JP2005531585A5 - - Google Patents

Info

Publication number

JP2005531585A5

JP2005531585A5 JP2004507478A JP2004507478A JP2005531585A5 JP 2005531585 A5 JP2005531585 A5 JP 2005531585A5 JP 2004507478 A JP2004507478 A JP 2004507478A JP 2004507478 A JP2004507478 A JP 2004507478A JP 2005531585 A5 JP2005531585 A5 JP 2005531585A5

Authority

JP

Japan

Prior art keywords

optionally substituted

alkyl

heteroaryl

aryl

heterocyclyl

Prior art date

2003-05-27

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.)

Granted

Links

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• -1 enol esters Chemical class 0.000 claims description 452
• 125000001072 heteroaryl group Chemical group 0.000 claims description 303
• 125000000623 heterocyclic group Chemical group 0.000 claims description 300
• 229910052739 hydrogen Inorganic materials 0.000 claims description 272
• 239000001257 hydrogen Substances 0.000 claims description 271
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 248
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 195
• 125000003107 substituted aryl group Chemical group 0.000 claims description 187
• 150000002431 hydrogen Chemical class 0.000 claims description 178
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 171
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 154
• 150000001875 compounds Chemical class 0.000 claims description 149
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 144
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 143
• 125000000217 alkyl group Chemical group 0.000 claims description 139
• 125000003118 aryl group Chemical group 0.000 claims description 111
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 104
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 89
• 125000004429 atom Chemical group 0.000 claims description 72
• 125000005843 halogen group Chemical group 0.000 claims description 66
• 229910052757 nitrogen Inorganic materials 0.000 claims description 64
• 239000000203 mixture Substances 0.000 claims description 63
• 201000010099 disease Diseases 0.000 claims description 59
• 125000002947 alkylene group Chemical group 0.000 claims description 57
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 51
• 239000008194 pharmaceutical composition Substances 0.000 claims description 49
• 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 description 48
• 125000002577 pseudohalo group Chemical group 0.000 claims description 48
• 125000003545 alkoxy group Chemical group 0.000 claims description 46
• 208000035475 disorder Diseases 0.000 claims description 43
• 108020005497 Nuclear hormone receptor Proteins 0.000 claims description 42
• 108020004017 nuclear receptors Proteins 0.000 claims description 40
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 38
• 102100038495 Bile acid receptor Human genes 0.000 claims description 37
• 125000004432 carbon atom Chemical group C* 0.000 claims description 37
• 230000000694 effects Effects 0.000 claims description 35
• 125000001188 haloalkyl group Chemical group 0.000 claims description 35
• NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 34
• 101000603876 Homo sapiens Bile acid receptor Proteins 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 229910052799 carbon Inorganic materials 0.000 claims description 31
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 29
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 28
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 27
• 125000000304 alkynyl group Chemical group 0.000 claims description 27
• NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 23
• 150000001721 carbon Chemical group 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 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 description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 125000004043 oxo group Chemical group O=* 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 21
• 125000006684 polyhaloalkyl group Polymers 0.000 claims description 21
• 102000005962 receptors Human genes 0.000 claims description 21
• 108020003175 receptors Proteins 0.000 claims description 21
• 208000024891 symptom Diseases 0.000 claims description 21
• 125000001118 alkylidene group Chemical group 0.000 claims description 20
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
• 150000002084 enol ethers Chemical class 0.000 claims description 20
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 19
• 125000004414 alkyl thio group Chemical group 0.000 claims description 19
• 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 19
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 19
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 19
• 125000005110 aryl thio group Chemical group 0.000 claims description 19
• 239000003613 bile acid Substances 0.000 claims description 19
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 19
• 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 19
• 229920001774 Perfluoroether Polymers 0.000 claims description 18
• 241000534944 Thia Species 0.000 claims description 18
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 18
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 18
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 18
• 125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 18
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 18
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 18
• 125000003282 alkyl amino group Chemical group 0.000 claims description 18
• 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 18
• 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 18
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 18
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 18
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 18
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 18
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 18
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 18
• 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 18
• 125000001769 aryl amino group Chemical group 0.000 claims description 18
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 18
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 18
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 18
• 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 18
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 18
• 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 18
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 18
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 18
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 18
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 18
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 18
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 18
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 18
• 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 18
• 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 18
• 125000004986 diarylamino group Chemical group 0.000 claims description 18
• 125000004992 haloalkylamino group Chemical group 0.000 claims description 18
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 18
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 18
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 18
• 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 18
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 18
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 18
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 18
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 18
• 125000005106 triarylsilyl group Chemical group 0.000 claims description 18
• 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 description 17
• 125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 17
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 17
• 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 17
• 230000003143 atherosclerotic effect Effects 0.000 claims description 17
• 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 17
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 16
• 239000005557 antagonist Substances 0.000 claims description 16
• 230000004060 metabolic process Effects 0.000 claims description 16
• 201000001320 Atherosclerosis Diseases 0.000 claims description 15
• 206010012601 diabetes mellitus Diseases 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 230000015572 biosynthetic process Effects 0.000 claims description 14
• 230000015556 catabolic process Effects 0.000 claims description 14
• 239000000556 agonist Substances 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• PDXPRWCJESNIIT-UHFFFAOYSA-N ethyl 1h-indole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2NC=CC2=C1 PDXPRWCJESNIIT-UHFFFAOYSA-N 0.000 claims description 13
• 150000004677 hydrates Chemical class 0.000 claims description 13
• 108090000865 liver X receptors Proteins 0.000 claims description 13
• 102000004311 liver X receptors Human genes 0.000 claims description 13
• 230000009102 absorption Effects 0.000 claims description 12
• 238000010521 absorption reaction Methods 0.000 claims description 12
• 235000012000 cholesterol Nutrition 0.000 claims description 12
• 150000007857 hydrazones Chemical class 0.000 claims description 12
• 201000001421 hyperglycemia Diseases 0.000 claims description 12
• 150000002923 oximes Chemical group 0.000 claims description 12
• 239000004031 partial agonist Substances 0.000 claims description 12
• 239000012453 solvate Substances 0.000 claims description 12
• 125000000464 thioxo group Chemical group S=* 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 206010008635 Cholestasis Diseases 0.000 claims description 11
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 11
• 102000004877 Insulin Human genes 0.000 claims description 11
• 108090001061 Insulin Proteins 0.000 claims description 11
• 208000008589 Obesity Diseases 0.000 claims description 11
• 150000001241 acetals Chemical class 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 11
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 11
• 150000002466 imines Chemical class 0.000 claims description 11
• 229940125396 insulin Drugs 0.000 claims description 11
• 235000020824 obesity Nutrition 0.000 claims description 11
• 230000009103 reabsorption Effects 0.000 claims description 11
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 11
• 150000007513 acids Chemical class 0.000 claims description 10
• 125000005107 alkyl diaryl silyl group Chemical group 0.000 claims description 10
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 10
• 230000007870 cholestasis Effects 0.000 claims description 10
• 231100000359 cholestasis Toxicity 0.000 claims description 10
• 238000003786 synthesis reaction Methods 0.000 claims description 10
• 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 10
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 9
• 206010049287 Lipodystrophy acquired Diseases 0.000 claims description 9
• 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 9
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 9
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
• 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 9
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 9
• 230000029142 excretion Effects 0.000 claims description 9
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 9
• 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims description 9
• 239000003112 inhibitor Substances 0.000 claims description 9
• 208000006132 lipodystrophy Diseases 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 230000028327 secretion Effects 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 9
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
• 150000002905 orthoesters Chemical class 0.000 claims description 8
• 208000011580 syndromic disease Diseases 0.000 claims description 8
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 8
• 210000000941 bile Anatomy 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• 150000002373 hemiacetals Chemical class 0.000 claims description 7
• 208000002874 Acne Vulgaris Diseases 0.000 claims description 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 description 6
• 206010000496 acne Diseases 0.000 claims description 6
• 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 description 5
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
• 229940125753 fibrate Drugs 0.000 claims description 5
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 5
• 230000001105 regulatory effect Effects 0.000 claims description 5
• RBCOYOYDYNXAFA-UHFFFAOYSA-L (5-hydroxy-4,6-dimethylpyridin-3-yl)methyl phosphate Chemical compound CC1=NC=C(COP([O-])([O-])=O)C(C)=C1O RBCOYOYDYNXAFA-UHFFFAOYSA-L 0.000 claims description 4
• 239000005541 ACE inhibitor Substances 0.000 claims description 4
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 229940123413 Angiotensin II antagonist Drugs 0.000 claims description 4
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 4
• 108010001831 LDL receptors Proteins 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 102000023984 PPAR alpha Human genes 0.000 claims description 4
• 102000001494 Sterol O-Acyltransferase Human genes 0.000 claims description 4
• 108010054082 Sterol O-acyltransferase Proteins 0.000 claims description 4
• 239000012190 activator Substances 0.000 claims description 4
• 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 4
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 4
• 239000003524 antilipemic agent Substances 0.000 claims description 4
• 229940127218 antiplatelet drug Drugs 0.000 claims description 4
• 239000002876 beta blocker Substances 0.000 claims description 4
• 229940097320 beta blocking agent Drugs 0.000 claims description 4
• 229960000516 bezafibrate Drugs 0.000 claims description 4
• 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 description 4
• 230000027455 binding Effects 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 201000001883 cholelithiasis Diseases 0.000 claims description 4
• 229960001214 clofibrate Drugs 0.000 claims description 4
• KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 claims description 4
• FDJOLVPMNUYSCM-UVKKECPRSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(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-2,7, Chemical compound [Co+3].N#[C-].C1([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)[N-]\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 FDJOLVPMNUYSCM-UVKKECPRSA-L 0.000 claims description 4
• 239000005516 coenzyme A Substances 0.000 claims description 4
• 229940093530 coenzyme a Drugs 0.000 claims description 4
• 230000003028 elevating effect Effects 0.000 claims description 4
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 229960002297 fenofibrate Drugs 0.000 claims description 4
• 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 description 4
• 239000002319 fibrinogen receptor antagonist Substances 0.000 claims description 4
• 208000001130 gallstones Diseases 0.000 claims description 4
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 4
• 208000020346 hyperlipoproteinemia Diseases 0.000 claims description 4
• 239000000411 inducer Substances 0.000 claims description 4
• 239000011664 nicotinic acid Substances 0.000 claims description 4
• 229960003512 nicotinic acid Drugs 0.000 claims description 4
• 235000001968 nicotinic acid Nutrition 0.000 claims description 4
• 230000002093 peripheral effect Effects 0.000 claims description 4
• 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 claims description 4
• 239000000106 platelet aggregation inhibitor Substances 0.000 claims description 4
• 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 description 4
• 229960003912 probucol Drugs 0.000 claims description 4
• 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 description 4
• 229960004622 raloxifene Drugs 0.000 claims description 4
• 239000003352 sequestering agent Substances 0.000 claims description 4
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 206010061218 Inflammation Diseases 0.000 claims description 3
• 208000032382 Ischaemic stroke Diseases 0.000 claims description 3
• 208000018737 Parkinson disease Diseases 0.000 claims description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
• 230000037365 barrier function of the epidermis Effects 0.000 claims description 3
• 210000002615 epidermis Anatomy 0.000 claims description 3
• 208000026278 immune system disease Diseases 0.000 claims description 3
• 230000004054 inflammatory process Effects 0.000 claims description 3
• 150000002632 lipids Chemical class 0.000 claims description 3
• 208000017520 skin disease Diseases 0.000 claims description 3
• GFWYOPVRMMAUNH-UHFFFAOYSA-N 1,1-dimethyl-3,6-dihydro-2H-azepino[4,5-b]indole-5-carboxylic acid Chemical compound CC1(C)CNC=C(C(O)=O)C2=C1C1=CC=CC=C1N2 GFWYOPVRMMAUNH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 2
• 206010061876 Obstruction Diseases 0.000 claims description 2
• 239000003963 antioxidant agent Substances 0.000 claims description 2
• 230000003078 antioxidant effect Effects 0.000 claims description 2
• 235000006708 antioxidants Nutrition 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 229940121360 farnesoid X receptor (fxr) agonists Drugs 0.000 claims description 2
• 230000005764 inhibitory process Effects 0.000 claims description 2
• 210000004400 mucous membrane Anatomy 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 102000006255 nuclear receptors Human genes 0.000 claims description 2
• 230000036961 partial effect Effects 0.000 claims description 2
• 229940088594 vitamin Drugs 0.000 claims description 2
• 229930003231 vitamin Natural products 0.000 claims description 2
• 235000013343 vitamin Nutrition 0.000 claims description 2
• 239000011782 vitamin Substances 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 26
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• 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 1
• RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 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
• 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
• 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
• 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
• UCQZPLINRZPGGJ-UHFFFAOYSA-N ethyl 3-(2-thiophen-2-yl-3H-1,3-thiazole-2-carbonyl)-2,6-dihydro-1H-azepino[4,5-b]indole-5-carboxylate Chemical compound C(C)OC(=O)C1=CN(CCC2=C1NC=1C=CC=CC21)C(=O)C2(SC=CN2)C=2SC=CC2 UCQZPLINRZPGGJ-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
• 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
• WMZYSBAYWHOOIM-UHFFFAOYSA-N ethyl 3-(4-fluorobenzoyl)-1,1-dimethyl-8-[(5-methylpiperazin-2-yl)methylcarbamoyloxy]-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C(C)OC(=O)C1=CN(CC(C2=C1NC=1C=C(C=CC21)OC(NCC2NCC(NC2)C)=O)(C)C)C(C2=CC=C(C=C2)F)=O WMZYSBAYWHOOIM-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
• 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
• 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
• 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
• 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
• 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
• CQJJXIMTNFCWIB-UHFFFAOYSA-N ethyl 8-benzoyloxycarbonyloxy-3-(4-fluorobenzoyl)-1,1-dimethyl-2,6-dihydroazepino[4,5-b]indole-5-carboxylate Chemical compound C(C)OC(=O)C1=CN(CC(C2=C1NC=1C=C(C=CC21)OC(=O)OC(C2=CC=CC=C2)=O)(C)C)C(C2=CC=C(C=C2)F)=O CQJJXIMTNFCWIB-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
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