JP2007519735A5 - - Google Patents
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- JP2007519735A5 JP2007519735A5 JP2006551441A JP2006551441A JP2007519735A5 JP 2007519735 A5 JP2007519735 A5 JP 2007519735A5 JP 2006551441 A JP2006551441 A JP 2006551441A JP 2006551441 A JP2006551441 A JP 2006551441A JP 2007519735 A5 JP2007519735 A5 JP 2007519735A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- fluorobenzyl
- ring
- dihydroxy
- aryl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 59
- 150000001875 compounds Chemical class 0.000 claims 38
- 125000005842 heteroatom Chemical group 0.000 claims 31
- 229910052799 carbon Inorganic materials 0.000 claims 29
- 125000000623 heterocyclic group Chemical group 0.000 claims 28
- -1 pyridoimidazolyl Chemical group 0.000 claims 25
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 24
- 125000004432 carbon atom Chemical group C* 0.000 claims 21
- 229910052760 oxygen Inorganic materials 0.000 claims 17
- 229910052717 sulfur Inorganic materials 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000004434 sulfur atom Chemical group 0.000 claims 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 7
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 6
- 208000030507 AIDS Diseases 0.000 claims 5
- 208000031886 HIV Infections Diseases 0.000 claims 4
- 208000037357 HIV infectious disease Diseases 0.000 claims 4
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 108010002459 HIV Integrase Proteins 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 2
- 239000002777 nucleoside Substances 0.000 claims 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 2
- ABIUKFCOCNGSHD-UHFFFAOYSA-N 2-benzyl-2-N-[(4-fluorophenyl)methyl]-5-hydroxy-2-N,1-dimethyl-6-oxo-3H-pyridine-2,4-dicarboxamide Chemical compound C1C(C(N)=O)=C(O)C(=O)N(C)C1(CC=1C=CC=CC=1)C(=O)N(C)CC1=CC=C(F)C=C1 ABIUKFCOCNGSHD-UHFFFAOYSA-N 0.000 claims 1
- DJRLNZRPQMUKMU-UHFFFAOYSA-N 2-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6-n-(pyridin-3-ylmethyl)-1h-pyridine-2,6-dicarboxamide Chemical compound OC=1C(O)=CC(C(=O)NCC=2C=NC=CC=2)=NC=1C(=O)NCC1=CC=C(F)C=C1 DJRLNZRPQMUKMU-UHFFFAOYSA-N 0.000 claims 1
- ZKTKFRQUZXSODN-UHFFFAOYSA-N 2-n-benzyl-4-n-[(4-fluorophenyl)methyl]-5-hydroxy-2-n-methyl-6-oxo-1h-pyridine-2,4-dicarboxamide Chemical compound C=1C(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(O)=NC=1C(=O)N(C)CC1=CC=CC=C1 ZKTKFRQUZXSODN-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- HZGWAUGPLADRFT-UHFFFAOYSA-N 6-(3,4-dihydro-1h-isoquinoline-2-carbonyl)-n-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-1h-pyridine-4-carboxamide Chemical compound OC=1C(O)=NC(C(=O)N2CC3=CC=CC=C3CC2)=CC=1C(=O)NCC1=CC=C(F)C=C1 HZGWAUGPLADRFT-UHFFFAOYSA-N 0.000 claims 1
- LCQICUJJENZKEI-UHFFFAOYSA-N 6-N,6-N-diethylpyridine-2,6-dicarboxamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C(N)=O)=N1 LCQICUJJENZKEI-UHFFFAOYSA-N 0.000 claims 1
- XBQLZJFKYZNCBF-UHFFFAOYSA-N 6-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-4-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 XBQLZJFKYZNCBF-UHFFFAOYSA-N 0.000 claims 1
- VIUWHIDOPXAHLZ-UHFFFAOYSA-N 6-[1-(dimethylamino)ethyl]-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-1h-pyridine-2-carboxamide Chemical compound CN(C)C(C)C1=CC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 VIUWHIDOPXAHLZ-UHFFFAOYSA-N 0.000 claims 1
- NTIQYKQZYIXZCT-UHFFFAOYSA-N 6-[1-[acetyl(methyl)amino]ethyl]-n-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-1h-pyridine-4-carboxamide Chemical compound OC1=NC(C(N(C)C(C)=O)C)=CC(C(=O)NCC=2C=CC(F)=CC=2)=C1O NTIQYKQZYIXZCT-UHFFFAOYSA-N 0.000 claims 1
- QCVLAGKLUOKINC-UHFFFAOYSA-N 6-[3-[(dimethylamino)methyl]piperidine-1-carbonyl]-n-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-1h-pyridine-4-carboxamide Chemical compound C1C(CN(C)C)CCCN1C(=O)C1=CC(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(O)=N1 QCVLAGKLUOKINC-UHFFFAOYSA-N 0.000 claims 1
- NAMVDIPAXVEZDY-UHFFFAOYSA-N 6-acetyl-n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-1h-pyridine-2-carboxamide Chemical compound CC(=O)C1=CC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 NAMVDIPAXVEZDY-UHFFFAOYSA-N 0.000 claims 1
- MOXOHHGYVUFJER-UHFFFAOYSA-N C1=CC=C(C=C1)CC2(C=C(C(=C(N2)C(=O)NCC3=CC=C(C=C3)F)O)O)C(=O)N Chemical compound C1=CC=C(C=C1)CC2(C=C(C(=C(N2)C(=O)NCC3=CC=C(C=C3)F)O)O)C(=O)N MOXOHHGYVUFJER-UHFFFAOYSA-N 0.000 claims 1
- AJTJYGHBWBOGPS-UHFFFAOYSA-N C1=CC=C(C=C1)CC2(C=C(C(=C(N2)O)O)C(=O)NCC3=CC=C(C=C3)F)C(=O)N Chemical compound C1=CC=C(C=C1)CC2(C=C(C(=C(N2)O)O)C(=O)NCC3=CC=C(C=C3)F)C(=O)N AJTJYGHBWBOGPS-UHFFFAOYSA-N 0.000 claims 1
- PAGQZTQUJYLIDD-UHFFFAOYSA-N CC=1C(=NC=CC1C(=O)N)C(=O)N Chemical compound CC=1C(=NC=CC1C(=O)N)C(=O)N PAGQZTQUJYLIDD-UHFFFAOYSA-N 0.000 claims 1
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 1
- CLINGMMRAJVCQN-UHFFFAOYSA-N N-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-6-pyridin-2-yl-1H-pyridine-4-carboxamide Chemical compound OC=1C(O)=NC(C=2N=CC=CC=2)=CC=1C(=O)NCC1=CC=C(F)C=C1 CLINGMMRAJVCQN-UHFFFAOYSA-N 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000890 drug combination Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- IYOSVLIBARIRGD-UHFFFAOYSA-N methyl 6-[(4-fluorophenyl)methylcarbamoyl]-5-hydroxy-4-oxo-1h-pyridine-2-carboxylate Chemical compound COC(=O)C1=CC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 IYOSVLIBARIRGD-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- HYZHWWXTKMGSEN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-6-(trifluoromethyl)-1h-pyridine-4-carboxamide Chemical compound OC1=NC(C(F)(F)F)=CC(C(=O)NCC=2C=CC(F)=CC=2)=C1O HYZHWWXTKMGSEN-UHFFFAOYSA-N 0.000 claims 1
- HIYSOLCVNKPYOI-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-6-pyridin-3-yl-1h-pyridine-4-carboxamide Chemical compound OC=1C(O)=NC(C=2C=NC=CC=2)=CC=1C(=O)NCC1=CC=C(F)C=C1 HIYSOLCVNKPYOI-UHFFFAOYSA-N 0.000 claims 1
- DIONQIWUWUGGFH-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-6-pyrimidin-5-yl-1h-pyridine-4-carboxamide Chemical compound OC=1C(O)=NC(C=2C=NC=NC=2)=CC=1C(=O)NCC1=CC=C(F)C=C1 DIONQIWUWUGGFH-UHFFFAOYSA-N 0.000 claims 1
- NDBMYVJFTZLCQE-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-2-oxo-6-thiophen-2-yl-1h-pyridine-4-carboxamide Chemical compound OC=1C(O)=NC(C=2SC=CC=2)=CC=1C(=O)NCC1=CC=C(F)C=C1 NDBMYVJFTZLCQE-UHFFFAOYSA-N 0.000 claims 1
- VRALUQLTCRXORN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-4-oxo-6-(pyrrolidine-1-carbonyl)-1h-pyridine-2-carboxamide Chemical compound OC=1C(O)=CC(C(=O)N2CCCC2)=NC=1C(=O)NCC1=CC=C(F)C=C1 VRALUQLTCRXORN-UHFFFAOYSA-N 0.000 claims 1
- KMZCOCJUQVAPNV-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-6-(1-morpholin-4-ylethyl)-2-oxo-1h-pyridine-4-carboxamide Chemical compound C=1C(C(=O)NCC=2C=CC(F)=CC=2)=C(O)C(O)=NC=1C(C)N1CCOCC1 KMZCOCJUQVAPNV-UHFFFAOYSA-N 0.000 claims 1
- AYTZFZALVFVVKS-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-6-(5-methyl-1,3,4-oxadiazol-2-yl)-4-oxo-1h-pyridine-2-carboxamide Chemical compound O1C(C)=NN=C1C1=CC(O)=C(O)C(C(=O)NCC=2C=CC(F)=CC=2)=N1 AYTZFZALVFVVKS-UHFFFAOYSA-N 0.000 claims 1
- IFFUMEOOLKGNCH-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-3-hydroxy-6-(morpholine-4-carbonyl)-4-oxo-1h-pyridine-2-carboxamide Chemical compound OC=1C(O)=CC(C(=O)N2CCOCC2)=NC=1C(=O)NCC1=CC=C(F)C=C1 IFFUMEOOLKGNCH-UHFFFAOYSA-N 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 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
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Cc1ccccc1 Chemical compound Cc1ccccc1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US54053804P | 2004-01-30 | 2004-01-30 | |
| PCT/US2005/002472 WO2005074513A2 (en) | 2004-01-30 | 2005-01-26 | N-benzyl-3,4-dihyroxypyridine-2-carboxamide and n-benzyl-2,3-dihydroxypyridine-4-carboxamide compounds useful as hiv integrase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007519735A JP2007519735A (ja) | 2007-07-19 |
| JP2007519735A5 true JP2007519735A5 (US07981874-20110719-C00313.png) | 2008-03-13 |
Family
ID=34837394
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006551441A Withdrawn JP2007519735A (ja) | 2004-01-30 | 2005-01-26 | Ｈｉｖインテグラーゼ阻害剤として有用であるｎ−ベンジル−３，４−ジヒドロキシピリジン−２−カルボキサミド及びｎ−ベンジル−２，３−ジヒドロキシピリジン−４−カルボキサミド化合物 |
Country Status (7)
Families Citing this family (51)
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| DK2266958T1 (da) | 2001-08-10 | 2016-04-04 | Shionogi & Co | Antiviralt middel |
| AU2006306355A1 (en) * | 2005-10-27 | 2007-05-03 | Merck & Co., Inc. | HIV integrase inhibitors |
| CN101611007A (zh) | 2006-12-20 | 2009-12-23 | 先灵公司 | 新颖的jnk抑制剂 |
| EP2496236B1 (en) | 2009-11-06 | 2013-05-01 | Aerpio Therapeutics Inc. | Prolyl hydroxylase inhibitors |
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| WO2013049104A1 (en) * | 2011-09-30 | 2013-04-04 | Bristol-Myers Squibb Company | Pyridinedione carboxamide inhibitors of endothelial lipase |
| US8933235B2 (en) | 2011-09-30 | 2015-01-13 | Bristol-Myers Squibb Company | Pyridinedione carboxamide inhibitors of endothelial lipase |
| US9206128B2 (en) * | 2011-11-18 | 2015-12-08 | Constellation Pharmaceuticals, Inc. | Modulators of methyl modifying enzymes, compositions and uses thereof |
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| CN105073728A (zh) | 2013-03-15 | 2015-11-18 | 全球血液疗法股份有限公司 | 化合物及其用于调节血红蛋白的用途 |
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| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| CA2902711C (en) | 2013-03-15 | 2021-07-06 | Global Blood Therapeutics, Inc. | Substituted pyridinyl-6-methoxy-2-hydroxybenzaldehyde derivatives and pharmaceutical compositions thereof useful for the modulation of hemoglobin |
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| EP2986291B1 (en) | 2013-04-16 | 2020-05-27 | Merck Sharp & Dohme Corp. | 4-pyridone derivative compounds and uses thereof as hiv integrase inhibitors |
| NO2865735T3 (US07981874-20110719-C00313.png) | 2013-07-12 | 2018-07-21 | ||
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| TWI677489B (zh) | 2014-06-20 | 2019-11-21 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| NO2717902T3 (US07981874-20110719-C00313.png) | 2014-06-20 | 2018-06-23 | ||
| KR102286305B1 (ko) * | 2014-07-16 | 2021-08-09 | 라이프에스씨아이 파마슈티컬스, 인크. | 치료적 억제 화합물 |
| JP2017523197A (ja) * | 2014-07-30 | 2017-08-17 | エービーエーシー セラピューティクス，エス．エル． | ２−ピリドン部分を含む選択的抗菌剤としてのアリールヒドラジド |
| TWI695003B (zh) | 2014-12-23 | 2020-06-01 | 美商基利科學股份有限公司 | 多環胺甲醯基吡啶酮化合物及其醫藥用途 |
| MA41614A (fr) | 2015-02-25 | 2018-01-02 | Alios Biopharma Inc | Composés antiviraux |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
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| US6262055B1 (en) * | 1998-06-03 | 2001-07-17 | Merck & Co., Inc. | HIV integrase inhibitors |
| US6306891B1 (en) * | 1998-06-03 | 2001-10-23 | Merck & Co., Inc. | HIV integrase inhibitors |
| US6380249B1 (en) * | 1998-06-03 | 2002-04-30 | Merck & Co., Inc. | HIV integrase inhibitors |
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2005
- 2005-01-26 AU AU2005211349A patent/AU2005211349A1/en not_active Abandoned
- 2005-01-26 US US10/587,330 patent/US20070155744A1/en not_active Abandoned
- 2005-01-26 EP EP05726383A patent/EP1713773A4/en not_active Withdrawn
- 2005-01-26 CN CNA2005800033860A patent/CN101014571A/zh active Pending
- 2005-01-26 JP JP2006551441A patent/JP2007519735A/ja not_active Withdrawn
- 2005-01-26 WO PCT/US2005/002472 patent/WO2005074513A2/en active Application Filing
- 2005-01-26 CA CA002554120A patent/CA2554120A1/en not_active Abandoned
