JP2005500276A5 - - Google Patents
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- Publication number
- JP2005500276A5 JP2005500276A5 JP2003501465A JP2003501465A JP2005500276A5 JP 2005500276 A5 JP2005500276 A5 JP 2005500276A5 JP 2003501465 A JP2003501465 A JP 2003501465A JP 2003501465 A JP2003501465 A JP 2003501465A JP 2005500276 A5 JP2005500276 A5 JP 2005500276A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- substituted
- alkyl
- oxide
- group
- 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 55
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 150000002148 esters Chemical class 0.000 claims 24
- 239000000651 prodrug Substances 0.000 claims 24
- 229940002612 prodrug Drugs 0.000 claims 24
- 150000001204 N-oxides Chemical class 0.000 claims 23
- -1 cycloalkenylalkyl Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 12
- 239000012453 solvate Substances 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 229910005965 SO 2 Inorganic materials 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- 230000001668 ameliorated effect Effects 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 230000021164 cell adhesion Effects 0.000 claims 5
- 239000003112 inhibitor Substances 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- AFEUKQVCYGQKJX-UHFFFAOYSA-N N1=CC=C(C=C1)C(CC)C1=CC=C2CCNC(C2=C1)C(CC1=CC2=C(N=C(O2)NC2=C(C=CC=C2)C)C=C1)=O Chemical compound N1=CC=C(C=C1)C(CC)C1=CC=C2CCNC(C2=C1)C(CC1=CC2=C(N=C(O2)NC2=C(C=CC=C2)C)C=C1)=O AFEUKQVCYGQKJX-UHFFFAOYSA-N 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000524 functional group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical group NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 150000001555 benzenes Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 claims 1
- ODIXWOUERPQZJO-UHFFFAOYSA-N 2-[5-[[2-[3-methoxy-4-[(2-methylphenyl)carbamoylamino]phenyl]acetyl]amino]-1,2,3,4-tetrahydroisoquinolin-8-yl]butanoic acid Chemical compound C1=2CCNCC=2C(C(C(O)=O)CC)=CC=C1NC(=O)CC(C=C1OC)=CC=C1NC(=O)NC1=CC=CC=C1C ODIXWOUERPQZJO-UHFFFAOYSA-N 0.000 claims 1
- OVBZKBCLTOLCGV-UHFFFAOYSA-N 3-[1-[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]-1,2,3,4-tetrahydroisoquinolin-6-yl]-3-phenylpropanoic acid Chemical compound CC1=CC=CC=C1NC(OC1=C2)=NC1=CC=C2CC(=O)C1C2=CC=C(C(CC(O)=O)C=3C=CC=CC=3)C=C2CCN1 OVBZKBCLTOLCGV-UHFFFAOYSA-N 0.000 claims 1
- BRFHNNYFEPESTQ-UHFFFAOYSA-N 3-[1-[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]-1,2,3,4-tetrahydroisoquinolin-7-yl]-3-phenylpropanoic acid Chemical compound CC1=CC=CC=C1NC(OC1=C2)=NC1=CC=C2CC(=O)C1C2=CC(C(CC(O)=O)C=3C=CC=CC=3)=CC=C2CCN1 BRFHNNYFEPESTQ-UHFFFAOYSA-N 0.000 claims 1
- YQMAMHSQQSBGDZ-UHFFFAOYSA-N 3-[1-[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]-1,2,3,4-tetrahydroisoquinolin-7-yl]butanoic acid Chemical compound C12=CC(C(CC(O)=O)C)=CC=C2CCNC1C(=O)CC(C=C1O2)=CC=C1N=C2NC1=CC=CC=C1C YQMAMHSQQSBGDZ-UHFFFAOYSA-N 0.000 claims 1
- TVZXLIZVCREAPF-UHFFFAOYSA-N 3-[1-[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]-1,2,3,4-tetrahydroisoquinolin-8-yl]but-2-enoic acid Chemical compound C1=2C(C(=CC(O)=O)C)=CC=CC=2CCNC1C(=O)CC(C=C1O2)=CC=C1N=C2NC1=CC=CC=C1C TVZXLIZVCREAPF-UHFFFAOYSA-N 0.000 claims 1
- RIDVBCDNWSGWQZ-UHFFFAOYSA-N 3-[1-[2-[4-methyl-2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]-1,2,3,4-tetrahydroisoquinolin-6-yl]butanoic acid Chemical compound N1CCC2=CC(C(CC(O)=O)C)=CC=C2C1C(=O)CC(C=C1O2)=CC(C)=C1N=C2NC1=CC=CC=C1C RIDVBCDNWSGWQZ-UHFFFAOYSA-N 0.000 claims 1
- LDNGPIKDGKYJOE-UHFFFAOYSA-N 3-[2-[2-(2-methylanilino)-1,3-benzoxazole-6-carbonyl]-3,4-dihydro-1h-isoquinolin-6-yl]butanoic acid Chemical compound C1CC2=CC(C(CC(O)=O)C)=CC=C2CN1C(=O)C(C=C1O2)=CC=C1N=C2NC1=CC=CC=C1C LDNGPIKDGKYJOE-UHFFFAOYSA-N 0.000 claims 1
- GRYXVSHAAMIBGD-UHFFFAOYSA-N 3-cyclohexyl-3-[1-[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]-1,2,3,4-tetrahydroisoquinolin-6-yl]propanoic acid Chemical compound CC1=CC=CC=C1NC(OC1=C2)=NC1=CC=C2CC(=O)C1C2=CC=C(C(CC(O)=O)C3CCCCC3)C=C2CCN1 GRYXVSHAAMIBGD-UHFFFAOYSA-N 0.000 claims 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 1
- 125000005015 aryl alkynyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 1
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0113708A GB0113708D0 (en) | 2001-06-06 | 2001-06-06 | Chemical compounds |
| US31150201P | 2001-08-10 | 2001-08-10 | |
| PCT/GB2002/002517 WO2002098426A1 (en) | 2001-06-06 | 2002-06-05 | Substituted tetrahydroisoquinolines for use in the treatment of inflammatory diseases |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005500276A JP2005500276A (ja) | 2005-01-06 |
| JP2005500276A5 true JP2005500276A5 (https=) | 2005-12-22 |
| JP4583751B2 JP4583751B2 (ja) | 2010-11-17 |
Family
ID=26246159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003501465A Expired - Fee Related JP4583751B2 (ja) | 2001-06-06 | 2002-06-05 | 炎症性疾患の治療に使用するための置換されたテトラヒドロイソキノリン |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7211586B2 (https=) |
| EP (1) | EP1392306B1 (https=) |
| JP (1) | JP4583751B2 (https=) |
| AT (1) | ATE383858T1 (https=) |
| AU (1) | AU2002302783B2 (https=) |
| CA (1) | CA2449402C (https=) |
| DE (1) | DE60224664T2 (https=) |
| DK (1) | DK1392306T3 (https=) |
| ES (1) | ES2296926T3 (https=) |
| IL (1) | IL159203A0 (https=) |
| MX (1) | MXPA03009660A (https=) |
| PT (1) | PT1392306E (https=) |
| WO (1) | WO2002098426A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004287875B2 (en) | 2003-11-05 | 2011-06-02 | Bausch + Lomb Ireland Limited | Modulators of cellular adhesion |
| JP4932495B2 (ja) | 2004-01-23 | 2012-05-16 | アムゲン インコーポレイテッド | 化合物及び使用方法 |
| JP2006056830A (ja) * | 2004-08-20 | 2006-03-02 | Dai Ichi Seiyaku Co Ltd | ２−アリールアミノベンゾオキサゾール誘導体 |
| MX2007006230A (es) | 2004-11-30 | 2007-07-25 | Amgen Inc | Quinolinas y analogos de quinazolinas y su uso como medicamentos para tratar cancer. |
| US7297700B2 (en) * | 2005-03-24 | 2007-11-20 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| DK2444079T3 (en) | 2005-05-17 | 2017-01-30 | Sarcode Bioscience Inc | Compositions and Methods for the Treatment of Eye Diseases |
| WO2007050124A1 (en) * | 2005-05-19 | 2007-05-03 | Xenon Pharmaceuticals Inc. | Fused piperidine derivatives and their uses as therapeutic agents |
| ES2630406T3 (es) * | 2007-10-19 | 2017-08-21 | Sarcode Bioscience Inc. | Composición y procedimientos para el tratamiento de la retinopatía diabética |
| EP2276508A4 (en) * | 2008-04-15 | 2011-12-28 | Sarcode Bioscience Inc | ADMINISTRATION OF LFA-1 ANTAGONISTS TO THE GASTROINTESTINAL SYSTEM |
| US8080562B2 (en) | 2008-04-15 | 2011-12-20 | Sarcode Bioscience Inc. | Crystalline pharmaceutical and methods of preparation and use thereof |
| EP2265124A4 (en) * | 2008-04-15 | 2011-12-28 | Sarcode Bioscience Inc | AEROSOLISED LFA-1 ANTAGONISTS FOR THE USE IN THE LOCAL TREATMENT OF IMMUNE DISEASES |
| WO2009128934A1 (en) * | 2008-04-15 | 2009-10-22 | Sarcode Corporation | Topical lfa-1 antagonists for use in localized treatment of immune related disorders |
| US8324384B2 (en) | 2009-02-12 | 2012-12-04 | Merck Sharp & Dohme Corp. | Glucagon receptor antagonist compounds, compositions containing such compounds and methods of use |
| US8378105B2 (en) | 2009-10-21 | 2013-02-19 | Sarcode Bioscience Inc. | Crystalline pharmaceutical and methods of preparation and use thereof |
| RS54936B1 (sr) * | 2011-10-14 | 2016-11-30 | Ambit Biosciences Corp | Heterociklična jedinjenja i njihova upotreba kao modulatora receptora tirozin kinaza tipa iii |
| AU2012346214B2 (en) * | 2011-11-30 | 2017-09-14 | Bikam Pharmaceuticals, Inc. | Opsin-binding ligands, compositions and methods of use |
| CA2879982C (en) | 2012-07-25 | 2020-09-01 | Sarcode Bioscience Inc. | Lfa-1 inhibitor and polymorph thereof |
| WO2018140876A1 (en) * | 2017-01-30 | 2018-08-02 | Biogen Ma Inc. | Nrf2 activator |
| WO2018165520A1 (en) | 2017-03-10 | 2018-09-13 | Vps-3, Inc. | Metalloenzyme inhibitor compounds |
| AU2020321955A1 (en) | 2019-07-30 | 2022-03-17 | Eikonizo Therapapeutics, Inc. | HDAC6 inhibitors and uses thereof |
| WO2023287241A1 (ko) * | 2021-07-15 | 2023-01-19 | 주식회사 휴사이온 | 신규한 벤즈옥사졸아민 유도체 화합물 및 이를 포함하는 암의 예방 또는 치료용 약학 조성물 |
| IL316201A (en) | 2022-04-08 | 2024-12-01 | Eikonizo Therapeutics Inc | Oxadiazole HDAC6 inhibitors and their uses |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5236934A (en) * | 1992-08-26 | 1993-08-17 | E. I. Du Pont De Nemours And Company | 1,2,3,4-tetrahydroisoquinolines useful in the treatment of CNS disorders |
| KR20010083081A (ko) * | 1998-06-30 | 2001-08-31 | 실버스타인 아써 에이. | 염증성질환, 자가면역질환 및 호흡기질환을 치료하는데유용한 브이엘에이-4-의존성 세포 결합의 비-펩티딜 억제제 |
| WO2000015612A1 (en) * | 1998-08-26 | 2000-03-23 | Aventis Pharma Limited | Aza-bicycles which modulate the inhibition of cell adhesion |
| CA2385882C (en) * | 1999-09-24 | 2009-11-24 | Genentech, Inc. | Tyrosine derivatives |
-
2002
- 2002-06-05 JP JP2003501465A patent/JP4583751B2/ja not_active Expired - Fee Related
- 2002-06-05 EP EP02730462A patent/EP1392306B1/en not_active Expired - Lifetime
- 2002-06-05 AU AU2002302783A patent/AU2002302783B2/en not_active Ceased
- 2002-06-05 WO PCT/GB2002/002517 patent/WO2002098426A1/en not_active Ceased
- 2002-06-05 DE DE60224664T patent/DE60224664T2/de not_active Expired - Lifetime
- 2002-06-05 AT AT02730462T patent/ATE383858T1/de not_active IP Right Cessation
- 2002-06-05 CA CA002449402A patent/CA2449402C/en not_active Expired - Fee Related
- 2002-06-05 DK DK02730462T patent/DK1392306T3/da active
- 2002-06-05 MX MXPA03009660A patent/MXPA03009660A/es unknown
- 2002-06-05 IL IL15920302A patent/IL159203A0/xx unknown
- 2002-06-05 ES ES02730462T patent/ES2296926T3/es not_active Expired - Lifetime
- 2002-06-05 PT PT02730462T patent/PT1392306E/pt unknown
-
2003
- 2003-11-18 US US10/715,662 patent/US7211586B2/en not_active Expired - Fee Related
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