KR840005813A - 5,8-디하이드로-8-옥소-1,3-디옥솔로(4,5-g)퀴놀린-7-카복실산류의 제조방법 - Google Patents
5,8-디하이드로-8-옥소-1,3-디옥솔로(4,5-g)퀴놀린-7-카복실산류의 제조방법 Download PDFInfo
- Publication number
- KR840005813A KR840005813A KR1019830003631A KR830003631A KR840005813A KR 840005813 A KR840005813 A KR 840005813A KR 1019830003631 A KR1019830003631 A KR 1019830003631A KR 830003631 A KR830003631 A KR 830003631A KR 840005813 A KR840005813 A KR 840005813A
- Authority
- KR
- South Korea
- Prior art keywords
- hydrogen
- compound
- formula
- alkyl
- alkali metal
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 3
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical class C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- -1 alkali metal salts Chemical class 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000002585 base Substances 0.000 claims 3
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 1
- ILLFAGPCJNJIBX-UHFFFAOYSA-N ethyl 5-[(2-methoxy-2-oxoethyl)amino]-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(NCC(=O)OC)C2=CC2=C1OCO2 ILLFAGPCJNJIBX-UHFFFAOYSA-N 0.000 claims 1
- GYTQBNQDCNZROL-UHFFFAOYSA-N ethyl 5-amino-8-oxo-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CN(N)C2=CC2=C1OCO2 GYTQBNQDCNZROL-UHFFFAOYSA-N 0.000 claims 1
- VZKWWMFVWHSLHK-UHFFFAOYSA-N ethyl 8-oxo-5h-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate Chemical compound C1=C2C(=O)C(C(=O)OCC)=CNC2=CC2=C1OCO2 VZKWWMFVWHSLHK-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (4)
- R"가 수소 또는 저급알킬인 하기구조식(Ⅶ)의 화합물을 아민화제로 처리하여 R과 R'가 각기 수소인 화합물을 제조한 다음 소망에 따라 R과 R가 각시 수소인 구조식(Ⅰ)의 화합물을 포르밀화시켜 R'가 포르밀이고 R"가 수소인 구조식(Ⅰ)의 화합물을 제조하고;소망에 따라 R'가 포르밀 또는 수소인 구조식(Ⅰ)의 화합물은 R'가 포르밀인 경우 염기존재하여 R'가 수소인 경우 알칼리금속 탄산염 존재하여 C1-3의 알킬할라이드로 알킬화하여 R"가 저급알킬이며 R이 C1-3알킬이고 R'가 포르밀 또는 알콕시카보닐인 구조식(Ⅰ)의 화합물을 얻고;소망에 따라 구조식(Ⅰ)의 화합물을 1몰당량 또는 그 이상의 알칼리금속염기로 가수분해시켜 R'가 수소인 구조식(Ⅰ)의 화합물을 제조하여 이때 알칼리금속염기가 2당량 이상으로 사용된 경우엔 가수분해에 의해 화합물의 알칼리금속염이 생성되며;소망에 따라 알칼리금속염을 유리염기(R"=수소)로 전환시키고;소망에 따라 R"가 저급알킬인 구조식(Ⅰ)화합물을 R"가 수소인 상응하는 화합물로 전환시키고;소망에 따라 R과 R'가 모두 수소인 구조식(Ⅰ)의 화합물을 디알킬설페이트와 반응시켜 R과 R'가 C1-3알킬인 상응하는 화합물을 얻고;소망에 따라 R"가 수소인 구조식 (Ⅰ)의 화합물을 그의 알칼리금속염이나 아민염으로 전환시킴을 특징으로 하는 하기 구조식(Ⅰ)의 화합물 또는 R"가 수소인 화합물의 알칼리 금속염 또는 아민염을 제조하는 방법.상기식들에서 R은 수소, C1-3알킬이며;R'는 수소, 포리밀,C1-3알킬 또는 알콕시카보닐(여기서 알킬기는 R과 동일함)이며;R"는 수소 또는 저급알킬이다.
- 제 1항에 있어서, R'와 R"가 수소임을 특징으로하는 방법.
- 제2항에 있어서, 에틸 8―하이드록시―1,3―디옥솔로[4,5―g]퀴놀린―7―카복실레이트를 0―(2,4―디니트로페닐)하이드록실아민과 반응시키고 결과 생선된 에틸 5―아미노―5,8―디하이드로―8―옥소―1,3―디옥솔로[4,5―g]퀴놀린 ―7―카복실레이트를 탄산칼륨 존재하에 요드화메틸과 반응시킨 다음 결과 생성된 에틸 5,8―디하이드로―5―[(메톡시카보닐)메틸아미노]―8―옥소―1,3―디옥솔로[4,5―g]퀴놀린―7―카복실레이트를 알칼리금속염기로 가수분해시킴을 특징으로하는 5,8―디하이드로―5―(메틸아미노―8―옥소―1,3―디옥솔로―[4,5―g]퀴놀린―7―카복실산의 제조방법.
- 제1항에 있어서 R이 메틸 또는 에틸이며 R'와 R"가 수소인 화합물을 제외한 구조식(Ⅰ)의 화합물을 특징으로하는 화학 중간체.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/405,263 US4439436A (en) | 1982-08-04 | 1982-08-04 | 1,3-Dioxolo(4,5-G)quinoline compounds |
| US405263 | 1982-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR840005813A true KR840005813A (ko) | 1984-11-19 |
Family
ID=23602957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830003631A KR840005813A (ko) | 1982-08-04 | 1983-08-03 | 5,8-디하이드로-8-옥소-1,3-디옥솔로(4,5-g)퀴놀린-7-카복실산류의 제조방법 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4439436A (ko) |
| EP (1) | EP0101951A1 (ko) |
| JP (1) | JPS5946283A (ko) |
| KR (1) | KR840005813A (ko) |
| AU (1) | AU1689683A (ko) |
| CA (1) | CA1218659A (ko) |
| DK (1) | DK353983A (ko) |
| FI (1) | FI832780L (ko) |
| GR (1) | GR78962B (ko) |
| IL (1) | IL69267A0 (ko) |
| NO (1) | NO832810L (ko) |
| NZ (1) | NZ204900A (ko) |
| PH (1) | PH19689A (ko) |
| PT (1) | PT77133B (ko) |
| ZA (1) | ZA835239B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4730000A (en) * | 1984-04-09 | 1988-03-08 | Abbott Laboratories | Quinoline antibacterial compounds |
| US4774246A (en) * | 1984-01-26 | 1988-09-27 | Abbott Laboratories | Quinoline antibacterial compounds |
| US4607032A (en) * | 1984-04-26 | 1986-08-19 | Abbott Laboratories | Quino-benoxazine antibacterial compounds |
| US4528285A (en) * | 1984-04-26 | 1985-07-09 | Abbott Laboratories | Methylenedioxy quino-benzothiazine derivatives |
| US4542133A (en) * | 1984-04-26 | 1985-09-17 | Abbott Laboratories | Methylenedioxy quino-benoxazine derivatives and antibacterial use |
| US4687770A (en) * | 1985-12-23 | 1987-08-18 | Abbott Laboratories | Isoxazolo-pyrido-benzoxazine and isothiazolo-pyrido-benzoxazine derivatives |
| US4689325A (en) * | 1985-12-23 | 1987-08-25 | Abbott Laboratories | Isoxazolo-pyrido-phenoxazine and isothiazolo-pyrido-phenoxazine derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1076828A (en) * | 1963-12-12 | 1967-07-26 | Warner Lambert Pharmaceutical | Methylenedioxy quinoline derivatives |
| DE2103805C3 (de) * | 1970-01-28 | 1980-03-20 | Sumitomo Chemical Co., Ltd., Osaka (Japan) | Verfahren zur Herstellung von N-substituierten 6,7-Methylendioxy-4chinolonen |
| GB1338961A (en) * | 1970-07-09 | 1973-11-28 | Sumitomo Chemical Co | Alkylenedioxy quinoline-3-carboxylic acid derivatives |
| DE2808070A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Verfahren zur herstellung von 4-pyridon-3-carbonsaeuren und/oder deren derivaten |
-
1982
- 1982-08-04 US US06/405,263 patent/US4439436A/en not_active Expired - Fee Related
-
1983
- 1983-07-14 NZ NZ204900A patent/NZ204900A/en unknown
- 1983-07-15 AU AU16896/83A patent/AU1689683A/en not_active Abandoned
- 1983-07-18 IL IL69267A patent/IL69267A0/xx unknown
- 1983-07-19 ZA ZA835239A patent/ZA835239B/xx unknown
- 1983-07-20 PH PH29257A patent/PH19689A/en unknown
- 1983-07-28 GR GR72072A patent/GR78962B/el unknown
- 1983-07-28 EP EP83107464A patent/EP0101951A1/en not_active Withdrawn
- 1983-07-29 PT PT77133A patent/PT77133B/pt unknown
- 1983-08-02 FI FI832780A patent/FI832780L/fi not_active Application Discontinuation
- 1983-08-03 KR KR1019830003631A patent/KR840005813A/ko not_active Application Discontinuation
- 1983-08-03 CA CA000433752A patent/CA1218659A/en not_active Expired
- 1983-08-03 DK DK353983A patent/DK353983A/da not_active Application Discontinuation
- 1983-08-03 NO NO832810A patent/NO832810L/no unknown
- 1983-08-04 JP JP58143086A patent/JPS5946283A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1218659A (en) | 1987-03-03 |
| DK353983D0 (da) | 1983-08-03 |
| FI832780L (fi) | 1984-02-05 |
| GR78962B (ko) | 1984-10-02 |
| FI832780A0 (fi) | 1983-08-02 |
| NO832810L (no) | 1984-02-06 |
| US4439436A (en) | 1984-03-27 |
| PT77133A (fr) | 1983-08-01 |
| PH19689A (en) | 1986-06-13 |
| JPS5946283A (ja) | 1984-03-15 |
| AU1689683A (en) | 1984-02-09 |
| IL69267A0 (en) | 1983-11-30 |
| EP0101951A1 (en) | 1984-03-07 |
| DK353983A (da) | 1984-02-05 |
| PT77133B (fr) | 1986-01-24 |
| ZA835239B (en) | 1984-03-28 |
| NZ204900A (en) | 1986-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19830803 |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |