RU2008119412A - N-фенил-фенилацетамидные ненуклеозидные ингибиторы обратной транскриптазы - Google Patents
N-фенил-фенилацетамидные ненуклеозидные ингибиторы обратной транскриптазы Download PDFInfo
- Publication number
- RU2008119412A RU2008119412A RU2008119412/04A RU2008119412A RU2008119412A RU 2008119412 A RU2008119412 A RU 2008119412A RU 2008119412/04 A RU2008119412/04 A RU 2008119412/04A RU 2008119412 A RU2008119412 A RU 2008119412A RU 2008119412 A RU2008119412 A RU 2008119412A
- Authority
- RU
- Russia
- Prior art keywords
- chloro
- fluorophenyl
- alkyl
- cyanophenoxy
- acetylamino
- Prior art date
Links
- 102100034343 Integrase Human genes 0.000 title 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- KYPIASPTMDEDQB-UHFFFAOYSA-N n,2-diphenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)CC1=CC=CC=C1 KYPIASPTMDEDQB-UHFFFAOYSA-N 0.000 title 1
- 239000002777 nucleoside Substances 0.000 title 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 41
- 239000001257 hydrogen Substances 0.000 claims abstract 41
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract 25
- 150000002367 halogens Chemical group 0.000 claims abstract 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 20
- 150000002431 hydrogen Chemical group 0.000 claims abstract 19
- 125000002785 azepinyl group Chemical group 0.000 claims abstract 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 10
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims abstract 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract 8
- 125000003277 amino group Chemical group 0.000 claims abstract 8
- 150000001875 compounds Chemical class 0.000 claims abstract 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 7
- 125000001424 substituent group Chemical group 0.000 claims abstract 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000002252 acyl group Chemical group 0.000 claims abstract 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims abstract 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 3
- -1 3-chloro-5-cyanophenoxy Chemical group 0.000 claims 32
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 7
- WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 6
- 150000003973 alkyl amines Chemical class 0.000 claims 6
- 125000005265 dialkylamine group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- FWKSRNARYZLESF-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-n-[2-(dimethylamino)ethyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCN(C)C)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F FWKSRNARYZLESF-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- JWSUYFINMTWONJ-UHFFFAOYSA-N 2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]-n-[2-methyl-4-(4-methylpiperazine-1-carbonyl)phenyl]acetamide Chemical compound C1CN(C)CCN1C(=O)C(C=C1C)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F JWSUYFINMTWONJ-UHFFFAOYSA-N 0.000 claims 1
- LJKUGMCGHWQIQP-UHFFFAOYSA-N 2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]-n-[2-methyl-4-(morpholine-4-carbonyl)phenyl]acetamide Chemical compound CC1=CC(C(=O)N2CCOCC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Cl)C=1OC1=CC(Cl)=CC(C#N)=C1 LJKUGMCGHWQIQP-UHFFFAOYSA-N 0.000 claims 1
- AHXQUKODDLZYDE-UHFFFAOYSA-N 3-chloro-4-[[2-[3-[3-cyano-5-(difluoromethyl)phenoxy]-2-fluoro-4-methylphenyl]acetyl]amino]benzoic acid Chemical compound FC1=C(OC=2C=C(C=C(C=2)C#N)C(F)F)C(C)=CC=C1CC(=O)NC1=CC=C(C(O)=O)C=C1Cl AHXQUKODDLZYDE-UHFFFAOYSA-N 0.000 claims 1
- ODXOOOKZGQHRGW-UHFFFAOYSA-N 3-chloro-4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]benzoic acid Chemical compound ClC1=CC(C(=O)O)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F ODXOOOKZGQHRGW-UHFFFAOYSA-N 0.000 claims 1
- IYHNSMZJXLICKO-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(1,1-dioxothiolan-3-yl)benzamide Chemical compound C1=CC(Br)=C(OC=2C=C(C=C(Cl)C=2)C#N)C(F)=C1CC(=O)NC(C(=C1)Cl)=CC=C1C(=O)NC1CCS(=O)(=O)C1 IYHNSMZJXLICKO-UHFFFAOYSA-N 0.000 claims 1
- HGVGFSIQUWAMDN-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(1-methylpyrrolidin-3-yl)benzamide Chemical compound C1N(C)CCC1NC(=O)C(C=C1Cl)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F HGVGFSIQUWAMDN-UHFFFAOYSA-N 0.000 claims 1
- FGWYRAMYULKYLU-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(2-methyl-1-pyrrolidin-1-ylpropan-2-yl)benzamide Chemical compound C=1C=C(NC(=O)CC=2C(=C(OC=3C=C(C=C(Cl)C=3)C#N)C(Br)=CC=2)F)C(Cl)=CC=1C(=O)NC(C)(C)CN1CCCC1 FGWYRAMYULKYLU-UHFFFAOYSA-N 0.000 claims 1
- BXRZJJVACKIVHK-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-(2-piperazin-1-ylethyl)benzamide Chemical compound CC1=CC(C(=O)NCCN2CCNCC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Br)C=1OC1=CC(Cl)=CC(C#N)=C1 BXRZJJVACKIVHK-UHFFFAOYSA-N 0.000 claims 1
- DIKPPEZIQIEZDC-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-methylsulfonylbenzamide Chemical compound CC1=CC(C(=O)NS(C)(=O)=O)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F DIKPPEZIQIEZDC-UHFFFAOYSA-N 0.000 claims 1
- IFONNVRVDUVJJH-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-pyrrolidin-3-ylbenzamide Chemical compound CC1=CC(C(=O)NC2CNCC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Br)C=1OC1=CC(Cl)=CC(C#N)=C1 IFONNVRVDUVJJH-UHFFFAOYSA-N 0.000 claims 1
- KGMQXQNBMBWFNE-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F KGMQXQNBMBWFNE-UHFFFAOYSA-N 0.000 claims 1
- AQAWGMJPLXHXLB-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-n-[1-(dimethylamino)propan-2-yl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NC(CN(C)C)C)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F AQAWGMJPLXHXLB-UHFFFAOYSA-N 0.000 claims 1
- WAZLSXHJZGIYEX-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-n-[2-(4-hydroxypiperidin-1-yl)ethyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCN2CCC(O)CC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Br)C=1OC1=CC(Cl)=CC(C#N)=C1 WAZLSXHJZGIYEX-UHFFFAOYSA-N 0.000 claims 1
- KQGTUAXDFAWCSQ-UHFFFAOYSA-N 4-[[2-[4-bromo-3-[3-cyano-5-(difluoromethyl)phenoxy]-2-fluorophenyl]acetyl]amino]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(C=2)C#N)C(F)F)=C1F KQGTUAXDFAWCSQ-UHFFFAOYSA-N 0.000 claims 1
- QJIISZPQAJXSBY-OAHLLOKOSA-N 4-[[2-[4-bromo-3-[3-cyano-5-(difluoromethyl)phenoxy]-2-fluorophenyl]acetyl]amino]-n-[(2r)-2-hydroxypropyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NC[C@H](O)C)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(C=2)C#N)C(F)F)=C1F QJIISZPQAJXSBY-OAHLLOKOSA-N 0.000 claims 1
- CSBUVEGECFMHAY-UHFFFAOYSA-N 4-[[2-[4-bromo-3-[3-cyano-5-(difluoromethyl)phenoxy]-2-fluorophenyl]acetyl]amino]-n-[2-(dimethylamino)ethyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCN(C)C)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(C=2)C#N)C(F)F)=C1F CSBUVEGECFMHAY-UHFFFAOYSA-N 0.000 claims 1
- LRMMFQIFGZUUSR-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-(pyridin-3-ylmethyl)benzamide Chemical compound CC1=CC(C(=O)NCC=2C=NC=CC=2)=CC=C1NC(=O)CC(C=1F)=CC=C(Cl)C=1OC1=CC(Cl)=CC(C#N)=C1 LRMMFQIFGZUUSR-UHFFFAOYSA-N 0.000 claims 1
- JJIREBTYZDYPTP-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-(pyridin-4-ylmethyl)benzamide Chemical compound CC1=CC(C(=O)NCC=2C=CN=CC=2)=CC=C1NC(=O)CC(C=1F)=CC=C(Cl)C=1OC1=CC(Cl)=CC(C#N)=C1 JJIREBTYZDYPTP-UHFFFAOYSA-N 0.000 claims 1
- IFZQHGAHHSYVJZ-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methylbenzamide Chemical compound CC1=CC(C(N)=O)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F IFZQHGAHHSYVJZ-UHFFFAOYSA-N 0.000 claims 1
- UTLYJURUGPEUEO-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F UTLYJURUGPEUEO-UHFFFAOYSA-N 0.000 claims 1
- GVTLGEPQAZGGSS-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-n-(2,3-dihydroxypropyl)-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCC(O)CO)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F GVTLGEPQAZGGSS-UHFFFAOYSA-N 0.000 claims 1
- QYJHMDTVLWIDRQ-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-n-(2-hydroxyethyl)-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCO)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F QYJHMDTVLWIDRQ-UHFFFAOYSA-N 0.000 claims 1
- UGCWNXMAQRWYMD-OAHLLOKOSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-n-[(2r)-2-hydroxypropyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NC[C@H](O)C)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F UGCWNXMAQRWYMD-OAHLLOKOSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- CXJBMLFVFQBYNK-UHFFFAOYSA-N n-(2-amino-2-methylpropyl)-4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chlorobenzamide Chemical compound ClC1=CC(C(=O)NCC(C)(N)C)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F CXJBMLFVFQBYNK-UHFFFAOYSA-N 0.000 claims 1
- NOEUVHHHDKBULJ-UHFFFAOYSA-N n-(2-aminoethyl)-4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCN)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F NOEUVHHHDKBULJ-UHFFFAOYSA-N 0.000 claims 1
- VWTGKVULFGFREA-UHFFFAOYSA-N n-[1-(aminomethyl)cyclopropyl]-4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chlorobenzamide Chemical compound C=1C=C(NC(=O)CC=2C(=C(OC=3C=C(C=C(Cl)C=3)C#N)C(Br)=CC=2)F)C(Cl)=CC=1C(=O)NC1(CN)CC1 VWTGKVULFGFREA-UHFFFAOYSA-N 0.000 claims 1
- ULMJCIRKLJTLMC-UHFFFAOYSA-N n-[2-[bis(2-hydroxyethyl)amino]ethyl]-4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chlorobenzamide Chemical compound ClC1=CC(C(=O)NCCN(CCO)CCO)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F ULMJCIRKLJTLMC-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 229910003827 NRaRb Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- XDPPZYZVSFKCGV-UHFFFAOYSA-N CNN1CCN(C)CC1 Chemical compound CNN1CCN(C)CC1 XDPPZYZVSFKCGV-UHFFFAOYSA-N 0.000 description 1
- JATTWGKYNBEIMH-UHFFFAOYSA-N NCC1(CC1)N Chemical compound NCC1(CC1)N JATTWGKYNBEIMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/29—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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| EP3785714A1 (en) | 2014-04-01 | 2021-03-03 | Merck Sharp & Dohme Corp. | Prodrugs of hiv reverse transcriptase inhibitors |
| EP3760208B1 (en) | 2014-06-25 | 2024-05-29 | The General Hospital Corporation | Targeting human satellite ii (hsatii) |
| EP3166939B1 (en) | 2014-07-07 | 2019-06-05 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| CR20170591A (es) | 2015-05-22 | 2018-05-07 | Genentech Inc | Benzamidas sustituidas y métodos para utilizarlas |
| EP3341353A1 (en) | 2015-08-27 | 2018-07-04 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| PE20181003A1 (es) | 2015-09-28 | 2018-06-26 | Genentech Inc | Compuestos terapeuticos y sus metodos de uso |
| WO2017091592A1 (en) | 2015-11-25 | 2017-06-01 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3436432B1 (en) | 2016-03-30 | 2021-01-27 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| MA46546A (fr) | 2016-10-17 | 2021-05-05 | Genentech Inc | Composés thérapeutiques et leurs procédés d'utilisation |
| EP3601273B1 (en) | 2017-03-24 | 2021-12-01 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
| EP4317972A3 (en) | 2018-02-06 | 2024-03-13 | The General Hospital Corporation | Repeat rna as biomarkers of tumor immune response |
| WO2019165290A1 (en) | 2018-02-26 | 2019-08-29 | Genentech, Inc. | Pyridine-sulfonamide compounds and their use against pain and related conditions |
| CN111936494A (zh) | 2018-03-30 | 2020-11-13 | 豪夫迈·罗氏有限公司 | 作为钠通道抑制剂的取代的氢-吡啶并-吖嗪 |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| WO2020199683A1 (zh) * | 2019-04-04 | 2020-10-08 | 上海海雁医药科技有限公司 | 氮杂环取代的磺酰基苯甲酰胺衍生物、其制法与医药上的用途 |
| CN113698386B (zh) * | 2020-05-22 | 2022-12-27 | 上海美悦生物科技发展有限公司 | 一种4(1h)-吡啶酮类化合物、其药物组合物和用途 |
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| US7166738B2 (en) * | 2004-04-23 | 2007-01-23 | Roche Palo Alto Llc | Non-nucleoside reverse transcriptase inhibitors |
| JP4810529B2 (ja) * | 2004-04-23 | 2011-11-09 | エフ.ホフマン−ラ ロシュ アーゲー | 非ヌクレオシド逆転写酵素インヒビター |
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2006
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- 2006-10-09 DE DE602006005699T patent/DE602006005699D1/de active Active
- 2006-10-09 CN CNA2006800383642A patent/CN101287702A/zh active Pending
- 2006-10-09 AU AU2006303367A patent/AU2006303367A1/en not_active Abandoned
- 2006-10-09 KR KR1020087009224A patent/KR20080047479A/ko not_active Withdrawn
- 2006-10-09 RU RU2008119412/04A patent/RU2008119412A/ru not_active Application Discontinuation
- 2006-10-09 JP JP2008536013A patent/JP2009512659A/ja not_active Ceased
- 2006-10-09 ES ES06807080T patent/ES2320042T3/es active Active
- 2006-10-09 AT AT06807080T patent/ATE425138T1/de active
- 2006-10-09 WO PCT/EP2006/067190 patent/WO2007045572A1/en not_active Ceased
- 2006-10-09 BR BRPI0617482-5A patent/BRPI0617482A2/pt not_active IP Right Cessation
- 2006-10-09 EP EP06807080A patent/EP1940782B1/en not_active Not-in-force
- 2006-10-16 TW TW095137993A patent/TW200800866A/zh unknown
- 2006-10-18 AR ARP060104537A patent/AR057159A1/es unknown
- 2006-10-18 US US11/583,345 patent/US7754919B2/en not_active Expired - Fee Related
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2008
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- 2008-04-10 ZA ZA200803174A patent/ZA200803174B/xx unknown
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| US20070088015A1 (en) | 2007-04-19 |
| CA2625039A1 (en) | 2007-04-26 |
| JP2009512659A (ja) | 2009-03-26 |
| ES2320042T3 (es) | 2009-05-18 |
| BRPI0617482A2 (pt) | 2011-07-26 |
| IL190443A0 (en) | 2008-11-03 |
| KR20080047479A (ko) | 2008-05-28 |
| TW200800866A (en) | 2008-01-01 |
| US7754919B2 (en) | 2010-07-13 |
| AR057159A1 (es) | 2007-11-21 |
| CN101287702A (zh) | 2008-10-15 |
| ATE425138T1 (de) | 2009-03-15 |
| DE602006005699D1 (de) | 2009-04-23 |
| ZA200803174B (en) | 2009-03-25 |
| EP1940782B1 (en) | 2009-03-11 |
| EP1940782A1 (en) | 2008-07-09 |
| WO2007045572A1 (en) | 2007-04-26 |
| AU2006303367A1 (en) | 2007-04-26 |
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