RU2607636C2 - Способ получения ароматических тиольных производных при гидрировании дисульфидов - Google Patents
Способ получения ароматических тиольных производных при гидрировании дисульфидов Download PDFInfo
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- 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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- compound
- solvent
- transition metal
- hydrogenation catalyst
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- 238000000034 method Methods 0.000 title claims abstract description 41
- -1 aromatic thiol Chemical class 0.000 title claims abstract description 31
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
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- 239000003054 catalyst Substances 0.000 claims abstract description 50
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 42
- 150000003624 transition metals Chemical class 0.000 claims abstract description 42
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 17
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 12
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 10
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 10
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- 239000011159 matrix material Substances 0.000 claims abstract description 8
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 42
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- 239000002904 solvent Substances 0.000 claims description 29
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
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- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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 |
|---|---|
| RU2013131443A RU2013131443A (ru) | 2015-01-27 |
| RU2607636C2 true RU2607636C2 (ru) | 2017-01-10 |
Family
ID=43877331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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)
| 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 |
Citations (1)
| 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 |
Family Cites Families (10)
| 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. |
| 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
Patent Citations (1)
| 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 |
Non-Patent Citations (2)
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 |
| CA2818628A1 (en) | 2012-06-21 |
| MX2013006038A (es) | 2013-08-01 |
| EP2651882A1 (en) | 2013-10-23 |
| CA2818628C (en) | 2019-02-26 |
| 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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