MA33764B1 - Procédé de fabrication du {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate de méthyle et de purification de celui-ci en vue de son utilisation comme principe actif pharmaceutique - Google Patents

Procédé de fabrication du {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate de méthyle et de purification de celui-ci en vue de son utilisation comme principe actif pharmaceutique

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Publication number
MA33764B1
MA33764B1 MA34893A MA34893A MA33764B1 MA 33764 B1 MA33764 B1 MA 33764B1 MA 34893 A MA34893 A MA 34893A MA 34893 A MA34893 A MA 34893A MA 33764 B1 MA33764 B1 MA 33764B1
Authority
MA
Morocco
Prior art keywords
fluorobenzyl
purification
berzolo
berdine
pyridimine
Prior art date
Application number
MA34893A
Other languages
Arabic (ar)
English (en)
Inventor
Franz-Josef Mais
Joachim Rehse
Winfried Joentgen
Konrad Siegel
Original Assignee
Bayer Ip Gmbh
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer Ip Gmbh filed Critical Bayer Ip Gmbh
Publication of MA33764B1 publication Critical patent/MA33764B1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond

Abstract

)la présente invention concerne un procédé de fabrication du {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate de méthyle, à savoir du composé de formule (i), ainsi qu'un procédé de purification du produit brut de formule (i) pour l'utilisation comme principe pharmaceutiquement actif, à l'occasion de quoi pour la purification du {4,6-diamino-2-[1-(2-fluorobenzyl)- 1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate de méthyle-sulfinyldiméthane (1 :2) de formule (ii) est isolé comme stade intermédiaire ou est produit, le cas échéant présent dans un mélange, comme stade intermédiaire dans ce procédé de purification.
MA34893A 2009-11-27 2012-05-25 Procédé de fabrication du {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate de méthyle et de purification de celui-ci en vue de son utilisation comme principe actif pharmaceutique MA33764B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09177369 2009-11-27
PCT/EP2010/067884 WO2011064156A2 (fr) 2009-11-27 2010-11-22 Procédé de fabrication du {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate de méthyle et de purification de celui-ci en vue de son utilisation comme principe actif pharmaceutique

Publications (1)

Publication Number Publication Date
MA33764B1 true MA33764B1 (fr) 2012-11-01

Family

ID=43568194

Family Applications (1)

Application Number Title Priority Date Filing Date
MA34893A MA33764B1 (fr) 2009-11-27 2012-05-25 Procédé de fabrication du {4,6-diamino-2-[1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate de méthyle et de purification de celui-ci en vue de son utilisation comme principe actif pharmaceutique

Country Status (22)

Country Link
US (1) US8501945B2 (fr)
EP (1) EP2504335B1 (fr)
JP (1) JP2013512211A (fr)
KR (1) KR20120098815A (fr)
CN (1) CN102712637A (fr)
AR (1) AR079135A1 (fr)
AU (1) AU2010323297A1 (fr)
BR (1) BR112012012618A2 (fr)
CA (1) CA2781922A1 (fr)
CO (1) CO6551707A2 (fr)
CU (1) CU20120083A7 (fr)
DO (1) DOP2012000143A (fr)
EA (1) EA201270639A1 (fr)
EC (1) ECSP12011920A (fr)
ES (1) ES2433236T3 (fr)
IL (1) IL219861A0 (fr)
MA (1) MA33764B1 (fr)
MX (1) MX2012005942A (fr)
TN (1) TN2012000259A1 (fr)
TW (1) TW201200513A (fr)
UY (1) UY33041A (fr)
WO (1) WO2011064156A2 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RS59908B1 (sr) 2009-11-27 2020-03-31 Adverio Pharma Gmbh Postupak za proizvodnju metil-{4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridin-3-il]pirimidin-5-il}metilkarbamata
DE102010021637A1 (de) 2010-05-26 2011-12-01 Bayer Schering Pharma Aktiengesellschaft Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung
DE102010043379A1 (de) 2010-11-04 2012-05-10 Bayer Schering Pharma Aktiengesellschaft Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung
DE102010043380A1 (de) 2010-11-04 2012-05-10 Bayer Schering Pharma Aktiengesellschaft Benzyl-substituierte Carbamate und ihre Verwendung
JP6189315B2 (ja) 2011-11-25 2017-08-30 アドヴェリオ・ファーマ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング 置換された５−フルオロ−１ｈ−ピラゾロピリジン類を製造するための方法
BR112015019571A2 (pt) * 2013-02-21 2017-07-18 Adverio Pharma Gmbh formas de {4,6-diamino-2-[1-(2-fluorobenzil)-1h-pirazolo[3,4-b]piridino-3-il]pirimidino-5-il}metilcarbamato de metila
CN108463224A (zh) 2015-12-14 2018-08-28 铁木医药有限公司 sGC刺激剂用于胃肠功能障碍治疗的应用
CN108069960A (zh) * 2016-11-15 2018-05-25 江苏豪森药业集团有限公司 利奥西呱中间体的制备方法
US20190381039A1 (en) 2016-12-13 2019-12-19 Cyclerion Therapeutics, Inc. USE OF sGC STIMULATORS FOR THE TREATMENT OF ESOPHAGEAL MOTILITY DISORDERS
JP2021530491A (ja) 2018-07-11 2021-11-11 サイクレリオン・セラピューティクス，インコーポレーテッド ミトコンドリア（ｍｉｔｏｃｈｏｎｒｉａｌ）障害の処置のためのｓＧＣ刺激剤の使用
EP3925953A1 (fr) * 2020-06-16 2021-12-22 Adverio Pharma GmbH Procédé de préparation de méthyl {4,6-diamino-2-[5-fluoro-1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-yl]pyrimidin-5-yl}carbamate

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9013750D0 (en) 1990-06-20 1990-08-08 Pfizer Ltd Therapeutic agents
GB9311920D0 (en) 1993-06-09 1993-07-28 Pfizer Ltd Therapeutic agents
GB9401090D0 (en) 1994-01-21 1994-03-16 Glaxo Lab Sa Chemical compounds
DE19642255A1 (de) 1996-10-14 1998-04-16 Bayer Ag Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten
JP4351298B2 (ja) 1996-10-14 2009-10-28 バイエル・アクチエンゲゼルシヤフト 新規へテロシクリルメチル置換ピラゾール誘導体
DE19649460A1 (de) 1996-11-26 1998-05-28 Bayer Ag Neue substituierte Pyrazolderivate
EP1049695B1 (fr) 1997-11-12 2002-02-13 Bayer Ag Imidazotriazinones a substitution 2-phenyle utilisees comme inhibiteurs des phosphodiesterases
DE19834044A1 (de) 1998-07-29 2000-02-03 Bayer Ag Neue substituierte Pyrazolderivate
DE19834047A1 (de) 1998-07-29 2000-02-03 Bayer Ag Substituierte Pyrazolderivate
DE19834045A1 (de) 1998-07-29 2000-02-03 Bayer Ag (4-Amino-5-ethylpyrimidin-2-yl)-1-(2-fluorbenzyl)-1H-pyrazolo[3,4-b]pyridin
DE19846514A1 (de) 1998-10-09 2000-04-20 Bayer Ag Neue Heterocyclyl-methyl-substituierte Pyrazole
AR031176A1 (es) 2000-11-22 2003-09-10 Bayer Ag Nuevos derivados de pirazolpiridina sustituidos con piridina
DE10057751A1 (de) 2000-11-22 2002-05-23 Bayer Ag Neue Carbamat-substituierte Pyrazolopyridinderivate
DE10057754A1 (de) 2000-11-22 2002-05-23 Bayer Ag Neue Sulfonamid-substituierte Pyrazolopyridinderivate
US6903089B1 (en) 2000-11-22 2005-06-07 Bayer Aktiengesellschaft Lactam-substituted pyrazolopyridine derivatives
DE10122894A1 (de) 2001-05-11 2002-11-14 Bayer Ag Neue Sulfonat-substituierte Pyrazolopyridinderivate
DE10132416A1 (de) 2001-07-04 2003-01-16 Bayer Ag Neue Morpholin-überbrückte Pyrazolopyridinderivate
DE10220570A1 (de) 2002-05-08 2003-11-20 Bayer Ag Carbamat-substituierte Pyrazolopyridine
DE10222550A1 (de) 2002-05-17 2003-11-27 Bayer Ag Substituierte Benzyl-pyrazolopyridine
DE10351903A1 (de) 2003-11-06 2005-06-09 Bayer Healthcare Ag Neue Kombination
DE102006021733A1 (de) 2006-05-09 2007-11-22 Bayer Healthcare Ag 3-Tetrazolylindazole und 3-Tetrazolylpyrazolopyridine sowie ihre Verwendung
DE102006043443A1 (de) * 2006-09-15 2008-03-27 Bayer Healthcare Ag Neue aza-bicyclische Verbindungen und ihre Verwendung
DE102009004245A1 (de) * 2009-01-09 2010-07-15 Bayer Schering Pharma Aktiengesellschaft Neue anellierte, Heteroatom-verbrückte Pyrazol- und Imidazol-Derivate und ihre Verwendung

Also Published As

Publication number Publication date
CA2781922A1 (fr) 2011-06-03
US8501945B2 (en) 2013-08-06
MX2012005942A (es) 2012-10-03
WO2011064156A3 (fr) 2011-10-20
ES2433236T3 (es) 2013-12-10
US20110130411A1 (en) 2011-06-02
UY33041A (es) 2011-06-30
EP2504335B1 (fr) 2013-09-04
AU2010323297A1 (en) 2012-06-14
TN2012000259A1 (en) 2013-12-12
EP2504335A2 (fr) 2012-10-03
WO2011064156A2 (fr) 2011-06-03
CN102712637A (zh) 2012-10-03
IL219861A0 (en) 2012-07-31
EA201270639A1 (ru) 2013-01-30
ECSP12011920A (es) 2012-07-31
TW201200513A (en) 2012-01-01
BR112012012618A2 (pt) 2015-09-08
CU20120083A7 (es) 2012-10-15
CO6551707A2 (es) 2012-10-31
JP2013512211A (ja) 2013-04-11
KR20120098815A (ko) 2012-09-05
DOP2012000143A (es) 2013-01-31
AR079135A1 (es) 2011-12-28

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