JP2008500336A5 - - Google Patents
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- JP2008500336A5 JP2008500336A5 JP2007514980A JP2007514980A JP2008500336A5 JP 2008500336 A5 JP2008500336 A5 JP 2008500336A5 JP 2007514980 A JP2007514980 A JP 2007514980A JP 2007514980 A JP2007514980 A JP 2007514980A JP 2008500336 A5 JP2008500336 A5 JP 2008500336A5
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- JP
- Japan
- Prior art keywords
- alkyl
- amino
- alkoxy
- carboxamide
- aryl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 248
- 125000003545 alkoxy group Chemical group 0.000 claims 169
- -1 cyano, amino, acetylamino, hydroxyl Chemical group 0.000 claims 134
- 125000000623 heterocyclic group Chemical group 0.000 claims 99
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 83
- 125000003118 aryl group Chemical group 0.000 claims 77
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 63
- 125000001072 heteroaryl group Chemical group 0.000 claims 55
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 44
- 229910052736 halogen Inorganic materials 0.000 claims 43
- 150000002367 halogens Chemical class 0.000 claims 38
- 150000001350 alkyl halides Chemical class 0.000 claims 37
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 33
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- 125000004103 aminoalkyl group Chemical group 0.000 claims 31
- 125000005842 heteroatom Chemical group 0.000 claims 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims 27
- 125000003342 alkenyl group Chemical group 0.000 claims 25
- 125000003710 aryl alkyl group Chemical group 0.000 claims 25
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 25
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 22
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 22
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 22
- 150000002431 hydrogen Chemical class 0.000 claims 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 21
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 21
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims 16
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 16
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 15
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000003282 alkyl amino group Chemical group 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 5
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- SICXGWWUMIAMRS-UHFFFAOYSA-N 3-benzamido-2,6-dimethyl-n-phenylpyridine-4-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC=1C(C)=NC(C)=CC=1C(=O)NC1=CC=CC=C1 SICXGWWUMIAMRS-UHFFFAOYSA-N 0.000 claims 3
- BNCWAGNRFLQKQR-UHFFFAOYSA-N 3-benzamido-n-benzylpyridine-2-carboxamide Chemical compound N=1C=CC=C(NC(=O)C=2C=CC=CC=2)C=1C(=O)NCC1=CC=CC=C1 BNCWAGNRFLQKQR-UHFFFAOYSA-N 0.000 claims 3
- YRKMZPUFKOXPRF-UHFFFAOYSA-N 3-benzamido-n-phenylpyridine-2-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CN=C1C(=O)NC1=CC=CC=C1 YRKMZPUFKOXPRF-UHFFFAOYSA-N 0.000 claims 3
- UBECMWWEVLSFMW-UHFFFAOYSA-N 3-benzamido-n-pyridin-3-ylpyridine-2-carboxamide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CN=C1C(=O)NC1=CC=CN=C1 UBECMWWEVLSFMW-UHFFFAOYSA-N 0.000 claims 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- VGSNSYDOPNZQRP-UHFFFAOYSA-N 3-[(4-tert-butylbenzoyl)amino]-n-(5-chloropyridin-2-yl)pyrazine-2-carboxamide Chemical group C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC=CN=C1C(=O)NC1=CC=C(Cl)C=N1 VGSNSYDOPNZQRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 229960003966 nicotinamide Drugs 0.000 claims 2
- 235000005152 nicotinamide Nutrition 0.000 claims 2
- 239000011570 nicotinamide Substances 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229960005206 pyrazinamide Drugs 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims 1
- AFCYJROVCWBNDH-UHFFFAOYSA-N 1-n-[2-(cyclobutylmethylcarbamoyl)pyridin-3-yl]-4-n,4-n-dimethylnaphthalene-1,4-dicarboxamide Chemical compound C12=CC=CC=C2C(C(=O)N(C)C)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCC1 AFCYJROVCWBNDH-UHFFFAOYSA-N 0.000 claims 1
- ZBDVLRMVASOXFS-UHFFFAOYSA-N 1-n-[2-(cyclohexylmethylcarbamoyl)pyridin-3-yl]-4-n,4-n-dimethylnaphthalene-1,4-dicarboxamide Chemical compound C12=CC=CC=C2C(C(=O)N(C)C)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCCCC1 ZBDVLRMVASOXFS-UHFFFAOYSA-N 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- ZZFOZUWZXKJPEY-UHFFFAOYSA-N 2-hydroxyethyl 4-[[2-(oxan-4-ylmethylcarbamoyl)pyridin-3-yl]carbamoyl]naphthalene-1-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OCCO)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 ZZFOZUWZXKJPEY-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- CMHDGZIUTULGFI-UHFFFAOYSA-N 3-(naphthalene-1-carbonylamino)-n-(2-piperidin-1-ylethyl)pyridine-2-carboxamide Chemical compound N=1C=CC=C(NC(=O)C=2C3=CC=CC=C3C=CC=2)C=1C(=O)NCCN1CCCCC1 CMHDGZIUTULGFI-UHFFFAOYSA-N 0.000 claims 1
- VUJZZCYIZJZDBJ-UHFFFAOYSA-N 3-(naphthalene-1-carbonylamino)-n-(2-pyrrolidin-1-ylethyl)pyridine-2-carboxamide Chemical compound N=1C=CC=C(NC(=O)C=2C3=CC=CC=C3C=CC=2)C=1C(=O)NCCN1CCCC1 VUJZZCYIZJZDBJ-UHFFFAOYSA-N 0.000 claims 1
- RBHVESNGDMPRCZ-UHFFFAOYSA-N 3-(naphthalene-1-carbonylamino)-n-(oxan-4-yl)pyridine-2-carboxamide Chemical compound N=1C=CC=C(NC(=O)C=2C3=CC=CC=C3C=CC=2)C=1C(=O)NC1CCOCC1 RBHVESNGDMPRCZ-UHFFFAOYSA-N 0.000 claims 1
- KQLKVUTUWJRUOQ-UHFFFAOYSA-N 3-(naphthalene-1-carbonylamino)-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 KQLKVUTUWJRUOQ-UHFFFAOYSA-N 0.000 claims 1
- WUYVRYKGHYWEIU-UHFFFAOYSA-N 3-(naphthalene-1-carbonylamino)-n-(piperidin-2-ylmethyl)pyridine-2-carboxamide Chemical compound N=1C=CC=C(NC(=O)C=2C3=CC=CC=C3C=CC=2)C=1C(=O)NCC1CCCCN1 WUYVRYKGHYWEIU-UHFFFAOYSA-N 0.000 claims 1
- LQHXTNIRBNKMSH-UHFFFAOYSA-N 3-[(4-acetamidonaphthalene-1-carbonyl)amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(NC(=O)C)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 LQHXTNIRBNKMSH-UHFFFAOYSA-N 0.000 claims 1
- KKMNBDMDAIVQLS-UHFFFAOYSA-N 3-[(4-aminonaphthalene-1-carbonyl)amino]-n-(cyclohexylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(N)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCCCC1 KKMNBDMDAIVQLS-UHFFFAOYSA-N 0.000 claims 1
- ARHKCIXSCVAUKZ-UHFFFAOYSA-N 3-[(4-aminonaphthalene-1-carbonyl)amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(N)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 ARHKCIXSCVAUKZ-UHFFFAOYSA-N 0.000 claims 1
- DANLUEKVPQFPIK-UHFFFAOYSA-N 3-[(4-ethoxynaphthalene-1-carbonyl)amino]-n-pentylpyridine-2-carboxamide Chemical compound CCCCCNC(=O)C1=NC=CC=C1NC(=O)C1=CC=C(OCC)C2=CC=CC=C12 DANLUEKVPQFPIK-UHFFFAOYSA-N 0.000 claims 1
- AUYVUUVZZPZBPU-UHFFFAOYSA-N 3-[(4-ethylnaphthalene-1-carbonyl)amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(CC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 AUYVUUVZZPZBPU-UHFFFAOYSA-N 0.000 claims 1
- VAFYJJFBKRRXDW-UHFFFAOYSA-N 3-[(4-methoxynaphthalene-1-carbonyl)amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(OC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 VAFYJJFBKRRXDW-UHFFFAOYSA-N 0.000 claims 1
- IWKBXLMNASRWLY-UHFFFAOYSA-N 3-[(4-methoxynaphthalene-1-carbonyl)amino]-n-(oxolan-2-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(OC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCCO1 IWKBXLMNASRWLY-UHFFFAOYSA-N 0.000 claims 1
- GZJWVIHFFWCOPK-UHFFFAOYSA-N 3-[(4-methylnaphthalene-1-carbonyl)amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(C)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 GZJWVIHFFWCOPK-UHFFFAOYSA-N 0.000 claims 1
- UCBNKKXVXPJPMQ-UHFFFAOYSA-N 3-[(4-methylnaphthalene-1-carbonyl)amino]-n-[2-(oxan-4-yl)ethyl]pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(C)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCCC1CCOCC1 UCBNKKXVXPJPMQ-UHFFFAOYSA-N 0.000 claims 1
- FKRBDYNUBOVEMJ-UHFFFAOYSA-N 3-[(4-methylnaphthalene-1-carbonyl)amino]-n-pentylpyrazine-2-carboxamide Chemical compound CCCCCNC(=O)C1=NC=CN=C1NC(=O)C1=CC=C(C)C2=CC=CC=C12 FKRBDYNUBOVEMJ-UHFFFAOYSA-N 0.000 claims 1
- TZMOLSGECSETTL-UHFFFAOYSA-N 3-[[4-(dimethylamino)naphthalene-1-carbonyl]amino]-n-(2-ethylbutyl)pyridine-2-carboxamide Chemical compound CCC(CC)CNC(=O)C1=NC=CC=C1NC(=O)C1=CC=C(N(C)C)C2=CC=CC=C12 TZMOLSGECSETTL-UHFFFAOYSA-N 0.000 claims 1
- CAZHXNNYYXIULX-UHFFFAOYSA-N 3-[[4-(dimethylamino)naphthalene-1-carbonyl]amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(N(C)C)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 CAZHXNNYYXIULX-UHFFFAOYSA-N 0.000 claims 1
- MINUDTBJCJQJJF-UHFFFAOYSA-N 3-[[4-(dimethylamino)naphthalene-1-carbonyl]amino]-n-[3-(dimethylamino)propyl]pyridine-2-carboxamide Chemical compound CN(C)CCCNC(=O)C1=NC=CC=C1NC(=O)C1=CC=C(N(C)C)C2=CC=CC=C12 MINUDTBJCJQJJF-UHFFFAOYSA-N 0.000 claims 1
- SOJXPRBKIKHWKF-UHFFFAOYSA-N 3-[[4-(dimethylamino)naphthalene-1-carbonyl]amino]-n-hexylpyridine-2-carboxamide Chemical compound CCCCCCNC(=O)C1=NC=CC=C1NC(=O)C1=CC=C(N(C)C)C2=CC=CC=C12 SOJXPRBKIKHWKF-UHFFFAOYSA-N 0.000 claims 1
- HIKSPCQQKBCYJV-UHFFFAOYSA-N 3-[[4-(dimethylamino)naphthalene-1-carbonyl]amino]-n-pentylpyridine-2-carboxamide Chemical compound CCCCCNC(=O)C1=NC=CC=C1NC(=O)C1=CC=C(N(C)C)C2=CC=CC=C12 HIKSPCQQKBCYJV-UHFFFAOYSA-N 0.000 claims 1
- PIYPUGUVIWSELE-UHFFFAOYSA-N 3-[[4-(dimethylamino)naphthalene-1-carbonyl]amino]-n-propylpyridine-2-carboxamide Chemical compound CCCNC(=O)C1=NC=CC=C1NC(=O)C1=CC=C(N(C)C)C2=CC=CC=C12 PIYPUGUVIWSELE-UHFFFAOYSA-N 0.000 claims 1
- VROLXBOMUUAGIQ-UHFFFAOYSA-N 3-[[4-(ethoxymethyl)naphthalene-1-carbonyl]amino]-n-(piperidin-2-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(COCC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCCCN1 VROLXBOMUUAGIQ-UHFFFAOYSA-N 0.000 claims 1
- GPRFZPJQJHSGHC-UHFFFAOYSA-N 3-[[4-(furan-2-ylmethyl)naphthalene-1-carbonyl]amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound N=1C=CC=C(NC(=O)C=2C3=CC=CC=C3C(CC=3OC=CC=3)=CC=2)C=1C(=O)NCC1CCOCC1 GPRFZPJQJHSGHC-UHFFFAOYSA-N 0.000 claims 1
- VTZXPPPNAXBVAZ-UHFFFAOYSA-N 3-[[4-(furan-3-ylmethyl)naphthalene-1-carbonyl]amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound N=1C=CC=C(NC(=O)C=2C3=CC=CC=C3C(CC3=COC=C3)=CC=2)C=1C(=O)NCC1CCOCC1 VTZXPPPNAXBVAZ-UHFFFAOYSA-N 0.000 claims 1
- XGOILZJXTXWENQ-UHFFFAOYSA-N 3-[[4-(imidazol-1-ylmethyl)naphthalene-1-carbonyl]amino]-n-(oxan-4-yl)pyridine-2-carboxamide Chemical compound C=1C=C(CN2C=NC=C2)C2=CC=CC=C2C=1C(=O)NC1=CC=CN=C1C(=O)NC1CCOCC1 XGOILZJXTXWENQ-UHFFFAOYSA-N 0.000 claims 1
- RWGTZNNPKDUWGX-UHFFFAOYSA-N 3-[[4-(methoxymethyl)naphthalene-1-carbonyl]amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(COC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 RWGTZNNPKDUWGX-UHFFFAOYSA-N 0.000 claims 1
- DZGSVZGJAXDUFF-UHFFFAOYSA-N 3-[[4-(methoxymethyl)naphthalene-1-carbonyl]amino]-n-(piperidin-2-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(COC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCCCN1 DZGSVZGJAXDUFF-UHFFFAOYSA-N 0.000 claims 1
- PYYUZMAIHXCAOH-UHFFFAOYSA-N 3-[[4-(methylcarbamoylamino)naphthalene-1-carbonyl]amino]-n-(oxan-4-ylmethyl)pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(NC(=O)NC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 PYYUZMAIHXCAOH-UHFFFAOYSA-N 0.000 claims 1
- YVITVABZYDPMHU-UHFFFAOYSA-N 6-methoxy-n-(oxan-4-ylmethyl)-3-[[4-(triazol-1-ylmethyl)naphthalene-1-carbonyl]amino]pyridine-2-carboxamide Chemical compound C1COCCC1CNC(=O)C1=NC(OC)=CC=C1NC(=O)C(C1=CC=CC=C11)=CC=C1CN1C=CN=N1 YVITVABZYDPMHU-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- YVIRVYMEHBTTNM-UHFFFAOYSA-N methyl 4-[[2-(oxan-4-ylmethylcarbamoyl)pyridin-3-yl]carbamoyl]naphthalene-1-carboxylate Chemical compound C12=CC=CC=C2C(C(=O)OC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 YVIRVYMEHBTTNM-UHFFFAOYSA-N 0.000 claims 1
- RHAHSVNEMOATCD-UHFFFAOYSA-N methyl n-[4-[[2-(oxan-4-ylmethylcarbamoyl)pyridin-3-yl]carbamoyl]naphthalen-1-yl]carbamate Chemical compound C12=CC=CC=C2C(NC(=O)OC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1CCOCC1 RHAHSVNEMOATCD-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- PZFLPELYIKTRKR-UHFFFAOYSA-N n-(1,4-dioxan-2-ylmethyl)-3-[(4-methoxynaphthalene-1-carbonyl)amino]pyridine-2-carboxamide Chemical compound C12=CC=CC=C2C(OC)=CC=C1C(=O)NC1=CC=CN=C1C(=O)NCC1COCCO1 PZFLPELYIKTRKR-UHFFFAOYSA-N 0.000 claims 1
- LARIXSJSSZHGON-UHFFFAOYSA-N n-(2-hydroxybutyl)-3-(naphthalene-1-carbonylamino)pyridine-2-carboxamide Chemical compound CCC(O)CNC(=O)C1=NC=CC=C1NC(=O)C1=CC=CC2=CC=CC=C12 LARIXSJSSZHGON-UHFFFAOYSA-N 0.000 claims 1
- JFHCHCDOJYXFKF-UHFFFAOYSA-N n-(2-hydroxypropyl)-3-(naphthalene-1-carbonylamino)pyridine-2-carboxamide Chemical compound CC(O)CNC(=O)C1=NC=CC=C1NC(=O)C1=CC=CC2=CC=CC=C12 JFHCHCDOJYXFKF-UHFFFAOYSA-N 0.000 claims 1
- PMIQFKNQCQUSQE-UHFFFAOYSA-N n-(2-methylcyclohexyl)-3-(naphthalene-1-carbonylamino)pyridine-2-carboxamide Chemical compound CC1CCCCC1NC(=O)C1=NC=CC=C1NC(=O)C1=CC=CC2=CC=CC=C12 PMIQFKNQCQUSQE-UHFFFAOYSA-N 0.000 claims 1
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| GB0611907D0 (en) | 2006-06-15 | 2006-07-26 | Glaxo Group Ltd | Compounds |
| MY150098A (en) | 2005-07-26 | 2013-11-29 | Glaxo Group Ltd | Benzylpiperazine derivates and their medical use |
| AR057987A1 (es) * | 2005-11-24 | 2008-01-09 | Astrazeneca Ab | Compuestos agonistas de cb1 (receptor cannabinoide) |
| GB0524814D0 (en) | 2005-12-05 | 2006-01-11 | Glaxo Group Ltd | Compounds |
| CA2645551C (en) | 2006-03-16 | 2016-06-28 | Renovis, Inc. | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof |
| US8841334B2 (en) | 2006-05-31 | 2014-09-23 | Abbvie Inc. | Compounds as cannabinoid receptor ligands and uses thereof |
| CN101448800A (zh) | 2006-05-31 | 2009-06-03 | 艾博特公司 | 作为大麻素受体配体的新型化合物及其用途 |
| PL2041093T3 (pl) | 2006-06-28 | 2010-09-30 | Glaxo Group Ltd | Pochodne piperazynylowe użyteczne w leczeniu zaburzeń, którym pośredniczy receptor GPR38 |
| CN101765594A (zh) | 2007-03-28 | 2010-06-30 | 雅培制药有限公司 | 作为大麻素受体配体的1,3-噻唑-2(3h)-亚基化合物 |
| US7872033B2 (en) | 2007-04-17 | 2011-01-18 | Abbott Laboratories | Compounds as cannabinoid receptor ligands |
| CN101711253A (zh) | 2007-05-18 | 2010-05-19 | 雅培制药有限公司 | 用作大麻素受体配体的新化合物 |
| US8338623B2 (en) | 2007-07-09 | 2012-12-25 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| US9193713B2 (en) | 2007-10-12 | 2015-11-24 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| EP2070925A1 (de) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Neue 2-substituierte Tiazol-4-carbonsäureamid-Derivative deren Herstellung und Verwendung als Arzneimittel |
| EP2070916A1 (de) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | 2-Aryl-thiazol-4-carbonsäureamid-Derivate, deren Herstellung und Verwendung als Arzneimittel |
| EP2070924A1 (de) | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Neue 2-Hetarylthiazol-4-carbonsäureamid-Derivative, deren Herstellung und Verwendung als Arzneimittel |
| JP5351254B2 (ja) | 2008-05-23 | 2013-11-27 | ノバルティス アーゲー | キノキサリン−およびキノリン−カルボキシアミド誘導体 |
| US8846730B2 (en) | 2008-09-08 | 2014-09-30 | Abbvie Inc. | Compounds as cannabinoid receptor ligands |
| TW201016692A (en) | 2008-09-16 | 2010-05-01 | Abbott Lab | Novel compounds as cannabinoid receptor ligands |
| PA8854001A1 (es) | 2008-12-16 | 2010-07-27 | Abbott Lab | Compuestos novedosos como ligandos de receptores de canabinoides |
| AU2010303567B2 (en) * | 2009-10-06 | 2016-06-09 | Millennium Pharmaceuticals, Inc | Heterocyclic compounds useful as PDK1 inhibitors |
| BR112015000695A2 (pt) | 2012-07-19 | 2017-06-27 | Nippon Soda Co | composto de piridina ou sais do mesmo, e, fungicida agrícola |
| KR20140011780A (ko) * | 2012-07-19 | 2014-01-29 | 한미약품 주식회사 | 단백질 키나아제 저해활성을 갖는 이소퀴놀린-5-카복스아미드 유도체 |
| AU2014347027A1 (en) | 2013-11-06 | 2016-06-23 | Bristol-Myers Squibb Company | GSK -3 inhibitors |
| KR102292433B1 (ko) * | 2013-11-06 | 2021-08-20 | 브리스톨-마이어스 스큅 컴퍼니 | Gsk-3 억제제로서 유용한 치환된 피리딘 유도체 |
| JP2019131470A (ja) * | 2016-05-20 | 2019-08-08 | 石原産業株式会社 | Ｎ−（４−ピリジル）ベンズアミド化合物又はその塩を有効成分として含有する有害生物防除剤 |
| WO2018199175A1 (ja) | 2017-04-27 | 2018-11-01 | 石原産業株式会社 | Ｎ－（４－ピリジル）ニコチンアミド化合物又はその塩 |
| CN107880024A (zh) * | 2017-12-11 | 2018-04-06 | 张玉玲 | 一种用于治疗炎症的大麻素受体激动剂及其合成方法 |
| BR112022010127A2 (pt) * | 2019-11-25 | 2022-09-06 | Gain Therapeutics Sa | Compostos de arila e heteroarila e usos terapêuticos dos mesmos em condições associadas à alteração da atividade de galatocerebrosidase |
| WO2021220178A1 (en) | 2020-04-29 | 2021-11-04 | Cominnex Zrt. | Iap antagonists and their therapeutic applications |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0054132B1 (de) * | 1980-12-12 | 1984-10-10 | Dr. Karl Thomae GmbH | Neue Pyrimidinone, ihre Herstellung und Arzneimittel mit einem Gehalt an diesen Stoffen |
| DE3046871A1 (de) * | 1980-12-12 | 1982-07-22 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue chinazolinone, ihre herstellung und ihre verwendung als arzneimittel |
| GB9717576D0 (en) * | 1997-08-19 | 1997-10-22 | Xenova Ltd | Pharmaceutical compounds |
| PL364660A1 (en) * | 2001-03-05 | 2004-12-13 | E.I.Du Pont De Nemours And Company | Heterocyclic diamide invertebrate pest control agents |
| GB0222493D0 (en) * | 2002-09-27 | 2002-11-06 | Glaxo Group Ltd | Compounds |
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2004
- 2004-05-25 SE SE0401345A patent/SE0401345D0/xx unknown
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2005
- 2005-05-12 TW TW094115320A patent/TW200607799A/zh unknown
- 2005-05-20 BR BRPI0511531-0A patent/BRPI0511531A/pt not_active Application Discontinuation
- 2005-05-20 EP EP05745177A patent/EP1756060A1/en not_active Withdrawn
- 2005-05-20 MX MXPA06013538A patent/MXPA06013538A/es unknown
- 2005-05-20 AU AU2005247834A patent/AU2005247834A1/en not_active Abandoned
- 2005-05-20 KR KR1020067024936A patent/KR20070026540A/ko not_active Withdrawn
- 2005-05-20 RU RU2006145205/04A patent/RU2006145205A/ru unknown
- 2005-05-20 US US11/569,315 patent/US20070225292A1/en not_active Abandoned
- 2005-05-20 JP JP2007514980A patent/JP2008500336A/ja active Pending
- 2005-05-20 CA CA002565065A patent/CA2565065A1/en not_active Abandoned
- 2005-05-20 WO PCT/SE2005/000753 patent/WO2005115986A1/en not_active Ceased
- 2005-05-20 CN CNA2005800246960A patent/CN101001840A/zh active Pending
- 2005-05-23 AR ARP050102119A patent/AR049110A1/es not_active Application Discontinuation
- 2005-05-25 UY UY28923A patent/UY28923A1/es not_active Application Discontinuation
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2006
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- 2006-11-23 ZA ZA200609765A patent/ZA200609765B/xx unknown
- 2006-12-18 NO NO20065878A patent/NO20065878L/no unknown
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