OA11165A - Process for preparation of pyrazoloÄ4,3-dÜpyeimidin-7-ones and intermediates thereof - Google Patents
Process for preparation of pyrazoloÄ4,3-dÜpyeimidin-7-ones and intermediates thereof Download PDFInfo
- Publication number
- OA11165A OA11165A OA9900224A OA9900224A OA11165A OA 11165 A OA11165 A OA 11165A OA 9900224 A OA9900224 A OA 9900224A OA 9900224 A OA9900224 A OA 9900224A OA 11165 A OA11165 A OA 11165A
- Authority
- OA
- OAPI
- Prior art keywords
- compound
- formula
- tertiary
- alkanol
- cycloalkyl
- Prior art date
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Classifications
-
- 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
-
- 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
- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (1)
- 011165 -27- CLAIMS 1) A process for the préparation of a compound of formulae (IA) and (IB)O2S. O2S. 'NNCHc (IA) 'N (IB) NCH2CH3 comprising reacting a compound of formula (IIA) and (IIB) respectively in thepresence of "OR, wherein R in the case of formation of compound (IA) is CH2CH3and R in the case of formation of compound (IB) is CH2CH2CH3, where X is aleaving group: -28- 0111652) A process as claimed in claim 1 wherein X is selected from the groupconsisting of arylsuiphonyloxy, C1-C4 alkylsulphonyloxy, nitro or halosubstituted benzenesulphonyloxy, C1-C4 perfluoroalkylsulphonyloxy,optionally substituted aroyloxy, C1-C4 perfluoroalkanoyloxy, C1-C4alkanoyloxy, halo; diazonium; C1-C4 primary and secondary alkoxy, oxonium,perchloryloxy, quatenaryammonium C1-C4 alkylsulphonuloxy,halosulphonyloxy, halonium and diarylsulphonylamino. 3) A process as claimed in claim 2 wherein X is a halo or methoxy. 4) A process as claimed in claim 3 wherein X is fluoro, chloro or methoxy. 5) A process as claimed in claim 4 wherein X is fluoro or chloro. 6) A process as claimed in any one of the preceeding daims wherein OR is présent with an auxiliary base. 7) A process as claimed in claim 6 wherein the auxiliary base is selected fromthe group consisting of sterically hindered base , métal salts of 1-methylpiperazine (especially for compound IA), 1-ethylpiperazine (especially forcompound IB), morpholine ,a métal hydride, métal oxide, métal carbonateand métal bicarbonate. 8) A process as claimed in claim 7 wherein the sterically hindered base is amétal sait of a sterically hindered alcohol or amine. 9) A process as claimed in claim 8 wherein the métal sait of a stericallyhindered alcohol or amine is selected from the group consisting of a 011165 -29- secondary or tertiary C4-C12 alkanol, a C3-C12 cycloalkanol and a secondary ortertiary (C3-C3 cycloalkyl)Ci-C6 alkanol, a N-(secondary or tertiary C3-C6 alkyl)-N-(primary, secondary or tertiary Ο3-Οθ alkyl)amine, a N-(C3-C8 cycloalkyl)-N-(primary, secondary or tertiary O3-C6 alkyl)amine, a di(C3-C8 cycloalkyl)amine 5 or hexamethyldisilazane 1,5-diazabicyclo[4,3,0]non-5-ene 1,8- diazabicyclo[5,4,0]undec-7-ene and tertiary amines such as triethylamine. 10) A process as claimed in daims 9 wherein the auxiliary base is a métal sait ofa tertiary alkanol. 11) A process as claimed in any one of the preceding daims wherein the réaction 10 is carried out in an inert solvent or ROH or a mixture of both. 12) A process as claimed in daim 11 wherein the solvent is selected from the group consisting of éthanol (for IA), n-propanol (for IB), a secondary ortertiary C4-C12 alkanol, a C3-Ci2 cycloalkanol, a tertiary C4-C12 cycloalkanol, asecondary or tertiary (C3-C7 cycloalkyl)C2-C6 alkanol, a C3-C9 alkanone, 1,2- 15 dimethoxyethane, 1,2-diethoxyethane, diglyme, tetrahydrofuran, 1,4-dioxan, toluene, xylene, chlorobenzene, 1,2-dichlorobenzene, acetonitrile, dimethylsulphoxide, sulpholane, dimethylformamide, N-methylpyrrolidin-2-one,pyridine, and mixtures thereof. 13) A process as claimed in daim 12 wherein the solvent is selected from the 20 group consisting of éthanol (for IA), n-propanol (for IB), a tertiary C4-Ci2 alkanol, a tertiary C4-Ci2 cycloalkanol, a tertiary (C3-C7 cycloalkyl)C2-C6alkanol, a C3-C9 alkanone, 1,2-dimethoxyethane, 1,2-diethoxyethane,diglyme, tetrahydrofuran, 1,4-dioxan, toluene, xylene, chlorobenzene, 1,2-dichlorobenzene, acetonitrile, sulpholane, dimethylformamide, N- 25 methylpyrrolidin-2-one, pyridine, and mixtures thereof. 14) A process as claimed in daim 13 wherein the solvent is éthanol (for IA) orpropanol (for IB). 15) A process for the préparation of a compound of formula (IA) and (IB)according to any one of the preceding daims comprising reacting a 30 compound of formula (IIA) and (IlB) respectively with ZOR , or with ROH and 011165 -30- an auxiliary base as defined hereinbefore or with ZOR and an auxiliary base,wherein ZOR is a sait of OR and Z is a cation. 16) A process as claimed in claim 15 wherein compound (IA) is formed byreaction of compound (IlA): 5 a) with éthanol and auxiliary base, optionally in an inert solvent; or b) with ZOEt and an auxiliary base in éthanol or an inert solvent or both; or) c) with ZOEt and éthanol or an inert solvent or both. 17) A process as claimed in claim 15 wherein compound (IB) is formed byreaction of compound (IIB): 10 d) with propanol and auxiliary base, optionally in an inert solvent (as defined herebefore); or e) with ZOPr and an auxiliary base, in propanol or an inert solvent or both; or f) with ZOPr, and propanol or an inert solvent or both. 18) A process as claimed in any one of the preceding daims wherein the 15 compound of formula (HA) is prepared by coupling a compound of formula (VI IA)-31- 011165 with a compound of formula (IXA)(IXA) and a compound of formula (IIB) is prepared by coupling a compound of formula(VIIB)(VIIB) with a compound of formula (IXB)-32- 011165 19) A process as claimed in claim 18 wherein a compound of the formula (VllA) isformed by coupling a compound of formula (VIA) with N-methylpiperazine(VIA) and a compound of formula (VHB) is formed by coupling a compound of formula(VIA) with N-ethylpiperazine. 20) A compound of formula(IIA) and (IIB):wherein X is as defined in any one of daims 1 to 5. 21) A compound of formula (IlIA) and (IIIB): -33- 011165(HIA)wherein X is as defined in anyone of daims 1 to 5. 22) A compound of formula (VIIA) and (VIIB)(VIIB) wherein X is as defined in anyone of daims 1 to 5. 23) A compound as claimed in any of daims 20 to 22 herein X is selected from thegroup consisting of fluoro, chloro and methoxy.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9822238.3A GB9822238D0 (en) | 1998-10-12 | 1998-10-12 | Process for preparation of pyrazolo[4,3-D]pyrimidin-7-ones and intermediates thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
OA11165A true OA11165A (en) | 2003-04-22 |
Family
ID=10840421
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
OA9900224A OA11165A (en) | 1998-10-12 | 1999-10-08 | Process for preparation of pyrazoloÄ4,3-dÜpyeimidin-7-ones and intermediates thereof |
Country Status (49)
Families Citing this family (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU5204800A (en) * | 1999-06-21 | 2001-01-09 | Biochemical Pharmaceutical Factory of Zhuhai Sez, The | Process for preparing sildenafil, and troche which comprises sildenafil and apomorphine |
AP2001002194A0 (en) * | 2000-06-22 | 2002-12-21 | Pfizer | Novel process for the preparation of pyrazolopyrimidinones. |
US6667398B2 (en) | 2000-06-22 | 2003-12-23 | Pfizer Inc | Process for the preparation of pyrazolopyrimidinones |
EP1176142A1 (fr) * | 2000-07-28 | 2002-01-30 | Pfizer Inc. | Procédé pour la préparation de pyrazoles |
EP1176147A1 (fr) * | 2000-07-28 | 2002-01-30 | Pfizer Limited | Procédé de préparation de pyrazolo[4,3-d]pyrimidin-7-ones et de leurs intermédiaires |
US6407259B1 (en) | 2000-07-28 | 2002-06-18 | Pfizer Inc. | Process for the preparation of pyrazoles |
PE20020394A1 (es) | 2000-08-18 | 2002-06-21 | Agouron Pharma | Compuestos de pirazol y composiciones farmaceuticas que los contienen, que modulan y/o inhiben la actividad de erab/hadh2 |
JP4554931B2 (ja) | 2001-12-20 | 2010-09-29 | メルク セローノ ソシエテ アノニム | プロスタグランジン調節物質としてのピロリジン誘導体 |
US6908923B2 (en) | 2001-12-21 | 2005-06-21 | Cytokinetics, Inc. | Compositions and methods for treating heart failure |
SI1509525T1 (sl) | 2002-05-31 | 2006-12-31 | Schering Corp | Postopek priprave inhibitorjev ksantinske fosfodiesteraze V in njihovih prekurzorjev |
WO2004072079A1 (fr) * | 2003-02-11 | 2004-08-26 | Pfizer Limited | Compose d'hemi-citrate de sildenafil hydrate et anhydre |
JP4969238B2 (ja) | 2003-03-27 | 2012-07-04 | サイトキネティクス・インコーポレーテッド | 化合物、組成物および方法 |
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 |
US20070010525A1 (en) * | 2005-06-27 | 2007-01-11 | Meyer Jackson | Method and compositions for modulating neuropeptide hormone secretion |
NL2000291C2 (nl) * | 2005-11-10 | 2009-02-17 | Pfizer Prod Inc | 1-(1-(2-ethoxyethyl)-3-ethyl-7-(4-methylpyridin-2-ylamino)-1H- pyrazool(4,3-d)pyrimidine-5-yl)piperidine-4-carbonzuur en zouten daarvan. |
EP2024369A4 (fr) * | 2006-06-05 | 2010-10-27 | Matrix Lab Ltd | Nouveau procédé de préparation du citrate de sildénafil |
CZ308056B6 (cs) * | 2015-07-20 | 2019-11-27 | Ustav Experimentalni Botaniky Av Cr V V I | 5-Substituované-7-[4-(substituované)benzyl]amino-3-isopropylpyrazolo[4,3-d]pyrimidiny, jejich použití jako antirevmatika, a farmaceutické přípravky |
WO2017168174A1 (fr) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | Nouvelles formes pharmaceutiques du sildénafil |
CN107759603B (zh) * | 2016-08-18 | 2020-09-01 | 四川科伦药物研究院有限公司 | 一种杂环化合物的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3992441A (en) * | 1972-12-26 | 1976-11-16 | Pfizer Inc. | Sulfamylbenzoic acids |
GB9013750D0 (en) * | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
GB9612514D0 (en) * | 1996-06-14 | 1996-08-14 | Pfizer Ltd | Novel process |
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 |
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1998
- 1998-10-12 GB GBGB9822238.3A patent/GB9822238D0/en not_active Ceased
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1999
- 1999-09-22 TW TW088116306A patent/TW589314B/zh not_active IP Right Cessation
- 1999-09-22 CU CU1999142A patent/CU22928A3/es unknown
- 1999-09-27 RS YUP-489/99A patent/RS49762B/sr unknown
- 1999-10-05 GT GT199900172A patent/GT199900172A/es unknown
- 1999-10-06 CZ CZ0353299A patent/CZ296816B6/cs not_active IP Right Cessation
- 1999-10-07 IL IL152928A patent/IL152928A/en not_active IP Right Cessation
- 1999-10-07 AP APAP/P/1999/001672A patent/AP1233A/en active
- 1999-10-07 CR CR6118A patent/CR6118A/es unknown
- 1999-10-07 IL IL15292399A patent/IL152923A/en not_active IP Right Cessation
- 1999-10-07 PE PE1999001016A patent/PE20001086A1/es not_active Application Discontinuation
- 1999-10-07 IL IL15292499A patent/IL152924A/en not_active IP Right Cessation
- 1999-10-07 IL IL15292799A patent/IL152927A/en not_active IP Right Cessation
- 1999-10-07 IL IL13227399A patent/IL132273A/en not_active IP Right Cessation
- 1999-10-07 IL IL15292699A patent/IL152926A/en not_active IP Right Cessation
- 1999-10-08 AR ARP990105109A patent/AR019244A1/es active IP Right Grant
- 1999-10-08 OA OA9900224A patent/OA11165A/en unknown
- 1999-10-08 CA CA002285733A patent/CA2285733C/fr not_active Expired - Lifetime
- 1999-10-08 SK SK1385-99A patent/SK285215B6/sk not_active IP Right Cessation
- 1999-10-08 UA UA99105491A patent/UA66787C2/xx unknown
- 1999-10-08 MY MYPI99004353A patent/MY124620A/en unknown
- 1999-10-08 IS IS5209A patent/IS1951B/is unknown
- 1999-10-08 US US09/415,440 patent/US6207829B1/en not_active Expired - Fee Related
- 1999-10-09 CN CNA031427383A patent/CN1473831A/zh active Pending
- 1999-10-09 CN CNB991239180A patent/CN1207295C/zh not_active Expired - Fee Related
- 1999-10-11 ES ES99307996T patent/ES2237049T3/es not_active Expired - Lifetime
- 1999-10-11 TN TNTNSN99189A patent/TNSN99189A1/fr unknown
- 1999-10-11 NO NO19994943A patent/NO313700B1/no not_active IP Right Cessation
- 1999-10-11 MA MA25812A patent/MA25007A1/fr unknown
- 1999-10-11 DE DE69923906T patent/DE69923906T2/de not_active Expired - Lifetime
- 1999-10-11 EG EG126999A patent/EG22630A/xx active
- 1999-10-11 BR BR9905092-7A patent/BR9905092A/pt not_active IP Right Cessation
- 1999-10-11 SI SI9930773T patent/SI0994115T1/xx unknown
- 1999-10-11 PT PT99307996T patent/PT994115E/pt unknown
- 1999-10-11 KR KR10-1999-0043836A patent/KR100380954B1/ko not_active IP Right Cessation
- 1999-10-11 HU HU9903469A patent/HU226162B1/hu not_active IP Right Cessation
- 1999-10-11 EA EA199900822A patent/EA003774B1/ru not_active IP Right Cessation
- 1999-10-11 ID IDP990941A patent/ID23351A/id unknown
- 1999-10-11 BG BG103794A patent/BG63205B1/bg unknown
- 1999-10-11 DZ DZ990212A patent/DZ2912A1/fr active
- 1999-10-11 DK DK99307996T patent/DK0994115T3/da active
- 1999-10-11 AT AT99307996T patent/ATE290003T1/de active
- 1999-10-11 ZA ZA9906412A patent/ZA996412B/xx unknown
- 1999-10-11 EP EP99307996A patent/EP0994115B1/fr not_active Expired - Lifetime
- 1999-10-11 AU AU53581/99A patent/AU756463B2/en not_active Ceased
- 1999-10-12 GE GEAP19995027A patent/GEP20022700B/en unknown
- 1999-10-12 EE EEP199900507A patent/EE04192B1/xx not_active IP Right Cessation
- 1999-10-12 SG SG1999005097A patent/SG118060A1/en unknown
- 1999-10-12 JP JP29009999A patent/JP3721021B2/ja not_active Expired - Fee Related
- 1999-10-12 TR TR1999/02541A patent/TR199902541A2/xx unknown
- 1999-10-12 CO CO99064776A patent/CO5150214A1/es unknown
- 1999-10-12 HR HR990318A patent/HRP990318B1/xx not_active IP Right Cessation
- 1999-10-12 UY UY25750A patent/UY25750A1/es not_active Application Discontinuation
- 1999-10-12 PL PL335959A patent/PL198150B1/pl not_active IP Right Cessation
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2000
- 2000-10-10 HK HK00106399A patent/HK1027559A1/xx not_active IP Right Cessation
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2001
- 2001-01-16 US US09/761,376 patent/US20010009962A1/en not_active Abandoned
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2002
- 2002-09-23 US US10/253,029 patent/US20030069422A1/en not_active Abandoned
- 2002-11-18 IL IL15292402A patent/IL152924A0/xx unknown
- 2002-11-18 IL IL15292302A patent/IL152923A0/xx unknown
- 2002-11-18 IL IL15292602A patent/IL152926A0/xx unknown
- 2002-11-18 IL IL15292702A patent/IL152927A0/xx unknown
- 2002-11-18 IL IL15292802A patent/IL152928A0/xx active IP Right Grant
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