RU2015137295A - Противовирусные соединения - Google Patents
Противовирусные соединения Download PDFInfo
- Publication number
- RU2015137295A RU2015137295A RU2015137295A RU2015137295A RU2015137295A RU 2015137295 A RU2015137295 A RU 2015137295A RU 2015137295 A RU2015137295 A RU 2015137295A RU 2015137295 A RU2015137295 A RU 2015137295A RU 2015137295 A RU2015137295 A RU 2015137295A
- Authority
- RU
- Russia
- Prior art keywords
- phenyl
- diamine
- pyridin
- dichloro
- triazole
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 16
- 230000000840 anti-viral effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 241000711549 Hepacivirus C Species 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- -1 2,6-diaza-spiro [3.3] heptanyl Chemical group 0.000 claims 4
- 239000003443 antiviral agent Substances 0.000 claims 3
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims 3
- 210000000987 immune system Anatomy 0.000 claims 3
- UGLWXDYLLILNED-UHFFFAOYSA-N 3-(3-chloro-4-pyridazin-3-ylphenyl)-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=CC=1C=1N=NC=CC=1)C1(NNC(=N1)N)N UGLWXDYLLILNED-UHFFFAOYSA-N 0.000 claims 2
- 102000014150 Interferons Human genes 0.000 claims 2
- 108010050904 Interferons Proteins 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 229940079322 interferon Drugs 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 230000010076 replication Effects 0.000 claims 2
- YCFCCZXYLSSMIN-UHFFFAOYSA-N 1-[3-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2,6-dichlorophenyl]thiophen-2-yl]ethanone Chemical compound S1C=CC(C=2C(=CC(NC=3N=C(N)NN=3)=CC=2Cl)Cl)=C1C(=O)C YCFCCZXYLSSMIN-UHFFFAOYSA-N 0.000 claims 1
- QPQIHFGZTYMHQB-UHFFFAOYSA-N 1-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2,6-dichlorophenyl]pyridin-2-one Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)N2C(C=CC=C2)=O)=N1 QPQIHFGZTYMHQB-UHFFFAOYSA-N 0.000 claims 1
- AYWOHARGWPLPMB-UHFFFAOYSA-N 1-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2-chlorophenyl]pyridin-2-one Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=CC=2)N2C(C=CC=C2)=O)=N1 AYWOHARGWPLPMB-UHFFFAOYSA-N 0.000 claims 1
- OQGVFXCKOKZYGU-UHFFFAOYSA-N 3-(3,5-dichloro-4-pyrazol-1-ylphenyl)-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=C(C=1N1N=CC=C1)Cl)C1(NNC(=N1)N)N OQGVFXCKOKZYGU-UHFFFAOYSA-N 0.000 claims 1
- UJQOYZPXZQGEEA-UHFFFAOYSA-N 3-(3,5-dichloro-4-pyridazin-4-ylphenyl)-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=C(C=1C1=CN=NC=C1)Cl)C1(NNC(=N1)N)N UJQOYZPXZQGEEA-UHFFFAOYSA-N 0.000 claims 1
- YYDITELXOKPJEO-UHFFFAOYSA-N 3-[3,5-dichloro-4-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=C(C=1C=1CCNCC=1)Cl)C1(NNC(=N1)N)N YYDITELXOKPJEO-UHFFFAOYSA-N 0.000 claims 1
- QJBUDCLKYAPCFX-UHFFFAOYSA-N 3-[3,5-dichloro-4-(5-methylsulfonylpyridin-3-yl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=C(C=1C=1C=NC=C(C=1)S(=O)(=O)C)Cl)C1(NNC(=N1)N)N QJBUDCLKYAPCFX-UHFFFAOYSA-N 0.000 claims 1
- UWDQIVBKAULEKH-UHFFFAOYSA-N 3-[3,5-dichloro-4-(6-methoxypyridin-3-yl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound C1=NC(OC)=CC=C1C1=C(Cl)C=C(C2(N)N=C(N)NN2)C=C1Cl UWDQIVBKAULEKH-UHFFFAOYSA-N 0.000 claims 1
- AKTUWGRSJQEXAA-UHFFFAOYSA-N 3-[3,5-dichloro-4-(6-methylsulfonylpyridin-3-yl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=C(C=1C=1C=NC(=CC=1)S(=O)(=O)C)Cl)C1(NNC(=N1)N)N AKTUWGRSJQEXAA-UHFFFAOYSA-N 0.000 claims 1
- IJIYUSMQXJMUNY-UHFFFAOYSA-N 3-[3,5-dichloro-4-([1,2,4]triazolo[4,3-a]pyridin-3-yl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound N1NC(N)=NC1(N)C(C=C1Cl)=CC(Cl)=C1C1=NN=C2N1C=CC=C2 IJIYUSMQXJMUNY-UHFFFAOYSA-N 0.000 claims 1
- AXXVQNZWKKSRHS-UHFFFAOYSA-N 3-[3-chloro-4-(1,2,3,6-tetrahydropyridin-4-yl)-5-(trifluoromethyl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=C(C=1C=1CCNCC=1)C(F)(F)F)C1(NNC(=N1)N)N AXXVQNZWKKSRHS-UHFFFAOYSA-N 0.000 claims 1
- VDLBMKDWBRBJPW-UHFFFAOYSA-N 3-[3-chloro-4-(1-methyltetrazol-5-yl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=CC=1C1=NN=NN1C)C1(NNC(=N1)N)N VDLBMKDWBRBJPW-UHFFFAOYSA-N 0.000 claims 1
- FVXKSODDYOLMGG-UHFFFAOYSA-N 3-[3-chloro-4-(2-methyl-1,2,4-triazol-3-yl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound ClC=1C=C(C=CC=1C=1N(N=CN=1)C)C1(NNC(=N1)N)N FVXKSODDYOLMGG-UHFFFAOYSA-N 0.000 claims 1
- ILTHDEGCCUOOHO-UHFFFAOYSA-N 3-[3-fluoro-4-(6-fluoropyridin-3-yl)-5-(trifluoromethyl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound FC=1C=C(C=C(C=1C=1C=NC(=CC=1)F)C(F)(F)F)C1(N=C(NN1)N)N ILTHDEGCCUOOHO-UHFFFAOYSA-N 0.000 claims 1
- ZGKLJLIROOEKRC-UHFFFAOYSA-N 3-[3-fluoro-4-pyridin-3-yl-5-(trifluoromethyl)phenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound FC=1C=C(C=C(C=1C=1C=NC=CC=1)C(F)(F)F)C1(N=C(NN1)N)N ZGKLJLIROOEKRC-UHFFFAOYSA-N 0.000 claims 1
- FKVAICYUIZNMCQ-UHFFFAOYSA-N 3-[4-(2-aminopyrimidin-5-yl)-3,5-dichlorophenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound NC1=NC=C(C=N1)C1=C(C=C(C=C1Cl)C1(NNC(=N1)N)N)Cl FKVAICYUIZNMCQ-UHFFFAOYSA-N 0.000 claims 1
- UBGWGHQINPVZNF-UHFFFAOYSA-N 3-[4-(6-aminopyridin-3-yl)-3,5-dichlorophenyl]-1,2-dihydro-1,2,4-triazole-3,5-diamine Chemical compound N1NC(N)=NC1(N)C1=CC(Cl)=C(C=2C=NC(N)=CC=2)C(Cl)=C1 UBGWGHQINPVZNF-UHFFFAOYSA-N 0.000 claims 1
- MEJZEXWHTVRNAY-UHFFFAOYSA-N 3-n-(3,5-dichloro-4-pyridin-3-ylphenyl)-1h-1,2,4-triazole-3,5-diamine Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)C=2C=NC=CC=2)=N1 MEJZEXWHTVRNAY-UHFFFAOYSA-N 0.000 claims 1
- PAPMFDRSNHIDTN-UHFFFAOYSA-N 3-n-(3,5-dichloro-4-pyridin-4-ylphenyl)-1h-1,2,4-triazole-3,5-diamine Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)C=2C=CN=CC=2)=N1 PAPMFDRSNHIDTN-UHFFFAOYSA-N 0.000 claims 1
- BPPQWLXVMPRHJM-UHFFFAOYSA-N 3-n-(3,5-dichloro-4-pyrimidin-5-ylphenyl)-1h-1,2,4-triazole-3,5-diamine Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)C=2C=NC=NC=2)=N1 BPPQWLXVMPRHJM-UHFFFAOYSA-N 0.000 claims 1
- IOFRZQDWILLDPH-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-(1h-pyrazol-5-yl)phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(C=3NN=CC=3)=C(Cl)C=2)=N1 IOFRZQDWILLDPH-UHFFFAOYSA-N 0.000 claims 1
- RDGLLXCZWKMHKE-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-(2-methoxypyridin-4-yl)phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound C1=NC(OC)=CC(C=2C(=CC(NC=3N=C(N)NN=3)=CC=2Cl)Cl)=C1 RDGLLXCZWKMHKE-UHFFFAOYSA-N 0.000 claims 1
- KGYOKCODXTYQJW-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-(2-methoxypyrimidin-5-yl)phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound C1=NC(OC)=NC=C1C(C(=C1)Cl)=C(Cl)C=C1NC1=NNC(N)=N1 KGYOKCODXTYQJW-UHFFFAOYSA-N 0.000 claims 1
- CIMNEGJYBDOQBF-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-(5-chloropyridin-3-yl)phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)C=2C=C(Cl)C=NC=2)=N1 CIMNEGJYBDOQBF-UHFFFAOYSA-N 0.000 claims 1
- FECCOQQSQPEJLS-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-(5-chlorothiophen-2-yl)phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(C=3SC(Cl)=CC=3)=C(Cl)C=2)=N1 FECCOQQSQPEJLS-UHFFFAOYSA-N 0.000 claims 1
- MEPPBGXMWHBXHX-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-(6-methoxypyridin-2-yl)phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound COC1=CC=CC(C=2C(=CC(NC=3N=C(N)NN=3)=CC=2Cl)Cl)=N1 MEPPBGXMWHBXHX-UHFFFAOYSA-N 0.000 claims 1
- MFNCZGDPVPSPMB-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-[1-methyl-3-(trifluoromethyl)pyrazol-4-yl]phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound FC(F)(F)C1=NN(C)C=C1C(C(=C1)Cl)=C(Cl)C=C1NC1=NNC(N)=N1 MFNCZGDPVPSPMB-UHFFFAOYSA-N 0.000 claims 1
- JIFIJSMEAJQPSA-UHFFFAOYSA-N 3-n-[3,5-dichloro-4-[6-(trifluoromethyl)pyridin-3-yl]phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)C=2C=NC(=CC=2)C(F)(F)F)=N1 JIFIJSMEAJQPSA-UHFFFAOYSA-N 0.000 claims 1
- MKUYZXAJRQRWBM-UHFFFAOYSA-N 3-n-[3-chloro-4-(6-propan-2-ylsulfonylpyridin-3-yl)-5-(trifluoromethyl)phenyl]-1h-1,2,4-triazole-3,5-diamine Chemical compound C1=NC(S(=O)(=O)C(C)C)=CC=C1C(C(=C1)C(F)(F)F)=C(Cl)C=C1NC1=NNC(N)=N1 MKUYZXAJRQRWBM-UHFFFAOYSA-N 0.000 claims 1
- YNKDSOVOILOXEO-UHFFFAOYSA-N 4-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2,6-dichlorophenyl]-1h-pyridin-2-one Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)C2=CC(=O)NC=C2)=N1 YNKDSOVOILOXEO-UHFFFAOYSA-N 0.000 claims 1
- BMDCFJPNGPRJEC-UHFFFAOYSA-N 4-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2,6-dichlorophenyl]-3,6-dihydro-2h-pyridine-1-carboxylic acid Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(C=3CCN(CC=3)C(O)=O)=C(Cl)C=2)=N1 BMDCFJPNGPRJEC-UHFFFAOYSA-N 0.000 claims 1
- FVAIVWPCQSMRNO-UHFFFAOYSA-N 5-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2,6-dichlorophenyl]-1h-pyridin-2-one Chemical compound N1C(N)=NC(NC=2C=C(Cl)C(=C(Cl)C=2)C2=CNC(=O)C=C2)=N1 FVAIVWPCQSMRNO-UHFFFAOYSA-N 0.000 claims 1
- FVYBHSULJHBHNY-UHFFFAOYSA-N 5-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2-chloro-6-(trifluoromethyl)phenyl]-n-(1,1,1-trifluoro-2-methylpropan-2-yl)pyridine-2-sulfonamide Chemical compound C1=NC(S(=O)(=O)NC(C)(C)C(F)(F)F)=CC=C1C(C(=C1)C(F)(F)F)=C(Cl)C=C1NC1=NNC(N)=N1 FVYBHSULJHBHNY-UHFFFAOYSA-N 0.000 claims 1
- SSQYGELCNBBBDQ-UHFFFAOYSA-N 5-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2-chloro-6-(trifluoromethyl)phenyl]-n-methylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)NC)=CC=C1C(C(=C1)C(F)(F)F)=C(Cl)C=C1NC1=NNC(N)=N1 SSQYGELCNBBBDQ-UHFFFAOYSA-N 0.000 claims 1
- IEXBIMUFTKNJHA-UHFFFAOYSA-N 5-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2-chloro-6-(trifluoromethyl)phenyl]-n-tert-butylpyridine-2-sulfonamide Chemical compound C1=NC(S(=O)(=O)NC(C)(C)C)=CC=C1C(C(=C1)C(F)(F)F)=C(Cl)C=C1NC1=NNC(N)=N1 IEXBIMUFTKNJHA-UHFFFAOYSA-N 0.000 claims 1
- ZGBIVQUGKYHQOT-UHFFFAOYSA-N ClC1=C(C(=CC(=C1)C1(NNC(=N1)N)N)C(F)(F)F)C1=CC=C(C=C1)N1CCN(CC1)C Chemical compound ClC1=C(C(=CC(=C1)C1(NNC(=N1)N)N)C(F)(F)F)C1=CC=C(C=C1)N1CCN(CC1)C ZGBIVQUGKYHQOT-UHFFFAOYSA-N 0.000 claims 1
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims 1
- 229940122604 HCV protease inhibitor Drugs 0.000 claims 1
- 229940121759 Helicase inhibitor Drugs 0.000 claims 1
- 101800001014 Non-structural protein 5A Proteins 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- HFRLJTFPQYNCPF-UHFFFAOYSA-N n-(1-adamantyl)-5-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2-chloro-6-(trifluoromethyl)phenyl]pyridine-2-sulfonamide Chemical compound N1C(N)=NC(NC=2C=C(C(C=3C=NC(=CC=3)S(=O)(=O)NC34CC5CC(CC(C5)C3)C4)=C(Cl)C=2)C(F)(F)F)=N1 HFRLJTFPQYNCPF-UHFFFAOYSA-N 0.000 claims 1
- KERUGSYEKGDVFN-UHFFFAOYSA-N n-[5-[4-[(5-amino-1h-1,2,4-triazol-3-yl)amino]-2,6-dichlorophenyl]pyridin-2-yl]methanesulfonamide Chemical compound C1=NC(NS(=O)(=O)C)=CC=C1C(C(=C1)Cl)=C(Cl)C=C1NC1=NNC(N)=N1 KERUGSYEKGDVFN-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient 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
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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Claims (71)
1. Соединение формулы I
A представляет собой ненасыщенный или частично ненасыщенный моноциклический или бициклический гетероарил или моноциклический или спироциклический гетероциклоалкил;
каждый R1 независимо представляет собой галоген, галоген низший алкил, или низший алкилсульфонил;
m представляет собой 0, 1, или 2;
каждый R2 независимо представляет собой галоген, низший алкокси, оксо, амино, низший алкил, C(=O)OR2', S(=O)2R2', S(=O)2NHR2', гидроксил низший алкил, C(=O)NHR2', или C(=O)R2';
n представляет собой 0, 1, или 2; и
R2' представляет собой низший алкил, галоген низший алкил, или адамантил;
или его фармацевтически приемлемая соль.
2. Соединение по п. 1, где m представляет собой 1.
3. Соединение по п. 2, где m представляет собой 2.
4. Соединение по п. 3, где один R1 представляет собой галоген, а другой представляет собой галоген низший алкил;
5. Соединение по п. 3, где оба R1 представляют собой галоген.
6. Соединение по любому из пп. 1-5, где n представляет собой 0.
7. Соединение по любому из пп. 1-5, где n представляет собой 1.
8. Соединение по любому из пп. 1-5, где n представляет собой 2.
9. Соединение по любому из пп. 1-5, где А представляет собой пиридинил, пиримидинил, пиридазинил, триазолил, тетразолил, пиперазинил, 2,6-диаза-спиро[3.3]гептанил, азетидинил, тиофенил или пиразолил.
10. Соединение по п. 9, где R2 представляет собой галоген, низший алкокси, оксо, амино, низший алкил, C(=O)OR2', S(=O)2R2', S(=O)2NHR2', гидроксил низший алкил, C(=O)NHR2', или C(=O)R2'.
11. Соединение по п. 10, где R2' представляет собой низший алкил или галоген низший алкил.
12. Соединение, выбранное из группы, состоящей из:
N3-[3,5-дихлор-4-(6-метокси-пиридин-3-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(5-метансульфонил-пиридин-3-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
5-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2,6-дихлор-фенил]-1Н-пиридин-2-он;
N3-[4-(6-амино-пиридин-3-ил)-3,5-дихлор-фенил]-1H-[1,2,4]триазол-3,5-диамин;
N3-[4-(2-амино-пиримидин-5-ил)-3,5-дихлор-фенил]-1H-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(2-метокси-пиридин-4-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
4-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2,6-дихлор-фенил]-1Н-пиридин-2-он;
N-{5-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2,6-дихлор-фенил]-пиридин-2-ил}-метансульфонамид;
N5-[3-фтор-4-(6-фтор-пиридин-3-ил)-5-трифторметил-фенил]-1H-[1,2,4]триазол-3,5-диамин;
N5-(3-фтор-4-пиридин-3-ил-5-трифторметил-фенил)-1Н-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(6-метансульфонил-пиридин-3-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
6-[4-(5-амино-1H-[1,2,4]триазол-3-иламино)-2,6-дихлор-фенил]-2,6-диаза-спиро[3.3]гептан-2-карбоновой кислоты трет-бутиловый эфир;
N3-(3-хлор-4-пиридазин-3-ил-фенил)-1Н-[1,2,4]-триазол-3,5-диамин;
N3-[3-хлор-4-(1-метил-1H-тетразол-5-ил)-фенил]-1H-[1,2,4]триазол-3,5-диамин;
N3-[3-хлор-4-(2-метил-2Н-[1,2,4]триазол-3-ил)-фенил]-1H-[1,2,4]триазол-3,5-диамин;
N3-(3,5-дихлор-4-пиразол-1-ил-фенил)-1Н-[1,2,4]триазол-3,5-диамин;
4-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2,6-дихлор-фенил]-3,6-дигидро-2Н-пиридин-1-карбоновой кислоты трет-бутиловый эфир;
N3-[3,5-дихлор-4-(1,2,3,6-тетрагидро-пиридин-4-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
4-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2-хлор-6-трифторметил-фенил]-3,6-дигидро-2H-пиридин-1-карбоновой кислоты трет-бутиловый эфир;
N3-[3-хлор-4-(1,2,3,6-тетрагидро-пиридин-4-ил)-5-трифторметил-фенил]-1H-[1,2,4]триазол-3,5-диамин;
N5-(3,5-дихлор-4-[1,2,4]триазоло[4,3-а]пиридин-3-ил-фенил)-1Н-[1,2,4]триазол-3,5-диамин;
N-{3-хлор-4-[6-(пропан-2-сульфонил)-пиридин-3-ил]-5-трифторметил-фенил}-4Н-[1,2,4]триазол-3,5-диамин;
5-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2-хлор-6-трифторметил-фенил]-пиридин-2-сульфоновой кислоты трет-бутиламид;
5-[4-(5-амино-1H-[1,2,4]триазол-3-иламино)-2-хлор-6-трифторметил-фенил]-пиридин-2-сульфоновой кислоты (2,2,2-трифтор-1,1-диметил-этил)-амид;
5-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2-хлор-6-трифторметил-фенил]-пиридин-2-сульфоновой кислоты адамантан-1-иламид;
N3-[2-хлор-4'-(4-метил-пиперазин-1-ил)-6-трифторметил-бифенил-4-ил]-1Н-[1,2,4]триазол-3,5-диамин;
N3-(3-хлор-4-пиридазин-3-ил-фенил)-1H-[1,2,4]триазол-3,5-диамин;
1-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-фенил]-1H-пиридин-2-он;
1-[4-(5-амино-1H-[1,2,4]триазол-3-иламино)-2-хлор-фенил]-1Н-пиридин-2-он;
1-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2,6-дихлор-фенил]-1Н-пиридин-2-он;
5-[4-(5-амино-1H-[1,2,4]триазол-3-иламино)-2-хлор-6-трифторметил-фенил]-пиридин-2-карбоновой кислоты метиламид;
N3-(3,5-дихлор-4-пиридазин-4-ил-фенил)-1H-[1,2,4]триазол-3,5-диамин;
1-{3-[4-(5-амино-1Н-[1,2,4]триазол-3-иламино)-2,6-дихлор-фенил]-тиофен-2-ил}-этанон;
N3-(3,5-дихлор-4-пиридин-4-ил-фенил)-1Н-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(5-хлор-тиофен-2-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
N3-(3,5-дихлор-4-пиридин-3-ил-фенил)-1Н-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(1Н-пиразол-3-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
N3-(3,5-дихлор-4-пиримидин-5-ил-фенил)-1Н-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(2-метокси-пиримидин-5-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(6-трифторметил-пиридин-3-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(1-метил-3-трифторметил-1Н-пиразол-4-ил)-фенил]-1H-[1,2,4]триазол-3,5-диамин;
N3-[3,5-дихлор-4-(5-хлор-пиридин-3-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин; и
N3-[3,5-дихлор-4-(6-метокси-пиридин-2-ил)-фенил]-1Н-[1,2,4]триазол-3,5-диамин.
13. Способ предотвращения инфекции вируса гепатита С (ВГС), содержащий введение нуждающемуся в этом пациенту терапевтически эффективного количества соединения по любому из пп. 1-12.
14. Способ по п. 13, дополнительно включающий введение нуждающемуся в этом пациенту терапевтически эффективного количества супрессора иммунной системы.
15. Способ лечения инфекции вируса гепатита С (ВГС), содержащий введение нуждающемуся в этом пациенту терапевтически эффективного количества соединения по любому из пп. 1-12.
16. Способ по любому из пп. 13-15, дополнительно включающий введение комбинации противовирусных агентов, которые ингибируют репликацию ВГС.
17. Способ по любому из пп. 13-15, дополнительно включающий введение модулятора иммунной системы или противовирусного агента, который ингибирует репликацию ВГС, или их комбинации.
18. Способ по п. 17, где модулятор иммунной системы представляет собой интерферон или химически дериватизированный интерферон.
19. Способ по п. 17, где противовирусный агент выбран из группы, состоящей из ингибитора протеазы ВГС, ингибитора полимеразы ВГС, ингибитора геликазы ВГС, ингибитора NS5A ВГС, или любой их комбинации.
20. Композиция, содержащая соединение по любому из пп. 1-12 и фармацевтически приемлемый эксципиент.
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