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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- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 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
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims 1
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- HHCPJRQYMYGFQC-UHFFFAOYSA-N n-(1-amino-2-methylpropan-2-yl)-4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-3-chlorobenzamide Chemical compound ClC1=CC(C(=O)NC(C)(CN)C)=CC=C1NC(=O)CC1=CC=C(Br)C(OC=2C=C(C=C(Cl)C=2)C#N)=C1F HHCPJRQYMYGFQC-UHFFFAOYSA-N 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
- 0 *c(cc1)cc(*)c1NC(Cc1c(*)c(O*)c(*)c(*)c1)=O Chemical compound *c(cc1)cc(*)c1NC(Cc1c(*)c(O*)c(*)c(*)c1)=O 0.000 description 5
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 2
- QMHZLVVYRNJZDT-UHFFFAOYSA-N 4-[[2-[4-bromo-3-(3-chloro-5-cyanophenoxy)-2-fluorophenyl]acetyl]amino]-n-[2-(1,1-dioxo-1,4-thiazinan-4-yl)ethyl]-3-methylbenzamide Chemical compound CC1=CC(C(=O)NCCN2CCS(=O)(=O)CC2)=CC=C1NC(=O)CC(C=1F)=CC=C(Br)C=1OC1=CC(Cl)=CC(C#N)=C1 QMHZLVVYRNJZDT-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
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| PCT/EP2006/067190 WO2007045572A1 (en) | 2005-10-19 | 2006-10-09 | N-phenyl phenylacetamide non-nucleoside reverse transcriptase inihibitors |
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| JP2009512659A JP2009512659A (ja) | 2009-03-26 |
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| EP2826770B1 (en) * | 2005-06-24 | 2018-09-12 | Biotron Limited | Acylguanidine compounds with antiviral activity |
| EP2029664A4 (en) | 2006-05-31 | 2015-09-09 | Dow Global Technologies Llc | ADJUVANTS FOR THE USE OF MICROWAVE ENERGY IN THE SELECTIVE HEATING OF THERMOPLASTIC POLYMER SYSTEMS |
| 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 |
| RU2451676C2 (ru) * | 2006-08-16 | 2012-05-27 | Ф.Хоффманн-Ля Рош Аг | Ненуклеозидные ингибиторы обратной транскриптазы |
| JP5167350B2 (ja) * | 2007-05-30 | 2013-03-21 | エフ．ホフマン−ラ ロシュ アーゲー | 非ヌクレオシド系逆転写酵素阻害剤 |
| JP2010530863A (ja) * | 2007-06-22 | 2010-09-16 | 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阻害剤としての尿素及びカルバマート誘導体 |
| KR20100088142A (ko) | 2007-11-20 | 2010-08-06 | 머크 샤프 앤드 돔 코포레이션 | 비-뉴클레오사이드 역전사효소 억제제 |
| WO2009080534A1 (en) * | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| 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 |
| HUE025336T2 (en) | 2010-03-30 | 2016-03-29 | Merck Canada Inc | Non-nucleoside reverse transcriptase inhibitors |
| EP2625292B1 (en) | 2010-10-07 | 2018-12-05 | The General Hospital Corporation | Biomarkers of cancer |
| 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 |
| JP6014155B2 (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． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| SG11201408284VA (en) * | 2012-05-22 | 2015-02-27 | Xenon Pharmaceuticals Inc | N-substituted benzamides and their use in the treatment of pain |
| US10071957B2 (en) | 2012-07-06 | 2018-09-11 | Genentech, Inc. | N-substituted benzamides and methods of use thereof |
| 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 |
| US20150307459A1 (en) | 2012-11-27 | 2015-10-29 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol Compounds and Their Use as Fungicides |
| WO2014082879A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4]triazole compounds |
| US20160029630A1 (en) | 2012-11-27 | 2016-02-04 | Basf Se | Substituted 2-[phenoxy-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds and their use as fungicides |
| WO2014082880A1 (en) | 2012-11-27 | 2014-06-05 | Basf Se | Substituted [1,2,4] triazole compounds |
| CA2895256C (en) | 2013-01-09 | 2021-06-01 | BASF Agro B.V. | Process for the preparation of substituted oxiranes and triazoles |
| US9550775B2 (en) | 2013-03-14 | 2017-01-24 | Genentech, Inc. | Substituted triazolopyridines and methods of use thereof |
| MX2015010775A (es) | 2013-03-15 | 2016-04-25 | Genentech Inc | Benzoxazoles sustituidos y metodos para usarlos. |
| RU2661399C1 (ru) * | 2013-11-22 | 2018-07-16 | Мерк Шарп И Доум Корп. | Композиция ненуклеозидного ингибитора обратной транскриптазы |
| CR20160296A (es) | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| PL3125894T3 (pl) | 2014-04-01 | 2021-02-08 | Merck Sharp & Dohme Corp. | Proleki inhibitorów odwrotnej transkryptazy hiv |
| EP3161159B1 (en) | 2014-06-25 | 2020-08-05 | The General Hospital Corporation | Targeting human satellite ii (hsatii) |
| CN106715418A (zh) | 2014-07-07 | 2017-05-24 | 基因泰克公司 | 治疗化合物及其使用方法 |
| JP2018520107A (ja) | 2015-05-22 | 2018-07-26 | ジェネンテック， インコーポレイテッド | 置換ベンズアミド及びその使用方法 |
| EP3341353A1 (en) | 2015-08-27 | 2018-07-04 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| 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 |
| US10899732B2 (en) | 2015-11-25 | 2021-01-26 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3854782A1 (en) | 2016-03-30 | 2021-07-28 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| AU2017347549A1 (en) | 2016-10-17 | 2019-05-02 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック， インコーポレイテッド | ナトリウムチャネル阻害剤としての４−ピペリジン−ｎ−（ピリミジン−４−イル）クロマン−７−スルホンアミド誘導体 |
| EP4317972A3 (en) | 2018-02-06 | 2024-03-13 | The General Hospital Corporation | Repeat rna as biomarkers of tumor immune response |
| AR114263A1 (es) | 2018-02-26 | 2020-08-12 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| WO2019191702A1 (en) | 2018-03-30 | 2019-10-03 | F. Hoffmann-La Roche Ag | Substituted hydro-pyrido-azines as sodium channel inhibitors |
| 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 |
| BRPI0510059B8 (pt) * | 2004-04-23 | 2021-05-25 | Hoffmann La Roche | inibidores da transcriptase reversa não-nucleosídica e seus usos |
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- 2006-10-09 CN CNA2006800383642A patent/CN101287702A/zh active Pending
- 2006-10-09 AT AT06807080T patent/ATE425138T1/de active
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