RU2477719C2 - Замещенные n-фенилбипирролидинкарбоксамиды и их терапевтическое применение - Google Patents

Info

Publication number

RU2477719C2

RU2477719C2 RU2010119560/04A RU2010119560A RU2477719C2 RU 2477719 C2 RU2477719 C2 RU 2477719C2 RU 2010119560/04 A RU2010119560/04 A RU 2010119560/04A RU 2010119560 A RU2010119560 A RU 2010119560A RU 2477719 C2 RU2477719 C2 RU 2477719C2

Authority

RU

Russia

Prior art keywords

methyl

bipyrrolidinyl

phenyl

carboxylic acid

combining

Prior art date

2007-10-17

Links

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• Global Dossier
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• 230000001225 therapeutic effect Effects 0.000 title description 2
• 150000003857 carboxamides Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 308
• 230000000694 effects Effects 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 239000003446 ligand Substances 0.000 claims abstract description 15
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• 208000020685 sleep-wake disease Diseases 0.000 claims abstract description 3
• -1 methanesulfonylmethyl Chemical group 0.000 claims description 162
• 150000003839 salts Chemical class 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 238000002360 preparation method Methods 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 13
• 230000027455 binding Effects 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 11
• UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
• 230000007958 sleep Effects 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
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• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 5
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
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• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
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• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical group 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
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• 239000000126 substance Substances 0.000 abstract description 11
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• 239000000543 intermediate Substances 0.000 description 73
• 239000000243 solution Substances 0.000 description 52
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• 238000004458 analytical method Methods 0.000 description 30
• 238000006243 chemical reaction Methods 0.000 description 30
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• 238000004809 thin layer chromatography Methods 0.000 description 27
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• 239000000203 mixture Substances 0.000 description 20
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• HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 18
• IGWCBBSIIURUEV-UHFFFAOYSA-N 4-[3-(2-methylpyrrolidin-1-yl)pyrrolidin-1-yl]-2-(trifluoromethyl)aniline Chemical compound CC1CCCN1C1CN(C=2C=C(C(N)=CC=2)C(F)(F)F)CC1 IGWCBBSIIURUEV-UHFFFAOYSA-N 0.000 description 17
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