RU2607636C2 - Способ получения ароматических тиольных производных при гидрировании дисульфидов - Google Patents

Способ получения ароматических тиольных производных при гидрировании дисульфидов Download PDF

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Publication number
RU2607636C2
RU2607636C2 RU2013131443A RU2013131443A RU2607636C2 RU 2607636 C2 RU2607636 C2 RU 2607636C2 RU 2013131443 A RU2013131443 A RU 2013131443A RU 2013131443 A RU2013131443 A RU 2013131443A RU 2607636 C2 RU2607636 C2 RU 2607636C2
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formula
compound
solvent
transition metal
hydrogenation catalyst
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RU2013131443A
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Russian (ru)
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RU2013131443A (ru
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Ханс-Йюрген МАЙР
Райнхард РЕНТС
Микеланджело СКАЛОНЕ
Шаонин ВАН
Андреас ЦОГГ
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Ф. Хоффманн-Ля Рош Аг
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    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Pain & Pain Management (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (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)
RU2013131443A 2010-12-16 2011-12-12 Способ получения ароматических тиольных производных при гидрировании дисульфидов RU2607636C2 (ru)

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
RU2013131443A RU2013131443A (ru) 2015-01-27
RU2607636C2 true RU2607636C2 (ru) 2017-01-10

Family

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Family Applications (1)

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RU2013131443A RU2607636C2 (ru) 2010-12-16 2011-12-12 Способ получения ароматических тиольных производных при гидрировании дисульфидов

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
MX370538B (es) 2013-03-27 2019-12-17 Hoffmann La Roche Marcadores genéticos para la predicción de respuesta a la terápia.
WO2016016157A1 (en) 2014-07-30 2016-02-04 F. Hoffmann-La Roche Ag Genetic markers for predicting responsiveness to therapy with hdl-raising or hdl mimicking agent

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2188631C2 (ru) * 1997-02-12 2002-09-10 Джапан Тобакко Инк. Ингибитор активности холестерин этерифицированного транспортного белка, профилактическое или терапевтическое средство, производные бис-(2-амидофенил)дисульфида или амидотиофенола

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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.
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
ES2460900T3 (es) * 2008-04-04 2014-05-14 F. Hoffmann-La Roche Ag Nuevo procedimiento para la preparación de derivados de ácido ciclohexanocarboxílico mediante el correspondiente derivado ciclohexanocarboxamida
BRPI0909813B1 (pt) * 2008-04-04 2018-01-02 F. Hoffmann-La Roche Ag "processos para preparação de derivados de ácido ciclo-hexanocarboxílico, e intermediário"
KR101644222B1 (ko) * 2008-06-17 2016-07-29 에프. 호프만-라 로슈 아게 약학 활성 아미드의 제조에서 중간체로서의 1-(2-에틸-부틸)-사이클로헥산카복실산 에스터

Patent Citations (1)

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RU2188631C2 (ru) * 1997-02-12 2002-09-10 Джапан Тобакко Инк. Ингибитор активности холестерин этерифицированного транспортного белка, профилактическое или терапевтическое средство, производные бис-(2-амидофенил)дисульфида или амидотиофенола

Non-Patent Citations (2)

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Title
С.Сalais et al. "Selective Reduction of Diphenyldisulfides Catalysed by Sulfides -; Influence of the Nature of the Catalyst"; Journal of Catalysis, 144, p. 160-174, 1993;Н. Shinkai "Bis(2-(Acylamino)phenyl)Disulfides, 2-(Acylamino)benzenethiols, and S-(2-(Acylamino)phenyl) Alkanethioates as Novel Inhibitors of Cholesteryl Ester Transfer Protein"; J.Med.Chem., 2000, 43, p.3566-3572;ARISAWA M ET AL: "Oxidation/reduction interconversion of thiols and disulfides using hydrogen and oxygen catalyzed by a rhodium complex", TETRAHEDRON LETTERS, vol. 46, no. 36, 2005, pages 6097-6099;CHEN RENER AND YONGMIN ZHANG: "Cleavage of S-Bond by Sm/cat.CoCl2 or Sm/cat.CoCL2.6H2O system. A novel method for the synthesis of thiolesters", SYNTHETIC COMMUNICATIONS, vol. 29, no. 21, 1999, pages 3699-3704;DAN W ET AL: "A new odorless one-pot synthesis of thioesters and selenoesters promoted by RongaliteR)", TETRAHEDRON, vol. 66, no. 37, 2010, pages 7384-7388;KESSLER, P. ET AL.: "Design and synthesis of a novel *
С.Сalais et al. "Selective Reduction of Diphenyldisulfides Catalysed by Sulfides -; Influence of the Nature of the Catalyst"; Journal of Catalysis, 144, p. 160-174, 1993;Н. Shinkai "Bis(2-(Acylamino)phenyl)Disulfides, 2-(Acylamino)benzenethiols, and S-(2-(Acylamino)phenyl) Alkanethioates as Novel Inhibitors of Cholesteryl Ester Transfer Protein"; J.Med.Chem., 2000, 43, p.3566-3572;RU 2188631 C2, 10.09.2002;ARISAWA M ET AL: "Oxidation/reduction interconversion of thiols and disulfides using hydrogen and oxygen catalyzed by a rhodium complex", TETRAHEDRON LETTERS, vol. 46, no. 36, 2005, pages 6097-6099;CHEN RENER AND YONGMIN ZHANG: "Cleavage of S-Bond by Sm/cat.CoCl2 or Sm/cat.CoCL2.6H2O system. A novel method for the synthesis of thiolesters", SYNTHETIC COMMUNICATIONS, vol. 29, no. 21, 1999, pages 3699-3704;DAN W ET AL: "A new odorless one-pot synthesis of thioesters and selenoesters promoted by RongaliteR)", TETRAHEDRON, vol. 66, no. 37, 2010, pages 7384-7388;KESSLER, P. ET AL.: "Desig *

Also Published As

Publication number Publication date
BR112013014029A2 (pt) 2016-09-13
TR201818880T4 (tr) 2019-01-21
BR112013014029B1 (pt) 2021-07-20
WO2012080178A1 (en) 2012-06-21
CA2818628C (en) 2019-02-26
JP2014510019A (ja) 2014-04-24
US8664403B2 (en) 2014-03-04
JP6054875B2 (ja) 2016-12-27
US20140171502A1 (en) 2014-06-19
US9603816B2 (en) 2017-03-28
RU2013131443A (ru) 2015-01-27
EP2651882A1 (en) 2013-10-23
MX2013006038A (es) 2013-08-01
US20120157504A1 (en) 2012-06-21
KR101947840B1 (ko) 2019-02-13
CN103261155B (zh) 2016-08-10
CA2818628A1 (en) 2012-06-21
HK1187893A1 (zh) 2014-04-17
KR20130127993A (ko) 2013-11-25
CN103261155A (zh) 2013-08-21
ES2705496T3 (es) 2019-03-25
EP2651882B1 (en) 2018-11-14

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