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 PDF

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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
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formula
compound
process according
solvent
transition metal
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English (en)
French (fr)
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CA2818628A1 (en
Inventor
Hans-Juergen Mair
Reinhard Reents
Michelangelo Scalone
Shaoning Wang
Andreas Zogg
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F Hoffmann La Roche AG
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F Hoffmann La Roche AG
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/06Antihyperlipidemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/16Amides, e.g. hydroxamic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/16Amides, e.g. hydroxamic acids
    • A61K31/165Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/167Amides, 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/06Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols from sulfides, hydropolysulfides or polysulfides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23Thiols, 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
    • C07C323/39Thiols, 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
    • C07C323/40Y being a hydrogen or a carbon atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00Thiocarboxylic acids
    • C07C327/20Esters of monothiocarboxylic acids
    • C07C327/30Esters 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00Thiocarboxylic acids
    • C07C327/20Esters of monothiocarboxylic acids
    • C07C327/32Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C07C327/34Esters 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62Benzothiazoles
    • C07D277/64Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The 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)
CA2818628A 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 Active CA2818628C (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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

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