EP0333020A3 (en) * | 1988-03-18 | 1991-03-20 | Abbott Laboratories | Process for the preparation of substituted pyridines |
EP0339406A1 (en) * | 1988-04-19 | 1989-11-02 | Hokuriku Pharmaceutical Co.,Ltd | Quinoline-3-carboxylic acid derivatives, process for preparing the same, and composition exhibiting excellent antibacterial effect containing the same |
US5057520A (en) * | 1989-03-24 | 1991-10-15 | Abbott Laboratories | 7-(peptidylpyrolidinyl)naphthyridine antibacterial compounds |
US5057523A (en) * | 1988-09-22 | 1991-10-15 | Abbott Laboratories | Dipeptide quinolone derivatives |
CA1332605C (en) * | 1988-10-03 | 1994-10-18 | Yasuhiro Nishitani | Pyridonecarboxylic acids |
US5262417A (en) * | 1988-12-06 | 1993-11-16 | The Upjohn Company | Antibacterial quinolone compounds |
AU623475B2 (en) * | 1989-01-16 | 1992-05-14 | Laboratoire Roger Bellon | New benzo(1,8)naphthyridine derivatives, their preparation and compositions containing them |
FR2641783B1 (fr) * | 1989-01-16 | 1991-04-05 | Bellon Labor Sa Roger | Nouveaux derives de benzonaphtyridine-1,8, leur preparation et les compositions qui les contiennent |
NZ232092A (en) * | 1989-01-16 | 1992-05-26 | Bellon Labor Sa Roger | 8-halo-7-fluoro-4-oxo-1,4-dihydro-benzo(b)(1,8) naphthyridine-3-carboxylic acid esters and preparation thereof |
US4916141A (en) * | 1989-03-28 | 1990-04-10 | Warner-Lambert Company | (S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid |
DE3918544A1 (de) * | 1989-06-07 | 1990-12-13 | Bayer Ag | Verfahren zur herstellung von 7-(3-amino- sowie 3-amino-methyl-1-pyrrolidinyl)-3-chinolon- carbonsaeuren sowie -naphthyridoncarbonsaeuren |
CA2106840A1 (en) * | 1992-09-25 | 1994-03-26 | Marco Baroni | Heteroarylazetidines and -pyrrolidines, process for their preparation and pharmaceutical compositions containing them |
ATE239720T1 (de) * | 1995-02-02 | 2003-05-15 | Daiichi Seiyaku Co | Heterozyklische verbindungen |
KR20000052892A (ko) * | 1996-10-30 | 2000-08-25 | 빌프리더 하이더 | 나프티리딘 화합물의 제조 방법 및 신규 중간 생성물 |
US5739342A (en) * | 1997-03-03 | 1998-04-14 | Abbott Laboratories | Process for the preparation of nicotinic acids |
US6441182B1 (en) | 1999-06-10 | 2002-08-27 | Bayer Aktiengesellschaft | Method for the production of 2,6-dichloro-5-fluoro-nicotinic acid and coarse and particularly pure 2,6-dichloro-5-fluoro-nicotinic acid |
US6777420B2 (en) | 2001-06-15 | 2004-08-17 | Microbiotix, Inc. | Heterocyclic antibacterial compounds |
FR2928150A1 (fr) * | 2008-02-29 | 2009-09-04 | Vetoquinol Sa Sa | Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens |
EP2145891A1 (en) * | 2008-07-09 | 2010-01-20 | Vetoquinol S.A. | 9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials |
PL2776431T3 (pl) | 2011-11-08 | 2016-11-30 | Stanowiące antybiotyki pochodne 2-okso-oksazolidyno-3,5-diylu | |
EP3183232B1 (en) | 2014-08-22 | 2023-05-03 | The Arizona Board of Regents on behalf of The University of Arizona | Substituted 1-arylethyl-4-acylaminopiperidine derivatives as opioid/alpha-adrenoreceptor modulators and method of their preparation |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2017148B (en) * | 1978-03-22 | 1983-01-12 | Pompey Acieries | Nickel chromium iron alloys possessing very high resistantance to carburization at very high temperature |
AR223983A1 (es) * | 1978-08-25 | 1981-10-15 | Dainippon Pharmaceutical Co | Un procedimiento para-preparar derivados de acido 6-halogeno-4-oxo-7-(1-piperazinil)-1,8-naftiridin-3-carboxilico |
JPS5522699A (en) | 1979-08-10 | 1980-02-18 | Yamanouchi Pharmaceut Co Ltd | Novel 3-amino-1-benzylpyrrolidine derivative |
JPS5649382A (en) * | 1979-09-28 | 1981-05-02 | Dainippon Pharmaceut Co Ltd | 6-fluoro-7-cyclic amino-1,8-naphthylidine derivative and its salt |
DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
JPS57106681A (en) * | 1980-12-24 | 1982-07-02 | Dainippon Pharmaceut Co Ltd | 1,8-naphthyridine derivative and its salt |
US4382937A (en) * | 1981-02-27 | 1983-05-10 | Dainippon Pharmaceutical Co., Ltd. | Naphthyridine derivatives and their use as anti-bacterials |
IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
-
1984
- 1984-07-19 CS CS557584A patent/CS274601B2/cs unknown
- 1984-07-20 US US06/632,853 patent/US4649144A/en not_active Expired - Lifetime
- 1984-07-20 AU AU30910/84A patent/AU565898B2/en not_active Ceased
- 1984-07-24 CA CA000459527A patent/CA1327580C/en not_active Expired - Fee Related
- 1984-07-25 AT AT84108822T patent/ATE33494T1/de not_active IP Right Cessation
- 1984-07-25 EP EP84108822A patent/EP0132845B1/en not_active Expired
- 1984-07-25 DE DE8484108822T patent/DE3470420D1/de not_active Expired
- 1984-07-26 DK DK365184A patent/DK160276C/da active
- 1984-07-26 YU YU1325/84A patent/YU43371B/xx unknown
- 1984-07-26 HU HU842875A patent/HU194561B/hu not_active IP Right Cessation
- 1984-07-26 SU SU843773894A patent/SU1482527A3/ru active
- 1984-07-26 ES ES534624A patent/ES8603501A1/es not_active Expired
- 1984-07-26 KR KR1019840004455A patent/KR900006750B1/ko not_active IP Right Cessation
- 1984-07-26 DD DD84265685A patent/DD228256A5/de not_active IP Right Cessation
- 1984-07-26 FI FI842987A patent/FI77862C/fi not_active IP Right Cessation
- 1984-07-27 PH PH31045A patent/PH21696A/en unknown
-
1985
- 1985-04-29 SU SU853885803A patent/SU1445558A3/ru active
- 1985-07-16 ES ES545250A patent/ES8607287A1/es not_active Expired
-
1986
- 1986-07-16 YU YU1266/86A patent/YU43702B/xx unknown
- 1986-07-16 YU YU1267/86A patent/YU43703B/xx unknown
Also Published As
Publication number | Publication date |
---|---|
KR900006750B1 (ko) | 1990-09-20 |
DK160276B (da) | 1991-02-18 |
AU3091084A (en) | 1985-01-31 |
DK160276C (da) | 1991-07-22 |
HUT34976A (en) | 1985-05-28 |
EP0132845A3 (en) | 1985-09-11 |
FI842987A0 (fi) | 1984-07-26 |
FI842987A (fi) | 1985-01-28 |
YU126786A (en) | 1987-10-31 |
SU1445558A3 (ru) | 1988-12-15 |
ES534624A0 (es) | 1985-12-16 |
ES8607287A1 (es) | 1986-05-16 |
ES8603501A1 (es) | 1985-12-16 |
DD228256A5 (de) | 1985-10-09 |
HU194561B (en) | 1988-02-29 |
CS274601B2 (en) | 1991-09-15 |
YU43702B (en) | 1989-10-31 |
PH21696A (en) | 1988-01-13 |
DK365184D0 (da) | 1984-07-26 |
ATE33494T1 (de) | 1988-04-15 |
DE3470420D1 (en) | 1988-05-19 |
DK365184A (da) | 1985-01-28 |
CS557584A2 (en) | 1990-11-14 |
ES545250A0 (es) | 1986-05-16 |
EP0132845B1 (en) | 1988-04-13 |
YU132584A (en) | 1986-12-31 |
FI77862C (fi) | 1989-05-10 |
YU43371B (en) | 1989-06-30 |
FI77862B (fi) | 1989-01-31 |
AU565898B2 (en) | 1987-10-01 |
YU126686A (en) | 1987-12-31 |
US4649144A (en) | 1987-03-10 |
SU1482527A3 (ru) | 1989-05-23 |
EP0132845A2 (en) | 1985-02-13 |
YU43703B (en) | 1989-10-31 |
CA1327580C (en) | 1994-03-08 |
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