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
Links
- 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
- 239000002319 fibrinogen receptor antagonist Substances 0.000 claims 5
- 230000002496 gastric effect Effects 0.000 claims 5
- 239000003382 histamine H3 receptor agonist Substances 0.000 claims 5
- 239000003395 histamine H3 receptor antagonist Substances 0.000 claims 5
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 5
- 239000000411 inducer Substances 0.000 claims 5
- 229960000299 mazindol Drugs 0.000 claims 5
- SLZIZIJTGAYEKK-CIJSCKBQSA-N molport-023-220-247 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)CN)[C@@H](C)O)C1=CNC=N1 SLZIZIJTGAYEKK-CIJSCKBQSA-N 0.000 claims 5
- 229960003966 nicotinamide Drugs 0.000 claims 5
- 235000005152 nicotinamide Nutrition 0.000 claims 5
- 239000011570 nicotinamide Substances 0.000 claims 5
- 229960003512 nicotinic acid Drugs 0.000 claims 5
- 235000001968 nicotinic acid Nutrition 0.000 claims 5
- 239000011664 nicotinic acid Substances 0.000 claims 5
- 229960003562 phentermine Drugs 0.000 claims 5
- 229960000395 phenylpropanolamine Drugs 0.000 claims 5
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 claims 5
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 5
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 5
- 229960003611 pramlintide Drugs 0.000 claims 5
- 108010029667 pramlintide Proteins 0.000 claims 5
- NRKVKVQDUCJPIZ-MKAGXXMWSA-N pramlintide acetate Chemical compound C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCCCN)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 NRKVKVQDUCJPIZ-MKAGXXMWSA-N 0.000 claims 5
- 229960002847 prasterone Drugs 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims 5
- 229960003912 probucol Drugs 0.000 claims 5
- 108010070701 procolipase Proteins 0.000 claims 5
- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 claims 5
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims 5
- 229960004622 raloxifene Drugs 0.000 claims 5
- 239000000018 receptor agonist Substances 0.000 claims 5
- 229940044601 receptor agonist Drugs 0.000 claims 5
- 239000002464 receptor antagonist Substances 0.000 claims 5
- 229940044551 receptor antagonist Drugs 0.000 claims 5
- 239000003488 releasing hormone Substances 0.000 claims 5
- 229960004425 sibutramine Drugs 0.000 claims 5
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- 150000001467 thiazolidinediones Chemical class 0.000 claims 5
- 235000019163 vitamin B12 Nutrition 0.000 claims 5
- 239000011715 vitamin B12 Substances 0.000 claims 5
- 235000019158 vitamin B6 Nutrition 0.000 claims 5
- 239000011726 vitamin B6 Substances 0.000 claims 5
- 229940011671 vitamin b6 Drugs 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 208000032382 Ischaemic stroke Diseases 0.000 claims 3
- 208000034493 Mucous membrane disease Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 102000003797 Neuropeptides Human genes 0.000 claims 3
- 108090000189 Neuropeptides Proteins 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims 3
- 229930003268 Vitamin C Natural products 0.000 claims 3
- 229930003427 Vitamin E Natural products 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 206010000496 acne Diseases 0.000 claims 3
- 230000037365 barrier function of the epidermis Effects 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 201000001883 cholelithiasis Diseases 0.000 claims 3
- 230000004069 differentiation Effects 0.000 claims 3
- 210000002615 epidermis Anatomy 0.000 claims 3
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 claims 3
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims 3
- 208000026278 immune system disease Diseases 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 150000002632 lipids Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 210000004400 mucous membrane Anatomy 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 230000035755 proliferation Effects 0.000 claims 3
- 210000003491 skin Anatomy 0.000 claims 3
- 235000019154 vitamin C Nutrition 0.000 claims 3
- 239000011718 vitamin C Substances 0.000 claims 3
- 235000019165 vitamin E Nutrition 0.000 claims 3
- 239000011709 vitamin E Substances 0.000 claims 3
- 229940046009 vitamin E Drugs 0.000 claims 3
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 2
- 102100038495 Bile acid receptor Human genes 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims 2
- 102000016267 Leptin Human genes 0.000 claims 2
- 108010092277 Leptin Proteins 0.000 claims 2
- 101710151321 Melanostatin Proteins 0.000 claims 2
- 102400000064 Neuropeptide Y Human genes 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 claims 2
- 239000003963 antioxidant agent Substances 0.000 claims 2
- 230000003078 antioxidant effect Effects 0.000 claims 2
- 235000006708 antioxidants Nutrition 0.000 claims 2
- 239000003613 bile acid Substances 0.000 claims 2
- 229940121360 farnesoid X receptor (fxr) agonists Drugs 0.000 claims 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 claims 2
- 229940039781 leptin Drugs 0.000 claims 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 claims 2
- 229940088594 vitamin Drugs 0.000 claims 2
- 229930003231 vitamin Natural products 0.000 claims 2
- 235000013343 vitamin Nutrition 0.000 claims 2
- 239000011782 vitamin Substances 0.000 claims 2
- AUESVFAJZOFHTF-UHFFFAOYSA-N (3,4-difluorophenyl)-(1-phenyl-1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1C(C=2C=CC=CC=2)C(NC=2C3=CC=CC=2)=C3CC1 AUESVFAJZOFHTF-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims 1
- CEIIXEMKOHBQNY-UHFFFAOYSA-N 3-(4-fluorobenzoyl)-n-propyl-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxamide Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)NCCC)=CN1C(=O)C1=CC=C(F)C=C1 CEIIXEMKOHBQNY-UHFFFAOYSA-N 0.000 claims 1
- KNSXXDSWCVMPRN-UHFFFAOYSA-N 5-o-ethyl 3-o-phenyl 8-fluoro-2,6-dihydro-1h-azepino[4,5-b]indole-3,5-dicarboxylate Chemical compound C1CC(C2=CC=C(F)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)OC1=CC=CC=C1 KNSXXDSWCVMPRN-UHFFFAOYSA-N 0.000 claims 1
- CFSQPTLCAXPDPO-UHFFFAOYSA-N 5-o-ethyl 3-o-phenyl 8-methoxy-2,6-dihydro-1h-azepino[4,5-b]indole-3,5-dicarboxylate Chemical compound C1CC(C2=CC=C(OC)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)OC1=CC=CC=C1 CFSQPTLCAXPDPO-UHFFFAOYSA-N 0.000 claims 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- SWQZJUANVCKBFV-UHFFFAOYSA-N [5-ethoxycarbonyl-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indol-8-yl] morpholine-4-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)N1CCOCC1 SWQZJUANVCKBFV-UHFFFAOYSA-N 0.000 claims 1
- 230000009102 absorption Effects 0.000 claims 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- OCPFQRLBOLXNMY-UHFFFAOYSA-N diethyl 3-acetyl-8-bromo-2,6-dihydro-1h-azepino[4,5-b]indole-2,5-dicarboxylate Chemical compound CCOC(=O)C1=CN(C(C)=O)C(C(=O)OCC)CC2=C1NC1=CC(Br)=CC=C21 OCPFQRLBOLXNMY-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZQWWOCUVTNHLSR-UHFFFAOYSA-N ethyl 1,1,3,6-tetramethyl-2h-azepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CN(C)CC(C)(C)C2=C1N(C)C1=CC=CC=C21 ZQWWOCUVTNHLSR-UHFFFAOYSA-N 0.000 claims 1
- QGICDOSNYPJQFR-UHFFFAOYSA-N ethyl 1,1-dimethyl-3,6-dihydro-2h-azepino[4,5-b]indole-5-carboxylate Chemical compound CCOC(=O)C1=CNCC(C)(C)C2=C1NC1=CC=CC=C21 QGICDOSNYPJQFR-UHFFFAOYSA-N 0.000 claims 1
- SWBBGOFVIZWEDG-UHFFFAOYSA-N ethyl 2-(3,4-difluorobenzoyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-1-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)N1C(=O)C1=CC=C(F)C(F)=C1 SWBBGOFVIZWEDG-UHFFFAOYSA-N 0.000 claims 1
- RRDKHFOZHUBLDZ-UHFFFAOYSA-N ethyl 2-(3,4-difluorobenzoyl)-4,4-dimethyl-3,9-dihydro-1h-pyrido[3,4-b]indole-1-carboxylate Chemical compound C1C(C)(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OCC)N1C(=O)C1=CC=C(F)C(F)=C1 RRDKHFOZHUBLDZ-UHFFFAOYSA-N 0.000 claims 1
- PPVVIRUYTMITTI-UHFFFAOYSA-N ethyl 2-(4-fluorobenzoyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-1-carboxylate Chemical compound C1CC(C2=CC=CC=C2N2)=C2C(C(=O)OCC)N1C(=O)C1=CC=C(F)C=C1 PPVVIRUYTMITTI-UHFFFAOYSA-N 0.000 claims 1
- PJARXMRMLDNQBT-UHFFFAOYSA-N ethyl 2-(4-fluorobenzoyl)-4,4-dimethyl-3,9-dihydro-1h-pyrido[3,4-b]indole-1-carboxylate Chemical compound C1C(C)(C)C(C2=CC=CC=C2N2)=C2C(C(=O)OCC)N1C(=O)C1=CC=C(F)C=C1 PJARXMRMLDNQBT-UHFFFAOYSA-N 0.000 claims 1
- FDIDYCIGQURPAF-UHFFFAOYSA-N ethyl 3-(1,3-benzodioxole-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)C1=CC=C(OCO2)C2=C1 FDIDYCIGQURPAF-UHFFFAOYSA-N 0.000 claims 1
- JSEUUQRQKYJVRN-UHFFFAOYSA-N ethyl 3-(1,3-benzodioxole-5-carbonyl)-8-methoxy-2,6-dihydro-1h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1CC(C2=CC=C(OC)C=C2N2)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(OCO2)C2=C1 JSEUUQRQKYJVRN-UHFFFAOYSA-N 0.000 claims 1
- ISPUZURJAHGWJJ-UHFFFAOYSA-N ethyl 3-(2,3-dihydro-1,4-benzodioxine-6-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)C1=CC=C(OCCO2)C2=C1 ISPUZURJAHGWJJ-UHFFFAOYSA-N 0.000 claims 1
- CDRAVQNIYJLWDD-UHFFFAOYSA-N ethyl 3-(2,3-dihydro-1h-inden-5-ylcarbamoyl)-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=C(CCC2)C2=C1 CDRAVQNIYJLWDD-UHFFFAOYSA-N 0.000 claims 1
- FVBONAMGCJJBLK-UHFFFAOYSA-N ethyl 3-(2-phenyl-1,3-thiazole-4-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(N=1)=CSC=1C1=CC=CC=C1 FVBONAMGCJJBLK-UHFFFAOYSA-N 0.000 claims 1
- QYTTYQWZAOMAOI-UHFFFAOYSA-N ethyl 3-(2-thiophen-2-yl-1,3-thiazole-4-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(N=1)=CSC=1C1=CC=CS1 QYTTYQWZAOMAOI-UHFFFAOYSA-N 0.000 claims 1
- YCLRYOIIPVEBMX-UHFFFAOYSA-N ethyl 3-(3,4-difluorobenzoyl)-1,1,6-trimethyl-2h-azepino[4,5-b]indole-5-carboxylate Chemical compound C1C(C)(C)C(C2=CC=CC=C2N2C)=C2C(C(=O)OCC)=CN1C(=O)C1=CC=C(F)C(F)=C1 YCLRYOIIPVEBMX-UHFFFAOYSA-N 0.000 claims 1
- NVFAURZVYMEWBH-UHFFFAOYSA-N ethyl 3-(3,4-difluorobenzoyl)-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(F)C(F)=C1 NVFAURZVYMEWBH-UHFFFAOYSA-N 0.000 claims 1
- 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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]
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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 (enExample) |
| EP (1) | EP1532153B8 (enExample) |
| JP (2) | JP4646293B2 (enExample) |
| AT (1) | ATE547420T1 (enExample) |
| AU (1) | AU2003243328C1 (enExample) |
| CA (1) | CA2485909C (enExample) |
| TW (1) | TWI329111B (enExample) |
| WO (1) | WO2003099821A1 (enExample) |
Families Citing this family (93)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU2004234405A1 (en) * | 2003-04-29 | 2004-11-11 | Arqule, Inc. | Antibiotic tetrahydro-beta-carboline derivatives |
| US7872133B2 (en) | 2003-06-23 | 2011-01-18 | Ono Pharmaceutical Co., Ltd. | Tricyclic heterocycle compound |
| KR20060052867A (ko) * | 2003-07-23 | 2006-05-19 | 엑셀리시스, 인코포레이티드 | 약제로서의 아제핀 유도체 |
| EA201200555A1 (ru) * | 2004-03-15 | 2013-01-30 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Производные карболина, полезные в ингибировании ангиогенеза |
| US7767689B2 (en) * | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
| US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
| AU2005225524B2 (en) * | 2004-03-26 | 2007-11-22 | F. Hoffmann-La Roche Ag | Tetrahydrocarbazoles and derivatives |
| TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| PT1775298E (pt) | 2004-07-01 | 2013-06-12 | Daiichi Sankyo Co Ltd | Derivado de tienopirazol com atividade inibidora da pde 7 |
| US20060252670A1 (en) * | 2004-10-14 | 2006-11-09 | Intercept Pharmaceuticals Inc. | Method of reducing drug-induced adverse side effects in a patient |
| ES2338139T3 (es) * | 2004-12-15 | 2010-05-04 | F. Hoffmann-La Roche Ag | Fenil-metanonas bi- y triciclicas sustituidas como inhibidores del transportador de la glicina i (glyt-1) para el tratamiento de la enfermedad de alzheimer. |
| PT1829874E (pt) | 2004-12-22 | 2014-04-10 | Ono Pharmaceutical Co | Composto tricíclico e sua utilização |
| US20100113502A1 (en) * | 2005-03-22 | 2010-05-06 | Astrazeneca Ab | Novel Tetrahydro-1H-Pyrido[4,3-b] Indole Derivatives as CB1 Receptor Ligands |
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| US20080207594A1 (en) | 2005-05-04 | 2008-08-28 | Davelogen Aktiengesellschaft | Use of Gsk-3 Inhibitors for Preventing and Treating Pancreatic Autoimmune Disorders |
| AU2006325815B2 (en) * | 2005-12-15 | 2012-07-05 | Exelixis, Inc. | Azepinoindole derivatives as pharmaceutical agents |
| WO2007082808A2 (en) | 2006-01-18 | 2007-07-26 | F. Hoffmann-La Roche Ag | Thiazoles as 11 beta-hsd1 inhibitors |
| WO2008024390A2 (en) | 2006-08-24 | 2008-02-28 | Novartis Ag | 2- (pyrazin-2-yl) -thiazole and 2- (1h-pyraz0l-3-yl) -thiazole derivatives as well as related compounds as stearoyl-coa desaturase (scd) inhibitors for the treatment of metabolic, cardiovascular and other disorders |
| WO2008036021A1 (en) * | 2006-09-20 | 2008-03-27 | Astrazeneca Ab | Tetrahydro-lh-pyrido [3,4 -b] indole derivatives as cbl receptor ligands |
| WO2008036022A1 (en) * | 2006-09-20 | 2008-03-27 | Astrazeneca Ab | Tetrahydro-lh-pyrido[3,4-b] indole derivatives as cb1 receptor ligands |
| US8236835B2 (en) | 2006-09-22 | 2012-08-07 | Novartis Ag | Heterocyclic inhibitors of stearoyl-CoA desaturase |
| JP2010513403A (ja) | 2006-12-20 | 2010-04-30 | ノバルティス アーゲー | Ｓｃｄ阻害剤としての２−置換５員ヘテロ環 |
| WO2008103470A2 (en) | 2007-02-21 | 2008-08-28 | Trustees Of Columbia University In The City Of New York | Oncogenic-ras-signal dependent lethal compounds |
| DE102007009235A1 (de) * | 2007-02-22 | 2008-09-18 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| US20080300235A1 (en) * | 2007-06-01 | 2008-12-04 | Wyeth | FXR Agonists for Reducing LOX-1 Expression |
| US20080299118A1 (en) * | 2007-06-01 | 2008-12-04 | Wyeth | FXR Agonists for the Treatment of Malignancies |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| US20090163474A1 (en) * | 2007-10-19 | 2009-06-25 | Wyeth | FXR Agonists for the Treatment of Nonalcoholic Fatty Liver and Cholesterol Gallstone Diseases |
| JP2011505373A (ja) | 2007-11-30 | 2011-02-24 | ビオタ サイエンティフィック マネージメント ピーティーワイ リミテッド | 抗菌剤としての２環式ｐｐａｔ阻害剤 |
| US20090215748A1 (en) * | 2007-12-20 | 2009-08-27 | Wyeth | FXR agonists for treating vitamin D associated diseases |
| ES2523580T3 (es) * | 2008-01-11 | 2014-11-27 | Albany Molecular Research, Inc. | Piridoindoles substituidos con (1-Azinona) |
| CL2009000731A1 (es) * | 2008-03-27 | 2009-05-15 | Gruenenthal Gmbh | Compuestos derivados de ciclohexano espirociclicos sustituidos, composicion farmaceutica que contiene a dicho compuesto y su uso como moduladores del receptor de opioides µ y el receptor orl-1 para tratar el dolor, ansiedad, depresion, epilepsia, alzheimer, abuso de alcohol, hipertension, anorexia, obesidad y diarrea. |
| US8357705B2 (en) * | 2008-03-27 | 2013-01-22 | Gruenenthal Gmbh | Substituted cyclohexyldiamines |
| ES2694103T3 (es) | 2008-03-27 | 2018-12-18 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| JP5599774B2 (ja) * | 2008-03-27 | 2014-10-01 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ヒドロキシメチルシクロヘキシルアミン類 |
| PL2257526T3 (pl) * | 2008-03-27 | 2012-05-31 | Gruenenthal Gmbh | Pochodne spiro (5.5) undekanu |
| WO2010036362A1 (en) * | 2008-09-26 | 2010-04-01 | Wyeth | 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate nuclear receptor inhibitors |
| CA2738769C (en) * | 2008-09-29 | 2016-02-09 | Cadila Pharmaceuticals Ltd. | Farnesoid-x-receptor antagonist as a vaccine adjuvant |
| AR074797A1 (es) * | 2008-10-10 | 2011-02-16 | Japan Tobacco Inc | Compuesto de fluoreno , composiciones farmaceuticas , inhibidores de pdhk y pdhk2 , metodos de tratamiento , usos de los mismos y kit comercial |
| AR073924A1 (es) * | 2008-10-31 | 2010-12-09 | Medivation Technologies Inc | Azepino[4, 5-b]indoles, una composicion farmaceutica y kits que los comprenden y su uso en la modulacion de un receptor de histamina. |
| TW201028414A (en) * | 2009-01-16 | 2010-08-01 | Merck Sharp & Dohme | Oxadiazole beta carboline derivatives as antidiabetic compounds |
| CN102802623A (zh) * | 2009-04-20 | 2012-11-28 | 人类健康研究所 | 含有1，3，4-恶二唑衍生物的化合物、组合物和方法 |
| US8697662B2 (en) | 2009-05-27 | 2014-04-15 | Ptc Therapeutics, Inc. | Methods for treating Kaposi sarcoma |
| WO2010138685A1 (en) | 2009-05-27 | 2010-12-02 | Ptc Therapeutics, Inc. | Methods for treating prostate conditions |
| ES2826950T3 (es) | 2009-05-27 | 2021-05-19 | Ptc Therapeutics Inc | Métodos para tratar cáncer y afecciones no neoplásicas |
| WO2010138644A1 (en) | 2009-05-27 | 2010-12-02 | Ptc Therapeutics, Inc. | Processes for the preparation of substituted tetrahydro beta-carbolines |
| US9073925B2 (en) | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| JP2012532144A (ja) * | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| US8618299B2 (en) | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| WO2011003007A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| JP6033085B2 (ja) | 2009-12-22 | 2016-11-30 | セファロン、インク． | 三環式誘導体ならびにそれらの医薬用途および組成物 |
| WO2011103430A1 (en) | 2010-02-19 | 2011-08-25 | Medivation Technologies, Inc. | Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| DK2558446T5 (da) | 2010-04-16 | 2019-12-09 | Ac Immune Sa | Nye forbindelser til behandling af sygdomme associerede med amyloid- eller amyloidlignende proteiner |
| US8933024B2 (en) | 2010-06-18 | 2015-01-13 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| WO2012112963A1 (en) * | 2011-02-18 | 2012-08-23 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| ES2587856T3 (es) | 2011-03-18 | 2016-10-27 | Ono Pharmaceutical Co., Ltd. | Derivado de tetrahidrocarbolina |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2831074B1 (en) * | 2012-03-29 | 2016-09-14 | Boehringer Ingelheim International GmbH | Novel pyrazolopyrimidines as metabotropic glutamate 5 receptor antagonists for the treatment of psychiatric diseases |
| WO2013151982A1 (en) | 2012-04-03 | 2013-10-10 | Arena Pharmaceuticals, Inc. | Methods and compounds useful in treating pruritus, and methods for identifying such compounds |
| US10092574B2 (en) | 2012-09-26 | 2018-10-09 | Valorisation-Recherche, Limited Partnership | Inhibitors of polynucleotide repeat-associated RNA foci and uses thereof |
| KR101571590B1 (ko) * | 2012-11-21 | 2015-11-25 | 주식회사 두산 | 유기 화합물 및 이를 이용하는 유기 전계 발광 소자 |
| PL2975028T3 (pl) | 2013-03-15 | 2018-10-31 | Japan Tobacco, Inc. | Związek pirazoloamidowy i jego zastosowania medyczne |
| UY35590A (es) | 2013-05-28 | 2014-11-28 | Astrazeneca Ab | Nuevos compuestos para el tratamiento del cáncer |
| WO2015138986A1 (en) * | 2014-03-13 | 2015-09-17 | Salk Institute For Biological Studies | Fxr agonists and methods for making and using |
| US10077268B2 (en) | 2014-03-13 | 2018-09-18 | Salk Institute For Biological Studies | FXR agonists and methods for making and using |
| US10301268B2 (en) | 2014-03-13 | 2019-05-28 | The Salk Institute For Biological Studies | Analogs of fexaramine and methods of making and using |
| ES2819448T3 (es) | 2014-12-18 | 2021-04-16 | Hoffmann La Roche | Tetrahidro-pirido[3,4-b]indoles como moduladores del receptor de estrógenos y usos de los mismos |
| EP3715348A1 (en) * | 2015-03-26 | 2020-09-30 | Akarna Therapeutics, Ltd. | Fused bicyclic compounds for the treatment of disease |
| BR112018009960A2 (pt) | 2015-11-16 | 2018-11-13 | Dana Farber Cancer Inst Inc | compostos e métodos para tratar sarcomas sinoviais |
| WO2017143134A1 (en) * | 2016-02-19 | 2017-08-24 | Alios Biopharma, Inc. | Fxr modulators and methods of their use |
| KR20190036549A (ko) | 2016-07-29 | 2019-04-04 | 니뽄 다바코 산교 가부시키가이샤 | 피라졸-아미드 화합물의 제조 방법 |
| US12343337B2 (en) | 2016-09-29 | 2025-07-01 | The Regents Of The University Of California | Compounds for increasing neural plasticity |
| CN106822114B (zh) * | 2016-12-12 | 2020-08-07 | 中国科学院西北高原生物研究所 | Mtca在制备降血糖或降血脂的药物中的用途 |
| KR20200035292A (ko) | 2017-08-01 | 2020-04-02 | 피티씨 테라퓨틱스, 인크. | 혈액 암 치료에 사용하기 위한 dhodh 억제제 |
| US20190357853A1 (en) * | 2018-05-24 | 2019-11-28 | Lizheng Shi | Diabetes risk engine and methods thereof for predicting diabetes progression and mortality |
| CR20230409A (es) | 2018-06-21 | 2023-09-25 | Hoffmann La Roche | Formas sólidas de 3-((1r,3r)-1-(2,6-difluoro-4-((1-(3-fluoropropil)azetidin-3-il)amino)fenil)-3-(metil-1,3,4,9-tetrahidro-2h-pirido[3,4-b]indol-2-il)-2,2-difluoropropan-1-ol y procesos para preparar compuestos tricíclicos fusionados que comprenden un resto fenilo o piridinilo sustituido, incluidos métodos para su uso (divisional expediente 2020-0621) |
| CN113677666A (zh) | 2019-02-15 | 2021-11-19 | 百时美施贵宝公司 | 作为类法尼醇x受体调节剂的经取代的双环化合物 |
| AU2020221371A1 (en) | 2019-02-15 | 2021-10-07 | Bristol-Myers Squibb Company | Substituted amide compounds useful as farnesoid x receptor modulators |
| EA202192275A1 (ru) | 2019-02-15 | 2021-11-03 | Бристол-Маерс Сквибб Компани | Замещенные амидные соединения, полезные в качестве модуляторов фарнезоидного x-рецептора |
| AR118050A1 (es) | 2019-02-15 | 2021-09-15 | Bristol Myers Squibb Co | Compuestos bicíclicos sustituidos como moduladores del receptor farnesoide x |
| EP3931189B1 (en) | 2019-02-27 | 2025-12-24 | The Regents Of The University Of California | Azepino-indoles and other heterocycles for treating brain disorders |
| CN114530589B (zh) * | 2020-11-23 | 2023-10-17 | 宁德时代新能源科技股份有限公司 | 锂金属负极、其制备方法及其相关的锂金属电池和装置 |
| WO2023114313A1 (en) | 2021-12-15 | 2023-06-22 | Delix Therapeutics, Inc. | Phenoxy and benzyloxy substituted psychoplastogens and uses thereof |
| CN120917021A (zh) * | 2023-03-15 | 2025-11-07 | 纽脑泰智有限公司 | 用于预防或治疗神经退行性疾病的包含新型吡啶并吲哚衍生物化合物作为活性成分的组合物 |
| WO2025128103A1 (en) * | 2023-12-14 | 2025-06-19 | Boulanger Willam Allen | Pharmaceutical intermediates and methods for preparing the same in the synthesis of 18-methoxycoronaridine and congeners and derivatives thereof |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH445512A (de) * | 1964-12-03 | 1967-10-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen Indolderivaten |
| GR35044B (el) | 1966-05-10 | 1968-07-31 | The Upjohn Company | Μεθοδος παρασκευης οργανικων ενωσεων. |
| FR2455039A1 (fr) * | 1979-04-26 | 1980-11-21 | Synthelabo | Pyrimido et imidazo-pyrido-indole-diones et leur application en therapeutique |
| US4362739A (en) * | 1981-05-04 | 1982-12-07 | S.A. Omnichem | Pyrrolo(2,3-d)carbazole derivatives, compositions and use |
| LU85894A1 (fr) * | 1985-05-10 | 1986-12-05 | Omnichem Sa | Derives de 1,2,3,4,5,6-hexahydro-azepino (4,5-b) indole leur preparation,composes intermediaires,et leur application en therapeutique |
| HU198012B (en) * | 1987-07-03 | 1989-07-28 | Richter Gedeon Vegyeszet | Process for producing cyclic amino-acid derivatives and pharmaceutical compositions containing them |
| EP0357122A3 (en) | 1988-08-29 | 1991-10-23 | Duphar International Research B.V | Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties |
| US5403851A (en) | 1994-04-05 | 1995-04-04 | Interneuron Pharmaceuticals, Inc. | Substituted tryptamines, phenalkylamines and related compounds |
| CZ358598A3 (cs) * | 1996-05-10 | 1999-03-17 | Icos Corporation | Karbolinové deriváty |
| DE69904595T2 (de) * | 1998-06-12 | 2003-11-27 | Societe De Conseils De Recherches Et D'applications Scientifiques S.A., Paris | Betacarbolinverbindungen |
| WO2000015639A1 (en) * | 1998-09-16 | 2000-03-23 | Icos Corporation | Carboline derivatives as cgmp phosphodiesterase inhibitors |
| US6544984B1 (en) | 1999-01-27 | 2003-04-08 | American Cyanamid Company | 2,3,4,5-tetrahydro-1H-(1,4)benzodiazepine-3-hydroxamic acids |
| US7030109B2 (en) | 1999-07-19 | 2006-04-18 | Pharmacia & Upjohn Company | 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| MY122278A (en) | 1999-07-19 | 2006-04-29 | Upjohn Co | 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| FR2796644B1 (fr) | 1999-07-23 | 2001-09-07 | Adir | Nouveaux derives de beta-carboline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2799757B1 (fr) | 1999-10-15 | 2001-12-14 | Adir | Nouveaux derives polycycliques azaindoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1319004A2 (en) | 2000-09-20 | 2003-06-18 | PHARMACIA & UPJOHN COMPANY | Substituted azepino[4,5-b]indole derivatives |
| CA2441792C (en) | 2001-04-25 | 2010-08-03 | Lilly Icos Llc | Carboline derivatives as inhibitors of phosphodiesterase 5 (pdes) for the treatment of cardiovascular diseases and erectile dysfunction |
| US6953787B2 (en) | 2002-04-12 | 2005-10-11 | Arena Pharmaceuticals, Inc. | 5HT2C receptor modulators |
-
2003
- 2003-05-23 TW TW092114049A patent/TWI329111B/zh not_active IP Right Cessation
- 2003-05-27 WO PCT/US2003/016767 patent/WO2003099821A1/en not_active Ceased
- 2003-05-27 AU AU2003243328A patent/AU2003243328C1/en not_active Expired
- 2003-05-27 US US10/447,302 patent/US7485634B2/en not_active Expired - Lifetime
- 2003-05-27 CA CA2485909A patent/CA2485909C/en not_active Expired - Lifetime
- 2003-05-27 EP EP03755523A patent/EP1532153B8/en not_active Expired - Lifetime
- 2003-05-27 JP JP2004507478A patent/JP4646293B2/ja not_active Expired - Fee Related
- 2003-05-27 AT AT03755523T patent/ATE547420T1/de active
-
2009
- 2009-01-29 US US12/362,269 patent/US8133992B2/en not_active Expired - Fee Related
-
2010
- 2010-06-14 JP JP2010135620A patent/JP2010229148A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005531585A (ja) | 2005-10-20 |
| EP1532153B1 (en) | 2012-02-29 |
| JP4646293B2 (ja) | 2011-03-09 |
| AU2003243328B2 (en) | 2010-05-20 |
| EP1532153A1 (en) | 2005-05-25 |
| AU2003243328A1 (en) | 2003-12-12 |
| AU2003243328C1 (en) | 2010-10-21 |
| US20040023947A1 (en) | 2004-02-05 |
| TWI329111B (en) | 2010-08-21 |
| ATE547420T1 (de) | 2012-03-15 |
| US8133992B2 (en) | 2012-03-13 |
| TW200307684A (en) | 2003-12-16 |
| WO2003099821A1 (en) | 2003-12-04 |
| US20090326218A1 (en) | 2009-12-31 |
| EP1532153B8 (en) | 2012-04-11 |
| CA2485909A1 (en) | 2003-12-04 |
| US7485634B2 (en) | 2009-02-03 |
| JP2010229148A (ja) | 2010-10-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2485909C (en) | Azepinoindole and pyridoindole derivatives as pharmaceutical agents | |
| CA2555279C (en) | Azepinoindole derivatives as pharmaceutical agents | |
| CA2532798C (en) | Azepine derivatives as pharmaceutical agents | |
| AU2006325815B2 (en) | Azepinoindole derivatives as pharmaceutical agents | |
| JP2005531585A5 (enExample) | ||
| MXPA06006140A (es) | Derivados de azepinoindol como agentes farmaceuticos | |
| MXPA06000875A (en) | Azepine derivatives as pharmaceutical agents | |
| HK1166982A (en) | Azepinoindole derivatives as pharmaceutical agents | |
| MX2008007811A (en) | Azepinoindole derivatives as pharmaceutical agents |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230529 |