KR20150056608A - 트리사이클릭 퀴놀린 및 퀴녹살린 유도체 - Google Patents
트리사이클릭 퀴놀린 및 퀴녹살린 유도체 Download PDFInfo
- Publication number
- KR20150056608A KR20150056608A KR1020157009502A KR20157009502A KR20150056608A KR 20150056608 A KR20150056608 A KR 20150056608A KR 1020157009502 A KR1020157009502 A KR 1020157009502A KR 20157009502 A KR20157009502 A KR 20157009502A KR 20150056608 A KR20150056608 A KR 20150056608A
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- KR
- South Korea
- Prior art keywords
- fluorinated
- alkyl
- alkoxy
- ring
- diazepino
- 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.)
- Withdrawn
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 356
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 202
- 238000000034 method Methods 0.000 claims abstract description 71
- 239000003814 drug Substances 0.000 claims abstract description 42
- 238000011282 treatment Methods 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- -1 1 -C 2 - alkyl Chemical group 0.000 claims description 538
- 125000005842 heteroatom Chemical group 0.000 claims description 204
- 229910052760 oxygen Inorganic materials 0.000 claims description 186
- 229910052739 hydrogen Inorganic materials 0.000 claims description 144
- 125000001424 substituent group Chemical group 0.000 claims description 141
- 239000001257 hydrogen Substances 0.000 claims description 133
- 229910052717 sulfur Inorganic materials 0.000 claims description 111
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 104
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 95
- 125000004432 carbon atom Chemical group C* 0.000 claims description 92
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 91
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
- 229920006395 saturated elastomer Polymers 0.000 claims description 91
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 90
- 229910052799 carbon Inorganic materials 0.000 claims description 84
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- 208000035475 disorder Diseases 0.000 claims description 68
- 229910052736 halogen Inorganic materials 0.000 claims description 67
- 150000002367 halogens Chemical class 0.000 claims description 67
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 64
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 64
- 229910052757 nitrogen Inorganic materials 0.000 claims description 62
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
- 229910052805 deuterium Inorganic materials 0.000 claims description 61
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 56
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 52
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 51
- 150000003839 salts Chemical class 0.000 claims description 51
- 125000004122 cyclic group Chemical group 0.000 claims description 47
- 206010012601 diabetes mellitus Diseases 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical class [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 44
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 39
- 238000002360 preparation method Methods 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 229910052731 fluorine Inorganic materials 0.000 claims description 29
- 150000001204 N-oxides Chemical class 0.000 claims description 28
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 28
- 201000000980 schizophrenia Diseases 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 208000002193 Pain Diseases 0.000 claims description 22
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 22
- 125000002837 carbocyclic group Chemical group 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 22
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 20
- 230000036407 pain Effects 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 208000008589 Obesity Diseases 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 11
- 206010015037 epilepsy Diseases 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 11
- 235000005911 diet Nutrition 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 208000011117 substance-related disease Diseases 0.000 claims description 10
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 10
- 208000020925 Bipolar disease Diseases 0.000 claims description 9
- 230000000378 dietary effect Effects 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 230000002285 radioactive effect Effects 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 208000019695 Migraine disease Diseases 0.000 claims description 8
- 230000003542 behavioural effect Effects 0.000 claims description 8
- 208000015114 central nervous system disease Diseases 0.000 claims description 8
- 208000010877 cognitive disease Diseases 0.000 claims description 8
- 206010027599 migraine Diseases 0.000 claims description 8
- 208000020016 psychiatric disease Diseases 0.000 claims description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 7
- 206010022489 Insulin Resistance Diseases 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 206010046543 Urinary incontinence Diseases 0.000 claims description 7
- 125000003566 oxetanyl group Chemical group 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 208000028698 Cognitive impairment Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 6
- 230000036506 anxiety Effects 0.000 claims description 6
- 201000001881 impotence Diseases 0.000 claims description 6
- 208000020431 spinal cord injury Diseases 0.000 claims description 6
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 5
- 208000002249 Diabetes Complications Diseases 0.000 claims description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
- 230000007278 cognition impairment Effects 0.000 claims description 5
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001975 deuterium Chemical group 0.000 claims description 5
- 201000001421 hyperglycemia Diseases 0.000 claims description 5
- 208000007848 Alcoholism Diseases 0.000 claims description 4
- 208000000044 Amnesia Diseases 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 206010003805 Autism Diseases 0.000 claims description 4
- 208000020706 Autistic disease Diseases 0.000 claims description 4
- 208000022497 Cocaine-Related disease Diseases 0.000 claims description 4
- 206010013654 Drug abuse Diseases 0.000 claims description 4
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 4
- 208000026139 Memory disease Diseases 0.000 claims description 4
- 206010030043 Ocular hypertension Diseases 0.000 claims description 4
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 206010041250 Social phobia Diseases 0.000 claims description 4
- 206010001584 alcohol abuse Diseases 0.000 claims description 4
- 208000025746 alcohol use disease Diseases 0.000 claims description 4
- 201000007201 aphasia Diseases 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 208000030963 borderline personality disease Diseases 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 201000001272 cocaine abuse Diseases 0.000 claims description 4
- 208000014674 injury Diseases 0.000 claims description 4
- 230000004410 intraocular pressure Effects 0.000 claims description 4
- 230000006984 memory degeneration Effects 0.000 claims description 4
- 208000023060 memory loss Diseases 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- FZCKMQWMUQLWLE-UHFFFAOYSA-N 1,2,3,4,6,7-hexahydrospiro[[1,4]diazepino[6,7,1-ij]quinoline-8,1'-cyclopropane] Chemical compound C1CC11C(C=CC=C2CNCC3)=C2N3CC1 FZCKMQWMUQLWLE-UHFFFAOYSA-N 0.000 claims description 3
- FIYUEHKLAAQGRX-UHFFFAOYSA-N 1-cyclopropyl-2,3,5,6,7,8-hexahydro-1h-[1,4]diazepino[1,7,6-de]-quinoxaline Chemical compound C1CC1C1C(C=CC=C2NCC3)=C2N3CCN1 FIYUEHKLAAQGRX-UHFFFAOYSA-N 0.000 claims description 3
- ZYTJBRCFLDIGMV-UHFFFAOYSA-N 16-methyl-7,10-diazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene Chemical compound C1CNCC2=CC=CC3=C2N1CC1CCCC13C ZYTJBRCFLDIGMV-UHFFFAOYSA-N 0.000 claims description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 206010012655 Diabetic complications Diseases 0.000 claims description 3
- 206010057671 Female sexual dysfunction Diseases 0.000 claims description 3
- 208000030990 Impulse-control disease Diseases 0.000 claims description 3
- 201000009906 Meningitis Diseases 0.000 claims description 3
- 206010014599 encephalitis Diseases 0.000 claims description 3
- IEOUSWADWJLLCH-UHFFFAOYSA-N pyrrolo[1,2-a]quinoxaline Chemical compound C1=NC2=CC=CC=C2N2C1=CC=C2 IEOUSWADWJLLCH-UHFFFAOYSA-N 0.000 claims description 3
- 210000003625 skull Anatomy 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 208000016261 weight loss Diseases 0.000 claims description 3
- 230000004580 weight loss Effects 0.000 claims description 3
- ZJEQZMXKIFKCQJ-UHFFFAOYSA-N 2,4,4-trimethyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1NCCN2C(C)CC(C)(C)C3=CC=CC1=C32 ZJEQZMXKIFKCQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004011 3 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000001845 4 membered carbocyclic group Chemical group 0.000 claims description 2
- HOBOUSVAKXURJE-UHFFFAOYSA-N 4-(cyclopentylmethyl)-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CN(C=23)CCNCC3=CC=CC=2N1CC1CCCC1 HOBOUSVAKXURJE-UHFFFAOYSA-N 0.000 claims description 2
- INPOAPUJXMPTPA-UHFFFAOYSA-N 4-(cyclopropylmethyl)-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CN(C=23)CCNCC3=CC=CC=2N1CC1CC1 INPOAPUJXMPTPA-UHFFFAOYSA-N 0.000 claims description 2
- XHEDDWTXFCYRQL-UHFFFAOYSA-N 4-cyclobutyl-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CCC1N1C(C=CC=C2CNCC3)=C2N3CC1 XHEDDWTXFCYRQL-UHFFFAOYSA-N 0.000 claims description 2
- LWEGPOSKHDGAKN-UHFFFAOYSA-N 4-cyclopentyl-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CCCC1N1C(C=CC=C2CNCC3)=C2N3CC1 LWEGPOSKHDGAKN-UHFFFAOYSA-N 0.000 claims description 2
- YAQUWFYEOQODQM-UHFFFAOYSA-N 4-methyl-1,2,3,4,6,7-hexahydrospiro[[1,4]diazepino[6,7,1-ij]-quinoline-8,1'-cyclobutane] Chemical compound CC1CNCC2=CC=CC3=C2N1CCC31CCC1 YAQUWFYEOQODQM-UHFFFAOYSA-N 0.000 claims description 2
- PFDPYSKVVWYUQZ-UHFFFAOYSA-N 4-methyl-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CNCC2=CC=CC3=C2N1CCN3C PFDPYSKVVWYUQZ-UHFFFAOYSA-N 0.000 claims description 2
- FVRKOPKMEZYHSP-UHFFFAOYSA-N 4-methyl-4-phenyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-trien-2-one Chemical compound C1C(=O)N(C=23)CCNCC3=CC=CC=2C1(C)C1=CC=CC=C1 FVRKOPKMEZYHSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- HPUJLIYEPRECTP-UHFFFAOYSA-N 5,6,7,9,9a,10,11,12,13,14-decahydro-4h-azepino[1,2-a][1,4]-diazepino [1,7,6-de]quinoxaline Chemical compound C1=2C3=CC=CC=2CNCCN1CC1N3CCCCC1 HPUJLIYEPRECTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- 208000036626 Mental retardation Diseases 0.000 claims description 2
- 208000016222 Pancreatic disease Diseases 0.000 claims description 2
- 208000008348 Post-Concussion Syndrome Diseases 0.000 claims description 2
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 2
- 230000003044 adaptive effect Effects 0.000 claims description 2
- 208000025748 atypical depressive disease Diseases 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 201000010064 diabetes insipidus Diseases 0.000 claims description 2
- 230000036651 mood Effects 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- 208000019906 panic disease Diseases 0.000 claims description 2
- 201000002859 sleep apnea Diseases 0.000 claims description 2
- 208000020685 sleep-wake disease Diseases 0.000 claims description 2
- NQRFHPFJQSARLD-UHFFFAOYSA-N spiro[1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene-4,1'-cyclohexane] Chemical compound C1CCCCC21C(C=CC=C1CNCC3)=C1N3CC2 NQRFHPFJQSARLD-UHFFFAOYSA-N 0.000 claims description 2
- 206010027304 Menopausal symptoms Diseases 0.000 claims 2
- HEDXDGPMKTVKTG-OAHLLOKOSA-N (4R)-4-ethyl-4-methyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CNCC2=CC=CC3=C2N1CC[C@@]3(C)CC HEDXDGPMKTVKTG-OAHLLOKOSA-N 0.000 claims 1
- HEDXDGPMKTVKTG-HNNXBMFYSA-N (4S)-4-ethyl-4-methyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CNCC2=CC=CC3=C2N1CC[C@]3(C)CC HEDXDGPMKTVKTG-HNNXBMFYSA-N 0.000 claims 1
- OURGNMUCUZOUAY-UHFFFAOYSA-N 1,4,13-triazatricyclo[7.4.1.05,14]tetradeca-3,5,7,9(14),10,12-hexaene Chemical compound C1=CC=NN2CC=NC3=CC=CC1=C32 OURGNMUCUZOUAY-UHFFFAOYSA-N 0.000 claims 1
- WKJISILMIWKRHK-UHFFFAOYSA-N 13-ethyl-4,4-dimethyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound CCC1CNCC2=CC=CC3=C2N1CCC3(C)C WKJISILMIWKRHK-UHFFFAOYSA-N 0.000 claims 1
- PCWZZINGLVTYHO-UHFFFAOYSA-N 13-methylspiro[1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene-4,1'-cyclopropane] Chemical compound CC1CNCC2=CC=CC3=C2N1CCC31CC1 PCWZZINGLVTYHO-UHFFFAOYSA-N 0.000 claims 1
- NBMFBQZMZRXHHA-UHFFFAOYSA-N 2,2-dimethyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5(14),6,8-triene Chemical compound C1NCCN2C(C)(C)CCC3=CC=CC1=C32 NBMFBQZMZRXHHA-UHFFFAOYSA-N 0.000 claims 1
- ZIFIYJHNBNZIMM-UHFFFAOYSA-N 2-methyl-7,10,16-triazatetracyclo[8.6.1.05,17.012,16]heptadeca-1,3,5(17)-triene Chemical compound C12=C3C(C)=CC=C2CNCCN1CC1N3CCC1 ZIFIYJHNBNZIMM-UHFFFAOYSA-N 0.000 claims 1
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
- LAKZLGUTIVXKGU-UHFFFAOYSA-N 4,11-dimethyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-trien-4-ol Chemical compound C1N(C)CCN2CCC(C)(O)C3=CC=CC1=C23 LAKZLGUTIVXKGU-UHFFFAOYSA-N 0.000 claims 1
- LSFQEAIJWRBSLL-UHFFFAOYSA-N 4,4,13-trimethyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound CC1CNCC2=CC=CC3=C2N1CCC3(C)C LSFQEAIJWRBSLL-UHFFFAOYSA-N 0.000 claims 1
- YACVKZVOENDYND-UHFFFAOYSA-N 4,4-dimethyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-trien-10-one Chemical compound C1CNC(=O)C2=CC=CC3=C2N1CCC3(C)C YACVKZVOENDYND-UHFFFAOYSA-N 0.000 claims 1
- USVPKQYKHVMSSP-UHFFFAOYSA-N 4,4-dimethyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-trien-2-one Chemical compound C1CNCC2=CC=CC3=C2N1C(=O)CC3(C)C USVPKQYKHVMSSP-UHFFFAOYSA-N 0.000 claims 1
- HCLPZGGBCIQIDF-UHFFFAOYSA-N 4-(oxetan-3-yl)-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1OCC1N1C(C=CC=C2CNCC3)=C2N3CC1 HCLPZGGBCIQIDF-UHFFFAOYSA-N 0.000 claims 1
- BLAMRFZKBWBQPZ-UHFFFAOYSA-N 4-cyclobutyl-13-methyl-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CN(C2=3)C(C)CNCC2=CC=CC=3N1C1CCC1 BLAMRFZKBWBQPZ-UHFFFAOYSA-N 0.000 claims 1
- ABNMENQTUIQRCO-UHFFFAOYSA-N 4-ethyl-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CNCC2=CC=CC3=C2N1CCN3CC ABNMENQTUIQRCO-UHFFFAOYSA-N 0.000 claims 1
- XMRHIDQTLUJKMZ-UHFFFAOYSA-N 4-ethyl-13-methyl-1,4,11-triazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound CC1CNCC2=CC=CC3=C2N1CCN3CC XMRHIDQTLUJKMZ-UHFFFAOYSA-N 0.000 claims 1
- HEDXDGPMKTVKTG-UHFFFAOYSA-N 4-ethyl-4-methyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CNCC2=CC=CC3=C2N1CCC3(C)CC HEDXDGPMKTVKTG-UHFFFAOYSA-N 0.000 claims 1
- RLJXLVOZTUAUGB-UHFFFAOYSA-N 4-methyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-trien-4-ol Chemical compound C1CNCC2=CC=CC3=C2N1CCC3(O)C RLJXLVOZTUAUGB-UHFFFAOYSA-N 0.000 claims 1
- VOXZIPRHQDYZLK-UHFFFAOYSA-N 4-methyl-4-(trifluoromethyl)-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-trien-10-one Chemical compound C1CNC(=O)C2=CC=CC3=C2N1CCC3(C)C(F)(F)F VOXZIPRHQDYZLK-UHFFFAOYSA-N 0.000 claims 1
- HLTUJLABXMGNHD-UHFFFAOYSA-N 4-methyl-4-phenyl-1,11-diazatricyclo[7.4.1.05,14]tetradeca-5,7,9(14)-triene Chemical compound C1CN(C=23)CCNCC3=CC=CC=2C1(C)C1=CC=CC=C1 HLTUJLABXMGNHD-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
- C07D471/06—Peri-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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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| PCT/EP2013/069036 WO2014041131A1 (en) | 2012-09-14 | 2013-09-13 | Tricyclic quinoline and quinoxaline derivatives |
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Cited By (3)
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| KR20230055979A (ko) * | 2021-10-18 | 2023-04-26 | 주식회사 사피엔스바이오 | 신규한 화합물 및 이를 포함하는 약학적 조성물 |
| WO2023068755A1 (ko) * | 2021-10-18 | 2023-04-27 | 주식회사 사피엔스바이오 | 신규한 화합물 및 이를 포함하는 약학적 조성물 |
| KR20230171398A (ko) * | 2022-06-10 | 2023-12-20 | 주식회사 사피엔스바이오 | 신규한 화합물 및 이를 유효성분으로 포함하는 약학적 조성물 |
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| EP2943485B1 (en) | 2013-01-14 | 2017-09-20 | Incyte Holdings Corporation | Bicyclic aromatic carboxamide compounds useful as pim kinase inhibitors |
| TWI662030B (zh) | 2013-01-15 | 2019-06-11 | 英塞特控股公司 | 適用作ｐｉｍ激酶抑制劑之噻唑甲醯胺及吡啶甲醯胺化合物 |
| WO2014145192A1 (en) | 2013-03-15 | 2014-09-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US9556197B2 (en) | 2013-08-23 | 2017-01-31 | Incyte Corporation | Furo- and thieno-pyridine carboxamide compounds useful as pim kinase inhibitors |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| KR102967223B1 (ko) | 2013-12-03 | 2026-05-19 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 신규한 방법 |
| US9540376B2 (en) | 2014-03-14 | 2017-01-10 | AbbVie Deutschland GmbH & Co. KG | Hexahydrodiazepinoquinolines carrying a substituted alkyl radical |
| US9573950B2 (en) | 2014-03-14 | 2017-02-21 | Abbvie Deutschland Gmbh & Co Kg | Substituted [1,4]diazepino[6,7,1-ij]quinolines as serotonin 5-HT2C receptor modulators |
| KR20220054908A (ko) | 2014-04-04 | 2022-05-03 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| US9580418B2 (en) | 2014-07-14 | 2017-02-28 | Incyte Corporation | Bicyclic aromatic carboxamide compounds useful as Pim kinase inhibitors |
| WO2016010897A1 (en) | 2014-07-14 | 2016-01-21 | Incyte Corporation | Bicyclic heteroaromatic carboxamide compounds useful as pim kinase inhibitors |
| HUE047169T2 (hu) * | 2015-04-27 | 2020-04-28 | Arena Pharm Inc | 5-HT2C receptor agonisták és készítmények és felhasználási eljárások |
| WO2016196244A1 (en) | 2015-05-29 | 2016-12-08 | Incyte Corporation | Pyridineamine compounds useful as pim kinase inhibitors |
| JP6789578B2 (ja) * | 2015-07-31 | 2020-11-25 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ｈｔ２ｃ受容体アゴニストおよび組成物、ならびに使用方法 |
| AR105967A1 (es) | 2015-09-09 | 2017-11-29 | Incyte Corp | Sales de un inhibidor de pim quinasa |
| WO2017059251A1 (en) | 2015-10-02 | 2017-04-06 | Incyte Corporation | Heterocyclic compounds useful as pim kinase inhibitors |
| WO2017117514A1 (en) * | 2015-12-31 | 2017-07-06 | Tung Roger D | Deuterated iti-007 |
| RU2743513C2 (ru) | 2016-01-26 | 2021-02-19 | Интра-Селлулар Терапиз, Инк. | Органические соединения |
| IL281050B2 (en) | 2016-03-25 | 2023-04-01 | Intra Cellular Therapies Inc | A controlled or delayed release pharmaceutical preparation containing a deuterated compound |
| US20200392135A1 (en) * | 2016-03-25 | 2020-12-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US10682354B2 (en) | 2016-03-28 | 2020-06-16 | Intra-Cellular Therapies, Inc. | Compositions and methods |
| JP7013454B2 (ja) | 2016-10-12 | 2022-02-15 | イントラ－セルラー・セラピーズ・インコーポレイテッド | アモルファス固体分散体 |
| EP3562484B1 (en) | 2016-12-29 | 2021-08-25 | Intra-Cellular Therapies, Inc. | Pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline derivatives useful in the treatment of cns disorders |
| WO2018126140A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP7224333B2 (ja) | 2017-07-26 | 2023-02-17 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| TW201924683A (zh) | 2017-12-08 | 2019-07-01 | 美商英塞特公司 | 用於治療骨髓增生性贅瘤的低劑量組合療法 |
| WO2019178484A1 (en) | 2018-03-16 | 2019-09-19 | Intra-Cellular Therapies, Inc. | Novel methods |
| SMT202600133T1 (it) * | 2018-03-23 | 2026-05-12 | Intra Cellular Therapies Inc | Composti organici |
| AU2019240226B2 (en) | 2018-03-23 | 2024-11-28 | Intra-Cellular Therapies, Inc. | Organic compounds |
| KR20210104785A (ko) | 2018-12-17 | 2021-08-25 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| US12331052B2 (en) | 2018-12-21 | 2025-06-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP7377871B2 (ja) | 2018-12-21 | 2023-11-10 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| EP4134101A1 (en) | 2019-07-07 | 2023-02-15 | Intra-Cellular Therapies, Inc. | Deuterated lumateperone for the treatment of the bipolar ii disorder |
| JP2022549335A (ja) | 2019-09-25 | 2022-11-24 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規方法 |
| WO2021119334A1 (en) | 2019-12-11 | 2021-06-17 | Intra-Cellular Therapies, Inc. | Organic compound |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
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- 2013-09-13 RU RU2015113558A patent/RU2015113558A/ru not_active Application Discontinuation
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- 2013-09-14 TW TW102133403A patent/TW201414735A/zh unknown
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2015
- 2015-03-12 IL IL237726A patent/IL237726A0/en unknown
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2018
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20230055979A (ko) * | 2021-10-18 | 2023-04-26 | 주식회사 사피엔스바이오 | 신규한 화합물 및 이를 포함하는 약학적 조성물 |
| WO2023068755A1 (ko) * | 2021-10-18 | 2023-04-27 | 주식회사 사피엔스바이오 | 신규한 화합물 및 이를 포함하는 약학적 조성물 |
| KR20230171398A (ko) * | 2022-06-10 | 2023-12-20 | 주식회사 사피엔스바이오 | 신규한 화합물 및 이를 유효성분으로 포함하는 약학적 조성물 |
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| Publication number | Publication date |
|---|---|
| TW201414735A (zh) | 2014-04-16 |
| US20200283439A1 (en) | 2020-09-10 |
| JP2015528478A (ja) | 2015-09-28 |
| PE20150777A1 (es) | 2015-06-20 |
| SG11201501894VA (en) | 2015-04-29 |
| US20190071443A1 (en) | 2019-03-07 |
| US10118926B2 (en) | 2018-11-06 |
| EP2895485A1 (en) | 2015-07-22 |
| NZ631187A (en) | 2017-03-31 |
| IN2015DN02070A (cg-RX-API-DMAC7.html) | 2015-08-14 |
| RU2015113558A (ru) | 2016-11-10 |
| AU2013314279A1 (en) | 2015-04-02 |
| MX2015003364A (es) | 2016-03-31 |
| AR092568A1 (es) | 2015-04-22 |
| CA2884548A1 (en) | 2014-03-20 |
| BR112015005743A2 (pt) | 2017-07-04 |
| CL2015000628A1 (es) | 2015-10-30 |
| JP6290217B2 (ja) | 2018-03-07 |
| AU2018200572A1 (en) | 2018-02-15 |
| CN104995191A (zh) | 2015-10-21 |
| UY35029A (es) | 2014-04-30 |
| WO2014041131A1 (en) | 2014-03-20 |
| CR20150186A (es) | 2015-08-28 |
| US20140080816A1 (en) | 2014-03-20 |
| DOP2015000058A (es) | 2015-04-15 |
| IL237726A0 (en) | 2015-05-31 |
| PH12015500551A1 (en) | 2015-05-04 |
| HK1212684A1 (zh) | 2016-06-17 |
| UA116216C2 (uk) | 2018-02-26 |
| ECSP15012766A (es) | 2017-06-30 |
| AU2013314279B2 (en) | 2017-11-02 |
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