MXPA06003150A - Compuestos heterociclicos fusionados. - Google Patents
Compuestos heterociclicos fusionados.Info
- Publication number
- MXPA06003150A MXPA06003150A MXPA06003150A MXPA06003150A MXPA06003150A MX PA06003150 A MXPA06003150 A MX PA06003150A MX PA06003150 A MXPA06003150 A MX PA06003150A MX PA06003150 A MXPA06003150 A MX PA06003150A MX PA06003150 A MXPA06003150 A MX PA06003150A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- alkyl
- triaza
- hexahydro
- azulene
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 230000001404 mediated effect Effects 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 9
- 229940076279 serotonin Drugs 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 490
- -1 -O- phenyl Chemical group 0.000 claims description 389
- 229910052799 carbon Inorganic materials 0.000 claims description 270
- 125000000217 alkyl group Chemical group 0.000 claims description 248
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 237
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 123
- 125000004432 carbon atom Chemical group C* 0.000 claims description 118
- 150000001721 carbon Chemical group 0.000 claims description 117
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 113
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 108
- 229910052739 hydrogen Inorganic materials 0.000 claims description 91
- 125000001424 substituent group Chemical group 0.000 claims description 82
- 125000004076 pyridyl group Chemical group 0.000 claims description 70
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 60
- 150000002367 halogens Chemical class 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 48
- 150000002148 esters Chemical class 0.000 claims description 46
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 45
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 44
- 239000004215 Carbon black (E152) Substances 0.000 claims description 40
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 40
- 150000001408 amides Chemical class 0.000 claims description 40
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 40
- 229930195733 hydrocarbon Natural products 0.000 claims description 40
- 150000002430 hydrocarbons Chemical class 0.000 claims description 40
- 125000002950 monocyclic group Chemical group 0.000 claims description 40
- 125000006413 ring segment Chemical group 0.000 claims description 40
- 230000029936 alkylation Effects 0.000 claims description 39
- 238000005804 alkylation reaction Methods 0.000 claims description 39
- 229910052705 radium Inorganic materials 0.000 claims description 39
- 229910052701 rubidium Inorganic materials 0.000 claims description 39
- 125000003342 alkenyl group Chemical group 0.000 claims description 38
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
- 125000001544 thienyl group Chemical group 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 125000002541 furyl group Chemical group 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 17
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 230000027455 binding Effects 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 125000002971 oxazolyl group Chemical group 0.000 claims description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 12
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 12
- 125000002947 alkylene group Chemical group 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 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 11
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
- 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 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 10
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
- 125000004419 alkynylene group Chemical group 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 8
- 230000036506 anxiety Effects 0.000 claims description 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000002837 carbocyclic group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 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 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([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
- 208000019116 sleep disease Diseases 0.000 claims description 6
- 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 5
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 5
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 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
- 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 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
- 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 4
- UIWBGBFTZRIVOF-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(2-methylpropyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=2CCNCCC=2N(CC(C)C)N=C1C1=CC=C(Cl)C=C1 UIWBGBFTZRIVOF-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=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
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 206010012335 Dependence Diseases 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence 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
- 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
- 230000030135 gastric motility Effects 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
- 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
- 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
- 231100000872 sexual dysfunction Toxicity 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
- XUXGBEZZQHXETG-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-phenyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C=CC=CC=2)=C2CCNCCC2=N1 XUXGBEZZQHXETG-UHFFFAOYSA-N 0.000 claims description 3
- BLWAJWFMWZDRJP-UHFFFAOYSA-N 2-cyclohexyl-3-(4-fluorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(F)=CC=C1C1=C(CCNCC2)C2=NN1C1CCCCC1 BLWAJWFMWZDRJP-UHFFFAOYSA-N 0.000 claims description 3
- SAHZZRIGWQLBMK-UHFFFAOYSA-N 2-ethyl-3-(4-methoxyphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCN1N=C2CCNCCC2=C1C1=CC=C(OC)C=C1 SAHZZRIGWQLBMK-UHFFFAOYSA-N 0.000 claims description 3
- ZARNOPGRRXQZGC-UHFFFAOYSA-N 2-ethyl-3-(4-propan-2-ylphenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCN1N=C2CCNCCC2=C1C1=CC=C(C(C)C)C=C1 ZARNOPGRRXQZGC-UHFFFAOYSA-N 0.000 claims description 3
- ODIHMDQCEQGYAH-UHFFFAOYSA-N 2-pentan-3-yl-3-thiophen-3-yl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CCC(CC)N1N=C2CCNCCC2=C1C=1C=CSC=1 ODIHMDQCEQGYAH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- AJCZPQWTIPYDFG-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-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(Cl)=C1 AJCZPQWTIPYDFG-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- UUWHVKPIADRQCX-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(3-methylphenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC1=CC=CC(CN2C=3CCNCCC=3C(=N2)C=2C=CC(Cl)=CC=2)=C1 UUWHVKPIADRQCX-UHFFFAOYSA-N 0.000 claims description 3
- FYXPDJSNQKHAJC-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-cyclobutyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C(C=1CCNCCC=11)=NN1C1CCC1 FYXPDJSNQKHAJC-UHFFFAOYSA-N 0.000 claims description 3
- UYAQBYKCVBOSOK-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-cyclobutyl-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C1=C(CCNCC2)C2=NN1C1CCC1 UYAQBYKCVBOSOK-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
- 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 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
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- 238000011200 topical administration Methods 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- 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
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| PCT/US2004/030190 WO2005040169A2 (en) | 2003-09-17 | 2004-09-15 | Fused heterocyclic compounds as serotonin receptor modulators |
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| US20080161419A1 (en) * | 2004-02-20 | 2008-07-03 | Shinobu Akuzawa | Prophylactic Antimigraine Agents |
| CN1980710B (zh) * | 2004-06-30 | 2013-06-12 | 阿特西斯公司 | 作为5-羟色胺受体调节剂的取代的氮杂环庚烯衍生物 |
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| JP2008540574A (ja) | 2005-05-11 | 2008-11-20 | タケダ サン ディエゴ インコーポレイテッド | ヒストンデアセチラーゼ阻害剤 |
| GB0513886D0 (en) * | 2005-07-06 | 2005-08-10 | Glaxo Group Ltd | Novel compounds |
| NZ565334A (en) * | 2005-08-04 | 2010-12-24 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| US7598255B2 (en) * | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| US8076348B2 (en) | 2005-08-08 | 2011-12-13 | Astellas Pharma Inc. | Acylguanidine derivative or salt thereof |
| EP1981337B1 (en) * | 2006-01-19 | 2015-09-02 | Athersys, Inc. | Thiophenyl azepines as serotonin 5-ht2c receptor ligands and uses thereof |
| US8012957B2 (en) | 2006-03-27 | 2011-09-06 | Janssen Pharmaceutica Nv | Tetrahydro-1H-1,2,6-triaza-azulene cannabinoid modulators |
| US7915404B2 (en) | 2006-05-05 | 2011-03-29 | Janssen Pharmaceutica Nv | Methods for the preparation of pyrazole-containing compounds |
| US20100029617A1 (en) * | 2006-08-28 | 2010-02-04 | Actelion Pharmaceuticals Ltd. | 1,4,5,6,7,8-hexahydro-1,2,5-triaza-azulene derivatives as orexin receptor antagonists |
| WO2009058810A1 (en) * | 2007-11-02 | 2009-05-07 | Janssen Pharmaceutica N.V. | Process for the preparation of substituted 2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene derivatives |
| US8404863B2 (en) | 2008-01-03 | 2013-03-26 | Allergan, Inc. | Tetrahydroindoles having sphingosine-1-phosphate receptor activity |
| US8829011B2 (en) | 2008-10-29 | 2014-09-09 | Janssen Pharmaceutica Nv | 2-aminopyrimidine compounds as serotonin receptor modulators |
| CA2739900C (en) | 2008-11-18 | 2016-11-08 | F. Hoffmann-La Roche Ag | Alkylcyclohexylethers of dihydrotetraazabenzoazulenes |
| US8309578B2 (en) * | 2008-11-25 | 2012-11-13 | Nerviano Medical Sciences S.R.L. | Bicyclic pyrazole and isoxazole derivatives as antitumor and antineurodegenerative agents |
| US8492374B2 (en) * | 2009-04-29 | 2013-07-23 | Industrial Technology Research Institute | Azaazulene compounds |
| GB201004311D0 (en) | 2010-03-15 | 2010-04-28 | Proximagen Ltd | New enzyme inhibitor compounds |
| KR101911974B1 (ko) | 2011-04-21 | 2018-10-25 | 바스프 에스이 | 신규 살충 피라졸 화합물 |
| SG11201400277VA (en) | 2011-09-14 | 2014-05-29 | Proximagen Ltd | New enzyme inhibitor compounds |
| WO2013156318A1 (en) | 2012-04-16 | 2013-10-24 | Basf Se | Substituted pesticidal pyrazole compounds |
| ES2660132T3 (es) | 2012-06-20 | 2018-03-20 | Basf Se | Compuestos de pirazol plaguicidas |
| PE20151139A1 (es) * | 2012-08-16 | 2015-08-07 | Janssen Pharmaceutica Nv | Pirrolopirazoles como bloqueadores del canal de calcio tipo n |
| WO2014063942A1 (en) | 2012-10-23 | 2014-05-01 | Basf Se | Substituted pesticidal pyrazole compounds |
| SG11201504749TA (en) | 2012-12-21 | 2015-07-30 | Abt Holding Co | Benzazepines as serotonin 5-ht2c receptor ligands and uses thereof |
| WO2014159067A1 (en) | 2013-03-13 | 2014-10-02 | Abt Holding Company | Thienylindole azepines as serotonin 5-ht2c receptor ligands and uses thereof |
| US9453002B2 (en) | 2013-08-16 | 2016-09-27 | Janssen Pharmaceutica Nv | Substituted imidazoles as N-type calcium channel blockers |
| WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
| EP3221321B1 (en) * | 2014-11-21 | 2021-12-15 | Akarna Therapeutics, Ltd. | Fused bicyclic compounds for the treatment of disease |
| EP3256450B1 (en) * | 2015-02-11 | 2020-12-02 | Merck Sharp & Dohme Corp. | Substituted pyrazole compounds as ror-gamma-t inhibitors and uses thereof |
| CN105503647A (zh) * | 2015-12-10 | 2016-04-20 | 苏州昊帆生物科技有限公司 | 环丙基肼盐酸盐的制备方法 |
| US9951039B2 (en) * | 2016-04-08 | 2018-04-24 | The Hong Kong Polytechnic University | Pyrimidines for treatment of bacterial infections |
| KR101917264B1 (ko) * | 2016-12-22 | 2018-11-13 | 한국과학기술연구원 | 5-ht7 수용체 조절제로 작용하는 아제핀 유도체 |
| KR102037494B1 (ko) | 2017-12-11 | 2019-10-28 | 씨제이헬스케어 주식회사 | 광학활성을 갖는 피페리딘 유도체의 중간체 및 이의 제조방법 |
| WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
| CN112300169B (zh) * | 2019-07-26 | 2022-03-04 | 上海美迪西生物医药股份有限公司 | 吡咯并吡唑类衍生物、其制备方法及其在医药上的应用 |
| KR20190120112A (ko) | 2019-10-08 | 2019-10-23 | 씨제이헬스케어 주식회사 | 광학활성을 갖는 피페리딘 유도체의 중간체 및 이의 제조방법 |
| EP4105206A4 (en) * | 2020-01-13 | 2024-08-14 | Aptabio Therapeutics Inc. | NOVEL PYRAZOLE DERIVATIVE |
| PH12022552056A1 (en) | 2020-02-07 | 2024-02-12 | Gasherbrum Bio Inc | Heterocyclic glp-1 agonists |
| EP4665730A1 (en) | 2023-02-16 | 2025-12-24 | Gasherbrum Bio, Inc. | Heterocyclic glp-1 agonists |
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