CA2818628C - Processes for the preparation of s-[2-[1-(2-ethylbutyl) cyclcohexanecarbonylamino]phenyl] 2-methylthiopropionate and derivativesthereof by hydrogenation of disulfide precursors - Google Patents
Processes for the preparation of s-[2-[1-(2-ethylbutyl) cyclcohexanecarbonylamino]phenyl] 2-methylthiopropionate and derivativesthereof by hydrogenation of disulfide precursors Download PDFInfo
- Publication number
- CA2818628C CA2818628C CA2818628A CA2818628A CA2818628C CA 2818628 C CA2818628 C CA 2818628C CA 2818628 A CA2818628 A CA 2818628A CA 2818628 A CA2818628 A CA 2818628A CA 2818628 C CA2818628 C CA 2818628C
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- process according
- solvent
- transition metal
- 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.)
- Active
Links
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
- C07C319/06—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols from sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/30—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/20—Esters of monothiocarboxylic acids
- C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C07C327/34—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups with amino groups bound to the same hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10195294 | 2010-12-16 | ||
| EP10195294.3 | 2010-12-16 | ||
| PCT/EP2011/072470 WO2012080178A1 (en) | 2010-12-16 | 2011-12-12 | Process for the preparation of aromatic thiol derivatives by hydrogenation of disulfides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2818628A1 CA2818628A1 (en) | 2012-06-21 |
| CA2818628C true CA2818628C (en) | 2019-02-26 |
Family
ID=43877331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2818628A Active CA2818628C (en) | 2010-12-16 | 2011-12-12 | Processes for the preparation of s-[2-[1-(2-ethylbutyl) cyclcohexanecarbonylamino]phenyl] 2-methylthiopropionate and derivativesthereof by hydrogenation of disulfide precursors |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8664403B2 (enExample) |
| EP (1) | EP2651882B1 (enExample) |
| JP (1) | JP6054875B2 (enExample) |
| KR (1) | KR101947840B1 (enExample) |
| CN (1) | CN103261155B (enExample) |
| BR (1) | BR112013014029B1 (enExample) |
| CA (1) | CA2818628C (enExample) |
| ES (1) | ES2705496T3 (enExample) |
| MX (1) | MX2013006038A (enExample) |
| RU (1) | RU2607636C2 (enExample) |
| TR (1) | TR201818880T4 (enExample) |
| WO (1) | WO2012080178A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2978859T (pt) | 2013-03-27 | 2018-10-04 | Hoffmann La Roche | Marcadores genéticos para previsão da capacidade de resposta à terapêutica |
| RU2703192C2 (ru) | 2014-07-30 | 2019-10-15 | Ф. Хоффманн-Ля Рош Аг | Генетические маркеры для прогнозирования ответа на терапию поднимающими уровень hdl или имитирующими hdl агентами |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2483447A (en) * | 1946-01-17 | 1949-10-04 | Du Pont | Aminomercaptobenzenesulfon amides |
| JPS60199871A (ja) * | 1984-03-26 | 1985-10-09 | Nippon Kayaku Co Ltd | チオフエノ−ル類の製造法 |
| FR2711366B1 (fr) * | 1993-10-20 | 1995-12-15 | Elf Aquitaine | Synthèse du méthylmercaptan à partir du diméthyldisulfure. |
| JP2894445B2 (ja) * | 1997-02-12 | 1999-05-24 | 日本たばこ産業株式会社 | Cetp活性阻害剤として有効な化合物 |
| DE19746512A1 (de) * | 1997-10-22 | 1999-04-29 | Bayer Ag | Verfahren zur Herstellung von Arylmercaptanen durch Hydrierung von Diaryldisulfiden |
| US7435849B2 (en) | 2005-10-31 | 2008-10-14 | Hoffmann-La Roche Inc. | Process for the production of acid chlorides |
| EP1935867A1 (en) | 2006-12-20 | 2008-06-25 | F. Hoffmann-La Roche Ag | Process for preparing 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid |
| DE102007020694A1 (de) * | 2007-05-03 | 2008-11-06 | Evonik Degussa Gmbh | Schwefelhaltige Metathesekatalysatoren |
| AU2009231423B2 (en) * | 2008-04-04 | 2014-01-30 | F. Hoffmann-La Roche Ag | New process for the preparation of cyclohexanecarboxylic acid derivatives |
| CN101952236B (zh) * | 2008-04-04 | 2014-07-02 | 弗·哈夫曼-拉罗切有限公司 | 通过相应的环己烷羧酰胺衍生物制备环己烷羧酸衍生物的新工艺 |
| JP5325980B2 (ja) * | 2008-06-17 | 2013-10-23 | エフ.ホフマン−ラ ロシュ アーゲー | 薬学的に活性なアミドの製造における中間体としての1−(2−エチル−ブチル)−シクロヘキサンカルボン酸エステル |
-
2011
- 2011-12-12 EP EP11804528.5A patent/EP2651882B1/en active Active
- 2011-12-12 CN CN201180060242.4A patent/CN103261155B/zh active Active
- 2011-12-12 ES ES11804528T patent/ES2705496T3/es active Active
- 2011-12-12 MX MX2013006038A patent/MX2013006038A/es active IP Right Grant
- 2011-12-12 RU RU2013131443A patent/RU2607636C2/ru active
- 2011-12-12 KR KR1020137018142A patent/KR101947840B1/ko active Active
- 2011-12-12 CA CA2818628A patent/CA2818628C/en active Active
- 2011-12-12 BR BR112013014029-1A patent/BR112013014029B1/pt active IP Right Grant
- 2011-12-12 WO PCT/EP2011/072470 patent/WO2012080178A1/en not_active Ceased
- 2011-12-12 JP JP2013543689A patent/JP6054875B2/ja active Active
- 2011-12-12 TR TR2018/18880T patent/TR201818880T4/tr unknown
- 2011-12-13 US US13/324,199 patent/US8664403B2/en active Active
-
2013
- 2013-12-18 US US14/132,221 patent/US9603816B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8664403B2 (en) | 2014-03-04 |
| CN103261155B (zh) | 2016-08-10 |
| EP2651882B1 (en) | 2018-11-14 |
| KR20130127993A (ko) | 2013-11-25 |
| US20120157504A1 (en) | 2012-06-21 |
| RU2013131443A (ru) | 2015-01-27 |
| ES2705496T3 (es) | 2019-03-25 |
| US20140171502A1 (en) | 2014-06-19 |
| BR112013014029B1 (pt) | 2021-07-20 |
| WO2012080178A1 (en) | 2012-06-21 |
| JP6054875B2 (ja) | 2016-12-27 |
| RU2607636C2 (ru) | 2017-01-10 |
| CA2818628A1 (en) | 2012-06-21 |
| MX2013006038A (es) | 2013-08-01 |
| EP2651882A1 (en) | 2013-10-23 |
| JP2014510019A (ja) | 2014-04-24 |
| HK1187893A1 (zh) | 2014-04-17 |
| CN103261155A (zh) | 2013-08-21 |
| US9603816B2 (en) | 2017-03-28 |
| BR112013014029A2 (pt) | 2016-09-13 |
| TR201818880T4 (tr) | 2019-01-21 |
| KR101947840B1 (ko) | 2019-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9000218B2 (en) | Process for preparing secondary amines in the liquid phase | |
| AU2017292177B2 (en) | Industrial process for the preparation of cariprazine | |
| CN101878192B (zh) | 4-全氟异丙基苯胺类的制造方法 | |
| EP2651882B1 (en) | Process for the preparation of aromatic thiol derivatives by hydrogenation of disulfides | |
| US8242311B2 (en) | Process for preparing 2,2-difluoroethylamine and salts thereof proceeding from difluoroacetonitrile | |
| CN110028422B (zh) | 一种咪唑盐酸盐催化氨基保护的方法 | |
| CN113831269B (zh) | 一种乙烯基二硫代氨基甲酸酯类化合物的合成方法 | |
| HK1187893B (en) | Process for the preparation of aromatic thiol derivatives by hydrogenation of disulfides | |
| JP2006182676A (ja) | アミド化合物の製造方法 | |
| US8692021B2 (en) | Method of preparing Neramexane or a salt thereof | |
| JPWO2007119361A1 (ja) | キナゾリン−4−オン誘導体の製造方法 | |
| Suryakiran et al. | N-Benzyloxycarbonylation of amines in the ionic liquid [TPA][L-Pro] as an efficient reaction medium | |
| JP5881189B2 (ja) | ヒドロキシカルボン酸アミド化合物の製法及び新規なアリールボロン酸化合物 | |
| CN103012154B (zh) | 由苯磺酰胺衍生物氨解制备有机胺的方法 | |
| CN118164877A (zh) | 一种西司他丁钠中间体化合物 | |
| KR101644141B1 (ko) | 이온성 액체계 촉매 및 이를 이용한 n,n''-치환 우레아의 제조 방법 | |
| BR112012014046A2 (pt) | processo para a produção de 2,2-difluoroetilamina e de seus sais a partir de difluoroacetonitrila | |
| CN1428333A (zh) | 一种非光气路线合成苯胺基甲酸酯的方法 | |
| CN101415668A (zh) | 羧酸酰氯化合物的制造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20161201 |
|
| MPN | Maintenance fee for patent paid |
Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 13TH ANNIV.) - STANDARD Year of fee payment: 13 |
|
| U00 | Fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20241206 |
|
| U11 | Full renewal or maintenance fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT DETERMINED COMPLIANT Effective date: 20241206 Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL Effective date: 20241206 |
|
| MPN | Maintenance fee for patent paid |
Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 14TH ANNIV.) - STANDARD Year of fee payment: 14 |
|
| U00 | Fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20251124 |
|
| U11 | Full renewal or maintenance fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL Effective date: 20251124 |