CA2782783C - Fused heterocyclic compounds - Google Patents

Info

Publication number

CA2782783C

CA2782783C CA2782783A CA2782783A CA2782783C CA 2782783 C CA2782783 C CA 2782783C CA 2782783 A CA2782783 A CA 2782783A CA 2782783 A CA2782783 A CA 2782783A CA 2782783 C CA2782783 C CA 2782783C

Authority

CA

Canada

Prior art keywords

6alkyl

defined above

substituted

ring

optionally

Prior art date

2003-09-17

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 - Fee Related

Links

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• CIPO
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• 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 34
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 18
• 201000010099 disease Diseases 0.000 claims abstract description 12
• 230000001404 mediated effect Effects 0.000 claims abstract description 11
• 229940076279 serotonin Drugs 0.000 claims abstract description 6
• 150000001875 compounds Chemical class 0.000 claims description 580
• -1 -Ophenyl Chemical group 0.000 claims description 335
• 229910052799 carbon Inorganic materials 0.000 claims description 269
• 125000004432 carbon atom Chemical group C* 0.000 claims description 179
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 170
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 156
• 150000001721 carbon Chemical group 0.000 claims description 139
• 125000001424 substituent group Chemical group 0.000 claims description 121
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 97
• 125000004076 pyridyl group Chemical group 0.000 claims description 94
• 125000005843 halogen group Chemical group 0.000 claims description 86
• 125000003118 aryl group Chemical group 0.000 claims description 85
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 72
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 72
• 125000000623 heterocyclic group Chemical group 0.000 claims description 70
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 68
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 66
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 60
• 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 56
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 56
• 150000002430 hydrocarbons Chemical group 0.000 claims description 56
• 125000002950 monocyclic group Chemical group 0.000 claims description 56
• 125000006413 ring segment Chemical group 0.000 claims description 56
• 150000001408 amides Chemical class 0.000 claims description 52
• 229910052757 nitrogen Inorganic materials 0.000 claims description 52
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 49
• 125000001544 thienyl group Chemical group 0.000 claims description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 44
• 125000005842 heteroatom Chemical group 0.000 claims description 43
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 39
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 33
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 33
• 125000002541 furyl group Chemical group 0.000 claims description 32
• 125000001624 naphthyl group Chemical group 0.000 claims description 32
• 239000001257 hydrogen Substances 0.000 claims description 31
• 150000002148 esters Chemical class 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 29
• 229920006395 saturated elastomer Polymers 0.000 claims description 29
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 27
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 27
• 230000000694 effects Effects 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 229910052703 rhodium Inorganic materials 0.000 claims description 19
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 18
• 125000002971 oxazolyl group Chemical group 0.000 claims description 17
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 230000002265 prevention Effects 0.000 claims description 15
• 229940075993 receptor modulator Drugs 0.000 claims description 15
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 14
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 14
• 125000002837 carbocyclic group Chemical group 0.000 claims description 14
• 150000004677 hydrates Chemical class 0.000 claims description 14
• 239000012453 solvate Substances 0.000 claims description 14
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 208000019901 Anxiety disease Diseases 0.000 claims description 11
• 230000036506 anxiety Effects 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 10
• 208000019695 Migraine disease Diseases 0.000 claims description 10
• 206010027599 migraine Diseases 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• RBYJHELKTYHZNG-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2CCNCCC2=C1C1=CC=C(F)C=C1 RBYJHELKTYHZNG-UHFFFAOYSA-N 0.000 claims description 8
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 208000030814 Eating disease Diseases 0.000 claims description 7
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 7
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 7
• 235000014632 disordered eating Nutrition 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• 201000000980 schizophrenia Diseases 0.000 claims description 7
• 208000019116 sleep disease Diseases 0.000 claims description 7
• 208000020925 Bipolar disease Diseases 0.000 claims description 6
• 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 6
• 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 6
• 208000019022 Mood disease Diseases 0.000 claims description 6
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 6
• 208000028017 Psychotic disease Diseases 0.000 claims description 6
• 201000001880 Sexual dysfunction Diseases 0.000 claims description 6
• 206010046543 Urinary incontinence Diseases 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• 230000030135 gastric motility Effects 0.000 claims description 6
• 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 231100000872 sexual dysfunction Toxicity 0.000 claims description 6
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 5
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 5
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 4
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 4
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 4
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
• VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
• 208000002193 Pain Diseases 0.000 claims description 4
• SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 4
• 230000005856 abnormality Effects 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 208000015114 central nervous system disease Diseases 0.000 claims description 4
• 230000027288 circadian rhythm Effects 0.000 claims description 4
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 4
• WPHGSKGZRAQSGP-UHFFFAOYSA-N norcarane Chemical compound C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
• 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 claims description 4
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 4
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
• 238000002600 positron emission tomography Methods 0.000 claims description 4
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 208000007848 Alcoholism Diseases 0.000 claims description 3
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
• 206010012735 Diarrhoea Diseases 0.000 claims description 3
• 208000010412 Glaucoma Diseases 0.000 claims description 3
• 206010020772 Hypertension Diseases 0.000 claims description 3
• 208000001953 Hypotension Diseases 0.000 claims description 3
• 206010061218 Inflammation Diseases 0.000 claims description 3
• 206010028813 Nausea Diseases 0.000 claims description 3
• 208000008589 Obesity Diseases 0.000 claims description 3
• 208000022873 Ocular disease Diseases 0.000 claims description 3
• 208000003435 Optic Neuritis Diseases 0.000 claims description 3
• 206010040070 Septic Shock Diseases 0.000 claims description 3
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 3
• 206010001584 alcohol abuse Diseases 0.000 claims description 3
• 208000025746 alcohol use disease Diseases 0.000 claims description 3
• 125000004429 atom Chemical group 0.000 claims description 3
• 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
• 230000002496 gastric effect Effects 0.000 claims description 3
• 230000003054 hormonal effect Effects 0.000 claims description 3
• 230000036543 hypotension Effects 0.000 claims description 3
• 230000004054 inflammatory process Effects 0.000 claims description 3
• 208000028867 ischemia Diseases 0.000 claims description 3
• 208000017169 kidney disease Diseases 0.000 claims description 3
• 208000002780 macular degeneration Diseases 0.000 claims description 3
• 230000002503 metabolic effect Effects 0.000 claims description 3
• 230000008693 nausea Effects 0.000 claims description 3
• 235000020824 obesity Nutrition 0.000 claims description 3
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 3
• 230000036303 septic shock Effects 0.000 claims description 3
• 230000035939 shock Effects 0.000 claims description 3
• 208000022925 sleep disturbance Diseases 0.000 claims description 3
• 230000002792 vascular Effects 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004820 3-methylbutylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• FPWNLURCHDRMHC-UHFFFAOYSA-N 4-chlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=CC=C1 FPWNLURCHDRMHC-UHFFFAOYSA-N 0.000 claims description 2
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
• 125000003725 azepanyl group Chemical group 0.000 claims description 2
• 239000004305 biphenyl Substances 0.000 claims description 2
• 235000010290 biphenyl Nutrition 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 claims description 2
• 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims description 2
• 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 125000001041 indolyl group Chemical group 0.000 claims description 2
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
• 239000003068 molecular probe Substances 0.000 claims description 2
• 125000002757 morpholinyl group Chemical group 0.000 claims description 2
• 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 claims description 2
• 125000004193 piperazinyl group Chemical group 0.000 claims description 2
• 125000003386 piperidinyl group Chemical group 0.000 claims description 2
• MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 2
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
• 238000002603 single-photon emission computed tomography Methods 0.000 claims description 2
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims 19
• 229910052717 sulfur Inorganic materials 0.000 claims 19
• IWPAPSIKRTYFSR-UHFFFAOYSA-N 2-cyclopentyl-3-(4-fluorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(F)=CC=C1C1=C(CCNCC2)C2=NN1C1CCCC1 IWPAPSIKRTYFSR-UHFFFAOYSA-N 0.000 claims 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
• PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 1
• ORVOJXRXOVZCRU-UHFFFAOYSA-N 2-benzyl-3-(4-chlorophenyl)-5,6-dihydro-4h-pyrrolo[3,4-c]pyrazole Chemical compound C1=CC(Cl)=CC=C1C1=C(CNC2)C2=NN1CC1=CC=CC=C1 ORVOJXRXOVZCRU-UHFFFAOYSA-N 0.000 claims 1
• KRSWZAPAEZRNQN-UHFFFAOYSA-N 2-cyclobutyl-3-(4-fluorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(F)=CC=C1C1=C(CCNCC2)C2=NN1C1CCC1 KRSWZAPAEZRNQN-UHFFFAOYSA-N 0.000 claims 1
• QEUUGUOVKZCUGI-UHFFFAOYSA-N 2-cyclobutyl-3-(4-methylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(C)=CC=C1C1=C(CCNCC2)C2=NN1C1CCC1 QEUUGUOVKZCUGI-UHFFFAOYSA-N 0.000 claims 1
• GPJWIZYNTCBZFV-UHFFFAOYSA-N 2-cyclobutyl-3-[4-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=C(CCNCC2)C2=NN1C1CCC1 GPJWIZYNTCBZFV-UHFFFAOYSA-N 0.000 claims 1
• KONWFBIBXNRUKS-UHFFFAOYSA-N 2-cyclobutyl-3-phenyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1CCC1N1C(C=2C=CC=CC=2)=C2CCNCCC2=N1 KONWFBIBXNRUKS-UHFFFAOYSA-N 0.000 claims 1
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