JP2005527521A5 - - Google Patents
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- Publication number
- JP2005527521A5 JP2005527521A5 JP2003575904A JP2003575904A JP2005527521A5 JP 2005527521 A5 JP2005527521 A5 JP 2005527521A5 JP 2003575904 A JP2003575904 A JP 2003575904A JP 2003575904 A JP2003575904 A JP 2003575904A JP 2005527521 A5 JP2005527521 A5 JP 2005527521A5
- Authority
- JP
- Japan
- Prior art keywords
- dioxide
- alkyl
- naphthyridine
- carboxamide
- hydroxy
- 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
- 208000030507 AIDS Diseases 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- -1 (4) triazolyl Chemical group 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000003857 carboxamides Chemical class 0.000 claims 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- SRWFMELLCGDMJK-UHFFFAOYSA-N 5-[ethylsulfonyl(methyl)amino]-n-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-8-hydroxy-1,6-naphthyridine-7-carboxamide Chemical compound OC=1C2=NC=CC=C2C(N(C)S(=O)(=O)CC)=NC=1C(=O)NCC1=CC=C(F)C=C1C(=O)NC SRWFMELLCGDMJK-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- ITTLNCKGYQDJSA-UHFFFAOYSA-N n-[(2-carbamoyl-4-fluorophenyl)methyl]-8-hydroxy-5-[methyl(methylsulfonyl)amino]-1,6-naphthyridine-7-carboxamide Chemical compound OC=1C2=NC=CC=C2C(N(C)S(C)(=O)=O)=NC=1C(=O)NCC1=CC=C(F)C=C1C(N)=O ITTLNCKGYQDJSA-UHFFFAOYSA-N 0.000 claims 2
- VYPQWAVDQALNKV-UHFFFAOYSA-N n-[[4-fluoro-2-(methylcarbamoyl)phenyl]methyl]-8-hydroxy-5-[methyl(methylsulfonyl)amino]-1,6-naphthyridine-7-carboxamide Chemical compound CNC(=O)C1=CC(F)=CC=C1CNC(=O)C1=NC(N(C)S(C)(=O)=O)=C(C=CC=N2)C2=C1O VYPQWAVDQALNKV-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- YKEGCGXXZWOYCF-UHFFFAOYSA-N 1,6-naphthyridine-7-carboxamide Chemical compound C1=CC=C2C=NC(C(=O)N)=CC2=N1 YKEGCGXXZWOYCF-UHFFFAOYSA-N 0.000 claims 1
- 108010002459 HIV Integrase Proteins 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- ZQQYEYLUHHVDMD-UHFFFAOYSA-N n-[[2-(dimethylcarbamoyl)-4-fluorophenyl]methyl]-8-hydroxy-5-[methyl(methylsulfonyl)amino]-1,6-naphthyridine-7-carboxamide Chemical compound CN(C)C(=O)C1=CC(F)=CC=C1CNC(=O)C1=NC(N(C)S(C)(=O)=O)=C(C=CC=N2)C2=C1O ZQQYEYLUHHVDMD-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- ZCXZWWUQZHIJCM-UHFFFAOYSA-N 8-hydroxy-1,6-naphthyridine-7-carboxamide Chemical class C1=CC=NC2=C(O)C(C(=O)N)=NC=C21 ZCXZWWUQZHIJCM-UHFFFAOYSA-N 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 229940099797 HIV integrase inhibitor Drugs 0.000 description 1
- 239000003084 hiv integrase inhibitor Substances 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US36492902P | 2002-03-15 | 2002-03-15 | |
| PCT/US2003/007448 WO2003077850A2 (en) | 2002-03-15 | 2003-03-12 | N-(substituted benzyl)-8-hydroxy-1,6-naphthyridine-7- carboxamides useful as hiv integrase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005527521A JP2005527521A (ja) | 2005-09-15 |
| JP2005527521A5 true JP2005527521A5 (https=) | 2006-04-13 |
| JP4494020B2 JP4494020B2 (ja) | 2010-06-30 |
Family
ID=28041987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003575904A Expired - Fee Related JP4494020B2 (ja) | 2002-03-15 | 2003-03-12 | Ｈｉｖインテグラーゼ阻害剤として有用なｎ−（置換ベンジル）−８−ヒドロキシ−１，６−ナフチリジン−７−カルボキサミド |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7323460B2 (https=) |
| EP (1) | EP1496836B1 (https=) |
| JP (1) | JP4494020B2 (https=) |
| AT (1) | ATE409187T1 (https=) |
| AU (2) | AU2003220170B2 (https=) |
| CA (1) | CA2478310A1 (https=) |
| DE (1) | DE60323743D1 (https=) |
| WO (2) | WO2003077857A2 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE409187T1 (de) * | 2002-03-15 | 2008-10-15 | Merck & Co Inc | N-(substituierte benzyl)-8-hydroxy-1,6- naphthyridin-7- carbonsäureamide als hiv- integrase-hemmer |
| ATE404537T1 (de) | 2002-08-13 | 2008-08-15 | Shionogi & Co | Heterocyclische verbindungen mit hiv-integrase- hemmender wirkung |
| PA8586801A1 (es) | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| WO2004067531A1 (en) | 2003-01-27 | 2004-08-12 | Pfizer Inc. | Hiv-integrase inhibitors, pharmaceutical compositions, and methods for their use |
| WO2004080402A2 (en) * | 2003-03-12 | 2004-09-23 | Merck & Co. Inc. | Potassium salt of an hiv integrase inhibitor |
| CA2537325A1 (en) * | 2003-09-19 | 2005-03-31 | Gilead Sciences, Inc. | Aza-quinolinol phosphonate integrase inhibitor compounds |
| AU2004285449A1 (en) | 2003-10-20 | 2005-05-12 | Merck & Co., Inc. | Hydroxy pyridopyrrolopyrazine dione compounds useful as HIV integrase inhibitors |
| JP4789144B2 (ja) * | 2004-02-04 | 2011-10-12 | 塩野義製薬株式会社 | Ｈｉｖインテグラーゼ阻害活性を有するナフチリジン誘導体 |
| JP4625838B2 (ja) * | 2004-03-09 | 2011-02-02 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｈｉｖインテグラーゼ阻害薬 |
| CA2564356A1 (en) | 2004-04-26 | 2005-11-03 | Pfizer Inc. | Pyrrolopyridine derivatives and their use as hiv-integrase inhibitors |
| DE602005002746T2 (de) | 2004-04-26 | 2008-02-07 | Pfizer Inc. | Inhibitoren des hiv-integrase-enzyms |
| AU2006306355A1 (en) * | 2005-10-27 | 2007-05-03 | Merck & Co., Inc. | HIV integrase inhibitors |
| BRPI0716539A2 (pt) | 2006-09-07 | 2016-11-01 | Emisphere Tech Inc | métodos para sintetização de ácido n-(8-[2-hidroxibenzoil]amino) caprílico e de sal de sódio deste |
| CN106117196A (zh) * | 2016-06-09 | 2016-11-16 | 青岛辰达生物科技有限公司 | 一种制备抗癌药物达沙替尼的方法 |
| CN107722106A (zh) * | 2016-08-11 | 2018-02-23 | 重庆大学 | Hiv抑制剂 |
| CN112409267A (zh) * | 2019-08-22 | 2021-02-26 | 江苏阿尔法药业有限公司 | 一种索菲布韦中间体的制备方法 |
| AR122928A1 (es) * | 2020-07-10 | 2022-10-19 | Goldfinch Bio Inc | 1,6-naftiridinas sustituidas inhibidoras de cdk5 |
Family Cites Families (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5751837B2 (https=) | 1973-04-05 | 1982-11-04 | ||
| US4416884A (en) * | 1978-04-12 | 1983-11-22 | Otsuka Pharmaceutical Co., Ltd. | Piperazinylbenzoheterocyclic compounds |
| FR2632639B1 (fr) * | 1988-06-09 | 1990-10-05 | Sanofi Sa | Derives d'amino-4 carboxy-3 naphtyridines, leur preparation et compositions pharmaceutiques qui les contiennent |
| IL101860A0 (en) * | 1991-05-31 | 1992-12-30 | Ici Plc | Heterocyclic derivatives |
| TW263498B (https=) * | 1993-11-10 | 1995-11-21 | Takeda Pharm Industry Co Ltd | |
| DE69509442T2 (de) * | 1994-06-16 | 1999-09-02 | Lg Chemical Ltd. | Chinolincarbonsäurederivate mit 7-(4-Amino-methyl-3-oxim)-pyrrolidin-Substituenten und Verfahren zu ihrer Herstellung |
| US5776944A (en) * | 1994-06-16 | 1998-07-07 | Lg Chemical Ltd. | 7-(4-aminomethyl-3-methyloxyiminopyrroplidin-1-yl)-1-cyclopropyl-6-flu oro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and the process for the preparation thereof |
| US5681832A (en) | 1995-02-17 | 1997-10-28 | The United States Of America As Represented By The Department Of Health And Human Services | Aroylaniline compounds, pharmaceutical compositions, and methods of using same to inhibit viral activity |
| WO1997004775A1 (en) * | 1995-08-02 | 1997-02-13 | Chiroscience Limited | Quinolones and their therapeutic use |
| US5945431A (en) * | 1996-03-15 | 1999-08-31 | Biochem Therapeutics Incorporated | Cytomegalovirus inhibiting compounds |
| US6310211B1 (en) | 1996-09-10 | 2001-10-30 | Pharmacia & Upjohn Company | 8-hydroxy-7-substituted quinolines as anti-viral agents |
| WO1998013350A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Qinoline derivatives inhibiting the effect of growth factors such as vegf |
| DE69828284T2 (de) * | 1997-06-30 | 2005-12-08 | Nippon Kayaku K.K. | Naphthyridinderivate oder salze davon |
| KR20010023313A (ko) | 1997-08-25 | 2001-03-26 | 해피 페너 ; 해리 에이치. 페너 2세 | Ｇａｂａ 뇌 수용체 리간드로서의 치환된4-옥소-나프티리딘-3-카르복스아미드 |
| GB9720052D0 (en) | 1997-09-19 | 1997-11-19 | Smithkline Beecham Plc | Novel compounds |
| KR20010015639A (ko) * | 1997-09-30 | 2001-02-26 | 스즈키 다다시 | 술포닐 유도체 |
| CN1283995A (zh) * | 1997-12-11 | 2001-02-14 | 生化制药有限公司 | 抗病毒化合物 |
| PL341364A1 (en) | 1997-12-22 | 2001-04-09 | Upjohn Co | 4-hydroxyqinoline-3-carboxamides and hydrazides as antiviral agents |
| JP2002517390A (ja) | 1998-06-03 | 2002-06-18 | メルク エンド カムパニー インコーポレーテッド | Ｈｉｖインテグラーゼ阻害薬 |
| US6306891B1 (en) * | 1998-06-03 | 2001-10-23 | Merck & Co., Inc. | HIV integrase inhibitors |
| US6262055B1 (en) * | 1998-06-03 | 2001-07-17 | Merck & Co., Inc. | HIV integrase inhibitors |
| CA2329134A1 (en) | 1998-06-03 | 1999-12-09 | David L. Clark | Hiv integrase inhibitors |
| US6380249B1 (en) * | 1998-06-03 | 2002-04-30 | Merck & Co., Inc. | HIV integrase inhibitors |
| AU4225499A (en) | 1998-06-03 | 1999-12-20 | Merck & Co., Inc. | Hiv integrase inhibitors |
| SE9802550D0 (sv) | 1998-07-15 | 1998-07-15 | Active Biotech Ab | Quinoline derivatives |
| ID27843A (id) * | 1998-08-11 | 2001-04-26 | Pfizer Prod Inc | Substitusi 1, 8-naftiridin-4(ih)-on sebagai penghambat fosfodiesterase 4 |
| AU5880600A (en) | 1999-06-25 | 2001-01-31 | Merck & Co., Inc. | 1-(aromatic- or heteroaromatic-substituted)-3-(heteroaromatic substituted)-1,3-propanediones and uses thereof |
| US20040039060A1 (en) * | 2000-06-14 | 2004-02-26 | Ryuichi Kiyama | Inhibitor for enzyme having two divalent metal ions as active centers |
| US6730682B2 (en) | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| GB0017676D0 (en) * | 2000-07-19 | 2000-09-06 | Angeletti P Ist Richerche Bio | Inhibitors of viral polymerase |
| WO2002009504A1 (en) * | 2000-08-02 | 2002-02-07 | George Robert A | Squirrel-proof bird feeding apparatus and method |
| ATE345129T1 (de) * | 2000-10-12 | 2006-12-15 | Merck & Co Inc | Aza- und polyaza-naphthalenylcarbonsäureamide als hiv-integrase-hemmer |
| PL360944A1 (en) * | 2000-10-12 | 2004-09-20 | Merck & Co, Inc. | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| WO2002036734A2 (en) * | 2000-10-12 | 2002-05-10 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl ketones useful as hiv integrase inhibitors |
| EP1326611B1 (en) * | 2000-10-12 | 2007-06-13 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl-carboxamides useful as hiv integrase inhibitors |
| JP3616628B2 (ja) * | 2001-03-01 | 2005-02-02 | 塩野義製薬株式会社 | Ｈｉｖインテグラーゼ阻害活性を有する含窒素芳香族複素環化合物 |
| AR036256A1 (es) * | 2001-08-17 | 2004-08-25 | Merck & Co Inc | Sal sodica de un inhibidor de integrasa del vih, procesos para su preparacion, composiciones farmaceuticas que lo contienen y su uso para la manufactura de un medicamento |
| IL161337A0 (en) | 2001-10-26 | 2004-09-27 | Angeletti P Ist Richerche Bio | N-substituted hydroxypyrimidinone carboxamide inhibitors of hiv integrase |
| ATE355064T1 (de) | 2001-10-26 | 2006-03-15 | Angeletti P Ist Richerche Bio | Dihydroxypyrimidin-carbonsäueramid-hemmer der hiv-integrase |
| ATE409187T1 (de) * | 2002-03-15 | 2008-10-15 | Merck & Co Inc | N-(substituierte benzyl)-8-hydroxy-1,6- naphthyridin-7- carbonsäureamide als hiv- integrase-hemmer |
| AU2003220186A1 (en) * | 2002-04-10 | 2003-10-27 | Merck And Co., Inc. | Pharmaceutical compositions containing an hiv integrase inhibitor and a nonionic surfactant |
-
2003
- 2003-03-12 AT AT03716466T patent/ATE409187T1/de not_active IP Right Cessation
- 2003-03-12 AU AU2003220170A patent/AU2003220170B2/en not_active Ceased
- 2003-03-12 EP EP03716466A patent/EP1496836B1/en not_active Expired - Lifetime
- 2003-03-12 DE DE60323743T patent/DE60323743D1/de not_active Expired - Lifetime
- 2003-03-12 AU AU2003218130A patent/AU2003218130A1/en not_active Abandoned
- 2003-03-12 JP JP2003575904A patent/JP4494020B2/ja not_active Expired - Fee Related
- 2003-03-12 CA CA002478310A patent/CA2478310A1/en not_active Abandoned
- 2003-03-12 WO PCT/US2003/007671 patent/WO2003077857A2/en not_active Ceased
- 2003-03-12 WO PCT/US2003/007448 patent/WO2003077850A2/en not_active Ceased
- 2003-03-12 US US10/508,094 patent/US7323460B2/en not_active Expired - Fee Related