TWI225476B - Novel process of preparing tolterodine and analogues thereof, and novel intermediates prepared therein - Google Patents

Novel process of preparing tolterodine and analogues thereof, and novel intermediates prepared therein Download PDF

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Publication number
TWI225476B
TWI225476B TW089128081A TW89128081A TWI225476B TW I225476 B TWI225476 B TW I225476B TW 089128081 A TW089128081 A TW 089128081A TW 89128081 A TW89128081 A TW 89128081A TW I225476 B TWI225476 B TW I225476B
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formula
compound
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scope
item
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TW089128081A
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English (en)
Chinese (zh)
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Pher G Andersson
Christian Hedberg
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Pharmacia Ab
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
    • C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
    • 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
    • C07C29/143—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 ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
    • C07C35/32—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.3.0) system, e.g. indenols
    • 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
    • C07C45/511—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 involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—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 involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • 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
    • 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
    • C07C45/68—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 by increase in the number of carbon atoms
    • C07C45/72—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—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 by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Urology & Nephrology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Pyrane Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
TW089128081A 1999-12-30 2000-12-28 Novel process of preparing tolterodine and analogues thereof, and novel intermediates prepared therein TWI225476B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SE9904850A SE9904850D0 (sv) 1999-12-30 1999-12-30 Novel process and intermediates

Publications (1)

Publication Number Publication Date
TWI225476B true TWI225476B (en) 2004-12-21

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TW089128081A TWI225476B (en) 1999-12-30 2000-12-28 Novel process of preparing tolterodine and analogues thereof, and novel intermediates prepared therein

Country Status (29)

Country Link
US (1) US6310248B2 (OSRAM)
EP (2) EP1242361B1 (OSRAM)
JP (1) JP2003519207A (OSRAM)
KR (1) KR20020062669A (OSRAM)
CN (1) CN1209342C (OSRAM)
AR (1) AR027138A1 (OSRAM)
AT (1) ATE282019T1 (OSRAM)
AU (1) AU782796B2 (OSRAM)
BR (1) BR0016785A (OSRAM)
CA (1) CA2392832A1 (OSRAM)
CZ (1) CZ20022255A3 (OSRAM)
DE (1) DE60015799T2 (OSRAM)
DK (1) DK1242361T3 (OSRAM)
EE (1) EE200200325A (OSRAM)
ES (1) ES2228658T3 (OSRAM)
HU (1) HUP0203816A3 (OSRAM)
IL (1) IL150275A0 (OSRAM)
MX (1) MXPA02006415A (OSRAM)
MY (1) MY118906A (OSRAM)
NO (1) NO20023189L (OSRAM)
NZ (1) NZ519079A (OSRAM)
PE (1) PE20011123A1 (OSRAM)
PL (1) PL355947A1 (OSRAM)
PT (1) PT1242361E (OSRAM)
SE (1) SE9904850D0 (OSRAM)
SK (1) SK9392002A3 (OSRAM)
TW (1) TWI225476B (OSRAM)
WO (1) WO2001049649A1 (OSRAM)
ZA (1) ZA200204066B (OSRAM)

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EP0957073A1 (en) * 1998-05-12 1999-11-17 Schwarz Pharma Ag Novel derivatives of 3,3-diphenylpropylamines
WO2003064501A1 (en) * 2002-01-31 2003-08-07 Clarke Slemon Conformationally restricted compounds as dendrimer cores
US6703504B2 (en) 2002-02-11 2004-03-09 Clarke Slemon Conformationally constrained compounds as dendrimer cores
EP1424079A1 (en) * 2002-11-27 2004-06-02 Boehringer Ingelheim International GmbH Combination of a beta-3-receptor agonist and of a reuptake inhibitor of serotonin and/or norepinephrine
DE10315917A1 (de) * 2003-04-08 2004-11-18 Schwarz Pharma Ag Hochreine Basen von 3,3-Diphenylpropylaminmonoestern
ITMI20031354A1 (it) * 2003-07-02 2005-01-03 Istituto Di Chimica Biomolecolare D El Cnr Sezione Sintesis enantioselettiva di composti enantiomericamente arricchiti.
ES2235648B1 (es) * 2003-12-22 2006-11-01 Ragactives, S.L. Procedimiento para la obtencion de tolterodina.
ITMI20040616A1 (it) * 2004-03-30 2004-06-30 Dinamite Dipharma S P A In For Processo per la preparazione di tolterodina e suoi intermedi
EP1629834A1 (en) 2004-08-27 2006-03-01 KRKA, D.D., Novo Mesto Sustained release pharmaceutical composition of tolterodine
ITMI20041920A1 (it) * 2004-10-11 2005-01-11 Chemi Spa Processo per la preparazione di n, n-diisopropil-3-2-idrossi-5-metilfenil-3-fenil-propabammina
JP4513535B2 (ja) * 2004-12-03 2010-07-28 住友化学株式会社 トルテロジンの製造方法
WO2006066931A1 (en) * 2004-12-24 2006-06-29 Lek Pharmaceuticals D.D. Process for preparation of 3-(2-hydroxy-5-methylphenyl)-n,n-diisopropyl-3­phenylpropylamine
US7528267B2 (en) 2005-08-01 2009-05-05 Girindus America, Inc. Method for enantioselective hydrogenation of chromenes
ES2268987B1 (es) 2005-08-05 2008-02-01 Ragactives, S.L. Procedimiento para la obtencion de 3,3-difenilpropilaminas.
KR100647068B1 (ko) 2005-09-15 2006-11-23 하나제약 주식회사 라세믹ｎ,ｎ-디이소프로필-3-(2-히드록시-5-메틸페닐)-3-페닐프로판아민의 제조방법
KR100686351B1 (ko) * 2006-01-12 2007-02-22 주식회사 카이로제닉스 톨테로딘 라세미체의 제조방법
ATE480531T1 (de) 2006-05-24 2010-09-15 Pfizer Ltd Verfahren zur herstellung von benzopyran-2- olderivaten
EA018376B1 (ru) 2006-06-12 2013-07-30 Шварц Фарма Аг Новые хиральные промежуточные продукты, способ их получения и их применение в производстве толтеродина, фезотеродина или их активных метаболитов
KR100717361B1 (ko) * 2006-08-07 2007-05-11 주식회사 카이로제닉스 톨테로딘 라세미체 및 이의 중간체의 제조방법
EP2175843B1 (en) 2007-08-08 2014-10-08 Inventia Healthcare Private Limited Extended release compositions comprising tolterodine
EP2334378B1 (en) 2008-08-19 2014-04-09 XenoPort, Inc. Prodrugs of methyl hydrogen fumarate, pharmaceutical compositions thereof, and methods of use
NZ593676A (en) 2008-12-24 2012-06-29 Daiichi Sankyo Co Ltd Calcium-sensing receptor antagonists
EP2374794B1 (en) 2008-12-24 2015-11-04 Daiichi Sankyo Company, Limited Cyclic amine compounds
KR101275984B1 (ko) * 2010-10-18 2013-06-18 경기대학교 산학협력단 광학활성을 갖는 크로만계 유도체 및 이의 제조방법
WO2012063843A1 (ja) * 2010-11-09 2012-05-18 株式会社カネカ ハロゲン化インデノン類及びそれを用いた光学活性インダノン類又は光学活性インダノール類の製造方法
WO2012098044A1 (en) 2011-01-17 2012-07-26 Cambrex Profarmaco Milano S.R.L. Process for the preparation of n,n-diisopropyl-3-(2-hydroxy-5-methylphenyl)- 3-phenyl propylamine and its salts starting from a novel intermediate
EP2476665A1 (en) 2011-01-17 2012-07-18 Cambrex Profarmaco Milano S.r.l. Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)- 3-phenyl propylamine and its salts starting from a novel intermediate
EA024651B1 (ru) 2011-06-20 2016-10-31 Х. Лундбекк А/С Дейтерированные 1-пиперазино-3-фенилинданы, применяемые для лечения шизофрении
CN103159657B (zh) * 2011-12-08 2016-06-29 重庆华邦胜凯制药有限公司 一种定向合成不饱和共轭醇的方法
AR094054A1 (es) * 2012-12-19 2015-07-08 H Lundbeck As 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma
KR101380982B1 (ko) 2013-04-29 2014-04-10 경기대학교 산학협력단 광학활성을 갖는 크로만-2-올 유도체 및 이의 제조방법
WO2017137955A1 (en) 2016-02-14 2017-08-17 Celestis Pharmaceuticals Pvt. Ltd. Novel (r) and rac 3-(2-(allyloxy)-5-methylphenyl)-n,n-diisopropyl-3- phenylpropan-1-amine and its use for synthesis of (r) and rac-2-(3- (diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol
WO2018013739A2 (en) * 2016-07-12 2018-01-18 Chromocell Corporation Compounds, compositions, and methods for modulating sweet taste
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ZA969363B (en) 1995-11-08 1997-11-18 Smithkline Beecham Corp An improved process for preparing aromatic ring-fused cyclopentane derivatives.
KR20000057548A (ko) 1996-12-13 2000-09-25 알프레드 엘. 미첼슨 광학적 전송물질 및 결합재
EP0957073A1 (en) * 1998-05-12 1999-11-17 Schwarz Pharma Ag Novel derivatives of 3,3-diphenylpropylamines

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Publication number Publication date
DE60015799T2 (de) 2005-12-15
CN1209342C (zh) 2005-07-06
MY118906A (en) 2005-02-28
JP2003519207A (ja) 2003-06-17
WO2001049649A1 (en) 2001-07-12
PL355947A1 (en) 2004-05-31
NO20023189L (no) 2002-07-04
ZA200204066B (en) 2003-07-30
EP1242361B1 (en) 2004-11-10
AU782796B2 (en) 2005-09-01
NZ519079A (en) 2004-02-27
BR0016785A (pt) 2002-09-24
DK1242361T3 (da) 2005-02-14
DE60015799D1 (de) 2004-12-16
HUP0203816A3 (en) 2004-12-28
SK9392002A3 (en) 2003-01-09
US20010016669A1 (en) 2001-08-23
EP1496045A2 (en) 2005-01-12
ES2228658T3 (es) 2005-04-16
CN1414944A (zh) 2003-04-30
IL150275A0 (en) 2002-12-01
NO20023189D0 (no) 2002-07-01
CA2392832A1 (en) 2001-07-12
MXPA02006415A (es) 2002-11-29
KR20020062669A (ko) 2002-07-26
PE20011123A1 (es) 2001-11-09
SE9904850D0 (sv) 1999-12-30
EP1496045A3 (en) 2005-03-30
HK1052000A1 (en) 2003-08-29
EP1242361A1 (en) 2002-09-25
US6310248B2 (en) 2001-10-30
PT1242361E (pt) 2005-01-31
EE200200325A (et) 2003-08-15
ATE282019T1 (de) 2004-11-15
AU2719001A (en) 2001-07-16
CZ20022255A3 (cs) 2002-11-13
AR027138A1 (es) 2003-03-12
HUP0203816A2 (hu) 2003-03-28

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