KR960004339A - 신규한 퀴놀린계 화합물 및 그 의 제조방법 - Google Patents
신규한 퀴놀린계 화합물 및 그 의 제조방법 Download PDFInfo
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- KR960004339A KR960004339A KR1019950018354A KR19950018354A KR960004339A KR 960004339 A KR960004339 A KR 960004339A KR 1019950018354 A KR1019950018354 A KR 1019950018354A KR 19950018354 A KR19950018354 A KR 19950018354A KR 960004339 A KR960004339 A KR 960004339A
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- South Korea
- Prior art keywords
- fluoro
- salts
- oxo
- hexane
- carboxylic acid
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- 238000002360 preparation method Methods 0.000 title 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 15
- 239000001257 hydrogen Substances 0.000 claims abstract 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 9
- -1 amine compound Chemical class 0.000 claims abstract 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 6
- 150000002148 esters Chemical class 0.000 claims abstract 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 9
- DAIMPYBUNUXOFI-HQIWOYNQSA-N 7-(3,6-diazabicyclo[3.1.0]hexan-3-yl)-6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC4NC4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F DAIMPYBUNUXOFI-HQIWOYNQSA-N 0.000 claims 2
- JDTZMKNRFOGBBY-HQIWOYNQSA-N 8-chloro-7-(3,6-diazabicyclo[3.1.0]hexan-3-yl)-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CC4NC4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F JDTZMKNRFOGBBY-HQIWOYNQSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- WENDYCBFEXWSRV-DFAZKQQPSA-N 5-amino-7-(3,6-diazabicyclo[3.1.0]hexan-3-yl)-6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(=O)C=2C(N)=C(F)C(N3CC4NC4C3)=C(F)C=2N1[C@@H]1C[C@@H]1F WENDYCBFEXWSRV-DFAZKQQPSA-N 0.000 claims 1
- UAIWRNVZRHVKEX-KXQYZNHLSA-N 6,8-difluoro-1-[(1r,2s)-2-fluorocyclopropyl]-7-(6-methyl-3,6-diazabicyclo[3.1.0]hexan-3-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C2N(C)C2CN1C(C=1F)=C(F)C=C(C(C(C(O)=O)=C2)=O)C=1N2[C@@H]1C[C@@H]1F UAIWRNVZRHVKEX-KXQYZNHLSA-N 0.000 claims 1
- JTVVSZHWABAMAA-ZIULKBFBSA-N 7-(3,6-diazabicyclo[3.1.0]hexan-3-yl)-6-fluoro-1-[(1r,2s)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CC4NC4C3)=C(F)C=C2C(=O)C(C(=O)O)=CN1[C@@H]1C[C@@H]1F JTVVSZHWABAMAA-ZIULKBFBSA-N 0.000 claims 1
- ALFMRXKYXXVISS-NVYBKMQVSA-N 8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-7-(1-methyl-3,6-diazabicyclo[3.1.0]hexan-3-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N2)C2(C)CN1C(C=1Cl)=C(F)C=C(C(C(C(O)=O)=C2)=O)C=1N2[C@@H]1C[C@@H]1F ALFMRXKYXXVISS-NVYBKMQVSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
Classifications
-
- 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
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
본 발명은 종래의 퀴놀린계 항생제에 비해 뛰어난 항균 활성을 갖는 하기 일반식(Ⅰ)의 신규한 퀴놀린계 화합물 및 약제학적으로 허용되는 그의 염에 관한 것이다.
상기 식에서, R1은 수소 또는 에스테르 형성 그룹이고, R2는 수소, 아미노, 저급알킬아미노, 하이드록시, 저급알콕시, 머캅토, 저급알킬티오 또는 할로겐이며, Z는 하기 일반식의 아민 화합물이고
(여기서, R3는 수소 또는 저급알킬을 나타내고, R4및 R5는 각각 동일하거나 상이하며 수소 또는 C1-C2알킬을 나타낸다), X는 N 또는 C-C6이다(여기서, R6은 수소, 할로겐, 하이드록시, 메틸, 시아노, 니트로, 또는 메톡시를 나타낸다).
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기 일반식(Ⅰ)의 퀴놀계 화합물 및 약제학적으로 허용되는 그의 염.상기 식에서, R1은 수소 또는 에스테르 형성 그룹이고, R2는 수소, 아미노, 저급알킬아미노, 하이드록시, 저급알콕시, 머캅토, 저급알킬티오 또는 할로겐이며, Z는 하기 일반식의 아민 화합물이고(여기서, R3는 수소 또는 저급알킬을 나타내고, R4및 R5는 각각 동일하거나 상이하며 수소 또는 C1-C2알킬을 나타낸다), X는 N 또는 C-C6이다(여기서, R6은 수소, 할로겐, 하이드록시, 메틸, 시아노, 니트로, 또는 메톡시를 나타낸다).
- 제1항에 있어서, R1은 수소이고, R2는 수소 또는 아미노이며, Z는 하기 일반식의 아민 화합물이고(여기서, R3는 수소 또는 저급알킬을 나타내고, R4및 R5는 각각 동일하거나 상이하며 수소 또는 C1-C2알킬을 나타낸다), X는 N 또는 C-C6(여기서, R6은 수소, 메톡시 또는 할로겐을 나타낸다).
- 제2항에 있어서, (1) 6,8-디플루오르-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-7-(6-메틸-3,6-디아자비사이클로[3,1,0]헥산-3-일)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (2) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (3) 6,8-디플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-7-(1-메틸-3,6-디아자비사일클로[3,1,0]헥산-3-일)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (4) 5-아미노-7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (5) 8-클로로-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-7-(1-메틸-3,6-디아자비사이클로[3,1,0]헥산-3-일)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (6) 8-클로로-7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (7) 8-클로로-7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-(시스-2-플루오로-1-사이클로프로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (8) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-(시스-2-플루오로-1-사이클로프로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (9) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-(시스-2-플루오로-1-사이클로프로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (10) 5-아미노-7-(3,6-디아자비비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-(시스-2-플루오로-1-사이클로프로로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (11) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-8-메톡시-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (12) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-4-옥소-1,4-디하이드로-1,8-나프티리딘-3-카르복실산 및 그의 염인 화합물.
- 제1항에 있어서, 에스테르 형성 그룹이 저급알킬, C3-C7사이클로알킬 또는 벤질인 화합물.
- 제1항에 있어서, 약제학적으로 허용되는 염이 산부가염인 화합물.
- 제5항에 있어서, 산부가염이 젖산염, 메탄설폰산염, 염산염 중에서 선택된 1종인 화합물.
- 하기 일반식(Ⅱ)의 화합물 또는 그의 착화합물을 염기존재하에 하기 일반식(Ⅲ)의 화합물과 반응시킴을 특징으로 하여 하기 일반식(Ⅰ)의 화합물 및 약제학적으로 허용되는 그의 염을 제조하는 방법.상기 식에서, R2및 X는 제1항에 언급한 바와 같고, Y는 할로겐을 나타낸다.
- 내용 없음
- 내용 없음
- 활성 물질로서 제1항 내지 6항중 어느 한 항에 따른 화합물 또는 약제학적으로 허용되는 그의 염을 적어도 1종 이상 함유함을 특징으로 하는 항균제 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR19940015840 | 1994-07-02 | ||
| KR94-15840 | 1994-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR960004339A true KR960004339A (ko) | 1996-02-23 |
Family
ID=19387157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950018354A Ceased KR960004339A (ko) | 1994-07-02 | 1995-06-29 | 신규한 퀴놀린계 화합물 및 그 의 제조방법 |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR960004339A (ko) |
| WO (1) | WO1996001262A1 (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6875784B2 (en) * | 2002-10-09 | 2005-04-05 | Pharmacia & Upjohn Company | Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives |
| DE102004035203A1 (de) | 2004-07-21 | 2006-02-16 | Bayer Healthcare Ag | Substituierte Chinolone |
| DE102006005861A1 (de) | 2006-02-09 | 2007-08-23 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone III |
| US10231970B2 (en) | 2014-09-30 | 2019-03-19 | NV Heterocycles | Methods of producing heteropolycycles via bis-epoxidation |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0571400A1 (en) * | 1991-01-14 | 1993-12-01 | Hanmi Pharmaceutical Co.,Ltd. | Novel quinolone compounds and processes for preparation thereof |
| CA2112165C (en) * | 1992-12-25 | 2003-04-08 | Makoto Takemura | Bicyclic amine derivatives |
-
1995
- 1995-06-29 KR KR1019950018354A patent/KR960004339A/ko not_active Ceased
- 1995-06-30 WO PCT/KR1995/000084 patent/WO1996001262A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO1996001262A1 (en) | 1996-01-18 |
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