NZ545836A - Fused heterocyclic compounds as serotonin receptor modulators - Google Patents
Fused heterocyclic compounds as serotonin receptor modulatorsInfo
- Publication number
- NZ545836A NZ545836A NZ545836A NZ54583604A NZ545836A NZ 545836 A NZ545836 A NZ 545836A NZ 545836 A NZ545836 A NZ 545836A NZ 54583604 A NZ54583604 A NZ 54583604A NZ 545836 A NZ545836 A NZ 545836A
- Authority
- NZ
- New Zealand
- Prior art keywords
- phenyl
- triaza
- chloro
- azulene
- hexahydro
- Prior art date
Links
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title claims abstract description 13
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 title claims abstract description 13
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- -1 diastereomers Chemical class 0.000 claims abstract description 216
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 150000001408 amides Chemical class 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 9
- 230000000694 effects Effects 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 7
- 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 abstract description 6
- 150000004677 hydrates Chemical class 0.000 claims abstract description 6
- 239000012453 solvate Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract 8
- 230000002265 prevention Effects 0.000 claims abstract 6
- 208000015114 central nervous system disease Diseases 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims description 46
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052701 rubidium Inorganic materials 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 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
- 208000035475 disorder Diseases 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000006413 ring segment Chemical group 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 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
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 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
- 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
- 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
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 125000005605 benzo group Chemical group 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
- 230000001404 mediated effect Effects 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- WPHGSKGZRAQSGP-UHFFFAOYSA-N norcarane Chemical compound C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 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
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000001412 tetrahydropyranyl 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
- 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
- SLNWWYNQLZSUHK-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(2,4-difluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound FC1=CC(F)=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 SLNWWYNQLZSUHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 2
- MASWQYAPUWTJNT-UHFFFAOYSA-N 1-[(2-bromophenyl)methyl]-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=C1Br MASWQYAPUWTJNT-UHFFFAOYSA-N 0.000 claims description 2
- KPRBIOBDPJTPRG-UHFFFAOYSA-N 1-[(3-bromophenyl)methyl]-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(Br)=C1 KPRBIOBDPJTPRG-UHFFFAOYSA-N 0.000 claims description 2
- JTLKOCQOBQJLFP-UHFFFAOYSA-N 1-[(4-bromophenyl)methyl]-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=C(Br)C=C1 JTLKOCQOBQJLFP-UHFFFAOYSA-N 0.000 claims description 2
- SCGMQAOBNMAEBR-UHFFFAOYSA-N 1-but-3-enyl-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C1=NN(CCC=C)C2=C1CCNCC2 SCGMQAOBNMAEBR-UHFFFAOYSA-N 0.000 claims description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 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
- XSLUDLWEZBOKLW-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(cyclohexylmethyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C(C=1CCNCCC=11)=NN1CC1CCCCC1 XSLUDLWEZBOKLW-UHFFFAOYSA-N 0.000 claims description 2
- CEJAXTGGUGQRCX-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-(oxan-4-ylmethyl)-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=CC(Cl)=CC=C1C(C=1CCNCCC=11)=NN1CC1CCOCC1 CEJAXTGGUGQRCX-UHFFFAOYSA-N 0.000 claims description 2
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- UDHJFBWEINQGHQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(2-methoxyphenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound COC1=CC=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 UDHJFBWEINQGHQ-UHFFFAOYSA-N 0.000 claims description 2
- KCIXJLHEJPJVCP-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(2-methylphenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound CC1=CC=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 KCIXJLHEJPJVCP-UHFFFAOYSA-N 0.000 claims description 2
- OSYXZOHVXOWZIH-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(3,4-difluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=C(F)C(F)=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 OSYXZOHVXOWZIH-UHFFFAOYSA-N 0.000 claims description 2
- HZKULMVGNNLUPZ-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(3,4-dimethylphenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound C1=C(C)C(C)=CC=C1CN1C(CCNCC2)=C2C(C=2C=CC(Cl)=CC=2)=N1 HZKULMVGNNLUPZ-UHFFFAOYSA-N 0.000 claims description 2
- WHGQWMKZHVRSLF-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-[(3-fluorophenyl)methyl]-5,6,7,8-tetrahydro-4h-pyrazolo[3,4-d]azepine Chemical compound FC1=CC=CC(CN2C=3CCNCCC=3C(=N2)C=2C=CC(Cl)=CC=2)=C1 WHGQWMKZHVRSLF-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
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- 229910002651 NO3 Inorganic materials 0.000 claims description 2
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Classifications
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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
- C07D471/04—Ortho-condensed systems
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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| WO2005079845A1 (ja) * | 2004-02-20 | 2005-09-01 | Astellas Pharma Inc. | 片頭痛予防薬 |
| EP1778243B1 (en) * | 2004-06-30 | 2012-10-31 | Athersys, Inc. | Substituted azepine derivatives as serotonin receptor modulators |
| EP1824831A2 (en) | 2004-12-16 | 2007-08-29 | Takeda San Diego, Inc. | Histone deacetylase inhibitors |
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| GB0513886D0 (en) * | 2005-07-06 | 2005-08-10 | Glaxo Group Ltd | Novel compounds |
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| ES2371106T3 (es) * | 2005-08-08 | 2011-12-27 | Astellas Pharma Inc. | Derivado de acilguanidina o sal del mismo. |
| EP1981337B1 (en) | 2006-01-19 | 2015-09-02 | Athersys, Inc. | Thiophenyl azepines as serotonin 5-ht2c receptor ligands and uses thereof |
| WO2007112402A1 (en) * | 2006-03-27 | 2007-10-04 | Janssen Pharmaceutica N.V. | Tetrahydro-1h-1,2,6-triaza-azulene cannabinoid modulators |
| CN101479252B (zh) * | 2006-05-05 | 2014-01-29 | 詹森药业有限公司 | 用于制备含吡唑的化合物的方法 |
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| WO2009085847A1 (en) * | 2008-01-03 | 2009-07-09 | Allergan, Inc. | Tetrahydroindoles having sphingosine-1-phosphate receptor activity |
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| MX370480B (es) * | 2014-11-21 | 2019-12-16 | Akarna Therapeutics Ltd | Compuestos bicíclicos fusionados para el tratamiento de enfermedades. |
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| 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 |
| WO2017175045A1 (en) * | 2016-04-08 | 2017-10-12 | 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 |
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| 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 |
| US20230067461A1 (en) * | 2020-01-13 | 2023-03-02 | Aptabio Therapeutics Inc. | Novel pyrazole derivative |
| FI4097099T3 (fi) | 2020-02-07 | 2024-07-30 | Gasherbrum Bio Inc | Heterosyklisiä glp-1-agonisteja |
| IL322686A (en) | 2023-02-16 | 2025-10-01 | Gasherbrum Bio Inc | Heterocyclic glp-1 agonists |
Family Cites Families (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1197466B (de) * | 1962-03-22 | 1965-07-29 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen 5, 6, 7, 8-Tetrahydropyrido-[4, 3-d]pyrimidinen |
| US3312716A (en) * | 1964-08-11 | 1967-04-04 | Aldrich Chem Co Inc | 4-hydroxy-3-pyrrolidinemethanols |
| GB1422263A (en) * | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| US4314081A (en) * | 1974-01-10 | 1982-02-02 | Eli Lilly And Company | Arloxyphenylpropylamines |
| GB1484140A (en) * | 1974-04-24 | 1977-08-24 | Wyeth John & Brother Ltd | Pyrrolopyridine derivatives |
| US3969355A (en) * | 1974-11-01 | 1976-07-13 | Morton-Norwich Products, Inc. | 5-Aminoethyl-2,4-diphenylpyrimidine dihydrobromide |
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| US4536518A (en) * | 1979-11-01 | 1985-08-20 | Pfizer Inc. | Antidepressant derivatives of cis-4-phenyl-1,2,3,4-tetrahydro-1-naphthalenamine |
| DK27383A (da) * | 1982-02-17 | 1983-08-18 | Lepetit Spa | Fremgangsmaade til fremstilling af pyrazol(4,3-c)pyridiner |
| US4673405A (en) * | 1983-03-04 | 1987-06-16 | Alza Corporation | Osmotic system with instant drug availability |
| US4576604A (en) * | 1983-03-04 | 1986-03-18 | Alza Corporation | Osmotic system with instant drug availability |
| US4857330A (en) * | 1986-04-17 | 1989-08-15 | Alza Corporation | Chlorpheniramine therapy |
| JPH03148265A (ja) | 1989-11-01 | 1991-06-25 | Sumitomo Chem Co Ltd | ５，７―ジフェニル―４，６―ジアザインダン誘導体、その製造法およびそれを有効成分とする除草剤 |
| US5137890A (en) * | 1990-02-14 | 1992-08-11 | Ortho Pharmaceutical Corporation | 4-phenyl tetrahydropyrido(4,3-d)pyrimidines |
| US5053508A (en) | 1990-03-09 | 1991-10-01 | American Home Products Corporation | Fused heterotricyclic imides with psychotropic activity and intermedrates thereof |
| US5648352A (en) * | 1991-09-13 | 1997-07-15 | Merck & Co., Inc. | Piperazinylcamphorsulfonyl oxytocin antagonists |
| US5612356A (en) | 1992-12-28 | 1997-03-18 | Eisai Co., Ltd. | Heterocycle-containing carbonic acid derivatives |
| US6677310B1 (en) * | 1999-04-21 | 2004-01-13 | Nabi | Ring-expanded nucleosides and nucleotides |
| US5843912A (en) * | 1994-07-06 | 1998-12-01 | Universy Of Maryland | Ring-expanded nucleosides and nucleotides |
| US5405848A (en) * | 1993-12-22 | 1995-04-11 | Ortho Pharmaceutical Corporation | Substituted thiazolylaminotetrahydropyridopyrimidines derivatives useful as platelet aggregation inhibitors |
| US5663178A (en) * | 1995-02-06 | 1997-09-02 | Eli Lilly And Company | Tetrahydro-beta carbolines |
| JP3004728B2 (ja) | 1994-04-29 | 2000-01-31 | ファイザー インク． | 神経伝達物質放出増強薬としての新規な非環式および環式アミド類 |
| AU5317996A (en) | 1995-04-18 | 1996-11-07 | Eli Lilly And Company | Method for using ergoline compounds to effect physiological and pathological functions at the 5-ht7 receptor |
| WO1997029097A1 (en) | 1996-02-09 | 1997-08-14 | Smithkline Beecham Plc | Sulfonamide derivatives as 5ht7 receptor antagonists |
| TW470745B (en) * | 1996-05-23 | 2002-01-01 | Janssen Pharmaceutica Nv | Hexahydro-pyrido[4,3-b]indole derivatives |
| AU2980797A (en) | 1996-06-11 | 1998-01-07 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and medicinal uses thereof |
| GB9612884D0 (en) | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
| JP2000512646A (ja) | 1996-06-25 | 2000-09-26 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５ｈｔ７受容体アンタゴニストとしてのスルホンアミド誘導体 |
| US6355642B1 (en) * | 1996-06-28 | 2002-03-12 | Meiji Seika Kaisha, Ltd. | Tetrahydrobenzindole compounds |
| GB9700899D0 (en) | 1997-01-17 | 1997-03-05 | Smithkline Beecham Plc | Novel treatment |
| JP2001514631A (ja) | 1997-03-07 | 2001-09-11 | ノボ ノルディスク アクティーゼルスカブ | ４，５，６，７−テトラヒドロ−チエノ［３，２−ｃ］ピリジン誘導体類、それらの製造方法及び使用 |
| US6177443B1 (en) * | 1997-03-07 | 2001-01-23 | Novo Nordisk A/S | 4,5,6,7-tetrahydro-thieno[3, 2-C]pyridine derivatives, their preparation and use |
| EP0905136A1 (en) * | 1997-09-08 | 1999-03-31 | Janssen Pharmaceutica N.V. | Tetrahydro gamma-carbolines |
| US5951518A (en) | 1997-10-31 | 1999-09-14 | Teleflex, Incorporated | Introducing device with flared sheath end |
| WO1999024022A2 (en) | 1997-11-10 | 1999-05-20 | F. Hoffmann-La Roche Ag | Isoquinoline derivatives for treating disorders associated with 5ht7 receptors |
| US6407112B1 (en) * | 1998-04-22 | 2002-06-18 | Meiji Seika Kaisha, Ltd. | Optically active tetrahydrobenzindole derivative |
| JP2002516282A (ja) | 1998-05-22 | 2002-06-04 | イーライ・リリー・アンド・カンパニー | 難治性鬱病の処置のための組合せ治療 |
| US5997905A (en) * | 1998-09-04 | 1999-12-07 | Mcneil-Ppc | Preparation of pharmaceutically active particles |
| AU1321900A (en) | 1998-10-23 | 2000-05-15 | Sepracor, Inc. | Compositions and methods employing r(-) fluoxetine and other active ingredients |
| US6245785B1 (en) | 1998-11-30 | 2001-06-12 | Warner Lambert Company | Dissolution of triprolidine hydrochloride |
| GB9828004D0 (en) | 1998-12-18 | 1999-02-10 | Smithkline Beecham Plc | Use |
| GB9906624D0 (en) | 1999-03-23 | 1999-05-19 | Smithkline Beecham Plc | Novel compounds |
| CA2366858A1 (en) * | 1999-04-01 | 2000-10-12 | Margaret Yuhua Chu-Moyer | Sorbitol dehydrogenase inhibitors |
| GB9912701D0 (en) | 1999-06-01 | 1999-08-04 | Smithkline Beecham Plc | Novel compounds |
| US6806230B1 (en) | 1999-09-09 | 2004-10-19 | Kumiai Chemical Industry Co., Ltd. | Pyrimidine derivatives and herbicides containing them |
| EP1222185A1 (en) | 1999-10-18 | 2002-07-17 | Smithkline Beecham Plc | Tetrahydrobenzindolone derivatives, their preparation and their use as 5-ht7 receptor antagonists |
| UA77650C2 (en) | 1999-12-06 | 2007-01-15 | Lundbeck & Co As H | Use of serotonin reuptake inhibitor in combination with deramcyclane |
| CA2399545A1 (en) | 2000-02-04 | 2001-08-09 | Michael Gerard Kelly | Pyrrolo-isoquinoline and tetrahydropyrrolo-isoquinoline derivatives and their use as mediators of the 5-ht7 receptor |
| AU2001241128A1 (en) | 2000-03-14 | 2001-09-24 | Fujisawa Pharmaceutical Co. Ltd. | Novel amide compounds |
| US6586469B2 (en) | 2000-07-25 | 2003-07-01 | Medpointe Healthcare Inc. | Antihistaminic/antitussive compositions |
| EP1309591B1 (en) | 2000-08-14 | 2007-01-24 | Ortho-McNeil Pharmaceutical, Inc. | Substituted pyrazoles |
| AU8870601A (en) * | 2000-09-06 | 2002-03-22 | Ortho Mcneil Pharm Inc | A method for treating allergies using substituted pyrazoles |
| US20040267010A1 (en) | 2001-02-02 | 2004-12-30 | Forbes Ian Thomson | Sulfonamide compounds, their preparation and use |
| HUP0303270A3 (en) * | 2001-02-21 | 2007-03-28 | Janssen Pharmaceutica Nv | Isoxazoline derivatives as anti-depressants, process for their preparation and pharmaceutical compositions containing them |
| US20020183519A1 (en) * | 2001-03-13 | 2002-12-05 | Herbert Nar | Antithrombotic carboxylic acid amides |
| DE10111842A1 (de) | 2001-03-13 | 2002-09-19 | Boehringer Ingelheim Pharma | Antithrombotische Carbonsäureamide, deren Herstellung und deren Verwendung als Arzneimittel |
| US6559174B2 (en) * | 2001-03-20 | 2003-05-06 | Merck & Co., Inc. | N-arylsulfonyl aryl aza-bicyclic derivatives as potent cell adhesion inhibitors |
| US6806380B2 (en) * | 2001-10-02 | 2004-10-19 | Lexicon Pharmaceuticals, Inc. | Modified safe and efficient process for the environmentally friendly synthesis of imidoesters |
| IL161576A0 (en) * | 2001-10-26 | 2004-09-27 | Aventis Pharma Inc | Benzimidazoles and analogues and their use as protein kinases inhibitors |
| US6806279B2 (en) | 2001-12-17 | 2004-10-19 | Sunesis Pharmaceuticals, Inc. | Small-molecule inhibitors of interleukin-2 |
| SE0104340D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New compounds |
| US20030199542A1 (en) * | 2002-04-18 | 2003-10-23 | Woods Keith W. | Farnesyltransferase inhibitors |
| US20030199544A1 (en) * | 2002-04-18 | 2003-10-23 | Woods Keith W. | Farnesyltransferase inhibitors |
| HRP20020452A2 (en) | 2002-05-23 | 2004-02-29 | Pliva D D | 1,2-diaza-dibenzoazulen as inhibitor of production of tumor necrosis factors and intermediates for preparation thereof |
| KR20050013562A (ko) * | 2002-05-30 | 2005-02-04 | 버텍스 파마슈티칼스 인코포레이티드 | Ｊａｋ 및 ｃｄｋ2 프로테인 키나아제의 억제제 |
| EP1545552B1 (en) * | 2002-06-20 | 2007-03-28 | H. Lundbeck A/S | Combination therapy wherein a serotonin reuptake inhibitor is used |
| AU2003244649A1 (en) | 2002-07-25 | 2004-02-23 | Pharmacia Italia Spa | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| CA2493625A1 (en) | 2002-07-25 | 2004-02-19 | Pharmacia Italia S.P.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| WO2004011467A1 (ja) | 2002-07-29 | 2004-02-05 | Hokko Chemical Industry Co., Ltd. | トリアゾロピリミジン誘導体および農園芸用殺菌剤 |
| US20040132826A1 (en) | 2002-10-25 | 2004-07-08 | Collegium Pharmaceutical, Inc. | Modified release compositions of milnacipran |
| AU2003274050A1 (en) | 2002-10-30 | 2004-05-25 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
| MXPA05008137A (es) * | 2003-01-31 | 2005-09-30 | Pfizer Prod Inc | Antagonistas y agonistas de 5ht7. |
| GB0308208D0 (en) | 2003-04-09 | 2003-05-14 | Glaxo Group Ltd | Chemical compounds |
| US7145012B2 (en) * | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| GB0316128D0 (en) | 2003-07-10 | 2003-08-13 | Univ Aston | Novel sulfonamide compounds |
| BRPI0412262A (pt) | 2003-07-23 | 2006-09-19 | X Ceptor Therapeutics Inc | derivados de azepina como agentes farmacêuticos |
| AU2004283196B2 (en) | 2003-09-17 | 2011-08-25 | Janssen Pharmaceutica, N.V. | Fused heterocyclic compounds |
| WO2005030776A1 (en) * | 2003-09-23 | 2005-04-07 | Vertex Pharmaceuticals Incorporated | Pyrazolopyrrole derivatives as protein kinase inhibitors |
| AU2004275777A1 (en) | 2003-09-24 | 2005-04-07 | Combinatorx, Incorporated | Therapeutic regimens for administering drug combinations |
| WO2005056056A2 (en) | 2003-12-15 | 2005-06-23 | H. Lundbeck A/S | The combination of a serotonin reuptake inhibitor and a histamine 3 receptor antagonist, inverse agonist or partial agonist |
| US20050232986A1 (en) * | 2003-12-17 | 2005-10-20 | David Brown | Dosage form containing promethazine and another drug |
| US20090227562A1 (en) | 2004-08-10 | 2009-09-10 | Pfizer Inc. | Combination of a Selective Noradrenaline Reuptake Unhibitor and a PDEV Inhibitor |
| US20060037652A1 (en) | 2004-08-23 | 2006-02-23 | Ranco Incorporated Of Delaware | Reversing valve assembly with improved pilot valve mounting structure |
| ATE496892T1 (de) * | 2004-12-17 | 2011-02-15 | Janssen Pharmaceutica Nv | Tetrahydroisochinolinverbindungen zur behandlung von zns-erkrankungen |
| PL1899334T3 (pl) * | 2005-06-17 | 2009-04-30 | Janssen Pharmaceutica Nv | Związki naftyrydynowe |
| AU2006259257A1 (en) * | 2005-06-17 | 2006-12-28 | Janssen Pharmaceutica N.V. | Hexahydro-pyrrolo-isoquinoline compounds for the treatment of CNS disorders |
| 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 |
| KR20080109841A (ko) * | 2006-03-10 | 2008-12-17 | 뉴로젠 코포레이션 | 피페라지닐 옥소알킬 테트라히드로이소퀴놀린 및 관련유사체 |
| CN101479252B (zh) * | 2006-05-05 | 2014-01-29 | 詹森药业有限公司 | 用于制备含吡唑的化合物的方法 |
| AU2007265239A1 (en) * | 2006-06-29 | 2008-01-03 | Janssen Pharmaceutica N.V. | Butyl and butynyl benzyl amine compounds |
| CN101511790A (zh) * | 2006-06-29 | 2009-08-19 | 詹森药业有限公司 | 取代的氨基甲基苯甲酰胺化合物 |
| EP2049473A2 (en) * | 2006-06-29 | 2009-04-22 | Janssen Pharmaceutica N.V. | Substituted benzyl amine compounds |
| WO2008064036A1 (en) * | 2006-11-16 | 2008-05-29 | Janssen Pharmaceutica N.V. | Substituted phenyl propyl amines as histamine h3 receptor and serotonin transporter modulators |
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