HRP20100592T1 - Amidni derivati koji nose ciklopropilaminokarbonilni supstituent korisni kao inhibitori citokina - Google Patents
Amidni derivati koji nose ciklopropilaminokarbonilni supstituent korisni kao inhibitori citokina Download PDFInfo
- Publication number
- HRP20100592T1 HRP20100592T1 HR20100592T HRP20100592T HRP20100592T1 HR P20100592 T1 HRP20100592 T1 HR P20100592T1 HR 20100592 T HR20100592 T HR 20100592T HR P20100592 T HRP20100592 T HR P20100592T HR P20100592 T1 HRP20100592 T1 HR P20100592T1
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- HR
- Croatia
- Prior art keywords
- alkyl
- amino
- cyclopropyl
- benzoyl
- carbonyl
- Prior art date
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- 102000004127 Cytokines Human genes 0.000 title claims 3
- 108090000695 Cytokines Proteins 0.000 title claims 3
- 150000001408 amides Chemical class 0.000 title claims 2
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 102
- 125000001424 substituent group Chemical group 0.000 claims abstract 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 23
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 12
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 11
- -1 cyano, amino Chemical group 0.000 claims abstract 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 6
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims abstract 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 6
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims abstract 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 238000010976 amide bond formation reaction Methods 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 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 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- BHXZHMWWMXDNAT-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-ylmethoxy)-n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]pyrimidine-5-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(OCC=3SC4=CC=CC=C4N=3)=NC=2)C(C)=CC=C1C(=O)NC1CC1 BHXZHMWWMXDNAT-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 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
- 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 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
- 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 1
- ORCVHJCFODUPRE-UHFFFAOYSA-N 3-[[4-[(5-chlorothiadiazol-4-yl)methoxy]benzoyl]amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC=1N=NSC=1Cl ORCVHJCFODUPRE-UHFFFAOYSA-N 0.000 claims 1
- SOTNDAPXFROTTN-UHFFFAOYSA-N 3-[[4-[(6-bromopyridin-2-yl)methoxy]benzoyl]amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CC(Br)=N1 SOTNDAPXFROTTN-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000006317 cyclopropyl amino group Chemical group 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
- 229940079593 drug Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- PRDVYKLAJQXOCO-UHFFFAOYSA-N methyl 5-[[4-[[5-(cyclopropylcarbamoyl)-2-methylphenyl]carbamoyl]-2-methylphenoxy]methyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1C PRDVYKLAJQXOCO-UHFFFAOYSA-N 0.000 claims 1
- GUIBHLZNMDFUKK-UHFFFAOYSA-N methyl 5-[[4-[[5-(cyclopropylcarbamoyl)-2-methylphenyl]carbamoyl]phenoxy]methyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1 GUIBHLZNMDFUKK-UHFFFAOYSA-N 0.000 claims 1
- WPHTYBHNSYYDHP-UHFFFAOYSA-N methyl 6-[[4-[[5-(cyclopropylcarbamoyl)-2-methylphenyl]carbamoyl]phenoxy]methyl]pyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=N1 WPHTYBHNSYYDHP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 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
- IRZPYVYXQGKEGM-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(imidazo[1,2-a]pyridin-2-ylmethoxy)pyrimidine-5-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(OCC=3N=C4C=CC=CN4C=3)=NC=2)C(C)=CC=C1C(=O)NC1CC1 IRZPYVYXQGKEGM-UHFFFAOYSA-N 0.000 claims 1
- IEIJOHAHSMSIFO-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(isoquinolin-1-ylmethoxy)pyrimidine-5-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(OCC=3C4=CC=CC=C4C=CN=3)=NC=2)C(C)=CC=C1C(=O)NC1CC1 IEIJOHAHSMSIFO-UHFFFAOYSA-N 0.000 claims 1
- WAVHMRVKMXUMDI-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(pyridin-2-ylmethoxy)pyrimidine-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=N1)=CN=C1OCC1=CC=CC=N1 WAVHMRVKMXUMDI-UHFFFAOYSA-N 0.000 claims 1
- RIGCMKRJWLLEGC-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(pyrimidin-2-ylmethoxy)pyrimidine-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=N1)=CN=C1OCC1=NC=CC=N1 RIGCMKRJWLLEGC-UHFFFAOYSA-N 0.000 claims 1
- JDSHMQAVHHSRLM-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-(quinolin-2-ylmethoxy)pyrimidine-5-carboxamide Chemical compound C1=C(NC(=O)C=2C=NC(OCC=3N=C4C=CC=CC4=CC=3)=NC=2)C(C)=CC=C1C(=O)NC1CC1 JDSHMQAVHHSRLM-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
- 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 1
- ZFEHEKQFTYKSOS-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-[(2,5-dimethylpyrazol-3-yl)methoxy]pyrimidine-5-carboxamide Chemical compound CN1N=C(C)C=C1COC1=NC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=N1 ZFEHEKQFTYKSOS-UHFFFAOYSA-N 0.000 claims 1
- JMRMWRGIDFFKPN-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-2-[(3-methylpyridin-2-yl)methoxy]pyrimidine-5-carboxamide Chemical compound CC1=CC=CN=C1COC1=NC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=N1 JMRMWRGIDFFKPN-UHFFFAOYSA-N 0.000 claims 1
- LZGJMFBUEJSFSE-UHFFFAOYSA-N n-[5-(cyclopropylcarbamoyl)-2-methylphenyl]-3,5-difluoro-4-(pyridin-2-ylmethoxy)benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1F)=CC(F)=C1OCC1=CC=CC=N1 LZGJMFBUEJSFSE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- IEPIQAQPDSGQJW-UHFFFAOYSA-N n-cyclopropyl-3-[(3-fluoro-4-phenylmethoxybenzoyl)amino]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1F)=CC=C1OCC1=CC=CC=C1 IEPIQAQPDSGQJW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XNVZCJSFGALHAY-UHFFFAOYSA-N n-cyclopropyl-3-[[3-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound CC1=NOC(C)=C1COC1=CC=CC(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=C1 XNVZCJSFGALHAY-UHFFFAOYSA-N 0.000 claims 1
- PDWGLDJEMXBAIR-UHFFFAOYSA-N n-cyclopropyl-3-[[3-[(4-methoxypyridin-2-yl)methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound COC1=CC=NC(COC=2C=C(C=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=C1 PDWGLDJEMXBAIR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- DJBYRUFEMZKUIE-UHFFFAOYSA-N n-cyclopropyl-3-[[3-fluoro-4-[(2-methyl-1,3-thiazol-4-yl)methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound S1C(C)=NC(COC=2C(=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)F)=C1 DJBYRUFEMZKUIE-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
- RAKOHNQGABLKRA-UHFFFAOYSA-N n-cyclopropyl-3-[[3-methoxy-4-(pyridin-2-ylmethoxy)benzoyl]amino]-4-methylbenzamide Chemical compound COC1=CC(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=CC=C1OCC1=CC=CC=N1 RAKOHNQGABLKRA-UHFFFAOYSA-N 0.000 claims 1
- DTWHPJDQOKWKHT-UHFFFAOYSA-N n-cyclopropyl-3-[[4-(imidazo[1,2-a]pyridin-2-ylmethoxy)benzoyl]amino]-4-methylbenzamide Chemical compound C1=C(NC(=O)C=2C=CC(OCC=3N=C4C=CC=CN4C=3)=CC=2)C(C)=CC=C1C(=O)NC1CC1 DTWHPJDQOKWKHT-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
- FDUVZHNTUIUBIC-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[(3,5-dimethyl-1,2-oxazol-4-yl)methoxy]-3-methylbenzoyl]amino]-4-methylbenzamide Chemical compound CC1=NOC(C)=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1C FDUVZHNTUIUBIC-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
- GUESHRARJHEJFS-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[(4-methoxypyridin-2-yl)methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound COC1=CC=NC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=C1 GUESHRARJHEJFS-UHFFFAOYSA-N 0.000 claims 1
- ZUPKXKCDGIMNJI-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[(5-cyclopropyl-1,3,4-thiadiazol-2-yl)methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC(S1)=NN=C1C1CC1 ZUPKXKCDGIMNJI-UHFFFAOYSA-N 0.000 claims 1
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- JWEQZXHEMJYJQN-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[5-(2-hydroxypropan-2-yl)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=C(C(C)(C)O)C=N1 JWEQZXHEMJYJQN-UHFFFAOYSA-N 0.000 claims 1
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- RBWMGTFXLGCYKC-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[5-[(dimethylamino)methyl]pyridin-2-yl]methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound N1=CC(CN(C)C)=CC=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1 RBWMGTFXLGCYKC-UHFFFAOYSA-N 0.000 claims 1
- GWSMRWRYCPFTGD-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[5-[2-(dimethylamino)ethoxy]pyridin-2-yl]methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound N1=CC(OCCN(C)C)=CC=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1 GWSMRWRYCPFTGD-UHFFFAOYSA-N 0.000 claims 1
- VXLSWXFBHXHNIP-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[6-(2-hydroxypropan-2-yl)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(C(C)(C)O)=N1 VXLSWXFBHXHNIP-UHFFFAOYSA-N 0.000 claims 1
- IMGLHCYVGCHEFN-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[6-(2-methoxyethylamino)pyridin-2-yl]methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound COCCNC1=CC=CC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=N1 IMGLHCYVGCHEFN-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
- NHMPWBZQHGSDTH-UHFFFAOYSA-N n-cyclopropyl-3-[[4-[[6-[2-(diethylamino)ethoxymethyl]pyridin-2-yl]methoxy]benzoyl]amino]-4-methylbenzamide Chemical compound CCN(CC)CCOCC1=CC=CC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=N1 NHMPWBZQHGSDTH-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
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- NAAWMSIRMSPBPH-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[(4-phenylmethoxybenzoyl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 NAAWMSIRMSPBPH-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
- GKDOKLHBNOWSEP-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-(pyridin-2-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=1)=CC=CC=1OCC1=CC=CC=N1 GKDOKLHBNOWSEP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- OAOUEUXVKOJXAL-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-methyl-4-(1,2,5-thiadiazol-3-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1C)=CC=C1OCC=1C=NSN=1 OAOUEUXVKOJXAL-UHFFFAOYSA-N 0.000 claims 1
- IWVDXIOKHUSYDZ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-methyl-4-(1,3-thiazol-4-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1C)=CC=C1OCC1=CSC=N1 IWVDXIOKHUSYDZ-UHFFFAOYSA-N 0.000 claims 1
- QBGOKVWMOODILS-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-methyl-4-(pyridin-2-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1C)=CC=C1OCC1=CC=CC=N1 QBGOKVWMOODILS-UHFFFAOYSA-N 0.000 claims 1
- DJKIIOQWZMWSAI-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[3-methyl-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)C)=C1 DJKIIOQWZMWSAI-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
- XDXAVNILVYGRLO-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-(1,3-thiazol-4-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CSC=N1 XDXAVNILVYGRLO-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
- ATWDVJWCKWDFDQ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-(pyridazin-3-ylmethoxy)benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=CN=N1 ATWDVJWCKWDFDQ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 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
- KDQCKVVZQVOWCL-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-[(4-methylsulfonylphenyl)methoxy]benzoyl]amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(=O)C(C=C1)=CC=C1OCC1=CC=C(S(C)(=O)=O)C=C1 KDQCKVVZQVOWCL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XROQPTQMFOJKNG-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-[(6-methylpyridin-2-yl)methoxy]benzoyl]amino]benzamide Chemical compound CC1=CC=CC(COC=2C=CC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)=N1 XROQPTQMFOJKNG-UHFFFAOYSA-N 0.000 claims 1
- BEBZRQBZMMYQFX-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[[4-[[5-[(propan-2-ylamino)methyl]pyridin-2-yl]methoxy]benzoyl]amino]benzamide Chemical compound N1=CC(CNC(C)C)=CC=C1COC1=CC=C(C(=O)NC=2C(=CC=C(C=2)C(=O)NC2CC2)C)C=C1 BEBZRQBZMMYQFX-UHFFFAOYSA-N 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
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- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Virology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Physical Education & Sports Medicine (AREA)
- Molecular Biology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- AIDS & HIV (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0329572.2A GB0329572D0 (en) | 2003-12-20 | 2003-12-20 | Amide derivatives |
| PCT/GB2004/005241 WO2005061465A1 (en) | 2003-12-20 | 2004-12-15 | Amide derivatives bearing a cyclopropylaminoacarbonyl substituent useful as cyto kine inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20100592T1 true HRP20100592T1 (hr) | 2010-12-31 |
Family
ID=30776197
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20100592T HRP20100592T1 (hr) | 2003-12-20 | 2010-11-03 | Amidni derivati koji nose ciklopropilaminokarbonilni supstituent korisni kao inhibitori citokina |
Country Status (34)
| Country | Link |
|---|---|
| US (3) | US7943776B2 (ar) |
| EP (1) | EP1699766B1 (ar) |
| JP (1) | JP5046650B2 (ar) |
| KR (1) | KR101151530B1 (ar) |
| CN (1) | CN1918134B (ar) |
| AR (1) | AR046968A1 (ar) |
| AT (1) | ATE477246T1 (ar) |
| AU (1) | AU2004303579B8 (ar) |
| BR (1) | BRPI0417844A (ar) |
| CA (1) | CA2547617C (ar) |
| CY (1) | CY1111980T1 (ar) |
| DE (1) | DE602004028656D1 (ar) |
| DK (1) | DK1699766T3 (ar) |
| ES (1) | ES2350226T3 (ar) |
| GB (1) | GB0329572D0 (ar) |
| HK (1) | HK1092797A1 (ar) |
| HR (1) | HRP20100592T1 (ar) |
| IL (1) | IL175998A0 (ar) |
| ME (1) | ME01851B (ar) |
| MX (1) | MXPA06006660A (ar) |
| MY (1) | MY145908A (ar) |
| NO (1) | NO337886B1 (ar) |
| NZ (1) | NZ547998A (ar) |
| PL (1) | PL1699766T3 (ar) |
| PT (1) | PT1699766E (ar) |
| RS (1) | RS51417B (ar) |
| RU (1) | RU2382028C2 (ar) |
| SA (1) | SA04250419B1 (ar) |
| SI (1) | SI1699766T1 (ar) |
| TW (1) | TWI342214B (ar) |
| UA (1) | UA88777C2 (ar) |
| UY (1) | UY28688A1 (ar) |
| WO (1) | WO2005061465A1 (ar) |
| ZA (1) | ZA200604973B (ar) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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2003
- 2003-12-20 GB GBGB0329572.2A patent/GB0329572D0/en not_active Ceased
-
2004
- 2004-12-15 NZ NZ547998A patent/NZ547998A/en not_active IP Right Cessation
- 2004-12-15 DK DK04806056.0T patent/DK1699766T3/da active
- 2004-12-15 KR KR1020067012125A patent/KR101151530B1/ko not_active IP Right Cessation
- 2004-12-15 DE DE602004028656T patent/DE602004028656D1/de active Active
- 2004-12-15 CA CA2547617A patent/CA2547617C/en not_active Expired - Fee Related
- 2004-12-15 AT AT04806056T patent/ATE477246T1/de active
- 2004-12-15 UA UAA200606333A patent/UA88777C2/ru unknown
- 2004-12-15 AU AU2004303579A patent/AU2004303579B8/en not_active Ceased
- 2004-12-15 PL PL04806056T patent/PL1699766T3/pl unknown
- 2004-12-15 RU RU2006125634/04A patent/RU2382028C2/ru not_active IP Right Cessation
- 2004-12-15 SI SI200431529T patent/SI1699766T1/sl unknown
- 2004-12-15 BR BRPI0417844-0A patent/BRPI0417844A/pt not_active Application Discontinuation
- 2004-12-15 EP EP04806056A patent/EP1699766B1/en active Active
- 2004-12-15 PT PT04806056T patent/PT1699766E/pt unknown
- 2004-12-15 US US10/581,305 patent/US7943776B2/en not_active Expired - Fee Related
- 2004-12-15 MX MXPA06006660A patent/MXPA06006660A/es active IP Right Grant
- 2004-12-15 WO PCT/GB2004/005241 patent/WO2005061465A1/en active Application Filing
- 2004-12-15 RS RSP-2010/0414A patent/RS51417B/en unknown
- 2004-12-15 CN CN2004800418873A patent/CN1918134B/zh not_active Expired - Fee Related
- 2004-12-15 ME MEP-2010-414A patent/ME01851B/me unknown
- 2004-12-15 JP JP2006544544A patent/JP5046650B2/ja not_active Expired - Fee Related
- 2004-12-15 ES ES04806056T patent/ES2350226T3/es active Active
- 2004-12-17 MY MYPI20045224A patent/MY145908A/en unknown
- 2004-12-18 SA SA04250419A patent/SA04250419B1/ar unknown
- 2004-12-20 TW TW093139710A patent/TWI342214B/zh not_active IP Right Cessation
- 2004-12-20 UY UY28688A patent/UY28688A1/es not_active Application Discontinuation
- 2004-12-20 AR ARP040104794A patent/AR046968A1/es unknown
-
2006
- 2006-05-29 IL IL175998A patent/IL175998A0/en not_active IP Right Cessation
- 2006-06-15 ZA ZA200604973A patent/ZA200604973B/en unknown
- 2006-07-18 NO NO20063330A patent/NO337886B1/no not_active IP Right Cessation
- 2006-12-06 HK HK06113410.9A patent/HK1092797A1/xx not_active IP Right Cessation
-
2010
- 2010-11-03 HR HR20100592T patent/HRP20100592T1/hr unknown
- 2010-11-11 CY CY20101101016T patent/CY1111980T1/el unknown
-
2011
- 2011-04-05 US US13/080,583 patent/US20120004243A1/en not_active Abandoned
-
2012
- 2012-09-27 US US13/628,958 patent/US8742124B2/en not_active Expired - Fee Related
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