RU2004117525A - Применение производных 2-амино-4-гетероариэтилтиазолина в качестве ингибиторов индуцибельной no-синтазы - Google Patents
Применение производных 2-амино-4-гетероариэтилтиазолина в качестве ингибиторов индуцибельной no-синтазы Download PDFInfo
- Publication number
- RU2004117525A RU2004117525A RU2004117525/04A RU2004117525A RU2004117525A RU 2004117525 A RU2004117525 A RU 2004117525A RU 2004117525/04 A RU2004117525/04 A RU 2004117525/04A RU 2004117525 A RU2004117525 A RU 2004117525A RU 2004117525 A RU2004117525 A RU 2004117525A
- Authority
- RU
- Russia
- Prior art keywords
- ethyl
- formula
- compound
- ylamine
- thiazol
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (12)
1. Соединение формулы (I)
где Het означает 2-тиенильный, 3-тиенильный, 2-пиримидильный, 5-пиримидильный, 2-пиридильный, 3-пиридильный, 4-пиридильный, 2-тиазолильный, 4-тиазолильный или 5-тиазолильный радикал
его рацемические смеси, энантиомеры, диастереоизомеры и их смеси, его таутомеры, а также их фармацевтически приемлемые соли.
2. Соединение по п.1, где соединением формулы (I) является одно из следующих соединений:
4-(2-пиридин-2-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
4-(2-пиридин-3-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
4-(2-пиридин-4-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
4-(2-тиен-3-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
их рацемические смеси, энантиомеры, диастереоизомеры и их смеси, его таутомеры, а также их фармацевтически приемлемые соли.
3. Соединение по пп.1 и 2, где соединением формулы (I) является одно из следующих соединений:
(+)-(4R)-4-(2-пиридин-2-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
(+)-(4R)-4-(2-пиридин-3-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
(+)-(4R)-4-(2-пиридин-4-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
(4R)-4-(2-тиен-3-илэтил)-4,5-дигидро-1,3-тиазол-2-иламин
их таутомеры, а также их фармацевтически приемлемые соли.
4. Соединение по пп.1-3 для применения в качестве лекарственного препарата.
5. Фармацевтическая композиция, содержащая соединение по пп.1-3 в фармацевтически приемлемой среде.
6. Лекарственный препарат по п.4, который содержит по крайней мере одно соединение по пп.1-3, для терапевтического применения при лечении заболеваний, при которых происходит аномальное образование оксида азота (NO) в результате индукции индуцибельной NO-синтазы (NOS-2).
7. Лекарственный препарат по п.4, который содержит по крайней мере одно соединение по пп.1-3, для терапевтического применения при лечении болезни Паркинсона.
8. Способ получения соединений формулы (I), определенных по п.1, включающий стадию циклизации производного формулы
где Het имеет значения, определенные в п.1, и необязательное превращение продукта в его фармацевтически приемлемую соль.
9. Способ получения по п.8, в котором циклизацию проводят в кислой среде при температуре около 100°С.
10. Способ получения по п.9, в котором в качестве кислой среды предпочтительно используют 6N хлористоводородную кислоту.
11. Способ получения соединений формулы (II), в которой Het имеет значения, определенные в п.1, включающий стадию взаимодействия соединения формулы (IIa)
в которой Ra является защитной группой функции амина, а Rb - защитной группой функции -аминоспирта, с производным бора и X-Het с получением соединения формулы (IIb)
которое подвергают взаимодействию с веществом, снимающим защиту, с получением соединения формулы (IIc)
которое подвергают взаимодействию с трет-бутилизотиоцианатом, с получением соединения формулы (II)
12. N-(трет-бутил)-N'-[(1R)-2-гидрокси-1-(2-тиен-3-илэтил)этил]тиомочевина, гидрохлорид (2R)-2-амино-4-(3-тиенил)-1-бутанола, трет-бутил-(4R)-2,2-диметил-4-(2-тиен-3-илэтил)оксазолидин-3-карбоксилат в качестве промежуточных соединений.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0114509A FR2832151B1 (fr) | 2001-11-09 | 2001-11-09 | Utilisation de derives de 2-amino-4-heteroarylethyl-thiazoline comme inhibiteurs de no-synthase inductible |
| FR01/14509 | 2001-11-09 | ||
| US35297702P | 2002-01-30 | 2002-01-30 | |
| US60/352,977 | 2002-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2004117525A true RU2004117525A (ru) | 2005-04-20 |
Family
ID=26213259
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004117525/04A RU2004117525A (ru) | 2001-11-09 | 2002-11-07 | Применение производных 2-амино-4-гетероариэтилтиазолина в качестве ингибиторов индуцибельной no-синтазы |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6872740B2 (ru) |
| EP (1) | EP1446402B1 (ru) |
| JP (1) | JP4365681B2 (ru) |
| AT (1) | ATE308541T1 (ru) |
| AU (1) | AU2002358874B2 (ru) |
| BR (1) | BR0206363A (ru) |
| CA (1) | CA2465691C (ru) |
| DE (1) | DE60207104T2 (ru) |
| DK (1) | DK1446402T3 (ru) |
| ES (1) | ES2250731T3 (ru) |
| HR (1) | HRP20040401A2 (ru) |
| HU (1) | HUP0402038A2 (ru) |
| IL (2) | IL161842A0 (ru) |
| MA (1) | MA27077A1 (ru) |
| MX (1) | MXPA04003766A (ru) |
| NO (1) | NO20033130L (ru) |
| PL (1) | PL370322A1 (ru) |
| RU (1) | RU2004117525A (ru) |
| WO (1) | WO2003040142A1 (ru) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL161841A0 (en) * | 2001-11-09 | 2005-11-20 | Aventis Pharma Sa | 2-Amino-thiazoline derivatives and their use as inhibitors of inducible no-synthase |
| EP1942105B8 (en) * | 2005-10-25 | 2014-08-13 | Shionogi&Co., Ltd. | Aminodihydrothiazine derivative |
| US8653067B2 (en) | 2007-04-24 | 2014-02-18 | Shionogi & Co., Ltd. | Pharmaceutical composition for treating Alzheimer's disease |
| KR20100017255A (ko) | 2007-04-24 | 2010-02-16 | 시오노기 앤드 컴파니, 리미티드 | 환식기로 치환된 아미노다이하이드로싸이아진 유도체 |
| US8637504B2 (en) | 2008-06-13 | 2014-01-28 | Shionogi & Co., Ltd. | Sulfur-containing heterocyclic derivative having beta secretase inhibitory activity |
| EP2360155A4 (en) | 2008-10-22 | 2012-06-20 | Shionogi & Co | 2-AMINOPYRIDIN-4-ON AND 2-AMINOPYRIDINE DERIVATIVE WITH BACE1-HEMDERING EFFECT |
| RU2012129168A (ru) | 2009-12-11 | 2014-01-20 | Сионоги Энд Ко. Лтд. | Производные оксазина |
| CA2816285A1 (en) | 2010-10-29 | 2012-05-03 | Shionogi & Co., Ltd. | Naphthyridine derivative |
| JP5766198B2 (ja) | 2010-10-29 | 2015-08-19 | 塩野義製薬株式会社 | 縮合アミノジヒドロピリミジン誘導体 |
| CN103608345A (zh) | 2011-04-26 | 2014-02-26 | 盐野义制药株式会社 | 噁嗪衍生物和含有该噁嗪衍生物的bace1抑制剂 |
| WO2014065434A1 (en) | 2012-10-24 | 2014-05-01 | Shionogi & Co., Ltd. | Dihydrooxazine or oxazepine derivatives having bace1 inhibitory activity |
| WO2016064009A1 (ko) * | 2014-10-24 | 2016-04-28 | 한국해양과학기술원 | 라말린을 함유하는 퇴행성 뇌질환의 예방 또는 치료용 조성물 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL107771A0 (en) * | 1992-11-27 | 1994-02-27 | Wellcome Found | Pharmaceutical compositions containing isothiourea derivatives certain such novel compounds and their preparation |
| EP0897912A1 (en) * | 1993-10-21 | 1999-02-24 | G.D. Searle & Co. | Amidino derivatives useful as nitric oxide synthase inhibitors |
| WO1996014842A1 (en) * | 1994-11-15 | 1996-05-23 | Merck & Co., Inc. | Substituted heterocycles as inhibitors of nitric oxide synthase |
| FR2810037B1 (fr) * | 2000-06-09 | 2004-04-23 | Aventis Pharma Sa | Utilisation de derives de 2-aminothiazoline comme inhibiteurs de no-synthase inductible |
-
2002
- 2002-11-07 BR BR0206363-8A patent/BR0206363A/pt not_active Application Discontinuation
- 2002-11-07 AU AU2002358874A patent/AU2002358874B2/en not_active Ceased
- 2002-11-07 AT AT02793211T patent/ATE308541T1/de active
- 2002-11-07 JP JP2003542188A patent/JP4365681B2/ja not_active Expired - Fee Related
- 2002-11-07 DK DK02793211T patent/DK1446402T3/da active
- 2002-11-07 IL IL16184202A patent/IL161842A0/xx unknown
- 2002-11-07 RU RU2004117525/04A patent/RU2004117525A/ru not_active Application Discontinuation
- 2002-11-07 ES ES02793211T patent/ES2250731T3/es not_active Expired - Lifetime
- 2002-11-07 HU HU0402038A patent/HUP0402038A2/hu unknown
- 2002-11-07 EP EP02793211A patent/EP1446402B1/fr not_active Expired - Lifetime
- 2002-11-07 DE DE60207104T patent/DE60207104T2/de not_active Expired - Lifetime
- 2002-11-07 WO PCT/FR2002/003809 patent/WO2003040142A1/fr active IP Right Grant
- 2002-11-07 MX MXPA04003766A patent/MXPA04003766A/es active IP Right Grant
- 2002-11-07 PL PL02370322A patent/PL370322A1/xx unknown
- 2002-11-07 CA CA2465691A patent/CA2465691C/fr not_active Expired - Fee Related
- 2002-11-08 US US10/291,110 patent/US6872740B2/en not_active Expired - Fee Related
-
2003
- 2003-07-08 NO NO20033130A patent/NO20033130L/no unknown
-
2004
- 2004-04-22 MA MA27645A patent/MA27077A1/fr unknown
- 2004-05-06 HR HR20040401A patent/HRP20040401A2/hr not_active Application Discontinuation
- 2004-05-06 IL IL161842A patent/IL161842A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2465691A1 (fr) | 2003-05-15 |
| PL370322A1 (en) | 2005-05-16 |
| ES2250731T3 (es) | 2006-04-16 |
| HUP0402038A2 (hu) | 2005-01-28 |
| IL161842A (en) | 2010-12-30 |
| ATE308541T1 (de) | 2005-11-15 |
| AU2002358874B2 (en) | 2007-09-06 |
| JP2005509651A (ja) | 2005-04-14 |
| MA27077A1 (fr) | 2004-12-20 |
| EP1446402A1 (fr) | 2004-08-18 |
| NO20033130D0 (no) | 2003-07-08 |
| US20030225140A1 (en) | 2003-12-04 |
| CA2465691C (fr) | 2011-07-19 |
| MXPA04003766A (es) | 2004-07-29 |
| BR0206363A (pt) | 2003-12-23 |
| US6872740B2 (en) | 2005-03-29 |
| DE60207104T2 (de) | 2006-07-13 |
| DE60207104D1 (de) | 2005-12-08 |
| JP4365681B2 (ja) | 2009-11-18 |
| DK1446402T3 (da) | 2006-03-06 |
| HRP20040401A2 (en) | 2004-10-31 |
| NO20033130L (no) | 2003-08-27 |
| EP1446402B1 (fr) | 2005-11-02 |
| IL161842A0 (en) | 2005-11-20 |
| WO2003040142A1 (fr) | 2003-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20070116 |