CN103209954B - 作为mGluR2/3拮抗剂的4-取代的-3-苄氧基-双环[3.1.0]己烷化合物 - Google Patents

作为mGluR2/3拮抗剂的4-取代的-3-苄氧基-双环[3.1.0]己烷化合物 Download PDF

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Publication number
CN103209954B
CN103209954B CN201180055254.8A CN201180055254A CN103209954B CN 103209954 B CN103209954 B CN 103209954B CN 201180055254 A CN201180055254 A CN 201180055254A CN 103209954 B CN103209954 B CN 103209954B
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compound
tert
hexane
amino
mmol
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CN103209954A (zh
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B.A.德雷斯曼
M.D.查佩尔
A.M.费武什
C.H.米奇
P.L.奥尔恩斯泰因
E.G.特罗米查克
T.N.维特曼
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Eli Lilly and Co
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/36—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A—HUMAN NECESSITIES
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    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
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    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • A—HUMAN NECESSITIES
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    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4196—1,2,4-Triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C229/50—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/14—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C62/30—Unsaturated compounds
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
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    • C07—ORGANIC CHEMISTRY
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    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CN201180055254.8A 2010-11-18 2011-11-15 作为mGluR2/3拮抗剂的4-取代的-3-苄氧基-双环[3.1.0]己烷化合物 Active CN103209954B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US41511310P 2010-11-18 2010-11-18
US61/415113 2010-11-18
PCT/US2011/060686 WO2012068041A1 (en) 2010-11-18 2011-11-15 4-SUBSTITUTED-3-BENZYLOXY-BICYCLO[3.1.0]HEXANE COMPOUNDS AS mGluR 2/3 ANTAGONISTS

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Publication Number Publication Date
CN103209954A CN103209954A (zh) 2013-07-17
CN103209954B true CN103209954B (zh) 2015-09-02

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US (1) US9056844B2 (enExample)
EP (1) EP2640687B1 (enExample)
JP (1) JP5870111B2 (enExample)
KR (1) KR101554793B1 (enExample)
CN (1) CN103209954B (enExample)
AU (1) AU2011329136B2 (enExample)
BR (1) BR112013012384A2 (enExample)
CA (1) CA2818118C (enExample)
EA (1) EA022196B1 (enExample)
ES (1) ES2682959T3 (enExample)
MX (1) MX2013005623A (enExample)
WO (1) WO2012068041A1 (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR079343A1 (es) * 2009-12-21 2012-01-18 Lilly Co Eli Compuesto de acido 2-amino-4-(4h-1,2,4-triazol-3-ilsulfanil)biciclo[3.1.0]hexano-2,6-dicarboxilico, composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para tratar un trastorno psiquiatrico
EP3000814A1 (en) 2014-09-26 2016-03-30 Domain Therapeutics Substituted pyrazoloquinazolinones and pyrroloquinazolinones as allosteric modulators of group II metabotropic glutamate receptors
AU2017254266B2 (en) * 2016-04-18 2021-03-11 Taisho Pharmaceutical Co., Ltd. Prodrug of amino acid derivative
KR102549584B1 (ko) * 2018-03-27 2023-06-30 삼성전자주식회사 메모리 모듈을 포함하는 메모리 시스템, 메모리 모듈, 그리고 메모리 모듈의 동작 방법

Citations (5)

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Publication number Priority date Publication date Assignee Title
WO2000004010A1 (en) * 1998-07-17 2000-01-27 Eli Lilly And Company Limited Bicyclohexane derivatives
US6107342A (en) * 1998-09-03 2000-08-22 Hoffmann-La Roche Inc. 2-amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives and a process for the preparation thereof
JP2006193507A (ja) * 2004-12-15 2006-07-27 Taisho Pharmaceut Co Ltd うつ病の予防・治療薬
CN1812960A (zh) * 2003-06-26 2006-08-02 大正制药株式会社 2－氨基－双环[3.1.0]己烷－2,6－二甲酸酯衍生物
EP1897550A2 (en) * 2002-06-11 2008-03-12 Eli Lilly & Company Prodrugs of Excitatory Amino Acids

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JP2589812B2 (ja) 1989-07-05 1997-03-12 松下電器産業株式会社 スチームアイロン
ZA969485B (en) 1995-11-16 1998-05-12 Lilly Co Eli Excitatory amino acid receptor antagonists.
JP2000500752A (ja) 1995-11-16 2000-01-25 イーライ・リリー・アンド・カンパニー 興奮性アミノ酸受容体アンタゴニスト
ZA983930B (en) * 1997-05-14 1999-11-08 Lilly Co Eli Excitatory amino acid receptor modulators.
DE69919142T2 (de) 1998-03-17 2005-01-20 Pfizer Products Inc., Groton Bicyclo [2.2.1] heptane und verwandte verbindungen
EP1370519A1 (en) * 2001-02-22 2003-12-17 Eli Lilly And Company Synthetic excitatory amino acids
RU2315622C2 (ru) 2001-12-27 2008-01-27 Тайсо Фармасьютикал Ко.,Лтд. Производные 6-фторбицикло[3.1.0]гексана
US7381746B2 (en) 2003-06-26 2008-06-03 Taisho Pharmaceutical Co., Ltd. 2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivative
JP2007063129A (ja) 2003-06-26 2007-03-15 Taisho Pharmaceut Co Ltd ２−アミノ−３−アルコキシビシクロ［３．１．０］ヘキサン誘導体
ATE487690T1 (de) * 2003-06-26 2010-11-15 Taisho Pharmaceutical Co Ltd 2-aminobicyclo 3.1.0 hexan-2,6- dicarbonsäureesterderivat
AR079343A1 (es) * 2009-12-21 2012-01-18 Lilly Co Eli Compuesto de acido 2-amino-4-(4h-1,2,4-triazol-3-ilsulfanil)biciclo[3.1.0]hexano-2,6-dicarboxilico, composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para tratar un trastorno psiquiatrico

Patent Citations (5)

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WO2000004010A1 (en) * 1998-07-17 2000-01-27 Eli Lilly And Company Limited Bicyclohexane derivatives
US6107342A (en) * 1998-09-03 2000-08-22 Hoffmann-La Roche Inc. 2-amino-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives and a process for the preparation thereof
EP1897550A2 (en) * 2002-06-11 2008-03-12 Eli Lilly & Company Prodrugs of Excitatory Amino Acids
CN1812960A (zh) * 2003-06-26 2006-08-02 大正制药株式会社 2－氨基－双环[3.1.0]己烷－2,6－二甲酸酯衍生物
JP2006193507A (ja) * 2004-12-15 2006-07-27 Taisho Pharmaceut Co Ltd うつ病の予防・治療薬

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Title
"Prodrugs of 3-(3,4-dichlorobenzyloxy)-2-amino-6-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (MGS0039): A potent and orally active group II mGluR antagonist with antidepressant-like potential";Akito Yasuhara等;《Bioorg. Med. Chem.》;20060615;第14卷(第12期);第4193-4207页 *
"Synthesis, in vitro pharmacology, and structure–activity relationships of 2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivatives as mGluR2 antagonists";Akito Yasuhara等;《Bioorg. Med. Chem.》;20060515;第14卷(第10期);第3405-3410页 *

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JP5870111B2 (ja) 2016-02-24
EP2640687A1 (en) 2013-09-25
ES2682959T3 (es) 2018-09-24
EA022196B1 (ru) 2015-11-30
CA2818118A1 (en) 2012-05-24
CN103209954A (zh) 2013-07-17
WO2012068041A1 (en) 2012-05-24
KR101554793B1 (ko) 2015-09-21
AU2011329136A1 (en) 2013-05-02
US20130237573A1 (en) 2013-09-12
AU2011329136B2 (en) 2014-11-06
EP2640687B1 (en) 2018-06-27
US9056844B2 (en) 2015-06-16
CA2818118C (en) 2016-03-29
MX2013005623A (es) 2013-07-05
JP2014505663A (ja) 2014-03-06
EA201390568A1 (ru) 2013-09-30
KR20130080858A (ko) 2013-07-15
BR112013012384A2 (pt) 2019-09-24

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