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
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 |
---|---|---|---|
SE0201778A SE0201778D0 (sv) | 2002-06-12 | 2002-06-12 | Process for the manufacture of quinoline derivatives |
SE0201778-8 | 2002-06-12 |
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 |
UA92761C2 (ru) * | 2005-10-19 | 2010-12-10 | Тева Фармасьютикл Индастриз, Лтд. | Кристаллы лаквинимода натрия и способ их изготовления |
AU2007258366B2 (en) * | 2006-06-12 | 2012-10-25 | Active Biotech, Ab | Stable laquinimod preparations |
US8030518B2 (en) | 2006-11-28 | 2011-10-04 | Valeant Pharmaceuticals International | 1,4 diamino bicyclic retigabine analogues as potassium channel modulators |
SI2234485T1 (sl) | 2007-12-20 | 2014-03-31 | Teva Pharmaceutical Industries Ltd. | Stabilni lakvinimodni pripravki |
EA021227B1 (ru) | 2008-09-03 | 2015-05-29 | Тева Фармасьютикал Индастриз Лтд. | 2-оксо-1,2-дигидрохинолиновые модуляторы иммунной функции |
EP2376456A2 (en) * | 2008-12-17 | 2011-10-19 | Actavis Group Ptc Ehf | Highly pure laquinimod or a pharmaceutically acceptable salt thereof |
DE102010048788A1 (de) | 2009-02-13 | 2011-05-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
DE102009008851A1 (de) | 2009-02-13 | 2010-08-19 | Amw Gmbh | Transdermales System mit Immunmodulator |
ES2564931T3 (es) | 2009-07-30 | 2016-03-30 | Teva Pharmaceutical Industries Ltd. | Tratamiento de enfermedad de Crohn con laquinimod |
DK2467372T3 (en) | 2009-08-10 | 2016-08-22 | Teva Pharma | TREATMENT OF BDNF-RELATED DISEASES USING LAQUINIMOD |
DE102010026879A1 (de) | 2010-02-11 | 2011-08-11 | AMW GmbH, 83627 | Transdermales System mit Immunmodulator |
PT2542079E (pt) | 2010-03-03 | 2014-07-18 | Teva Pharma | Tratamento da artrite reumatoide com uma combinação de laquinimod e metotrexato |
PE20130613A1 (es) | 2010-03-03 | 2013-06-23 | Teva Pharma | Tratamiento de lupus nefritis usando laquinimod |
ES2563208T3 (es) * | 2010-07-09 | 2016-03-11 | Active Biotech Ab | Método para fabricar quinolina-3-carboxamidas |
US20120010239A1 (en) * | 2010-07-09 | 2012-01-12 | Ulf Tomas Fristedt | 5-chloro-4-hydroxy-1-methyl-2-oxo-n-phenyl-1,2-dihydroquinoline-3-carboxamide, salts and uses thereof |
KR20130092558A (ko) | 2010-07-09 | 2013-08-20 | 테바 파마슈티컬 인더스트리즈 리미티드 | 중수소화된 n-에틸-n-페닐-1,2-다이하이드로-4-하이드록시-5-클로로-1-메틸-2-옥소퀴놀린-3-카복스아마이드, 그의 염 및 용도 |
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 |
US8889627B2 (en) | 2011-10-12 | 2014-11-18 | Teva Pharmaceutical Industries, Ltd. | Treatment of multiple sclerosis with combination of laquinimod and fingolimod |
WO2013116657A1 (en) | 2012-02-03 | 2013-08-08 | Teva Pharmaceutical Industries Ltd. | USE OF LAQUINIMOD FOR TREATING CROHN'S DISEASE PATIENTS WHO FAILED FIRST-LINE ANTI-TNFα THERAPY |
US9284276B2 (en) | 2012-02-16 | 2016-03-15 | Teva Pharmaceutical Industries, Ltd. | N-ethyl-N-phenyl-1,2-dihydro-4,5-di-hydroxy-1-methyl-2-oxo-3-quinolinecarboxamide, 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 |
MX2015005632A (es) | 2012-11-07 | 2016-02-05 | Teva Pharma | Sales de amina de laquinimod. |
NZ630427A (en) | 2013-03-14 | 2017-06-30 | Teva Pharma | Crystals of laquinimod sodium and improved process for the manufacture thereof |
AU2015253330A1 (en) | 2014-04-29 | 2016-12-01 | Teva Pharmaceutical Industries Ltd. | Laquinimod for the treatment of relapsing-remitting multiple sclerosis (RRMS) patients with a high disability status |
KR102533033B1 (ko) | 2014-09-23 | 2023-05-15 | 액티브 바이오테크 에이비 | 다발성 골수종의 치료에 사용하기 위한 퀴놀린 카르복사미드 |
MX2017006110A (es) | 2014-11-19 | 2017-07-27 | Active Biotech Ab | Carboxamidas de quinolina para usarse en el tratamiento de leucemia. |
MX2022010327A (es) | 2020-03-03 | 2022-11-09 | Active Biotech Ab | Tasquinimod o una sal farmaceuticamente aceptable del mismo para el uso en una terapia combinada. |
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 |
CA3185531A1 (en) | 2020-07-23 | 2022-01-27 | Rebekka Katharina Marita SCHNEIDER-KRAMANN | 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 |
IL309486A (en) | 2021-07-02 | 2024-02-01 | Active Biotech Ab | A pharmacy product containing tesquinimod and a method for evaluating the cleanliness of this 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 |
US6077851A (en) * | 1998-04-27 | 2000-06-20 | Active Biotech Ab | Quinoline derivatives |
SE9801474D0 (sv) * | 1998-04-27 | 1998-04-27 | Active Biotech Ab | Quinoline Derivatives |
SE9802550D0 (sv) * | 1998-07-15 | 1998-07-15 | Active Biotech Ab | Quinoline derivatives |
US6121287A (en) * | 1998-07-15 | 2000-09-19 | Active Biotech Ab | Quinoline derivatives |
-
2002
- 2002-06-12 SE SE0201778A patent/SE0201778D0/xx unknown
-
2003
- 2003-05-14 BR BRPI0311674-3A patent/BR0311674A/pt not_active Application Discontinuation
- 2003-05-14 ME MEP-2008-656A patent/ME00435B/me unknown
- 2003-05-14 ES ES03725956T patent/ES2278160T3/es not_active Expired - Lifetime
- 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 SI SI200330688T patent/SI1511732T1/sl unknown
- 2003-05-14 WO PCT/SE2003/000780 patent/WO2003106424A1/en active IP Right Grant
- 2003-05-14 JP JP2004513257A patent/JP4584709B2/ja not_active Expired - Lifetime
- 2003-05-14 CA CA2487329A patent/CA2487329C/en not_active Expired - Lifetime
- 2003-05-14 KR KR1020047020088A patent/KR100979216B1/ko active IP Right Grant
- 2003-05-14 UA UA20041109639A patent/UA78310C2/xx unknown
- 2003-05-14 NZ NZ536768A patent/NZ536768A/en not_active IP Right Cessation
- 2003-05-14 MX MXPA04012276A patent/MXPA04012276A/es active IP Right Grant
- 2003-05-14 DK DK03725956T patent/DK1511732T5/da active
- 2003-05-14 CN CNB038135310A patent/CN100418950C/zh not_active Expired - Lifetime
- 2003-05-14 PL PL373817A patent/PL210259B1/pl unknown
- 2003-05-14 AU AU2003228195A patent/AU2003228195B2/en not_active Expired
- 2003-05-14 PT PT03725956T patent/PT1511732E/pt unknown
- 2003-05-14 RU RU2005100054/04A patent/RU2291861C2/ru not_active IP Right Cessation
- 2003-05-14 AT AT03725956T patent/ATE348814T1/de active
- 2003-05-14 DE DE60310554T patent/DE60310554T2/de not_active Expired - Lifetime
-
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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