JP5069907B2 - 縮合複素環式化合物 - Google Patents

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Publication number

JP5069907B2

JP5069907B2 JP2006526993A JP2006526993A JP5069907B2 JP 5069907 B2 JP5069907 B2 JP 5069907B2 JP 2006526993 A JP2006526993 A JP 2006526993A JP 2006526993 A JP2006526993 A JP 2006526993A JP 5069907 B2 JP5069907 B2 JP 5069907B2

Authority

JP

Japan

Prior art keywords

triaza

phenyl

hexahydro

azulene

chloro

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

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• 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 597
• -1 4-chlorophenyl 2-fluorophenyl Chemical group 0.000 claims description 332
• 125000000217 alkyl group Chemical group 0.000 claims description 204
• 229910052799 carbon Inorganic materials 0.000 claims description 82
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 60
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 47
• 238000006467 substitution reaction Methods 0.000 claims description 41
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
• 239000002253 acid Substances 0.000 claims description 33
• 125000004432 carbon atom Chemical group C* 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 239000001257 hydrogen Substances 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 150000001721 carbon Chemical group 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 150000001408 amides Chemical class 0.000 claims description 16
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 150000002430 hydrocarbons Chemical group 0.000 claims description 13
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 11
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 11
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 230000000694 effects Effects 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
• 125000005605 benzo group Chemical group 0.000 claims description 9
• 230000027455 binding Effects 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• UKJPMZGILXATGT-UHFFFAOYSA-N 1-benzyl-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C(C=1CCNCCC=11)=NN1CC1=CC=CC=C1 UKJPMZGILXATGT-UHFFFAOYSA-N 0.000 claims description 8
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 125000002029 aromatic hydrocarbon group Chemical group 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
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• JAWBBUARDVCNSH-UHFFFAOYSA-N 2-butan-2-yl-3-(4-methylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCC(C)N1N=C2CCNCCC2=C1C1=CC=C(C)C=C1 JAWBBUARDVCNSH-UHFFFAOYSA-N 0.000 claims description 7
• YYCVTBSEGMPXJR-UHFFFAOYSA-N 2-cyclopropyl-3-(4-methylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(C)=CC=C1C1=C(CCNCC2)C2=NN1C1CC1 YYCVTBSEGMPXJR-UHFFFAOYSA-N 0.000 claims description 7
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 6
• AUBZKCKTPAZIBA-UHFFFAOYSA-N 2-cyclohexyl-3-phenyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1CCCCC1N1C(C=2C=CC=CC=2)=C2CCNCCC2=N1 AUBZKCKTPAZIBA-UHFFFAOYSA-N 0.000 claims description 6
• BJYUYYIMVOZLEA-UHFFFAOYSA-N 2-ethyl-3-(4-methylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCN1N=C2CCNCCC2=C1C1=CC=C(C)C=C1 BJYUYYIMVOZLEA-UHFFFAOYSA-N 0.000 claims description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
• DHIBKJMENXGCKF-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(thiophen-2-ylmethyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C(C=1CCNCCC=11)=NN1CC1=CC=CS1 DHIBKJMENXGCKF-UHFFFAOYSA-N 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
• DIQZMBPDLFAJLK-UHFFFAOYSA-N 1-benzyl-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C1=CC(Cl)=CC=C1C(C=1CCNCCC=11)=NN1CC1=CC=CC=C1 DIQZMBPDLFAJLK-UHFFFAOYSA-N 0.000 claims description 5
• FFVSNZYRWFBDFY-UHFFFAOYSA-N 1-benzyl-3-(4-fluorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(F)=CC=C1C(C=1CCNCCC=11)=NN1CC1=CC=CC=C1 FFVSNZYRWFBDFY-UHFFFAOYSA-N 0.000 claims description 5
• ARFWKBWXBMDBHD-UHFFFAOYSA-N 1-benzyl-3-thiophen-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound N1=C(C=2SC=CC=2)C=2CCNCCC=2N1CC1=CC=CC=C1 ARFWKBWXBMDBHD-UHFFFAOYSA-N 0.000 claims description 5
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
• 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 description 5
• 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 description 5
• VXTCELKLMRKJJC-UHFFFAOYSA-N 2-cyclopentyl-3-(3,4-difluorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=C(F)C(F)=CC=C1C1=C(CCNCC2)C2=NN1C1CCCC1 VXTCELKLMRKJJC-UHFFFAOYSA-N 0.000 claims description 5
• 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 description 5
• QJQVCIMYFOJBAG-UHFFFAOYSA-N 2-cyclopentyl-3-(4-fluorophenyl)-5-methyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1CNC(C)CC(=C2C=3C=CC(F)=CC=3)C1=NN2C1CCCC1 QJQVCIMYFOJBAG-UHFFFAOYSA-N 0.000 claims description 5
• WXXAEEWABMVOCW-UHFFFAOYSA-N 2-cyclopentyl-3-(4-fluorophenyl)-6-methyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C=1C=C(F)C=CC=1C1=C2CCN(C)CCC2=NN1C1CCCC1 WXXAEEWABMVOCW-UHFFFAOYSA-N 0.000 claims description 5
• WWVMOFCTQXGOSL-UHFFFAOYSA-N 2-cyclopentyl-3-(4-methoxyphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(OC)=CC=C1C1=C(CCNCC2)C2=NN1C1CCCC1 WWVMOFCTQXGOSL-UHFFFAOYSA-N 0.000 claims description 5
• GKOQTZCERQKJIL-UHFFFAOYSA-N 2-cyclopentyl-3-(4-methylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(C)=CC=C1C1=C(CCNCC2)C2=NN1C1CCCC1 GKOQTZCERQKJIL-UHFFFAOYSA-N 0.000 claims description 5
• YWDRKJSRKOKSPZ-UHFFFAOYSA-N 2-cyclopentyl-3-(furan-3-yl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1CCCC1N1C(C2=COC=C2)=C2CCNCCC2=N1 YWDRKJSRKOKSPZ-UHFFFAOYSA-N 0.000 claims description 5
• RDIWXHPRIFAFII-UHFFFAOYSA-N 2-cyclopentyl-3-phenyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1CCCC1N1C(C=2C=CC=CC=2)=C2CCNCCC2=N1 RDIWXHPRIFAFII-UHFFFAOYSA-N 0.000 claims description 5
• XWPJSQOMCNOCPX-UHFFFAOYSA-N 2-cyclopentyl-3-thiophen-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1CCCC1N1C(C=2SC=CC=2)=C2CCNCCC2=N1 XWPJSQOMCNOCPX-UHFFFAOYSA-N 0.000 claims description 5
• YMAWHDMSUKUZLY-UHFFFAOYSA-N 2-cyclopentyl-3-thiophen-3-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1CCCC1N1C(C2=CSC=C2)=C2CCNCCC2=N1 YMAWHDMSUKUZLY-UHFFFAOYSA-N 0.000 claims description 5
• PBVYEZOTEXRPPS-UHFFFAOYSA-N 2-cyclopentyl-7-methyl-3-(4-methylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C=1C=C(C)C=CC=1C1=C2CCNC(C)CC2=NN1C1CCCC1 PBVYEZOTEXRPPS-UHFFFAOYSA-N 0.000 claims description 5
• PBQBRLIQOZTBLD-UHFFFAOYSA-N 2-ethyl-3-(4-ethylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(CC)=CC=C1C1=C(CCNCC2)C2=NN1CC PBQBRLIQOZTBLD-UHFFFAOYSA-N 0.000 claims description 5
• GIGGCXZVWCJOCZ-UHFFFAOYSA-N 2-pentan-3-yl-3-phenyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCC(CC)N1N=C2CCNCCC2=C1C1=CC=CC=C1 GIGGCXZVWCJOCZ-UHFFFAOYSA-N 0.000 claims description 5
• LFTJWRYLGBMUCY-UHFFFAOYSA-N 2-pentan-3-yl-3-thiophen-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCC(CC)N1N=C2CCNCCC2=C1C1=CC=CS1 LFTJWRYLGBMUCY-UHFFFAOYSA-N 0.000 claims description 5
• KMWKKNKEWFFTPO-UHFFFAOYSA-N 2-propan-2-yl-3-[4-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2CCNCCC2=C1C1=CC=C(C(F)(F)F)C=C1 KMWKKNKEWFFTPO-UHFFFAOYSA-N 0.000 claims description 5
• QPQPXZQRZGVLOY-UHFFFAOYSA-N 2-tert-butyl-3-(4-fluorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)(C)N1N=C2CCNCCC2=C1C1=CC=C(F)C=C1 QPQPXZQRZGVLOY-UHFFFAOYSA-N 0.000 claims description 5
• BMBDVPYNNCFDNT-UHFFFAOYSA-N 2-tert-butyl-3-phenyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)(C)N1N=C2CCNCCC2=C1C1=CC=CC=C1 BMBDVPYNNCFDNT-UHFFFAOYSA-N 0.000 claims description 5
• DEZIMNBAAODZEL-UHFFFAOYSA-N 3-(3-fluorophenyl)-2-pentan-3-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCC(CC)N1N=C2CCNCCC2=C1C1=CC=CC(F)=C1 DEZIMNBAAODZEL-UHFFFAOYSA-N 0.000 claims description 5
• CIIRPRURJVUQJE-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(3-fluoro-4-methoxyphenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=C(F)C(OC)=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 CIIRPRURJVUQJE-UHFFFAOYSA-N 0.000 claims description 5
• UYQGFNFIDOBWPC-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(2-methylpropyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)CN1N=C2CCNCCC2=C1C1=CC=C(Cl)C=C1 UYQGFNFIDOBWPC-UHFFFAOYSA-N 0.000 claims description 5
• HLANKXFVKACZMS-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-cyclohexyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C1=C(CCNCC2)C2=NN1C1CCCCC1 HLANKXFVKACZMS-UHFFFAOYSA-N 0.000 claims description 5
• DGXOEQXJGRVGTM-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-cyclopentyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C1=C(CCNCC2)C2=NN1C1CCCC1 DGXOEQXJGRVGTM-UHFFFAOYSA-N 0.000 claims description 5
• HCYYQTSWPWEMHS-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-ethyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCN1N=C2CCNCCC2=C1C1=CC=C(Cl)C=C1 HCYYQTSWPWEMHS-UHFFFAOYSA-N 0.000 claims description 5
• XSAFPPQZQQQNGU-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2CCNCCC2=C1C1=CC=C(Cl)C=C1 XSAFPPQZQQQNGU-UHFFFAOYSA-N 0.000 claims description 5
• HXAOXQVRMJLJNW-UHFFFAOYSA-N 3-(4-ethylphenyl)-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(CC)=CC=C1C1=C(CCNCC2)C2=NN1C(C)C HXAOXQVRMJLJNW-UHFFFAOYSA-N 0.000 claims description 5
• NVPSINMDGWJDFN-UHFFFAOYSA-N 3-(4-fluorophenyl)-2-pentan-3-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCC(CC)N1N=C2CCNCCC2=C1C1=CC=C(F)C=C1 NVPSINMDGWJDFN-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• VMLAIZMHNUQKOX-UHFFFAOYSA-N 3-(4-fluorophenyl)-8-methyl-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2C(C)CNCCC2=C1C1=CC=C(F)C=C1 VMLAIZMHNUQKOX-UHFFFAOYSA-N 0.000 claims description 5
• HFAGGJZWKFFGLM-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(OC)=CC=C1C1=C(CCNCC2)C2=NN1C(C)C HFAGGJZWKFFGLM-UHFFFAOYSA-N 0.000 claims description 5
• OLFYDDVREGSNQJ-UHFFFAOYSA-N 3-(4-methylphenyl)-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2CCNCCC2=C1C1=CC=C(C)C=C1 OLFYDDVREGSNQJ-UHFFFAOYSA-N 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• NIWHNGNRHRNLLP-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-1-yl]methyl]-2-fluorophenol Chemical compound C1=C(F)C(O)=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 NIWHNGNRHRNLLP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
• MIMUVOIVGRYXPO-UHFFFAOYSA-N 5-methyl-3-phenyl-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2CCNC(C)CC2=C1C1=CC=CC=C1 MIMUVOIVGRYXPO-UHFFFAOYSA-N 0.000 claims description 5
• HSFQLELKSBFMKV-UHFFFAOYSA-N 7-methyl-3-(4-methylphenyl)-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2CC(C)NCCC2=C1C1=CC=C(C)C=C1 HSFQLELKSBFMKV-UHFFFAOYSA-N 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• AZRCZQSGEJOJKS-UHFFFAOYSA-N 1-benzyl-3-(4-chlorophenyl)-6-ethyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1=2CCN(CC)CCC=2C(C=2C=CC(Cl)=CC=2)=NN1CC1=CC=CC=C1 AZRCZQSGEJOJKS-UHFFFAOYSA-N 0.000 claims description 4
• FPZBBELNXZMZNO-UHFFFAOYSA-N 1-benzyl-3-(4-chlorophenyl)-6-methyl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1=2CCN(C)CCC=2C(C=2C=CC(Cl)=CC=2)=NN1CC1=CC=CC=C1 FPZBBELNXZMZNO-UHFFFAOYSA-N 0.000 claims description 4
• MXOUMFAGXNVEAJ-UHFFFAOYSA-N 2,3-diphenyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C=12CCNCCC2=NN(C=2C=CC=CC=2)C=1C1=CC=CC=C1 MXOUMFAGXNVEAJ-UHFFFAOYSA-N 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
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• GTRPGHYMSGWGSO-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(2-phenylethyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C1=C(CCNCC2)C2=NN1CCC1=CC=CC=C1 GTRPGHYMSGWGSO-UHFFFAOYSA-N 0.000 claims description 2
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• 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
• FGPSVUCVCSPAMT-UHFFFAOYSA-N 4-(1-benzyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-3-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C(C=1CCNCCC=11)=NN1CC1=CC=CC=C1 FGPSVUCVCSPAMT-UHFFFAOYSA-N 0.000 claims description 2
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• SUWHADDRUGHITN-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-1-yl]methyl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 SUWHADDRUGHITN-UHFFFAOYSA-N 0.000 claims description 2
• LLVKSSHUBUGKBH-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-1-yl]methyl]phenol Chemical compound C1=CC(O)=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 LLVKSSHUBUGKBH-UHFFFAOYSA-N 0.000 claims description 2
• UZRATJRWDKFMAO-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-1-yl]pentanoic acid Chemical compound C1=2CCNCCC=2N(CCCCC(=O)O)N=C1C1=CC=C(Cl)C=C1 UZRATJRWDKFMAO-UHFFFAOYSA-N 0.000 claims description 2
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• CHKDVLNFSJAPNF-UHFFFAOYSA-N 5-[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-2-yl]pentanoic acid Chemical compound OC(=O)CCCCN1N=C2CCNCCC2=C1C1=CC=C(Cl)C=C1 CHKDVLNFSJAPNF-UHFFFAOYSA-N 0.000 claims description 2
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• KLRPPWWXISTWBW-UHFFFAOYSA-N 6-benzyl-3-(4-fluorophenyl)-8-methyl-2-propan-2-yl-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine Chemical compound C1CC2=C(C=3C=CC(F)=CC=3)N(C(C)C)N=C2C(C)CN1CC1=CC=CC=C1 KLRPPWWXISTWBW-UHFFFAOYSA-N 0.000 claims description 2
• LQLNUPNZJRFAFT-UHFFFAOYSA-N 7-methyl-3-phenyl-2-propan-2-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC(C)N1N=C2CC(C)NCCC2=C1C1=CC=CC=C1 LQLNUPNZJRFAFT-UHFFFAOYSA-N 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-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
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
• 229910002651 NO3 Inorganic materials 0.000 claims description 2
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
• 229910019142 PO4 Inorganic materials 0.000 claims description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
• 125000000732 arylene group Chemical group 0.000 claims description 2
• 125000003725 azepanyl group Chemical group 0.000 claims description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
• FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 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
• CELDKMHGHKIPMR-UHFFFAOYSA-N ethyl 5-[[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-2-yl]methyl]furan-2-carboxylate Chemical compound O1C(C(=O)OCC)=CC=C1CN1C(C=2C=CC(Cl)=CC=2)=C2CCNCCC2=N1 CELDKMHGHKIPMR-UHFFFAOYSA-N 0.000 claims description 2
• IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 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
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
• AFGXXQVAUXGYIN-UHFFFAOYSA-N methyl 2-[1-benzyl-3-(4-chlorophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepin-6-yl]acetate Chemical compound C1CN(CC(=O)OC)CCC(C(=N2)C=3C=CC(Cl)=CC=3)=C1N2CC1=CC=CC=C1 AFGXXQVAUXGYIN-UHFFFAOYSA-N 0.000 claims description 2
• BMFAXTLZTXUOMW-UHFFFAOYSA-N methyl 2-[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-1-yl]acetate Chemical compound C1=2CCNCCC=2N(CC(=O)OC)N=C1C1=CC=C(Cl)C=C1 BMFAXTLZTXUOMW-UHFFFAOYSA-N 0.000 claims description 2
• PKSYUIFNVQQCQT-UHFFFAOYSA-N methyl 4-[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-1-yl]butanoate Chemical compound C1=2CCNCCC=2N(CCCC(=O)OC)N=C1C1=CC=C(Cl)C=C1 PKSYUIFNVQQCQT-UHFFFAOYSA-N 0.000 claims description 2
• DLJBPWPSMSPEPV-UHFFFAOYSA-N methyl 4-[3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepin-2-yl]butanoate Chemical compound COC(=O)CCCN1N=C2CCNCCC2=C1C1=CC=C(Cl)C=C1 DLJBPWPSMSPEPV-UHFFFAOYSA-N 0.000 claims description 2
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