WO2006064351A3 - N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors - Google Patents

N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors Download PDF

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Publication number
WO2006064351A3
WO2006064351A3 PCT/IB2005/003791 IB2005003791W WO2006064351A3 WO 2006064351 A3 WO2006064351 A3 WO 2006064351A3 IB 2005003791 W IB2005003791 W IB 2005003791W WO 2006064351 A3 WO2006064351 A3 WO 2006064351A3
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WO
WIPO (PCT)
Prior art keywords
aryl
4alkyl
6alkyl
aromatic
alkyl
Prior art date
Application number
PCT/IB2005/003791
Other languages
French (fr)
Other versions
WO2006064351A2 (en
Inventor
Mark David Andrews
Alan Daniel Brown
Paul Vincent Fish
Michael Jonathan Fray
Mark Ian Lansdell
Thomas Ryckmans
Alan Stobie
Florian Vakenhut
David Lawrence Firman Gray
Original Assignee
Pfizer Ltd
Mark David Andrews
Alan Daniel Brown
Paul Vincent Fish
Michael Jonathan Fray
Mark Ian Lansdell
Thomas Ryckmans
Alan Stobie
Florian Vakenhut
David Lawrence Firman Gray
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 GB0427618A external-priority patent/GB0427618D0/en
Application filed by Pfizer Ltd, Mark David Andrews, Alan Daniel Brown, Paul Vincent Fish, Michael Jonathan Fray, Mark Ian Lansdell, Thomas Ryckmans, Alan Stobie, Florian Vakenhut, David Lawrence Firman Gray filed Critical Pfizer Ltd
Priority to JP2007546219A priority Critical patent/JP2008524200A/en
Priority to EP05811385A priority patent/EP1828122A2/en
Priority to CA002591415A priority patent/CA2591415A1/en
Publication of WO2006064351A2 publication Critical patent/WO2006064351A2/en
Publication of WO2006064351A3 publication Critical patent/WO2006064351A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/24—Antidepressants
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Reproductive Health (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • Psychiatry (AREA)
  • Endocrinology (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

A compound of Formula (I) and pharmaceutically and/or veterinarily acceptable derivatives thereof, wherein: R1 is H, C1-6alkyl, -C(A)Y, C3-8cycloalkyl, aryl, het, aryl-C1-4alkyl or het-Cl-4alkyl, wherein the cycloalkyl, aryl or het groups are optionally substituted; A is S or O; Y is H, C1-6alkyl, aryl, het, aryl-C1-4alkyl or het­-C1-4alkyl; aryl is independently selected from phenyl, naphthyl, anthracyl or phenanthryl; het is independently selected from an aromatic or non-aromatic 4-, 5- or 6- membered heterocycle which contains at least one N, O or S heteroatom, optionally fused to a 5- or 6- membered carbocyclic group or a second 4-, 5- or 6-membered heterocycle which contains at least one N, O or S heteroatom; R2 is aryl1 or het1, each optionally substituted; aryl1 is independently selected from phenyl, naphthyl, anthracyl, phenanthryl, or indanyl; het1 is an aromatic 5 to 10 membered heterocyclic ring system which contains at least one N, O or S heteroatom, optionally containing an aryl group; R3 is H, C1-8alkyl, C3-8cycloalkyl, C3-8cycloalkyl-C1-6alkyl, C1-8alkylSC1-8alkyl, het3, or het3-C1-4alkyl, wherein the alkyl, cycloalkyl and het3 groups are each optionally substituted; het3 is a non-aromatic 4-, 5- or 6- membered heterocycle which contains at least one N, O or S heteroatom, optionally fused to a 5- or 6- membered carbocyclic group or a second 4-, 5- or 6-membered heterocycle which contains at least one N, O or S heteroatom; or R3 is (CH2)a,K, wherein a' is 0, 1 or 2 and K is a group selected from: Formula (i) wherein: Z is O, S, NR12, (CH2)V or a bond; a is 1, 2, 3 or 4; b is 1, 2 or 3; v is 1 or 2; R10 and R11 are each independently H or C1-4 alkyl; R12 is H, C1-6 alkyl, C(O)C1-6 alkyl, SO2-C1-6 alkyl; and wherein one or more pairs of hydrogen atoms on adjacent carbon or nitrogen atoms may be replaced by a corresponding number of double bonds, provided the ring system is not aromatic; Formula (ii) a carbocyclic spiro group containing 6 to 12 carbon atoms; Formula(iii) wherein: c is 1, 2, 3 or 4; d is 1, 2 or 3; e is 1 or 2; and R30 is H or C1-4 alkyl; and wherein one or more pairs of hydrogen atoms on adjacent carbon atoms may be replaced by a corresponding number of double bonds, provided the ring system is not aromatic; Formula (iv) wherein: f is 0, 1, 2 or 3; L is SO, SO2 or NR40; and R40 is H, C1-6 alkyl, C(O)C1-6alkyl, SO2-C1-6alkyl; and wherein one or more pairs of hydrogen atoms on adjacent carbon atoms may be replaced by a corresponding number of double bonds, provided the ring system is not aromatic; Formula (v) wherein: g is 0, 1, 2 or 3; and R50 is H, C1-8alkyl, C1-8alkoxy, OH, halo, CF3, OCHF2, OCF3, SCF3, hydroxy-C1-6alkyl, C1-4alkoxy-C1-6alkyl and C1-4alkyl-S-C1-4alkyl; and Formula (vi) CH(cyclopropane)2; X is a covalent bond, C1-8alkyl or C3-8cycloalkyl, wherein if X is C3-8cycloalkyl, then R2-X may form a fused aryl-cycloalkyl ring system; and n is 1 or 2, provided that when n is 1, m is 0 or 1 and when n is 2, m is 0, wherein if m is 0, then * represents a chiral centre.
PCT/IB2005/003791 2004-12-16 2005-12-08 N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors WO2006064351A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2007546219A JP2008524200A (en) 2004-12-16 2005-12-08 New compounds
EP05811385A EP1828122A2 (en) 2004-12-16 2005-12-08 N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors
CA002591415A CA2591415A1 (en) 2004-12-16 2005-12-08 N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
GB0427618.4 2004-12-16
GB0427618A GB0427618D0 (en) 2004-12-16 2004-12-16 Novel compounds
US64783905P 2005-01-27 2005-01-27
US60/647,839 2005-01-27
US69523805P 2005-06-28 2005-06-28
US60/695,238 2005-06-28

Publications (2)

Publication Number Publication Date
WO2006064351A2 WO2006064351A2 (en) 2006-06-22
WO2006064351A3 true WO2006064351A3 (en) 2006-10-12

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2005/003791 WO2006064351A2 (en) 2004-12-16 2005-12-08 N-pyrrolidin-3-yl-amide derivatives as serotonin and noradrenalin re-uptake inhibitors

Country Status (4)

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EP (1) EP1828122A2 (en)
JP (1) JP2008524200A (en)
CA (1) CA2591415A1 (en)
WO (1) WO2006064351A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2008029924A1 (en) 2006-09-08 2010-01-21 大日本住友製薬株式会社 Cyclic aminoalkylcarboxamide derivatives
US8173666B2 (en) 2007-03-12 2012-05-08 Nektar Therapeutics Oligomer-opioid agonist conjugates
US10512644B2 (en) 2007-03-12 2019-12-24 Inheris Pharmaceuticals, Inc. Oligomer-opioid agonist conjugates
JP2011102241A (en) * 2008-03-04 2011-05-26 Dainippon Sumitomo Pharma Co Ltd Novel 1-aminocarbonylpiperidine derivative

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3577440A (en) * 1968-12-23 1971-05-04 Robins Co Inc A H 1-substituted-3-amido-pyrrolidines
US3963745A (en) * 1972-04-03 1976-06-15 A. H. Robins Company, Incorporated Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides
FR2295744A1 (en) * 1974-12-26 1976-07-23 Robins Co Inc A H N- (PYRROLIDINYL-3 1-SUBSTITUTE) NAPHTALENECARBOXAMIDES-1 AND QUINOLEINE-CARBOXAMIDES-4 AND PROCESS FOR THEIR PREPARATION
EP1125922A1 (en) * 1998-11-02 2001-08-22 Welfide Corporation Pyrrolidine compounds and medicinal utilization thereof
WO2004000808A2 (en) * 2002-06-24 2003-12-31 Acadia Pharmaceuticals Inc. N-substituted piperidine derivatives as serotonin receptor agents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3577440A (en) * 1968-12-23 1971-05-04 Robins Co Inc A H 1-substituted-3-amido-pyrrolidines
US3963745A (en) * 1972-04-03 1976-06-15 A. H. Robins Company, Incorporated Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides
FR2295744A1 (en) * 1974-12-26 1976-07-23 Robins Co Inc A H N- (PYRROLIDINYL-3 1-SUBSTITUTE) NAPHTALENECARBOXAMIDES-1 AND QUINOLEINE-CARBOXAMIDES-4 AND PROCESS FOR THEIR PREPARATION
EP1125922A1 (en) * 1998-11-02 2001-08-22 Welfide Corporation Pyrrolidine compounds and medicinal utilization thereof
WO2004000808A2 (en) * 2002-06-24 2003-12-31 Acadia Pharmaceuticals Inc. N-substituted piperidine derivatives as serotonin receptor agents

Also Published As

Publication number Publication date
EP1828122A2 (en) 2007-09-05
CA2591415A1 (en) 2006-06-22
WO2006064351A2 (en) 2006-06-22
JP2008524200A (en) 2008-07-10

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