EA023792B1 - ПРОИЗВОДНЫЕ (1,2,4)ТРИАЗОЛО[4,3-а]ХИНОКСАЛИНА В КАЧЕСТВЕ ИНГИБИТОРОВ ФОСФОДИЭСТЕРАЗ - Google Patents

Info

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

2011-01-31

Links

• Espacenet
• Global Dossier
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• 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
• 208000027520 Somatoform disease Diseases 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 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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