ZA200604973B - Amide derivatives bearing a cyclopropylaminoacarbonyl substituent useful as cytokine inhibitors - Google Patents
Amide derivatives bearing a cyclopropylaminoacarbonyl substituent useful as cytokine inhibitors Download PDFInfo
- Publication number
- ZA200604973B ZA200604973B ZA200604973A ZA200604973A ZA200604973B ZA 200604973 B ZA200604973 B ZA 200604973B ZA 200604973 A ZA200604973 A ZA 200604973A ZA 200604973 A ZA200604973 A ZA 200604973A ZA 200604973 B ZA200604973 B ZA 200604973B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- amino
- cyclopropyl
- methyl
- carbonyl
- Prior art date
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- 102000004127 Cytokines Human genes 0.000 title claims description 33
- 108090000695 Cytokines Proteins 0.000 title claims description 33
- 150000001408 amides Chemical class 0.000 title claims description 16
- 239000003112 inhibitor Substances 0.000 title description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 267
- -1 cyano, amino Chemical group 0.000 claims description 170
- 150000001875 compounds Chemical class 0.000 claims description 102
- 125000001424 substituent group Chemical group 0.000 claims description 79
- 125000003545 alkoxy group Chemical group 0.000 claims description 64
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 125000003282 alkyl amino group Chemical group 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 38
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 36
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000000304 alkynyl group Chemical group 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- 241001465754 Metazoa Species 0.000 claims description 23
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 238000011282 treatment Methods 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 18
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 17
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000001589 carboacyl group Chemical group 0.000 claims description 16
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 16
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 230000001404 mediated effect Effects 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000002541 furyl group Chemical group 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 7
- 206010040070 Septic Shock Diseases 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 208000030507 AIDS Diseases 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 208000031225 myocardial ischemia Diseases 0.000 claims description 4
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- KEYKHXIHAUQNSQ-UHFFFAOYSA-N 3-[[3-chloro-4-(1,3-thiazol-4-ylmethoxy)benzoyl]amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1Cl)=CC=C1OCC1=CSC=N1 KEYKHXIHAUQNSQ-UHFFFAOYSA-N 0.000 claims description 2
- NVOQVHARXGDSJR-UHFFFAOYSA-N 3-[[4-[(2-chloro-1,3-thiazol-5-yl)methoxy]benzoyl]amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CN=C(Cl)S1 NVOQVHARXGDSJR-UHFFFAOYSA-N 0.000 claims description 2
- YGEIVVROIJCKMK-UHFFFAOYSA-N methyl 6-[[4-[[5-(cyclopropylcarbamoyl)-2-methylphenyl]carbamoyl]phenoxy]methyl]pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OC)=CC=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1 YGEIVVROIJCKMK-UHFFFAOYSA-N 0.000 claims description 2
- UUCNRIPPUDGYJZ-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-[(1-methylbenzimidazol-2-yl)methoxy]pyrimidine-5-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(OCC=3N(C4=CC=CC=C4N=3)C)=NC=2)C(C)=CC=C1C(=O)NC1CC1 UUCNRIPPUDGYJZ-UHFFFAOYSA-N 0.000 claims description 2
- GJQNGUYXLNCNOG-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-5-(pyridin-2-ylmethoxy)pyrazine-2-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(N=C1)=CN=C1OCC1=CC=CC=N1 GJQNGUYXLNCNOG-UHFFFAOYSA-N 0.000 claims description 2
- CHAUORMHWHWMFD-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-5-(pyridin-2-ylmethoxy)pyridine-2-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(N=C1)=CC=C1OCC1=CC=CC=N1 CHAUORMHWHWMFD-UHFFFAOYSA-N 0.000 claims description 2
- DYMSGYJGZUFVCU-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-5-phenylmethoxypyridine-2-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(N=C1)=CC=C1OCC1=CC=CC=C1 DYMSGYJGZUFVCU-UHFFFAOYSA-N 0.000 claims description 2
- CKBKCCCGGPCZFF-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-6-(pyridin-2-ylmethoxy)pyridine-3-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=N1)=CC=C1OCC1=CC=CC=N1 CKBKCCCGGPCZFF-UHFFFAOYSA-N 0.000 claims description 2
- FIUHVZZFOWRRSM-UHFFFAOYSA-N n-cyclopropyl-3-[(3-methoxy-4-phenylmethoxybenzoyl)amino]-4-methylbenzamide Chemical compound COC1=CC(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=CC=C1OCC1=CC=CC=C1 FIUHVZZFOWRRSM-UHFFFAOYSA-N 0.000 claims description 2
- NYTZSRJYWPEXIS-UHFFFAOYSA-N n-cyclopropyl-3-[[3-fluoro-4-(1,2,5-thiadiazol-3-ylmethoxy)benzoyl]amino]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1F)=CC=C1OCC=1C=NSN=1 NYTZSRJYWPEXIS-UHFFFAOYSA-N 0.000 claims description 2
- QDWLBIGEMUNGMF-UHFFFAOYSA-N n-cyclopropyl-3-[[3-fluoro-4-(1,3-thiazol-4-ylmethoxy)benzoyl]amino]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1F)=CC=C1OCC1=CSC=N1 QDWLBIGEMUNGMF-UHFFFAOYSA-N 0.000 claims description 2
- JXVMZZLHKTWXRR-UHFFFAOYSA-N n-cyclopropyl-3-[[3-fluoro-4-(pyridin-2-ylmethoxy)benzoyl]amino]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1F)=CC=C1OCC1=CC=CC=N1 JXVMZZLHKTWXRR-UHFFFAOYSA-N 0.000 claims description 2
- ROXFBQYKGTUGHX-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoyl]amino]benzamide Chemical compound S1C(C)=NC(COC=2C=C(C=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=C1 ROXFBQYKGTUGHX-UHFFFAOYSA-N 0.000 claims description 2
- SCSQZJDBCZDXQR-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-(pyridin-2-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CC=N1 SCSQZJDBCZDXQR-UHFFFAOYSA-N 0.000 claims description 2
- BOIXDYSPJHDNPA-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-(pyridin-3-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CN=C1 BOIXDYSPJHDNPA-UHFFFAOYSA-N 0.000 claims description 2
- NKWDFZRDVVJAIZ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-(pyrimidin-2-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=NC=CC=N1 NKWDFZRDVVJAIZ-UHFFFAOYSA-N 0.000 claims description 2
- KRCMYCJDDWWXCQ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-[(1-oxidopyridin-1-ium-2-yl)methoxy]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CC=[N+]1[O-] KRCMYCJDDWWXCQ-UHFFFAOYSA-N 0.000 claims description 2
- MRRPHZPKLVNDRO-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-[(5-methyl-1,2-oxazol-3-yl)methoxy]benzoyl]amino]benzamide Chemical compound O1C(C)=CC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=N1 MRRPHZPKLVNDRO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- CRFFKUOMBBEIBL-UHFFFAOYSA-N 3-[(3-chloro-4-phenylmethoxybenzoyl)amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1Cl)=CC=C1OCC1=CC=CC=C1 CRFFKUOMBBEIBL-UHFFFAOYSA-N 0.000 claims 1
- GUJQUFWRZBBWOH-UHFFFAOYSA-N 3-[[3-[(2-chloro-1,3-thiazol-5-yl)methoxy]benzoyl]amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=1)=CC=CC=1OCC1=CN=C(Cl)S1 GUJQUFWRZBBWOH-UHFFFAOYSA-N 0.000 claims 1
- NDUQAWUYZZAUHQ-UHFFFAOYSA-N 3-[[3-chloro-4-(pyridin-2-ylmethoxy)benzoyl]amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1Cl)=CC=C1OCC1=CC=CC=N1 NDUQAWUYZZAUHQ-UHFFFAOYSA-N 0.000 claims 1
- AKILPBFLUQPGGH-UHFFFAOYSA-N 3-[[4-[(6-bromopyridin-2-yl)methoxy]benzoyl]amino]-N-cyclopropyl-4-methylbenzamide N-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-3,5-difluoro-4-(pyridin-2-ylmethoxy)benzamide Chemical compound Cc1ccc(cc1NC(=O)c1ccc(OCc2cccc(Br)n2)cc1)C(=O)NC1CC1.Cc1ccc(cc1NC(=O)c1cc(F)c(OCc2ccccn2)c(F)c1)C(=O)NC1CC1 AKILPBFLUQPGGH-UHFFFAOYSA-N 0.000 claims 1
- 150000003857 carboxamides Chemical class 0.000 claims 1
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
- DPNFDIXYWDPGAL-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(1,3-thiazol-2-ylmethoxy)pyrimidine-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=N1)=CN=C1OCC1=NC=CS1 DPNFDIXYWDPGAL-UHFFFAOYSA-N 0.000 claims 1
- OBBPDFGUYGAGOS-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(1,3-thiazol-4-ylmethoxy)pyrimidine-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=N1)=CN=C1OCC1=CSC=N1 OBBPDFGUYGAGOS-UHFFFAOYSA-N 0.000 claims 1
- CGNCAIQSPUBFQY-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(1-pyridin-2-ylethoxy)pyrimidine-5-carboxamide Chemical compound C=1C=CC=NC=1C(C)OC(N=C1)=NC=C1C(=O)NC(C(=CC=1)C)=CC=1C(=O)NC1CC1 CGNCAIQSPUBFQY-UHFFFAOYSA-N 0.000 claims 1
- NDSSRVYLMBPLJB-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-[(1,5-dimethylpyrazol-3-yl)methoxy]pyrimidine-5-carboxamide Chemical compound CN1C(C)=CC(COC=2N=CC(=CN=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=N1 NDSSRVYLMBPLJB-UHFFFAOYSA-N 0.000 claims 1
- XUIJBKCXVGNQAT-UHFFFAOYSA-N n-cyclopropyl-3-[[3-fluoro-4-(imidazo[1,2-a]pyridin-2-ylmethoxy)benzoyl]amino]-4-methylbenzamide Chemical compound C1=C(NC(=O)C=2C=C(F)C(OCC=3N=C4C=CC=CN4C=3)=CC=2)C(C)=CC=C1C(=O)NC1CC1 XUIJBKCXVGNQAT-UHFFFAOYSA-N 0.000 claims 1
- MKXHWCLSHMSVLA-UHFFFAOYSA-N n-cyclopropyl-3-[[3-methoxy-4-(1,3-thiazol-4-ylmethoxy)benzoyl]amino]-4-methylbenzamide Chemical compound COC1=CC(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=CC=C1OCC1=CSC=N1 MKXHWCLSHMSVLA-UHFFFAOYSA-N 0.000 claims 1
- QJMZGWBAXIYXBU-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]-3-fluorobenzoyl]amino]-4-methylbenzamide Chemical compound CC1=NOC(C)=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1F QJMZGWBAXIYXBU-UHFFFAOYSA-N 0.000 claims 1
- MJRLVOZIYUBYIK-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound CC1=NOC(C)=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1 MJRLVOZIYUBYIK-UHFFFAOYSA-N 0.000 claims 1
- DPKRLTFJKBPXQK-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[6-(hydroxymethyl)pyridin-2-yl]methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CC(CO)=N1 DPKRLTFJKBPXQK-UHFFFAOYSA-N 0.000 claims 1
- RGJDCDZQNWMQJI-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[6-[2-(dimethylamino)ethoxymethyl]pyridin-2-yl]methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound CN(C)CCOCC1=CC=CC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=N1 RGJDCDZQNWMQJI-UHFFFAOYSA-N 0.000 claims 1
- KZARPEAOZMWAHV-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[(3-methyl-4-phenylmethoxybenzoyl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1C)=CC=C1OCC1=CC=CC=C1 KZARPEAOZMWAHV-UHFFFAOYSA-N 0.000 claims 1
- GBDAAVCDIMPAGI-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[(3-phenylmethoxybenzoyl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=1)=CC=CC=1OCC1=CC=CC=C1 GBDAAVCDIMPAGI-UHFFFAOYSA-N 0.000 claims 1
- YSHUTGQPWMZNLS-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-(1,2,5-thiadiazol-3-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=1)=CC=CC=1OCC=1C=NSN=1 YSHUTGQPWMZNLS-UHFFFAOYSA-N 0.000 claims 1
- DHWDJIKRHNSUCZ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-(1,3-thiazol-4-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=1)=CC=CC=1OCC1=CSC=N1 DHWDJIKRHNSUCZ-UHFFFAOYSA-N 0.000 claims 1
- GNUDZHYXDDGOJQ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-(1,2,5-thiadiazol-3-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC=1C=NSN=1 GNUDZHYXDDGOJQ-UHFFFAOYSA-N 0.000 claims 1
- ZURALGORZUNFGK-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-(1-pyridin-2-ylethoxy)benzoyl]amino]benzamide Chemical compound C=1C=CC=NC=1C(C)OC(C=C1)=CC=C1C(=O)NC(C(=CC=1)C)=CC=1C(=O)NC1CC1 ZURALGORZUNFGK-UHFFFAOYSA-N 0.000 claims 1
- JRNQOPODJVELTQ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoyl]amino]benzamide Chemical compound S1C(C)=NC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=C1 JRNQOPODJVELTQ-UHFFFAOYSA-N 0.000 claims 1
- GAMAUDUCZONENJ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-[(3-methylpyridin-2-yl)methoxy]benzoyl]amino]benzamide Chemical compound CC1=CC=CN=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1 GAMAUDUCZONENJ-UHFFFAOYSA-N 0.000 claims 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 24
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- 238000012360 testing method Methods 0.000 description 15
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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GB0308201D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
GB0308186D0 (en) | 2003-04-09 | 2003-05-14 | Smithkline Beecham Corp | Novel compounds |
ES2386784T3 (es) | 2003-05-01 | 2012-08-30 | Bristol-Myers Squibb Company | Compuestos de pirazol-amina útiles como inhibidores de quinasas |
GB0324790D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Amide derivatives |
US7754717B2 (en) | 2005-08-15 | 2010-07-13 | Amgen Inc. | Bis-aryl amide compounds and methods of use |
CN101616667A (zh) * | 2006-10-27 | 2009-12-30 | 百时美施贵宝公司 | 可用作激酶抑制剂的杂环酰胺化合物 |
US20090281150A1 (en) * | 2008-04-09 | 2009-11-12 | Nicola Frances Bateman | Compound 249 |
WO2009138778A1 (en) * | 2008-05-12 | 2009-11-19 | Astrazeneca Ab | Cyclopropyl benzamide derivatives as intermediates for cytokine inhibitors |
WO2009151910A2 (en) * | 2008-05-25 | 2009-12-17 | Wyeth | Combination product of receptor tyrosine kinase inhibitor and fatty acid synthase inhibitor for treating cancer |
WO2011010132A1 (en) | 2009-07-21 | 2011-01-27 | Astrazeneca Ab | Sustained-release composition comprising compound 600 |
WO2016001452A1 (en) * | 2014-07-04 | 2016-01-07 | Universität Zürich | Compounds, in particular for use in the treatment of a disease or condition for which a bromodomain inhibitor is indicated |
US20200247761A1 (en) * | 2017-02-24 | 2020-08-06 | Taiwanj Pharmaceuticals Co., Ltd | Sulfonamide or amide compounds, compositions and methods for the prophylaxis and/or treatment of autoimmune, inflammation or infection related disorders |
WO2024039864A1 (en) * | 2022-08-19 | 2024-02-22 | Purdue Research Foundation | Protein:protein interaction inhibitors |
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US7772432B2 (en) | 1991-09-19 | 2010-08-10 | Astrazeneca Ab | Amidobenzamide derivatives which are useful as cytokine inhibitors |
GB9816837D0 (en) * | 1998-08-04 | 1998-09-30 | Zeneca Ltd | Amide derivatives |
US5843904A (en) * | 1995-12-20 | 1998-12-01 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1βconverting enzyme |
ATE296812T1 (de) * | 1998-03-09 | 2005-06-15 | Vertex Pharma | 1,2-diazepanderivate als inhibitoren des interleukin-1beta umwandelnden enzyms |
GB2336362A (en) * | 1998-04-17 | 1999-10-20 | Xenova Ltd | Cytokine production inhibitors |
US5985837A (en) * | 1998-07-08 | 1999-11-16 | Basf Aktiengesellschaft | Dolastatin 15 derivatives |
MY138097A (en) * | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
EP1594854B1 (en) * | 2003-02-06 | 2010-09-01 | Bristol-Myers Squibb Company | Thiazolyl-based compounds useful as kinase inhibitors |
US7263483B2 (en) * | 2003-04-28 | 2007-08-28 | Dictaphone Corporation | USB dictation device |
GB0324790D0 (en) * | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Amide derivatives |
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