JP2009512659A5 - - Google Patents
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- JP2009512659A5 JP2009512659A5 JP2008536013A JP2008536013A JP2009512659A5 JP 2009512659 A5 JP2009512659 A5 JP 2009512659A5 JP 2008536013 A JP2008536013 A JP 2008536013A JP 2008536013 A JP2008536013 A JP 2008536013A JP 2009512659 A5 JP2009512659 A5 JP 2009512659A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phenyl
- cyano
- fluoro
- phenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- RQDQSDYSBAGZGU-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(3-methyl-1,1-dioxothiolan-3-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)NC1(C)CCS(=O)(=O)C1 RQDQSDYSBAGZGU-UHFFFAOYSA-N 0.000 claims description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 36
- -1 hydroxy, amino Chemical group 0.000 claims 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000002785 azepinyl group Chemical group 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 6
- 150000003973 alkyl amines Chemical class 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000005265 dialkylamine group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 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 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000006513 pyridinyl methyl group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- RMPXXFRHIOIRGV-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(diaminomethylidene)benzamide Chemical compound ClC1=CC(C(=O)NC(=N)N)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F RMPXXFRHIOIRGV-UHFFFAOYSA-N 0.000 claims 2
- 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
- 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- JGCGUYNAWQANJG-UHFFFAOYSA-N 2-(1,3-dihydroxy-2-methylpropan-2-yl)benzamide Chemical compound OCC(CO)(C)C1=C(C(=O)N)C=CC=C1 JGCGUYNAWQANJG-UHFFFAOYSA-N 0.000 claims 1
- 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
- YISHQLWVTOMFOV-UHFFFAOYSA-N 2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]-n-[4-(4-hydroxypiperidine-1-carbonyl)-2-methylphenyl]acetamide Chemical compound CC1=CC(C(=O)N2CCC(O)CC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Cl)C=1OC1=CC(Cl)=CC(C#N)=C1 YISHQLWVTOMFOV-UHFFFAOYSA-N 0.000 claims 1
- LJRYOEDYFVSOLG-HXUWFJFHSA-N 2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]-n-[4-[(3r)-3-hydroxypyrrolidine-1-carbonyl]-2-methylphenyl]acetamide Chemical compound CC1=CC(C(=O)N2C[C@H](O)CC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Cl)C=1OC1=CC(Cl)=CC(C#N)=C1 LJRYOEDYFVSOLG-HXUWFJFHSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 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
- 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
- KPRJCSDJLSXYFZ-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(1,4-dimethylpiperidin-4-yl)benzamide Chemical compound C1CN(C)CCC1(C)NC(=O)C(C=C1Cl)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F KPRJCSDJLSXYFZ-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
- JOYLOSWKXNBUKR-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(2-methylsulfonylethyl)benzamide Chemical compound ClC1=CC(C(=O)NCCS(=O)(=O)C)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F JOYLOSWKXNBUKR-UHFFFAOYSA-N 0.000 claims 1
- ZNZUKLODROUGGJ-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(2-pyrrolidin-1-ylethyl)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)NCCN1CCCC1 ZNZUKLODROUGGJ-UHFFFAOYSA-N 0.000 claims 1
- WYFSKQARXVUBQG-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(4-methylpiperidin-4-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)NC1(C)CCNCC1 WYFSKQARXVUBQG-UHFFFAOYSA-N 0.000 claims 1
- HGCJTYQEUFHSOR-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-(n'-methylcarbamimidoyl)benzamide Chemical compound ClC1=CC(C(=O)NC(N)=NC)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F HGCJTYQEUFHSOR-UHFFFAOYSA-N 0.000 claims 1
- OAUDFQBSLLMVCI-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-[(1-ethylpyrrolidin-2-yl)methyl]benzamide Chemical compound CCN1CCCC1CNC(=O)C(C=C1Cl)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F OAUDFQBSLLMVCI-UHFFFAOYSA-N 0.000 claims 1
- UWRKBBBSADBXMO-FGZHOGPDSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-[(3s,4s)-4-hydroxy-1,1-dioxothiolan-3-yl]benzamide Chemical compound O[C@@H]1CS(=O)(=O)C[C@H]1NC(=O)C(C=C1Cl)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F UWRKBBBSADBXMO-FGZHOGPDSA-N 0.000 claims 1
- VFNLGWUACZBEOT-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-[1-(dimethylamino)propan-2-yl]benzamide Chemical compound ClC1=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 VFNLGWUACZBEOT-UHFFFAOYSA-N 0.000 claims 1
- ASJZRQSCGKKMMN-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-[2-(4,4-difluoropiperidin-1-yl)ethyl]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)NCCN1CCC(F)(F)CC1 ASJZRQSCGKKMMN-UHFFFAOYSA-N 0.000 claims 1
- SRFPJVOVJJGJDL-QNSVNVJESA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chloro-n-[2-[(2r)-2,5-dimethylpyrrolidin-1-yl]ethyl]benzamide Chemical compound CC1CC[C@@H](C)N1CCNC(=O)C(C=C1Cl)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F SRFPJVOVJJGJDL-QNSVNVJESA-N 0.000 claims 1
- DNSWUGJQRPDPJH-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-(2-morpholin-4-ylethyl)benzamide Chemical compound CC1=CC(C(=O)NCCN2CCOCC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Br)C=1OC1=CC(Cl)=CC(C#N)=C1 DNSWUGJQRPDPJH-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
- MASSJKAKYABTOI-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(C(=O)NCCN2CCCC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Br)C=1OC1=CC(Cl)=CC(C#N)=C1 MASSJKAKYABTOI-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
- PBTCZMZTLWPPTH-UHFFFAOYSA-N 4-[[2-[4-bromo-3-[3-cyano-5-(difluoromethyl)phenoxy]-2-fluorophenyl]acetyl]amino]-3-chloro-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound N#CC1=CC(C(F)F)=CC(OC=2C(=C(CC(=O)NC=3C(=CC(=CC=3)C(=O)NCCN3CCCC3)Cl)C=CC=2Br)F)=C1 PBTCZMZTLWPPTH-UHFFFAOYSA-N 0.000 claims 1
- HZOZQCMRZGNUPW-UHFFFAOYSA-N 4-[[2-[4-bromo-3-[3-cyano-5-(difluoromethyl)phenoxy]-2-fluorophenyl]acetyl]amino]-3-methyl-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(C(=O)NCCN2CCCC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Br)C=1OC1=CC(C#N)=CC(C(F)F)=C1 HZOZQCMRZGNUPW-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
- HKZOTSCKSDUKTA-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CC1=CC(C(=O)NCCN2CCCC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Cl)C=1OC1=CC(Cl)=CC(C#N)=C1 HKZOTSCKSDUKTA-UHFFFAOYSA-N 0.000 claims 1
- UHANODMRILXMMZ-UHFFFAOYSA-N 4-[[2-[4-chloro-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-methyl-n-(4-methylpiperazin-1-yl)benzamide Chemical compound C1CN(C)CCN1NC(=O)C(C=C1C)=CC=C1NC(=O)CC1=CC=C(Cl)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F UHANODMRILXMMZ-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
- 208000030507 AIDS Diseases 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 1
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| US8933236B2 (en) | 2012-05-22 | 2015-01-13 | Xenon Pharmaceuticals Inc. | N-substituted benzamides and methods of use thereof |
| DK2826770T3 (en) * | 2005-06-24 | 2019-01-07 | Biotron Ltd | Acylguanidine compounds with antiviral activity |
| JP5135336B2 (ja) | 2006-05-31 | 2013-02-06 | ダウ グローバル テクノロジーズ エルエルシー | 熱可塑性ポリマー系を選択的に加熱するためのマイクロ波エネルギーの使用 |
| CL2007002105A1 (es) * | 2006-07-21 | 2008-02-22 | Hoffmann La Roche | Compuestos derivados de 2-[3-(3-cianofenoxi)(fenoxi o fenilsulfanil)]-n-fenil acetamida, inhibidores de la transcriptasa inversa del vih; procedimiento de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar u |
| CN101501002B (zh) * | 2006-08-16 | 2012-06-27 | 弗·哈夫曼-拉罗切有限公司 | 非核苷逆转录酶抑制剂 |
| CA2687747C (en) * | 2007-05-30 | 2015-11-17 | F. Hoffmann-La Roche Ag | Non-nucleoside reverse transcriptase inhibitors |
| WO2009000663A1 (en) * | 2007-06-22 | 2008-12-31 | F. Hoffmann-La Roche Ag | Urea and carbamate derivatives as non-nucleoside reverse transcriptase inhibitors |
| RU2010125220A (ru) | 2007-11-20 | 2011-12-27 | Мерк Шарп Энд Домэ Корп. (Us) | Ненуклеозидные ингибиторы обратной транскриптазы |
| BRPI0821349A2 (pt) * | 2007-12-21 | 2019-09-24 | Hoffmann La Roche | compostos antivirais heterocíclicos |
| WO2010114907A1 (en) | 2009-03-31 | 2010-10-07 | Vanderbilt University | Sulfonyl-azetidin-3-yl-methylamine amide analogs as glyt1 inhibitors, methods for making same, and use of same in treating psychiatric disorders |
| DK2924034T3 (en) | 2010-03-30 | 2017-02-06 | Merck Canada Inc | PHARMACEUTICAL COMPOSITION CONTAINING A NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR |
| CN103517990A (zh) | 2010-10-07 | 2014-01-15 | 通用医疗公司 | 癌症生物标志物 |
| CN102219717A (zh) * | 2011-04-20 | 2011-10-19 | 复旦大学 | N-苯基芳基甲酰胺衍生物及其制备方法和用途 |
| CN102206177A (zh) * | 2011-04-20 | 2011-10-05 | 复旦大学 | 1-萘基苯甲酮衍生物及其制备方法和用途 |
| JP6014154B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ベンゼンスルホンアミド化合物および治療剤としてのそれらの使用 |
| WO2013064984A1 (en) | 2011-10-31 | 2013-05-10 | Xenon Pharmaceuticals Inc. | Biaryl ether sulfonamides and their use as therapeutic agents |
| BR112015000187A2 (pt) | 2012-07-06 | 2017-06-27 | Genentech Inc | benzamidas substituídas com n e métodos de uso das mesmas |
| JO3470B1 (ar) | 2012-10-08 | 2020-07-05 | Merck Sharp & Dohme | مشتقات 5- فينوكسي-3h-بيريميدين-4-أون واستخدامها كمثبطات ناسخ عكسي ل hiv |
| TWI598325B (zh) | 2012-10-12 | 2017-09-11 | Ｈ 朗德貝克公司 | 苯甲醯胺類 |
| TW201427947A (zh) | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
| WO2014082879A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4]triazole compounds |
| WO2014082880A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4] triazole compounds |
| WO2014082881A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| EP2925730A1 (en) | 2012-11-27 | 2015-10-07 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| DK3219707T3 (da) | 2013-01-09 | 2019-09-23 | Basf Agro Bv | Fremgangsmåde til fremstilling af substituerede oxiraner og triazoler |
| KR20150131233A (ko) | 2013-03-14 | 2015-11-24 | 제넨테크, 인크. | 치환된 트리아졸로피리딘 및 이의 사용 방법 |
| US9493429B2 (en) | 2013-03-15 | 2016-11-15 | Genentech, Inc. | Substituted benzoxazoles and methods of use thereof |
| WO2015077273A1 (en) * | 2013-11-22 | 2015-05-28 | Merck Sharp & Dohme Corp. | Composition of a non-nucleoside reverse transcriptase inhibitor |
| CR20160296A (es) | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| CA2944187C (en) | 2014-04-01 | 2018-06-19 | Merck Sharp & Dohme Corp. | Prodrugs of hiv reverse transcriptase inhibitors |
| US10301624B2 (en) | 2014-06-25 | 2019-05-28 | The General Hospital Corporation | Targeting human satellite II (HSATII) |
| WO2016007534A1 (en) | 2014-07-07 | 2016-01-14 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| EP3297989A1 (en) | 2015-05-22 | 2018-03-28 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| CN108137477A (zh) | 2015-08-27 | 2018-06-08 | 基因泰克公司 | 治疗化合物及其使用方法 |
| CN108290881B (zh) | 2015-09-28 | 2021-12-07 | 健泰科生物技术公司 | 治疗性化合物和其使用方法 |
| EP3380466A1 (en) | 2015-11-25 | 2018-10-03 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| US10766858B2 (en) | 2016-03-30 | 2020-09-08 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| MX388175B (es) | 2016-10-17 | 2025-03-19 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| EP3601273B1 (en) | 2017-03-24 | 2021-12-01 | Genentech, Inc. | 4-piperidin-n-(pyrimidin-4-yl)chroman-7-sulfonamide derivatives as sodium channel inhibitors |
| CN112533613A (zh) | 2018-02-06 | 2021-03-19 | 通用医疗公司 | 作为肿瘤免疫应答的生物标志物的重复rna |
| CN112041313A (zh) | 2018-02-26 | 2020-12-04 | 基因泰克公司 | 吡啶-磺酰胺化合物及其针对疼痛和相关疾患的用途 |
| JP2021519788A (ja) | 2018-03-30 | 2021-08-12 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ナトリウムチャネル阻害剤としての縮合環ヒドロピリド化合物 |
| 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 |
| ES2333802T3 (es) * | 2004-04-23 | 2010-03-01 | F. Hoffmann-La Roche Ag | Inhibidores no nucleicos de transcriptasa inversa. |
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