CA2980071A1 - Method for preparation of (4s)-4-[4-cyano-2-(methylsulfonyl)phenyl]-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro pyrimidine-5-carbonitrile - Google Patents

Method for preparation of (4s)-4-[4-cyano-2-(methylsulfonyl)phenyl]-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro pyrimidine-5-carbonitrile Download PDF

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Publication number
CA2980071A1
CA2980071A1 CA2980071A CA2980071A CA2980071A1 CA 2980071 A1 CA2980071 A1 CA 2980071A1 CA 2980071 A CA2980071 A CA 2980071A CA 2980071 A CA2980071 A CA 2980071A CA 2980071 A1 CA2980071 A1 CA 2980071A1
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Prior art keywords
formula
compound
reaction
reacts
stands
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CA2980071A
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English (en)
French (fr)
Inventor
Heiko Schirmer
Philipp Rubenbauer
Birgit Keil
Britta Olenik
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pH Pharma Co Ltd
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Bayer Pharma AG
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Publication of CA2980071A1 publication Critical patent/CA2980071A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2980071A 2015-03-18 2016-03-15 Method for preparation of (4s)-4-[4-cyano-2-(methylsulfonyl)phenyl]-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro pyrimidine-5-carbonitrile Pending CA2980071A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP15159570 2015-03-18
EP15159570.9 2015-03-18
PCT/EP2016/055498 WO2016146607A1 (de) 2015-03-18 2016-03-15 Verfahren zur herstellung von (4s)-4-[4-cyano-2-(methylsulfonyl)phenyl]-3,6-dimethyl-2-oxo-1-[3-(trifluormethyl)phenyl]-1,2,3,4-tetrahydro pyrimidin-5-carbonitril

Publications (1)

Publication Number Publication Date
CA2980071A1 true CA2980071A1 (en) 2016-09-22

Family

ID=52684127

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2980071A Pending CA2980071A1 (en) 2015-03-18 2016-03-15 Method for preparation of (4s)-4-[4-cyano-2-(methylsulfonyl)phenyl]-3,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro pyrimidine-5-carbonitrile

Country Status (9)

Country Link
US (2) US10316001B2 (enExample)
EP (1) EP3271337B1 (enExample)
JP (4) JP7390100B2 (enExample)
KR (1) KR20170129191A (enExample)
CN (2) CN110981815A (enExample)
AU (1) AU2016232270B2 (enExample)
CA (1) CA2980071A1 (enExample)
ES (1) ES2877583T3 (enExample)
WO (1) WO2016146607A1 (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7390100B2 (ja) 2015-03-18 2023-12-01 ピーエイチ・ファーマ・カンパニー・リミテッド （４ｓ）－４－［４－シアノ－２－（メチルスルホニル）フェニル］－３，６－ジメチル－２－オキソ－１－［３－（トリフルオロメチル）フェニル］－１，２，３，４－テトラヒドロピリミジン－５－カルボニトリルの製造方法
AU2019257632A1 (en) * 2018-04-24 2020-11-26 Ph Pharma Co., Ltd. Use of neutrophil elastase inhibitors in liver disease
AU2020340281A1 (en) * 2019-08-23 2022-04-07 Ph Pharma Co., Ltd. Use of a neutrophil elastase inhibitor in lung disease
CN112304919B (zh) * 2020-09-18 2022-07-05 公安部物证鉴定中心 一种乌头碱类植物毒素的定性定量检测方法

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GB9214053D0 (en) 1992-07-02 1992-08-12 Ici Plc Heterocyclic amides
US6372936B1 (en) * 1999-06-09 2002-04-16 Eli Lilly And Company Optical resolution of aminoisobobutyric acid
MY125533A (en) 1999-12-06 2006-08-30 Bristol Myers Squibb Co Heterocyclic dihydropyrimidine compounds
GB0219896D0 (en) 2002-08-27 2002-10-02 Bayer Ag Dihydropyridine derivatives
WO2004024701A1 (en) 2002-09-10 2004-03-25 Bayer Healthcare Ag Heterocyclic derivatives
MXPA05002644A (es) 2002-09-10 2005-09-20 Bayer Healthcare Ag Derivados de pirimidinona como agentes terapeuticos contra procesos de remodelacion, isquemicos e inflamatorios agudos y cronicos.
GB0220962D0 (en) * 2002-09-10 2002-10-23 Bayer Ag Heterocyclic derivatives
AU2003290735A1 (en) 2002-12-06 2004-06-30 Eli Lilly And Company Inhibitors of monoamine uptake
US7166603B2 (en) 2003-07-23 2007-01-23 Bristol-Myers Squibb Co. Dihydropyrimidone inhibitors of calcium channel function
WO2005082863A2 (en) * 2004-02-26 2005-09-09 Bayer Healthcare Ag 1,4 diaryl-dihydropyrimidin-2 ones and their use as a human neutrophil elastase inhibitors
ES2394177T3 (es) 2004-02-26 2013-01-23 Bayer Intellectual Property Gmbh 1,4-diaril-dihidropirimidin-2-onas y su uso como inhibidores de elastasa de neutrófilos humanos
GB0502258D0 (en) 2005-02-03 2005-03-09 Argenta Discovery Ltd Compounds and their use
GB0512940D0 (en) 2005-06-24 2005-08-03 Argenta Discovery Ltd Compounds and their use
GB0520743D0 (en) 2005-10-12 2005-11-23 Argenta Discovery Ltd Compounds and their use
MX2008007248A (es) * 2005-12-05 2008-09-03 Wyeth Corp Proceso para preparar derivados de cicloalcanol arilo sustituidos.
DE602007009095D1 (de) 2006-05-04 2010-10-21 Pulmagen Therapeutics Inflamma Tetrahydropyrrolopyrimidindione und ihre verwendung als inhibitoren der humanen neutrophilen elastase
US20100010024A1 (en) 2006-07-01 2010-01-14 Bayer Healthcare Ag Use of1,4-diaryl-dihydropyrimidine-2-on derivatives for treating pulmonary arterial hypertension
EP2064184A1 (en) 2006-09-04 2009-06-03 AstraZeneca AB Multimeric heterocyclic compounds useful as neutrophil elastase inhibitors
DE102008022521A1 (de) 2008-05-07 2009-11-12 Bayer Schering Pharma Aktiengesellschaft 1,4-Diaryl-pyrimidopyridazin-2,5-dione und ihre Verwendung
SG186679A1 (en) 2007-12-20 2013-01-30 Bayer Schering Pharma Ag 4-(4-cyano-2-thioaryl)dihydropyrimidinones and use thereof
DE102009016553A1 (de) 2009-04-06 2010-10-07 Bayer Schering Pharma Aktiengesellschaft Sulfonamid- und Sulfoximin-substituierte Diaryldihydropyrimidinone und ihre Verwendung
JP7390100B2 (ja) 2015-03-18 2023-12-01 ピーエイチ・ファーマ・カンパニー・リミテッド （４ｓ）－４－［４－シアノ－２－（メチルスルホニル）フェニル］－３，６－ジメチル－２－オキソ－１－［３－（トリフルオロメチル）フェニル］－１，２，３，４－テトラヒドロピリミジン－５－カルボニトリルの製造方法

Also Published As

Publication number Publication date
JP2021138711A (ja) 2021-09-16
US20190248750A1 (en) 2019-08-15
US10316001B2 (en) 2019-06-11
KR20170129191A (ko) 2017-11-24
JP7125450B2 (ja) 2022-08-24
AU2016232270B2 (en) 2020-09-03
EP3271337B1 (de) 2021-03-03
WO2016146607A1 (de) 2016-09-22
AU2016232270A1 (en) 2017-10-19
JP2018508549A (ja) 2018-03-29
JP7117415B2 (ja) 2022-08-12
CN110981815A (zh) 2020-04-10
CN107635972A (zh) 2018-01-26
EP3271337A1 (de) 2018-01-24
JP2022145951A (ja) 2022-10-04
ES2877583T3 (es) 2021-11-17
US20180072685A1 (en) 2018-03-15
JP2020172529A (ja) 2020-10-22
US10676443B2 (en) 2020-06-09
JP7390100B2 (ja) 2023-12-01

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