UA78437C2 - Azabicyclic derivatives of pyridyloxymethyl and benzisoxazole - Google Patents

Info

Publication number

UA78437C2

UA78437C2 UAA200508639A UA2005008639A UA78437C2 UA 78437 C2 UA78437 C2 UA 78437C2 UA A200508639 A UAA200508639 A UA A200508639A UA 2005008639 A UA2005008639 A UA 2005008639A UA 78437 C2 UA78437 C2 UA 78437C2

Authority

UA

Ukraine

Prior art keywords

trans

isoxazol

pyridin

ylmethoxy

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 description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 243
• 238000000034 method Methods 0.000 claims abstract description 59
• 239000001257 hydrogen Substances 0.000 claims abstract description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 38
• 208000035475 disorder Diseases 0.000 claims abstract description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 36
• 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 29
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
• 150000002367 halogens Chemical group 0.000 claims abstract description 26
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 25
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
• 239000001301 oxygen Substances 0.000 claims abstract description 24
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 13
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
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• 239000012453 solvate Substances 0.000 claims abstract description 6
• 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
• 229940002612 prodrug Drugs 0.000 claims abstract description 5
• 239000000651 prodrug Substances 0.000 claims abstract description 5
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract description 4
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 5
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 174
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 120
• -1 hydroxy, amino Chemical group 0.000 claims description 90
• 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 87
• 125000000217 alkyl group Chemical group 0.000 claims description 65
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 59
• 150000001412 amines Chemical class 0.000 claims description 59
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 37
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 32
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• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 26
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
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• LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 18
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