SK283896B6 - Kyselina 2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl) benzoová - Google Patents
Kyselina 2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl) benzoová Download PDFInfo
- Publication number
- SK283896B6 SK283896B6 SK1786-2001A SK17862001A SK283896B6 SK 283896 B6 SK283896 B6 SK 283896B6 SK 17862001 A SK17862001 A SK 17862001A SK 283896 B6 SK283896 B6 SK 283896B6
- Authority
- SK
- Slovakia
- Prior art keywords
- compound
- formula
- mol
- sildenafil
- acid
- Prior art date
Links
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 title abstract description 21
- 229960003310 sildenafil Drugs 0.000 title abstract description 10
- 238000004519 manufacturing process Methods 0.000 title 1
- TXKSEEXWAGLOIY-UHFFFAOYSA-N 2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylbenzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC=C1S(=O)(=O)N1CCN(C)CC1 TXKSEEXWAGLOIY-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 abstract description 49
- 238000000034 method Methods 0.000 abstract description 18
- 238000002360 preparation method Methods 0.000 abstract description 10
- 230000007935 neutral effect Effects 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000013074 reference sample Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- MZRUFMBFIKGOAL-UHFFFAOYSA-N 5-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C1=CC=NN1 MZRUFMBFIKGOAL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000005957 chlorosulfonylation reaction Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005694 sulfonylation reaction Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical group OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MDKAAWDKKBFSTK-UHFFFAOYSA-N 2-ethoxybenzoyl chloride Chemical compound CCOC1=CC=CC=C1C(Cl)=O MDKAAWDKKBFSTK-UHFFFAOYSA-N 0.000 description 1
- IFFGTBBYPRZJLD-UHFFFAOYSA-N 4-[[2-ethoxy-5-(4-methylpiperazin-1-yl)sulfonylbenzoyl]amino]-2-methyl-5-propylpyrazole-3-carboxamide Chemical compound CCCC1=NN(C)C(C(N)=O)=C1NC(=O)C1=CC(S(=O)(=O)N2CCN(C)CC2)=CC=C1OCC IFFGTBBYPRZJLD-UHFFFAOYSA-N 0.000 description 1
- UHNRCKXZRULNSC-UHFFFAOYSA-N 5-chlorosulfonyl-2-ethoxybenzoic acid Chemical compound CCOC1=CC=C(S(Cl)(=O)=O)C=C1C(O)=O UHNRCKXZRULNSC-UHFFFAOYSA-N 0.000 description 1
- 208000010228 Erectile Dysfunction Diseases 0.000 description 1
- -1 alkyl 2-ethoxybenzoate Chemical compound 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940051879 analgesics and antipyretics salicylic acid and derivative Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- QAYQKAPOTVSWLS-UHFFFAOYSA-N methyl 2-ethoxybenzoate Chemical compound CCOC1=CC=CC=C1C(=O)OC QAYQKAPOTVSWLS-UHFFFAOYSA-N 0.000 description 1
- WEMPSVOPLDKKRH-UHFFFAOYSA-N methyl 5-chlorosulfonyl-2-ethoxybenzoate Chemical compound CCOC1=CC=C(S(Cl)(=O)=O)C=C1C(=O)OC WEMPSVOPLDKKRH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Urology & Nephrology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9612514.1A GB9612514D0 (en) | 1996-06-14 | 1996-06-14 | Novel process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK283896B6 true SK283896B6 (sk) | 2004-04-06 |
Family
ID=10795332
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1783-2001A SK283894B6 (sk) | 1996-06-14 | 1997-06-10 | Spôsob výroby 5-[2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl)- fenyl]-1-metyl-3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d]pyrimidin-7-ónu |
| SK1787-2001A SK283897B6 (sk) | 1996-06-14 | 1997-06-10 | 4-[2-Etoxy-5-(4-metylpiperazin-1-ylsulfonyl)benzamido]-1-metyl-3- n-propylpyrazol-5-karboxamid |
| SK743-97A SK283893B6 (sk) | 1996-06-14 | 1997-06-10 | Spôsob výroby 5-[2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl)- fenyl]-1-metyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]- pyrimidin-7-ónu a medziprodukty tohto spôsobu |
| SK1784-2001A SK283895B6 (sk) | 1996-06-14 | 1997-06-10 | Spôsob výroby 5[2-etoxy-5-(4-metylpiperazinu-1-ylsulfonyl)- fenyl]-1-metyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-ónu |
| SK1786-2001A SK283896B6 (sk) | 1996-06-14 | 1997-06-10 | Kyselina 2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl) benzoová |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1783-2001A SK283894B6 (sk) | 1996-06-14 | 1997-06-10 | Spôsob výroby 5-[2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl)- fenyl]-1-metyl-3-n-propyl-1,6-dihydro-7H-pyrazolo [4,3-d]pyrimidin-7-ónu |
| SK1787-2001A SK283897B6 (sk) | 1996-06-14 | 1997-06-10 | 4-[2-Etoxy-5-(4-metylpiperazin-1-ylsulfonyl)benzamido]-1-metyl-3- n-propylpyrazol-5-karboxamid |
| SK743-97A SK283893B6 (sk) | 1996-06-14 | 1997-06-10 | Spôsob výroby 5-[2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl)- fenyl]-1-metyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]- pyrimidin-7-ónu a medziprodukty tohto spôsobu |
| SK1784-2001A SK283895B6 (sk) | 1996-06-14 | 1997-06-10 | Spôsob výroby 5[2-etoxy-5-(4-metylpiperazinu-1-ylsulfonyl)- fenyl]-1-metyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-ónu |
Country Status (47)
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060222647A1 (en) * | 1993-05-27 | 2006-10-05 | Beavo Joseph A | Methods and compositions for modulating the activity of PDE5 |
| US6723719B1 (en) * | 1997-04-25 | 2004-04-20 | Pfizer Inc | Pyrazolopyrimidinones which inhibit type 5 cyclic guanosine 3′,5′—monophosphate phosphodiesterase (cGMP PDE5) for the treatment of sexual dysfunction |
| WO1998053819A1 (fr) * | 1997-05-29 | 1998-12-03 | Mochida Pharmaceutical Co., Ltd. | Agent therapeutique destine a traiter l'anerection |
| US6399618B1 (en) | 1997-07-09 | 2002-06-04 | Cardiome Pharma Corp | Compositions and methods for modulating sexual activity |
| GB9722520D0 (en) | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| SI1049695T1 (en) | 1997-11-12 | 2002-06-30 | Bayer Aktiengesellschaft | 2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors |
| HRP20000712A2 (en) | 1998-04-20 | 2001-06-30 | Pfizer | PYRAZOLOPYRIMIDINONE cGMP PDE5 INHIBITORS FOR THE TREATMENT OF SEXUAL DYSFUNCTION |
| CA2235642C (en) | 1998-05-15 | 2007-11-13 | Torcan Chemical Ltd. | Processes for preparing sildenafil |
| EP1109814B1 (en) * | 1998-09-04 | 2004-04-21 | Ortho-McNeil Pharmaceutical, Inc. | 5-heterocyclyl pyrazolo 4,3-d]pyrimidin-7-ones for the treatment of male erectile dysfunction |
| GB9822238D0 (en) * | 1998-10-12 | 1998-12-09 | Pfizer Ltd | Process for preparation of pyrazolo[4,3-D]pyrimidin-7-ones and intermediates thereof |
| GB9823101D0 (en) | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| GB9823103D0 (en) | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| GB9823102D0 (en) | 1998-10-23 | 1998-12-16 | Pfizer Ltd | Pharmaceutically active compounds |
| KR100353014B1 (ko) * | 1998-11-11 | 2002-09-18 | 동아제약 주식회사 | 발기부전 치료에 효과를 갖는 피라졸로피리미디논 화합물 |
| US6087362A (en) * | 1999-03-16 | 2000-07-11 | Pentech Pharmaceuticals, Inc. | Apomorphine and sildenafil composition |
| CN1094492C (zh) * | 1999-06-21 | 2002-11-20 | 杭州神鹰医药化工有限公司 | 西地那非的制备方法 |
| WO2000078760A1 (fr) * | 1999-06-21 | 2000-12-28 | The Biochemical Pharmaceutical Factory Of Zhuhai Sez | Procede de preparation de sildenafil, agent et procede d'obtention d'un comprime mixte a base de sildenafil et de chlorhydrate d'apomorphine |
| CN1077108C (zh) * | 1999-07-13 | 2002-01-02 | 成都地奥制药集团有限公司 | 用于制备药物昔多芬的前体化合物 |
| AU1888800A (en) * | 1999-09-13 | 2001-04-17 | Cipla Limited | A novel process for the synthesis of sildenafil citrate |
| US6075028A (en) * | 1999-09-23 | 2000-06-13 | Graham; Richard | Method of treating Tourette's syndrome and related CNS disorders |
| TWI265925B (en) * | 1999-10-11 | 2006-11-11 | Pfizer | Pyrazolo[4,3-d]pyrimidin-7-ones useful in inhibiting type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterases(cGMP PDE5), process and intermediates for their preparation, their uses and composition comprising them |
| EP1222190A1 (en) | 1999-10-11 | 2002-07-17 | Pfizer Limited | 5-(2-substituted-5-heterocyclylsulphonylpyrid-3-yl)-dihydropyrazolo[4,3-d]pyrimidin-7-ones as phosphodiesterase inhibitors |
| US6667398B2 (en) | 2000-06-22 | 2003-12-23 | Pfizer Inc | Process for the preparation of pyrazolopyrimidinones |
| GB0015462D0 (en) * | 2000-06-22 | 2000-08-16 | Pfizer Ltd | Novel process for the preparation of pyrazolopyrimidinones |
| US6730786B2 (en) | 2000-06-22 | 2004-05-04 | Pfizer Inc | Process for the preparation of pyrazolopyrimidinones |
| WO2001098303A1 (en) * | 2000-06-22 | 2001-12-27 | Pfizer Limited | Novel process for the preparation of pyrazolopyrimidinones |
| US6407259B1 (en) | 2000-07-28 | 2002-06-18 | Pfizer Inc. | Process for the preparation of pyrazoles |
| EP1176142A1 (en) * | 2000-07-28 | 2002-01-30 | Pfizer Inc. | Process for the preparation of pyrazoles |
| YU51701A (sh) * | 2000-07-28 | 2003-12-31 | Pfizer Inc. | Postupak za dobijanje jedinjenja pirazola/4,3-d/ pirimidin-7-ona i njihovih derivata |
| US6821978B2 (en) | 2000-09-19 | 2004-11-23 | Schering Corporation | Xanthine phosphodiesterase V inhibitors |
| CN1127506C (zh) * | 2001-06-29 | 2003-11-12 | 刘宝顺 | 一种治疗阳痿的新化合物 |
| EP1421084B1 (en) * | 2001-08-28 | 2008-05-14 | Schering Corporation | Polycyclic guanine phosphodiesterase v inhibitors |
| EP1719772A1 (en) | 2002-05-31 | 2006-11-08 | Schering Corporation | Process for preparing xanthine phosphodiesterase v inhibitors and precursors thereof |
| DE10232113A1 (de) | 2002-07-16 | 2004-01-29 | Bayer Ag | Vardenafil Hydrochlorid Trihydrat enthaltende Arzneimittel |
| CN100374441C (zh) | 2003-06-06 | 2008-03-12 | 天津倍方科技发展有限公司 | 二氢吡咯[2，3-d]嘧啶-4-酮衍生物，其制备方法及其制药用途 |
| CN100360531C (zh) * | 2003-12-18 | 2008-01-09 | 中国人民解放军军事医学科学院放射与辐射医学研究所 | 用于预防或治疗阳萎和性冷淡的新吡唑并嘧啶类化合物 |
| ES2300979T3 (es) | 2004-01-05 | 2008-06-16 | Teva Pharmaceutical Industries Ltd. | Procedimiento para la produccion de sildenafilo base y de su sal citrato. |
| EP1779852A3 (en) * | 2004-01-05 | 2007-05-09 | Teva Pharmaceutical Industries Ltd. | Processes for the production of sildenafil base and citrate salt |
| DE102005009240A1 (de) | 2005-03-01 | 2006-09-07 | Bayer Healthcare Ag | Arzneiformen mit verbesserten pharmakokinetischen Eigenschaften |
| CN101563348B (zh) * | 2006-12-21 | 2011-08-24 | 上海特化医药科技有限公司 | 西地那非的制备方法及其中间体 |
| ES2310144B1 (es) | 2007-06-15 | 2010-01-12 | Galenicum Health, S.L. | Intermedios para la preparacion de un inhibidor de la fosfodiesterasa tipo 5. |
| WO2010067140A1 (es) | 2008-12-12 | 2010-06-17 | Siegfried Rhein S.A. De C.V. | Composicion de liberacion pulsatil de sildenafil y proceso para prepararla |
| MX2010006227A (es) | 2010-06-07 | 2011-12-14 | World Trade Imp Exp Wtie Ag | Nuevos derivados 1,4-diazepanos, inhibidores de pde-5. |
| CN102993205B (zh) * | 2012-12-27 | 2015-04-15 | 华润赛科药业有限责任公司 | 一种高收率制备高纯度西地那非游离碱的纯化方法 |
| CN103044330B (zh) * | 2013-01-14 | 2018-11-13 | 常州亚邦制药有限公司 | 西地那非中间体4-氨基-1-甲基-3-正丙基吡唑-5-甲酰胺的绿色合成新工艺 |
| CN105085526B (zh) * | 2014-05-15 | 2017-08-01 | 重庆圣华曦药业股份有限公司 | 一种改进的西地那非制备方法 |
| CN105753870B (zh) * | 2016-04-01 | 2018-05-22 | 重庆康刻尔制药有限公司 | 一种西地那非杂质f及其制备方法和应用 |
| WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
| CN105837578A (zh) * | 2016-04-05 | 2016-08-10 | 重庆康刻尔制药有限公司 | 一种西地那非杂质d的合成方法 |
| EP3522920A2 (en) | 2016-10-10 | 2019-08-14 | Transgene SA | Immunotherapeutic product and mdsc modulator combination therapy |
| CN113493459B (zh) * | 2020-04-07 | 2022-12-13 | 广州白云山医药集团股份有限公司白云山制药总厂 | Pde5抑制剂化合物及其制备方法和应用 |
| CN112961160A (zh) * | 2021-03-05 | 2021-06-15 | 遂成药业股份有限公司 | 一种西地那非的改良合成工艺 |
| CN113754612B (zh) * | 2021-10-26 | 2023-09-26 | 山东安舜制药有限公司 | 一种西地那非中间体的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282361A (en) | 1978-03-16 | 1981-08-04 | Massachusetts Institute Of Technology | Synthesis for 7-alkylamino-3-methylpyrazolo [4,3-d]pyrimidines |
| US4871843A (en) * | 1983-10-18 | 1989-10-03 | Dropic-Societe Civile De Gestion De Droits De Propriete Industrielle | Cyclic benzenesulfonamides, process for their preparation and their use as active substance of pharmaceutical compositions |
| GB9013750D0 (en) * | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
| GB9114760D0 (en) * | 1991-07-09 | 1991-08-28 | Pfizer Ltd | Therapeutic agents |
| GB9311920D0 (en) * | 1993-06-09 | 1993-07-28 | Pfizer Ltd | Therapeutic agents |
| US6723719B1 (en) * | 1997-04-25 | 2004-04-20 | Pfizer Inc | Pyrazolopyrimidinones which inhibit type 5 cyclic guanosine 3′,5′—monophosphate phosphodiesterase (cGMP PDE5) for the treatment of sexual dysfunction |
| US6087368A (en) * | 1998-06-08 | 2000-07-11 | Bristol-Myers Squibb Company | Quinazolinone inhibitors of cGMP phosphodiesterase |
-
1996
- 1996-06-14 GB GBGB9612514.1A patent/GB9612514D0/en active Pending
-
1997
- 1997-05-14 HN HN1997000072A patent/HN1997000072A/es unknown
- 1997-05-30 NO NO972481A patent/NO304551B1/no not_active IP Right Cessation
- 1997-06-02 AP APAP/P/1997/001009A patent/AP717A/en active
- 1997-06-04 SI SI9730005T patent/SI0812845T1/xx not_active IP Right Cessation
- 1997-06-04 DK DK98123740T patent/DK0916675T3/da active
- 1997-06-04 ES ES97303832T patent/ES2134051T3/es not_active Expired - Lifetime
- 1997-06-04 DE DE69723846T patent/DE69723846T2/de not_active Expired - Lifetime
- 1997-06-04 EP EP97303832A patent/EP0812845B1/en not_active Expired - Lifetime
- 1997-06-04 DK DK97303832T patent/DK0812845T3/da active
- 1997-06-04 ES ES98123740T patent/ES2201397T3/es not_active Expired - Lifetime
- 1997-06-04 SI SI9730577T patent/SI0916675T1/xx unknown
- 1997-06-04 EP EP98123740A patent/EP0916675B1/en not_active Expired - Lifetime
- 1997-06-04 AT AT98123740T patent/ATE246194T1/de active
- 1997-06-04 AT AT97303832T patent/ATE182150T1/de active
- 1997-06-04 PT PT98123740T patent/PT916675E/pt unknown
- 1997-06-04 DE DE69700321T patent/DE69700321T2/de not_active Expired - Lifetime
- 1997-06-05 IL IL12100097A patent/IL121000A/xx not_active IP Right Cessation
- 1997-06-05 IL IL12541197A patent/IL125411A/xx not_active IP Right Cessation
- 1997-06-05 TR TR97/00470A patent/TR199700470A2/xx unknown
- 1997-06-05 BG BG101569A patent/BG62554B1/bg unknown
- 1997-06-06 US US08/869,532 patent/US5955611A/en not_active Expired - Lifetime
- 1997-06-10 SK SK1783-2001A patent/SK283894B6/sk not_active IP Right Cessation
- 1997-06-10 SK SK1787-2001A patent/SK283897B6/sk not_active IP Right Cessation
- 1997-06-10 IS IS4503A patent/IS1922B/is unknown
- 1997-06-10 SK SK743-97A patent/SK283893B6/sk not_active IP Right Cessation
- 1997-06-10 SK SK1784-2001A patent/SK283895B6/sk not_active IP Right Cessation
- 1997-06-10 SK SK1786-2001A patent/SK283896B6/sk not_active IP Right Cessation
- 1997-06-10 IN IN1548DE1997 patent/IN187350B/en unknown
- 1997-06-10 SA SA97180124A patent/SA97180124B1/ar unknown
- 1997-06-11 TN TNTNSN97102A patent/TNSN97102A1/fr unknown
- 1997-06-11 PE PE2001000983A patent/PE20011303A1/es not_active IP Right Cessation
- 1997-06-11 PE PE1997000483A patent/PE1299A1/es not_active IP Right Cessation
- 1997-06-11 DZ DZ970097A patent/DZ2247A1/fr active
- 1997-06-11 EA EA199700061A patent/EA000102B1/ru not_active IP Right Cessation
- 1997-06-11 MA MA24655A patent/MA24205A1/fr unknown
- 1997-06-12 CA CA002207694A patent/CA2207694C/en not_active Expired - Lifetime
- 1997-06-12 CZ CZ19971811A patent/CZ290942B6/cs not_active IP Right Cessation
- 1997-06-12 UA UA97062802A patent/UA27085C2/uk unknown
- 1997-06-12 AR ARP970102564A patent/AR003401A1/es unknown
- 1997-06-12 EG EG54097A patent/EG24123A/xx active
- 1997-06-12 ID IDP972004A patent/ID18745A/id unknown
- 1997-06-12 SG SG1997002037A patent/SG50024A1/en unknown
- 1997-06-13 KR KR1019970024457A patent/KR100207352B1/ko not_active Expired - Fee Related
- 1997-06-13 RS YUP-254/97A patent/RS49653B/sr unknown
- 1997-06-13 MX MX9704433A patent/MX9704433A/es unknown
- 1997-06-13 RS YUP-2006/0484A patent/RS49924B/sr unknown
- 1997-06-13 HU HU9701048A patent/HU224497B1/hu not_active IP Right Cessation
- 1997-06-13 AU AU24878/97A patent/AU697684B2/en not_active Ceased
- 1997-06-13 NZ NZ328084A patent/NZ328084A/en not_active IP Right Cessation
- 1997-06-13 UY UY24585A patent/UY24585A1/es not_active IP Right Cessation
- 1997-06-13 OA OA70024A patent/OA10426A/en unknown
- 1997-06-13 CO CO97032741A patent/CO4780028A1/es unknown
- 1997-06-13 JP JP9156422A patent/JP2866841B2/ja not_active Expired - Lifetime
- 1997-06-13 CN CN97113261A patent/CN1106399C/zh not_active Expired - Lifetime
- 1997-06-13 PL PL97320555A patent/PL189333B1/pl not_active IP Right Cessation
- 1997-06-13 ZA ZA9705259A patent/ZA975259B/xx unknown
- 1997-06-13 HR HR970326A patent/HRP970326B1/xx not_active IP Right Cessation
- 1997-06-16 BR BR9703580A patent/BR9703580A/pt not_active IP Right Cessation
- 1997-07-09 UY UY24612A patent/UY24612A1/es not_active IP Right Cessation
-
1998
- 1998-07-20 IL IL12541198A patent/IL125411A0/xx unknown
- 1998-09-25 JP JP10271067A patent/JP3058863B2/ja not_active Expired - Lifetime
- 1998-10-30 NO NO985064A patent/NO306115B1/no not_active IP Right Cessation
-
1999
- 1999-07-23 US US09/360,128 patent/US6066735A/en not_active Expired - Lifetime
- 1999-08-26 GR GR990402170T patent/GR3031087T3/el unknown
-
2000
- 2000-07-05 CN CNB001200542A patent/CN1149206C/zh not_active Expired - Lifetime
-
2001
- 2001-04-24 IN IN520DE2001 patent/IN187320B/en unknown
- 2001-04-24 IN IN519DE2001 patent/IN187319B/en unknown
- 2001-04-24 IN IN518DE2001 patent/IN187318B/en unknown
- 2001-04-24 IN IN517DE2001 patent/IN187317B/en unknown
-
2002
- 2002-11-25 IS IS6634A patent/IS1923B/is unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SK283896B6 (sk) | Kyselina 2-etoxy-5-(4-metylpiperazin-1-ylsulfonyl) benzoová | |
| JP4018182B2 (ja) | ジハロアゾロピリミジン類の製造方法 | |
| US6046337A (en) | Process for the preparation of a dihydropyridine derivative | |
| KR20190034582A (ko) | 스피로케탈-치환된 사이클릭 케토에놀의 제조 방법 | |
| EP0452143B1 (en) | Process for preparing optically active 3-hydroxypyrrolidine derivatives | |
| PL174526B1 (pl) | Nowe związki pochodne karbazolonu | |
| US4841068A (en) | 3-hydroxy pyrazole derivatives | |
| US5155257A (en) | Process for the preparation of acylaminomethanephosphonic acids | |
| KR0141482B1 (ko) | 0-카르복시피리딜-및 0-카르복시퀴놀릴이미다졸리논의 개선된 제조방법 | |
| US5650514A (en) | 3-substituted quinoline-5-carboxylic acid derivatives and processes for their preparation | |
| KR870000823B1 (ko) | 5,6,7,7a-테트라하이드로-4H-티에노(3,2-c)-피리딘-2-온 유도체의 제조방법 | |
| HU195773B (en) | Process for preparing alkyl esters of 4-alkoxy-3-pyrrolin-2-on-1-yl-acetic acid | |
| AU647562B2 (en) | Process and intermediate for certain bis-aza-bicyclic anxiolytic agents | |
| US4927970A (en) | Substituted 3-cyclobutene-1,2-dione intermediates | |
| RU2032679C1 (ru) | Производные бензатиазинов | |
| US5731433A (en) | Process for the preparation of rufloxacin and salts thereof | |
| US4835288A (en) | Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-a]pyrrole-1,7-dicarboxylates | |
| KR100699457B1 (ko) | 디벤조티에핀 유도체 및 그 중간체의 제조방법 | |
| JPH0717598B2 (ja) | ３―フェニルピロール誘導体の製造方法 | |
| KR950013852B1 (ko) | 4-에톡시카보닐-1-메틸-5-피라졸머캅탄의 제조방법 | |
| US4937368A (en) | Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-A]pyrrole-1,7-dicarboxylates | |
| US5476940A (en) | 3-substituted quinoline-5-carboxylic acids | |
| US5106978A (en) | Process and intermediates for the preparation of spiro(isoquinoline-4(1H), 3'-pyrrolidine)-1,2', 3,5'(2H)-tetrones which are useful as aldose reductase inhibitors | |
| CZ282094A3 (en) | Process for preparing substituted quinazoline-2,4-diones | |
| US4874872A (en) | Process for preparing (+)-2,3-dihydro-1H-pyrrolo[1,2-A]pyrrole-1,7-dicarboxylates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC4A | Assignment and transfer of rights |
Owner name: PFIZER IRELAND PHARMACEUTICALS, RINGASKIDDY, C, IE Free format text: FORMER OWNER: PFIZER IRELAND PHARMACEUTICALS, DUN LAOGHAIRE, COUNTY DUBLIN, IE Effective date: 20110131 |
|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20130610 |