TWI433845B - 嗒酮衍生物 - Google Patents

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Publication number

TWI433845B

TWI433845B TW097149958A TW97149958A TWI433845B TW I433845 B TWI433845 B TW I433845B TW 097149958 A TW097149958 A TW 097149958A TW 97149958 A TW97149958 A TW 97149958A TW I433845 B TWI433845 B TW I433845B

Authority

TW

Taiwan

Prior art keywords

group

formula

compound

het

mmol

Prior art date

2007-12-21

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• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title 1
• -1 iso Oxazolyl Chemical group 0.000 claims description 144
• 150000001875 compounds Chemical class 0.000 claims description 124
• 239000000203 mixture Substances 0.000 claims description 73
• 150000003839 salts Chemical class 0.000 claims description 61
• 238000000034 method Methods 0.000 claims description 49
• 238000011282 treatment Methods 0.000 claims description 30
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 20
• 239000002904 solvent Substances 0.000 claims description 19
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 238000002360 preparation method Methods 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 16
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000002971 oxazolyl group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000000217 alkyl group Chemical group 0.000 claims description 9
• 229910052801 chlorine Inorganic materials 0.000 claims description 9
• 125000002541 furyl group Chemical group 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
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• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 125000001425 triazolyl group Chemical group 0.000 claims description 9
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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• 125000003277 amino group Chemical group 0.000 claims description 6
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
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• 235000011152 sodium sulphate Nutrition 0.000 description 14
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• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
• 125000004430 oxygen atom Chemical group O* 0.000 description 13
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
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