RU2004117531A - Использование производных 2-амино-4-пиридилметилтиазолина в качестве ингибиторов индуцибельной no-синтазы - Google Patents
Использование производных 2-амино-4-пиридилметилтиазолина в качестве ингибиторов индуцибельной no-синтазы Download PDFInfo
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- RU2004117531A RU2004117531A RU2004117531/04A RU2004117531A RU2004117531A RU 2004117531 A RU2004117531 A RU 2004117531A RU 2004117531/04 A RU2004117531/04 A RU 2004117531/04A RU 2004117531 A RU2004117531 A RU 2004117531A RU 2004117531 A RU2004117531 A RU 2004117531A
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- IKEKITJRHMNIAR-UHFFFAOYSA-N 4-(4,5-dihydro-1,3-thiazol-2-ylmethyl)pyridin-2-amine Chemical class C1=NC(N)=CC(CC=2SCCN=2)=C1 IKEKITJRHMNIAR-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims abstract 2
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 27
- 238000004519 manufacturing process Methods 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 230000002378 acidificating effect Effects 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 238000007363 ring formation reaction Methods 0.000 claims 3
- ZFWFRTVIIMTOLY-UHFFFAOYSA-N 2-isothiocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=S ZFWFRTVIIMTOLY-UHFFFAOYSA-N 0.000 claims 2
- AFSMPSWJLWLVRZ-UHFFFAOYSA-N 4-[(2,6-dichloropyridin-4-yl)methyl]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CC(Cl)=NC(Cl)=C1 AFSMPSWJLWLVRZ-UHFFFAOYSA-N 0.000 claims 2
- FFUZLEWYSSBPMD-UHFFFAOYSA-N 4-[(2-amino-4,5-dihydro-1,3-thiazol-4-yl)methyl]-1h-pyridin-2-one Chemical compound C1SC(N)=NC1CC1=CC(=O)NC=C1 FFUZLEWYSSBPMD-UHFFFAOYSA-N 0.000 claims 2
- WMLQASNJNMSSIQ-UHFFFAOYSA-N 4-[(2-chloropyridin-4-yl)methyl]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CC=NC(Cl)=C1 WMLQASNJNMSSIQ-UHFFFAOYSA-N 0.000 claims 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- LOIXGAFDHPJCOX-UHFFFAOYSA-N 1-tert-butyl-3-[1-hydroxy-3-(3-methoxypyridin-4-yl)propan-2-yl]thiourea Chemical compound COC1=CN=CC=C1CC(CO)NC(=S)NC(C)(C)C LOIXGAFDHPJCOX-UHFFFAOYSA-N 0.000 claims 1
- FOHBDXAVIIQJCG-UHFFFAOYSA-N 2-amino-3-(3-methoxypyridin-4-yl)propan-1-ol Chemical compound COC1=CN=CC=C1CC(N)CO FOHBDXAVIIQJCG-UHFFFAOYSA-N 0.000 claims 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- -1 N- [1- (tert-butyldimethylsilanyloxymethyl) -2- (1-hydroxypyridin-4-yl) ethyl] acetamide Chemical compound 0.000 claims 1
- RRUFGPFIROXSIS-UHFFFAOYSA-N N-[3-tert-butylsilyloxy-1-(3-methoxypyridin-4-yl)-3-methylbutan-2-yl]acetamide Chemical compound C(C)(C)(C)[SiH2]OC(C(CC1=C(C=NC=C1)OC)NC(C)=O)(C)C RRUFGPFIROXSIS-UHFFFAOYSA-N 0.000 claims 1
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims 1
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000006698 induction Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 239000000460 chlorine Substances 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 0 COc1cc(CC(*)CO*)ccn1 Chemical compound COc1cc(CC(*)CO*)ccn1 0.000 description 1
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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- 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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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0114508A FR2832150B1 (fr) | 2001-11-09 | 2001-11-09 | Utilisation de derives de 2-amino-4-pyridylmethyl-thiazoline comme inhibiteurs de no-synthase inductible |
| FR01/14508 | 2001-11-09 | ||
| US35297802P | 2002-01-30 | 2002-01-30 | |
| US60/352,978 | 2002-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2004117531A true RU2004117531A (ru) | 2005-04-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004117531/04A RU2004117531A (ru) | 2001-11-09 | 2002-11-07 | Использование производных 2-амино-4-пиридилметилтиазолина в качестве ингибиторов индуцибельной no-синтазы |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6762196B2 (enExample) |
| EP (1) | EP1450750B1 (enExample) |
| JP (1) | JP4342309B2 (enExample) |
| CN (1) | CN1288153C (enExample) |
| AT (1) | ATE446295T1 (enExample) |
| BR (1) | BR0206368A (enExample) |
| CA (1) | CA2465877C (enExample) |
| CY (1) | CY1110284T1 (enExample) |
| DE (1) | DE60234117D1 (enExample) |
| DK (1) | DK1450750T3 (enExample) |
| ES (1) | ES2335090T3 (enExample) |
| HR (1) | HRP20040402A2 (enExample) |
| HU (1) | HUP0402033A2 (enExample) |
| IL (2) | IL161843A0 (enExample) |
| MA (1) | MA27143A1 (enExample) |
| MX (1) | MXPA04004213A (enExample) |
| NO (1) | NO20033131L (enExample) |
| PL (1) | PL370267A1 (enExample) |
| PT (1) | PT1450750E (enExample) |
| RU (1) | RU2004117531A (enExample) |
| SI (1) | SI1450750T1 (enExample) |
| WO (1) | WO2003039446A2 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2416603C2 (ru) * | 2005-10-25 | 2011-04-20 | Сионоги Энд Ко., Лтд. | Производные аминодигидротиазина |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10240735A1 (de) * | 2002-08-29 | 2004-03-18 | Eberhard-Karls-Universität Tübingen Universitätsklinikum | Verwendung von Modulatoren der NO-Signalkaskade und pharmazeutische Zusammensetzung |
| AU2008245082B8 (en) | 2007-04-24 | 2012-09-13 | Shionogi & Co., Ltd. | Aminodihydrothiazine derivatives substituted with a cyclic group |
| EP2151435A4 (en) | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| US8637504B2 (en) | 2008-06-13 | 2014-01-28 | Shionogi & Co., Ltd. | Sulfur-containing heterocyclic derivative having beta secretase inhibitory activity |
| WO2010047372A1 (ja) | 2008-10-22 | 2010-04-29 | 塩野義製薬株式会社 | Ｂａｃｅ１阻害活性を有する２－アミノピリミジン－４－オンおよび２－アミノピリジン誘導体 |
| RU2012129168A (ru) | 2009-12-11 | 2014-01-20 | Сионоги Энд Ко. Лтд. | Производные оксазина |
| US9018219B2 (en) | 2010-10-29 | 2015-04-28 | Shionogi & Co., Ltd. | Fused aminodihydropyrimidine derivative |
| CA2816285A1 (en) | 2010-10-29 | 2012-05-03 | Shionogi & Co., Ltd. | Naphthyridine derivative |
| WO2012147763A1 (ja) | 2011-04-26 | 2012-11-01 | 塩野義製薬株式会社 | オキサジン誘導体およびそれを含有するｂａｃｅ１阻害剤 |
| JP2016501827A (ja) | 2012-10-24 | 2016-01-21 | 塩野義製薬株式会社 | Ｂａｃｅ１阻害作用を有するジヒドロオキサジンまたはオキサゼピン誘導体 |
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 |
| AU688811B2 (en) * | 1993-10-21 | 1998-03-19 | 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 RU RU2004117531/04A patent/RU2004117531A/ru not_active Application Discontinuation
- 2002-11-07 SI SI200230869T patent/SI1450750T1/sl unknown
- 2002-11-07 PT PT02793210T patent/PT1450750E/pt unknown
- 2002-11-07 JP JP2003541738A patent/JP4342309B2/ja not_active Expired - Fee Related
- 2002-11-07 HR HR20040402A patent/HRP20040402A2/hr not_active Application Discontinuation
- 2002-11-07 CN CNB028246934A patent/CN1288153C/zh not_active Expired - Fee Related
- 2002-11-07 DE DE60234117T patent/DE60234117D1/de not_active Expired - Lifetime
- 2002-11-07 IL IL16184302A patent/IL161843A0/xx unknown
- 2002-11-07 WO PCT/FR2002/003808 patent/WO2003039446A2/fr not_active Ceased
- 2002-11-07 CA CA002465877A patent/CA2465877C/fr not_active Expired - Fee Related
- 2002-11-07 EP EP02793210A patent/EP1450750B1/fr not_active Expired - Lifetime
- 2002-11-07 AT AT02793210T patent/ATE446295T1/de active
- 2002-11-07 BR BR0206368-9A patent/BR0206368A/pt not_active Application Discontinuation
- 2002-11-07 DK DK02793210.2T patent/DK1450750T3/da active
- 2002-11-07 ES ES02793210T patent/ES2335090T3/es not_active Expired - Lifetime
- 2002-11-07 MX MXPA04004213A patent/MXPA04004213A/es active IP Right Grant
- 2002-11-07 HU HU0402033A patent/HUP0402033A2/hu unknown
- 2002-11-07 PL PL02370267A patent/PL370267A1/xx unknown
- 2002-11-08 US US10/290,624 patent/US6762196B2/en not_active Expired - Fee Related
-
2003
- 2003-07-08 NO NO20033131A patent/NO20033131L/no unknown
-
2004
- 2004-04-22 MA MA27644A patent/MA27143A1/fr unknown
- 2004-05-06 IL IL161843A patent/IL161843A/en not_active IP Right Cessation
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2010
- 2010-01-20 CY CY20101100056T patent/CY1110284T1/el unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2416603C2 (ru) * | 2005-10-25 | 2011-04-20 | Сионоги Энд Ко., Лтд. | Производные аминодигидротиазина |
| RU2416603C9 (ru) * | 2005-10-25 | 2012-06-20 | Сионоги Энд Ко., Лтд. | Производные аминодигидротиазина |
Also Published As
| Publication number | Publication date |
|---|---|
| PL370267A1 (en) | 2005-05-16 |
| CA2465877C (fr) | 2009-12-29 |
| WO2003039446A3 (fr) | 2003-11-27 |
| MXPA04004213A (es) | 2004-07-08 |
| SI1450750T1 (sl) | 2010-02-26 |
| CA2465877A1 (fr) | 2003-05-15 |
| IL161843A (en) | 2011-08-31 |
| CN1602311A (zh) | 2005-03-30 |
| NO20033131L (no) | 2003-08-27 |
| ES2335090T3 (es) | 2010-03-22 |
| HUP0402033A2 (hu) | 2005-02-28 |
| BR0206368A (pt) | 2004-02-10 |
| EP1450750B1 (fr) | 2009-10-21 |
| WO2003039446A2 (fr) | 2003-05-15 |
| ATE446295T1 (de) | 2009-11-15 |
| CY1110284T1 (el) | 2015-01-14 |
| US20030153605A1 (en) | 2003-08-14 |
| NO20033131D0 (no) | 2003-07-08 |
| CN1288153C (zh) | 2006-12-06 |
| US6762196B2 (en) | 2004-07-13 |
| HRP20040402A2 (en) | 2004-10-31 |
| PT1450750E (pt) | 2010-01-18 |
| JP2005517634A (ja) | 2005-06-16 |
| EP1450750A2 (fr) | 2004-09-01 |
| DK1450750T3 (da) | 2010-03-08 |
| JP4342309B2 (ja) | 2009-10-14 |
| DE60234117D1 (de) | 2009-12-03 |
| MA27143A1 (fr) | 2005-01-03 |
| IL161843A0 (en) | 2005-11-20 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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