JP2003535887A5 - - Google Patents
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- Publication number
- JP2003535887A5 JP2003535887A5 JP2002503263A JP2002503263A JP2003535887A5 JP 2003535887 A5 JP2003535887 A5 JP 2003535887A5 JP 2002503263 A JP2002503263 A JP 2002503263A JP 2002503263 A JP2002503263 A JP 2002503263A JP 2003535887 A5 JP2003535887 A5 JP 2003535887A5
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- substituted
- phenyl
- optionally
- halogen
- 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
- 125000000217 alkyl group Chemical group 0.000 description 164
- 125000003545 alkoxy group Chemical group 0.000 description 67
- 229910052736 halogen Inorganic materials 0.000 description 44
- 125000003118 aryl group Chemical group 0.000 description 33
- 150000002367 halogens Chemical class 0.000 description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 24
- 239000001257 hydrogen Substances 0.000 description 24
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 22
- -1 2,3-dihydro -1H- indolyl Chemical group 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
- 150000002431 hydrogen Chemical class 0.000 description 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 16
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 125000002757 morpholinyl group Chemical group 0.000 description 11
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 125000005605 benzo group Chemical group 0.000 description 10
- 125000004193 piperazinyl group Chemical group 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 125000003386 piperidinyl group Chemical group 0.000 description 8
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 5
- KPKNTUUIEVXMOH-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1CCOC11CCNCC1 KPKNTUUIEVXMOH-UHFFFAOYSA-N 0.000 description 4
- 102000009346 Adenosine receptors Human genes 0.000 description 4
- 108050000203 Adenosine receptors Proteins 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- CEKSPMMCISUSTR-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydroquinoline Chemical compound C1CCC2CCCNC2=C1 CEKSPMMCISUSTR-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00113219.0 | 2000-06-21 | ||
| EP00113219 | 2000-06-21 | ||
| PCT/EP2001/006506 WO2001097786A2 (en) | 2000-06-21 | 2001-06-08 | Benzothiazole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003535887A JP2003535887A (ja) | 2003-12-02 |
| JP2003535887A5 true JP2003535887A5 (https=) | 2006-10-26 |
| JP3886897B2 JP3886897B2 (ja) | 2007-02-28 |
Family
ID=8169041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002503263A Expired - Fee Related JP3886897B2 (ja) | 2000-06-21 | 2001-06-08 | ベンゾチアゾール誘導体 |
Country Status (33)
| Country | Link |
|---|---|
| US (8) | US6521754B2 (https=) |
| EP (2) | EP1797878A3 (https=) |
| JP (1) | JP3886897B2 (https=) |
| KR (2) | KR100571161B1 (https=) |
| CN (1) | CN1234358C (https=) |
| AR (1) | AR031244A1 (https=) |
| AT (1) | ATE385794T1 (https=) |
| AU (2) | AU2001281817B2 (https=) |
| BR (1) | BR0112395A (https=) |
| CA (1) | CA2413086C (https=) |
| CY (1) | CY1107401T1 (https=) |
| CZ (1) | CZ2003182A3 (https=) |
| DE (1) | DE60132777T2 (https=) |
| DK (1) | DK1303272T3 (https=) |
| EC (1) | ECSP024399A (https=) |
| ES (1) | ES2299504T3 (https=) |
| HR (1) | HRP20020962A2 (https=) |
| HU (1) | HUP0301315A3 (https=) |
| IL (2) | IL153278A0 (https=) |
| JO (1) | JO2503B1 (https=) |
| MX (1) | MXPA02012596A (https=) |
| MY (1) | MY138352A (https=) |
| NO (2) | NO324635B1 (https=) |
| NZ (1) | NZ522928A (https=) |
| PE (1) | PE20020104A1 (https=) |
| PL (1) | PL207384B1 (https=) |
| PT (1) | PT1303272E (https=) |
| RU (1) | RU2251419C2 (https=) |
| SI (1) | SI1303272T1 (https=) |
| UY (1) | UY26782A1 (https=) |
| WO (1) | WO2001097786A2 (https=) |
| YU (1) | YU96502A (https=) |
| ZA (1) | ZA200209730B (https=) |
Families Citing this family (73)
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| AU2001281817B2 (en) * | 2000-06-21 | 2005-11-24 | F. Hoffmann-La Roche Ag | Benzothiazole derivatives |
| US6620811B2 (en) | 2001-11-19 | 2003-09-16 | Hoffmann-La Roche Inc. | Isonicotin- and nicotinamide derivatives of benzothiazoles |
| US6599901B1 (en) * | 2001-11-19 | 2003-07-29 | Hoffman-La Roche Inc. | Pyridone substituted benzothiazole derivatives |
| US6596718B1 (en) * | 2001-11-27 | 2003-07-22 | Hoffmann-La Roche Inc. | 7-Morpholin-4yl-benzothiazole amide derivatives |
| US6624163B2 (en) * | 2001-11-29 | 2003-09-23 | Hoffman-La Roche Inc. | Benzothiazole derivatives |
| US6727247B2 (en) | 2001-12-10 | 2004-04-27 | Hoffman-La Roche Inc. | Substituted benzothiazole amide derivatives |
| US6713499B2 (en) | 2001-12-12 | 2004-03-30 | Hoffman-La Roche Inc. | 7-Amino-benzothiazole derivatives |
| AU2002358597C1 (en) * | 2001-12-12 | 2008-09-18 | F. Hoffmann-La Roche Ag | Benzothiophenes as adenosine receptor modulators |
| US6734179B2 (en) | 2001-12-12 | 2004-05-11 | Hoffmann-La Roche Inc. | Benzothiazoles |
| KR101098209B1 (ko) | 2002-01-28 | 2011-12-23 | 교와 핫꼬 기린 가부시키가이샤 | 운동성 질환에 걸린 환자의 치료 방법 |
| JPWO2004002531A1 (ja) * | 2002-06-26 | 2005-10-27 | 小野薬品工業株式会社 | 血管の収縮または拡張による疾患治療剤 |
| US6958420B2 (en) * | 2002-07-19 | 2005-10-25 | Board Of Trustees Of Michigan State University | Synthesis of aminoarylboronic esters and substituted anilines from arenes via catalytic C-H activation/borylation/amination and uses thereof |
| US7338956B2 (en) | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| KR20050111306A (ko) | 2002-11-19 | 2005-11-24 | 아칠리온 파르마세우티칼스 인코포레이티드 | 바이러스 복제 억제제로서의 치환된 아릴 티오우레아 및관련 화합물 |
| AR056615A1 (es) * | 2002-12-27 | 2007-10-17 | Kyowa Hakko Kogyo Kk | Un metodo de tratamiento de trastornos de la conducta |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| MXPA05007388A (es) * | 2003-01-13 | 2005-09-12 | Hoffmann La Roche | Derivados de benzoxazol y su uso como ligandos de receptor de adenosina. |
| US6872833B2 (en) | 2003-04-14 | 2005-03-29 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| KR100710453B1 (ko) * | 2003-05-13 | 2007-04-24 | 에프. 호프만-라 로슈 아게 | 아데노신 수용체 리간드로서의 2-이미다조-벤조싸이아졸 |
| PT1636223E (pt) * | 2003-05-19 | 2008-05-06 | F Hoffmann-La Roche Ag | Derivados de benzotiazole como ligandos de receptores da adenosina |
| MXPA05012369A (es) * | 2003-05-21 | 2006-02-02 | Hoffmann La Roche | Derivados de benzotiazol y uso de los mismos en el tratamiento de enfermedades relacionadas con el receptor a2a de adenosina. |
| RU2348629C2 (ru) * | 2003-05-30 | 2009-03-10 | Ф.Хоффманн-Ля Рош Аг | Производные бензотиазола и их применение при лечении заболеваний, связанных с аденозиновыми a2a-рецепторами |
| RU2344132C2 (ru) * | 2003-06-20 | 2009-01-20 | Ф.Хоффманн-Ля Рош Аг | 2-аминобензотиазолы в качестве обратных агонистов рецепторов cb1 |
| BRPI0412502A (pt) * | 2003-07-10 | 2006-09-19 | Achillion Pharmaceuticals Inc | derivados de ariltiouréia substituìda úteis como inibidores de replicação viral |
| DE602004017316D1 (de) | 2003-07-24 | 2008-12-04 | Euro Celtique Sa | Heteroaryl-tetrahydropyridylverbindungen, die sich für die behandlung bzw. die prävention von schmerzen eignen |
| AR046078A1 (es) | 2003-08-06 | 2005-11-23 | Senomyx Inc | Nuevos sabores, modificadores de sabores, sustancias gustativas, mejoradores de gusto, sustancias gustativas y/o mejoradoras del gusto umani o dulce y uso de los mismos. |
| RU2006112847A (ru) | 2003-09-19 | 2007-11-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | Производные тиазолопиридина в качестве лигандов аденозинового рецептора |
| TW200600492A (en) * | 2004-05-18 | 2006-01-01 | Achillion Pharmaceuticals Inc | Substituted aryl acylthioureas and related compounds; inhibitors of viral replication |
| KR100834179B1 (ko) * | 2004-05-24 | 2008-05-30 | 에프. 호프만-라 로슈 아게 | 4-하이드록시-4-메틸-피페리딘-1-카복실산(4-메톡시-7-모폴린-4-일-벤조티아졸-2-일)-아마이드 |
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| JP5202946B2 (ja) * | 2004-07-22 | 2013-06-05 | エフ．ホフマン−ラ ロシュ アーゲー | ベンゾチアゾール誘導体 |
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| WO2006099972A1 (en) | 2005-03-23 | 2006-09-28 | F. Hoffmann-La Roche Ag | Acetylenyl-pyrazolo-pvrimidine derivatives as mglur2 antagonists |
| TWI370820B (en) | 2005-04-27 | 2012-08-21 | Takeda Pharmaceutical | Fused heterocyclic compounds |
| JP5048675B2 (ja) | 2005-09-27 | 2012-10-17 | エフ．ホフマン−ラ ロシュ アーゲー | ｍＧｌｕＲ２アンタゴニストとしてのオキサジアゾリルピラゾロ−ピリミジン類 |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| WO2007098826A2 (en) * | 2006-01-18 | 2007-09-07 | Siena Biotech S.P.A. | Modulators of alpha7 nicotinic acetylcholine receptors and therapeutic uses thereof |
| ES2640453T3 (es) | 2006-04-21 | 2017-11-03 | Senomyx, Inc. | Procesos para preparar composiciones saborizantes sólidas |
| US7429589B2 (en) | 2006-04-27 | 2008-09-30 | Hoffmann-La Roche Inc. | Mono-nitration of aromatic compounds via nitrate salts |
| ATE481409T1 (de) * | 2006-05-18 | 2010-10-15 | Hoffmann La Roche | Thiazolopyramidin/pyridinharnstoffderivate als antagonisten am adenosin-a2b-rezeptor |
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| JO3101B1 (ar) | 2008-12-02 | 2017-09-20 | Takeda Pharmaceuticals Co | مشتقات بنزوثيازول كعوامل مضادة للسرطان |
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| JP6836693B2 (ja) * | 2017-09-28 | 2021-03-03 | シーストーン・ファーマスーティカルズ・（スージョウ）・カンパニー・リミテッドＣｓｔｏｎｅ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ （Ｓｕｚｈｏｕ） Ｃｏ．， Ｌｔｄ． | Ａ２ａ受容体アンタゴニストとしての縮合環誘導体 |
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-
2001
- 2001-06-08 AU AU2001281817A patent/AU2001281817B2/en not_active Ceased
- 2001-06-08 EP EP07003532A patent/EP1797878A3/en not_active Withdrawn
- 2001-06-08 DE DE60132777T patent/DE60132777T2/de not_active Expired - Lifetime
- 2001-06-08 WO PCT/EP2001/006506 patent/WO2001097786A2/en not_active Ceased
- 2001-06-08 ES ES01960284T patent/ES2299504T3/es not_active Expired - Lifetime
- 2001-06-08 JP JP2002503263A patent/JP3886897B2/ja not_active Expired - Fee Related
- 2001-06-08 BR BR0112395-5A patent/BR0112395A/pt not_active IP Right Cessation
- 2001-06-08 PL PL360697A patent/PL207384B1/pl not_active IP Right Cessation
- 2001-06-08 KR KR1020027017432A patent/KR100571161B1/ko not_active Expired - Fee Related
- 2001-06-08 AT AT01960284T patent/ATE385794T1/de active
- 2001-06-08 DK DK01960284T patent/DK1303272T3/da active
- 2001-06-08 EP EP01960284A patent/EP1303272B1/en not_active Expired - Lifetime
- 2001-06-08 AU AU8181701A patent/AU8181701A/xx active Pending
- 2001-06-08 MX MXPA02012596A patent/MXPA02012596A/es active IP Right Grant
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- 2001-06-08 RU RU2003100518/15A patent/RU2251419C2/ru not_active IP Right Cessation
- 2001-06-08 PT PT01960284T patent/PT1303272E/pt unknown
- 2001-06-08 CN CNB018115349A patent/CN1234358C/zh not_active Expired - Fee Related
- 2001-06-08 NZ NZ522928A patent/NZ522928A/en unknown
- 2001-06-08 HU HU0301315A patent/HUP0301315A3/hu unknown
- 2001-06-08 HR HR20020962A patent/HRP20020962A2/xx not_active Application Discontinuation
- 2001-06-08 CZ CZ2003182A patent/CZ2003182A3/cs unknown
- 2001-06-08 YU YU96502A patent/YU96502A/sh unknown
- 2001-06-08 KR KR10-2005-7002723A patent/KR100526487B1/ko not_active Expired - Fee Related
- 2001-06-08 SI SI200130813T patent/SI1303272T1/sl unknown
- 2001-06-14 JO JO200194A patent/JO2503B1/en active
- 2001-06-14 US US09/881,252 patent/US6521754B2/en not_active Expired - Fee Related
- 2001-06-18 PE PE2001000587A patent/PE20020104A1/es not_active Application Discontinuation
- 2001-06-19 AR ARP010102899A patent/AR031244A1/es unknown
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- 2001-06-20 UY UY26782A patent/UY26782A1/es not_active Application Discontinuation
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2002
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- 2002-12-04 IL IL153278A patent/IL153278A/en not_active IP Right Cessation
- 2002-12-05 US US10/310,508 patent/US6835732B2/en not_active Expired - Fee Related
- 2002-12-12 NO NO20025978A patent/NO324635B1/no not_active IP Right Cessation
- 2002-12-18 US US10/322,272 patent/US6963000B2/en not_active Expired - Fee Related
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2004
- 2004-08-30 US US10/930,361 patent/US20050026906A1/en not_active Abandoned
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2005
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2007
- 2007-07-06 NO NO20073465A patent/NO20073465L/no not_active Application Discontinuation
- 2007-10-31 US US11/930,717 patent/US20080125419A1/en not_active Abandoned
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2008
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