KR101876594B1 - 바이시클로[2.2.2]옥탄-2-온 화합물의 제조 - Google Patents

바이시클로[2.2.2]옥탄-2-온 화합물의 제조 Download PDF

Info

Publication number
KR101876594B1
KR101876594B1 KR1020137012606A KR20137012606A KR101876594B1 KR 101876594 B1 KR101876594 B1 KR 101876594B1 KR 1020137012606 A KR1020137012606 A KR 1020137012606A KR 20137012606 A KR20137012606 A KR 20137012606A KR 101876594 B1 KR101876594 B1 KR 101876594B1
Authority
KR
South Korea
Prior art keywords
formula
compound
group
aryl
phenyl
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
KR1020137012606A
Other languages
English (en)
Korean (ko)
Other versions
KR20130138268A (ko
Inventor
슈테판 아벨레
자끄-알렉시스 퍼넬
Original Assignee
아이도시아 파마수티컬즈 리미티드
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 아이도시아 파마수티컬즈 리미티드 filed Critical 아이도시아 파마수티컬즈 리미티드
Publication of KR20130138268A publication Critical patent/KR20130138268A/ko
Application granted granted Critical
Publication of KR101876594B1 publication Critical patent/KR101876594B1/ko
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/78—Separation; Purification; Stabilisation; Use of additives
    • C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/313—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of doubly bound oxygen containing functional groups, e.g. carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
KR1020137012606A 2010-10-20 2011-10-19 바이시클로[2.2.2]옥탄-2-온 화합물의 제조 Expired - Fee Related KR101876594B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IB2010054747 2010-10-20
IBPCT/IB2010/054747 2010-10-20
PCT/IB2011/054660 WO2012052939A2 (en) 2010-10-20 2011-10-19 Preparation of bicyclo[2.2.2]octan-2-one compounds

Publications (2)

Publication Number Publication Date
KR20130138268A KR20130138268A (ko) 2013-12-18
KR101876594B1 true KR101876594B1 (ko) 2018-08-02

Family

ID=45757740

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020137012606A Expired - Fee Related KR101876594B1 (ko) 2010-10-20 2011-10-19 바이시클로[2.2.2]옥탄-2-온 화합물의 제조

Country Status (13)

Country Link
US (1) US9296673B2 (enExample)
EP (1) EP2630111B1 (enExample)
JP (1) JP5909237B2 (enExample)
KR (1) KR101876594B1 (enExample)
CN (1) CN103168019B (enExample)
CA (1) CA2813131C (enExample)
DK (1) DK2630111T3 (enExample)
ES (1) ES2536897T3 (enExample)
HU (1) HUE025195T2 (enExample)
IL (1) IL225763A (enExample)
MX (1) MX2013004427A (enExample)
TW (2) TWI511949B (enExample)
WO (1) WO2012052939A2 (enExample)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012052939A2 (en) * 2010-10-20 2012-04-26 Actelion Pharmaceuticals Ltd Preparation of bicyclo[2.2.2]octan-2-one compounds
DK2630120T3 (en) 2010-10-20 2018-10-08 Idorsia Pharmaceuticals Ltd DIASTEREOSELECTIVE PREPARATION OF BICYCLO [2.2.2] OCTAN-2-ON COMPOUNDS

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3046106A1 (de) 1980-12-06 1982-07-15 Studiengesellschaft Kohle mbH, 4330 Mülheim Optisch reine bicyclo(2.2.2)oct-5-en-2.one, verfahren zu ihrer herstellung und ihre verwendung
JP3439255B2 (ja) * 1994-03-31 2003-08-25 長瀬産業株式会社 不斉マイケル反応を触媒する金属錯体
CL2008001205A1 (es) 2007-04-27 2008-11-14 Actelion Pharmaceuticals Ltd Compuestos derivados de biciclo[2.2.2]octeno; composicion farmaceutica que los contiene; y uso en el tratamiento o prevencion de angina cronica estable, hipertension, isquemia renal y cardiaca, arritmias cardiacas, hipertrofia cardiaca y falla congestiva del corazon.
AU2009239620A1 (en) 2008-04-25 2009-10-29 Actelion Pharmaceuticals Ltd Benzimidazole derivatives as calcium channel blockers
WO2012052939A2 (en) * 2010-10-20 2012-04-26 Actelion Pharmaceuticals Ltd Preparation of bicyclo[2.2.2]octan-2-one compounds
DK2630120T3 (en) 2010-10-20 2018-10-08 Idorsia Pharmaceuticals Ltd DIASTEREOSELECTIVE PREPARATION OF BICYCLO [2.2.2] OCTAN-2-ON COMPOUNDS

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Angewandte Chemie Internationsl Edition, 2010, Vol.49, No.4, pp.676-707
Chemical Communications, 2009, No.5, pp.597-599
Synthesis, 2003, No.7, pp.1071-1078

Also Published As

Publication number Publication date
CN103168019A (zh) 2013-06-19
CA2813131C (en) 2019-02-12
DK2630111T3 (en) 2015-04-20
TW201217325A (en) 2012-05-01
TW201217324A (en) 2012-05-01
US20130211104A1 (en) 2013-08-15
TWI511949B (zh) 2015-12-11
EP2630111B1 (en) 2015-02-25
JP2013544796A (ja) 2013-12-19
CA2813131A1 (en) 2012-04-26
JP5909237B2 (ja) 2016-04-26
ES2536897T3 (es) 2015-05-29
CN103168019B (zh) 2015-05-27
EP2630111A2 (en) 2013-08-28
KR20130138268A (ko) 2013-12-18
US9296673B2 (en) 2016-03-29
IL225763A (en) 2016-04-21
TWI551583B (zh) 2016-10-01
MX2013004427A (es) 2013-07-17
WO2012052939A2 (en) 2012-04-26
WO2012052939A3 (en) 2012-06-21
IL225763A0 (en) 2013-06-27
HUE025195T2 (en) 2016-02-29

Similar Documents

Publication Publication Date Title
Flann et al. Enantioselective total synthesis of streptazolin. The tandem use of iminium ion vinylsilane cyclizations and intramolecular acylations
JP5140673B2 (ja) イソプレゴールの製造におけるフェノールリガンドの回収
Tian et al. Asymmetric catalytic carbon–carbon bond formations in a fluorous biphasic system based on perfluoroalkyl-BINOLs
Abele et al. Design and Scale-Up of a Practical Enantioselective Route to 5-Phenylbicyclo [2.2. 2] oct-5-en-2-one
Shirokane et al. Total syntheses of (±)-Gephyrotoxin and (±)-Perhydrogephyrotoxin
JPWO2017209199A1 (ja) 脂環式テトラカルボン酸二無水物の製造方法
KR101876594B1 (ko) 바이시클로[2.2.2]옥탄-2-온 화합물의 제조
Li et al. Enantioselective Intramolecular Desymmetric α‐Addition of Cyclohexanone to Propiolamide Catalyzed by Sodium L‐Prolinate
Albrow et al. Synthesis of an octahydro-1, 1′-binaphthyl thioether ligand and comparison with unhydrogenated binaphthyl analogues
KR101836552B1 (ko) 바이시클로[2.2.2]옥탄-2-온 화합물의 부분입체선택적 제조
Cabanal-Duvillard et al. A Formal Asymmetric Synthesis of (−)-Epibatidine Using a Highly Diastereoselective Hetero Diels–Alder Reaction
Zhu et al. Practical and highly stereoselective method for the preparation of several chiral arylsulfinamides and arylsulfinates based on the spontaneous crystallization of diastereomerically pure N-benzyl-N-(1-phenylethyl)-arylsulfinamides
Pandey et al. Organocatalytic dynamic kinetic resolution via conjugate addition: synthesis of chiral trans-2, 5-dialkylcyclohexanones
CN110088094A (zh) 制备立体异构纯c9-缩醛的方法
Jun et al. Diastereoselective synthesis of (2R, 4S, 5S)‐(+)‐5‐(2, 2‐dichloroacetamido)‐4‐(4‐nitrophenyl)‐2‐aryl‐1, 3‐dioxanes
PL209276B1 (pl) Sposób otrzymywania produktu reakcji Dielsa-Aldera

Legal Events

Date Code Title Description
PA0105 International application

St.27 status event code: A-0-1-A10-A15-nap-PA0105

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

A201 Request for examination
E13-X000 Pre-grant limitation requested

St.27 status event code: A-2-3-E10-E13-lim-X000

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

PN2301 Change of applicant

St.27 status event code: A-3-3-R10-R13-asn-PN2301

St.27 status event code: A-3-3-R10-R11-asn-PN2301

D13-X000 Search requested

St.27 status event code: A-1-2-D10-D13-srh-X000

D14-X000 Search report completed

St.27 status event code: A-1-2-D10-D14-srh-X000

E902 Notification of reason for refusal
PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

E701 Decision to grant or registration of patent right
PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

GRNT Written decision to grant
PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U12-oth-PR1002

Fee payment year number: 1

PG1601 Publication of registration

St.27 status event code: A-4-4-Q10-Q13-nap-PG1601

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 4

PR1001 Payment of annual fee

St.27 status event code: A-4-4-U10-U11-oth-PR1001

Fee payment year number: 5

PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 20230704

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 20230704