RU2378278C2 - ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ - Google Patents
ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ Download PDFInfo
- Publication number
- RU2378278C2 RU2378278C2 RU2008102155/04A RU2008102155A RU2378278C2 RU 2378278 C2 RU2378278 C2 RU 2378278C2 RU 2008102155/04 A RU2008102155/04 A RU 2008102155/04A RU 2008102155 A RU2008102155 A RU 2008102155A RU 2378278 C2 RU2378278 C2 RU 2378278C2
- Authority
- RU
- Russia
- Prior art keywords
- triazolo
- pyrimidine
- thieno
- amino
- quinazoline
- Prior art date
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- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 title claims abstract 26
- 239000005557 antagonist Substances 0.000 title claims abstract 10
- 150000001875 compounds Chemical class 0.000 title claims abstract 9
- 238000000034 method Methods 0.000 title claims abstract 7
- 229940076279 serotonin Drugs 0.000 title claims abstract 7
- 108091005435 5-HT6 receptors Proteins 0.000 title 1
- 150000004677 hydrates Chemical class 0.000 claims abstract 19
- 150000003839 salts Chemical class 0.000 claims abstract 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 10
- 239000001301 oxygen Chemical group 0.000 claims abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 10
- 125000005843 halogen group Chemical group 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002252 acyl group Chemical group 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000003277 amino group Chemical group 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 230000000694 effects Effects 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 3
- 239000001257 hydrogen Substances 0.000 claims abstract 3
- 230000001404 mediated effect Effects 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- -1 5-isopropylamino-3-tosylsulfonylthieno [2,3-e] [1,2,3] triazolo [1,5-a] pyrimidine Chemical compound 0.000 claims 24
- POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 claims 12
- 229910052717 sulfur Chemical group 0.000 claims 8
- 239000011593 sulfur Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- KUBPLNHBDKRQHU-UHFFFAOYSA-N hms1637l19 Chemical compound N1=NN2C=3C=CSC=3C(NCCCC)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KUBPLNHBDKRQHU-UHFFFAOYSA-N 0.000 claims 4
- LNKSDHUQNBRZCE-UHFFFAOYSA-N 10-(benzenesulfonyl)-N-methyl-5-thia-1,8,11,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaen-7-amine Chemical compound N1=NN2C=3C=CSC=3C(NC)=NC2=C1S(=O)(=O)C1=CC=CC=C1 LNKSDHUQNBRZCE-UHFFFAOYSA-N 0.000 claims 2
- ZGZCQCQUORBXAQ-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-N,N-dimethyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N1=NN2C3=CC=CC=C3C(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC(Cl)=C1 ZGZCQCQUORBXAQ-UHFFFAOYSA-N 0.000 claims 2
- FANLWIILNLEVRR-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-N-methyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N1=NN2C3=CC=CC=C3C(NC)=NC2=C1S(=O)(=O)C1=CC=CC(Cl)=C1 FANLWIILNLEVRR-UHFFFAOYSA-N 0.000 claims 2
- YABXAOXVRBMDEC-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyltriazolo[1,5-a]quinazoline Chemical compound ClC1=CC=CC(S(=O)(=O)C2=C3N(C4=CC=CC=C4C=N3)N=N2)=C1 YABXAOXVRBMDEC-UHFFFAOYSA-N 0.000 claims 2
- ZJVPAGHXCQGUEO-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfonyl-N,N-dimethyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N1=NN2C3=CC=CC=C3C(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC(F)=C1 ZJVPAGHXCQGUEO-UHFFFAOYSA-N 0.000 claims 2
- JLGPCEVKKULWNT-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfonyl-N-methyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N1=NN2C3=CC=CC=C3C(NC)=NC2=C1S(=O)(=O)C1=CC=CC(F)=C1 JLGPCEVKKULWNT-UHFFFAOYSA-N 0.000 claims 2
- XYZAXSLDCIYJQC-UHFFFAOYSA-N 3-(3-fluorophenyl)sulfonyltriazolo[1,5-a]quinazoline Chemical compound FC1=CC=CC(S(=O)(=O)C2=C3N(C4=CC=CC=C4C=N3)N=N2)=C1 XYZAXSLDCIYJQC-UHFFFAOYSA-N 0.000 claims 2
- OVNNXRSGYBMTQC-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-N-methyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N1=NN2C3=CC=CC=C3C(NC)=NC2=C1S(=O)(=O)C1=CC=C(F)C=C1 OVNNXRSGYBMTQC-UHFFFAOYSA-N 0.000 claims 2
- VYPWACMAHDABJK-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyltriazolo[1,5-a]quinazoline Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=C(N=CC=2C3=CC=CC=2)N3N=N1 VYPWACMAHDABJK-UHFFFAOYSA-N 0.000 claims 2
- ASJWWVCFDXTDAM-UHFFFAOYSA-N 3-(benzenesulfonyl)-n,n-dimethyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N1=NN2C3=CC=CC=C3C(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 ASJWWVCFDXTDAM-UHFFFAOYSA-N 0.000 claims 2
- IPQXYDJXIIDVGI-UHFFFAOYSA-N 3-(benzenesulfonyl)-n-(2-phenylethyl)triazolo[1,5-a]quinazolin-5-amine Chemical compound C=1C=CC=CC=1S(=O)(=O)C=1N=NN(C2=CC=CC=C22)C=1N=C2NCCC1=CC=CC=C1 IPQXYDJXIIDVGI-UHFFFAOYSA-N 0.000 claims 2
- AOMLPOXHZHVZSB-UHFFFAOYSA-N 3-(benzenesulfonyl)-n-methyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N1=NN2C3=CC=CC=C3C(NC)=NC2=C1S(=O)(=O)C1=CC=CC=C1 AOMLPOXHZHVZSB-UHFFFAOYSA-N 0.000 claims 2
- PRJBPLNAZJMZLE-UHFFFAOYSA-N 3-(benzenesulfonyl)triazolo[1,5-a]quinazoline Chemical compound N1=NN(C2=CC=CC=C2C=N2)C2=C1S(=O)(=O)C1=CC=CC=C1 PRJBPLNAZJMZLE-UHFFFAOYSA-N 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- OGSGQDOTSCYJOC-UHFFFAOYSA-N 5-thia-1,8,11,12-tetrazatricyclo[7.3.0.02,6]dodeca-2(6),3,7,9,11-pentaene Chemical compound C1=NC2=CN=NN2C2=C1SC=C2 OGSGQDOTSCYJOC-UHFFFAOYSA-N 0.000 claims 2
- KXPKLIHLBRZSOL-UHFFFAOYSA-N C1=CC(=CC(=C1)Cl)S(=O)(=O)C2=C3N=CC4=C(N3N=N2)C=CS4 Chemical compound C1=CC(=CC(=C1)Cl)S(=O)(=O)C2=C3N=CC4=C(N3N=N2)C=CS4 KXPKLIHLBRZSOL-UHFFFAOYSA-N 0.000 claims 2
- IOCBDJZKGIKQJG-UHFFFAOYSA-N C1=CC(=CC(=C1)S(=O)(=O)C2=C3N=CC4=C(N3N=N2)C=CS4)F Chemical compound C1=CC(=CC(=C1)S(=O)(=O)C2=C3N=CC4=C(N3N=N2)C=CS4)F IOCBDJZKGIKQJG-UHFFFAOYSA-N 0.000 claims 2
- VHXXTYFZKMONAQ-UHFFFAOYSA-N C1=CC(=CC=C1F)S(=O)(=O)C2=C3N=CC4=C(N3N=N2)C=CS4 Chemical compound C1=CC(=CC=C1F)S(=O)(=O)C2=C3N=CC4=C(N3N=N2)C=CS4 VHXXTYFZKMONAQ-UHFFFAOYSA-N 0.000 claims 2
- LCSVHMYKPLSSPL-UHFFFAOYSA-N CN(C)C1=NC2=C(N=NN2C3=C1SC=C3)S(=O)(=O)C4=CC(=CC=C4)Cl Chemical compound CN(C)C1=NC2=C(N=NN2C3=C1SC=C3)S(=O)(=O)C4=CC(=CC=C4)Cl LCSVHMYKPLSSPL-UHFFFAOYSA-N 0.000 claims 2
- ZEGURORDGMTEKK-UHFFFAOYSA-N CNC1=NC2=C(N=NN2C3=C1SC=C3)S(=O)(=O)C4=CC=CC(=C4)F Chemical compound CNC1=NC2=C(N=NN2C3=C1SC=C3)S(=O)(=O)C4=CC=CC(=C4)F ZEGURORDGMTEKK-UHFFFAOYSA-N 0.000 claims 2
- VXVAEKFZSCCONZ-UHFFFAOYSA-N CNC1=NC=2N(C3=C1SC=C3)N=NC=2S(=O)(=O)C1=CC(=CC=C1)Cl Chemical compound CNC1=NC=2N(C3=C1SC=C3)N=NC=2S(=O)(=O)C1=CC(=CC=C1)Cl VXVAEKFZSCCONZ-UHFFFAOYSA-N 0.000 claims 2
- QISPRJMRIXGXOP-UHFFFAOYSA-N N-benzyl-3-(3-chlorophenyl)sulfonyl-N-methyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N=1C2=C(S(=O)(=O)C=3C=C(Cl)C=CC=3)N=NN2C2=CC=CC=C2C=1N(C)CC1=CC=CC=C1 QISPRJMRIXGXOP-UHFFFAOYSA-N 0.000 claims 2
- FXQAJEAFVLGAEN-UHFFFAOYSA-N N-benzyl-3-(3-fluorophenyl)sulfonyl-N-methyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N=1C2=C(S(=O)(=O)C=3C=C(F)C=CC=3)N=NN2C2=CC=CC=C2C=1N(C)CC1=CC=CC=C1 FXQAJEAFVLGAEN-UHFFFAOYSA-N 0.000 claims 2
- IDNCPZCMEZTAIQ-UHFFFAOYSA-N N-benzyl-3-(4-fluorophenyl)sulfonyl-N-methyltriazolo[1,5-a]quinazolin-5-amine Chemical compound N=1C2=C(S(=O)(=O)C=3C=CC(F)=CC=3)N=NN2C2=CC=CC=C2C=1N(C)CC1=CC=CC=C1 IDNCPZCMEZTAIQ-UHFFFAOYSA-N 0.000 claims 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 2
- 150000001555 benzenes Chemical class 0.000 claims 2
- AMDWZBKKXZXSKL-UHFFFAOYSA-N ccg-165591 Chemical compound N1=NN2C=3C=CSC=3C(N(CC)CC)=NC2=C1S(=O)(=O)C1=CC=C(Cl)C=C1 AMDWZBKKXZXSKL-UHFFFAOYSA-N 0.000 claims 2
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- 125000004122 cyclic group Chemical group 0.000 claims 2
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- MHESYIOSEMELKG-UHFFFAOYSA-N hms1865n03 Chemical compound N1=NN2C=3C=CSC=3C(NCCCC)=NC2=C1S(=O)(=O)C1=CC=C(C)C(C)=C1 MHESYIOSEMELKG-UHFFFAOYSA-N 0.000 claims 2
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- QZTAWXTVENKNDC-UHFFFAOYSA-N molport-007-741-887 Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=C2N=C(NC3CCCC3)C(SC=C3)=C3N2N=N1 QZTAWXTVENKNDC-UHFFFAOYSA-N 0.000 claims 2
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- AFEOLFPUJYURJM-UHFFFAOYSA-N molport-020-178-648 Chemical compound N=1C2=C(S(=O)(=O)C=3C=C(Cl)C=CC=3)N=NN2C=2C=CSC=2C=1N(C)CC1=CC=CC=C1 AFEOLFPUJYURJM-UHFFFAOYSA-N 0.000 claims 2
- LSDZLXGUZQRKNI-UHFFFAOYSA-N molport-021-805-761 Chemical compound N1=NN2C=3C=CSC=3C(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 LSDZLXGUZQRKNI-UHFFFAOYSA-N 0.000 claims 2
- KVUMHGXKTMFHDX-UHFFFAOYSA-N molport-021-805-787 Chemical compound N1=NN2C=3C=CSC=3C=NC2=C1S(=O)(=O)C1=CC=CC=C1 KVUMHGXKTMFHDX-UHFFFAOYSA-N 0.000 claims 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- LQTUBUBKFMZWOF-UHFFFAOYSA-N C1=CC=C(C=C1)CCNC2=NC3=C(N=NN3C4=C2SC=C4)S(=O)(=O)C5=CC=C(C=C5)F Chemical compound C1=CC=C(C=C1)CCNC2=NC3=C(N=NN3C4=C2SC=C4)S(=O)(=O)C5=CC=C(C=C5)F LQTUBUBKFMZWOF-UHFFFAOYSA-N 0.000 claims 1
- ZIDKUHKPWGVNOR-UHFFFAOYSA-N CN(CC1=CC=CC=C1)C2=NC3=C(N=NN3C4=C2SC=C4)S(=O)(=O)C5=CC=CC(=C5)F Chemical compound CN(CC1=CC=CC=C1)C2=NC3=C(N=NN3C4=C2SC=C4)S(=O)(=O)C5=CC=CC(=C5)F ZIDKUHKPWGVNOR-UHFFFAOYSA-N 0.000 claims 1
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- 239000002552 dosage form Substances 0.000 claims 1
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- GCWNAFLHJNJVCV-UHFFFAOYSA-N molport-023-306-865 Chemical compound N=1C2=C(S(=O)(=O)C=3C=CC=CC=3)N=NN2C=2C=CSC=2C=1N(C)CC1=CC=CC=C1 GCWNAFLHJNJVCV-UHFFFAOYSA-N 0.000 claims 1
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- 108010006590 serotonin 5 receptor Proteins 0.000 abstract 2
- 208000024827 Alzheimer disease Diseases 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 150000003230 pyrimidines Chemical class 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical group BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- Bioinformatics & Cheminformatics (AREA)
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Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2008102155/04A RU2378278C2 (ru) | 2008-01-24 | 2008-01-24 | ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ |
| PCT/RU2009/000015 WO2009093934A2 (fr) | 2008-01-24 | 2009-01-23 | 3-sulphonyl-tiène[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines fonctionnant comme des antagonistes des récepteurs 5-ht6 de sérotonine, procédés de fabrication et d'utilisation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2008102155/04A RU2378278C2 (ru) | 2008-01-24 | 2008-01-24 | ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ |
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| Publication Number | Publication Date |
|---|---|
| RU2008102155A RU2008102155A (ru) | 2009-07-27 |
| RU2378278C2 true RU2378278C2 (ru) | 2010-01-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2008102155/04A RU2378278C2 (ru) | 2008-01-24 | 2008-01-24 | ЗАМЕЩЕННЫЕ 3-СУЛЬФОНИЛ-[1,2,3]ТРИАЗОЛО[1,5-a]ПИРИМИДИНЫ-АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЕ |
Country Status (2)
| Country | Link |
|---|---|
| RU (1) | RU2378278C2 (fr) |
| WO (1) | WO2009093934A2 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2303888B1 (fr) | 2008-06-12 | 2015-05-06 | President and Fellows of Harvard College | Composés pour intervention antimicrobienne |
| WO2013148813A1 (fr) * | 2012-03-27 | 2013-10-03 | The Regents Of The University Of California | Composés inhibiteurs triazolothiénopyrimidines de transporteurs d'urée et procédés d'utilisation des inhibiteurs |
| JP6515175B2 (ja) | 2014-07-08 | 2019-05-15 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | 芳香族ヘテロ環誘導体及びその医薬的適用 |
| WO2020109350A1 (fr) * | 2018-11-28 | 2020-06-04 | BioVersys AG | Dérivés de 3-(phénylsulfonyl)- [1,2,3]triazolo[1,5a]quinazolin-5(4h)-one |
| US11926628B2 (en) * | 2021-06-23 | 2024-03-12 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2065861C1 (ru) * | 1991-07-19 | 1996-08-27 | Дауэланко | N-пиразолил-1,2,4-триазоло-[1,5-с]-пиримидин-2-сульфонамидные соединения, способ их получения, гербицидная композиция и способ борьбы с нежелательной растительностью |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU208693B (en) * | 1991-02-22 | 1993-12-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing 1,2,4-triazolo (1,5-a) pyrimidinis derivatives and their carbicycli-tetrahydro-thiofurane-tetrahydrothiopyrane-, or tetrahydropyridine- condensated derivatives or medical preparatives containing them |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| GB0620787D0 (en) * | 2006-10-19 | 2006-11-29 | Inst Voor Landbouw En Visserij | Method and device for the selective isolation of serotypes |
-
2008
- 2008-01-24 RU RU2008102155/04A patent/RU2378278C2/ru not_active IP Right Cessation
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2009
- 2009-01-23 WO PCT/RU2009/000015 patent/WO2009093934A2/fr not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2065861C1 (ru) * | 1991-07-19 | 1996-08-27 | Дауэланко | N-пиразолил-1,2,4-триазоло-[1,5-с]-пиримидин-2-сульфонамидные соединения, способ их получения, гербицидная композиция и способ борьбы с нежелательной растительностью |
Non-Patent Citations (1)
| Title |
|---|
| KIM HYE JUNG et al., "New Serotonine 5-HT6 Ligands from Common Feature Pharmacophore Hypotheses" J. of Chemical Information and Modeling, 2008, 48(1), 197-206. * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009093934A3 (fr) | 2009-10-15 |
| RU2008102155A (ru) | 2009-07-27 |
| WO2009093934A2 (fr) | 2009-07-30 |
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