JP2004505083A5 - - Google Patents
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- 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
- 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
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22245100P | 2000-08-02 | 2000-08-02 | |
| PCT/US2001/021678 WO2002010166A1 (en) | 2000-08-02 | 2001-07-09 | Fused heterocyclic derivatives as phosphodiesterase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004505083A JP2004505083A (ja) | 2004-02-19 |
| JP2004505083A5 true JP2004505083A5 (https=) | 2008-10-30 |
| JP4220775B2 JP4220775B2 (ja) | 2009-02-04 |
Family
ID=22832258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002515895A Expired - Fee Related JP4220775B2 (ja) | 2000-08-02 | 2001-07-09 | ホスホジエステラーゼ阻害剤としての融合複素環式誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7034027B2 (https=) |
| EP (1) | EP1305313A1 (https=) |
| JP (1) | JP4220775B2 (https=) |
| AU (1) | AU2001271948A1 (https=) |
| CA (1) | CA2423357C (https=) |
| MX (1) | MXPA03000887A (https=) |
| WO (1) | WO2002010166A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003303041B2 (en) | 2002-12-13 | 2008-07-24 | Warner-Lambert Company Llc | Alpha-2-delta ligand to treat lower urinary tract symptoms |
| BRPI0506994A (pt) | 2004-01-22 | 2007-07-03 | Pfizer | derivados de triazol que inibem a atividade antagonista da vasopressina |
| WO2007100387A2 (en) * | 2005-11-03 | 2007-09-07 | Dr. Reddy's Laboratories Ltd. | Process for preparing tadalafil |
| WO2010015585A1 (en) * | 2008-08-05 | 2010-02-11 | Nycomed Gmbh | 6-benzyl-2,3,4,7-tetrahydro-indolo[2,3-c]quinoline compounds |
| US20160317542A1 (en) | 2013-12-09 | 2016-11-03 | Respira Therapeutics, Inc. | Pde5 inhibitor powder formulations and methods relating thereto |
| AU2015399642B2 (en) | 2015-06-26 | 2020-04-09 | Chongqing Dikang Erle Pharma Co. Ltd. | Novel phosphodiesterase type-5 inhibitor and application thereof |
| WO2020033317A1 (en) * | 2018-08-07 | 2020-02-13 | Southern Research Institute | Piperazine-2,5-diones as tgf-beta inhibitors |
| CN113999228B (zh) * | 2021-11-08 | 2022-11-04 | 南京卓康医药科技有限公司 | 一种他达拉非的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9401090D0 (en) | 1994-01-21 | 1994-03-16 | Glaxo Lab Sa | Chemical compounds |
| GB9514465D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
| GB9514464D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Medicaments |
| US6046199A (en) * | 1998-01-14 | 2000-04-04 | Cell Pathways, Inc. | Method of inhibiting neoplastic cells with tetracyclic pyrido[3,4-B]indole derivatives |
| US6225315B1 (en) | 1998-11-30 | 2001-05-01 | Pfizer Inc | Method of treating nitrate-induced tolerance |
| US6613768B1 (en) * | 1999-04-30 | 2003-09-02 | Lilly Icos Llc | Treatment of female arousal disorder |
| ES2187234A1 (es) * | 1999-04-30 | 2003-05-16 | Lilly Icos Llc | Forma de dosificacion oral para tratar la disfuncion sexual. |
-
2001
- 2001-07-09 WO PCT/US2001/021678 patent/WO2002010166A1/en not_active Ceased
- 2001-07-09 MX MXPA03000887A patent/MXPA03000887A/es active IP Right Grant
- 2001-07-09 US US10/333,146 patent/US7034027B2/en not_active Expired - Fee Related
- 2001-07-09 AU AU2001271948A patent/AU2001271948A1/en not_active Abandoned
- 2001-07-09 JP JP2002515895A patent/JP4220775B2/ja not_active Expired - Fee Related
- 2001-07-09 CA CA002423357A patent/CA2423357C/en not_active Expired - Fee Related
- 2001-07-09 EP EP01951008A patent/EP1305313A1/en not_active Withdrawn
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