JP6368351B2 - ジフルオロラクタムアナログを合成する方法 - Google Patents

ジフルオロラクタムアナログを合成する方法 Download PDF

Info

Publication number
JP6368351B2
JP6368351B2 JP2016502940A JP2016502940A JP6368351B2 JP 6368351 B2 JP6368351 B2 JP 6368351B2 JP 2016502940 A JP2016502940 A JP 2016502940A JP 2016502940 A JP2016502940 A JP 2016502940A JP 6368351 B2 JP6368351 B2 JP 6368351B2
Authority
JP
Japan
Prior art keywords
compound
alkyl
formula
methyl
group
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.)
Expired - Fee Related
Application number
JP2016502940A
Other languages
English (en)
Japanese (ja)
Other versions
JP2016519669A5 (https=
JP2016519669A (ja
Inventor
バーレット，スティーヴン・ダグラス
コロンボ，ジョセフ・マイケル
ジャーメイン，ブラッドリー・デーヴィッド
コルニロフ，アンドリー
クレイマー，ジェームズ・バーナード
ウジーブロ，アダム
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cayman Chemical Co Inc
Original Assignee
Cayman Chemical Co Inc
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 Cayman Chemical Co Inc filed Critical Cayman Chemical Co Inc
Publication of JP2016519669A publication Critical patent/JP2016519669A/ja
Publication of JP2016519669A5 publication Critical patent/JP2016519669A5/ja
Application granted granted Critical
Publication of JP6368351B2 publication Critical patent/JP6368351B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (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)
  • Pyrrole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
JP2016502940A 2013-03-15 2014-03-14 ジフルオロラクタムアナログを合成する方法 Expired - Fee Related JP6368351B2 (ja)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361799334P 2013-03-15 2013-03-15
US61/799,334 2013-03-15
PCT/US2014/028933 WO2014144500A2 (en) 2013-03-15 2014-03-14 Methods of synthesizing a difluorolactam analog

Publications (3)

Publication Number Publication Date
JP2016519669A JP2016519669A (ja) 2016-07-07
JP2016519669A5 JP2016519669A5 (https=) 2017-04-20
JP6368351B2 true JP6368351B2 (ja) 2018-08-01

Family

ID=50693998

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2016502940A Expired - Fee Related JP6368351B2 (ja) 2013-03-15 2014-03-14 ジフルオロラクタムアナログを合成する方法

Country Status (7)

Country Link
US (3) US9914725B2 (https=)
EP (1) EP2970234B1 (https=)
JP (1) JP6368351B2 (https=)
AU (1) AU2014229065B2 (https=)
CA (1) CA2903314C (https=)
IL (1) IL241042B (https=)
WO (1) WO2014144500A2 (https=)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014015247A1 (en) * 2012-07-19 2014-01-23 Cayman Chemical Company, Inc. Difluorolactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated disease and conditions
HU231033B1 (hu) * 2016-03-22 2019-12-30 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Eljárás 3-as kötést tartalmazó optikailag aktív karbonsavak, karbonsav sók és karbonsav származékok előállítására
CN106699604B (zh) * 2017-01-09 2019-01-01 四川同晟生物医药有限公司 一种沙库比曲及其中间体的制备方法

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3975399A (en) 1974-08-06 1976-08-17 E. I. Du Pont De Nemours And Company 1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones
DE2517771A1 (de) 1975-04-18 1976-10-28 Schering Ag Neue prostaglandin-acetylen-analoga und verfahren zu ihrer herstellung
CA1085859A (en) 1975-06-27 1980-09-16 Wilhelm Bartmann Pyrrolidones and process for their manufacture
DE2528664A1 (de) 1975-06-27 1977-01-13 Hoechst Ag Pyrrolidone und verfahren zu ihrer herstellung
DE2619638A1 (de) 1976-05-04 1977-11-17 Hoechst Ag Pyrrolidone und verfahren zu ihrer herstellung
US4177346A (en) 1976-08-06 1979-12-04 Pfizer Inc. 1,5-Disubstituted-2-pyrrolidones
US4320136A (en) 1980-08-11 1982-03-16 E. I. Du Pont De Nemours And Company 8-Aza-16,16-difluoroprostanoids
US4311644A (en) * 1981-01-30 1982-01-19 E. R. Squibb & Sons, Inc. Method for preparing 10,10-difluoro prostacyclin intermediates and new compounds produced thereby
US4456613A (en) 1982-12-27 1984-06-26 E. I. Du Pont De Nemours And Company 6-Keto- and 6-hydroxy-8-azaprostanoids and anti-ulcer use thereof
OA12533A (en) 2000-11-27 2006-06-05 Pfizer Prod Inc Ep4 receptor selective agonists in the treatment of osteoporosis.
AU2002226035A1 (en) * 2000-12-07 2002-06-18 Michael P Doyle Lewis acid catalysis using chiral metal complexes
CA2451392A1 (en) 2001-07-16 2003-01-30 F. Hoffmann-La Roche Ag Prostaglandin analogues as ep4 receptor agonists
CN100371322C (zh) 2001-07-16 2008-02-27 霍夫曼-拉罗奇有限公司 作为前列腺素类化合物激动剂的2-吡咯烷酮衍生物
EP2255829A3 (en) * 2001-07-23 2012-03-28 Ono Pharmaceutical Co., Ltd. Pharmaceutical composition for treatment of diseases associated with decrease in bone mass comprising EP4 agonist as active ingredient
EP1461026A2 (en) 2001-12-03 2004-09-29 Merck & Co., Inc. Method for treating ocular hypertension
WO2003077910A1 (en) 2002-03-18 2003-09-25 Pfizer Products Inc. Methods of treatment with selective ep4 receptor agonists
AU2003233729B2 (en) 2002-06-06 2007-10-04 Merck Frosst Canada Ltd 1,5-distributed pyrrolid-2-one derivatives for use as EP4 receptor agonists in the treatment of eye diseases such as glaucoma
JP4754820B2 (ja) 2002-06-10 2011-08-24 メルク セローノ ソシエテ アノニム プロスタグランジン作動薬としてのγラクタムおよびその使用
US20060167081A1 (en) 2002-10-25 2006-07-27 Xavier Billot Ep4 receptor agonists
ES2305779T3 (es) 2003-03-03 2008-11-01 Laboratoires Serono Sa Derivados de g-lactama como agonistas de prostaglandinas.
KR20100044251A (ko) 2007-08-15 2010-04-29 싸이토키네틱스, 인코포레이티드 특정 화학 물질, 조성물 및 방법
WO2009055289A2 (en) 2007-10-23 2009-04-30 Allergan, Inc. Therapeutic substituted lactams
US20120270934A1 (en) 2009-07-03 2012-10-25 Concert Pharmaceuticals, Inc. Prostacyclin derivatives
CN103201261A (zh) 2010-11-10 2013-07-10 埃科特莱茵药品有限公司 用作为食欲素受体拮抗剂的内酰胺衍生物
EP2729445B1 (en) * 2011-07-04 2015-10-21 Rottapharm Biotech S.r.l. Cyclic amine derivatives as ep4 receptor antagonists
WO2014015247A1 (en) * 2012-07-19 2014-01-23 Cayman Chemical Company, Inc. Difluorolactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated disease and conditions

Also Published As

Publication number Publication date
US11345690B2 (en) 2022-05-31
EP2970234B1 (en) 2018-07-18
US20190202816A1 (en) 2019-07-04
US9914725B2 (en) 2018-03-13
JP2016519669A (ja) 2016-07-07
WO2014144500A2 (en) 2014-09-18
US20180170918A1 (en) 2018-06-21
HK1215022A1 (en) 2016-08-12
CA2903314A1 (en) 2014-09-18
AU2014229065B2 (en) 2017-03-09
CA2903314C (en) 2023-02-14
AU2014229065A1 (en) 2015-09-17
IL241042B (en) 2021-10-31
US20160060253A1 (en) 2016-03-03
EP2970234A2 (en) 2016-01-20
US20220127252A9 (en) 2022-04-28
IL241042A0 (en) 2015-11-30
WO2014144500A3 (en) 2015-05-28

Similar Documents

Publication Publication Date Title
KR20140035484A (ko) 베라프로스트의 제조 방법
JP7659630B2 (ja) 大環状ｍｃｌ１阻害剤を調製するための方法及び中間体
JP2002536450A (ja) エポチロン誘導体、それらの製造方法、及びそれらの医薬としての使用
ES2875551T3 (es) Método para preparar (R)-4-n-propil-dihidrofuran-2(3H)-ona ópticamente pura
JP6368351B2 (ja) ジフルオロラクタムアナログを合成する方法
Blaauw et al. Intramolecular [2+ 2] photocycloadditions as an approach towards the right-hand side of solanoeclepin A
TWI880924B (zh) 製備(6r,10s)-10-{4-[5-氯-2-(4-氯-1h-1,2,3-三唑-1-基)苯基]-6-側氧基-1(6h)-嘧啶基}-1-(二氟甲基)-6-甲基-1,4,7,8,9,10-六氫-11,15-(亞甲橋基)吡唑并[4,3-b][1,7]二氮雜環十四炔-5(6h)-酮之新穎合成選項
Deng et al. Preparation of (3S, 4S)-1-Benzhydryl-3-[(5R)-1′-hydroxyethyl]-4-acyl-2-azetidinones from (2R, 3R)-Epoxybutyramide Precursors
WO2000035898A1 (en) HYDRONAPHTHO[2,3-c]FURAN DERIVATIVES AND PROCESS FOR THE PREPARATION THEREOF
TW200530178A (en) Processes for preparing bicyclo [3.1.0] hexane derivatives, and intermediates thereto
WO2014108011A1 (zh) 恩替卡韦中间体及其制备方法
TW201408633A (zh) 製備他氟前列腺素（ｔａｆｌｕｐｒｏｓｔ）之方法及其之中間體
JP6621755B2 (ja) ユーシェアリライド類の製造方法
JP7063487B2 (ja) ピラン縮合環系化合物、その製造方法及び使用
Mohammad Total synthesis of rubriflordilactone B and pseudo-rubriflordilactone B
El-Awa Asymmetric synthesis of dipropionate stereotetrads and application towards the total synthesis of Aplyronine A
JP2008513437A (ja) 有用な中間体の新規製造方法
Takagi et al. Stereoselective syntheses of (+)-rhopaloic acid A and (–)-ent-and (±)-rac-rhopaloic acid A
Aimon A NHK approach towards the total synthesis of the cornexistins
Csuk et al. From a glycal to a [1, 3] dioxolan-4-yl ester
Jansone-Popova Synthesis of Polycyclic Ring Systems Via CH Bond Insertion and Enantioselective Conjugate Addition
Mohammed Enantioselective Total Synthesis of (+)-Sieboldine A via Diastereoselective Pauson-Khand Reaction
Mathieson A flexible one-step synthesis of dienamides: approaches towards a total synthesis of the Crocacins
HK1215022B (en) Methods of synthesizing a difluorolactam analog
CN105541779A (zh) 一种海洋天然产物Haterumadienone的合成方法

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20170314

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20170314

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20180131

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20180207

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20180507

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20180607

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20180706

R150 Certificate of patent or registration of utility model

Ref document number: 6368351

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

LAPS Cancellation because of no payment of annual fees