RU2010125220A - Ненуклеозидные ингибиторы обратной транскриптазы - Google Patents
Ненуклеозидные ингибиторы обратной транскриптазы Download PDFInfo
- Publication number
- RU2010125220A RU2010125220A RU2010125220/04A RU2010125220A RU2010125220A RU 2010125220 A RU2010125220 A RU 2010125220A RU 2010125220/04 A RU2010125220/04 A RU 2010125220/04A RU 2010125220 A RU2010125220 A RU 2010125220A RU 2010125220 A RU2010125220 A RU 2010125220A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- independently
- haloalkyl
- pyridin
- chloro
- Prior art date
Links
- 229940042402 non-nucleoside reverse transcriptase inhibitor Drugs 0.000 title 1
- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 claims abstract 43
- 125000001424 substituent group Chemical group 0.000 claims abstract 38
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 26
- 150000002367 halogens Chemical class 0.000 claims abstract 20
- 239000000651 prodrug Substances 0.000 claims abstract 20
- 229940002612 prodrug Drugs 0.000 claims abstract 20
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract 8
- 125000003118 aryl group Chemical group 0.000 claims abstract 7
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 6
- 101100273648 Mus musculus Ccna2 gene Proteins 0.000 claims abstract 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims abstract 4
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims abstract 3
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims 139
- 229910052739 hydrogen Inorganic materials 0.000 claims 35
- -1 1-azetidinyl Chemical group 0.000 claims 24
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 12
- 229910052794 bromium Inorganic materials 0.000 claims 12
- 229910052801 chlorine Inorganic materials 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000001624 naphthyl group Chemical group 0.000 claims 10
- 229910052731 fluorine Inorganic materials 0.000 claims 8
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- GMCYQWDQLIDMII-UHFFFAOYSA-N 3-(3,5-dichlorophenoxy)-1-(2h-pyrazolo[3,4-b]pyridin-3-ylmethyl)-4-(trifluoromethyl)pyridin-2-one Chemical compound FC(F)(F)C=1C=CN(CC=2C3=CC=CN=C3NN=2)C(=O)C=1OC1=CC(Cl)=CC(Cl)=C1 GMCYQWDQLIDMII-UHFFFAOYSA-N 0.000 claims 4
- KHIUGRYFNXHUBT-UHFFFAOYSA-N 3-[1-[(6-amino-2h-pyrazolo[3,4-b]pyridin-3-yl)methyl]-4-chloro-2-oxopyridin-3-yl]oxy-5-chlorobenzonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N=1NC2=NC(N)=CC=C2C=1CN(C1=O)C=CC(Cl)=C1OC1=CC(Cl)=CC(C#N)=C1 KHIUGRYFNXHUBT-UHFFFAOYSA-N 0.000 claims 4
- CVAURPNMBSXXSS-UHFFFAOYSA-N 3-chloro-5-[2-oxo-1-(2h-pyrazolo[3,4-b]pyridin-3-ylmethyl)-4-(trifluoromethyl)pyridin-3-yl]oxybenzonitrile Chemical compound FC(F)(F)C=1C=CN(CC=2C3=CC=CN=C3NN=2)C(=O)C=1OC1=CC(Cl)=CC(C#N)=C1 CVAURPNMBSXXSS-UHFFFAOYSA-N 0.000 claims 4
- XUIZIBCKVKBTGV-UHFFFAOYSA-N 3-chloro-5-[4-methyl-2-oxo-1-[2-(2h-pyrazolo[3,4-b]pyridin-3-yl)ethyl]pyridin-3-yl]oxybenzonitrile Chemical compound CC=1C=CN(CCC=2C3=CC=CN=C3NN=2)C(=O)C=1OC1=CC(Cl)=CC(C#N)=C1 XUIZIBCKVKBTGV-UHFFFAOYSA-N 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 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 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- ATGKQOUKJPVTKE-UHFFFAOYSA-N 2-[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1-yl]-n-[(2-chlorophenyl)methyl]-n-methylacetamide Chemical compound C1=CC(C(F)(F)F)=C(OC=2C=C(C=C(Cl)C=2)C#N)C(=O)N1CC(=O)N(C)CC1=CC=CC=C1Cl ATGKQOUKJPVTKE-UHFFFAOYSA-N 0.000 claims 2
- TXIDGJNYVPGVEG-UHFFFAOYSA-N 3-[[6-[2-(6-amino-2h-pyrazolo[3,4-b]pyridin-3-yl)ethyl]-3-chloro-2-oxo-1h-pyridin-4-yl]oxy]-5-chlorobenzonitrile Chemical compound N=1NC2=NC(N)=CC=C2C=1CCC(NC(=O)C=1Cl)=CC=1OC1=CC(Cl)=CC(C#N)=C1 TXIDGJNYVPGVEG-UHFFFAOYSA-N 0.000 claims 2
- ABOZXYNAPFTBHX-UHFFFAOYSA-N 3-chloro-5-[4,5-dichloro-2-oxo-1-(2h-pyrazolo[3,4-b]pyridin-3-ylmethyl)pyridin-3-yl]oxybenzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC=2C(N(CC=3C4=CC=CN=C4NN=3)C=C(Cl)C=2Cl)=O)=C1 ABOZXYNAPFTBHX-UHFFFAOYSA-N 0.000 claims 2
- YMRUCOCNLHJFRC-UHFFFAOYSA-N 3-chloro-5-[4-methyl-2-oxo-1-(2h-pyrazolo[3,4-b]pyridin-3-ylmethyl)pyridin-3-yl]oxybenzonitrile Chemical compound CC=1C=CN(CC=2C3=CC=CN=C3NN=2)C(=O)C=1OC1=CC(Cl)=CC(C#N)=C1 YMRUCOCNLHJFRC-UHFFFAOYSA-N 0.000 claims 2
- RRYPCILBOZGVEJ-UHFFFAOYSA-N 3-chloro-5-[5-chloro-2-[2-(2h-pyrazolo[3,4-b]pyridin-3-yl)ethyl]pyridin-4-yl]oxybenzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC=2C(=CN=C(CCC=3C4=CC=CN=C4NN=3)C=2)Cl)=C1 RRYPCILBOZGVEJ-UHFFFAOYSA-N 0.000 claims 2
- GIOABAWLXRZDTF-UHFFFAOYSA-N 3-chloro-5-[[2-oxo-6-[2-(2h-pyrazolo[3,4-b]pyridin-3-yl)ethyl]-1h-pyridin-4-yl]oxy]benzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC2=CC(=O)NC(CCC=3C4=CC=CN=C4NN=3)=C2)=C1 GIOABAWLXRZDTF-UHFFFAOYSA-N 0.000 claims 2
- MEFSIZQEXHEOCA-UHFFFAOYSA-N 3-chloro-5-[[3,5-dichloro-2-oxo-6-[2-(2h-pyrazolo[3,4-b]pyridin-3-yl)ethyl]-1h-pyridin-4-yl]oxy]benzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC2=C(C(=O)NC(CCC=3C4=CC=CN=C4NN=3)=C2Cl)Cl)=C1 MEFSIZQEXHEOCA-UHFFFAOYSA-N 0.000 claims 2
- KDKUQACKJMWZJZ-UHFFFAOYSA-N 3-chloro-5-[[3-chloro-2-oxo-6-(2h-pyrazolo[3,4-b]pyridin-3-ylmethylamino)-1h-pyridin-4-yl]oxy]benzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC2=C(C(=O)NC(NCC=3C4=CC=CN=C4NN=3)=C2)Cl)=C1 KDKUQACKJMWZJZ-UHFFFAOYSA-N 0.000 claims 2
- GZVLIXZYBWGUTC-UHFFFAOYSA-N 3-chloro-5-[[3-chloro-2-oxo-6-[(2-oxo-3h-benzimidazol-1-yl)methyl]-1h-pyridin-4-yl]oxy]benzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC2=C(C(=O)NC(CN3C(NC4=CC=CC=C43)=O)=C2)Cl)=C1 GZVLIXZYBWGUTC-UHFFFAOYSA-N 0.000 claims 2
- NCPJKBVDFNPLLG-UHFFFAOYSA-N 3-chloro-5-[[3-chloro-2-oxo-6-[2-(2h-pyrazolo[3,4-b]pyridin-3-yl)ethyl]-1h-pyridin-4-yl]oxy]benzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC2=C(C(=O)NC(CCC=3C4=CC=CN=C4NN=3)=C2)Cl)=C1 NCPJKBVDFNPLLG-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- YIQIGLZIZPIAGP-UHFFFAOYSA-N 1-[(3-methyl-4-phenoxypyridin-2-yl)methyl]benzimidazole Chemical compound C1=CN=C(CN2C3=CC=CC=C3N=C2)C(C)=C1OC1=CC=CC=C1 YIQIGLZIZPIAGP-UHFFFAOYSA-N 0.000 claims 1
- RHQXZNCCZYCFFV-UHFFFAOYSA-N 2-[3-(3-bromo-5-chlorophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1-yl]-n-(2-chloro-4-sulfamoylphenyl)acetamide Chemical compound ClC1=CC(S(=O)(=O)N)=CC=C1NC(=O)CN1C(=O)C(OC=2C=C(Br)C=C(Cl)C=2)=C(C(F)(F)F)C=C1 RHQXZNCCZYCFFV-UHFFFAOYSA-N 0.000 claims 1
- IMRGEQIRLWFLPC-UHFFFAOYSA-N 2-[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1-yl]-n-(2-chloro-4-sulfamoylphenyl)acetamide Chemical compound ClC1=CC(S(=O)(=O)N)=CC=C1NC(=O)CN1C(=O)C(OC=2C=C(C=C(Cl)C=2)C#N)=C(C(F)(F)F)C=C1 IMRGEQIRLWFLPC-UHFFFAOYSA-N 0.000 claims 1
- YXVABPSUOVOEJJ-UHFFFAOYSA-N 2-methyl-6-[(6-phenoxypyridin-2-yl)methyl]pyridine Chemical compound CC1=CC=CC(CC=2N=C(OC=3C=CC=CC=3)C=CC=2)=N1 YXVABPSUOVOEJJ-UHFFFAOYSA-N 0.000 claims 1
- FTFUKUWGDBEIJI-UHFFFAOYSA-N 3-chloro-5-[3-chloro-2,5-difluoro-6-(2h-pyrazolo[3,4-b]pyridin-3-ylmethylamino)pyridin-4-yl]oxybenzonitrile Chemical compound ClC=1C(F)=NC(NCC=2C3=CC=CN=C3NN=2)=C(F)C=1OC1=CC(Cl)=CC(C#N)=C1 FTFUKUWGDBEIJI-UHFFFAOYSA-N 0.000 claims 1
- ZSDYTNJSFLYICM-UHFFFAOYSA-N 3-chloro-5-[4-chloro-2-oxo-1-(2h-pyrazolo[3,4-b]pyridin-3-ylmethyl)pyridin-3-yl]oxybenzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC=2C(N(CC=3C4=CC=CN=C4NN=3)C=CC=2Cl)=O)=C1 ZSDYTNJSFLYICM-UHFFFAOYSA-N 0.000 claims 1
- CCEYNDRKIOXUGP-UHFFFAOYSA-N 3-chloro-5-[[3-chloro-2-oxo-6-(2h-pyrazolo[3,4-b]pyridin-3-ylmethyl)-1h-pyridin-4-yl]oxy]benzonitrile Chemical compound N#CC1=CC(Cl)=CC(OC2=C(C(=O)NC(CC=3C4=CC=CN=C4NN=3)=C2)Cl)=C1 CCEYNDRKIOXUGP-UHFFFAOYSA-N 0.000 claims 1
- CBFKUUGIHWKPLR-UHFFFAOYSA-N 5-[2-oxo-1-(2h-pyrazolo[3,4-b]pyridin-3-ylmethyl)-4-(trifluoromethyl)pyridin-3-yl]oxybenzene-1,3-dicarbonitrile Chemical compound FC(F)(F)C=1C=CN(CC=2C3=CC=CN=C3NN=2)C(=O)C=1OC1=CC(C#N)=CC(C#N)=C1 CBFKUUGIHWKPLR-UHFFFAOYSA-N 0.000 claims 1
- 241000282326 Felis catus Species 0.000 claims 1
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 claims 1
- 229940099797 HIV integrase inhibitor Drugs 0.000 claims 1
- 229940122313 Nucleoside reverse transcriptase inhibitor Drugs 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002835 hiv fusion inhibitor Substances 0.000 claims 1
- 239000003084 hiv integrase inhibitor Substances 0.000 claims 1
- 239000004030 hiv protease inhibitor Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000010348 incorporation Methods 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 239000002777 nucleoside Substances 0.000 claims 1
- 150000003833 nucleoside derivatives Chemical class 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000006574 non-aromatic ring group Chemical group 0.000 abstract 1
- 0 *N(C(N=I(C=C1)=C)=C1N1N)C1=O Chemical compound *N(C(N=I(C=C1)=C)=C1N1N)C1=O 0.000 description 3
- RBJOYUAKTJHSNU-UHFFFAOYSA-N NN(c(cccn1)c1O1)C1=O Chemical compound NN(c(cccn1)c1O1)C1=O RBJOYUAKTJHSNU-UHFFFAOYSA-N 0.000 description 1
- SBMSLRMNBSMKQC-UHFFFAOYSA-N NN1CCCC1 Chemical compound NN1CCCC1 SBMSLRMNBSMKQC-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US376907P | 2007-11-20 | 2007-11-20 | |
| US61/003,769 | 2007-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2010125220A true RU2010125220A (ru) | 2011-12-27 |
Family
ID=40336474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2010125220/04A RU2010125220A (ru) | 2007-11-20 | 2008-11-14 | Ненуклеозидные ингибиторы обратной транскриптазы |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8404856B2 (enExample) |
| EP (1) | EP2222661B1 (enExample) |
| JP (1) | JP5539216B2 (enExample) |
| KR (1) | KR20100088142A (enExample) |
| CN (1) | CN101952274A (enExample) |
| AU (1) | AU2008326784B2 (enExample) |
| BR (1) | BRPI0820162A2 (enExample) |
| CA (1) | CA2705834A1 (enExample) |
| IL (1) | IL205386A0 (enExample) |
| MX (1) | MX2010005483A (enExample) |
| RU (1) | RU2010125220A (enExample) |
| WO (1) | WO2009067166A2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010026075A1 (en) * | 2008-09-04 | 2010-03-11 | F. Hoffmann-La Roche Ag | Pyridine derivatives as inhibitors of hiv-i reverse transcriptase |
| CN102666537A (zh) * | 2009-10-20 | 2012-09-12 | 艾格尔生物制药股份有限公司 | 治疗黄病毒科病毒感染的氮杂吲唑 |
| HUE025336T2 (en) * | 2010-03-30 | 2016-03-29 | Merck Canada Inc | Non-nucleoside reverse transcriptase inhibitors |
| WO2011126969A1 (en) * | 2010-04-08 | 2011-10-13 | Merck Sharp & Dohme Corp. | Prodrugs of an hiv reverse transcriptase inhibitor |
| BR112015005997A8 (pt) * | 2012-09-26 | 2023-04-11 | Merck Sharp & Dohme | Composto |
| JO3470B1 (ar) * | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| EP2928472B1 (en) * | 2012-12-05 | 2018-05-02 | Merck Sharp & Dohme Corp. | Process for making reverse transcriptase inhibitors |
| BR112016012658B1 (pt) * | 2013-12-04 | 2022-06-21 | Merck Sharp & Dohme Corp | Métodos para sintetizar inibidores da transcriptase reversa e composto |
| PL3125894T3 (pl) * | 2014-04-01 | 2021-02-08 | Merck Sharp & Dohme Corp. | Proleki inhibitorów odwrotnej transkryptazy hiv |
| EP3180335B1 (en) | 2014-08-11 | 2021-05-05 | Angion Biomedica Corporation | Cytochrome p450 inhibitors and uses thereof |
| CA2970819A1 (en) | 2014-12-31 | 2016-07-07 | Angion Biomedica Corp. | Methods and agents for treating disease |
| MX391226B (es) * | 2015-09-23 | 2025-03-21 | Merck Sharp & Dohme Llc | Inhibidores de transcriptasa inversa de nucleosido 4'-substituido y preparaciones de los mismos. |
| CN108473495B (zh) | 2015-11-20 | 2022-04-12 | 福马治疗有限公司 | 作为泛素-特异性蛋白酶1抑制剂的嘌呤酮 |
| KR102590848B1 (ko) | 2016-12-28 | 2023-10-19 | 다트 뉴로사이언스, 엘엘씨 | Pde2 억제제로서 치환된 피라졸로피리미디논 화합물 |
| DK3717488T3 (da) | 2017-11-27 | 2021-12-13 | Dart Neuroscience Llc | Substituerede furanopyrimidinforbindelser som pde1-inhibitorer |
| PE20211704A1 (es) | 2018-12-18 | 2021-09-01 | Merck Sharp & Dohme | Derivados de pirimidona como agentes citotoxicos selectivos contra celulas infectadas por vih |
| US20220242847A1 (en) * | 2019-05-22 | 2022-08-04 | Merck Sharp & Dohme Corp. | Pyridinone derivatives as selective cytotoxic agents against hiv infected cells |
| CN110066273A (zh) * | 2019-06-05 | 2019-07-30 | 山东大学 | 一种含三氮唑环的单芳基嘧啶类hiv-1逆转录酶抑制剂及其制备方法与应用 |
| CN112876409A (zh) * | 2021-01-20 | 2021-06-01 | 都创(上海)医药科技股份有限公司 | 一种2-(5-溴-6-甲氧基吡啶-2-基)乙腈及其衍生物的合成方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL99731A0 (en) * | 1990-10-18 | 1992-08-18 | Merck & Co Inc | Hydroxylated pyridine derivatives,their preparation and pharmaceutical compositions containing them |
| JP3775685B2 (ja) * | 1993-07-28 | 2006-05-17 | ローン−プーラン・ロレ・リミテツド | Ｐｄｅ▲ｉｖ▼およびｔｎｆ抑制剤としての化合物 |
| RU2000129671A (ru) * | 1998-04-27 | 2004-02-20 | Сантр Насьональ Де Ля Решерш Сьентифик (Fr) | Производные 3-(амино- или аминоалкил) пиридинона и их применение для лечения болезней, связанных с ВИЧ |
| GB9910577D0 (en) | 1999-05-08 | 1999-07-07 | Zeneca Ltd | Chemical compounds |
| SE9904045D0 (sv) | 1999-11-09 | 1999-11-09 | Astra Ab | Compounds |
| US6800651B2 (en) | 2000-02-03 | 2004-10-05 | Eli Lilly And Company | Potentiators of glutamate receptors |
| WO2002022605A1 (en) * | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002024650A2 (en) * | 2000-09-19 | 2002-03-28 | Centre National De La Recherche Scientifique (Cnrs) | Pyridinone and pyridinethione derivatives having hiv inhibiting properties |
| GB0129260D0 (en) | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| ATE448784T1 (de) * | 2002-02-14 | 2009-12-15 | Pharmacia Corp | Substituierte pyridinone als modulatoren für p38 map kinase |
| BRPI0407329A (pt) * | 2003-02-07 | 2006-01-10 | Janssen Pharmaceutica Nv | Derivados de pirimidina para a prevenção de infecção de hiv |
| CN100469769C (zh) | 2003-03-24 | 2009-03-18 | 弗·哈夫曼-拉罗切有限公司 | 作为逆转录酶抑制剂的苄基-哒嗪酮 |
| US20050014774A1 (en) * | 2003-04-28 | 2005-01-20 | Richard Storer | Oxo-pyrimidine compounds |
| US7166738B2 (en) | 2004-04-23 | 2007-01-23 | Roche Palo Alto Llc | Non-nucleoside reverse transcriptase inhibitors |
| BRPI0510059B8 (pt) | 2004-04-23 | 2021-05-25 | Hoffmann La Roche | inibidores da transcriptase reversa não-nucleosídica e seus usos |
| TWI360539B (en) * | 2004-10-28 | 2012-03-21 | Shionogi & Co | 3-carbamoyl-2-pyridone derivatives |
| CA2592092A1 (en) | 2004-12-22 | 2006-06-29 | Pfizer Limited | Nonnucleoside inhibitors of hiv-1 reverse transcriptase |
| AR057455A1 (es) * | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
| CA2625039A1 (en) | 2005-10-19 | 2007-04-26 | F. Hoffmann-La Roche Ag | N-phenyl phenylacetamide non-nucleoside reverse transcriptase inihibitors |
| CN101291905A (zh) | 2005-10-19 | 2008-10-22 | 弗·哈夫曼-拉罗切有限公司 | 苯乙酰胺nnrt抑制剂 |
| EP2038272B8 (en) * | 2006-06-30 | 2013-10-23 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl pdk1 inhibitors |
| US8314119B2 (en) * | 2006-11-06 | 2012-11-20 | Abbvie Inc. | Azaadamantane derivatives and methods of use |
| TW200831085A (en) | 2006-12-13 | 2008-08-01 | Merck & Co Inc | Non-nucleoside reverse transcriptase inhibitors |
| US20080194545A1 (en) * | 2007-02-08 | 2008-08-14 | Trius Therapeutics | Antimicrobial compositions and methods of use |
-
2008
- 2008-11-14 KR KR1020107011127A patent/KR20100088142A/ko not_active Withdrawn
- 2008-11-14 AU AU2008326784A patent/AU2008326784B2/en not_active Ceased
- 2008-11-14 CA CA2705834A patent/CA2705834A1/en active Pending
- 2008-11-14 BR BRPI0820162A patent/BRPI0820162A2/pt not_active IP Right Cessation
- 2008-11-14 MX MX2010005483A patent/MX2010005483A/es not_active Application Discontinuation
- 2008-11-14 WO PCT/US2008/012774 patent/WO2009067166A2/en not_active Ceased
- 2008-11-14 US US12/742,159 patent/US8404856B2/en active Active
- 2008-11-14 EP EP08851089.6A patent/EP2222661B1/en not_active Not-in-force
- 2008-11-14 JP JP2010534947A patent/JP5539216B2/ja not_active Expired - Fee Related
- 2008-11-14 RU RU2010125220/04A patent/RU2010125220A/ru unknown
- 2008-11-14 CN CN2008801168055A patent/CN101952274A/zh active Pending
-
2010
- 2010-04-27 IL IL205386A patent/IL205386A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009067166A2 (en) | 2009-05-28 |
| WO2009067166A3 (en) | 2009-07-16 |
| JP5539216B2 (ja) | 2014-07-02 |
| JP2011503230A (ja) | 2011-01-27 |
| US8404856B2 (en) | 2013-03-26 |
| EP2222661A2 (en) | 2010-09-01 |
| EP2222661B1 (en) | 2016-04-20 |
| AU2008326784A1 (en) | 2009-05-28 |
| CN101952274A (zh) | 2011-01-19 |
| CA2705834A1 (en) | 2009-05-28 |
| BRPI0820162A2 (pt) | 2019-09-24 |
| US20100256181A1 (en) | 2010-10-07 |
| KR20100088142A (ko) | 2010-08-06 |
| MX2010005483A (es) | 2010-06-11 |
| IL205386A0 (en) | 2010-12-30 |
| AU2008326784B2 (en) | 2014-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2010125220A (ru) | Ненуклеозидные ингибиторы обратной транскриптазы | |
| JP2011503230A5 (enExample) | ||
| RU2012126989A (ru) | 2-амино-5,5-дифтор-5,6-дигидро-4н-оксазины в качестве ингибиторов васе 1 и(или) васе 2 | |
| JP2016516791A5 (enExample) | ||
| HRP20221454T1 (hr) | Piridinamin-piridonski i pirimidinamin-piridonski spojevi | |
| JP2012525395A5 (enExample) | ||
| JP2016519096A5 (enExample) | ||
| JP2017505794A5 (enExample) | ||
| JP2017513932A5 (enExample) | ||
| JP2016525075A5 (enExample) | ||
| RU2005103618A (ru) | Ингибирующие циклооксигеназу-2 (цог-2) производные пиридина | |
| RU2012116877A (ru) | Соединения 2-пиридона, применяемые в качестве ингибиторов нейтрофильной эластазы | |
| HRP20201430T1 (hr) | Spojevi 6-heterociklil-4-morfolin-4-ilpiridin-2-ona korisni za liječenje karcinoma i dijabetesa | |
| RU2008110949A (ru) | Соединения и композиции-иммуносупрессанты | |
| HRP20220096T1 (hr) | Inhibitori lizin specifične demetilaze-1 | |
| RU2008117329A (ru) | Производные имидазопиридина как антагонисты аденозинового рецептора а2в | |
| RU2016141646A (ru) | Ингибиторы trka киназы, основанные на них композиции и способы | |
| RU2003111754A (ru) | Производные пиридина с активностью ингибирования /кв-киназы (/кк-бета) | |
| SI3106463T1 (en) | Compounds of substituted pyrazolo (1,5-) pyrimidine as inhibitors of TRK kinase | |
| RU2008112691A (ru) | Азотсодержащее гетероциклическое соединение и его фармацевтическое применение | |
| RU2013132930A (ru) | Производное пиразола | |
| RU2015102057A (ru) | НОВЫЕ КОНДЕНСИРОВАННЫЕ ПИРИДИНОВЫЕ ПРОИЗВОДНЫЕ, ПРИМЕНИМЫЕ В КАЧЕСТВЕ ИНГИБИТОРОВ ТИРОЗИНКИНАЗЫ с-MET | |
| RU2015100942A (ru) | Производное пиперидинилпиразолпиридина | |
| RU2013154117A (ru) | Производные 1-фенил-2-пиридинилалкильных спиртов в качестве ингибиторов фосфодиэстеразы | |
| JP2017527548A5 (enExample) |