EA009527B1 - Пиридилоксиметильные и бензизоксазольные азабициклические производные - Google Patents

Info

Publication number

EA009527B1

EA009527B1 EA200501148A EA200501148A EA009527B1 EA 009527 B1 EA009527 B1 EA 009527B1 EA 200501148 A EA200501148 A EA 200501148A EA 200501148 A EA200501148 A EA 200501148A EA 009527 B1 EA009527 B1 EA 009527B1

Authority

EA

Eurasian Patent Office

Prior art keywords

isoxazol

trans

benzo

pyrazin

ylmethyl

Prior art date

2003-03-12

Links

• Espacenet
• Global Dossier
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• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 267
• 238000000034 method Methods 0.000 claims abstract description 57
• 150000003839 salts Chemical class 0.000 claims abstract description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
• 239000001257 hydrogen Substances 0.000 claims abstract description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 24
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
• 150000002367 halogens Chemical class 0.000 claims abstract description 22
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 21
• 239000001301 oxygen Substances 0.000 claims abstract description 21
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims abstract description 17
• 150000002431 hydrogen Chemical class 0.000 claims abstract description 15
• 239000012453 solvate Substances 0.000 claims abstract description 15
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 11
• DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims abstract description 9
• -1 cyano, amino Chemical group 0.000 claims description 208
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 58
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 57
• 150000001412 amines Chemical class 0.000 claims description 43
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
• 239000002253 acid Substances 0.000 claims description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 29
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 26
• GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 12
• ONHPOXROAPYCGT-UHFFFAOYSA-N 2,3,4,6,7,8,9,9a-octahydro-1h-pyrido[1,2-a]pyrazine Chemical compound C1CNCC2CCCCN21 ONHPOXROAPYCGT-UHFFFAOYSA-N 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• NMMIHXMBOZYNET-UHFFFAOYSA-N Methyl picolinate Chemical compound COC(=O)C1=CC=CC=N1 NMMIHXMBOZYNET-UHFFFAOYSA-N 0.000 claims description 11
• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 229910052717 sulfur Chemical group 0.000 claims description 9
• 239000011593 sulfur Chemical group 0.000 claims description 9
• 241000124008 Mammalia Species 0.000 claims description 8
• XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 8
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
• 210000003169 central nervous system Anatomy 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• PJMUNJOFKTZCIW-UHFFFAOYSA-N 3-[7-[[5-(pyrrolidin-1-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC2=NC=C(C=C2)CN2CCCC2 PJMUNJOFKTZCIW-UHFFFAOYSA-N 0.000 claims description 6
• IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 claims description 6
• GYQGTXCPMYFRLU-UHFFFAOYSA-N 3-(2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl)-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CCCC2 GYQGTXCPMYFRLU-UHFFFAOYSA-N 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
• IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims description 4
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 4
• YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 claims description 4
• HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
• GXAUMTXKKVKIJZ-UHFFFAOYSA-N 3-[7-[[5-(piperidin-1-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1h-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound C1CC2C(C3=NOC=C3)NCCN2CC1COC(N=C1)=CC=C1CN1CCCCC1 GXAUMTXKKVKIJZ-UHFFFAOYSA-N 0.000 claims description 3
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
• YYWGUWVWUGWQPY-UHFFFAOYSA-N 3-[7-[[5-[(2-methylpyrrolidin-1-yl)methyl]pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC=C(C=C1)CN1C(CCC1)C YYWGUWVWUGWQPY-UHFFFAOYSA-N 0.000 claims description 2
• GFNMLOFOXILWJE-UHFFFAOYSA-N 3-[7-[[6-(pyrrolidin-1-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC(=CC=C1)CN1CCCC1 GFNMLOFOXILWJE-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• YDOQLJXCEUEJNJ-UHFFFAOYSA-N 3-[7-[[5-(1,3-thiazolidin-3-ylmethyl)pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC1=NC=C(C=C1)CN1CSCC1 YDOQLJXCEUEJNJ-UHFFFAOYSA-N 0.000 claims 1
• FVCBUSCIOBOAAE-UHFFFAOYSA-N 3-[7-[[5-[(4-methyl-1,4-diazepan-1-yl)methyl]pyridin-2-yl]oxymethyl]-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-1-yl]-1,2-oxazole Chemical compound O1N=C(C=C1)C1C2N(CCN1)CC(CC2)COC2=NC=C(C=C2)CN2CCN(CCC2)C FVCBUSCIOBOAAE-UHFFFAOYSA-N 0.000 claims 1
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
• YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
• 125000000217 alkyl group Chemical group 0.000 abstract description 43
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 12
• 208000015114 central nervous system disease Diseases 0.000 abstract description 11
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 9
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• 238000001819 mass spectrum Methods 0.000 description 158
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• 238000004458 analytical method Methods 0.000 description 107
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 82
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• 239000002904 solvent Substances 0.000 description 68
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