KR830007643A - 벤조헤테로사이클 화합물의 제조방법 - Google Patents
벤조헤테로사이클 화합물의 제조방법 Download PDFInfo
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- KR830007643A KR830007643A KR1019810004344A KR810004344A KR830007643A KR 830007643 A KR830007643 A KR 830007643A KR 1019810004344 A KR1019810004344 A KR 1019810004344A KR 810004344 A KR810004344 A KR 810004344A KR 830007643 A KR830007643 A KR 830007643A
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- Prior art keywords
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- lower alkyl
- substituted
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- 150000001875 compounds Chemical class 0.000 title claims 10
- 238000000034 method Methods 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- -1 1, 2, 5, 6-tetrahydro-1-pyridyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 2
- 231100000331 toxic Toxicity 0.000 claims 2
- 230000002588 toxic effect Effects 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
-
- 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
-
- 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
- C07D471/06—Peri-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 다음 일반식(Ⅱ)의 화합물을 다음 일반식(Ⅲ)의 화합물과 반응시킴을 특징으로 하는 다음 일반식(Ⅰ)의 화합물 또는이의 약학적으로 무독한 염의 제조방법.상기 일반식에서R1는 수소원자 또는 저급알킬그룹이고R2는 수소원자 또는 할로겐원자이고R3는 하이드록시메틸그룹으로 치환될 수 있는 1-피롤리디닐그룸, 1, 2, 5, 6-테트라하이드로-1-피리딜그룹, 옥소그룹 또는 저급할로알킬그룹으로 치환된 1-피페라지닐그룹 또는 다음 일반식의 그룹이고(여기에서 R4는 수소원자, 저급알킬그룹, 저급알콕그룹, 하이드록시그룹, 페닐-저급알킬그룹, 저급알카노일옥시그룹, 저급알킬그룹 또는 저급알카노일그룹으로 치환될 수 있는 아미노그룹, 옥소그룹 또는 카바모일그룹이고,Z는 산소원자, 황원자 또는 메틸그룹이고,m은 1 또는 2이다).n은 1 또는 2의 정수이고,단 n이 2인 경우,R3는 저급할로알킬그룹으로 치환된 1-피페라지닐그룹이 될 수 없으며,X1은 할로겐원자, 저급알칸설포닐옥시그룹 또는 아릴설포닐옥시그룹이다.
- 다음 일반식 (Ⅴ)의 화합물을 다음 일반식(Ⅵ)의 화합물 또는 다음 일반식Ⅶ)의 화합물과 반응시킨다음 생성된 화합물을 폐환시키고 임의로 가수분해함을 특징으로 하는 다음 일반식(Ⅰ)의 화합물 또는 이의 약학적으로 무독한 염의 제조방법.상기 일반식에서R1은 수소원자 또는 저급알킬그룹이고R2는 수소원자 또는 할로겐원자이고R3는 하이드록시메틸그룹으로 치환될 수 있는 1-피롤리디닐그룹, 1,2,5,6-테트라하이드로-1-피리딜 그룹, 옥소그룹 또는 저급할로알킬그룹으로 치환된 1-피페라지닐그룹 또는 다음 일반식의 그룹이고(여기에 R4는 수소원자, 저급알킬그룹, 저급알콕시그룹, 하이드록시 그룹, 페닐-저급알킬그룹, 저급알카노일옥시그룹, 저급알킬그룹 또는 저급 알킬노일그룹으로 치환될 수 있는 아미노그룹, 옥소그룹 또는 카바모일 그룹이고, Z는 산소원자, 황원자 또는 메틸렌그룹이고 m은 1 또는 2이다).n은 1 또는 2의 정수이고단 n이 2인 경우,R3는 저급할로알킬그룹으로 치환된 1-피페라지닐그룹이 될 수 없으며,R6, R7및 R8은 각기 저급알킬그룹이고R9및 R10은 각기 저급알킬그룹이다.
- 다음 일반식(Ⅰb)의 화합물을 가수분해시킴을 특징으로 하는 다음 일반식(Ⅰ)화합물 또는 이의 약학적으로 무독한 염의 제조방법.상기 일반식에서R1은 수소원자 또는 저급알킬그룹이고R2는 수소원자 또는 할로겐원자이고R3는 하이드록시메틸그룹으로 치환될 수 있는 1-피롤리디닐그룹, 1,2,5,6-테트라하이드로-1-피리딜그룹, 옥소그룹 또는 저급할로알킬그룹으로 치환된 1-피페라지닐그룹 또는 다음 일반식의 그룹이고,(여기에서 R4는 수소원자, 저급알킬그룹, 저급알콕시그룹, 하이드록시 그룹, 페닐-저급알킬그룹, 저급알카노일옥시그룹, 저급알킬그룹 또는 저급 알킬노일그룹으로 치환될 수 있는 아미노그룹, 옥소그룹 또는 카바모일 그룹이고, Z는 산소원자, 황원자 또는 메틸렌그룹이고 m은 1 또는 2이다).n은 1 또는 2의 정수이고단 n이 2인 경우,R3는 저급할로알킬그룹으로 치환된 1-피페라지닐그룹이 될 수 없으며R11및 R12는 각기 수소원자 또는 저급알킬그룹이고Y는 함유된 3급 질소원자를 통해 결합되어 있는 방향족 헤테로사이클환 또는 트리알킬아민그룹이고Z는 음이온성 이온이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP158652 | 1980-11-10 | ||
JP55158652A JPS5781486A (en) | 1980-11-10 | 1980-11-10 | Benzo(ij)quinolidine-2-carboxylic acid derivative |
JP63170 | 1981-04-24 | ||
JP56063170A JPS57176987A (en) | 1981-04-24 | 1981-04-24 | Pyrrolo(3,2,1-ij)quinoline-5-carboxylic acid derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830007643A true KR830007643A (ko) | 1983-11-04 |
KR880001625B1 KR880001625B1 (ko) | 1988-09-02 |
Family
ID=26404260
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019810004344A KR880001625B1 (ko) | 1980-11-10 | 1981-11-10 | 벤조헤테로사이클 화합물의 제조방법 |
Country Status (19)
Country | Link |
---|---|
US (2) | US4399134A (ko) |
KR (1) | KR880001625B1 (ko) |
AT (2) | AT395150B (ko) |
AU (1) | AU546358B2 (ko) |
CA (1) | CA1179341A (ko) |
CH (1) | CH648845A5 (ko) |
DE (2) | DE10075035I2 (ko) |
DK (1) | DK160940C (ko) |
ES (2) | ES507493A0 (ko) |
FI (1) | FI71141C (ko) |
FR (1) | FR2493849A1 (ko) |
GB (1) | GB2086905B (ko) |
IT (1) | IT1171646B (ko) |
NL (1) | NL193457C (ko) |
NO (1) | NO156828C (ko) |
PH (1) | PH16685A (ko) |
PT (1) | PT73957B (ko) |
SE (1) | SE448542B (ko) |
SU (2) | SU1366055A3 (ko) |
Families Citing this family (44)
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NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
US4380543A (en) * | 1981-11-06 | 1983-04-19 | Riker Laboratories, Inc. | Antimicrobial 8-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acids |
PH22140A (en) * | 1982-06-29 | 1988-06-01 | Daiichi Seiyaku Co | Tricyclic compounds |
US4443447A (en) * | 1982-10-25 | 1984-04-17 | Riker Laboratories, Inc. | Phenyl-substituted tricyclic antibacterial agents |
JPS5978189A (ja) * | 1982-10-26 | 1984-05-04 | Otsuka Pharmaceut Co Ltd | ピロロ〔3,2,1−ij〕キノリン−5−カルボン酸誘導体 |
US4472406A (en) * | 1982-11-12 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 6,7-dihydro-8-(imidazol-1-yl)-5-methyl-1-oxo-1H,5H-benzo [ij]quinolizine-2-carboxylic acids and derivatives |
JPS59137482A (ja) * | 1983-01-26 | 1984-08-07 | Otsuka Pharmaceut Co Ltd | ピロロ〔3,2,1,−ij〕キノリン−5−カルボン酸誘導体 |
JPS59155381A (ja) * | 1983-02-22 | 1984-09-04 | Kyorin Pharmaceut Co Ltd | ベンゾキノリジンカルボン酸誘導体及びその製造法 |
US4473568A (en) * | 1983-03-01 | 1984-09-25 | Warner Lambert Company | Antibacterial thiazolidine or thiomorpholine substituted quinolines |
US4472407A (en) * | 1983-03-17 | 1984-09-18 | Riker Laboratories, Inc. | Antimicrobial 8-alkoxy-6,7-dihydro-5-methyl-9-fluoro-1-oxo-1H,5H-benzo[ij]qu |
US4562195A (en) * | 1984-02-02 | 1985-12-31 | Warner-Lambert Company | Reversing amnesia with saturated tricyclic nitrogen-containing diones |
US4571396A (en) * | 1984-04-16 | 1986-02-18 | Warner-Lambert Company | Antibacterial agents |
US4550103A (en) * | 1984-07-20 | 1985-10-29 | Warner-Lambert Company | Antibacterial 1-oxo-benzoquinolizine-2-carboxylic acids |
AU585981B2 (en) * | 1985-05-24 | 1989-06-29 | Tokyo Tanabe Company Limited | Benzo (IJ) quinolizine-2-carboxylic acid derivatives, the salts and their hydrates, pharmaceutical compositions thereof, and processes for preparing the same |
US5210193A (en) * | 1986-01-17 | 1993-05-11 | American Cyanamid Company | Piperazine derivatives |
US4940710A (en) * | 1986-01-17 | 1990-07-10 | American Cyanamid Company | 7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
US4948894A (en) * | 1989-02-21 | 1990-08-14 | American Cyanamid Company | 8-fluoro and 7, 8, 10-trifluoro-9-(substituted)-6-oxo-6H-benzo-(C)quinolizine-5-carboxylic acids |
KR900014383A (ko) * | 1989-03-29 | 1990-10-23 | 원본미기재 | 피롤로퀴놀린 유도체, 이의 제조방법 및 이를 사용한 항균제 |
US6034100A (en) * | 1993-03-10 | 2000-03-07 | Otsuka Pharmaceutical Co., Ltd. | Method for inhibiting cytokine secretion |
ATE186642T1 (de) * | 1993-03-10 | 1999-12-15 | Otsuka Pharma Co Ltd | Interleukin-1 inhibitor |
EP0908181B8 (en) * | 1996-05-20 | 2009-04-15 | Otsuka Pharmaceutical Co., Ltd. | Remedy for rosacea |
DE19718065A1 (de) * | 1997-04-29 | 1998-11-05 | Henkel Kgaa | Reinigungsmittel für nachvernetzende Polyurethan-Hotmelts |
US6750224B1 (en) | 1999-05-07 | 2004-06-15 | Wockhardt Limited | Antibacterial optically pure benzoquinolizine carboxylic acids, processes, compositions and methods of treatment |
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US6514986B2 (en) | 2000-11-22 | 2003-02-04 | Wockhardt Limited | Chiral fluoroquinolone arginine salt forms |
DE19962470A1 (de) * | 1999-12-22 | 2001-07-12 | Schulz Hans Herrmann | Verwendung von Chemotherapeutika |
AU7866701A (en) * | 2000-05-08 | 2001-11-20 | Shiv Kumar Agarwal | Antibacterial chiral 8-(substituted piperidino)-benzo (i, j) quinolizines, processes, compositions and methods of treatment |
WO2001085095A2 (en) * | 2000-05-08 | 2001-11-15 | Wockhardt Limited | Chiral fluoroquinolizinone arginine salt forms |
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EP1453824A1 (en) * | 2001-12-13 | 2004-09-08 | Wockhardt Limited | New generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
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EP1918289A3 (en) | 2002-05-28 | 2009-08-19 | Wockhardt Limited | Crystalline nadifloxacin arginine salt form |
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AU2003303367A1 (en) * | 2002-12-31 | 2004-07-22 | Noel J. De Souza | Compositions of benzoquinolizine carboxylic acid antibiotic drugs |
WO2005023805A1 (en) | 2003-09-04 | 2005-03-17 | Wockhardt Limited | Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate |
DK1954697T3 (da) * | 2005-10-21 | 2010-06-14 | Glaxo Group Ltd | Peri-kondenserede tricykliske forbindelser, der er anvendelige som antibakterielle midler |
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BE793524A (fr) * | 1971-12-30 | 1973-06-29 | Riker Laboratories Inc | Acides benzoquinolizine-carboxyliques et leurs derives |
US4001243A (en) * | 1972-11-02 | 1977-01-04 | Riker Laboratories, Inc. | Substituted benzo(ij)quinolizine-2-carboxylic acids and derivatives thereof |
US3917609A (en) * | 1973-06-27 | 1975-11-04 | Minnesota Mining & Mfg | Pyrroloquinoline carboxylic acids and derivatives |
DE2953974C2 (ko) * | 1978-04-12 | 1992-06-25 | Otsuka Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp | |
US4416884A (en) * | 1978-04-12 | 1983-11-22 | Otsuka Pharmaceutical Co., Ltd. | Piperazinylbenzoheterocyclic compounds |
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 |
JPS5540616A (en) * | 1978-09-14 | 1980-03-22 | Otsuka Pharmaceut Co Ltd | Preparation of benzo-hetero-compound |
JPS5630964A (en) * | 1979-08-22 | 1981-03-28 | Kyorin Pharmaceut Co Ltd | Novel substituted quinolinecarboxylic acid and its preparation |
JPS55149284A (en) * | 1980-05-02 | 1980-11-20 | Otsuka Pharmaceut Co Ltd | Piperazinylbenzo heterocyclic derivative |
NO156828C (no) * | 1980-11-10 | 1987-12-02 | Otsuka Pharma Co Ltd | Analogifremgangsm te for fremstilling av antibakterielt virksomme benzoheterocykliske forbindelser. |
AT380250B (de) * | 1980-12-18 | 1986-04-25 | Otsuka Pharma Co Ltd | Verfahren zur herstellung benzoheterocyclischer verbindungen |
-
1981
- 1981-11-04 NO NO813726A patent/NO156828C/no not_active IP Right Cessation
- 1981-11-05 AT AT0474881A patent/AT395150B/de not_active IP Right Cessation
- 1981-11-09 SE SE8106642A patent/SE448542B/sv unknown
- 1981-11-09 SU SU813354800A patent/SU1366055A3/ru active
- 1981-11-09 DE DE2000175035 patent/DE10075035I2/de active Active
- 1981-11-09 DK DK495281A patent/DK160940C/da not_active IP Right Cessation
- 1981-11-09 FI FI813526A patent/FI71141C/fi not_active IP Right Cessation
- 1981-11-09 DE DE19813144455 patent/DE3144455A1/de active Granted
- 1981-11-09 PT PT73957A patent/PT73957B/pt unknown
- 1981-11-09 IT IT49656/81A patent/IT1171646B/it active
- 1981-11-10 NL NL8105075A patent/NL193457C/nl not_active IP Right Cessation
- 1981-11-10 ES ES507493A patent/ES507493A0/es active Granted
- 1981-11-10 GB GB8133890A patent/GB2086905B/en not_active Expired
- 1981-11-10 FR FR8121100A patent/FR2493849A1/fr active Granted
- 1981-11-10 US US06/320,027 patent/US4399134A/en not_active Expired - Lifetime
- 1981-11-10 KR KR1019810004344A patent/KR880001625B1/ko active
- 1981-11-10 AU AU77335/81A patent/AU546358B2/en not_active Expired
- 1981-11-10 PH PH26477A patent/PH16685A/en unknown
- 1981-11-10 CH CH7200/81A patent/CH648845A5/de not_active IP Right Cessation
- 1981-11-10 CA CA000389769A patent/CA1179341A/en not_active Expired
-
1982
- 1982-10-15 ES ES516523A patent/ES8401035A1/es not_active Expired
- 1982-12-27 SU SU823527501A patent/SU1277896A3/ru active
-
1983
- 1983-05-25 US US06/497,914 patent/US4552879A/en not_active Expired - Lifetime
-
1989
- 1989-12-20 AT AT2887/89A patent/AT393383B/de not_active IP Right Cessation
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