JP2005517634A5 - - Google Patents
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- Publication number
- JP2005517634A5 JP2005517634A5 JP2003541738A JP2003541738A JP2005517634A5 JP 2005517634 A5 JP2005517634 A5 JP 2005517634A5 JP 2003541738 A JP2003541738 A JP 2003541738A JP 2003541738 A JP2003541738 A JP 2003541738A JP 2005517634 A5 JP2005517634 A5 JP 2005517634A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- pyridin
- ylamine
- thiazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 26
- 238000000034 method Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 6
- 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
- 230000002378 acidificating effect Effects 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 238000007363 ring formation reaction Methods 0.000 claims 3
- -1 2,6-dichloro-pyridin-4-ylmethyl Chemical group 0.000 claims 2
- ZFWFRTVIIMTOLY-UHFFFAOYSA-N 2-isothiocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=S ZFWFRTVIIMTOLY-UHFFFAOYSA-N 0.000 claims 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000012351 deprotecting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000000203 mixture Substances 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
- 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 1
- 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 1
- RKHSTYMJTVGDPA-UHFFFAOYSA-N ClC1=NC=CC(=C1)CC1N=C(SC1)N.OC1=NC=CC(=C1)CC1N=C(SC1)N Chemical compound ClC1=NC=CC(=C1)CC1N=C(SC1)N.OC1=NC=CC(=C1)CC1N=C(SC1)N RKHSTYMJTVGDPA-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims 1
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 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
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 1
- 0 *c1cc(CC2N=C(N)SC2)cc(*)n1 Chemical compound *c1cc(CC2N=C(N)SC2)cc(*)n1 0.000 description 9
- ORLRPBBRJUPSCA-UHFFFAOYSA-N COc1cc(CC(CO)N)ccn1 Chemical compound COc1cc(CC(CO)N)ccn1 ORLRPBBRJUPSCA-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| 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 |
| US35297802P | 2002-01-30 | 2002-01-30 | |
| PCT/FR2002/003808 WO2003039446A2 (fr) | 2001-11-09 | 2002-11-07 | Derives de 2-amino-4-pyridylmethyl-thiazoline et leur utilisation comme inhibiteurs de no-synthase inductible |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005517634A JP2005517634A (ja) | 2005-06-16 |
| JP2005517634A5 true JP2005517634A5 (enExample) | 2006-01-05 |
| JP4342309B2 JP4342309B2 (ja) | 2009-10-14 |
Family
ID=26213258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003541738A Expired - Fee Related JP4342309B2 (ja) | 2001-11-09 | 2002-11-07 | 誘導型ｎｏ−シンターゼ阻害剤としての２−アミノ−４−ピリジルメチル−チアゾリン誘導体の使用 |
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) |
Families Citing this family (11)
| 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 |
| RU2416603C9 (ru) * | 2005-10-25 | 2012-06-20 | Сионоги Энд Ко., Лтд. | Производные аминодигидротиазина |
| WO2008133273A1 (ja) | 2007-04-24 | 2008-11-06 | Shionogi & Co., Ltd. | アルツハイマー症治療用医薬組成物 |
| TW200902526A (en) | 2007-04-24 | 2009-01-16 | Shionogi & Amp Co Ltd | Aminodihydrothiazin derivative substituted with a cyclic group |
| AU2009258496B8 (en) | 2008-06-13 | 2014-06-26 | Shionogi & Co., Ltd. | Sulfur-containing heterocyclic derivative having beta-secretase-inhibiting activity |
| US8703785B2 (en) | 2008-10-22 | 2014-04-22 | Shionogi & Co., Ltd. | 2-aminopyrimidin-4-one and 2-aminopyridine derivatives both having BACE1-inhibiting activity |
| KR20120104570A (ko) | 2009-12-11 | 2012-09-21 | 시오노기세야쿠 가부시키가이샤 | 옥사진 유도체 |
| US9018219B2 (en) | 2010-10-29 | 2015-04-28 | Shionogi & Co., Ltd. | Fused aminodihydropyrimidine derivative |
| EP2634186A4 (en) | 2010-10-29 | 2014-03-26 | Shionogi & Co | naphthyridine |
| EP2703399A4 (en) | 2011-04-26 | 2014-10-15 | Shionogi & Co | OXAZINE DERIVATIVE AND BACE-1 HEMMER THEREOF |
| WO2014065434A1 (en) | 2012-10-24 | 2014-05-01 | Shionogi & Co., Ltd. | Dihydrooxazine or oxazepine derivatives having bace1 inhibitory activity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5533094A (en) * | 1992-11-27 | 1994-06-22 | Wellcome Foundation Limited, The | Enzyme inhibitors |
| CA2173468A1 (en) * | 1993-10-21 | 1995-04-27 | Donald W. Hansen, Jr. | 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 HU HU0402033A patent/HUP0402033A2/hu unknown
- 2002-11-07 MX MXPA04004213A patent/MXPA04004213A/es active IP Right Grant
- 2002-11-07 PL PL02370267A patent/PL370267A1/xx unknown
- 2002-11-07 HR HR20040402A patent/HRP20040402A2/hr not_active Application Discontinuation
- 2002-11-07 RU RU2004117531/04A patent/RU2004117531A/ru not_active Application Discontinuation
- 2002-11-07 AT AT02793210T patent/ATE446295T1/de active
- 2002-11-07 DE DE60234117T patent/DE60234117D1/de not_active Expired - Lifetime
- 2002-11-07 CA CA002465877A patent/CA2465877C/fr not_active Expired - Fee Related
- 2002-11-07 PT PT02793210T patent/PT1450750E/pt unknown
- 2002-11-07 DK DK02793210.2T patent/DK1450750T3/da active
- 2002-11-07 BR BR0206368-9A patent/BR0206368A/pt not_active Application Discontinuation
- 2002-11-07 WO PCT/FR2002/003808 patent/WO2003039446A2/fr not_active Ceased
- 2002-11-07 IL IL16184302A patent/IL161843A0/xx unknown
- 2002-11-07 ES ES02793210T patent/ES2335090T3/es not_active Expired - Lifetime
- 2002-11-07 JP JP2003541738A patent/JP4342309B2/ja not_active Expired - Fee Related
- 2002-11-07 CN CNB028246934A patent/CN1288153C/zh not_active Expired - Fee Related
- 2002-11-07 SI SI200230869T patent/SI1450750T1/sl unknown
- 2002-11-07 EP EP02793210A patent/EP1450750B1/fr not_active Expired - Lifetime
- 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
-
2010
- 2010-01-20 CY CY20101100056T patent/CY1110284T1/el unknown
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