TW201141859A - Fused heterocyclic compounds as orexin receptor modulators - Google Patents

Info

Publication number

TW201141859A

TW201141859A TW099136021A TW99136021A TW201141859A TW 201141859 A TW201141859 A TW 201141859A TW 099136021 A TW099136021 A TW 099136021A TW 99136021 A TW99136021 A TW 99136021A TW 201141859 A TW201141859 A TW 201141859A

Authority

TW

Taiwan

Prior art keywords

phenyl

fluoro

triazol

dioxabicyclo

group

Prior art date

2009-10-23

Links

• Espacenet
• Global Dossier
• Discuss

• 108050000742 Orexin Receptor Proteins 0.000 title description 15
• 102000008834 Orexin receptor Human genes 0.000 title description 15
• 150000002391 heterocyclic compounds Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 336
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
• 238000011282 treatment Methods 0.000 claims abstract description 26
• 208000035475 disorder Diseases 0.000 claims abstract description 22
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• 206010022437 insomnia Diseases 0.000 claims abstract description 6
• -1 1H-pyrazol-1-yl Chemical group 0.000 claims description 210
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 196
• 239000000203 mixture Substances 0.000 claims description 126
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 78
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 68
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 32
• 238000002360 preparation method Methods 0.000 claims description 30
• 150000005829 chemical entities Chemical class 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 25
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• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 17
• 125000005843 halogen group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
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• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 12
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
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• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
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• RPZUBXWEQBPUJR-UHFFFAOYSA-N bicyclo[4.2.0]octane Chemical compound C1CCCC2CCC21 RPZUBXWEQBPUJR-UHFFFAOYSA-N 0.000 claims description 9
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• YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 8
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• 235000020824 obesity Nutrition 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 4
• SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical group C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims description 4
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• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 9
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