RU2005100054A - Способ получения производных хинолина - Google Patents
Способ получения производных хинолина Download PDFInfo
- Publication number
- RU2005100054A RU2005100054A RU2005100054/04A RU2005100054A RU2005100054A RU 2005100054 A RU2005100054 A RU 2005100054A RU 2005100054/04 A RU2005100054/04 A RU 2005100054/04A RU 2005100054 A RU2005100054 A RU 2005100054A RU 2005100054 A RU2005100054 A RU 2005100054A
- Authority
- RU
- Russia
- Prior art keywords
- ethyl
- methyl
- solvent
- chlorine
- fluorine
- Prior art date
Links
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
- C07D215/48—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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (6)
1. Способ получения соединений общей формулы (I):
в которой R выбирают из метила, этила, н-пропила, изо-пропила, н-бутила, изо-бутила, втор.-бутила, и аллила; R5 выбирают метила, этила, н-пропила, изо-пропила, метокси, этокси, метилтио, этилтио, н-пропилтио, метилсульфинила, этилсульфинила, фтора, хлора, брома, трифторметила и OCHxFy;
где x=0-2, y=1-3, при условии, что x+y=3;
R6 представляет собой водород; или
R5 и R6 совместно образуют метилендиоксигруппу;
R’ выбирают из метила, метокси, фтора, хлора, брома, трифторметила и OCHxFy, где x=0-2, y=1-3, при условии, что x+y=3;
R" выбирают из водорода, фтора и хлора, при условии, что R" выбирают из фтора и хлора, если R’ выбирают из фтора и хлора;
заключающийся в реакции эфирного производного хинолин-3-карбоновой кислоты формулы А с производным анилина формула В
в среде растворителя, выбранного из нормальных или разветвленных алканов и циклоалканов, или их смесей с температурой кипения в интервале 80-200°С.
2. Способ по п.1, в котором растворитель представляет собой н-гептан, н-октан или их смеси.
3. Способ по п.1, в котором растворитель представляет собой цис,транс-декагидронафталин (Декалин®).
4. Способ по п.1, предназначенный для получения N-этил-N-фенил-5-хлор-1,2-дигидро-4-гидрокси-1-метил-2-оксохинолин-3-карбоксамида с использованием н-гептана в качестве растворителя.
5. Способ по п.1, предназначенный для получения N-этил-N-(4-трифторметилфенил)-1,2-дигидро-4-гидрокси-5-метокси-1-метил-2-оксохинолин-3-карбоксамида с использованием смеси н-гептана и н-октана в качестве растворителя.
6. Способ по п.1, предназначенный для получения N-этил-N-фенил-1,2-дигидро-5-этил-4-гидрокси-1-метил-2-оксохинолин-3-карбоксамида с использованием цис,транс-декагидронафталина (Декалин®) в качестве растворителя.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201778-8 | 2002-06-12 | ||
| SE0201778A SE0201778D0 (sv) | 2002-06-12 | 2002-06-12 | Process for the manufacture of quinoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005100054A true RU2005100054A (ru) | 2005-07-10 |
| RU2291861C2 RU2291861C2 (ru) | 2007-01-20 |
Family
ID=20288148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005100054/04A RU2291861C2 (ru) | 2002-06-12 | 2003-05-14 | Способ получения производных хинолина |
Country Status (28)
| Country | Link |
|---|---|
| EP (1) | EP1511732B9 (ru) |
| JP (1) | JP4584709B2 (ru) |
| KR (1) | KR100979216B1 (ru) |
| CN (1) | CN100418950C (ru) |
| AT (1) | ATE348814T1 (ru) |
| AU (1) | AU2003228195B2 (ru) |
| BR (1) | BR0311674A (ru) |
| CA (1) | CA2487329C (ru) |
| CY (1) | CY1107555T1 (ru) |
| DE (1) | DE60310554T2 (ru) |
| DK (1) | DK1511732T5 (ru) |
| ES (1) | ES2278160T3 (ru) |
| HR (1) | HRP20050028B1 (ru) |
| IL (1) | IL165155A (ru) |
| IS (1) | IS2975B (ru) |
| ME (1) | ME00435B (ru) |
| MX (1) | MXPA04012276A (ru) |
| NO (1) | NO329162B1 (ru) |
| NZ (1) | NZ536768A (ru) |
| PL (1) | PL210259B1 (ru) |
| PT (1) | PT1511732E (ru) |
| RS (1) | RS51021B (ru) |
| RU (1) | RU2291861C2 (ru) |
| SE (1) | SE0201778D0 (ru) |
| SI (1) | SI1511732T1 (ru) |
| UA (1) | UA78310C2 (ru) |
| WO (1) | WO2003106424A1 (ru) |
| ZA (1) | ZA200409430B (ru) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8314124B2 (en) | 2004-02-06 | 2012-11-20 | Active Biotech Ab | Crystalline salts of quinoline compounds and methods for preparing them |
| SE0400235D0 (sv) | 2004-02-06 | 2004-02-06 | Active Biotech Ab | New composition containing quinoline compounds |
| US7884208B2 (en) | 2005-10-19 | 2011-02-08 | Teva Pharmaceutical Industries, Ltd. | Crystals of laquinimod sodium, and process for the manufacture thereof |
| AR061348A1 (es) * | 2006-06-12 | 2008-08-20 | Teva Pharma | Preparados estables de laquinimod |
| BRPI0719590A2 (pt) | 2006-11-28 | 2014-01-21 | Valeant Pharmaceuticals Int | Análogos de retigabina 1,4 diamino bicíclica como modulares de canal de potássio |
| DK2234485T3 (da) | 2007-12-20 | 2014-02-10 | Teva Pharma | Stabile laquinimod-præparater |
| AU2009288108B2 (en) | 2008-09-03 | 2013-10-17 | Teva Pharmaceutical Industries, Ltd. | 2-oxo-1,2-dihydro-quinoline modulators of immune function |
| US20120009226A1 (en) * | 2008-12-17 | 2012-01-12 | Actavis Group Ptc Ehf | Highly pure laquinimod or a pharmaceutically acceptable salt thereof |
| DE102009008851A1 (de) | 2009-02-13 | 2010-08-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
| DE102010048788A1 (de) | 2009-02-13 | 2011-05-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
| KR20120045032A (ko) | 2009-07-30 | 2012-05-08 | 테바 파마슈티컬 인더스트리즈 리미티드 | 라퀴니모드를 이용한 크론병의 치료 |
| JP5859438B2 (ja) | 2009-08-10 | 2016-02-10 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドを用いたｂｄｎｆ関連疾患の治療 |
| DE102010026879A1 (de) | 2010-02-11 | 2011-08-11 | AMW GmbH, 83627 | Transdermales System mit Immunmodulator |
| JP5819328B2 (ja) | 2010-03-03 | 2015-11-24 | テバ ファーマシューティカル インダストリーズ リミティド | ラキニモドとメトトレキセートとの組合せによる関節リウマチの治療 |
| AU2011223692A1 (en) | 2010-03-03 | 2012-10-25 | Teva Pharmaceutical Industries Ltd. | Treatment of lupus nephritis using laquinimod |
| CA2802006C (en) * | 2010-07-09 | 2018-09-25 | Active Biotech Ab | Method for manufacturing of quinoline-3-carboxamides |
| EA025377B1 (ru) | 2010-07-09 | 2016-12-30 | Тева Фармасьютикал Индастриз Лтд. | Дейтерированный n-этил-n-фенил-1,2-дигидро-4-гидрокси-5-хлор-1-метил-2-оксохинолин-3-карбоксамид, его соли и их применение |
| BR112013000607A2 (pt) * | 2010-07-09 | 2016-06-28 | Teva Pharma | 5-cloro-4-hidroxi-1-metil-2-oxo-n-fenil-1,2-di-hidroquinolina-3-carboxamida, os sais e suas utilizações |
| EP2537517A1 (en) * | 2011-06-22 | 2012-12-26 | Active Biotech AB | Deuterium-enriched 4-hydroxy-5-methoxy-n,1-dimethyl-2-oxo-n-[(4-trifluoro-methyl)phenyl]-1,2-dihydroquinoline-3-carboxamide |
| SG11201401330YA (en) | 2011-10-12 | 2014-05-29 | Teva Pharma | Treatment of multiple sclerosis with combination of laquinimod and fingolimod |
| CN106063787A (zh) | 2012-02-03 | 2016-11-02 | 泰华制药工业有限公司 | 拉喹莫德用于治疗一线抗TNFα疗法失败的克罗恩氏病患者的用途 |
| EP3225617A1 (en) | 2012-02-16 | 2017-10-04 | Teva Pharmaceutical Industries Ltd | N-ethyl-n-phenyl-1,2-dihydro-4,5-di-hydroxy-1-methyl-2-oxo-3-quinoline carboxamide, preparation and uses thereof |
| TW201350467A (zh) | 2012-05-08 | 2013-12-16 | Teva Pharma | Ｎ－乙基－４－羥基－１－甲基－５－（甲基（２，３，４，５，６－五羥基己基）胺基）－２－側氧－ｎ－苯基－１，２－二氫喹啉－３－甲醯胺 |
| TW201400117A (zh) | 2012-06-05 | 2014-01-01 | Teva Pharma | 使用拉喹莫德治療眼發炎疾病 |
| TW201410244A (zh) | 2012-08-13 | 2014-03-16 | Teva Pharma | 用於治療ｇａｂａ媒介之疾病之拉喹莫德（ｌａｑｕｉｎｉｍｏｄ） |
| CN103626701A (zh) * | 2012-08-28 | 2014-03-12 | 天津药物研究院 | 一种制备喹啉衍生物的方法 |
| CN103626702A (zh) * | 2012-08-30 | 2014-03-12 | 天津药物研究院 | 一种制备喹啉酮衍生物的方法 |
| WO2014074381A1 (en) | 2012-11-07 | 2014-05-15 | Teva Pharmaceutical Industries Ltd. | Amine salts of laquinimod |
| US9233927B2 (en) * | 2013-03-14 | 2016-01-12 | Teva Pharmaceutical Industries, Ltd. | Crystals of laquinimod sodium and improved process for the manufacture thereof |
| CA2945978A1 (en) | 2014-04-29 | 2015-11-05 | Teva Pharmaceutical Industries Ltd. | Laquinimod for the treatment of relapsing-remitting multiple sclerosis (rrms) patients with a high disability status |
| ES2631194T3 (es) | 2014-09-23 | 2017-08-29 | Active Biotech Ab | Quinolincarboxamidas para usar en el tratamiento del mieloma múltiple |
| AU2015348778B2 (en) | 2014-11-19 | 2020-12-24 | Active Biotech Ab | Quinoline carboxamides for use in the treatment of leukemia |
| JP2023519153A (ja) | 2020-03-03 | 2023-05-10 | アクティブ バイオテック エイビー | 組合せ療法における使用のためのタスキニモドまたはその薬学的に許容される塩 |
| CN111732540B (zh) * | 2020-07-20 | 2020-11-13 | 湖南速博生物技术有限公司 | 一种罗喹美克的制备方法 |
| WO2022018240A1 (en) | 2020-07-23 | 2022-01-27 | Erasmus University Medical Center Rotterdam | S100 proteins as novel therapeutic targets in myeloproliferative neoplasms |
| US20240091215A1 (en) | 2021-01-18 | 2024-03-21 | Active Biotech Ab | Tasquinimod or a pharmaceutically acceptable salt thereof for use in the treatment of myelodysplastic syndrome |
| CA3218977A1 (en) | 2021-05-25 | 2022-12-01 | Hans Wannman | A plurality of tasquinimod particles and use thereof |
| AU2022303084A1 (en) | 2021-07-02 | 2024-01-25 | Active Biotech Ab | A pharmaceutical product containing tasquinimod and a method for assessing the purity of said product |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE52670B1 (en) * | 1981-03-03 | 1988-01-20 | Leo Ab | Heterocyclic carboxamides,compositions containing such compounds,and processes for their preparation |
| SE9801474D0 (sv) * | 1998-04-27 | 1998-04-27 | Active Biotech Ab | Quinoline Derivatives |
| US6077851A (en) * | 1998-04-27 | 2000-06-20 | Active Biotech Ab | Quinoline derivatives |
| US6121287A (en) * | 1998-07-15 | 2000-09-19 | Active Biotech Ab | Quinoline derivatives |
| SE9802550D0 (sv) * | 1998-07-15 | 1998-07-15 | Active Biotech Ab | Quinoline derivatives |
-
2002
- 2002-06-12 SE SE0201778A patent/SE0201778D0/xx unknown
-
2003
- 2003-05-14 WO PCT/SE2003/000780 patent/WO2003106424A1/en active IP Right Grant
- 2003-05-14 AU AU2003228195A patent/AU2003228195B2/en not_active Expired
- 2003-05-14 RS YUP-1076/04A patent/RS51021B/sr unknown
- 2003-05-14 EP EP03725956A patent/EP1511732B9/en not_active Expired - Lifetime
- 2003-05-14 KR KR1020047020088A patent/KR100979216B1/ko active IP Right Grant
- 2003-05-14 DE DE60310554T patent/DE60310554T2/de not_active Expired - Lifetime
- 2003-05-14 MX MXPA04012276A patent/MXPA04012276A/es active IP Right Grant
- 2003-05-14 BR BRPI0311674-3A patent/BR0311674A/pt not_active Application Discontinuation
- 2003-05-14 PL PL373817A patent/PL210259B1/pl unknown
- 2003-05-14 ME MEP-2008-656A patent/ME00435B/me unknown
- 2003-05-14 AT AT03725956T patent/ATE348814T1/de active
- 2003-05-14 ES ES03725956T patent/ES2278160T3/es not_active Expired - Lifetime
- 2003-05-14 JP JP2004513257A patent/JP4584709B2/ja not_active Expired - Lifetime
- 2003-05-14 NZ NZ536768A patent/NZ536768A/en not_active IP Right Cessation
- 2003-05-14 RU RU2005100054/04A patent/RU2291861C2/ru not_active IP Right Cessation
- 2003-05-14 PT PT03725956T patent/PT1511732E/pt unknown
- 2003-05-14 CA CA2487329A patent/CA2487329C/en not_active Expired - Lifetime
- 2003-05-14 DK DK03725956T patent/DK1511732T5/da active
- 2003-05-14 SI SI200330688T patent/SI1511732T1/sl unknown
- 2003-05-14 CN CNB038135310A patent/CN100418950C/zh not_active Expired - Lifetime
- 2003-05-14 UA UA20041109639A patent/UA78310C2/xx unknown
-
2004
- 2004-11-11 IL IL165155A patent/IL165155A/en active IP Right Grant
- 2004-11-23 ZA ZA200409430A patent/ZA200409430B/xx unknown
- 2004-11-24 IS IS7550A patent/IS2975B/is unknown
- 2004-12-29 NO NO20045703A patent/NO329162B1/no not_active IP Right Cessation
-
2005
- 2005-01-11 HR HRP20050028AA patent/HRP20050028B1/hr not_active IP Right Cessation
-
2007
- 2007-03-01 CY CY20071100295T patent/CY1107555T1/el unknown
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