JP2004505083A5 - - Google Patents

Info

Publication number

JP2004505083A5

JP2004505083A5 JP2002515895A JP2002515895A JP2004505083A5 JP 2004505083 A5 JP2004505083 A5 JP 2004505083A5 JP 2002515895 A JP2002515895 A JP 2002515895A JP 2002515895 A JP2002515895 A JP 2002515895A JP 2004505083 A5 JP2004505083 A5 JP 2004505083A5

Authority

JP

Japan

Prior art keywords

pyrido

dioxol

benzo

indol

dioxo

Prior art date

2001-07-09

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Granted

Links

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• 238000000034 method Methods 0.000 description 10
• 241001465754 Metazoa Species 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• 150000001875 compounds Chemical class 0.000 description 6
• -1 acetic acid tert-butyl ester (3S, 6R, 12aR) -6-benzo [1,3] dioxol-5-yl-3-benzyloxymethyl-2,3,6,7,12,12a-hexahydropyrazino [1 ′, 2 ′ : 1,6] pyrido [3,4-b] indole-1,4-dione Chemical compound 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 4
• 239000008194 pharmaceutical composition Substances 0.000 description 4
• 238000011282 treatment Methods 0.000 description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
• 208000035475 disorder Diseases 0.000 description 3
• 150000003839 salts Chemical class 0.000 description 3
• 239000012453 solvate Substances 0.000 description 3
• 208000010228 Erectile Dysfunction Diseases 0.000 description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
• ZCZSIDMEHXZRLG-UHFFFAOYSA-N Heptyl acetate Chemical compound CCCCCCCOC(C)=O ZCZSIDMEHXZRLG-UHFFFAOYSA-N 0.000 description 2
• 230000037007 arousal Effects 0.000 description 2
• FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
• 201000001881 impotence Diseases 0.000 description 2
• 208000011580 syndromic disease Diseases 0.000 description 2
• CCZDDOBATQTYJA-RZQQEMMASA-N (3r,6r,12ar)-6-(1,3-benzodioxol-5-yl)-3-(chloromethyl)-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@@H]3C(=O)N[C@H](C(N32)=O)CCl)=C1 CCZDDOBATQTYJA-RZQQEMMASA-N 0.000 description 1
• YIBYDZHWHLMWIA-YCRNBWNJSA-N (3s,6r,12ar)-3-(4-aminobutyl)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@@H]3C(=O)N[C@H](C(N32)=O)CCCCN)=C1 YIBYDZHWHLMWIA-YCRNBWNJSA-N 0.000 description 1
• SLJGZKQKVLMVET-RZQQEMMASA-N (3s,6r,12ar)-3-(aminomethyl)-6-(1,3-benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C(C4=CC=CC=C4N3)C[C@@H]3C(=O)N[C@H](C(N32)=O)CN)=C1 SLJGZKQKVLMVET-RZQQEMMASA-N 0.000 description 1
• HJSJFGAIJXJZEY-BPYKYCOYSA-N (3s,6r,12ar)-6-(1,3-benzodioxol-5-yl)-3-(3-pyridylmethyl)-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound C([C@@H]1NC([C@@H]2N([C@@H](C3=C(C4=CC=CC=C4N3)C2)C=2C=C3OCOC3=CC=2)C1=O)=O)C1=CC=CN=C1 HJSJFGAIJXJZEY-BPYKYCOYSA-N 0.000 description 1
• UXZFYTTUQMRDCH-LZCXECNNSA-N (3s,6r,12ar)-6-(1,3-benzodioxol-5-yl)-3-[2-keto-2-(4-methylpiperazino)ethyl]-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound C1CN(C)CCN1C(=O)C[C@H]1C(=O)N2[C@H](C=3C=C4OCOC4=CC=3)C(NC=3C4=CC=CC=3)=C4C[C@@H]2C(=O)N1 UXZFYTTUQMRDCH-LZCXECNNSA-N 0.000 description 1
• ZDSNTZVDVXETRU-DLCOBIQGSA-N (6r,12ar)-6-(1,3-benzodioxol-5-yl)-3-(pyrazol-1-ylmethyl)-2,3,6,7,12,12a-hexahydropyrazino[1,2-b]$b-carboline-1,4-quinone Chemical compound O=C([C@@H]1N([C@@H](C2=C(C3=CC=CC=C3N2)C1)C=1C=C2OCOC2=CC=1)C1=O)NC1CN1C=CC=N1 ZDSNTZVDVXETRU-DLCOBIQGSA-N 0.000 description 1
• YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
• ZOWSJJBOQDKOHI-UHFFFAOYSA-N 2,2,2-trifluoroethyl acetate Chemical compound CC(=O)OCC(F)(F)F ZOWSJJBOQDKOHI-UHFFFAOYSA-N 0.000 description 1
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
• WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 description 1
• 208000009304 Acute Kidney Injury Diseases 0.000 description 1
• 206010002383 Angina Pectoris Diseases 0.000 description 1
• 206010002388 Angina unstable Diseases 0.000 description 1
• 206010059245 Angiopathy Diseases 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
• 206010007559 Cardiac failure congestive Diseases 0.000 description 1
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
• 206010013975 Dyspnoeas Diseases 0.000 description 1
• 208000010412 Glaucoma Diseases 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 206010022998 Irritability Diseases 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 208000031481 Pathologic Constriction Diseases 0.000 description 1
• 208000018262 Peripheral vascular disease Diseases 0.000 description 1
• 208000005107 Premature Birth Diseases 0.000 description 1
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
• 208000033626 Renal failure acute Diseases 0.000 description 1
• 206010039085 Rhinitis allergic Diseases 0.000 description 1
• 208000007718 Stable Angina Diseases 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• 208000005485 Thrombocytosis Diseases 0.000 description 1
• 208000007814 Unstable Angina Diseases 0.000 description 1
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
• 208000012871 acute dyspnea Diseases 0.000 description 1
• 201000011040 acute kidney failure Diseases 0.000 description 1
• 208000012998 acute renal failure Diseases 0.000 description 1
• 201000009961 allergic asthma Diseases 0.000 description 1
• 201000010105 allergic rhinitis Diseases 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• 238000007889 carotid angioplasty Methods 0.000 description 1
• 208000023819 chronic asthma Diseases 0.000 description 1
• 208000020832 chronic kidney disease Diseases 0.000 description 1
• 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
• 238000007887 coronary angioplasty Methods 0.000 description 1
• 238000009109 curative therapy Methods 0.000 description 1
• YFPCLQKFNXUAAK-UHFFFAOYSA-N cyclopentyl acetate Chemical compound CC(=O)OC1CCCC1 YFPCLQKFNXUAAK-UHFFFAOYSA-N 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 208000000718 duodenal ulcer Diseases 0.000 description 1
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
• 208000027866 inflammatory disease Diseases 0.000 description 1
• 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
• 230000008991 intestinal motility Effects 0.000 description 1
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropyl acetate Chemical compound CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
• 201000005857 malignant hypertension Diseases 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• 208000028591 pheochromocytoma Diseases 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 201000004240 prostatic hypertrophy Diseases 0.000 description 1
• 208000002815 pulmonary hypertension Diseases 0.000 description 1
• 208000037804 stenosis Diseases 0.000 description 1
• 230000036262 stenosis Effects 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
• 230000002792 vascular Effects 0.000 description 1
• 208000019553 vascular disease Diseases 0.000 description 1