CA2485909C - Azepinoindole and pyridoindole derivatives as pharmaceutical agents - Google Patents
Azepinoindole and pyridoindole derivatives as pharmaceutical agents Download PDFInfo
- Publication number
- CA2485909C CA2485909C CA2485909A CA2485909A CA2485909C CA 2485909 C CA2485909 C CA 2485909C CA 2485909 A CA2485909 A CA 2485909A CA 2485909 A CA2485909 A CA 2485909A CA 2485909 C CA2485909 C CA 2485909C
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- heterocyclyl
- alkyl
- aryl
- heteroaryl
- 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.)
- Expired - Lifetime
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- IVCGJOSPVGENCT-UHFFFAOYSA-N 1h-pyrrolo[2,3-f]quinoline Chemical class N1=CC=CC2=C(NC=C3)C3=CC=C21 IVCGJOSPVGENCT-UHFFFAOYSA-N 0.000 title 1
- 239000008177 pharmaceutical agent Substances 0.000 title 1
- ISZIQZCZKOFSBT-UHFFFAOYSA-N pyrrolo[2,3-g][1]benzazepine Chemical compound N1=CC=CC=C2C3=NC=CC3=CC=C21 ISZIQZCZKOFSBT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 113
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 230000000694 effects Effects 0.000 claims abstract 3
- -1 nitro, formyl Chemical group 0.000 claims 620
- 125000001072 heteroaryl group Chemical group 0.000 claims 452
- 125000000623 heterocyclic group Chemical group 0.000 claims 430
- 125000000547 substituted alkyl group Chemical group 0.000 claims 308
- 229910052739 hydrogen Inorganic materials 0.000 claims 292
- 239000001257 hydrogen Substances 0.000 claims 292
- 125000003710 aryl alkyl group Chemical group 0.000 claims 283
- 125000003107 substituted aryl group Chemical group 0.000 claims 256
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 246
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 239
- 150000002431 hydrogen Chemical class 0.000 claims 226
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 211
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 207
- 125000003118 aryl group Chemical group 0.000 claims 117
- 125000000217 alkyl group Chemical group 0.000 claims 107
- 125000004429 atom Chemical group 0.000 claims 104
- 229910052757 nitrogen Inorganic materials 0.000 claims 82
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 78
- 125000002947 alkylene group Chemical group 0.000 claims 75
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 71
- 125000005843 halogen group Chemical group 0.000 claims 69
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 60
- 125000002577 pseudohalo group Chemical group 0.000 claims 59
- 125000003545 alkoxy group Chemical group 0.000 claims 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 48
- 201000010099 disease Diseases 0.000 claims 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 43
- 125000001188 haloalkyl group Chemical group 0.000 claims 40
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 38
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 37
- 101100173726 Arabidopsis thaliana OR23 gene Proteins 0.000 claims 34
- 229910052799 carbon Inorganic materials 0.000 claims 34
- 150000001721 carbon Chemical group 0.000 claims 32
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 32
- 125000004043 oxo group Chemical group O=* 0.000 claims 31
- 229920001774 Perfluoroether Polymers 0.000 claims 30
- 241000534944 Thia Species 0.000 claims 30
- 125000003342 alkenyl group Chemical group 0.000 claims 30
- 125000003302 alkenyloxy group Chemical group 0.000 claims 30
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 30
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 30
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 30
- 125000005138 alkoxysulfonyl group Chemical group 0.000 claims 30
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 30
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 30
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims 30
- 125000003282 alkyl amino group Chemical group 0.000 claims 30
- 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims 30
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims 30
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 30
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 30
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 30
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 30
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 30
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 30
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 30
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 30
- 125000004414 alkyl thio group Chemical group 0.000 claims 30
- 125000001118 alkylidene group Chemical group 0.000 claims 30
- 125000000304 alkynyl group Chemical group 0.000 claims 30
- 125000005133 alkynyloxy group Chemical group 0.000 claims 30
- 125000004103 aminoalkyl group Chemical group 0.000 claims 30
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 30
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims 30
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims 30
- 125000005128 aryl amino alkyl group Chemical group 0.000 claims 30
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 30
- 125000001769 aryl amino group Chemical group 0.000 claims 30
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims 30
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 30
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 30
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims 30
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 30
- 125000005110 aryl thio group Chemical group 0.000 claims 30
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims 30
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 30
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 30
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 30
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 30
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims 30
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 30
- 125000004663 dialkyl amino group Chemical group 0.000 claims 30
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 30
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims 30
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 30
- 125000004986 diarylamino group Chemical group 0.000 claims 30
- 125000004992 haloalkylamino group Chemical group 0.000 claims 30
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 30
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 30
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 30
- 125000005368 heteroarylthio group Chemical group 0.000 claims 30
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 30
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 30
- 150000002825 nitriles Chemical class 0.000 claims 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 30
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 30
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims 30
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 30
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 29
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 29
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 29
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 28
- 208000035475 disorder Diseases 0.000 claims 28
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims 28
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 28
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims 27
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims 26
- 125000005106 triarylsilyl group Chemical group 0.000 claims 26
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims 25
- 239000003112 inhibitor Substances 0.000 claims 25
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims 24
- 239000005557 antagonist Substances 0.000 claims 22
- 239000000556 agonist Substances 0.000 claims 20
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 20
- 239000004031 partial agonist Substances 0.000 claims 20
- 201000001320 Atherosclerosis Diseases 0.000 claims 18
- 230000003143 atherosclerotic effect Effects 0.000 claims 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 17
- 150000007857 hydrazones Chemical class 0.000 claims 17
- 150000002466 imines Chemical class 0.000 claims 17
- 150000002923 oximes Chemical class 0.000 claims 17
- 125000000464 thioxo group Chemical group S=* 0.000 claims 17
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 16
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 16
- SJSSFUMSAFMFNM-NSHDSACASA-N (2s)-5-(diaminomethylideneamino)-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound NC(N)=NCCC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 SJSSFUMSAFMFNM-NSHDSACASA-N 0.000 claims 15
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 claims 15
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 claims 15
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 15
- 125000004104 aryloxy group Chemical group 0.000 claims 15
- 229940107161 cholesterol Drugs 0.000 claims 15
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 15
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims 15
- 125000005241 heteroarylamino group Chemical group 0.000 claims 15
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims 15
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 14
- 102000004877 Insulin Human genes 0.000 claims 14
- 108090001061 Insulin Proteins 0.000 claims 14
- 206010012601 diabetes mellitus Diseases 0.000 claims 14
- 229940125396 insulin Drugs 0.000 claims 14
- 235000012000 cholesterol Nutrition 0.000 claims 12
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 11
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 11
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims 10
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 claims 10
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 claims 10
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 10
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims 10
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims 10
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims 10
- 206010003210 Arteriosclerosis Diseases 0.000 claims 9
- 206010008635 Cholestasis Diseases 0.000 claims 9
- 208000032928 Dyslipidaemia Diseases 0.000 claims 9
- 208000017170 Lipid metabolism disease Diseases 0.000 claims 9
- 208000008589 Obesity Diseases 0.000 claims 9
- 239000013543 active substance Substances 0.000 claims 9
- 230000007870 cholestasis Effects 0.000 claims 9
- 231100000359 cholestasis Toxicity 0.000 claims 9
- 201000001421 hyperglycemia Diseases 0.000 claims 9
- 235000020824 obesity Nutrition 0.000 claims 9
- 208000011580 syndromic disease Diseases 0.000 claims 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 229910006095 SO2F Inorganic materials 0.000 claims 8
- 206010049287 Lipodystrophy acquired Diseases 0.000 claims 7
- 208000006132 lipodystrophy Diseases 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 6
- 230000015572 biosynthetic process Effects 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 claims 5
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims 5
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims 5
- 239000005541 ACE inhibitor Substances 0.000 claims 5
- ITZMJCSORYKOSI-AJNGGQMLSA-N APGPR Enterostatin Chemical compound C[C@H](N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N1[C@H](C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)CCC1 ITZMJCSORYKOSI-AJNGGQMLSA-N 0.000 claims 5
- 239000000275 Adrenocorticotropic Hormone Substances 0.000 claims 5
- 229940123413 Angiotensin II antagonist Drugs 0.000 claims 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 5
- 229940123208 Biguanide Drugs 0.000 claims 5
- 102000013585 Bombesin Human genes 0.000 claims 5
- 108010051479 Bombesin Proteins 0.000 claims 5
- 101800000414 Corticotropin Proteins 0.000 claims 5
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 claims 5
- 102000004980 Dopamine D2 Receptors Human genes 0.000 claims 5
- 108090001111 Dopamine D2 Receptors Proteins 0.000 claims 5
- 239000004131 EU approved raising agent Substances 0.000 claims 5
- 102000019432 Galanin Human genes 0.000 claims 5
- 101800002068 Galanin Proteins 0.000 claims 5
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 5
- 102000000853 LDL receptors Human genes 0.000 claims 5
- 108010001831 LDL receptors Proteins 0.000 claims 5
- 229940127470 Lipase Inhibitors Drugs 0.000 claims 5
- ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 claims 5
- 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 claims 5
- 108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 claims 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 5
- 229940100389 Sulfonylurea Drugs 0.000 claims 5
- 229940123464 Thiazolidinedione Drugs 0.000 claims 5
- 229930003779 Vitamin B12 Natural products 0.000 claims 5
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 5
- 239000012190 activator Substances 0.000 claims 5
- 239000000048 adrenergic agonist Substances 0.000 claims 5
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 5
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims 5
- 239000003529 anticholesteremic agent Substances 0.000 claims 5
- 239000003524 antilipemic agent Substances 0.000 claims 5
- 229940127218 antiplatelet drug Drugs 0.000 claims 5
- 229960000516 bezafibrate Drugs 0.000 claims 5
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 claims 5
- 150000004283 biguanides Chemical class 0.000 claims 5
- 229920000080 bile acid sequestrant Polymers 0.000 claims 5
- 229940096699 bile acid sequestrants Drugs 0.000 claims 5
- DNDCVAGJPBKION-DOPDSADYSA-N bombesin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1NC2=CC=CC=C2C=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1NC(=O)CC1)C(C)C)C1=CN=CN1 DNDCVAGJPBKION-DOPDSADYSA-N 0.000 claims 5
- 230000001906 cholesterol absorption Effects 0.000 claims 5
- 229960001214 clofibrate Drugs 0.000 claims 5
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 claims 5
- AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 claims 5
- 239000005516 coenzyme A Substances 0.000 claims 5
- 229940093530 coenzyme a Drugs 0.000 claims 5
- 229960000258 corticotropin Drugs 0.000 claims 5
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 claims 5
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 claims 5
- 229960004597 dexfenfluramine Drugs 0.000 claims 5
- 229960004890 diethylpropion Drugs 0.000 claims 5
- XXEPPPIWZFICOJ-UHFFFAOYSA-N diethylpropion Chemical compound CCN(CC)C(C)C(=O)C1=CC=CC=C1 XXEPPPIWZFICOJ-UHFFFAOYSA-N 0.000 claims 5
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 229960001582 fenfluramine Drugs 0.000 claims 5
- 229960002297 fenofibrate Drugs 0.000 claims 5
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 claims 5
- 229940125753 fibrate Drugs 0.000 claims 5
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- VNGDHNJAJJRUHC-UHFFFAOYSA-N ethyl 3-(3,4-difluorobenzoyl)-1,1-dimethyl-8-(2-phenylethylamino)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=C(F)C(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3NCCC1=CC=CC=C1 VNGDHNJAJJRUHC-UHFFFAOYSA-N 0.000 claims 1
- AAGAYUABSBAYSC-UHFFFAOYSA-N ethyl 3-(3,4-difluorobenzoyl)-1-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C(F)=C1 AAGAYUABSBAYSC-UHFFFAOYSA-N 0.000 claims 1
- OSEILIMCSUKCSZ-UHFFFAOYSA-N ethyl 3-(4-chlorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(Cl)C=C1 OSEILIMCSUKCSZ-UHFFFAOYSA-N 0.000 claims 1
- KGLPNKZEJPFLFT-UHFFFAOYSA-N ethyl 3-(4-chlorobenzoyl)-1-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(Cl)C=C1 KGLPNKZEJPFLFT-UHFFFAOYSA-N 0.000 claims 1
- HUJPSDDFRZDTTO-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(2-oxoimidazolidine-1-carbonyl)oxy-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N1CCNC1=O HUJPSDDFRZDTTO-UHFFFAOYSA-N 0.000 claims 1
- ASQPRMAURCRBQX-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(2-phenylethylcarbamoyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NCCC1=CC=CC=C1 ASQPRMAURCRBQX-UHFFFAOYSA-N 0.000 claims 1
- BUROFAQWTNKOTD-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(2-pyridin-2-ylethylcarbamoyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NCCC1=CC=CC=N1 BUROFAQWTNKOTD-UHFFFAOYSA-N 0.000 claims 1
- QNLLOZVRRZCWRK-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(4-methylpiperazine-1-carbonyl)oxy-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N1CCN(C)CC1 QNLLOZVRRZCWRK-UHFFFAOYSA-N 0.000 claims 1
- BWFZLWWAPHLWDT-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(4-pyridin-2-ylpiperazine-1-carbonyl)oxy-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N(CC1)CCN1C1=CC=CC=N1 BWFZLWWAPHLWDT-UHFFFAOYSA-N 0.000 claims 1
- UPWKXJHRIILWEH-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(methylcarbamoyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)NC)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 UPWKXJHRIILWEH-UHFFFAOYSA-N 0.000 claims 1
- TWKCGIIZVWAYHH-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(piperidine-1-carbonyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N1CCCCC1 TWKCGIIZVWAYHH-UHFFFAOYSA-N 0.000 claims 1
- JVTUMPSDGFUNGM-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(propan-2-ylcarbamoyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)NC(C)C)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 JVTUMPSDGFUNGM-UHFFFAOYSA-N 0.000 claims 1
- CIDOBUXYVNZRKP-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(pyridin-2-ylmethylcarbamoyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NCC1=CC=CC=N1 CIDOBUXYVNZRKP-UHFFFAOYSA-N 0.000 claims 1
- OAUYPJXXGGGXFU-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(pyridin-3-ylmethylcarbamoyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NCC1=CC=CN=C1 OAUYPJXXGGGXFU-UHFFFAOYSA-N 0.000 claims 1
- KLZBRGQFOCXVHN-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(pyrrolidine-1-carbonyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N1CCCC1 KLZBRGQFOCXVHN-UHFFFAOYSA-N 0.000 claims 1
- PLLCAYDTNDYTNW-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-(thiophen-2-ylmethylcarbamoyloxy)-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NCC1=CC=CS1 PLLCAYDTNDYTNW-UHFFFAOYSA-N 0.000 claims 1
- LGTCNBAEZKRPGL-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[(4-methylpiperazin-1-yl)carbamoyloxy]-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NN1CCN(C)CC1 LGTCNBAEZKRPGL-UHFFFAOYSA-N 0.000 claims 1
- MMRRFOMJSBMMRR-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[(5-methylpyrazin-2-yl)methylcarbamoyloxy]-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NCC1=CN=C(C)C=N1 MMRRFOMJSBMMRR-UHFFFAOYSA-N 0.000 claims 1
- DKJXKGWNCZIFLM-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[[propan-2-yl(pyridin-2-yl)carbamoyl]amino]-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3NC(=O)N(C(C)C)C1=CC=CC=N1 DKJXKGWNCZIFLM-UHFFFAOYSA-N 0.000 claims 1
- PPLXIFVVKZULSH-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[methyl(morpholine-4-carbonyl)amino]-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3N(C)C(=O)N1CCOCC1 PPLXIFVVKZULSH-UHFFFAOYSA-N 0.000 claims 1
- DKSALJRHNRDJRP-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[methyl(phenyl)carbamoyl]oxy-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N(C)C1=CC=CC=C1 DKSALJRHNRDJRP-UHFFFAOYSA-N 0.000 claims 1
- QOJOOCSNYYZLTM-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[methyl(pyridin-2-ylmethylcarbamoyl)amino]-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3N(C)C(=O)NCC1=CC=CC=N1 QOJOOCSNYYZLTM-UHFFFAOYSA-N 0.000 claims 1
- FWJNNYQPGOFOMS-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[methyl(pyridin-4-yl)carbamoyl]oxy-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N(C)C1=CC=NC=C1 FWJNNYQPGOFOMS-UHFFFAOYSA-N 0.000 claims 1
- WLKIJVMJWZKWIU-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[methyl(pyrrolidine-3-carbonyl)amino]-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3N(C)C(=O)C1CCNC1 WLKIJVMJWZKWIU-UHFFFAOYSA-N 0.000 claims 1
- DWEXPBVJSABFNN-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-phenoxycarbonyloxy-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)OC1=CC=CC=C1 DWEXPBVJSABFNN-UHFFFAOYSA-N 0.000 claims 1
- UHFSNYSJRIBHMJ-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-phenylmethoxycarbonyloxy-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)OCC1=CC=CC=C1 UHFSNYSJRIBHMJ-UHFFFAOYSA-N 0.000 claims 1
- MVYSSTPZWAVKFN-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 MVYSSTPZWAVKFN-UHFFFAOYSA-N 0.000 claims 1
- IRPCGFKCPJOFET-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-8-(furan-2-ylmethylcarbamoyloxy)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NCC1=CC=CO1 IRPCGFKCPJOFET-UHFFFAOYSA-N 0.000 claims 1
- GRQISRPNUMGHFH-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-8-[[2-(4-fluorophenyl)-2-oxoethyl]amino]-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3NCC(=O)C1=CC=C(F)C=C1 GRQISRPNUMGHFH-UHFFFAOYSA-N 0.000 claims 1
- ZTJPWTTWTRCCDB-UHFFFAOYSA-N ethyl 3-(4-methyl-2-phenyl-1,3-thiazole-5-carbonyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C(=C(N=1)C)SC=1C1=CC=CC=C1 ZTJPWTTWTRCCDB-UHFFFAOYSA-N 0.000 claims 1
- JUXULRDTZAKDEY-UHFFFAOYSA-N ethyl 3-(4-methyl-2-pyrazin-2-yl-1,3-thiazole-5-carbonyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C(=C(N=1)C)SC=1C1=CN=CC=N1 JUXULRDTZAKDEY-UHFFFAOYSA-N 0.000 claims 1
- GICTUKQJFWPXEG-UHFFFAOYSA-N ethyl 3-(benzylcarbamoyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)NCC1=CC=CC=C1 GICTUKQJFWPXEG-UHFFFAOYSA-N 0.000 claims 1
- GUYATGKYGRHZIA-UHFFFAOYSA-N ethyl 3-(cyclohexylmethyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1CC1CCCCC1 GUYATGKYGRHZIA-UHFFFAOYSA-N 0.000 claims 1
- FUBYCEGZHJPKAX-UHFFFAOYSA-N ethyl 3-(pyridin-2-ylmethyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1CC1=CC=CC=N1 FUBYCEGZHJPKAX-UHFFFAOYSA-N 0.000 claims 1
- YXFOAMPODGVLFJ-UHFFFAOYSA-N ethyl 3-[(3-methylsulfanylphenyl)carbamoyl]-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)NC1=CC=CC(SC)=C1 YXFOAMPODGVLFJ-UHFFFAOYSA-N 0.000 claims 1
- STKNPUAMHDWZEE-UHFFFAOYSA-N ethyl 3-[(3-phenoxyphenyl)carbamoyl]-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 STKNPUAMHDWZEE-UHFFFAOYSA-N 0.000 claims 1
- XYEJZDSHPBNNRP-UHFFFAOYSA-N ethyl 3-[(4-fluorophenyl)methylcarbamoyl]-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)NCC1=CC=C(F)C=C1 XYEJZDSHPBNNRP-UHFFFAOYSA-N 0.000 claims 1
- JKOATCIVVUFKMU-UHFFFAOYSA-N ethyl 3-[(4-phenoxyphenyl)carbamoyl]-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 JKOATCIVVUFKMU-UHFFFAOYSA-N 0.000 claims 1
- WWAORAMSISWAKU-UHFFFAOYSA-N ethyl 3-[(4-phenylphenyl)carbamoyl]-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)NC(C=C1)=CC=C1C1=CC=CC=C1 WWAORAMSISWAKU-UHFFFAOYSA-N 0.000 claims 1
- PLQLORLKAOGTCY-UHFFFAOYSA-N ethyl 3-acetyl-9-(4-methoxyphenyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(C)=O)CCC(C2=C3)=C1NC2=CC=C3C1=CC=C(OC)C=C1 PLQLORLKAOGTCY-UHFFFAOYSA-N 0.000 claims 1
- GFMZMXVRSOKMNP-UHFFFAOYSA-N ethyl 3-benzyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)=CN1CC1=CC=CC=C1 GFMZMXVRSOKMNP-UHFFFAOYSA-N 0.000 claims 1
- RUGHGUNUWAKSSF-UHFFFAOYSA-N ethyl 8-(azetidine-1-carbonyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)N1CCC1 RUGHGUNUWAKSSF-UHFFFAOYSA-N 0.000 claims 1
- IXBXIGCJRPWCTD-UHFFFAOYSA-N ethyl 8-(cyclobutylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NC1CCC1 IXBXIGCJRPWCTD-UHFFFAOYSA-N 0.000 claims 1
- MZYMVUFLKCYFDW-UHFFFAOYSA-N ethyl 8-(cyclohexylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NC1CCCCC1 MZYMVUFLKCYFDW-UHFFFAOYSA-N 0.000 claims 1
- YKZHMHVXYHUJNK-UHFFFAOYSA-N ethyl 8-(cyclopentylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NC1CCCC1 YKZHMHVXYHUJNK-UHFFFAOYSA-N 0.000 claims 1
- BPCAAGDBRPEQSD-UHFFFAOYSA-N ethyl 8-(cyclopropylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3OC(=O)NC1CC1 BPCAAGDBRPEQSD-UHFFFAOYSA-N 0.000 claims 1
- MCOZIEQOYSHFTE-UHFFFAOYSA-N ethyl 8-(dibenzylamino)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3N(CC=1C=CC=CC=1)CC1=CC=CC=C1 MCOZIEQOYSHFTE-UHFFFAOYSA-N 0.000 claims 1
- NGUNEAJQPCIJRB-UHFFFAOYSA-N ethyl 8-(diethylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)N(CC)CC)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 NGUNEAJQPCIJRB-UHFFFAOYSA-N 0.000 claims 1
- UHOMGKRAIAZBDM-UHFFFAOYSA-N ethyl 8-(dimethylcarbamoylamino)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(NC(=O)N(C)C)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 UHOMGKRAIAZBDM-UHFFFAOYSA-N 0.000 claims 1
- MHDYUXMQCYPGLO-UHFFFAOYSA-N ethyl 8-(dimethylcarbamoyloxy)-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)N(C)C)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 MHDYUXMQCYPGLO-UHFFFAOYSA-N 0.000 claims 1
- HKCIYRZBERFQIO-UHFFFAOYSA-N ethyl 8-[2-(dimethylamino)ethoxycarbonyloxy]-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)OCCN(C)C)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 HKCIYRZBERFQIO-UHFFFAOYSA-N 0.000 claims 1
- GRNNTRJDTFCQDI-UHFFFAOYSA-N ethyl 8-[2-(dimethylamino)ethylcarbamoyloxy]-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)NCCN(C)C)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 GRNNTRJDTFCQDI-UHFFFAOYSA-N 0.000 claims 1
- KQJUDCYGVZKKPE-UHFFFAOYSA-N ethyl 8-[2-chloroethyl(methyl)amino]-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(C=C2N2)N(C)CCCl)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 KQJUDCYGVZKKPE-UHFFFAOYSA-N 0.000 claims 1
- UBQOBCJRCGNFQE-UHFFFAOYSA-N ethyl 8-[cyclopropylcarbamoyl(methyl)amino]-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=CC=3)=C1NC2=CC=3N(C)C(=O)NC1CC1 UBQOBCJRCGNFQE-UHFFFAOYSA-N 0.000 claims 1
- UHWLFLRMEICOPO-UHFFFAOYSA-N ethyl 8-[di(propan-2-yl)carbamoyloxy]-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)N(C(C)C)C(C)C)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 UHWLFLRMEICOPO-UHFFFAOYSA-N 0.000 claims 1
- YAMHSBINZGAIER-UHFFFAOYSA-N ethyl 8-[dimethylcarbamoyl(methyl)amino]-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(C=C2N2)N(C)C(=O)N(C)C)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 YAMHSBINZGAIER-UHFFFAOYSA-N 0.000 claims 1
- OALNEZYHEALGPL-UHFFFAOYSA-N ethyl 8-[ethyl(propan-2-yl)carbamoyl]oxy-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=C(OC(=O)N(CC)C(C)C)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 OALNEZYHEALGPL-UHFFFAOYSA-N 0.000 claims 1
- WRPVILCEOWNTEK-UHFFFAOYSA-N ethyl 8-ethoxycarbonyloxy-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound N1C2=CC(OC(=O)OCC)=CC=C2C(C(C2)(C)C)=C1C(C(=O)OCC)=CN2C(=O)C1=CC=C(F)C=C1 WRPVILCEOWNTEK-UHFFFAOYSA-N 0.000 claims 1
- RIEACHLOMNWTCN-UHFFFAOYSA-N ethyl 9-[benzyl(dimethylcarbamoyl)amino]-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C(=O)C=2C=CC(F)=CC=2)CC(C)(C)C(C2=C3)=C1NC2=CC=C3N(C(=O)N(C)C)CC1=CC=CC=C1 RIEACHLOMNWTCN-UHFFFAOYSA-N 0.000 claims 1
- DYTPYGNJKOZSLQ-UHFFFAOYSA-N ethyl 9-fluoro-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC(F)=CC=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C=C1 DYTPYGNJKOZSLQ-UHFFFAOYSA-N 0.000 claims 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000029142 excretion Effects 0.000 claims 1
- 230000004060 metabolic process Effects 0.000 claims 1
- DTZGOPBQYUGAPL-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(4-fluorobenzoyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)N1C=C(C(=O)NCC2CC2)C(NC=2C3=CC=CC=2)=C3CC1 DTZGOPBQYUGAPL-UHFFFAOYSA-N 0.000 claims 1
- DVAXYDFDLKIZRD-UHFFFAOYSA-N n-butan-2-yl-3-(4-fluorobenzoyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)NC(C)CC)=CN1C(=O)C1=CC=C(F)C=C1 DVAXYDFDLKIZRD-UHFFFAOYSA-N 0.000 claims 1
- PEGUBJJUSIYHHK-UHFFFAOYSA-N n-cyclobutyl-3-(3,4-difluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxamide Chemical compound C1=2NC3=CC=CC=C3C=2C(C)(C)CN(C(=O)C=2C=C(F)C(F)=CC=2)C=C1C(=O)NC1CCC1 PEGUBJJUSIYHHK-UHFFFAOYSA-N 0.000 claims 1
- KXOAUGQPXPZMFG-UHFFFAOYSA-N n-cyclobutyl-3-(3,4-difluorobenzoyl)-1-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound C1=2NC3=CC=CC=C3C=2C(C)CN(C(=O)C=2C=C(F)C(F)=CC=2)C=C1C(=O)NC1CCC1 KXOAUGQPXPZMFG-UHFFFAOYSA-N 0.000 claims 1
- NDRAMBTXSQBBKG-UHFFFAOYSA-N n-cyclobutyl-3-(3,4-difluorobenzoyl)-2-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound CC1CC(C2=CC=CC=C2N2)=C2C(C(=O)NC2CCC2)=CN1C(=O)C1=CC=C(F)C(F)=C1 NDRAMBTXSQBBKG-UHFFFAOYSA-N 0.000 claims 1
- JOJYDWBTYLYXAE-UHFFFAOYSA-N n-cyclobutyl-3-(4-fluorobenzoyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)N1C=C(C(=O)NC2CCC2)C(NC=2C3=CC=CC=2)=C3CC1 JOJYDWBTYLYXAE-UHFFFAOYSA-N 0.000 claims 1
- UNIYMUKDMOFJDT-UHFFFAOYSA-N n-cyclobutyl-3-(4-fluorobenzoyl)-2-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound CC1CC(C2=CC=CC=C2N2)=C2C(C(=O)NC2CCC2)=CN1C(=O)C1=CC=C(F)C=C1 UNIYMUKDMOFJDT-UHFFFAOYSA-N 0.000 claims 1
- JMGVWFNEUGALQZ-UHFFFAOYSA-N n-cyclopentyl-3-(4-fluorobenzoyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)N1C=C(C(=O)NC2CCCC2)C(NC=2C3=CC=CC=2)=C3CC1 JMGVWFNEUGALQZ-UHFFFAOYSA-N 0.000 claims 1
- WZHGWNWHWAVNTI-UHFFFAOYSA-N n-cyclopropyl-3-(4-fluorobenzoyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound C1=CC(F)=CC=C1C(=O)N1C=C(C(=O)NC2CC2)C(NC=2C3=CC=CC=2)=C3CC1 WZHGWNWHWAVNTI-UHFFFAOYSA-N 0.000 claims 1
- NVRCQYNUBJFHBD-UHFFFAOYSA-N propan-2-yl 3-(3,4-difluorobenzoyl)-1-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OC(C)C)=CN1C(=O)C1=CC=C(F)C(F)=C1 NVRCQYNUBJFHBD-UHFFFAOYSA-N 0.000 claims 1
- DZZKBTPWXGMEJZ-UHFFFAOYSA-N propan-2-yl 3-(3,4-dimethoxyphenyl)sulfonyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C=C(C(=O)OC(C)C)C(NC=2C3=CC=CC=2)=C3CC1 DZZKBTPWXGMEJZ-UHFFFAOYSA-N 0.000 claims 1
- VHXFEDIRQIUHQI-UHFFFAOYSA-N propan-2-yl 3-(3-phenylpropanoyl)-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OC(C)C)=CN1C(=O)CCC1=CC=CC=C1 VHXFEDIRQIUHQI-UHFFFAOYSA-N 0.000 claims 1
- KZKDZPCFCDGTFW-UHFFFAOYSA-N propan-2-yl 3-(4-chlorophenyl)sulfonyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OC(C)C)=CN1S(=O)(=O)C1=CC=C(Cl)C=C1 KZKDZPCFCDGTFW-UHFFFAOYSA-N 0.000 claims 1
- NTSNKXMZNHNDTP-UHFFFAOYSA-N propan-2-yl 3-(4-methoxyphenyl)sulfonyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C=C(C(=O)OC(C)C)C(NC=2C3=CC=CC=2)=C3CC1 NTSNKXMZNHNDTP-UHFFFAOYSA-N 0.000 claims 1
- FUBAYSMZWUMYRM-UHFFFAOYSA-N propan-2-yl 3-(4-methylphenyl)sulfonyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OC(C)C)=CN1S(=O)(=O)C1=CC=C(C)C=C1 FUBAYSMZWUMYRM-UHFFFAOYSA-N 0.000 claims 1
- ONXVFTZLBVELPZ-UHFFFAOYSA-N propan-2-yl 3-[4-(trifluoromethoxy)phenyl]sulfonyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OC(C)C)=CN1S(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 ONXVFTZLBVELPZ-UHFFFAOYSA-N 0.000 claims 1
- VOGVOPWFCMDKIZ-UHFFFAOYSA-N propyl 3-(4-fluorobenzoyl)-2-methyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound CC1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCCC)=CN1C(=O)C1=CC=C(F)C=C1 VOGVOPWFCMDKIZ-UHFFFAOYSA-N 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- INASOKQDNHHMRE-UHFFFAOYSA-N turofexorate isopropyl Chemical compound C1C(C)(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OC(C)C)=CN1C(=O)C1=CC=C(F)C(F)=C1 INASOKQDNHHMRE-UHFFFAOYSA-N 0.000 claims 1
- 102000004164 orphan nuclear receptors Human genes 0.000 abstract 1
- 108090000629 orphan nuclear receptors Proteins 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38357402P | 2002-05-24 | 2002-05-24 | |
| US60/383,574 | 2002-05-24 | ||
| PCT/US2003/016767 WO2003099821A1 (en) | 2002-05-24 | 2003-05-27 | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2485909A1 CA2485909A1 (en) | 2003-12-04 |
| CA2485909C true CA2485909C (en) | 2011-02-22 |
Family
ID=29584586
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2485909A Expired - Lifetime CA2485909C (en) | 2002-05-24 | 2003-05-27 | Azepinoindole and pyridoindole derivatives as pharmaceutical agents |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7485634B2 (https=) |
| EP (1) | EP1532153B8 (https=) |
| JP (2) | JP4646293B2 (https=) |
| AT (1) | ATE547420T1 (https=) |
| AU (1) | AU2003243328C1 (https=) |
| CA (1) | CA2485909C (https=) |
| TW (1) | TWI329111B (https=) |
| WO (1) | WO2003099821A1 (https=) |
Families Citing this family (93)
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| AU2002367060A1 (en) | 2001-12-21 | 2003-07-30 | X-Ceptor Therapeutics, Inc. | Heterocyclic modulators of nuclear receptors |
| US7595311B2 (en) * | 2002-05-24 | 2009-09-29 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| DE10252667A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| FR2848452B1 (fr) * | 2002-12-12 | 2007-04-06 | Aventis Pharma Sa | Application des inhibiteurs de recapture intestinale des acides biliaires pour la prevention et le traitement de la maladie d'alzheimer |
| WO2004096802A2 (en) * | 2003-04-29 | 2004-11-11 | Oscient Pharmaceuticals | ANTIBIOTIC TETRAHYDRO-β-CARBOLINE DERIVATIVES |
| ES2427166T3 (es) | 2003-06-23 | 2013-10-29 | Ono Pharmaceutical Co., Ltd. | Compuesto heterocíclico tricíclico novedoso |
| JP4679517B2 (ja) | 2003-07-23 | 2011-04-27 | エグゼリクシス， インコーポレイテッド | 薬剤としてのアゼピン誘導体 |
| MXPA06010543A (es) * | 2004-03-15 | 2007-03-26 | Ptc Therapeutics Inc | Derivados de carbolina utiles en la inhibicion de la angiogenesis. |
| US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| US7767689B2 (en) * | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| PT1732892E (pt) * | 2004-03-26 | 2008-12-22 | Hoffmann La Roche | Tetra-hidrocarbazóis e os seus derivados |
| TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| MX2007000214A (es) | 2004-07-01 | 2007-05-10 | Asubio Pharma Co Ltd | Derivado de tienopirazol que tiene actividad inhibidora de pde 7. |
| US20060252670A1 (en) * | 2004-10-14 | 2006-11-09 | Intercept Pharmaceuticals Inc. | Method of reducing drug-induced adverse side effects in a patient |
| WO2006063709A1 (en) * | 2004-12-15 | 2006-06-22 | F.Hoffmann-La Roche Ag | Bi- and tricyclic substituted phenyl methanones as glycine transporter i (glyt-1) inhibitors for the treatment of alzheimer’s disease |
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