WO2010106269A3 - Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics - Google Patents

Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics Download PDF

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Publication number
WO2010106269A3
WO2010106269A3 PCT/FR2010/050447 FR2010050447W WO2010106269A3 WO 2010106269 A3 WO2010106269 A3 WO 2010106269A3 FR 2010050447 W FR2010050447 W FR 2010050447W WO 2010106269 A3 WO2010106269 A3 WO 2010106269A3
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alkyl
cycloalkyl
groups
therapeutics
halo
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PCT/FR2010/050447
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French (fr)
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WO2010106269A2 (en
Inventor
Geneviève ESTENNE-BOUHTOU
Abdel-Kader Mafroud
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Sanofi-Aventis
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Priority claimed from FR0901219A external-priority patent/FR2943056A1/en
Priority claimed from FR0901810A external-priority patent/FR2944283B1/en
Priority to RU2011141778/04A priority Critical patent/RU2011141778A/en
Priority to CN2010800121453A priority patent/CN102356074A/en
Priority to CA2755526A priority patent/CA2755526A1/en
Priority to MX2011009677A priority patent/MX2011009677A/en
Application filed by Sanofi-Aventis filed Critical Sanofi-Aventis
Priority to AU2010224720A priority patent/AU2010224720A1/en
Priority to JP2012500292A priority patent/JP2012520345A/en
Priority to SG2011066867A priority patent/SG174434A1/en
Priority to BRPI1009496A priority patent/BRPI1009496A2/en
Priority to EP10715932A priority patent/EP2408763A2/en
Publication of WO2010106269A2 publication Critical patent/WO2010106269A2/en
Publication of WO2010106269A3 publication Critical patent/WO2010106269A3/en
Priority to IL215104A priority patent/IL215104A0/en

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    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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    • A61P25/04—Centrally acting analgesics, e.g. opioids
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    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
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    • 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
    • C07D213/46—Oxygen atoms
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    • 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
    • C07D213/60—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 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems

Abstract

The invention relates to compounds of general formula (I) wherein R is a hydrogen atom or a group selected from the groups (C1-C6) aIkyI, (C3-C7) cycloalkyl, benzyl or allyl optionally substituted by at least one group selected independently from each other from the halogen atoms, the groups (C3-C7) cycloalkyl, (C1-C6) alkyl, (C1-C6) BlCOXy, hydroxy; R1 is a phenyl or naphtyl group, optionally substituted by at least one substitutent selected independently from each other from the halogen atoms, the groups (CrC6) alkyl, (C1-C6) BlCOXy, halo-(C1-C6) alkyl, hydroxy, halo-(C1C6) alcoxy, (C1-C6) alkyl-thio, (C1-C6)alkyl-SO, (C1C6) alkyl-SO2; Het is a heteroaryl group; and R2 is at least one substituent selected from the hydrogen atom, the halogen atoms, the groups halo-(d-C6) alkyl, (C1C6) alkyl, (C3-C7) cycloalkyl, (C3-C7)-cycloalkyl-(C1-C3) alkyl, (C1- C6) alcoxy, benzyl, (C1C6) alkyl-thio, (C1C6) alkyl-SO, (C1C6) alkyl-SO2; in the base state or as addition salts for acids. The invention also relates to the use of said compounds in therapeutics and synthesis methods.
PCT/FR2010/050447 2009-03-16 2010-03-15 Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics WO2010106269A2 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
EP10715932A EP2408763A2 (en) 2009-03-16 2010-03-15 Derivatives of n-ý(2-aza-bicycloý2.1.1¨hex-1-yl)-aryl-methyl¨-heterobenzamide, preparation thereof and application of same in therapeutics
BRPI1009496A BRPI1009496A2 (en) 2009-03-16 2010-03-15 n - [(2-aza-bicyclo [2.1.1] hex-1-yl) arylmethyl] heterobenzamide derivatives, their preparation and their therapeutic application
CN2010800121453A CN102356074A (en) 2009-03-16 2010-03-15 Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics
CA2755526A CA2755526A1 (en) 2009-03-16 2010-03-15 Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics
MX2011009677A MX2011009677A (en) 2009-03-16 2010-03-15 Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-het erobenzamide, preparation thereof and application of same in therapeutics.
RU2011141778/04A RU2011141778A (en) 2009-03-16 2010-03-15 Derivatives of N - [(2-azabicyclo [2.1.1] HEX-1-IL) arylmethyl] heterobenzamide, their production and their use in therapy
AU2010224720A AU2010224720A1 (en) 2009-03-16 2010-03-15 Derivatives of N-[(2-aza-bicyclo [2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics
JP2012500292A JP2012520345A (en) 2009-03-16 2010-03-15 Derivatives of N-[(2-aza-bicyclo [2.1.1] hex-1-yl) -aryl-) methyl] -heterobenzamide, their preparation and their use in therapy
SG2011066867A SG174434A1 (en) 2009-03-16 2010-03-15 Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics
IL215104A IL215104A0 (en) 2009-03-16 2011-09-12 Derivatives of n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
FR0901219A FR2943056A1 (en) 2009-03-16 2009-03-16 New N-(2-aza-bicyclo(2.2.1)-hex-1-yl)-aryl-methyl-heterobenzamide derivatives are glycine transporter 1 inhibitors useful to treat e.g. dementia, psychosis, schizophrenia, anxiety, panic attacks, and obsessive compulsive disorder
FR09/01219 2009-03-16
FR0901810A FR2944283B1 (en) 2009-04-14 2009-04-14 N- (2-AZA-BICYCLO) -2.1.1-HEX-1-YL) -ARYL-METHYL-HETEROBENZAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC USE
FR09/01810 2009-04-14

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WO2010106269A2 WO2010106269A2 (en) 2010-09-23
WO2010106269A3 true WO2010106269A3 (en) 2010-12-02

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EP (1) EP2408763A2 (en)
JP (1) JP2012520345A (en)
KR (1) KR20110132565A (en)
CN (1) CN102356074A (en)
AR (1) AR075837A1 (en)
AU (1) AU2010224720A1 (en)
CA (1) CA2755526A1 (en)
IL (1) IL215104A0 (en)
MX (1) MX2011009677A (en)
RU (1) RU2011141778A (en)
SG (1) SG174434A1 (en)
TW (1) TW201036980A (en)
UY (1) UY32495A (en)
WO (1) WO2010106269A2 (en)

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Publication number Priority date Publication date Assignee Title
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WO2004013100A2 (en) * 2002-07-29 2004-02-12 Sanofi-Aventis N-[phenyl(piperidin-2-yl)methyl]benzamide derivatives, preparation thereof, and use thereof in therapy
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Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992012128A1 (en) * 1991-01-14 1992-07-23 The Du Pont Merck Pharmaceutical Company (amidomethyl)nitrogen heterocyclic analgesics
WO2004013100A2 (en) * 2002-07-29 2004-02-12 Sanofi-Aventis N-[phenyl(piperidin-2-yl)methyl]benzamide derivatives, preparation thereof, and use thereof in therapy
WO2004013101A2 (en) * 2002-07-29 2004-02-12 Sanofi-Aventis N-[phenyl(piperidin-2-yl)methyl]benzamide derivatives, preparation thereof, and use thereof in therapy
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WO2005037792A1 (en) * 2003-10-17 2005-04-28 Sanofi-Aventis Derivatives of n-``phenyl(piperidine-2-yl) methyl benzamide, preparation method thereof and applications of same in therapeutics
WO2005037783A2 (en) * 2003-10-17 2005-04-28 Sanofi-Aventis Use of tricyclic compounds as glycine transport inhibitors
WO2005037785A2 (en) * 2003-10-17 2005-04-28 Sanofi-Aventis Derivatives of n-[phenyl(pyrrolidine-2-yl)methyl]benzamide and n-[(azepan-2-yl)phenylmethyl]benzamide, preparation method thereof and application of same in therapeutics
WO2008018639A2 (en) * 2006-08-11 2008-02-14 Taisho Pharmaceutical Co., Ltd. Glycine transporter inhibitor
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