CA2557391C - Process for the preparation of tryptase inhibitors - Google Patents

Process for the preparation of tryptase inhibitors Download PDF

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Publication number
CA2557391C
CA2557391C CA2557391A CA2557391A CA2557391C CA 2557391 C CA2557391 C CA 2557391C CA 2557391 A CA2557391 A CA 2557391A CA 2557391 A CA2557391 A CA 2557391A CA 2557391 C CA2557391 C CA 2557391C
Authority
CA
Canada
Prior art keywords
formula
salt
amino
compound
tert
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
CA2557391A
Other languages
English (en)
French (fr)
Other versions
CA2557391A1 (en
Inventor
Claus-Dieter Graf
Christoph Tappertzhofen
Adam W. Sledeski
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.)
Aventis Pharmaceuticals Inc
Original Assignee
Aventis Pharmaceuticals 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 Aventis Pharmaceuticals Inc filed Critical Aventis Pharmaceuticals Inc
Publication of CA2557391A1 publication Critical patent/CA2557391A1/en
Application granted granted Critical
Publication of CA2557391C publication Critical patent/CA2557391C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C07D211/26—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 nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
    • 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
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent 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
    • C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
    • 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
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2557391A 2004-03-02 2005-02-18 Process for the preparation of tryptase inhibitors Expired - Fee Related CA2557391C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP04004799A EP1571150A1 (en) 2004-03-02 2004-03-02 Process for the preparation of tryptase inhibitors
EP04004799.5 2004-03-02
US58574504P 2004-07-06 2004-07-06
US60/585,745 2004-07-06
PCT/EP2005/001676 WO2005095385A1 (en) 2004-03-02 2005-02-18 Process for the preparation of tryptase inhibitors

Publications (2)

Publication Number Publication Date
CA2557391A1 CA2557391A1 (en) 2005-10-13
CA2557391C true CA2557391C (en) 2011-06-28

Family

ID=34745976

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2557391A Expired - Fee Related CA2557391C (en) 2004-03-02 2005-02-18 Process for the preparation of tryptase inhibitors

Country Status (19)

Country Link
US (1) US20130225825A1 (enExample)
EP (2) EP1571150A1 (enExample)
JP (1) JP4851440B2 (enExample)
CN (2) CN1950362B (enExample)
AT (1) ATE447567T1 (enExample)
AU (1) AU2005229319B2 (enExample)
BR (1) BRPI0508430A (enExample)
CA (1) CA2557391C (enExample)
DK (1) DK1723140T3 (enExample)
ES (1) ES2334245T3 (enExample)
NZ (1) NZ549224A (enExample)
PL (1) PL1723140T3 (enExample)
PT (1) PT1723140E (enExample)
RS (1) RS51144B (enExample)
RU (1) RU2378271C2 (enExample)
SI (1) SI1723140T1 (enExample)
TN (1) TNSN06260A1 (enExample)
UA (1) UA85701C2 (enExample)
WO (1) WO2005095385A1 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200840566A (en) * 2006-12-22 2008-10-16 Esteve Labor Dr Heterocyclyl-substituted-ethylamino-phenyl derivatives, their preparation and use as medicaments
US8158792B2 (en) 2007-11-21 2012-04-17 Janssen Pharmaceutica N.V. Spiropiperidines for use as tryptase inhibitors
CA2734877C (en) * 2008-08-22 2014-04-29 Sanofi-Aventis [4-(5-aminomethyl-2-fluoro-phenyl)-piperidin-1-yl]-[7-fluoro-1-(2-methoxy-ethyl)-4-trifluoromethoxy-1h-indol-3-yl]-methanone as an inhibitor of mast cell tryptase
JP2013505935A (ja) * 2009-09-24 2013-02-21 サノフィ−アベンティス・ユー・エス・エルエルシー （４−フルオロ−３−ピペリジン−４−イル−ベンジル）−カルバミン酸ｔｅｒｔ−ブチルエステルの合成及びその中間体
MX2012006741A (es) * 2009-12-23 2012-07-04 Sanofi Sa Tratamiento para la enfermedad inflamatoria del intestino.
BR112013032813A2 (pt) 2011-06-20 2016-08-16 Du Pont composto de fórmula, composição e método para o tratamento, controle, prevenção ou proteção dos animais contra a infecção por helmintos
AU2012346433A1 (en) 2011-11-28 2014-05-08 E. I. Du Pont De Nemours And Company N- (4 -quinolinylmethyl) sulfonamide derivatives and their use as anthelmintics
WO2014099837A1 (en) 2012-12-18 2014-06-26 E. I. Du Pont De Nemours And Company Sulfonamide anthelmintics
CN111793101B (zh) * 2020-07-17 2022-09-30 四川大学 C-核苷化合物的合成方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0401166B1 (de) * 1989-06-01 1995-02-22 Ciba-Geigy Ag Neue, stickstoffhaltige Titanocene und deren Verwendung
US5252753A (en) * 1991-11-01 1993-10-12 Ortho Pharmaceutical Corporation Process for the preparation of certain substituted biphenyl tetrazoles and compounds thereof
ZA979781B (en) * 1996-11-14 1998-06-08 Akzo Nobel Nv Piperidine derivatives.
WO1999018053A1 (en) * 1997-10-02 1999-04-15 The University Of Western Ontario Preparation of radiolabelled haloaromatics via polymer-bound intermediates
US20020045613A1 (en) * 2000-04-27 2002-04-18 Heinz Pauls 1-aroyl-piperidinyl benzamidines
AR033525A1 (es) * 2000-05-22 2003-12-26 Aventis Pharma Ltd Arilmetilaminas sustituidas, composiciones farmaceuticas, uso de las mismas para la manufactura de un medicamento
WO2004035744A2 (en) * 2002-10-18 2004-04-29 Biostream, Inc. Methods for purifying radiolabelled compounds
GB0308613D0 (en) * 2002-12-26 2003-05-21 Aventis Pharma Inc 4-(3-Aminomethylphenyl) piperidin-1-yl- 5-(2-fluorophenylethynyl) furan-2-yl- methanone as an inhibitor of mast cell tryptase

Also Published As

Publication number Publication date
NZ549224A (en) 2010-10-29
CA2557391A1 (en) 2005-10-13
ATE447567T1 (de) 2009-11-15
DK1723140T3 (da) 2010-03-22
RU2378271C2 (ru) 2010-01-10
US20130225825A1 (en) 2013-08-29
EP1571150A1 (en) 2005-09-07
CN1950362B (zh) 2010-08-04
EP1723140B1 (en) 2009-11-04
RU2006134623A (ru) 2008-04-10
UA85701C2 (ru) 2009-02-25
TNSN06260A1 (en) 2007-12-03
PL1723140T3 (pl) 2010-02-26
SI1723140T1 (sl) 2010-02-26
CN1950362A (zh) 2007-04-18
RS51144B (sr) 2010-10-31
JP2007526264A (ja) 2007-09-13
AU2005229319B2 (en) 2011-10-20
PT1723140E (pt) 2010-01-13
WO2005095385A1 (en) 2005-10-13
BRPI0508430A (pt) 2007-07-24
ES2334245T3 (es) 2010-03-08
AU2005229319A1 (en) 2005-10-13
CN101429194A (zh) 2009-05-13
EP1723140A1 (en) 2006-11-22
JP4851440B2 (ja) 2012-01-11
CN101429194B (zh) 2011-12-14

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EEER Examination request
MKLA Lapsed

Effective date: 20160218