RU2010153656A - Ингибиторы интегразы вич из пиридоксина - Google Patents
Ингибиторы интегразы вич из пиридоксина Download PDFInfo
- Publication number
- RU2010153656A RU2010153656A RU2010153656/04A RU2010153656A RU2010153656A RU 2010153656 A RU2010153656 A RU 2010153656A RU 2010153656/04 A RU2010153656/04 A RU 2010153656/04A RU 2010153656 A RU2010153656 A RU 2010153656A RU 2010153656 A RU2010153656 A RU 2010153656A
- Authority
- RU
- Russia
- Prior art keywords
- hydroxy
- methyl
- hydroxymethyl
- hydroxymethylpyridin
- hydroxyamide
- Prior art date
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- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 title 2
- 229940099797 HIV integrase inhibitor Drugs 0.000 title 1
- 239000003084 hiv integrase inhibitor Substances 0.000 title 1
- 235000008160 pyridoxine Nutrition 0.000 title 1
- 239000011677 pyridoxine Substances 0.000 title 1
- 229940011671 vitamin b6 Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 17
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 13
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims abstract 11
- 125000005843 halogen group Chemical group 0.000 claims abstract 7
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- -1 cyclic acetal Chemical class 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 11
- 241000124008 Mammalia Species 0.000 claims 8
- 208000030507 AIDS Diseases 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 230000002401 inhibitory effect Effects 0.000 claims 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 230000010076 replication Effects 0.000 claims 4
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 3
- 125000000984 3-chloro-4-fluorobenzyl group Chemical group [H]C1=C(F)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 3
- 208000031886 HIV Infections Diseases 0.000 claims 3
- 208000037357 HIV infectious disease Diseases 0.000 claims 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 3
- CTNFPGBWTDBYEL-UHFFFAOYSA-N 2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-5,8-dicarboxylic acid Chemical compound C1=NC(C(O)=O)=C2OC(C)(C)OCC2=C1C(O)=O CTNFPGBWTDBYEL-UHFFFAOYSA-N 0.000 claims 2
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims 2
- JKEJZMBNSCISGJ-UHFFFAOYSA-N 3-hydroxy-4-(hydroxymethyl)pyridine-2,5-dicarboxylic acid Chemical compound OCC1=C(O)C(C(O)=O)=NC=C1C(O)=O JKEJZMBNSCISGJ-UHFFFAOYSA-N 0.000 claims 2
- JQIKOEPLEWEKEB-UHFFFAOYSA-N 5-[(4-fluorophenyl)carbamoylamino]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1NC(=O)NC1=CC=C(F)C=C1 JQIKOEPLEWEKEB-UHFFFAOYSA-N 0.000 claims 2
- ZVWFTPUOKIBHQI-UHFFFAOYSA-N 5-[(4-fluorophenyl)methoxymethyl]-3-hydroxy-4-(hydroxymethyl)-n-methoxypyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NOC)=NC=C1COCC1=CC=C(F)C=C1 ZVWFTPUOKIBHQI-UHFFFAOYSA-N 0.000 claims 2
- ZSCCDMBVYRIVNB-UHFFFAOYSA-N 5-[[(3,5-difluorophenyl)methylamino]methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1CNCC1=CC(F)=CC(F)=C1 ZSCCDMBVYRIVNB-UHFFFAOYSA-N 0.000 claims 2
- UKDLDONJZMSTEV-UHFFFAOYSA-N 5-[[2-(4-fluorophenyl)ethyl-(2-phenylmethoxyethyl)amino]methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(CO)=C1CN(CCC=1C=CC(F)=CC=1)CCOCC1=CC=CC=C1 UKDLDONJZMSTEV-UHFFFAOYSA-N 0.000 claims 2
- IEXOFQPWSZJDRB-UHFFFAOYSA-N 6-(cyclohexylmethylcarbamoyl)-5-hydroxy-4-(hydroxymethyl)pyridine-3-carboxylic acid Chemical compound C1CCCC(C1)CNC(=O)C1=NC=C(C(=C1O)CO)C(=O)O IEXOFQPWSZJDRB-UHFFFAOYSA-N 0.000 claims 2
- LXQULRSWAKFEQK-UHFFFAOYSA-N COC1=CC=C(CNC(=O)C=2C=CC(=NC=2)C(=O)N)C=C1 Chemical compound COC1=CC=C(CNC(=O)C=2C=CC(=NC=2)C(=O)N)C=C1 LXQULRSWAKFEQK-UHFFFAOYSA-N 0.000 claims 2
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical compound Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- CIAXOXXVFFMAPW-UHFFFAOYSA-N methyl 5-[(3-chloro-4-fluorophenoxy)methyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylate Chemical compound C1=2COC(C)(C)OC=2C(C(=O)OC)=NC=C1COC1=CC=C(F)C(Cl)=C1 CIAXOXXVFFMAPW-UHFFFAOYSA-N 0.000 claims 2
- RNWFZPIKVZUZNV-UHFFFAOYSA-N methyl 5-[(4-fluorophenoxy)methyl]-3-hydroxy-4-(hydroxymethyl)pyridine-2-carboxylate Chemical compound OCC1=C(O)C(C(=O)OC)=NC=C1COC1=CC=C(F)C=C1 RNWFZPIKVZUZNV-UHFFFAOYSA-N 0.000 claims 2
- OKJNSJDZIWMLFB-UHFFFAOYSA-N n,3-dihydroxy-4-(hydroxymethyl)-5-(phenylmethoxymethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(CO)=C1COCC1=CC=CC=C1 OKJNSJDZIWMLFB-UHFFFAOYSA-N 0.000 claims 2
- NTLZFMFCOJRHET-UHFFFAOYSA-N n,3-dihydroxy-4-(hydroxymethyl)-5-[(4-methoxyphenyl)methoxymethyl]pyridine-2-carboxamide Chemical compound C1=CC(OC)=CC=C1COCC1=CN=C(C(=O)NO)C(O)=C1CO NTLZFMFCOJRHET-UHFFFAOYSA-N 0.000 claims 2
- XHLCFPQRJWMQRV-UHFFFAOYSA-N n-hydroxy-5-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxamide Chemical compound C1=CC(OC)=CC=C1COCC1=CN=C(C(=O)NO)C2=C1COC(C)(C)O2 XHLCFPQRJWMQRV-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- DVOHZSVOEPGUCR-UHFFFAOYSA-N 2-(aminomethyl)-5-fluoro-n-methylbenzamide Chemical compound CNC(=O)C1=CC(F)=CC=C1CN DVOHZSVOEPGUCR-UHFFFAOYSA-N 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- PVSYQIXIJHOLTC-UHFFFAOYSA-N 3-oxo-n,7-bis(phenylmethoxy)-1h-furo[3,4-c]pyridine-6-carboxamide Chemical compound N=1C=C2C(=O)OCC2=C(OCC=2C=CC=CC=2)C=1C(=O)NOCC1=CC=CC=C1 PVSYQIXIJHOLTC-UHFFFAOYSA-N 0.000 claims 1
- FPUFEHAERIWFGW-UHFFFAOYSA-N 5-(benzenesulfonylmethyl)-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(CO)=C1CS(=O)(=O)C1=CC=CC=C1 FPUFEHAERIWFGW-UHFFFAOYSA-N 0.000 claims 1
- NNKIIHBPBYPYCW-UHFFFAOYSA-N 5-[(1,3-benzodioxol-5-ylmethylamino)methyl]-4-(hydroxymethyl)-n,3-bis(phenylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=CC=CC=1COC=1C(CO)=C(CNCC=2C=C3OCOC3=CC=2)C=NC=1C(=O)NOCC1=CC=CC=C1 NNKIIHBPBYPYCW-UHFFFAOYSA-N 0.000 claims 1
- IFMUKTJCKCYWED-UHFFFAOYSA-N 5-[(1,3-benzodioxol-5-ylmethylamino)methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(CO)=C1CNCC1=CC=C(OCO2)C2=C1 IFMUKTJCKCYWED-UHFFFAOYSA-N 0.000 claims 1
- GIDJZLATDOQHJV-UHFFFAOYSA-N 5-[(2,4-difluorophenyl)methoxymethyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1COCC1=CC=C(F)C=C1F GIDJZLATDOQHJV-UHFFFAOYSA-N 0.000 claims 1
- LHSPHCQJJRQLBG-UHFFFAOYSA-N 5-[(2,4-difluorophenyl)methoxymethyl]-n,3-dihydroxy-4-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(C)=C1COCC1=CC=C(F)C=C1F LHSPHCQJJRQLBG-UHFFFAOYSA-N 0.000 claims 1
- YQQZZELJPWZZGF-UHFFFAOYSA-N 5-[(3,4-difluorophenyl)methoxymethyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1COCC1=CC=C(F)C(F)=C1 YQQZZELJPWZZGF-UHFFFAOYSA-N 0.000 claims 1
- NMWOCFQCEBZNNZ-UHFFFAOYSA-N 5-[(3,4-difluorophenyl)methoxymethyl]-n,3-dihydroxy-4-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(C)=C1COCC1=CC=C(F)C(F)=C1 NMWOCFQCEBZNNZ-UHFFFAOYSA-N 0.000 claims 1
- FEJVUNZIBZSMGY-UHFFFAOYSA-N 5-[(3-chloro-4-fluorophenoxy)methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1COC1=CC=C(F)C(Cl)=C1 FEJVUNZIBZSMGY-UHFFFAOYSA-N 0.000 claims 1
- GDNUYSNPENMCFT-UHFFFAOYSA-N 5-[(3-chloro-4-fluorophenoxy)methyl]-n,3-dihydroxy-4-methylpyridine-2-carboxamide Chemical compound CC1=C(O)C(C(=O)NO)=NC=C1COC1=CC=C(F)C(Cl)=C1 GDNUYSNPENMCFT-UHFFFAOYSA-N 0.000 claims 1
- WPQWKTUJUVNCSU-UHFFFAOYSA-N 5-[(3-chloro-4-fluorophenyl)methoxymethyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1COCC1=CC=C(F)C(Cl)=C1 WPQWKTUJUVNCSU-UHFFFAOYSA-N 0.000 claims 1
- HGTZGAMRDSGHMI-UHFFFAOYSA-N 5-[(4-fluoroanilino)methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1CNC1=CC=C(F)C=C1 HGTZGAMRDSGHMI-UHFFFAOYSA-N 0.000 claims 1
- GCKFPURLKGQKOY-UHFFFAOYSA-N 5-[(4-fluorobenzoyl)amino]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1NC(=O)C1=CC=C(F)C=C1 GCKFPURLKGQKOY-UHFFFAOYSA-N 0.000 claims 1
- QUNIRSQMCBAOSZ-UHFFFAOYSA-N 5-[(4-fluorophenoxy)methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1COC1=CC=C(F)C=C1 QUNIRSQMCBAOSZ-UHFFFAOYSA-N 0.000 claims 1
- PCWUCFJREVXPDR-UHFFFAOYSA-N 5-[(4-fluorophenoxy)methyl]-n,3-dihydroxy-4-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(C)=C1COC1=CC=C(F)C=C1 PCWUCFJREVXPDR-UHFFFAOYSA-N 0.000 claims 1
- AUWUXJLJRXNOOP-UHFFFAOYSA-N 5-[(4-fluorophenyl)methoxymethyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1COCC1=CC=C(F)C=C1 AUWUXJLJRXNOOP-UHFFFAOYSA-N 0.000 claims 1
- HIRRETCAGVJAOY-UHFFFAOYSA-N 5-[(4-fluorophenyl)methoxymethyl]-n,3-dihydroxy-4-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(C)=C1COCC1=CC=C(F)C=C1 HIRRETCAGVJAOY-UHFFFAOYSA-N 0.000 claims 1
- KLUWZKUNSNZLQN-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-2-N,3-dihydroxy-4-(methoxymethyl)-5-N-methyl-4H-pyridine-2,5-dicarboxamide Chemical compound FC1=CC=C(CC2(C(C(=C(N=C2)C(=O)NO)O)COC)C(=O)NC)C=C1 KLUWZKUNSNZLQN-UHFFFAOYSA-N 0.000 claims 1
- FJLYYNOZVRLFSJ-UHFFFAOYSA-N 5-[(4-fluorophenyl)methylsulfonylmethyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1CS(=O)(=O)CC1=CC=C(F)C=C1 FJLYYNOZVRLFSJ-UHFFFAOYSA-N 0.000 claims 1
- GBFDKHXFIGIKJI-UHFFFAOYSA-N 5-[(4-fluorophenyl)methylsulfonylmethyl]-n-hydroxy-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxamide Chemical compound C1=NC(C(=O)NO)=C2OC(C)(C)OCC2=C1CS(=O)(=O)CC1=CC=C(F)C=C1 GBFDKHXFIGIKJI-UHFFFAOYSA-N 0.000 claims 1
- JFANIGWEWQWIRC-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methoxymethyl]-2,2,8-trimethyl-4h-[1,3]dioxino[4,5-c]pyridine Chemical compound C1=CC(OC)=CC=C1COCC1=CN=C(C)C2=C1COC(C)(C)O2 JFANIGWEWQWIRC-UHFFFAOYSA-N 0.000 claims 1
- JUOLVRNHNJGDDT-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methoxymethyl]-2,2,8-trimethyl-7-oxido-4h-[1,3]dioxino[4,5-c]pyridin-7-ium Chemical compound C1=CC(OC)=CC=C1COCC1=C[N+]([O-])=C(C)C2=C1COC(C)(C)O2 JUOLVRNHNJGDDT-UHFFFAOYSA-N 0.000 claims 1
- QZFKTDQEKAREPX-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carbaldehyde Chemical compound C1=CC(OC)=CC=C1COCC1=CN=C(C=O)C2=C1COC(C)(C)O2 QZFKTDQEKAREPX-UHFFFAOYSA-N 0.000 claims 1
- HSBBUPZHSFWEMX-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylic acid Chemical compound C1=CC(OC)=CC=C1COCC1=CN=C(C(O)=O)C2=C1COC(C)(C)O2 HSBBUPZHSFWEMX-UHFFFAOYSA-N 0.000 claims 1
- RPFXSEFNSNFRIM-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-n-phenylmethoxy-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxamide Chemical compound C1=CC(OC)=CC=C1COCC(C=1COC(C)(C)OC=11)=CN=C1C(=O)NOCC1=CC=CC=C1 RPFXSEFNSNFRIM-UHFFFAOYSA-N 0.000 claims 1
- OGIQXAWRYHWHLV-UHFFFAOYSA-N 5-[(n-benzyl-4-fluoroanilino)methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(CO)=C1CN(C=1C=CC(F)=CC=1)CC1=CC=CC=C1 OGIQXAWRYHWHLV-UHFFFAOYSA-N 0.000 claims 1
- IOQZJNXCWMQCQT-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)ethoxymethyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1COCCC1=CC=C(F)C=C1 IOQZJNXCWMQCQT-UHFFFAOYSA-N 0.000 claims 1
- OUCRCIGGGOIDGL-UHFFFAOYSA-N 5-[2-(4-fluorophenyl)ethyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1CCC1=CC=C(F)C=C1 OUCRCIGGGOIDGL-UHFFFAOYSA-N 0.000 claims 1
- XFQCLAQMOBBEHN-UHFFFAOYSA-N 5-[[(4-fluorophenyl)methylamino]methyl]-4-(hydroxymethyl)-n,3-bis(phenylmethoxy)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NOCC=2C=CC=CC=2)=C(OCC=2C=CC=CC=2)C(CO)=C1CNCC1=CC=C(F)C=C1 XFQCLAQMOBBEHN-UHFFFAOYSA-N 0.000 claims 1
- VYGXRZBKAJVIJW-UHFFFAOYSA-N 5-[[(4-fluorophenyl)methylamino]methyl]-n,3-dihydroxy-4-(methoxymethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(COC)=C1CNCC1=CC=C(F)C=C1 VYGXRZBKAJVIJW-UHFFFAOYSA-N 0.000 claims 1
- LKWPCCKVLOJHGM-UHFFFAOYSA-N 5-[[2-(4-fluorophenyl)ethylamino]methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1CNCCC1=CC=C(F)C=C1 LKWPCCKVLOJHGM-UHFFFAOYSA-N 0.000 claims 1
- BERJEDGQFJTHSB-UHFFFAOYSA-N 5-[[[1-(4-fluorophenyl)cyclopropyl]amino]methyl]-n,3-dihydroxy-4-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCC1=C(O)C(C(=O)NO)=NC=C1CNC1(C=2C=CC(F)=CC=2)CC1 BERJEDGQFJTHSB-UHFFFAOYSA-N 0.000 claims 1
- YIFXBRAJWVIDSQ-UHFFFAOYSA-N 5-[[[1-(4-fluorophenyl)cyclopropyl]amino]methyl]-n-hydroxy-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxamide Chemical compound C1=NC(C(=O)NO)=C2OC(C)(C)OCC2=C1CNC1(C=2C=CC(F)=CC=2)CC1 YIFXBRAJWVIDSQ-UHFFFAOYSA-N 0.000 claims 1
- IQPRDAUAWXZCAP-UHFFFAOYSA-N 5-n-[(4-fluorophenyl)methyl]-2-n,3-dihydroxy-4-(methoxymethyl)-5-n-methylpyridine-2,5-dicarboxamide Chemical compound COCC1=C(O)C(C(=O)NO)=NC=C1C(=O)N(C)CC1=CC=C(F)C=C1 IQPRDAUAWXZCAP-UHFFFAOYSA-N 0.000 claims 1
- PMYIEUBVAWDQRS-UHFFFAOYSA-N 8-methoxycarbonyl-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-5-carboxylic acid Chemical compound C1OC(C)(C)OC2=C1C(C(O)=O)=CN=C2C(=O)OC PMYIEUBVAWDQRS-UHFFFAOYSA-N 0.000 claims 1
- HHEQZPRWOKNUGB-UHFFFAOYSA-N C(C1=CC=CC=C1)OC1(NC=C(C(=C1OCC1=CC=CC=C1)COC)C(=O)N(C)CC1=CC=C(C=C1)F)C(=O)N Chemical compound C(C1=CC=CC=C1)OC1(NC=C(C(=C1OCC1=CC=CC=C1)COC)C(=O)N(C)CC1=CC=C(C=C1)F)C(=O)N HHEQZPRWOKNUGB-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UANCPYWCKCEGMY-UHFFFAOYSA-N [1,3]dioxepino[5,6-c]pyridine-8-carboxamide Chemical compound C=1OCOC=C2C=NC(=CC21)C(=O)N UANCPYWCKCEGMY-UHFFFAOYSA-N 0.000 claims 1
- QOKQOFNITUFRRW-UHFFFAOYSA-N [5-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridin-8-yl]methanol Chemical compound C1=CC(OC)=CC=C1COCC1=CN=C(CO)C2=C1COC(C)(C)O2 QOKQOFNITUFRRW-UHFFFAOYSA-N 0.000 claims 1
- SMAZAYYPTCCMNN-UHFFFAOYSA-N benzyl n-[8-(hydroxycarbamoyl)-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridin-5-yl]carbamate Chemical compound C1=NC(C(=O)NO)=C2OC(C)(C)OCC2=C1NC(=O)OCC1=CC=CC=C1 SMAZAYYPTCCMNN-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 claims 1
- WBJDHFGIDYKBFY-UHFFFAOYSA-N ethyl 5-[(4-methoxyphenyl)methoxymethyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylate Chemical compound C1=2COC(C)(C)OC=2C(C(=O)OCC)=NC=C1COCC1=CC=C(OC)C=C1 WBJDHFGIDYKBFY-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 229940125777 fusion inhibitor Drugs 0.000 claims 1
- FKWAGQMSVVCXTD-UHFFFAOYSA-N hydroxymethyl pyridine-2-carboxylate Chemical compound OCOC(=O)C1=CC=CC=N1 FKWAGQMSVVCXTD-UHFFFAOYSA-N 0.000 claims 1
- 229940124524 integrase inhibitor Drugs 0.000 claims 1
- 239000002850 integrase inhibitor Substances 0.000 claims 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 claims 1
- URLHVPBCFMDKLW-UHFFFAOYSA-N methyl 2,2-dimethyl-5-(phenylmethoxycarbonylamino)-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylate Chemical compound C1=2COC(C)(C)OC=2C(C(=O)OC)=NC=C1NC(=O)OCC1=CC=CC=C1 URLHVPBCFMDKLW-UHFFFAOYSA-N 0.000 claims 1
- DOAQXGHYQMKBOY-UHFFFAOYSA-N methyl 5-[(3-chloro-4-fluorophenoxy)methyl]-3-hydroxy-4-methylpyridine-2-carboxylate Chemical compound CC1=C(O)C(C(=O)OC)=NC=C1COC1=CC=C(F)C(Cl)=C1 DOAQXGHYQMKBOY-UHFFFAOYSA-N 0.000 claims 1
- HXDAYZDSBKOAIB-UHFFFAOYSA-N methyl 5-[(3-chloro-4-fluorophenoxy)methyl]-4-methyl-3-phenylmethoxypyridine-2-carboxylate Chemical compound CC1=C(OCC=2C=CC=CC=2)C(C(=O)OC)=NC=C1COC1=CC=C(F)C(Cl)=C1 HXDAYZDSBKOAIB-UHFFFAOYSA-N 0.000 claims 1
- CQKZEYRKXBYWMH-UHFFFAOYSA-N methyl 5-[(4-fluoroanilino)methyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylate Chemical compound C1=2COC(C)(C)OC=2C(C(=O)OC)=NC=C1CNC1=CC=C(F)C=C1 CQKZEYRKXBYWMH-UHFFFAOYSA-N 0.000 claims 1
- QTDDXBMFVGYZCO-UHFFFAOYSA-N methyl 5-[(4-fluorobenzoyl)amino]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylate Chemical compound C1=2COC(C)(C)OC=2C(C(=O)OC)=NC=C1NC(=O)C1=CC=C(F)C=C1 QTDDXBMFVGYZCO-UHFFFAOYSA-N 0.000 claims 1
- PYMCSSTUBKRYEV-UHFFFAOYSA-N methyl 5-[(4-fluorophenoxy)methyl]-3-hydroxy-4-methylpyridine-2-carboxylate Chemical compound CC1=C(O)C(C(=O)OC)=NC=C1COC1=CC=C(F)C=C1 PYMCSSTUBKRYEV-UHFFFAOYSA-N 0.000 claims 1
- OFBFJIULPCVGGD-UHFFFAOYSA-N methyl 5-[(4-fluorophenoxy)methyl]-4-methyl-3-phenylmethoxypyridine-2-carboxylate Chemical compound CC1=C(OCC=2C=CC=CC=2)C(C(=O)OC)=NC=C1COC1=CC=C(F)C=C1 OFBFJIULPCVGGD-UHFFFAOYSA-N 0.000 claims 1
- VYPJXHXXYSIJJQ-UHFFFAOYSA-N methyl 5-[(n-benzyl-4-fluoroanilino)methyl]-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylate Chemical compound C1=2COC(C)(C)OC=2C(C(=O)OC)=NC=C1CN(C=1C=CC(F)=CC=1)CC1=CC=CC=C1 VYPJXHXXYSIJJQ-UHFFFAOYSA-N 0.000 claims 1
- NIQGUQHFQIYPBH-UHFFFAOYSA-N methyl 5-[[(4-fluorophenyl)methylamino]methyl]-3-hydroxy-4-methylpyridine-2-carboxylate Chemical compound CC1=C(O)C(C(=O)OC)=NC=C1CNCC1=CC=C(F)C=C1 NIQGUQHFQIYPBH-UHFFFAOYSA-N 0.000 claims 1
- BWQCVSXBXPZTDM-UHFFFAOYSA-N methyl 5-[[2-(4-fluorophenyl)ethyl-(2-phenylmethoxyethyl)amino]methyl]-3-hydroxy-4-(hydroxymethyl)pyridine-2-carboxylate Chemical compound OCC1=C(O)C(C(=O)OC)=NC=C1CN(CCC=1C=CC(F)=CC=1)CCOCC1=CC=CC=C1 BWQCVSXBXPZTDM-UHFFFAOYSA-N 0.000 claims 1
- GLDIURMIXDXSMN-UHFFFAOYSA-N methyl 5-[[2-(4-fluorophenyl)ethylamino]methyl]-3-hydroxy-4-(hydroxymethyl)pyridine-2-carboxylate Chemical compound OCC1=C(O)C(C(=O)OC)=NC=C1CNCCC1=CC=C(F)C=C1 GLDIURMIXDXSMN-UHFFFAOYSA-N 0.000 claims 1
- RWOKJWJCJHASCE-UHFFFAOYSA-N methyl 5-amino-2,2-dimethyl-4h-[1,3]dioxino[4,5-c]pyridine-8-carboxylate Chemical compound C1OC(C)(C)OC2=C1C(N)=CN=C2C(=O)OC RWOKJWJCJHASCE-UHFFFAOYSA-N 0.000 claims 1
- DOPIHGXNYNUVIK-UHFFFAOYSA-N methyl n-[(4-fluorophenyl)methyl]-n-[[5-hydroxy-6-(hydroxycarbamoyl)-4-(hydroxymethyl)pyridin-3-yl]methyl]carbamate Chemical compound C=1N=C(C(=O)NO)C(O)=C(CO)C=1CN(C(=O)OC)CC1=CC=C(F)C=C1 DOPIHGXNYNUVIK-UHFFFAOYSA-N 0.000 claims 1
- SULNVRMLCGEGOP-UHFFFAOYSA-N n,3-dihydroxy-4-(hydroxymethyl)-5-(3-phenylpropyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(CO)=C1CCCC1=CC=CC=C1 SULNVRMLCGEGOP-UHFFFAOYSA-N 0.000 claims 1
- IYSMIXWJEMGJER-UHFFFAOYSA-N n,3-dihydroxy-4-methyl-5-(phenylmethoxymethyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)NO)=C(O)C(C)=C1COCC1=CC=CC=C1 IYSMIXWJEMGJER-UHFFFAOYSA-N 0.000 claims 1
- PUDHXWRUZWDLMF-UHFFFAOYSA-N n-(hydroxymethyl)pyridine-2-carboxamide Chemical compound OCNC(=O)C1=CC=CC=N1 PUDHXWRUZWDLMF-UHFFFAOYSA-N 0.000 claims 1
- DIYCGWYFFTUVSY-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-(hydroxymethyl)-6-methyl-5-phenylmethoxypyridine-3-carboxamide Chemical compound OCC1=C(OCC=2C=CC=CC=2)C(C)=NC=C1C(=O)NCC1=CC=C(F)C=C1 DIYCGWYFFTUVSY-UHFFFAOYSA-N 0.000 claims 1
- VXISHIPREGYKAR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-(methoxymethyl)-n,6-dimethyl-1-oxido-5-phenylmethoxypyridin-1-ium-3-carboxamide Chemical compound COCC1=C(C(=O)N(C)CC=2C=CC(F)=CC=2)C=[N+]([O-])C(C)=C1OCC1=CC=CC=C1 VXISHIPREGYKAR-UHFFFAOYSA-N 0.000 claims 1
- CHZKNDYUAXGPLQ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-4-(methoxymethyl)-n,6-dimethyl-5-phenylmethoxypyridine-3-carboxamide Chemical compound COCC1=C(C(=O)N(C)CC=2C=CC(F)=CC=2)C=NC(C)=C1OCC1=CC=CC=C1 CHZKNDYUAXGPLQ-UHFFFAOYSA-N 0.000 claims 1
- UVCLMUJRGGBZMC-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-(hydroxymethyl)-4-(methoxymethyl)-n-methyl-5-phenylmethoxypyridine-3-carboxamide Chemical compound OCC1=NC=C(C(=O)N(C)CC=2C=CC(F)=CC=2)C(COC)=C1OCC1=CC=CC=C1 UVCLMUJRGGBZMC-UHFFFAOYSA-N 0.000 claims 1
- RCGUCLKOFVJBQW-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-6-formyl-4-(methoxymethyl)-n-methyl-5-phenylmethoxypyridine-3-carboxamide Chemical compound O=CC1=NC=C(C(=O)N(C)CC=2C=CC(F)=CC=2)C(COC)=C1OCC1=CC=CC=C1 RCGUCLKOFVJBQW-UHFFFAOYSA-N 0.000 claims 1
- 230000035515 penetration Effects 0.000 claims 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 1
- LKRWOEFFDOHCBS-UHFFFAOYSA-N tert-butyl n-[(4-fluorophenyl)methyl]-n-[[5-hydroxy-6-(hydroxycarbamoyl)-4-methylpyridin-3-yl]methyl]carbamate Chemical compound C1=NC(C(=O)NO)=C(O)C(C)=C1CN(C(=O)OC(C)(C)C)CC1=CC=C(F)C=C1 LKRWOEFFDOHCBS-UHFFFAOYSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 12
- 0 **(N)Ic1cnc(C(NO*)=O)c(C2SC2)c1[Bh] Chemical compound **(N)Ic1cnc(C(NO*)=O)c(C2SC2)c1[Bh] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13087408P | 2008-06-04 | 2008-06-04 | |
| US61/130,874 | 2008-06-04 |
Publications (1)
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|---|---|
| RU2010153656A true RU2010153656A (ru) | 2012-07-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| RU2010153656/04A RU2010153656A (ru) | 2008-06-04 | 2009-06-04 | Ингибиторы интегразы вич из пиридоксина |
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| EP (1) | EP2300433A4 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5514810B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN102112447B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2009253812A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2726742A1 (cg-RX-API-DMAC7.html) |
| RU (1) | RU2010153656A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009146555A1 (cg-RX-API-DMAC7.html) |
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| AU2007337830A1 (en) * | 2006-09-21 | 2008-07-03 | Ambrilia Biopharma Inc. | Benzenesulfonamide derivatives as HIV protease inhibitors |
| EP2126574B1 (en) | 2007-03-08 | 2015-12-23 | The Board of Trustees of the Leland Stanford Junior University | Mitochondrial aldehyde dehydrogenase-2 modulators and methods of use thereof |
| ES2477552T3 (es) | 2008-09-08 | 2014-07-17 | The Board Of Trustees Of The Leland Stanford Junior University | Moduladores de la actividad de la aldehidodeshidrogenasa y métodos de uso de los mismos |
| WO2010062308A1 (en) | 2008-10-28 | 2010-06-03 | The Board Of Trustees Of The Leland Stanford Junior University | Modulators of aldehyde dehydrogenase and methods of use thereof |
| US8283366B2 (en) | 2010-01-22 | 2012-10-09 | Ambrilia Biopharma, Inc. | Derivatives of pyridoxine for inhibiting HIV integrase |
| US10457659B2 (en) | 2011-04-29 | 2019-10-29 | The Board Of Trustees Of The Leland Stanford Junior University | Compositions and methods for increasing proliferation of adult salivary stem cells |
| ES2790358T3 (es) | 2011-12-28 | 2020-10-27 | Global Blood Therapeutics Inc | Compuestos de heteroaril aldehído sustituido y métodos para su uso en el aumento de la oxigenación tisular |
| SI3738434T1 (sl) | 2011-12-28 | 2024-01-31 | Global Blood Therapeutics, Inc. | Vmesne spojine za pridobivanje substituiranih benzaldehidnih spojin in postopki njihove uporabe pri povečanju oksigenacije tkiv |
| KR20150135332A (ko) | 2013-03-14 | 2015-12-02 | 더 보드 오브 트러스티스 오브 더 리랜드 스탠포드 쥬니어 유니버시티 | 미토콘드리아 알데히드 탈수소효소-2 조절인자들 및 이들의 사용 방법 |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| SG11201507453VA (en) | 2013-03-15 | 2015-10-29 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| EP2970196B1 (en) | 2013-03-15 | 2020-11-25 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US10100043B2 (en) | 2013-03-15 | 2018-10-16 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9981939B2 (en) | 2013-03-15 | 2018-05-29 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| DK3102208T4 (da) | 2014-02-07 | 2024-08-26 | Global Blood Therapeutics Inc | Krystallinsk polymorph af den frie base af 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyd |
| 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 |
| ES3039236T3 (en) | 2015-12-04 | 2025-10-20 | Global Blood Therapeutics Inc | Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| US12084472B2 (en) | 2015-12-18 | 2024-09-10 | Ardelyx, Inc. | Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists |
| TWI773657B (zh) | 2015-12-18 | 2022-08-11 | 美商亞德利克斯公司 | 作爲非全身ｔｇｒ５促效劑之經取代之4-苯基吡啶化合物 |
| TWI663160B (zh) | 2016-05-12 | 2019-06-21 | 全球血液治療公司 | 用於合成2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)-吡啶-3-基)甲氧基)苯甲醛之方法 |
| TW202332423A (zh) | 2016-10-12 | 2023-08-16 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| CN108203439B (zh) * | 2016-12-20 | 2020-04-14 | 四川大学 | 苯乙烯吡啶类化合物、其制备方法和用途 |
| RU2641309C1 (ru) * | 2017-07-24 | 2018-01-17 | федеральное государственное автономное образовательное учреждение высшего образования "Казанский (Приволжский) федеральный университет" (ФГАОУ ВО КФУ) | Антисептическое лекарственное средство |
| WO2019084681A1 (en) | 2017-10-30 | 2019-05-09 | Montreal Heart Institute | Methods of treating elevated plasma cholesterol |
| US11014884B2 (en) | 2018-10-01 | 2021-05-25 | Global Blood Therapeutics, Inc. | Modulators of hemoglobin |
| JP7554768B2 (ja) * | 2019-04-11 | 2024-09-20 | ヤンセン ファーマシューティカ エヌ．ベー． | Ｍａｌｔ１阻害剤としての尿素誘導体 |
| WO2020237374A1 (en) * | 2019-05-28 | 2020-12-03 | Montreal Heart Institute | Picolinic acid derivatives and use thereof for treating diseases associated with elevated cholesterol |
| CN113116890B (zh) * | 2021-04-25 | 2022-06-03 | 西南大学 | 5-Pyridoxolactone用于制备抑制家蚕核型多角体病毒的药物中的应用 |
| CN117343006B (zh) * | 2023-10-08 | 2024-07-09 | 河南科技大学 | 一种arb-272572的制备方法 |
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|---|---|---|---|---|
| US6107291A (en) | 1997-12-19 | 2000-08-22 | Amgen Inc. | Azepine or larger medium ring derivatives and methods of use |
| EP1004578B1 (en) * | 1998-11-05 | 2004-02-25 | Pfizer Products Inc. | 5-oxo-pyrrolidine-2-carboxylic acid hydroxamide derivatives |
| PA8586801A1 (es) | 2002-10-31 | 2005-02-04 | Pfizer | Inhibidores de hiv-integrasa, composiciones farmaceuticas y metodos para su uso |
| NZ542711A (en) * | 2003-08-20 | 2008-03-28 | Pharmacyclics Inc | Acetylene derivatives as inhibitors of histone deacetylase |
| WO2005103003A2 (en) * | 2004-04-26 | 2005-11-03 | Pfizer Inc. | Pyrrolopyridine derivatives and their use as hiv-integrase inhibitors |
| AU2006234441B2 (en) * | 2005-04-08 | 2011-07-07 | Daiichi Sankyo Company, Limited | Pyridylmethylsulfone derivative |
-
2009
- 2009-06-04 EP EP09757017A patent/EP2300433A4/en not_active Withdrawn
- 2009-06-04 JP JP2011511948A patent/JP5514810B2/ja not_active Expired - Fee Related
- 2009-06-04 US US12/995,890 patent/US8742123B2/en not_active Expired - Fee Related
- 2009-06-04 WO PCT/CA2009/000787 patent/WO2009146555A1/en not_active Ceased
- 2009-06-04 RU RU2010153656/04A patent/RU2010153656A/ru unknown
- 2009-06-04 AU AU2009253812A patent/AU2009253812A1/en not_active Abandoned
- 2009-06-04 CN CN2009801304571A patent/CN102112447B/zh not_active Expired - Fee Related
- 2009-06-04 CA CA2726742A patent/CA2726742A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP5514810B2 (ja) | 2014-06-04 |
| US20110178120A1 (en) | 2011-07-21 |
| AU2009253812A1 (en) | 2009-12-10 |
| EP2300433A4 (en) | 2012-03-07 |
| JP2011521979A (ja) | 2011-07-28 |
| CN102112447A (zh) | 2011-06-29 |
| WO2009146555A1 (en) | 2009-12-10 |
| EP2300433A1 (en) | 2011-03-30 |
| WO2009146555A8 (en) | 2010-12-23 |
| CN102112447B (zh) | 2013-06-26 |
| US8742123B2 (en) | 2014-06-03 |
| CA2726742A1 (en) | 2009-12-10 |
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