RU2003131870A - Способы получения ингибиторов сетр - Google Patents
Способы получения ингибиторов сетр Download PDFInfo
- Publication number
- RU2003131870A RU2003131870A RU2003131870/04A RU2003131870A RU2003131870A RU 2003131870 A RU2003131870 A RU 2003131870A RU 2003131870/04 A RU2003131870/04 A RU 2003131870/04A RU 2003131870 A RU2003131870 A RU 2003131870A RU 2003131870 A RU2003131870 A RU 2003131870A
- Authority
- RU
- Russia
- Prior art keywords
- formula
- compound
- base
- compounds
- specified
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 24
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 44
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 238000011084 recovery Methods 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims 1
- -1 3,5-bis (trifluoromethyl) benzyl halide Chemical class 0.000 claims 1
- LDWLIXZSDPXYDR-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC(C=O)=CC(C(F)(F)F)=C1 LDWLIXZSDPXYDR-UHFFFAOYSA-N 0.000 claims 1
- 239000012345 acetylating agent Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- SEYVRRKNFKPZAE-UHFFFAOYSA-N CCC(CC1NC(OC)=O)N(C(OCC)=O)c2c1cc(C(F)(F)F)cc2 Chemical compound CCC(CC1NC(OC)=O)N(C(OCC)=O)c2c1cc(C(F)(F)F)cc2 SEYVRRKNFKPZAE-UHFFFAOYSA-N 0.000 description 1
- 0 CC[C@@](CC(NC(O*)=O)=O)Nc1ccc(C(F)(F)F)cc1 Chemical compound CC[C@@](CC(NC(O*)=O)=O)Nc1ccc(C(F)(F)F)cc1 0.000 description 1
- RZSARXINBOJSRD-SECBINFHSA-N CC[C@H](CC(N)=O)Nc1ccc(C(F)(F)F)cc1 Chemical compound CC[C@H](CC(N)=O)Nc1ccc(C(F)(F)F)cc1 RZSARXINBOJSRD-SECBINFHSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
- C07C271/64—Y being a hydrogen or a carbon atom, e.g. benzoylcarbamates
-
- 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Claims (15)
2. Способ по п.1, где указанным основанием является пиридиновое основание.
4. Способ по п.3, где указанным основанием является трет-бутилат калия.
6. Способ по п.5, где указанное соединение формулы VIIA получают способом, включающим восстановление соединения формулы VI
где R означает метил, восстановителем с получением восстановленного соединения и циклизацию восстановленного соединения в кислотных условиях с образованием соединения формулы VIIA.
11. Способ получения соединения формулы IB
включающий стадии
а) восстановления соединения формулы VIIIB
где R1 означает бензил или замещенный бензил,
восстановителем с получением сложного изопропилового эфира цис-4-амино-2-этил-6-трифторметил-3,4-дигидро-2H-хинолин-1-карбоновой кислоты;
b) обработки указанного сложного изопропилового эфира цис-4-амино-2-этил-6-трифторметил-3,4-дигидро-2H-хинолин-1-карбоновой кислоты вначале 3,5-бистрифторметилбензальдегидом в кислотных условиях с последующей обработкой восстановителем с получением сложного изопропилового эфира цис-4-(3,5-бистрифторметилбензиламино)-2-этил-6-трифторметил-3,4-дигидро-2H-хинолин-1-карбоновой кислоты;
c) обработки указанного сложного изопропилового эфира цис-4-(3,5-бистрифторметилбензиламино)-2-этил-6-трифторметил-3,4-дигидро-2H-хинолин-1-карбоновой кислоты ацетилирующим агентом с получением соединения формулы IB,
где указанные соединения формулы VIIIB получают способом, включающим присоединение соединения формулы VIIB
к изопропилхлорформиату с образованием соединения формулы VIIIB.
12. Способ по п.11, где указанное соединение формулы VIIВ получают способом, включающим восстановление соединения формулы VI
где R1 означает бензил или замещенный бензил, восстановителем с получением восстановленного соединения и циклизацию восстановленного соединения в кислотных условиях с образованием соединения формулы VIIВ.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28752201P | 2001-04-30 | 2001-04-30 | |
US60/287,522 | 2001-04-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2003131870A true RU2003131870A (ru) | 2005-01-27 |
RU2259355C2 RU2259355C2 (ru) | 2005-08-27 |
Family
ID=23103272
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2003131870/04A RU2259355C2 (ru) | 2001-04-30 | 2002-04-08 | Способ получения ингибитора сетр, промежуточное вещество и способ его получения |
RU2003131871/04A RU2265010C2 (ru) | 2001-04-30 | 2002-04-08 | Промежуточные соединения для ингибиторов cetp и способы их получения |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2003131871/04A RU2265010C2 (ru) | 2001-04-30 | 2002-04-08 | Промежуточные соединения для ингибиторов cetp и способы их получения |
Country Status (25)
Country | Link |
---|---|
US (3) | US6600045B2 (ru) |
EP (2) | EP1425270B1 (ru) |
JP (2) | JP3924251B2 (ru) |
KR (2) | KR100591998B1 (ru) |
CN (3) | CN100357265C (ru) |
AR (3) | AR036331A1 (ru) |
AT (2) | ATE321755T1 (ru) |
AU (1) | AU2002253448B2 (ru) |
BR (2) | BR0209291A (ru) |
CA (2) | CA2445623A1 (ru) |
CZ (2) | CZ20032900A3 (ru) |
DE (2) | DE60210265T2 (ru) |
DK (2) | DK1425270T3 (ru) |
ES (2) | ES2256461T3 (ru) |
HK (1) | HK1062294A1 (ru) |
HU (2) | HU225777B1 (ru) |
IL (2) | IL157544A0 (ru) |
MX (2) | MXPA03009936A (ru) |
PL (2) | PL366700A1 (ru) |
PT (1) | PT1425270E (ru) |
RU (2) | RU2259355C2 (ru) |
TW (1) | TWI250974B (ru) |
WO (2) | WO2002088085A2 (ru) |
YU (2) | YU84303A (ru) |
ZA (2) | ZA200306599B (ru) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
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US6197786B1 (en) * | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
US20040002615A1 (en) * | 2002-06-28 | 2004-01-01 | Allen David Robert | Preparation of chiral amino-nitriles |
JP2006021999A (ja) * | 2002-07-12 | 2006-01-26 | Kaneka Corp | 光学活性β−アミノニトリル化合物およびその対掌体アミド化合物の製造方法 |
US7504508B2 (en) | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
US20090181966A1 (en) * | 2002-10-04 | 2009-07-16 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
PL376156A1 (en) | 2002-10-04 | 2005-12-27 | Millennium Pharmaceuticals, Inc. | Pgd2 receptor antagonists for the treatment of inflammatory diseases |
JP2006513186A (ja) | 2002-12-20 | 2006-04-20 | ファイザー・プロダクツ・インク | Cetp阻害剤およびhmg−coaレダクターゼ阻害剤を含む剤形 |
WO2004074255A2 (en) * | 2003-02-18 | 2004-09-02 | Takasago International Corporation | Method for producing an optically active tetrahydroquinoline |
WO2004083166A1 (ja) * | 2003-03-17 | 2004-09-30 | Kaneka Corporation | (r)-3-[4-(トリフルオロメチル)フェニルアミノ]-ペンタン酸アミド誘導体の製造法 |
US7223859B2 (en) | 2003-03-17 | 2007-05-29 | Pfizer Inc. | Method for producing (R)-3-[4-(trifluoromethyl) phenylamino]-pentanoic acid amide derivative |
MXPA06003357A (es) | 2003-09-26 | 2006-06-08 | Japan Tobacco Inc | Metodo para inhibir la produccion de lipoproteina remanente. |
DK1670768T3 (da) * | 2003-10-08 | 2009-11-09 | Lilly Co Eli | Forbindelser og fremgangsmåder til at behandle dyslipidæmi |
ATE428411T1 (de) * | 2003-11-07 | 2009-05-15 | Jj Pharma Inc | Hdl-verstärkende kombinationstherapie-komplexe |
AR048528A1 (es) * | 2004-04-07 | 2006-05-03 | Millennium Pharm Inc | Compuestos derivados de quinolina como antagonistas del receptor de pgd2 para el tratamiento de enfermedades inflamatorias y composiciones farmacéuticas que los contienen. |
JP2008504266A (ja) * | 2004-06-24 | 2008-02-14 | イーライ リリー アンド カンパニー | 異脂肪血症を治療するための化合物及び方法 |
DE102004031656A1 (de) * | 2004-06-30 | 2006-01-19 | Merck Patent Gmbh | Tetrahydrochinoline |
WO2006069162A1 (en) * | 2004-12-20 | 2006-06-29 | Reddy Us Therapeutics, Inc. | Novel heterocyclic compounds and their pharmaceutical compositions |
UA90706C2 (ru) | 2005-02-24 | 2010-05-25 | Милленниум Фармасьютикалз, Инк. | Антагонисты рецептора pgd2 для лечения воспалительных заболеваний |
BRPI0611838A2 (pt) * | 2005-06-20 | 2012-08-28 | Astrazeneca Ab | processo para a preparação de um composto |
UY30244A1 (es) | 2006-03-30 | 2007-11-30 | Tanabe Seiyaku Co | Un proceso para preparar derivados de tetrahidroquinolina |
DE102006031149A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
DE102006031262A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
DE102006032391A1 (de) * | 2006-07-04 | 2008-01-17 | Merck Patent Gmbh | Fluortenside |
DE102006031143A1 (de) * | 2006-07-04 | 2008-01-24 | Merck Patent Gmbh | Fluortenside |
DE102006031151A1 (de) * | 2006-07-04 | 2008-01-10 | Merck Patent Gmbh | Fluortenside |
AR065670A1 (es) | 2007-03-09 | 2009-06-24 | Indigene Pharmaceuticals Inc | Combinacion de metformina r-(+) lipoato y agentes antihiperlipidemicos para el tratamiento de hiperglucemia diabetica y complicaciones diabeticas |
JP2011256110A (ja) * | 2008-09-30 | 2011-12-22 | Takeda Chem Ind Ltd | ヘキサヒドロピロロキノリンの製造法 |
TWI450896B (zh) * | 2009-06-30 | 2014-09-01 | Lilly Co Eli | 反式-4-〔〔(5s)-5-〔〔〔3,5-雙(三氟甲基)苯基〕甲基〕(2-甲基-2h-四唑-5-基)胺基〕-2,3,4,5-四氫-7,9-二甲基-1h-1-苯并氮呯-1-基〕甲基〕-環己基羧酸 |
AU2012243583B2 (en) | 2011-04-12 | 2015-10-22 | Chong Kun Dang Pharmaceutical Corp. | Cycloalkenyl aryl derivatives for CETP inhibitor |
AU2012282109B2 (en) * | 2011-07-08 | 2016-06-23 | Novartis Ag | Method of treating atherosclerosis in high triglyceride subjects |
EP2943474B1 (en) | 2013-01-31 | 2017-07-05 | Chong Kun Dang Pharmaceutical Corp. | Biaryl- or heterocyclic biaryl-substituted cyclohexene derivative compounds as cetp inhibitors |
WO2015067405A1 (en) * | 2013-11-11 | 2015-05-14 | Lonza Ltd | Method for preparation of cyano compounds of the 13th group with a lewis acid |
US10112904B2 (en) * | 2014-08-12 | 2018-10-30 | Dezima Pharma B.V. | Process for preparing synthetic intermediates for preparing tetrahydroquinoline derivatives |
CN105294559B (zh) * | 2015-06-24 | 2017-11-14 | 厦门法茉维特动物药业有限公司 | 一种医药中间体4‑氨基喹啉类化合物的合成方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE316532T1 (de) | 1998-07-10 | 2006-02-15 | Massachusetts Inst Technology | Liganden für metalle und metall-katalysiertes verfahren |
US6197786B1 (en) * | 1998-09-17 | 2001-03-06 | Pfizer Inc | 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines |
GT199900147A (es) | 1998-09-17 | 1999-09-06 | 1, 2, 3, 4- tetrahidroquinolinas 2-sustituidas 4-amino sustituidas. |
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2002
- 2002-04-08 HU HU0304041A patent/HU225777B1/hu not_active IP Right Cessation
- 2002-04-08 PL PL02366700A patent/PL366700A1/xx not_active Application Discontinuation
- 2002-04-08 RU RU2003131870/04A patent/RU2259355C2/ru not_active IP Right Cessation
- 2002-04-08 MX MXPA03009936A patent/MXPA03009936A/es active IP Right Grant
- 2002-04-08 BR BR0209291-3A patent/BR0209291A/pt not_active IP Right Cessation
- 2002-04-08 KR KR1020037014135A patent/KR100591998B1/ko not_active IP Right Cessation
- 2002-04-08 DK DK02722567T patent/DK1425270T3/da active
- 2002-04-08 CA CA002445623A patent/CA2445623A1/en not_active Abandoned
- 2002-04-08 AT AT02722567T patent/ATE321755T1/de not_active IP Right Cessation
- 2002-04-08 EP EP02722567A patent/EP1425270B1/en not_active Expired - Lifetime
- 2002-04-08 MX MXPA03009935A patent/MXPA03009935A/es active IP Right Grant
- 2002-04-08 AU AU2002253448A patent/AU2002253448B2/en not_active Ceased
- 2002-04-08 CN CNB2005100529529A patent/CN100357265C/zh not_active Expired - Fee Related
- 2002-04-08 CN CNB028091442A patent/CN1297541C/zh not_active Expired - Fee Related
- 2002-04-08 WO PCT/IB2002/001214 patent/WO2002088085A2/en active IP Right Grant
- 2002-04-08 PT PT02722567T patent/PT1425270E/pt unknown
- 2002-04-08 PL PL02366584A patent/PL366584A1/xx not_active Application Discontinuation
- 2002-04-08 YU YU84303A patent/YU84303A/sh unknown
- 2002-04-08 YU YU84403A patent/YU84403A/sh unknown
- 2002-04-08 JP JP2002585387A patent/JP3924251B2/ja not_active Expired - Fee Related
- 2002-04-08 CA CA002445693A patent/CA2445693A1/en not_active Abandoned
- 2002-04-08 ES ES02722569T patent/ES2256461T3/es not_active Expired - Lifetime
- 2002-04-08 CN CNB028091663A patent/CN1267411C/zh not_active Expired - Fee Related
- 2002-04-08 ES ES02722567T patent/ES2259080T3/es not_active Expired - Lifetime
- 2002-04-08 AT AT02722569T patent/ATE316957T1/de not_active IP Right Cessation
- 2002-04-08 IL IL15754402A patent/IL157544A0/xx unknown
- 2002-04-08 CZ CZ20032900A patent/CZ20032900A3/cs unknown
- 2002-04-08 DK DK02722569T patent/DK1383734T3/da active
- 2002-04-08 DE DE60210265T patent/DE60210265T2/de not_active Expired - Fee Related
- 2002-04-08 EP EP02722569A patent/EP1383734B1/en not_active Expired - Lifetime
- 2002-04-08 HU HU0304039A patent/HUP0304039A3/hu unknown
- 2002-04-08 JP JP2002585373A patent/JP3924250B2/ja not_active Expired - Fee Related
- 2002-04-08 CZ CZ20032898A patent/CZ20032898A3/cs unknown
- 2002-04-08 IL IL15754602A patent/IL157546A0/xx unknown
- 2002-04-08 KR KR1020037014134A patent/KR100639745B1/ko not_active IP Right Cessation
- 2002-04-08 DE DE60209004T patent/DE60209004T2/de not_active Expired - Fee Related
- 2002-04-08 BR BR0209238-7A patent/BR0209238A/pt not_active IP Right Cessation
- 2002-04-08 WO PCT/IB2002/001217 patent/WO2002088069A2/en active IP Right Grant
- 2002-04-08 RU RU2003131871/04A patent/RU2265010C2/ru not_active IP Right Cessation
- 2002-04-24 TW TW091108446A patent/TWI250974B/zh not_active IP Right Cessation
- 2002-04-29 AR ARP020101576A patent/AR036331A1/es unknown
- 2002-04-29 AR ARP020101575A patent/AR035963A1/es unknown
- 2002-04-30 US US10/136,758 patent/US6600045B2/en not_active Expired - Fee Related
- 2002-04-30 US US10/137,314 patent/US6689897B2/en not_active Expired - Fee Related
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2003
- 2003-04-18 US US10/418,821 patent/US6706881B2/en not_active Expired - Fee Related
- 2003-08-25 ZA ZA200306599A patent/ZA200306599B/en unknown
- 2003-08-25 ZA ZA200306600A patent/ZA200306600B/en unknown
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2004
- 2004-06-15 AR ARP040102071A patent/AR044706A2/es not_active Application Discontinuation
- 2004-07-19 HK HK04105255A patent/HK1062294A1/xx not_active IP Right Cessation
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