HRP20050798A2 - Pyridyloxymethyl and benzisoxazole azabicyclic derivatives - Google Patents

Info

Publication number

HRP20050798A2

HRP20050798A2 HR20050798A HRP20050798A HRP20050798A2 HR P20050798 A2 HRP20050798 A2 HR P20050798A2 HR 20050798 A HR20050798 A HR 20050798A HR P20050798 A HRP20050798 A HR P20050798A HR P20050798 A2 HRP20050798 A2 HR P20050798A2

Authority

HR

Croatia

Prior art keywords

isoxazol

trans

pyrazin

ylmethyl

benzo

Prior art date

2003-03-12

Links

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• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 237
• -1 Aminomethylpyridyloxymethyl Chemical group 0.000 claims abstract description 78
• 238000000034 method Methods 0.000 claims abstract description 57
• 239000001257 hydrogen Substances 0.000 claims abstract description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 35
• 208000035475 disorder Diseases 0.000 claims abstract description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 23
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
• 239000001301 oxygen Substances 0.000 claims abstract description 23
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 22
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 21
• 150000002367 halogens Chemical class 0.000 claims abstract description 21
• 208000020401 Depressive disease Diseases 0.000 claims abstract description 14
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 14
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
• 239000011593 sulfur Substances 0.000 claims abstract description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
• 239000012453 solvate Substances 0.000 claims abstract description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 5
• 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 5
• 239000000651 prodrug Substances 0.000 claims abstract description 5
• 229940002612 prodrug Drugs 0.000 claims abstract description 5
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 58
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 53
• 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 46
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 39
• 102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 claims description 30
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 25
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• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 22
• 150000001412 amines Chemical class 0.000 claims description 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
• 206010012289 Dementia Diseases 0.000 claims description 20
• 239000003112 inhibitor Substances 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
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• 101150049660 DRD2 gene Proteins 0.000 claims description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 16
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• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 125000002950 monocyclic group Chemical group 0.000 claims description 12
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 11
• 241000124008 Mammalia Species 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 10
• XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 10
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• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 10
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• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
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• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 6
• 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 6
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• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 6
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• GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 4
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• UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 claims description 4
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• YNBADRVTZLEFNH-UHFFFAOYSA-N methyl nicotinate Chemical compound COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 claims description 4
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• AMNSTJVLSCINFN-JCUDRXCFSA-N 3-[(7R,9aS)-7-[[6-[[(2S,5S)-2,5-dimethylpyrrolidin-1-yl]methyl]pyridin-2-yl]oxymethyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-5-fluoro-1,2-benzoxazole Chemical compound C[C@@H]1N([C@H](CC1)C)CC1=CC=CC(=N1)OC[C@@H]1CC[C@@H]2N(CCN(C2)C2=NOC3=C2C=C(C=C3)F)C1 AMNSTJVLSCINFN-JCUDRXCFSA-N 0.000 claims description 3
• KETKNCJQPBIFRE-FUCAVZNHSA-N 3-[(7R,9aS)-7-[[6-[[(2S,6S)-2,6-dimethylpiperidin-1-yl]methyl]pyridin-2-yl]oxymethyl]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]-5-fluoro-1,2-benzoxazole Chemical compound C[C@@H]1N([C@H](CCC1)C)CC1=CC=CC(=N1)OC[C@@H]1CC[C@@H]2N(CCN(C2)C2=NOC3=C2C=C(C=C3)F)C1 KETKNCJQPBIFRE-FUCAVZNHSA-N 0.000 claims description 3
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