JP2009528296A5 - - Google Patents
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- Publication number
- JP2009528296A5 JP2009528296A5 JP2008556582A JP2008556582A JP2009528296A5 JP 2009528296 A5 JP2009528296 A5 JP 2009528296A5 JP 2008556582 A JP2008556582 A JP 2008556582A JP 2008556582 A JP2008556582 A JP 2008556582A JP 2009528296 A5 JP2009528296 A5 JP 2009528296A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- alkyl
- ylamino
- pyrimidin
- 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
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- 150000001875 compounds Chemical class 0.000 claims description 41
- -1 propargyl compound Chemical class 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 150000003935 benzaldehydes Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 2
- 238000006722 reduction reaction Methods 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- JJOWVQRSSFANTK-QHCPKHFHSA-N (2s)-2-[[2-(diethylamino)-5-[ethyl(2-methylpropylsulfonyl)amino]pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(CC)S(=O)(=O)CC(C)C)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 JJOWVQRSSFANTK-QHCPKHFHSA-N 0.000 claims 1
- LLYUGVGQHYKTPB-NRFANRHFSA-N (2s)-2-[[2-(diethylamino)-5-[ethyl(3,3,3-trifluoropropylsulfonyl)amino]pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(CC)S(=O)(=O)CCC(F)(F)F)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 LLYUGVGQHYKTPB-NRFANRHFSA-N 0.000 claims 1
- WQRWVWWUVJMCFW-FQEVSTJZSA-N (2s)-2-[[2-(diethylamino)-5-[ethyl(methylsulfonyl)amino]pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(CC)S(C)(=O)=O)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 WQRWVWWUVJMCFW-FQEVSTJZSA-N 0.000 claims 1
- GWHSRLXGMCCAIN-QFIPXVFZSA-N (2s)-2-[[2-(diethylamino)-5-[ethyl(propylsulfonyl)amino]pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCCS(=O)(=O)N(CC)C1=CN=C(N(CC)CC)N=C1N[C@H](C(O)=O)CC(C=C1)=CC=C1OC(=O)N1CCCC1 GWHSRLXGMCCAIN-QFIPXVFZSA-N 0.000 claims 1
- DFGIRJIXSZXHRL-IBGZPJMESA-N (2s)-2-[[2-(diethylamino)-5-[methyl(methylsulfonyl)amino]pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(C)S(C)(=O)=O)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 DFGIRJIXSZXHRL-IBGZPJMESA-N 0.000 claims 1
- GDLQGBLMGXDNRQ-NRFANRHFSA-N (2s)-2-[[2-(diethylamino)-5-[methylsulfonyl(prop-2-ynyl)amino]pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(CC#C)S(C)(=O)=O)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 GDLQGBLMGXDNRQ-NRFANRHFSA-N 0.000 claims 1
- SDRNIMLNYYTUKR-NRFANRHFSA-N (2s)-2-[[2-(diethylamino)-5-[methylsulfonyl(propan-2-yl)amino]pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(C(C)C)S(C)(=O)=O)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 SDRNIMLNYYTUKR-NRFANRHFSA-N 0.000 claims 1
- UIUBHENCCNLCKN-QFIPXVFZSA-N (2s)-2-[[5-[3-chloropropylsulfonyl(ethyl)amino]-2-(diethylamino)pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(CC)S(=O)(=O)CCCCl)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 UIUBHENCCNLCKN-QFIPXVFZSA-N 0.000 claims 1
- MJWZBNGONSQHGU-NRFANRHFSA-N (2s)-2-[[5-[3-chloropropylsulfonyl(methyl)amino]-2-(diethylamino)pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCN(CC)C1=NC=C(N(C)S(=O)(=O)CCCCl)C(N[C@@H](CC=2C=CC(OC(=O)N3CCCC3)=CC=2)C(O)=O)=N1 MJWZBNGONSQHGU-NRFANRHFSA-N 0.000 claims 1
- SWLRXLYNAHKZOI-QHCPKHFHSA-N (2s)-2-[[5-[butylsulfonyl(ethyl)amino]-2-(diethylamino)pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound CCCCS(=O)(=O)N(CC)C1=CN=C(N(CC)CC)N=C1N[C@H](C(O)=O)CC(C=C1)=CC=C1OC(=O)N1CCCC1 SWLRXLYNAHKZOI-QHCPKHFHSA-N 0.000 claims 1
- UJURHSUDCZMQEN-QHCPKHFHSA-N (2s)-2-[[5-[cyclopentyl(methylsulfonyl)amino]-2-(diethylamino)pyrimidin-4-yl]amino]-3-[4-(pyrrolidine-1-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC=1C=CC(OC(=O)N2CCCC2)=CC=1)C(O)=O)C1=NC(N(CC)CC)=NC=C1N(S(C)(=O)=O)C1CCCC1 UJURHSUDCZMQEN-QHCPKHFHSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 230000006472 autoimmune response Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 102000006495 integrins Human genes 0.000 claims 1
- 108010044426 integrins Proteins 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 0 CCN(CC)C(C)N=CC(N(*)S(*)(=O)=O)=C(N)N[C@@](CC(C=CC=C)=C*(C)C(N1CCCC1)=O)C(O)=O Chemical compound CCN(CC)C(C)N=CC(N(*)S(*)(=O)=O)=C(N)N[C@@](CC(C=CC=C)=C*(C)C(N1CCCC1)=O)C(O)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77759506P | 2006-02-27 | 2006-02-27 | |
| US60/777,595 | 2006-02-27 | ||
| PCT/US2007/062824 WO2007101165A1 (en) | 2006-02-27 | 2007-02-26 | Pyrimidinyl sulfonamide compounds which inhibit leukocyte adhesion mediated by vla-4 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009528296A JP2009528296A (ja) | 2009-08-06 |
| JP2009528296A5 true JP2009528296A5 (https=) | 2011-04-07 |
| JP5135235B2 JP5135235B2 (ja) | 2013-02-06 |
Family
ID=38215011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008556582A Expired - Fee Related JP5135235B2 (ja) | 2006-02-27 | 2007-02-26 | Ｖａｌ−４によって媒介される白血球の接着を阻害するピリミジニルスルホンアミド化合物 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US7579466B2 (https=) |
| EP (1) | EP1996559A1 (https=) |
| JP (1) | JP5135235B2 (https=) |
| KR (1) | KR20080100271A (https=) |
| CN (1) | CN101389611B (https=) |
| AR (1) | AR059671A1 (https=) |
| AU (1) | AU2007220068B2 (https=) |
| BR (1) | BRPI0708331A2 (https=) |
| CA (1) | CA2643838A1 (https=) |
| EA (1) | EA017110B1 (https=) |
| EC (1) | ECSP088701A (https=) |
| IL (1) | IL193425A (https=) |
| MA (1) | MA30318B1 (https=) |
| MX (1) | MX2008010988A (https=) |
| MY (1) | MY151045A (https=) |
| NO (1) | NO20083743L (https=) |
| NZ (1) | NZ570679A (https=) |
| TW (1) | TWI389904B (https=) |
| WO (1) | WO2007101165A1 (https=) |
| ZA (1) | ZA200807188B (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL350050A1 (en) * | 1999-01-22 | 2002-10-21 | Elan Pharm Inc | Acyl derivatives which treat vla-4 related disorders |
| CN1961002B (zh) * | 2004-05-27 | 2011-05-18 | 克鲁塞尔荷兰公司 | 能中和狂犬病病毒的结合分子及其应用 |
| CA2624524C (en) * | 2005-09-29 | 2014-07-08 | Elan Pharmaceuticals, Inc. | Carbamate compounds which inhibit leukocyte adhesion mediated by vla-4 |
| ATE493405T1 (de) * | 2005-09-29 | 2011-01-15 | Elan Pharm Inc | Pyrimidinylamidverbindungen, die die durch vla-4 vermittelte leukozytenadhäsion inhibieren |
| WO2007101165A1 (en) * | 2006-02-27 | 2007-09-07 | Elan Pharmaceuticals, Inc. | Pyrimidinyl sulfonamide compounds which inhibit leukocyte adhesion mediated by vla-4 |
| ES2752137T3 (es) | 2006-02-28 | 2020-04-03 | Biogen Ma Inc | Métodos para tratar enfermedades inflamatorias y autoinmunes con natalizumab |
| US8410115B2 (en) * | 2006-02-28 | 2013-04-02 | Elan Pharmaceuticals, Inc. | Methods of treating inflammatory and autoimmune diseases with alpha-4 inhibitory compounds |
| WO2007103112A2 (en) | 2006-03-03 | 2007-09-13 | Elan Pharmaceuticals, Inc. | Methods of treating inflammatory and autoimmune diseases with natalizumab |
| JP2011506322A (ja) * | 2007-12-07 | 2011-03-03 | エラン ファーマシューティカルズ，インコーポレイテッド | 液性腫瘍を治療するための方法および組成物 |
| AU2010241742A1 (en) * | 2009-04-27 | 2011-11-17 | Elan Pharmaceuticals, Inc. | Pyridinone antagonists of alpha-4 integrins |
| WO2011020874A1 (en) | 2009-08-20 | 2011-02-24 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Vla-4 as a biomarker for prognosis and target for therapy in duchenne muscular dystrophy |
| US11287423B2 (en) | 2010-01-11 | 2022-03-29 | Biogen Ma Inc. | Assay for JC virus antibodies |
| RS56977B1 (sr) | 2010-01-11 | 2018-05-31 | Biogen Ma Inc | Test za antitela protiv jc virusa |
| PL3575792T3 (pl) | 2011-05-31 | 2023-03-27 | Biogen Ma Inc. | Metoda oceny ryzyka postępującej wieloogniskowej leukoencefalopatii (pml) |
| EP3004334A4 (en) | 2013-05-28 | 2016-12-21 | Biogen Ma Inc | METHOD FOR ASSESSING A PML RISK |
| US10610104B2 (en) | 2016-12-07 | 2020-04-07 | Progenity, Inc. | Gastrointestinal tract detection methods, devices and systems |
| BR112019012071A2 (pt) | 2016-12-14 | 2019-11-12 | Progenity Inc | tratamento de uma doença do trato gastrointestinal com um inibidor de integrina |
| US20230033021A1 (en) | 2018-06-20 | 2023-02-02 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with an integrin inhibitor |
| EP4541422A3 (en) | 2018-10-30 | 2025-06-25 | Gilead Sciences, Inc. | Quinoline derivatives as alpha4beta7 integrin inhibitors |
| AU2019373242B2 (en) | 2018-10-30 | 2023-07-13 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| KR102659859B1 (ko) | 2018-10-30 | 2024-04-25 | 길리애드 사이언시즈, 인코포레이티드 | 알파4β7 인테그린의 억제를 위한 화합물 |
| CN112969700B (zh) | 2018-10-30 | 2024-08-20 | 吉利德科学公司 | 作为α4β7整合素抑制剂的咪唑并吡啶衍生物 |
| US20220249814A1 (en) | 2018-11-19 | 2022-08-11 | Progenity, Inc. | Methods and devices for treating a disease with biotherapeutics |
| KR102908219B1 (ko) | 2019-08-14 | 2026-01-08 | 길리애드 사이언시즈, 인코포레이티드 | 알파 4 베타 7 인테그린의 저해용 화합물 |
| CN121197633A (zh) | 2019-12-13 | 2025-12-26 | 比特比德科有限责任公司 | 用于将治疗剂递送至胃肠道的可摄取装置 |
| US20240301512A1 (en) | 2021-01-29 | 2024-09-12 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of assessing the risk of developing progressive multifocal leukoencephalopathy in patients treated with vla-4 antagonists |
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-
2007
- 2007-02-26 WO PCT/US2007/062824 patent/WO2007101165A1/en not_active Ceased
- 2007-02-26 BR BRPI0708331-9A patent/BRPI0708331A2/pt not_active IP Right Cessation
- 2007-02-26 EA EA200801906A patent/EA017110B1/ru not_active IP Right Cessation
- 2007-02-26 KR KR1020087023333A patent/KR20080100271A/ko not_active Ceased
- 2007-02-26 CA CA002643838A patent/CA2643838A1/en not_active Abandoned
- 2007-02-26 JP JP2008556582A patent/JP5135235B2/ja not_active Expired - Fee Related
- 2007-02-26 EP EP07757498A patent/EP1996559A1/en not_active Withdrawn
- 2007-02-26 AU AU2007220068A patent/AU2007220068B2/en not_active Ceased
- 2007-02-26 TW TW096106544A patent/TWI389904B/zh not_active IP Right Cessation
- 2007-02-26 MY MYPI20083293 patent/MY151045A/en unknown
- 2007-02-26 NZ NZ570679A patent/NZ570679A/en not_active IP Right Cessation
- 2007-02-26 CN CN2007800065837A patent/CN101389611B/zh not_active Expired - Fee Related
- 2007-02-26 US US11/679,042 patent/US7579466B2/en not_active Expired - Fee Related
- 2007-02-26 MX MX2008010988A patent/MX2008010988A/es active IP Right Grant
- 2007-02-27 AR ARP070100812A patent/AR059671A1/es not_active Application Discontinuation
-
2008
- 2008-08-13 IL IL193425A patent/IL193425A/en not_active IP Right Cessation
- 2008-08-22 ZA ZA2008/07188A patent/ZA200807188B/en unknown
- 2008-08-27 EC EC2008008701A patent/ECSP088701A/es unknown
- 2008-08-29 NO NO20083743A patent/NO20083743L/no not_active Application Discontinuation
- 2008-09-11 MA MA31231A patent/MA30318B1/fr unknown
-
2009
- 2009-07-17 US US12/505,383 patent/US7820687B2/en not_active Expired - Fee Related
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