KR900007807A - 퀴놀론 카복실산 중간물질의 제조방법 - Google Patents
퀴놀론 카복실산 중간물질의 제조방법 Download PDFInfo
- Publication number
- KR900007807A KR900007807A KR1019890016870A KR890016870A KR900007807A KR 900007807 A KR900007807 A KR 900007807A KR 1019890016870 A KR1019890016870 A KR 1019890016870A KR 890016870 A KR890016870 A KR 890016870A KR 900007807 A KR900007807 A KR 900007807A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- chloro
- fluoro
- cyclopropyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 7
- -1 t-butylamino Chemical group 0.000 claims 7
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 239000005749 Copper compound Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 150000001880 copper compounds Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 159000000000 sodium salts Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
- C07C229/58—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of a six-membered aromatic ring, e.g. N-phenyl-anthranilic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/70—Monocarboxylic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 일반식(Ⅴ)의 화합물.상기식에서 R1은 수소 또는 C1-C4알킬이고, R2는 요오드, 사이클로프로필아미노, 페닐아미노, 4-플루오로페닐아미노, 2,4-디플루오로페닐아미노, 또는 t-부틸아미노이며, X는 플루오로 또는 클로로이고, 단 R2가 요오드인 경우 R1은 수소이다.
- 제1항에 있어서, R1이 수소이고 X가 플루오로임을 특징으로 하는 화합물.
- 제1항또는 2항에 있어서, R2가 요오드, 사이클로프로필아미노, 또는 2,4-디플루오로페닐아미노임을 특징으로 하는 화합물.
- 일반식(Ⅱ)의 화합물.상기식에서 R3는 에틸, t-부틸, 사이클로프로필, 페닐, 4-플루오로 페닐, 또는 2,4-디플루오로페닐이고, X는 플루오로 또는 클로로이다.
- 제4항에 있어서, X가 플루오로이고, R3가 사이클로프로필 또는 2,4-디플루오로페닐임을 특징으로 하는 화합물.
- 일반식(Ⅱ)의 화합물을 일반식(Ⅱ')의 화합물의 알칼리 금속염과 반응시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물을 제조하는 방법.HOCH=CH-COR4(Ⅱ')상기식에서 R3는 에틸, t-부틸, 사이클로프로필, 페닐, -플루오로페닐, 또는 2,4-디플루오로페닐이고, R4는 하이드록시, C1-C3알콕시, 아미노 또는 C1-C4알킬아미노이며, X는 플루오로 또는 클로로이다.
- 제6항에 있어서, X가 플루오로이고, R3가 사이클로프로필이며 알칼리 금속염이 나트륨염임을 특징으로 하는 방법.
- 일반식(Ⅲ)의 화합물을 일반식(Ⅲ)의 화합물과 반응시킴을 특징으로 하여, 일반식(Ⅱ)의 화합물을 제조하는 방법.R5R6C=O (Ⅲ')상기식에서 R3는 에틸, t-부틸, 사이클로프로필, 페닐, 4-플루오로페닐, 또는 2,4-디플루오로페닐이고, X는 플루오로 또는 클로로이며, R5및 R6는 둘다 클로로 또는 트리클로로메틸옥시이거나, R5는 클로로이고 R6는 C1-C5알콕시; 트리클로로 메틸옥시;페녹시;또는 할로, 니트로, C1-C6알킬, 또는 트리플루오로메틸로 치환된 페녹시이다.
- 제8항에 있어서, R5및 R6가 둘 다 트리클로로 메틸옥시 또는 클로로이거나 R5가 클로로이고 R6가 트리클로로메틸옥시이며; X가 플루오로이고 R3가 사이클로 프로필임을 특징으로 하는 방법.
- 일반식(Ⅵ)의 화합물을 일반식(Ⅳ')의 화합물과 구리 또는 구리 화합물의 존재하에서 반응시킴을 특징으로 하여, 일반식(Ⅲ)의 화합물을 제조하는 방법.R3NH2(Ⅳ')상기식에서 R3는 에틸, t-부틸, 사이클로프로필, 페닐, 4-플루오로페닐, 또는 2,4-디플루오로페닐이고, X는 플루오로 또는 클로로이며, Hal은 요오드, 브로모 또는 클로로이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019910014732A KR970011791B1 (ko) | 1988-11-23 | 1991-08-24 | 퀴놀론 카복실산 중간물질 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US275449 | 1988-11-23 | ||
| US275,449 | 1988-11-23 | ||
| US07/275,449 US4939290A (en) | 1988-11-23 | 1988-11-23 | Benzoic acid derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910014732A Division KR970011791B1 (ko) | 1988-11-23 | 1991-08-24 | 퀴놀론 카복실산 중간물질 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR900007807A true KR900007807A (ko) | 1990-06-02 |
| KR910008797B1 KR910008797B1 (ko) | 1991-10-21 |
Family
ID=23052333
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890016870A KR910008797B1 (ko) | 1988-11-23 | 1989-11-21 | 퀴놀론카복실산 중간물질의 제조방법 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4939290A (ko) |
| EP (1) | EP0370686B1 (ko) |
| JP (1) | JPH0639446B2 (ko) |
| KR (1) | KR910008797B1 (ko) |
| CN (1) | CN1022183C (ko) |
| AT (1) | ATE99283T1 (ko) |
| AU (2) | AU619361B2 (ko) |
| CA (1) | CA2003446A1 (ko) |
| DE (1) | DE68911879T2 (ko) |
| DK (1) | DK587089A (ko) |
| EG (1) | EG18943A (ko) |
| ES (1) | ES2062037T3 (ko) |
| FI (1) | FI91856C (ko) |
| HU (1) | HU208529B (ko) |
| IE (1) | IE61737B1 (ko) |
| MY (1) | MY105874A (ko) |
| NO (1) | NO176315C (ko) |
| NZ (1) | NZ231459A (ko) |
| PH (1) | PH27224A (ko) |
| PL (1) | PL162203B1 (ko) |
| PT (1) | PT92366B (ko) |
| YU (1) | YU47003B (ko) |
| ZA (1) | ZA898902B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4200512C2 (de) * | 1992-01-11 | 1994-09-15 | Riedel De Haen Ag | Verfahren zur Herstellung von Halogenanthranilsäuren und aromatische Bromverbindungen als Vorstufen |
| PE20011349A1 (es) | 2000-06-16 | 2002-01-19 | Upjohn Co | 1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales |
| CN103450107B (zh) * | 2013-09-13 | 2016-05-25 | 陕西嘉禾生物科技股份有限公司 | 一种n-甲基靛红酸酐的制备方法 |
| CN109053486B (zh) * | 2018-08-16 | 2022-12-30 | 江苏中旗科技股份有限公司 | 一种n-甲基-2-氟苯胺的合成方法 |
| CN112094586B (zh) * | 2020-09-22 | 2021-11-09 | 丹阳市精通眼镜技术创新服务中心有限公司 | 一种高耐磨性疏水涂层及其制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598823A (en) * | 1969-05-28 | 1971-08-10 | Sandoz Ag | Tricyclic quinazolinones |
| FR2436781A1 (fr) * | 1978-09-19 | 1980-04-18 | Berri Balzac | Derives d'amino-3 (1h,3h) quinazolinedione-2,4, leur procede de preparation et leurs applications en therapeutique |
| US4521616A (en) * | 1980-12-29 | 1985-06-04 | Occidental Chemical Corporation | Method for the preparation of fluoroanthranilic acids |
| DE3248507A1 (de) * | 1982-12-29 | 1984-07-05 | Bayer Ag, 5090 Leverkusen | Mikrobizide mittel auf chinoloncarbonsaeure basis |
| US4623650A (en) * | 1984-12-06 | 1986-11-18 | Pfizer Inc. | Antibiotic derivatives of 7-phenyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids |
-
1988
- 1988-11-23 US US07/275,449 patent/US4939290A/en not_active Expired - Lifetime
-
1989
- 1989-11-15 EP EP89311819A patent/EP0370686B1/en not_active Expired - Lifetime
- 1989-11-15 DE DE89311819T patent/DE68911879T2/de not_active Expired - Fee Related
- 1989-11-15 ES ES89311819T patent/ES2062037T3/es not_active Expired - Lifetime
- 1989-11-15 AT AT89311819T patent/ATE99283T1/de not_active IP Right Cessation
- 1989-11-20 MY MYPI89001612A patent/MY105874A/en unknown
- 1989-11-21 AU AU45382/89A patent/AU619361B2/en not_active Ceased
- 1989-11-21 CA CA002003446A patent/CA2003446A1/en not_active Abandoned
- 1989-11-21 PT PT92366A patent/PT92366B/pt active IP Right Grant
- 1989-11-21 HU HU896037A patent/HU208529B/hu not_active IP Right Cessation
- 1989-11-21 KR KR1019890016870A patent/KR910008797B1/ko not_active IP Right Cessation
- 1989-11-21 NZ NZ231459A patent/NZ231459A/xx unknown
- 1989-11-22 PL PL89282412A patent/PL162203B1/pl unknown
- 1989-11-22 IE IE372989A patent/IE61737B1/en not_active IP Right Cessation
- 1989-11-22 ZA ZA898902A patent/ZA898902B/xx unknown
- 1989-11-22 FI FI895571A patent/FI91856C/fi not_active IP Right Cessation
- 1989-11-22 EG EG57589A patent/EG18943A/xx active
- 1989-11-22 NO NO894642A patent/NO176315C/no not_active IP Right Cessation
- 1989-11-22 JP JP1304566A patent/JPH0639446B2/ja not_active Expired - Lifetime
- 1989-11-22 DK DK587089A patent/DK587089A/da not_active Application Discontinuation
- 1989-11-22 YU YU222089A patent/YU47003B/sh unknown
- 1989-11-22 CN CN89108800A patent/CN1022183C/zh not_active Expired - Fee Related
- 1989-11-23 PH PH39580A patent/PH27224A/en unknown
-
1992
- 1992-01-28 AU AU10508/92A patent/AU637944B2/en not_active Ceased
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