KR100763077B1 - 항균 퀴놀론 약제용으로 유용한 중간 물질로서의 알킬 3-시클로프로필아미노-2-[2,4-디브로모-3-(디플루오로메톡시)벤조일]-2-프로페노에이트의 원-포트 합성 방법 - Google Patents
항균 퀴놀론 약제용으로 유용한 중간 물질로서의 알킬 3-시클로프로필아미노-2-[2,4-디브로모-3-(디플루오로메톡시)벤조일]-2-프로페노에이트의 원-포트 합성 방법 Download PDFInfo
- Publication number
- KR100763077B1 KR100763077B1 KR1020027011757A KR20027011757A KR100763077B1 KR 100763077 B1 KR100763077 B1 KR 100763077B1 KR 1020027011757 A KR1020027011757 A KR 1020027011757A KR 20027011757 A KR20027011757 A KR 20027011757A KR 100763077 B1 KR100763077 B1 KR 100763077B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- alkyl
- difluoromethoxy
- dibromo
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- -1 alkyl 3-cyclopropylamino-2- [2,4-dibromo-3- (difluoromethoxy) benzoyl] -2-propenoate Chemical compound 0.000 title claims abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 3
- 238000005580 one pot reaction Methods 0.000 title abstract description 3
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000003814 drug Substances 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- MYABBCIHLRGMEC-UHFFFAOYSA-N 2,4-dibromo-3-(difluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(OC(F)F)=C1Br MYABBCIHLRGMEC-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 239000003759 ester based solvent Substances 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- ZQKWDZWSYRDSAS-UHFFFAOYSA-N 1,1-dichloroethane;methyl acetate Chemical compound CC(Cl)Cl.COC(C)=O ZQKWDZWSYRDSAS-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000011541 reaction mixture Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- DLUMWCMYRMIKEG-UHFFFAOYSA-N ethyl 3-(cyclopropylamino)-2-[2,4-dibromo-3-(difluoromethoxy)benzoyl]prop-2-enoate Chemical compound C=1C=C(Br)C(OC(F)F)=C(Br)C=1C(=O)C(C(=O)OCC)=CNC1CC1 DLUMWCMYRMIKEG-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- NJEMTUMNGXGTAZ-UHFFFAOYSA-N ethyl 3,3-bis(methylamino)prop-2-enoate Chemical compound CCOC(=O)C=C(NC)NC NJEMTUMNGXGTAZ-UHFFFAOYSA-N 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 0 *C=CN(*)* Chemical compound *C=CN(*)* 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- BWKAYBPLDRWMCJ-UHFFFAOYSA-N 1,1-diethoxy-n,n-dimethylmethanamine Chemical compound CCOC(N(C)C)OCC BWKAYBPLDRWMCJ-UHFFFAOYSA-N 0.000 description 1
- ANACNCZBPWZWIW-UHFFFAOYSA-N CCCNC=C(C(C(C=CC(Br)=C1OC(F)F)=C1Br)=O)C(O)=O Chemical compound CCCNC=C(C(C(C=CC(Br)=C1OC(F)F)=C1Br)=O)C(O)=O ANACNCZBPWZWIW-UHFFFAOYSA-N 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- SNRGJXWEFUNIJP-UHFFFAOYSA-N dichloromethane;methyl acetate Chemical compound ClCCl.COC(C)=O SNRGJXWEFUNIJP-UHFFFAOYSA-N 0.000 description 1
- OSIDOZXQKRNVGV-UHFFFAOYSA-N diethylamino prop-2-enoate Chemical compound CCN(CC)OC(=O)C=C OSIDOZXQKRNVGV-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- 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
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN196/DEL/2000 | 2000-03-07 | ||
| IN196DE2000 | 2000-03-07 | ||
| PCT/IB2001/000316 WO2001066512A1 (en) | 2000-03-07 | 2001-03-07 | One-pot synthesis of alkyl 3-cyclopropylamino-2-[2,4-dibromo-3-(difluoromethoxy)benzoyl]-2-propenoate as a useful intermediate for antibacterial quinolone medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20030017473A KR20030017473A (ko) | 2003-03-03 |
| KR100763077B1 true KR100763077B1 (ko) | 2007-10-04 |
Family
ID=11097039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020027011757A Expired - Lifetime KR100763077B1 (ko) | 2000-03-07 | 2001-03-07 | 항균 퀴놀론 약제용으로 유용한 중간 물질로서의 알킬 3-시클로프로필아미노-2-[2,4-디브로모-3-(디플루오로메톡시)벤조일]-2-프로페노에이트의 원-포트 합성 방법 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6835848B1 (enExample) |
| EP (1) | EP1278717B1 (enExample) |
| JP (1) | JP4751557B2 (enExample) |
| KR (1) | KR100763077B1 (enExample) |
| CN (1) | CN1202075C (enExample) |
| AT (1) | ATE364036T1 (enExample) |
| AU (1) | AU3590801A (enExample) |
| DE (1) | DE60128797D1 (enExample) |
| WO (1) | WO2001066512A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7759362B2 (en) * | 2004-04-21 | 2010-07-20 | Institut Of Medicinal Biotechnology Chinese Academy Of Medical Sciences | Quinolonecarboxylic acid compounds, preparation methods and pharmaceutical uses thereof |
| CN1244582C (zh) * | 2004-04-21 | 2006-03-08 | 中国医学科学院医药生物技术研究所 | 喹诺酮羧酸类化合物及其制备方法和医药用途 |
| KR200457934Y1 (ko) * | 2010-10-26 | 2012-01-12 | 주식회사 삼진엘앤디 | 등기구 마운팅 구조 |
| WO2013157018A1 (en) | 2012-04-18 | 2013-10-24 | Indian Institute Of Technology Madras | A process for the preparation of the core structure in quinolone and napthyridone class of antibiotics |
| CN105777631B (zh) * | 2016-04-18 | 2018-06-29 | 浙江中欣氟材股份有限公司 | 一种1-环丙基-4-氧代-7-溴-8-二氟甲氧基-1,4-二氢喹啉-3-羧酸乙酯的合成方法 |
| CN105801482B (zh) * | 2016-04-18 | 2018-06-22 | 浙江中欣氟材股份有限公司 | 一种1-环丙基-4-氧代-7-溴-8-二氟甲氧基-1,4-二氢喹啉-3-羧酸乙酯的制备方法 |
| CN114716373B (zh) * | 2022-04-14 | 2023-01-10 | 内蒙古源宏精细化工有限公司 | 一种加替沙星环合酯的制备方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2307824A1 (en) * | 1997-10-27 | 1999-05-06 | Toyama Chemical Co., Ltd. | Processes for producing 7-isoindolinequinolonecarboxylic acid derivatives and intermediates therefor,salts of 7-isoindolinequinolonecarboxylic acids, hydrates thereof, and compositions containing the same as active ingredient. |
| US5935952A (en) | 1994-08-12 | 1999-08-10 | Toyama Chemical Co., Ltd. | Quinolone- or naphthylidone-carboxylic acid derivates or their salts |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0784423B2 (ja) * | 1987-06-18 | 1995-09-13 | 宇部興産株式会社 | 3−アミノ−2−置換ベンゾイルアクリル酸誘導体 |
| JPH05194336A (ja) * | 1992-01-14 | 1993-08-03 | Kyorin Pharmaceut Co Ltd | アミノアクリル酸誘導体 |
| JP2918134B2 (ja) * | 1992-05-15 | 1999-07-12 | 宇部興産株式会社 | 3−ジアルキルアミノ−2−置換ベンゾイルアクリル酸誘導体 |
| JPH0616642A (ja) * | 1992-07-02 | 1994-01-25 | Katayama Seiyakushiyo:Kk | キノリンカルボン酸誘導体の製造方法 |
| US6531624B1 (en) * | 1998-11-18 | 2003-03-11 | Asahi Glass Company Ltd. | Aminoacrylic acid derivatives and process for producing the same |
| EP1167344A4 (en) * | 1999-03-17 | 2004-06-16 | Daiichi Seiyaku Co | PROCESS FOR THE PRODUCTION OF 5-AMINO-8-ALKYLQUINOLO NECARBOXYLIC ACID DERIVATIVES AND INTERMEDIATE PRODUCTS IN THE PRODUCTION |
-
2001
- 2001-03-07 JP JP2001565332A patent/JP4751557B2/ja not_active Expired - Lifetime
- 2001-03-07 DE DE60128797T patent/DE60128797D1/de not_active Expired - Lifetime
- 2001-03-07 US US10/221,113 patent/US6835848B1/en not_active Expired - Lifetime
- 2001-03-07 CN CNB018090362A patent/CN1202075C/zh not_active Expired - Lifetime
- 2001-03-07 AT AT01908049T patent/ATE364036T1/de not_active IP Right Cessation
- 2001-03-07 EP EP01908049A patent/EP1278717B1/en not_active Expired - Lifetime
- 2001-03-07 KR KR1020027011757A patent/KR100763077B1/ko not_active Expired - Lifetime
- 2001-03-07 AU AU35908/01A patent/AU3590801A/en not_active Abandoned
- 2001-03-07 WO PCT/IB2001/000316 patent/WO2001066512A1/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5935952A (en) | 1994-08-12 | 1999-08-10 | Toyama Chemical Co., Ltd. | Quinolone- or naphthylidone-carboxylic acid derivates or their salts |
| CA2307824A1 (en) * | 1997-10-27 | 1999-05-06 | Toyama Chemical Co., Ltd. | Processes for producing 7-isoindolinequinolonecarboxylic acid derivatives and intermediates therefor,salts of 7-isoindolinequinolonecarboxylic acids, hydrates thereof, and compositions containing the same as active ingredient. |
Also Published As
| Publication number | Publication date |
|---|---|
| US20040267019A1 (en) | 2004-12-30 |
| JP2003534243A (ja) | 2003-11-18 |
| JP4751557B2 (ja) | 2011-08-17 |
| EP1278717A4 (en) | 2005-06-08 |
| EP1278717A1 (en) | 2003-01-29 |
| KR20030017473A (ko) | 2003-03-03 |
| CN1202075C (zh) | 2005-05-18 |
| EP1278717B1 (en) | 2007-06-06 |
| DE60128797D1 (de) | 2007-07-19 |
| WO2001066512A1 (en) | 2001-09-13 |
| CN1427815A (zh) | 2003-07-02 |
| ATE364036T1 (de) | 2007-06-15 |
| AU3590801A (en) | 2001-09-17 |
| US6835848B1 (en) | 2004-12-28 |
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Patent event date: 20020907 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20060306 Comment text: Request for Examination of Application |
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Comment text: Notification of reason for refusal Patent event date: 20070109 Patent event code: PE09021S01D |
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| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20070419 Patent event code: PE09021S01D |
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| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 20070731 |
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