CA2240927A1 - Process for production of piperidine derivatives - Google Patents

Process for production of piperidine derivatives

Info

Publication number
CA2240927A1
CA2240927A1 CA002240927A CA2240927A CA2240927A1 CA 2240927 A1 CA2240927 A1 CA 2240927A1 CA 002240927 A CA002240927 A CA 002240927A CA 2240927 A CA2240927 A CA 2240927A CA 2240927 A1 CA2240927 A1 CA 2240927A1
Authority
CA
Canada
Prior art keywords
hydrogen
group
different
same
alkyl
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.)
Granted
Application number
CA002240927A
Other languages
French (fr)
Other versions
CA2240927C (en
Inventor
Thomas E. D'ambra
Garry M. Pilling
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.)
Curia Global Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2240927A1 publication Critical patent/CA2240927A1/en
Application granted granted Critical
Publication of CA2240927C publication Critical patent/CA2240927C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • 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
    • C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • 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
    • 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4

Abstract

The present invention relates to a process for preparing piperidine derivative compounds of formulae (I, II), wherein n is 0 or 1; R1 is hydrogen or hydroxy; R2 is hydrogen; or, when n is 0, R1 and R2 taken together form a second bond between the carbon atoms bearing R' and R2, provided that when n is 1, R1 and R2 are each hydrogen; R3 is -COOH
or -COOR4; R4 is an alkyl or aryl moiety; A, B, and D are the substituents of their rings, each of which may be different or the same, and are selected from the group consisting of hydrogen, halogens, alkyl, hydroxy, alkoxy, and other substituents. The process comprises providing a regioisomer of formula (III), wherein Z is -CG1G2G3 (IV) or (V), m is an integer from 1 to 6; Q and Y are the same or different and are selected from the group consisting of O, S and NR5; G1, G2, and G3 are the same or different and are selected from the group consisting of OR8, SR8, and NR8R9; R6 and R7 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, an aryl moiety, OR8, SR8, and NR8R9; and R5, R8, and R9 are the same or different and are selected from the group consisting of hydrogen, an alkyl moiety, and an aryl moiety and converting the regioisomer to the piperidine derivative compound with a piperidine compound.
CA002240927A 1995-12-21 1996-12-19 Process for production of piperidine derivatives Expired - Lifetime CA2240927C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/576,068 US6153754A (en) 1995-12-21 1995-12-21 Process for production of piperidine derivatives
US08/576,068 1995-12-21
PCT/US1996/020189 WO1997023213A1 (en) 1995-12-21 1996-12-19 Process for production of piperidine derivatives

Publications (2)

Publication Number Publication Date
CA2240927A1 true CA2240927A1 (en) 1997-07-03
CA2240927C CA2240927C (en) 2006-08-22

Family

ID=24302845

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002240927A Expired - Lifetime CA2240927C (en) 1995-12-21 1996-12-19 Process for production of piperidine derivatives

Country Status (15)

Country Link
US (7) US6153754A (en)
EP (1) EP0868182B1 (en)
JP (2) JP4865114B2 (en)
KR (2) KR100516868B1 (en)
AT (1) ATE248595T1 (en)
AU (1) AU723231B2 (en)
BR (1) BR9612216A (en)
CA (1) CA2240927C (en)
DE (1) DE69629831T2 (en)
DK (1) DK0868182T3 (en)
ES (1) ES2206618T3 (en)
NO (1) NO311717B1 (en)
NZ (1) NZ326085A (en)
PT (1) PT868182E (en)
WO (1) WO1997023213A1 (en)

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CN1275916C (en) * 1993-06-25 2006-09-20 阿温蒂斯公司 Novel intermediates useful for the preparation of antihistaminic piperidine derivatives
US6201124B1 (en) 1995-12-21 2001-03-13 Albany Molecular Research, Inc. Process for production of piperidine derivatives
US6153754A (en) 1995-12-21 2000-11-28 Albany Molecular Research, Inc. Process for production of piperidine derivatives
ES2151442B1 (en) * 1999-01-11 2001-07-01 Espanola Prod Quimicos NEW DERIVATIVE OF BENCENOETHANOL.
EP1377912A4 (en) * 2001-02-22 2007-11-14 Classen Immunotherapies Inc Improved algorithms and methods for products safety
US20030021849A1 (en) * 2001-04-09 2003-01-30 Ben-Zion Dolitzky Polymorphs of fexofenadine hydrochloride
CA2444456A1 (en) * 2001-04-09 2002-10-17 Teva Pharmaceutical Industries Ltd. Polymorphs of fexofenadine hydrochloride
ITRM20010260A1 (en) 2001-05-17 2002-11-18 Dinamite Dipharma S P A In For PROCESS FOR THE PREPARATION OF PHEXOPHENADINE OR ACID 4 1-HYDROXY-4-4- (HYDROXYDIDENYLMETHYL) -1-PIPERIDINYL | -BUTYL | -ALPHA, ALPHA-DIMETHYLBENZ
WO2002102777A2 (en) * 2001-06-18 2002-12-27 Dr. Reddy's Laboratories Ltd. NOVEL CRYSTALLINE FORMS OF 4-[4-[4-(HYDROXYDIPHENYLMETHYL)-1-PIPERINDINYL]-1-HYDROXYBUTYL]-α, α-DIMETHYLBENZENE ACETIC ACID AND ITS HYDROCHLORIDE
US7700779B2 (en) 2001-06-18 2010-04-20 Dr. Reddy's Laboratories Limited Crystalline forms of fexofenadine and its hydrochloride
TWI263497B (en) * 2002-03-29 2006-10-11 Lilly Co Eli Pyridinoylpiperidines as 5-HT1F agonists
JP2005532356A (en) * 2002-06-10 2005-10-27 テバ ファーマシューティカル インダストリーズ リミティド Polymorph XVI of fexofenadine hydrochloride
TW200517114A (en) 2003-10-15 2005-06-01 Combinatorx Inc Methods and reagents for the treatment of immunoinflammatory disorders
CA2560882A1 (en) * 2004-04-26 2005-11-03 Teva Pharmaceutical Industries Ltd. Crystalline forms of fexofenadine hydrochloride and processes for their preparation
US7498443B2 (en) * 2004-09-17 2009-03-03 Albany Molecular Research, Inc. Process for production of carebastine
JP2008514641A (en) * 2004-09-28 2008-05-08 テバ ファーマシューティカル インダストリーズ リミティド Crystalline fexofenadine and method for its preparation
NZ568694A (en) 2005-11-09 2011-09-30 Zalicus Inc Method, compositions, and kits for the treatment of medical conditions
ITMI20061492A1 (en) * 2006-07-27 2008-01-28 Archimica Srl PROCESS FOR THE PREPARATION OF FEXOPHENADINE.
ITMI20070987A1 (en) 2007-05-16 2008-11-17 Dipharma Francis Srl PROCEDURE FOR THE PREPARATION OF KETONIC COMPOUNDS
WO2010021681A2 (en) * 2008-08-18 2010-02-25 Combinatorx (Singapore) Pte. Ltd. Compositions and methods for treatment of viral diseases
EP2289867A3 (en) 2009-08-19 2012-04-25 Jubilant Organosys Limited A process for producing 4-(4-halo-1-oxybutyl)-alpha,alpha-dimethylbenzene acetic acid or alkyl esters thereof
US20110130711A1 (en) * 2009-11-19 2011-06-02 Follica, Inc. Hair growth treatment
JP6328242B2 (en) 2013-08-14 2018-05-23 マイトラル・ヴァルヴ・テクノロジーズ・エス・アー・エール・エル System for heart valve replacement

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Also Published As

Publication number Publication date
DE69629831D1 (en) 2003-10-09
PT868182E (en) 2004-02-27
US8476445B2 (en) 2013-07-02
US20070010677A1 (en) 2007-01-11
NO982770L (en) 1998-06-16
KR20050052550A (en) 2005-06-02
US20100137605A1 (en) 2010-06-03
DE69629831T2 (en) 2004-07-15
DK0868182T3 (en) 2003-12-15
KR19990076650A (en) 1999-10-15
NZ326085A (en) 2001-04-27
US6458958B1 (en) 2002-10-01
JP2009019058A (en) 2009-01-29
ES2206618T3 (en) 2004-05-16
KR100516868B1 (en) 2005-11-25
EP0868182A1 (en) 1998-10-07
AU723231B2 (en) 2000-08-24
NO982770D0 (en) 1998-06-16
CA2240927C (en) 2006-08-22
ATE248595T1 (en) 2003-09-15
US7678915B2 (en) 2010-03-16
US6919458B2 (en) 2005-07-19
EP0868182B1 (en) 2003-09-03
JP2000502348A (en) 2000-02-29
US20050209279A1 (en) 2005-09-22
AU1337197A (en) 1997-07-17
WO1997023213A1 (en) 1997-07-03
NO311717B1 (en) 2002-01-14
US6444824B1 (en) 2002-09-03
EP0868182A4 (en) 1999-04-07
US20030028029A1 (en) 2003-02-06
BR9612216A (en) 1999-12-28
KR100573943B1 (en) 2006-04-26
US6153754A (en) 2000-11-28
JP4865114B2 (en) 2012-02-01

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