JP2015520752A5 - - Google Patents
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- Publication number
- JP2015520752A5 JP2015520752A5 JP2015511730A JP2015511730A JP2015520752A5 JP 2015520752 A5 JP2015520752 A5 JP 2015520752A5 JP 2015511730 A JP2015511730 A JP 2015511730A JP 2015511730 A JP2015511730 A JP 2015511730A JP 2015520752 A5 JP2015520752 A5 JP 2015520752A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- phenyl
- pyridazin
- azetidine
- piperidin
- 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.)
- Pending
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- 125000000304 alkynyl group Chemical group 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 125000003342 alkenyl group Chemical group 0.000 claims description 90
- 125000000623 heterocyclic group Chemical group 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 70
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 70
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 57
- OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 12
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 10
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 101100240516 Caenorhabditis elegans nhr-10 gene Proteins 0.000 claims description 5
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 5
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims description 5
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- -1 4-{[1- (tetrahydro-2H-pyran-4-ylacetyl) piperidin-4-yl] oxy} phenyl Chemical group 0.000 claims 648
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 416
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 270
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 118
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims 55
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 37
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 30
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 13
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 10
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 claims 7
- VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 208000030507 AIDS Diseases 0.000 claims 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 150000003857 carboxamides Chemical class 0.000 claims 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 4
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 4
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 3
- 206010006895 Cachexia Diseases 0.000 claims 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims 3
- 206010016654 Fibrosis Diseases 0.000 claims 3
- 208000017604 Hodgkin disease Diseases 0.000 claims 3
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 3
- 206010025323 Lymphomas Diseases 0.000 claims 3
- 208000001132 Osteoporosis Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 3
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 3
- 206010043189 Telangiectasia Diseases 0.000 claims 3
- 208000036142 Viral infection Diseases 0.000 claims 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 201000008937 atopic dermatitis Diseases 0.000 claims 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 3
- 210000000481 breast Anatomy 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 210000003169 central nervous system Anatomy 0.000 claims 3
- 210000003679 cervix uteri Anatomy 0.000 claims 3
- 210000001072 colon Anatomy 0.000 claims 3
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 230000004761 fibrosis Effects 0.000 claims 3
- 208000015181 infectious disease Diseases 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 208000032839 leukemia Diseases 0.000 claims 3
- 210000004072 lung Anatomy 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- 210000000056 organ Anatomy 0.000 claims 3
- 201000008482 osteoarthritis Diseases 0.000 claims 3
- 210000001672 ovary Anatomy 0.000 claims 3
- 210000000496 pancreas Anatomy 0.000 claims 3
- 210000002307 prostate Anatomy 0.000 claims 3
- 208000037803 restenosis Diseases 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 210000003491 skin Anatomy 0.000 claims 3
- 208000017520 skin disease Diseases 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 3
- 208000009056 telangiectasis Diseases 0.000 claims 3
- DAUYIKBTMNZABP-UHFFFAOYSA-N thiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1 DAUYIKBTMNZABP-UHFFFAOYSA-N 0.000 claims 3
- 210000001519 tissue Anatomy 0.000 claims 3
- 230000017423 tissue regeneration Effects 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 210000003932 urinary bladder Anatomy 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- AFNCBWNNOVTDGK-UHFFFAOYSA-N 1-methyl-5-[4-[(1-pyridazin-3-ylazetidine-3-carbonyl)amino]phenyl]pyrazole-3-carboxylic acid Chemical compound CN1N=C(C(O)=O)C=C1C(C=C1)=CC=C1NC(=O)C1CN(C=2N=NC=CC=2)C1 AFNCBWNNOVTDGK-UHFFFAOYSA-N 0.000 claims 2
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 2
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 2
- 125000000070 5-oxo-L-proline group Chemical group [H]N1[C@@](C(=O)[*])([H])C([H])([H])C([H])([H])C1=O 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims 2
- KGEXKCMGYQQMLW-UHFFFAOYSA-N n-pyridazin-3-ylazetidine-3-carboxamide Chemical compound C1NCC1C(=O)NC1=CC=CN=N1 KGEXKCMGYQQMLW-UHFFFAOYSA-N 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 230000037380 skin damage Effects 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- CFFQGPNPYLDEPC-NRFANRHFSA-N (3s)-1-(2-methylpyridin-3-yl)-n-[4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl]pyrrolidine-3-carboxamide Chemical compound CC1=NC=CC=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)CCC(F)(F)F)CC1 CFFQGPNPYLDEPC-NRFANRHFSA-N 0.000 claims 1
- LGKXFNXCSXWDCA-VWLOTQADSA-N (3s)-n-[4-(1-benzoylpiperidin-4-yl)phenyl]-1-(2-methylpyridin-3-yl)pyrrolidine-3-carboxamide Chemical compound CC1=NC=CC=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C=CC=CC=2)CC1 LGKXFNXCSXWDCA-VWLOTQADSA-N 0.000 claims 1
- DPPPEFNITFVTDY-DEOSSOPVSA-N (3s)-n-[4-(1-benzoylpiperidin-4-yl)phenyl]-1-(4-methylpyridazin-3-yl)pyrrolidine-3-carboxamide Chemical compound CC1=CC=NN=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C=CC=CC=2)CC1 DPPPEFNITFVTDY-DEOSSOPVSA-N 0.000 claims 1
- HRXSPZLJDLALOP-DEOSSOPVSA-N (3s)-n-[4-(1-benzoylpiperidin-4-yl)phenyl]-1-(6-methylpyridazin-3-yl)pyrrolidine-3-carboxamide Chemical compound N1=NC(C)=CC=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C=CC=CC=2)CC1 HRXSPZLJDLALOP-DEOSSOPVSA-N 0.000 claims 1
- SZXCWTSHMDPRJZ-NRFANRHFSA-N (3s)-n-[4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]phenyl]-1-(4-methylpyridazin-3-yl)pyrrolidine-3-carboxamide Chemical compound CC1=CC=NN=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C(C)(C)C)CC1 SZXCWTSHMDPRJZ-NRFANRHFSA-N 0.000 claims 1
- ZLYQUUMVCSOWTG-NRFANRHFSA-N (3s)-n-[4-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]phenyl]-1-(6-methylpyridazin-3-yl)pyrrolidine-3-carboxamide Chemical compound N1=NC(C)=CC=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C(C)(C)C)CC1 ZLYQUUMVCSOWTG-NRFANRHFSA-N 0.000 claims 1
- WALDIRUCVXEFFT-DEOSSOPVSA-N (3s)-n-[4-[1-(2-cyclopentylacetyl)piperidin-4-yl]phenyl]-1-pyridin-3-ylpyrrolidine-3-carboxamide Chemical compound O=C([C@@H]1CN(CC1)C=1C=NC=CC=1)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)CC1CCCC1 WALDIRUCVXEFFT-DEOSSOPVSA-N 0.000 claims 1
- PQFYGXUEGPMBBB-QHCPKHFHSA-N (3s)-n-[4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl]-1-(2-methylpyridin-3-yl)pyrrolidine-3-carboxamide Chemical compound CC1=NC=CC=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C(=CC=CC=2)F)CC1 PQFYGXUEGPMBBB-QHCPKHFHSA-N 0.000 claims 1
- RMVLRRDBYRXBFZ-QFIPXVFZSA-N (3s)-n-[4-[1-(2-fluorobenzoyl)piperidin-4-yl]phenyl]-1-(6-methylpyridazin-3-yl)pyrrolidine-3-carboxamide Chemical compound N1=NC(C)=CC=C1N1C[C@@H](C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C(=CC=CC=2)F)CC1 RMVLRRDBYRXBFZ-QFIPXVFZSA-N 0.000 claims 1
- YJHSZTJRQKVYKC-UHFFFAOYSA-N 1-(2-cyanopyridin-3-yl)-n-[4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl]azetidine-3-carboxamide Chemical compound C1CN(C(=O)C(C)(O)C)CCC1C(C=C1)=CC=C1NC(=O)C1CN(C=2C(=NC=CC=2)C#N)C1 YJHSZTJRQKVYKC-UHFFFAOYSA-N 0.000 claims 1
- KSBDOXBQIVLQCX-UHFFFAOYSA-N 1-(2-methylpyridin-3-yl)-n-[4-(1-pentanoylpiperidin-4-yl)phenyl]azetidine-3-carboxamide Chemical compound C1CN(C(=O)CCCC)CCC1C(C=C1)=CC=C1NC(=O)C1CN(C=2C(=NC=CC=2)C)C1 KSBDOXBQIVLQCX-UHFFFAOYSA-N 0.000 claims 1
- SEDBIAKWSHVRAG-UHFFFAOYSA-N 1-(2-methylpyridin-3-yl)-n-[4-(1-propanoylpiperidin-4-yl)phenyl]azetidine-3-carboxamide Chemical compound C1CN(C(=O)CC)CCC1C(C=C1)=CC=C1NC(=O)C1CN(C=2C(=NC=CC=2)C)C1 SEDBIAKWSHVRAG-UHFFFAOYSA-N 0.000 claims 1
- LAGSTDKHZWEKEI-UHFFFAOYSA-N 1-(2-methylpyridin-3-yl)-n-[4-[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]phenyl]azetidine-3-carboxamide Chemical compound CC1=NC=CC=C1N1CC(C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)CC(F)(F)F)C1 LAGSTDKHZWEKEI-UHFFFAOYSA-N 0.000 claims 1
- FZCQQQLSNRSDDF-UHFFFAOYSA-N 1-(2-methylpyridin-3-yl)-n-[4-[1-(4,4,4-trifluorobutanoyl)piperidin-4-yl]phenyl]azetidine-3-carboxamide Chemical compound CC1=NC=CC=C1N1CC(C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)CCC(F)(F)F)C1 FZCQQQLSNRSDDF-UHFFFAOYSA-N 0.000 claims 1
- DQYSOZAEYBERTP-UHFFFAOYSA-N 1-(2-methylpyridin-3-yl)-n-[4-[1-[4-(trifluoromethyl)benzoyl]piperidin-4-yl]phenyl]azetidine-3-carboxamide Chemical compound CC1=NC=CC=C1N1CC(C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C=CC(=CC=2)C(F)(F)F)C1 DQYSOZAEYBERTP-UHFFFAOYSA-N 0.000 claims 1
- IITCHUJZTMPPHI-UHFFFAOYSA-N 1-(4-cyanopyridin-3-yl)-n-[4-[1-(2-hydroxy-2-methylpropanoyl)piperidin-4-yl]phenyl]azetidine-3-carboxamide Chemical compound C1CN(C(=O)C(C)(O)C)CCC1C(C=C1)=CC=C1NC(=O)C1CN(C=2C(=CC=NC=2)C#N)C1 IITCHUJZTMPPHI-UHFFFAOYSA-N 0.000 claims 1
- IXXDXUKXEALHCM-UHFFFAOYSA-N 1-(6-fluoropyridazin-3-yl)-n-[4-[1-(2-methylpropanoyl)piperidin-4-yl]phenyl]azetidine-3-carboxamide Chemical compound C1CN(C(=O)C(C)C)CCC1C(C=C1)=CC=C1NC(=O)C1CN(C=2N=NC(F)=CC=2)C1 IXXDXUKXEALHCM-UHFFFAOYSA-N 0.000 claims 1
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims 1
- BEGIUDFULSWUTQ-HNNXBMFYSA-N 2-[1-(2-methylpropyl)pyrazol-4-yl]-n-[(3s)-1-pyridazin-3-ylpyrrolidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=NC=C(C(=O)N[C@@H]2CN(CC2)C=2N=NC=CC=2)S1 BEGIUDFULSWUTQ-HNNXBMFYSA-N 0.000 claims 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003816 2-hydroxybenzoyl group Chemical group OC1=C(C(=O)*)C=CC=C1 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000005916 2-methylpentyl group Chemical group 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- DSNABZXHIMPTJG-MRXNPFEDSA-N 5-[1-(2-methylpropyl)pyrazol-4-yl]-n-[(3r)-1-pyridazin-4-ylpyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)N[C@H]2CN(CC2)C=2C=NN=CC=2)S1 DSNABZXHIMPTJG-MRXNPFEDSA-N 0.000 claims 1
- DSNABZXHIMPTJG-INIZCTEOSA-N 5-[1-(2-methylpropyl)pyrazol-4-yl]-n-[(3s)-1-pyridazin-4-ylpyrrolidin-3-yl]thiophene-2-carboxamide Chemical compound C1=NN(CC(C)C)C=C1C1=CC=C(C(=O)N[C@@H]2CN(CC2)C=2C=NN=CC=2)S1 DSNABZXHIMPTJG-INIZCTEOSA-N 0.000 claims 1
- 208000028990 Skin injury Diseases 0.000 claims 1
- 208000000277 Splenic Neoplasms Diseases 0.000 claims 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- 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 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- XQYJYFKSVFZAMI-UHFFFAOYSA-N n-[4-(1-acetylpiperidin-4-yl)phenyl]-1-(2-methylpyridin-3-yl)azetidine-3-carboxamide Chemical compound C1CN(C(=O)C)CCC1C(C=C1)=CC=C1NC(=O)C1CN(C=2C(=NC=CC=2)C)C1 XQYJYFKSVFZAMI-UHFFFAOYSA-N 0.000 claims 1
- LPAQODLQHMVXLX-UHFFFAOYSA-N n-[4-(1-benzoylpiperidin-4-yl)phenyl]-1-(2-cyanopyridin-3-yl)azetidine-3-carboxamide Chemical compound C1N(C=2C(=NC=CC=2)C#N)CC1C(=O)NC(C=C1)=CC=C1C(CC1)CCN1C(=O)C1=CC=CC=C1 LPAQODLQHMVXLX-UHFFFAOYSA-N 0.000 claims 1
- OJUAUJFCYYPGLV-UHFFFAOYSA-N n-[4-(1-benzoylpiperidin-4-yl)phenyl]-1-(2-fluoro-6-methylpyridin-3-yl)azetidine-3-carboxamide Chemical compound FC1=NC(C)=CC=C1N1CC(C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C=CC=CC=2)C1 OJUAUJFCYYPGLV-UHFFFAOYSA-N 0.000 claims 1
- AEYPUVFOVVWCMP-UHFFFAOYSA-N n-[4-(1-benzoylpiperidin-4-yl)phenyl]-1-(2-methylpyridin-3-yl)azetidine-3-carboxamide Chemical compound CC1=NC=CC=C1N1CC(C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C=CC=CC=2)C1 AEYPUVFOVVWCMP-UHFFFAOYSA-N 0.000 claims 1
- WGTLDTUCKQYSOT-UHFFFAOYSA-N n-[4-(1-benzoylpiperidin-4-yl)phenyl]-1-(3-methylpyridazin-4-yl)azetidine-3-carboxamide Chemical compound CC1=NN=CC=C1N1CC(C(=O)NC=2C=CC(=CC=2)C2CCN(CC2)C(=O)C=2C=CC=CC=2)C1 WGTLDTUCKQYSOT-UHFFFAOYSA-N 0.000 claims 1
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| US20130303509A1 (en) * | 2012-05-11 | 2013-11-14 | Abbvie Inc. | Nampt inhibitors |
| TWI684600B (zh) | 2014-03-21 | 2020-02-11 | 美商艾伯維有限公司 | 抗－ｅｇｆｒ抗體及抗體藥物結合物 |
| EP3125920B1 (en) | 2014-04-04 | 2020-12-23 | Del Mar Pharmaceuticals | Dianhydrogalactitol, diacetyldianhydrogalactitol or dibromodulcitol to treat non-small-cell carcinoma of the lung and ovarian cancer |
| EA201692091A1 (ru) | 2014-04-18 | 2017-04-28 | Милленниум Фармасьютикалз, Инк. | Хиноксалиновые соединения и их применение |
| BR112016029662B1 (pt) | 2014-06-19 | 2023-10-24 | Takeda Pharmaceutical Company Limited | COMPOSTO DE FÓRMULA Bf OU UMA FORMA FARMACEUTICAMENTE ACEITÁVEL DO MESMO, COMPOSIÇÃO FARMACÊUTICA COMPREENDENDO O MESMO E SEU USO |
| EP3247705B1 (en) | 2015-01-20 | 2019-11-20 | Millennium Pharmaceuticals, Inc. | Quinazoline and quinoline compounds and uses thereof as nampt inhibitors |
| PL3464336T3 (pl) | 2016-06-01 | 2022-05-16 | Athira Pharma, Inc. | Związki |
| EP3468993A1 (en) | 2016-06-08 | 2019-04-17 | AbbVie Inc. | Anti-b7-h3 antibodies and antibody drug conjugates |
| JP2019521973A (ja) | 2016-06-08 | 2019-08-08 | アッヴィ・インコーポレイテッド | 抗ｂｈ７−ｈ３抗体及び抗体薬物コンジュゲート |
| MY199278A (en) | 2016-06-08 | 2023-10-24 | Abbvie Inc | Anti-b7-h3 antibodies and antibody drug conjugates |
| CN109562190A (zh) | 2016-06-08 | 2019-04-02 | 艾伯维公司 | 抗egfr抗体药物偶联物 |
| CN109600993A (zh) | 2016-06-08 | 2019-04-09 | 艾伯维公司 | 抗egfr抗体药物偶联物 |
| BR112018075630A2 (pt) | 2016-06-08 | 2019-03-19 | Abbvie Inc. | anticorpos anti-cd98 e conjugados de fármaco de anticorpo |
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