EA023792B1 - ПРОИЗВОДНЫЕ (1,2,4)ТРИАЗОЛО[4,3-а]ХИНОКСАЛИНА В КАЧЕСТВЕ ИНГИБИТОРОВ ФОСФОДИЭСТЕРАЗ - Google Patents
ПРОИЗВОДНЫЕ (1,2,4)ТРИАЗОЛО[4,3-а]ХИНОКСАЛИНА В КАЧЕСТВЕ ИНГИБИТОРОВ ФОСФОДИЭСТЕРАЗ Download PDFInfo
- Publication number
- EA023792B1 EA023792B1 EA201300871A EA201300871A EA023792B1 EA 023792 B1 EA023792 B1 EA 023792B1 EA 201300871 A EA201300871 A EA 201300871A EA 201300871 A EA201300871 A EA 201300871A EA 023792 B1 EA023792 B1 EA 023792B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- triazolo
- methyl
- quinoxaline
- chloro
- phenyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 24
- 150000003252 quinoxalines Chemical class 0.000 title description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 89
- 238000011282 treatment Methods 0.000 claims abstract description 37
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 13
- PDOPFYRTIVSUKL-UHFFFAOYSA-N 4-(azepan-1-yl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1CCCCCN1C1=NC2=CC=CC=C2N2C1=NN=C2 PDOPFYRTIVSUKL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 157
- -1 pyran4-yl Chemical group 0.000 claims description 117
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 81
- 208000035475 disorder Diseases 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 28
- 208000024891 symptom Diseases 0.000 claims description 28
- 208000028698 Cognitive impairment Diseases 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 208000010877 cognitive disease Diseases 0.000 claims description 26
- 239000003814 drug Substances 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 230000003542 behavioural effect Effects 0.000 claims description 16
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 14
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 13
- 230000001771 impaired effect Effects 0.000 claims description 13
- 206010015037 epilepsy Diseases 0.000 claims description 12
- 230000013016 learning Effects 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 208000019022 Mood disease Diseases 0.000 claims description 10
- 206010012289 Dementia Diseases 0.000 claims description 9
- 238000011161 development Methods 0.000 claims description 9
- 208000013403 hyperactivity Diseases 0.000 claims description 9
- 208000020016 psychiatric disease Diseases 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000013256 coordination polymer Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 230000003340 mental effect Effects 0.000 claims description 8
- 208000011580 syndromic disease Diseases 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 7
- 208000016285 Movement disease Diseases 0.000 claims description 7
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000002858 neurotransmitter agent Substances 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 230000001667 episodic effect Effects 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- XRRVDIXCRUNODY-UHFFFAOYSA-N 1-(2-chlorophenyl)-7-methoxy-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C=1C(OC)=CC=C(N23)C=1N=C(C)C3=NN=C2C1=CC=CC=C1Cl XRRVDIXCRUNODY-UHFFFAOYSA-N 0.000 claims description 4
- DEATUVSNGIWELQ-UHFFFAOYSA-N 4-methyl-3-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)phenol Chemical compound CC1=CC=C(O)C=C1C1=NN=C2N1C1=CC=CC=C1N=C2C DEATUVSNGIWELQ-UHFFFAOYSA-N 0.000 claims description 4
- ZDOSWEGEZXKDLA-UHFFFAOYSA-N 8-chloro-1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(Cl)C=C3N2C=1C1=CC=CC=C1Cl ZDOSWEGEZXKDLA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000383 hazardous chemical Substances 0.000 claims description 4
- 231100000206 health hazard Toxicity 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- PJKIFMJYYIDRCR-UHFFFAOYSA-N 1-(2,6-difluorophenyl)-7-methoxy-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C=1C(OC)=CC=C(N23)C=1N=C(C)C3=NN=C2C1=C(F)C=CC=C1F PJKIFMJYYIDRCR-UHFFFAOYSA-N 0.000 claims description 3
- CIHGAHYOOKAOLL-UHFFFAOYSA-N 1-(2-chloro-6-fluorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=C(F)C=CC=C1Cl CIHGAHYOOKAOLL-UHFFFAOYSA-N 0.000 claims description 3
- CTBSIWZADWNGPL-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1Cl CTBSIWZADWNGPL-UHFFFAOYSA-N 0.000 claims description 3
- NTJSCTYPHZJWMH-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-methyl-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=CC=C1C1=NN=C2N1C1=CC(C(F)(F)F)=CC=C1N=C2C NTJSCTYPHZJWMH-UHFFFAOYSA-N 0.000 claims description 3
- DGTJUXLZPAKEDG-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=CC=C1C1=NN=C2N1C1=CC=CC=C1N=C2C DGTJUXLZPAKEDG-UHFFFAOYSA-N 0.000 claims description 3
- ZUKHTEAHHSGTQU-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CC1=CC=C(F)C=C1C1=NN=C2N1C1=CC=CC=C1N=C2C ZUKHTEAHHSGTQU-UHFFFAOYSA-N 0.000 claims description 3
- ISJMXGJOHQASQC-UHFFFAOYSA-N 1-[2-chloro-5-(4,4,4-trifluorobutoxy)phenyl]-4,8-dimethyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N12C3=CC(C)=CC=C3N=C(C)C2=NN=C1C1=CC(OCCCC(F)(F)F)=CC=C1Cl ISJMXGJOHQASQC-UHFFFAOYSA-N 0.000 claims description 3
- RBBMQJZCVDIUMH-UHFFFAOYSA-N 1-[2-chloro-5-(4,4,4-trifluorobutoxy)phenyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline-7-carbonitrile Chemical compound N=1N=C2C(C)=NC3=CC(C#N)=CC=C3N2C=1C1=CC(OCCCC(F)(F)F)=CC=C1Cl RBBMQJZCVDIUMH-UHFFFAOYSA-N 0.000 claims description 3
- FGNOPFLIGOJJBX-UHFFFAOYSA-N 1-[2-fluoro-5-(2-methoxyethoxy)phenyl]-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COCCOC1=CC=C(F)C(C=2N3C4=CC=CC=C4N=CC3=NN=2)=C1 FGNOPFLIGOJJBX-UHFFFAOYSA-N 0.000 claims description 3
- BCUVKJOAVZBEJO-UHFFFAOYSA-N 3-[4-chloro-3-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)phenoxy]propan-1-ol Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC(OCCCO)=CC=C1Cl BCUVKJOAVZBEJO-UHFFFAOYSA-N 0.000 claims description 3
- HXCMWAGIKQHTTN-UHFFFAOYSA-N 4-chloro-3-(8-chloro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)phenol Chemical compound N=1N=C2C(C)=NC3=CC=C(Cl)C=C3N2C=1C1=CC(O)=CC=C1Cl HXCMWAGIKQHTTN-UHFFFAOYSA-N 0.000 claims description 3
- KXSGJAHZGIIUIR-UHFFFAOYSA-N 4-methoxy-3-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)aniline Chemical compound COC1=CC=C(N)C=C1C1=NN=C2N1C1=CC=CC=C1N=C2C KXSGJAHZGIIUIR-UHFFFAOYSA-N 0.000 claims description 3
- QKWYLCALFFTEAL-UHFFFAOYSA-N 4-methyl-1-(2-nitrophenyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC=CC=C1[N+]([O-])=O QKWYLCALFFTEAL-UHFFFAOYSA-N 0.000 claims description 3
- WULGHPGREVSKPP-UHFFFAOYSA-N 4-methyl-3-(4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)aniline Chemical compound CC1=CC=C(N)C=C1C1=NN=C2N1C1=CC=CC=C1N=C2C WULGHPGREVSKPP-UHFFFAOYSA-N 0.000 claims description 3
- PQXINFPHBGOGGU-UHFFFAOYSA-N 8-bromo-1-(5-butoxy-2-fluorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(F)C(C=2N3C4=CC(Br)=CC=C4N=C(C)C3=NN=2)=C1 PQXINFPHBGOGGU-UHFFFAOYSA-N 0.000 claims description 3
- DQUUMQCEELFOJA-UHFFFAOYSA-N 8-chloro-1-(2-fluoro-5-hexoxyphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCCCOC1=CC=C(F)C(C=2N3C4=CC(Cl)=CC=C4N=C(C)C3=NN=2)=C1 DQUUMQCEELFOJA-UHFFFAOYSA-N 0.000 claims description 3
- BRYRUYOFUNGQDA-UHFFFAOYSA-N 8-chloro-1-(5-hexoxy-2-methylphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCCCOC1=CC=C(C)C(C=2N3C4=CC(Cl)=CC=C4N=C(C)C3=NN=2)=C1 BRYRUYOFUNGQDA-UHFFFAOYSA-N 0.000 claims description 3
- DWXIPQYAWWGYMW-UHFFFAOYSA-N 8-chloro-1-[2-chloro-5-(4,4,4-trifluorobutoxy)phenyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(Cl)C=C3N2C=1C1=CC(OCCCC(F)(F)F)=CC=C1Cl DWXIPQYAWWGYMW-UHFFFAOYSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 208000036626 Mental retardation Diseases 0.000 claims description 3
- 208000020114 Schizophrenia and other psychotic disease Diseases 0.000 claims description 3
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- 239000013543 active substance Substances 0.000 claims description 3
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- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 230000000926 neurological effect Effects 0.000 claims description 3
- 230000001314 paroxysmal effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 3
- JODONPFHDDVTRP-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=C(Cl)C(C=2N3C4=CC=CC=C4N=C(C)C3=NN=2)=C1 JODONPFHDDVTRP-UHFFFAOYSA-N 0.000 claims description 2
- DPCKYZFJQHZXHN-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)-8-fluoro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound COC1=CC=C(Cl)C(C=2N3C4=CC(F)=CC=C4N=C(C)C3=NN=2)=C1 DPCKYZFJQHZXHN-UHFFFAOYSA-N 0.000 claims description 2
- RZEFTNLVGHECCN-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-7-(quinolin-2-ylmethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC(OCC=4N=C5C=CC=CC5=CC=4)=CC=C3N2C=1C1=CC=CC=C1Cl RZEFTNLVGHECCN-UHFFFAOYSA-N 0.000 claims description 2
- DHCUFPIRHGVRLF-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-8-(quinolin-2-ylmethoxy)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(OCC=4N=C5C=CC=CC5=CC=4)C=C3N2C=1C1=CC=CC=C1Cl DHCUFPIRHGVRLF-UHFFFAOYSA-N 0.000 claims description 2
- QHAIBIZBWSNNOQ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-7-ol Chemical compound N=1N=C2C(C)=NC3=CC(O)=CC=C3N2C=1C1=CC=CC=C1Cl QHAIBIZBWSNNOQ-UHFFFAOYSA-N 0.000 claims description 2
- MXWNMGSRQFJJAP-UHFFFAOYSA-N 1-(2-chlorophenyl)-7-[2-(3,4-dimethoxyphenyl)ethoxy]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound C1=C(OC)C(OC)=CC=C1CCOC1=CC=C2N3C(C=4C(=CC=CC=4)Cl)=NN=C3C(C)=NC2=C1 MXWNMGSRQFJJAP-UHFFFAOYSA-N 0.000 claims description 2
- HRXOAOLOMPGQKA-UHFFFAOYSA-N 1-(2-fluoro-5-hexoxyphenyl)-4-methyl-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCCCOC1=CC=C(F)C(C=2N3C4=CC(=CC=C4N=C(C)C3=NN=2)C(F)(F)F)=C1 HRXOAOLOMPGQKA-UHFFFAOYSA-N 0.000 claims description 2
- ITEIGISUTJIFPA-UHFFFAOYSA-N 1-(5-butoxy-2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(Cl)C(C=2N3C4=CC=CC=C4N=C(C)C3=NN=2)=C1 ITEIGISUTJIFPA-UHFFFAOYSA-N 0.000 claims description 2
- ZMVRZQKLILPEKD-UHFFFAOYSA-N 1-(5-butoxy-2-chlorophenyl)-7-chloro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(Cl)C(C=2N3C4=CC=C(Cl)C=C4N=C(C)C3=NN=2)=C1 ZMVRZQKLILPEKD-UHFFFAOYSA-N 0.000 claims description 2
- IBWFVEHPUCUFLL-UHFFFAOYSA-N 1-(5-butoxy-2-chlorophenyl)-8-fluoro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(Cl)C(C=2N3C4=CC(F)=CC=C4N=C(C)C3=NN=2)=C1 IBWFVEHPUCUFLL-UHFFFAOYSA-N 0.000 claims description 2
- SOSIHXQIQCQQAY-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(F)C(C=2N3C4=CC=CC=C4N=C(C)C3=NN=2)=C1 SOSIHXQIQCQQAY-UHFFFAOYSA-N 0.000 claims description 2
- QBVZBJUFFOWWMK-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-7-chloro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(F)C(C=2N3C4=CC=C(Cl)C=C4N=C(C)C3=NN=2)=C1 QBVZBJUFFOWWMK-UHFFFAOYSA-N 0.000 claims description 2
- LHCPCLYKHMXEOC-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-8-chloro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(F)C(C=2N3C4=CC(Cl)=CC=C4N=C(C)C3=NN=2)=C1 LHCPCLYKHMXEOC-UHFFFAOYSA-N 0.000 claims description 2
- GDMYATOKVVQOBA-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-8-fluoro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(F)C(C=2N3C4=CC(F)=CC=C4N=C(C)C3=NN=2)=C1 GDMYATOKVVQOBA-UHFFFAOYSA-N 0.000 claims description 2
- LDNBSCAOQOOREI-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(F)C(C=2N3C4=CC=CC=C4N=CC3=NN=2)=C1 LDNBSCAOQOOREI-UHFFFAOYSA-N 0.000 claims description 2
- SWWRKKQBPXQMNE-UHFFFAOYSA-N 1-(5-butoxy-2-methylphenyl)-8-chloro-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CCCCOC1=CC=C(C)C(C=2N3C4=CC(Cl)=CC=C4N=C(C)C3=NN=2)=C1 SWWRKKQBPXQMNE-UHFFFAOYSA-N 0.000 claims description 2
- PHAZQDYQAKMELH-UHFFFAOYSA-N 1-(5-fluoro-2-methylphenyl)-4-methyl-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound CC1=CC=C(F)C=C1C1=NN=C2N1C1=CC(C(F)(F)F)=CC=C1N=C2C PHAZQDYQAKMELH-UHFFFAOYSA-N 0.000 claims description 2
- GJWZDGIFKCVONW-UHFFFAOYSA-N 1-[2-chloro-5-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C(C(=CC=1)Cl)=CC=1OCCN1CCCCC1 GJWZDGIFKCVONW-UHFFFAOYSA-N 0.000 claims description 2
- JSCMCHPQVQLFDT-UHFFFAOYSA-N 1-[2-chloro-5-(2-pyrrolidin-1-ylethoxy)phenyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C(C(=CC=1)Cl)=CC=1OCCN1CCCC1 JSCMCHPQVQLFDT-UHFFFAOYSA-N 0.000 claims description 2
- WEPVCXGLXHWLIC-UHFFFAOYSA-N 1-[2-chloro-5-(4,4,4-trifluorobutoxy)phenyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC(OCCCC(F)(F)F)=CC=C1Cl WEPVCXGLXHWLIC-UHFFFAOYSA-N 0.000 claims description 2
- RXAZDVFBDJEAKF-UHFFFAOYSA-N 1-[2-chloro-5-(4-fluorobutoxy)phenyl]-4-methyl-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=CC=C3N2C=1C1=CC(OCCCCF)=CC=C1Cl RXAZDVFBDJEAKF-UHFFFAOYSA-N 0.000 claims description 2
- QPOUOLVHXAVJFS-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]-4-methyl-8-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline Chemical compound N=1N=C2C(C)=NC3=CC=C(C(F)(F)F)C=C3N2C=1C1=CC(C(F)(F)F)=CC=C1Cl QPOUOLVHXAVJFS-UHFFFAOYSA-N 0.000 claims description 2
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- A—HUMAN NECESSITIES
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- 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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| JP6115962B2 (ja) * | 2011-06-27 | 2017-04-19 | ヤンセン ファーマシューティカ エヌ．ベー． | １−アリール−４−メチル−［１，２，４］トリアゾロ［４，３−ａ］キノキサリン誘導体 |
| WO2013034755A1 (en) * | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Triazolopyrazine derivatives and their use for treating neurological and psychiatric disorders |
| US9056863B2 (en) * | 2011-09-09 | 2015-06-16 | H. Lundbeck A/S | Substituted 2,3,5,9,9B-pentaazacyclopenta[a]naphthalenes and uses thereof |
| WO2013034758A1 (en) * | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Substituted triazolopyrazines and uses thereof |
| WO2014001314A1 (en) | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
| WO2014139983A1 (en) | 2013-03-13 | 2014-09-18 | H. Lundbeck A/S | [1,2,4]triazolo[4,3-a]quinoxalines as dual pde2/pde10 inhibitors |
| JP6696904B2 (ja) | 2014-01-08 | 2020-05-20 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 製剤および医薬組成物 |
| EP3134413B1 (en) | 2014-04-23 | 2019-09-11 | Dart NeuroScience (Cayman) Ltd. | Substituted [1,2,4]triazolo[1,5-a]pyrimidin-7-yl compounds as pde2 inhibitors |
| TWI568737B (zh) | 2014-11-05 | 2017-02-01 | 達特神經科學（開曼）有限責任公司 | 作為ｐｄｅ２抑制劑之經取代的５－甲基－［１，２，４］三唑并［１，５－ａ］嘧啶－２－胺化合物 |
| WO2016090382A1 (en) | 2014-12-06 | 2016-06-09 | Intra-Cellular Therapies, Inc. | Organic compounds |
| BR112017012007B1 (pt) | 2014-12-06 | 2022-11-01 | Intra-Cellular Therapies, Inc | Compostos orgânicos inibitórios de pde2, composições farmacêuticas compreendendo os ditos compostos e uso dos mesmos no tratamento de um distúrbio mediado por pde2 |
| EP3156405A1 (en) | 2015-10-13 | 2017-04-19 | Boehringer Ingelheim International GmbH | Spirocyclic ether derivatives of pyrazolo[1,5-a]pyrimidine-3-carboxamide |
| WO2017165311A1 (en) * | 2016-03-21 | 2017-09-28 | Perlstein Lab Pbc | Fused heterocyclic organic compounds and uses thereof |
| CN106212487B (zh) * | 2016-07-28 | 2018-11-13 | 浙江工业大学 | 一种含甲氧基苯并吡嗪结构的1,2,4-三唑衍生物作为杀菌剂的应用 |
| US11419874B2 (en) | 2017-11-23 | 2022-08-23 | Oslo University Hospital Hf | Treatment of tachycardia |
| CN116903569B (zh) * | 2023-07-06 | 2025-07-11 | 常州大学 | 作为磷酸二酯酶2抑制剂的香豆素-查尔酮杂合类衍生物及其应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008004117A1 (en) * | 2006-07-06 | 2008-01-10 | Pfizer Products Inc. | Selective azole pde10a inhibitor compounds |
| WO2009152825A1 (en) * | 2008-06-20 | 2009-12-23 | H. Lundbeck A/S | Novel phenylimidazole derivatives as pde10a enzyme inhibitors |
Family Cites Families (32)
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| US5153196A (en) | 1991-06-05 | 1992-10-06 | Eli Lilly And Company | Excitatory amino acid receptor antagonists and methods for the use thereof |
| US6235740B1 (en) * | 1997-08-25 | 2001-05-22 | Bristol-Myers Squibb Co. | Imidazoquinoxaline protein tyrosine kinase inhibitors |
| DE10108752A1 (de) | 2001-02-23 | 2002-09-05 | Bayer Ag | Neue Substituierte Imidazotriazinone |
| EP1613629A1 (en) * | 2003-03-27 | 2006-01-11 | Pfizer Products Inc. | Substituted 4-amino 1,2,4 triazolo 4,3-a quinoxalines |
| CA2523336A1 (en) * | 2003-04-30 | 2004-11-11 | Merck Frosst Canada Ltd. | 8-(3-biaryl)phenylquinoline phosphodiesterase-4-inhibitors |
| WO2005041957A1 (en) | 2003-10-29 | 2005-05-12 | Pfizer Products Inc. | Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors |
| CA2549510A1 (en) | 2003-12-16 | 2005-07-07 | Pfizer Products Inc. | Pyrido[2,3-d]pyrimidine-2,4-diamines as pde 2 inhibitors |
| EP1548011A1 (en) | 2003-12-23 | 2005-06-29 | Neuro3D | Benzo[1,4]diazepin-2-one derivatives as phosphodiesterase PDE2 inhibitors, preparation and therapeutic use thereof |
| FR2870539B1 (fr) | 2004-05-19 | 2006-08-04 | Greenpharma Sa Sa | Nouvelles methodes et medicaments |
| WO2006024640A2 (en) | 2004-09-02 | 2006-03-09 | Altana Pharma Ag | Triazolophthalazines |
| JP5130053B2 (ja) | 2005-01-05 | 2013-01-30 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | トリアゾロフタラジン |
| MX2007008137A (es) | 2005-01-05 | 2007-07-19 | Altana Pharma Ag | Triazoloftalazinas como inhibidores de pde2. |
| BRPI0502411A (pt) | 2005-03-31 | 2006-11-28 | Univ Minas Gerais | processo de desenvolvimento de substáncias como inibidores potentes e seletivos de isoformas de fosfodiesterases dos tipos 1 a 5 (pde1,pde2,pde3, pde4, pde5) na base de diocleìna, fluranol ou análogos e suas composições farmacêuticas para o estudo e tratamento de doenças cardiovasculares e produtos associados |
| CA2636043A1 (en) | 2006-01-23 | 2007-08-02 | Amira Pharmaceuticals, Inc. | Tricyclic inhibitors of 5-lipoxygenase |
| WO2007121319A2 (en) | 2006-04-14 | 2007-10-25 | University Of California | Compostions and methods for determining and predicting treatment responses for depression and anxiety |
| TW200815436A (en) | 2006-05-30 | 2008-04-01 | Elbion Ag | 4-amino-pyrido[3,2-e]pyrazines, their use as inhibitors of phosphodiesterase 10, and processes for preparing them |
| TW200817400A (en) | 2006-05-30 | 2008-04-16 | Elbion Ag | Pyrido [3,2-e] pyrazines, their use as inhibitors of phosphodiesterase 10, and processes for preparing them |
| DE102006048693A1 (de) | 2006-10-14 | 2008-04-17 | Bayer Healthcare Ag | Inhibition der PDE2A |
| WO2008072779A1 (ja) | 2006-12-13 | 2008-06-19 | Aska Pharmaceutical Co., Ltd. | キノキサリン誘導体 |
| EP2225248A1 (en) | 2007-11-30 | 2010-09-08 | Wyeth LLC | Aryl and heteroaryl fused imidazo[1,5-a]pyrazines as inhibitors of phosphodiesterase 10 |
| AU2008345225A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| JP2012502067A (ja) | 2008-09-10 | 2012-01-26 | カリプシス・インコーポレーテッド | 疾患の治療のためのヒスタミン受容体の複素環阻害剤 |
| WO2010054253A1 (en) | 2008-11-07 | 2010-05-14 | Biotie Therapies Gmbh | Triazine derivatives as inhibitors of phosphodiesterases |
| EP2406250B1 (en) | 2009-03-11 | 2015-08-12 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| TW201111383A (en) * | 2009-05-29 | 2011-04-01 | Wyeth Llc | Substituted imidazo[1,5-a]quinoxalines as inhibitors of phosphodiesterase 10 |
| EP2266985A1 (en) | 2009-06-26 | 2010-12-29 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | Tricyclic Pyrimidine Derivatives as Wnt antagonists |
| JP6106603B2 (ja) | 2011-01-11 | 2017-04-05 | スノビオン プハルマセウトイカルス インコーポレイテッド | ヘテロアリール化合物及びその使用方法 |
| JP6115962B2 (ja) | 2011-06-27 | 2017-04-19 | ヤンセン ファーマシューティカ エヌ．ベー． | １−アリール−４−メチル−［１，２，４］トリアゾロ［４，３−ａ］キノキサリン誘導体 |
| US9056863B2 (en) | 2011-09-09 | 2015-06-16 | H. Lundbeck A/S | Substituted 2,3,5,9,9B-pentaazacyclopenta[a]naphthalenes and uses thereof |
| WO2013034758A1 (en) | 2011-09-09 | 2013-03-14 | H. Lundbeck A/S | Substituted triazolopyrazines and uses thereof |
| WO2014001314A1 (en) | 2012-06-26 | 2014-01-03 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| US20140045856A1 (en) | 2012-07-31 | 2014-02-13 | Boehringer Ingelheim International Gmbh | 4-Methyl-2,3,5,9,9b-pentaaza-cyclopenta[a]naphthalenes |
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- 2012-01-31 KR KR1020137023101A patent/KR20140019342A/ko not_active Ceased
- 2012-01-31 AU AU2012213471A patent/AU2012213471B2/en not_active Ceased
- 2012-01-31 JP JP2013550908A patent/JP6027547B2/ja active Active
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- 2012-01-31 GE GEAP201213211A patent/GEP20156333B/en unknown
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- 2012-01-31 EA EA201300871A patent/EA023792B1/ru not_active IP Right Cessation
- 2012-01-31 TW TW101103150A patent/TWI535718B/zh not_active IP Right Cessation
- 2012-01-31 PE PE2013001585A patent/PE20141023A1/es not_active Application Discontinuation
- 2012-01-31 BR BR112013019354A patent/BR112013019354A2/pt not_active IP Right Cessation
- 2012-01-31 MA MA36142A patent/MA34844B1/fr unknown
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- 2013-07-29 TN TNP2013000325A patent/TN2013000325A1/fr unknown
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008004117A1 (en) * | 2006-07-06 | 2008-01-10 | Pfizer Products Inc. | Selective azole pde10a inhibitor compounds |
| WO2009152825A1 (en) * | 2008-06-20 | 2009-12-23 | H. Lundbeck A/S | Novel phenylimidazole derivatives as pde10a enzyme inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| KEHLER J. ET AL.: "Patented PDE10A inhibitors: Novel compounds since 2007", EXPERT OPINION ON THERAPEUTIC PATENTS, INFORMA HEALTHCARE, GB, vol. 19, no. 12, 1 December 2009 (2009-12-01), pages 1715-1725, XP002567797, ISSN: 1354-3776, DOI: 10.1517/13543770903431050, the whole document * |
Also Published As
| Publication number | Publication date |
|---|---|
| JP6027547B2 (ja) | 2016-11-16 |
| IL226826A (en) | 2016-10-31 |
| MX2013008667A (es) | 2013-10-01 |
| PE20141023A1 (es) | 2014-09-04 |
| JP2014503576A (ja) | 2014-02-13 |
| UA111963C2 (uk) | 2016-07-11 |
| ECSP13012824A (es) | 2013-10-31 |
| KR20140019342A (ko) | 2014-02-14 |
| TN2013000325A1 (en) | 2015-01-20 |
| AU2012213471A1 (en) | 2013-07-04 |
| MA34844B1 (fr) | 2014-01-02 |
| PH12013501355A1 (en) | 2013-09-02 |
| AU2012213471B2 (en) | 2016-07-14 |
| UY33888A (es) | 2012-08-31 |
| EA201300871A1 (ru) | 2014-01-30 |
| BR112013019354A2 (pt) | 2019-09-24 |
| US9540379B2 (en) | 2017-01-10 |
| EP2670754B1 (en) | 2017-05-24 |
| WO2012104293A1 (en) | 2012-08-09 |
| SG192210A1 (en) | 2013-09-30 |
| TWI535718B (zh) | 2016-06-01 |
| CL2013002003A1 (es) | 2013-12-06 |
| GEP20156333B (en) | 2015-07-27 |
| AR085099A1 (es) | 2013-09-11 |
| CA2824929A1 (en) | 2012-08-09 |
| CN103459395A (zh) | 2013-12-18 |
| EP2670754A1 (en) | 2013-12-11 |
| TW201245198A (en) | 2012-11-16 |
| NZ611630A (en) | 2015-03-27 |
| US20120302564A1 (en) | 2012-11-29 |
| CO6811848A2 (es) | 2013-12-16 |
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Designated state(s): AM AZ KG MD TJ TM |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): BY KZ RU |