TW200836727A - Substituted spirochromanone derivatives - Google Patents

Info

Publication number

TW200836727A

TW200836727A TW097100608A TW97100608A TW200836727A TW 200836727 A TW200836727 A TW 200836727A TW 097100608 A TW097100608 A TW 097100608A TW 97100608 A TW97100608 A TW 97100608A TW 200836727 A TW200836727 A TW 200836727A

Authority

TW

Taiwan

Prior art keywords

group

cyclopropyl

compound

oxo

methoxy

Prior art date

2007-01-12

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims abstract description 210
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 43
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 42
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
• 201000010099 disease Diseases 0.000 claims abstract description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 17
• 125000001424 substituent group Chemical group 0.000 claims abstract description 17
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 16
• 125000005843 halogen group Chemical group 0.000 claims abstract description 16
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
• 125000003118 aryl group Chemical group 0.000 claims abstract description 10
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 4
• -1 ^_C3-C6 alkyl group Chemical group 0.000 claims description 155
• 239000000203 mixture Substances 0.000 claims description 98
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• 238000011282 treatment Methods 0.000 claims description 61
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 54
• 150000002148 esters Chemical class 0.000 claims description 53
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• 239000003814 drug Substances 0.000 claims description 31
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 24
• 125000003003 spiro group Chemical group 0.000 claims description 24
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 22
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• SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 8
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• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
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• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
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• 229910052708 sodium Inorganic materials 0.000 claims description 2
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims 2
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• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
• 206010010904 Convulsion Diseases 0.000 claims 1
• 230000000996 additive effect Effects 0.000 claims 1
• 230000036461 convulsion Effects 0.000 claims 1
• 229910052736 halogen Inorganic materials 0.000 claims 1
• 150000002367 halogens Chemical class 0.000 claims 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 abstract description 24
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 3
• 230000001225 therapeutic effect Effects 0.000 abstract description 3
• KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 abstract description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract 2
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• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 139
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 100
• 235000019439 ethyl acetate Nutrition 0.000 description 68
• 239000003112 inhibitor Substances 0.000 description 61
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 52
• 239000000243 solution Substances 0.000 description 51
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 49
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