WO1998005640A3 - Process for the preparation of 3,3-disubstituted piperidines - Google Patents

Process for the preparation of 3,3-disubstituted piperidines Download PDF

Info

Publication number
WO1998005640A3
WO1998005640A3 PCT/EP1997/004275 EP9704275W WO9805640A3 WO 1998005640 A3 WO1998005640 A3 WO 1998005640A3 EP 9704275 W EP9704275 W EP 9704275W WO 9805640 A3 WO9805640 A3 WO 9805640A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
represents hydrogen
preparation
alkoxy
Prior art date
Application number
PCT/EP1997/004275
Other languages
French (fr)
Other versions
WO1998005640A2 (en
Inventor
Mario Grugni
Roberto Rigolio
Karl Francis Erhard
Original Assignee
Smithkline Beecham Spa
Smithkline Beecham Corp
Mario Grugni
Roberto Rigolio
Karl Francis Erhard
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
Priority claimed from GBGB9616417.3A external-priority patent/GB9616417D0/en
Priority claimed from GBGB9617594.8A external-priority patent/GB9617594D0/en
Application filed by Smithkline Beecham Spa, Smithkline Beecham Corp, Mario Grugni, Roberto Rigolio, Karl Francis Erhard filed Critical Smithkline Beecham Spa
Priority to EP97937554A priority Critical patent/EP0915849A2/en
Priority to JP10507624A priority patent/JP2000515534A/en
Publication of WO1998005640A2 publication Critical patent/WO1998005640A2/en
Publication of WO1998005640A3 publication Critical patent/WO1998005640A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00—Separation of optically-active compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

A process for preparing a compound of formula (I), wherein R1 represents hydrogen or a protecting group; and R2 represents hydrogen or benzoyl optionally substituted in the phenyl moiety with halogen, methyl or C1-4 alkoxy; which process comprises cyclising a compound of formula (II), wherein R1 is as defined in relation to (I), to provide a cyclic lactam of formula (III), wherein R1 is as defined in relation to (I); reducing the compound of formula (III) so formed to provide a compound of formula (I) wherein R2 represents hydrogen; and thereafter carrying out one or more of the following optional steps: (a) N-acylating the compound of formula (I) wherein R2 represents hydrogen to provide a compound of formula (I) wherein R2 represents benzoyl wherein the phenyl moiety is optionally substituted with halogen, methyl or C1-4 alkoxy; and (b) removing any protecting group.
PCT/EP1997/004275 1996-08-05 1997-08-04 Process for the preparation of 3,3-disubstituted piperidines WO1998005640A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP97937554A EP0915849A2 (en) 1996-08-05 1997-08-04 Process for the preparation of 3,3-disubstituted piperidines
JP10507624A JP2000515534A (en) 1996-08-05 1997-08-04 Method for producing 3,3-disubstituted piperidine

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9616417.3A GB9616417D0 (en) 1996-08-05 1996-08-05 Process
GB9616417.3 1996-08-05
GB9617594.8 1996-08-22
GBGB9617594.8A GB9617594D0 (en) 1996-08-22 1996-08-22 Process

Publications (2)

Publication Number Publication Date
WO1998005640A2 WO1998005640A2 (en) 1998-02-12
WO1998005640A3 true WO1998005640A3 (en) 1998-05-22

Family

ID=26309818

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1997/004275 WO1998005640A2 (en) 1996-08-05 1997-08-04 Process for the preparation of 3,3-disubstituted piperidines

Country Status (3)

Country Link
EP (1) EP0915849A2 (en)
JP (1) JP2000515534A (en)
WO (1) WO1998005640A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2782082B3 (en) * 1998-08-05 2000-09-22 Sanofi Sa CRYSTALLINE FORMS OF (R) - (+) - N - [[3- [1-BENZOYL-3- (3,4- DICHLOROPHENYL) PIPERIDIN-3-YL] PROP-1-YL] -4-PHENYLPIPERIDIN-4 - YL] -N-METHYLACETAMIDE (OSANETANT) AND PROCESS FOR THE PREPARATION OF SAID COMPOUND
FR2787449B3 (en) 1998-12-15 2001-01-12 Sanofi Sa 3-PHENYL-2,6-DIOXOPIPERIDIN-3-YL PROPIONAMIDE DERIVATIVES AND THEIR PREPARATION PROCESS
FR2787448B3 (en) 1998-12-18 2001-01-12 Sanofi Sa 3- (3,4-DIHALOGENOPHENYL) -2,6-DIOXOPIPERIDINE3-PROPIONIC ACID LOWER ALKYL ESTER AND METHOD OF PREPARATION

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0512901A1 (en) * 1991-05-03 1992-11-11 Sanofi Aminated polycyclic compounds and their enantiomers, process for their preparation and pharmaceutical compositions containing them
EP0673928A1 (en) * 1994-03-18 1995-09-27 Sanofi Novel N-(3,4-dichlorophenyl-propyl)-piperidine derivatives as selective human NK3-receptor antagonists

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0512901A1 (en) * 1991-05-03 1992-11-11 Sanofi Aminated polycyclic compounds and their enantiomers, process for their preparation and pharmaceutical compositions containing them
EP0673928A1 (en) * 1994-03-18 1995-09-27 Sanofi Novel N-(3,4-dichlorophenyl-propyl)-piperidine derivatives as selective human NK3-receptor antagonists

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
E. TAGMANN ET AL.: "Über in 3-Stellung basisch substituierte Pyrrolidin-, Piperidin- und Hexamethylenimin-Derivate", HELVETICA CHIMICA ACTA, vol. 35, no. 4, 16 June 1952 (1952-06-16), BASEL, CH, pages 1235 - 49, XP002048798 *
G.A.M. GIARDINA ET AL: "A reliable and efficient synthesis of SR 142801", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 6, no. 19, October 1996 (1996-10-01), OXFORD, GB, pages 2307 - 2310, XP002043892 *
H.G. CHEN ET AL.: "A practical and scalable synthesis of SR 142801, a tachykinin NK3 antagonist", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 7, no. 5, March 1997 (1997-03-01), OXFORD, GB, pages 55 - 60, XP002055505 *

Also Published As

Publication number Publication date
EP0915849A2 (en) 1999-05-19
JP2000515534A (en) 2000-11-21
WO1998005640A2 (en) 1998-02-12

Similar Documents

Publication Publication Date Title
WO1998019511A3 (en) Method for the preparation of citalopram
NO20000008L (en) Procedure for the preparation of citalopram
AU7305894A (en) A process for preparing imidazopyridine derivatives
AU6252599A (en) Resolution of trans-2 -(alkoxycarbonylethyl) -lactams useful in the synthesis of 1- (4-fluorophenyl) -3(r) -(3(s) -hydroxy-3 -(4-fluorophenyl) -propyl)) -4(s) (4-hydroxyphenyl) -2-azetidinone
DE69218330T2 (en) Process for the preparation of 1,4-dihydropyridines substituted at the 4-position
DE69427332T2 (en) Galanthamine derivative, a process for its preparation and its use as a medicament
DE60117963D1 (en) PROCESS FOR PRODUCING CITALOPRAM
CA2223634A1 (en) Preparation of n-substituted 3-hydroxypyrazoles
CA2080221A1 (en) An improved process for the preparation of substituted indolone derivatives
ATE151411T1 (en) METHOD FOR PRODUCING METHOXYMINOACETAMIDE COMPOUNDS
GB0121214D0 (en) Synthetic method
PL300685A1 (en) Carbazolone derivatives and method of obtaining sames
WO1998005640A3 (en) Process for the preparation of 3,3-disubstituted piperidines
PL315052A1 (en) Condensed dihydropyridines, method of obtaining them, their application in producing pharmaceutic preparations and pharmaceutic preparations containing such compounds
CA2427831A1 (en) Cyclization process step in the making of quinolones and naphthyridines
GB0019124D0 (en) Novel process
EP0335979A4 (en) Thienopyrimidine derivatives
SI0645388T1 (en)
WO2000018722A3 (en) New derivatives of 6-(4-phenylbutoxy)hexylamine and process for producing salmeterol
CA2222204A1 (en) Process for converting 2,4-dichloropyridines into 2-aryloxy-4-chloropyridines
IE781382L (en) Indole derivatives
ATE119533T1 (en) METHOD FOR PRODUCING 1-OXA-3, 8-DIAZA-4-OXO-SPIRO-(4,5>DECANEOUS COMPOUNDS.
DE3777464D1 (en) VITAMIN-D3 DERIVATIVES CONTAINING FLUORINE AND METHOD FOR THE PRODUCTION THEREOF.
AU681727B2 (en) Method for the preparation of 2-perfluoroalkyl-3-oxazolin- 5-one
HK1027560A1 (en) Method for producing 1,3-disubstituted 2-nitroguanidines

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): JP US

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1997937554

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1997937554

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 09230953

Country of ref document: US

WWW Wipo information: withdrawn in national office

Ref document number: 1997937554

Country of ref document: EP