WO2006044454A1 - 1-(hetero)aryl-3-amino-pyrollidine derivatives for use as mglur3 receptor antagonists - Google Patents

1-(hetero)aryl-3-amino-pyrollidine derivatives for use as mglur3 receptor antagonists Download PDF

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Publication number
WO2006044454A1
WO2006044454A1 PCT/US2005/036665 US2005036665W WO2006044454A1 WO 2006044454 A1 WO2006044454 A1 WO 2006044454A1 US 2005036665 W US2005036665 W US 2005036665W WO 2006044454 A1 WO2006044454 A1 WO 2006044454A1
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WO
WIPO (PCT)
Prior art keywords
pyrrolidin
amine
compound
mmol
group
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.)
Ceased
Application number
PCT/US2005/036665
Other languages
English (en)
French (fr)
Inventor
Thomas Charles Britton
Veronique Dehlinger
Colin Peter Dell
Bruce Anthony Dressman
Jason Kenneth Myers
Eric Samuel NISENBAUM
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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 Eli Lilly and Co filed Critical Eli Lilly and Co
Priority to US11/576,960 priority Critical patent/US7868014B2/en
Priority to EP05804465A priority patent/EP1805165B1/en
Priority to DE602005018381T priority patent/DE602005018381D1/de
Priority to BRPI0516602-0A priority patent/BRPI0516602A/pt
Priority to AU2005295860A priority patent/AU2005295860A1/en
Priority to MX2007004661A priority patent/MX2007004661A/es
Priority to CA002584422A priority patent/CA2584422A1/en
Priority to AT05804465T priority patent/ATE452130T1/de
Priority to JP2007536836A priority patent/JP5188807B2/ja
Publication of WO2006044454A1 publication Critical patent/WO2006044454A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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]
    • 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
    • C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
    • 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
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • 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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • R 3 is selected from the group consisting of hydrogen and methyl
  • R 4 is selected from the group consisting of hydrogen, methyl, hydroxy, oxo, and fluoro
  • R 5 is selected from the group consisting of hydrogen and methyl
  • n is 1 or 2
  • m is 1 or 2
  • pharmaceutically acceptable salts thereof excluding the compounds (S)-ben2yl-[l-(5-trifluoromethylpyrid-2-yl)-pyrrolidin- 3-yl]-amine, 4-chloroben2yl-[l-quinol-2-yl- ⁇ yrrolidin-3-yl] -amine, A- bromobenzyl-[l -quinol-2-yl-pyrrolidin-3-yl] -amine, and 4-methylbenzyl-[l- quinol-2-yl-pyrrolidin-3-yl]-amine.
  • the present invention also provides pharmaceutical compositions, comprising: a compound of the formula I and a pharmaceutically acceptable
  • pharmaceutically acceptable salt refers to salts of pharmaceutically acceptable organic acids or inorganic acids. Such salts include those known to the skilled artisan, such as those described in Journal of Pharmaceutical Science, 66, 2-19 (1977). Examples of such pharmaceutically acceptable salts are the hydrochloride, fumarate, and mesylate salts.
  • R 2 is phenyl substitution with 1 to 3 substituents independently selected from the group consisting of alkyl, alkoxy, trifluoromethyl, halogen, cyano, and nitro are even more preferred.
  • R 2 is phenyl substitution with 1 to 2 substituents independently selected from the group consisting of trifluoromethyl and halogen are even more preferred.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
PCT/US2005/036665 2004-10-18 2005-10-13 1-(hetero)aryl-3-amino-pyrollidine derivatives for use as mglur3 receptor antagonists Ceased WO2006044454A1 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US11/576,960 US7868014B2 (en) 2004-10-18 2005-10-13 1-(hetero)aryl-3-amino-pyrrolidine derivatives for use as mGluR3 antagonists
EP05804465A EP1805165B1 (en) 2004-10-18 2005-10-13 1-(hetero)aryl-3-amino-pyrrolidine derivatives for use as mglur3 receptor antagonists
DE602005018381T DE602005018381D1 (de) 2004-10-18 2005-10-13 1-(hetero)aryl-3-aminopyrrolidinderivate zur verwendung als antagonisten des mglur3-rezeptors
BRPI0516602-0A BRPI0516602A (pt) 2004-10-18 2005-10-13 composto, e, composição farmacêutica
AU2005295860A AU2005295860A1 (en) 2004-10-18 2005-10-13 1-(hetero)aryl-3-amino-pyrollidine derivatives for use as mGluR3 receptor antagonists
MX2007004661A MX2007004661A (es) 2004-10-18 2005-10-13 Derivados de 1-(hetero)aril-3-amino-pirrolidina para usarse como antagonistas del receptor mglur3.
CA002584422A CA2584422A1 (en) 2004-10-18 2005-10-13 1-(hetero)aryl-3-amino-pyrollidine derivatives for use as mglur3 receptor antagonists
AT05804465T ATE452130T1 (de) 2004-10-18 2005-10-13 1-(hetero)aryl-3-aminopyrrolidinderivate zur verwendung als antagonisten des mglur3-rezeptors
JP2007536836A JP5188807B2 (ja) 2004-10-18 2005-10-13 ｍＧｌｕＲ３受容体アンタゴニストとして用いるための１−（ヘテロ）アリール−３−アミノ−ピロリジン誘導体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61978904P 2004-10-18 2004-10-18
US60/619,789 2004-10-18

Publications (1)

Publication Number Publication Date
WO2006044454A1 true WO2006044454A1 (en) 2006-04-27

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/036665 Ceased WO2006044454A1 (en) 2004-10-18 2005-10-13 1-(hetero)aryl-3-amino-pyrollidine derivatives for use as mglur3 receptor antagonists

Country Status (12)

Country Link
US (1) US7868014B2 (https=)
EP (1) EP1805165B1 (https=)
JP (1) JP5188807B2 (https=)
CN (1) CN101094846A (https=)
AT (1) ATE452130T1 (https=)
AU (1) AU2005295860A1 (https=)
BR (1) BRPI0516602A (https=)
CA (1) CA2584422A1 (https=)
DE (1) DE602005018381D1 (https=)
ES (1) ES2336130T3 (https=)
MX (1) MX2007004661A (https=)
WO (1) WO2006044454A1 (https=)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009131196A1 (ja) * 2008-04-24 2009-10-29 武田薬品工業株式会社 置換ピロリジン誘導体およびその用途
US7713965B2 (en) 2008-02-29 2010-05-11 Vetoquinol Sa 7-substituted 3-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials
EP1757582A4 (en) * 2004-05-28 2010-05-12 Mitsubishi Tanabe Pharma Corp ARYL ALKYLAMINES AND METHOD FOR THE PRODUCTION THEREOF
US8071590B2 (en) 2008-07-09 2011-12-06 Vetoquinol Sa 9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials
US10154988B2 (en) 2012-11-14 2018-12-18 The Johns Hopkins University Methods and compositions for treating schizophrenia
US10590131B2 (en) 2014-12-11 2020-03-17 Janssen Pharmaceutica Nv 1,2,4-triazolo[4,3-a]pyridine compounds and their use as positive allosteric modulators of mGluR2 receptors

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201022233A (en) * 2008-11-04 2010-06-16 Organon Nv (Pyrrolidin-2-yl)phenyl derivatives
CN113024412A (zh) * 2021-03-23 2021-06-25 上海立科化学科技有限公司 2,4,6-三氯苯腈的制备方法
CN114149297A (zh) * 2021-12-07 2022-03-08 北京中医药大学 一种微波辅助的选择性芳基甲醛的绿色合成方法
CN115368283A (zh) * 2022-09-15 2022-11-22 丽水绿氟科技有限公司 一种手性结构或非手性结构的顺式-3-氟-4-羟基吡咯烷及其衍生物的制备方法

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Cited By (14)

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Publication number Priority date Publication date Assignee Title
US8492111B2 (en) 2004-05-28 2013-07-23 Mitsubishi Tanabe Pharma Corporation Arylalkylamine compound and process for preparing the same
EP1757582A4 (en) * 2004-05-28 2010-05-12 Mitsubishi Tanabe Pharma Corp ARYL ALKYLAMINES AND METHOD FOR THE PRODUCTION THEREOF
US20110218160A1 (en) * 2004-05-28 2011-09-08 Hiroshi Miyazaki Arylalkylamine compound and process for preparing the same
US8362274B2 (en) 2004-05-28 2013-01-29 Mitsubishi Tanabe Pharma Corporation Arylalkylamine compound and process for preparing the same
US8759387B2 (en) 2004-05-28 2014-06-24 Mitsubishi Tanabe Pharma Corporation Arylalkylamine compound and process for preparing the same
US8703721B2 (en) 2004-05-28 2014-04-22 Mitsubishi Tanabe Pharma Corporation Arylalkylamine compound and process for preparing the same
US8778628B2 (en) 2004-05-28 2014-07-15 Mitsubishi Tanabe Pharma Corporation Arylalkylamine compound and process for preparing the same
US7713965B2 (en) 2008-02-29 2010-05-11 Vetoquinol Sa 7-substituted 3-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials
WO2009131196A1 (ja) * 2008-04-24 2009-10-29 武田薬品工業株式会社 置換ピロリジン誘導体およびその用途
US8071590B2 (en) 2008-07-09 2011-12-06 Vetoquinol Sa 9-substituted-5-carboxy-oxadiazino-quinolone derivatives, their preparation and their application as anti-bacterials
US10154988B2 (en) 2012-11-14 2018-12-18 The Johns Hopkins University Methods and compositions for treating schizophrenia
EP3610890A1 (en) 2012-11-14 2020-02-19 The Johns Hopkins University Methods and compositions for treating schizophrenia
US10624875B2 (en) 2012-11-14 2020-04-21 The Johns Hopkins University Methods and compositions for treating schizophrenia
US10590131B2 (en) 2014-12-11 2020-03-17 Janssen Pharmaceutica Nv 1,2,4-triazolo[4,3-a]pyridine compounds and their use as positive allosteric modulators of mGluR2 receptors

Also Published As

Publication number Publication date
CN101094846A (zh) 2007-12-26
AU2005295860A1 (en) 2006-04-27
US20080300266A1 (en) 2008-12-04
JP5188807B2 (ja) 2013-04-24
JP2008516959A (ja) 2008-05-22
EP1805165A1 (en) 2007-07-11
DE602005018381D1 (de) 2010-01-28
ES2336130T3 (es) 2010-04-08
EP1805165B1 (en) 2009-12-16
ATE452130T1 (de) 2010-01-15
CA2584422A1 (en) 2006-04-27
US7868014B2 (en) 2011-01-11
BRPI0516602A (pt) 2008-09-16
MX2007004661A (es) 2007-06-22

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