CA2059704C - [[2-(amino-3,4-dioxo-1-cyclobuten-1-yl)amino]alkyl]-acid derivatives - Google Patents

[[2-(amino-3,4-dioxo-1-cyclobuten-1-yl)amino]alkyl]-acid derivatives Download PDF

Info

Publication number
CA2059704C
CA2059704C CA002059704A CA2059704A CA2059704C CA 2059704 C CA2059704 C CA 2059704C CA 002059704 A CA002059704 A CA 002059704A CA 2059704 A CA2059704 A CA 2059704A CA 2059704 C CA2059704 C CA 2059704C
Authority
CA
Canada
Prior art keywords
dioxo
carbon atoms
amino
alkyl
compound
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
CA002059704A
Other languages
English (en)
French (fr)
Other versions
CA2059704A1 (en
Inventor
William A. Kinney
Deanna C. Garrison
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.)
Wyeth LLC
Original Assignee
American Home Products Corp
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 American Home Products Corp filed Critical American Home Products Corp
Publication of CA2059704A1 publication Critical patent/CA2059704A1/en
Application granted granted Critical
Publication of CA2059704C publication Critical patent/CA2059704C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • 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
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/28—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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3826—Acyclic unsaturated acids
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6509—Six-membered rings
    • C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
    • C07F9/650994—Six-membered rings having the nitrogen atoms in the positions 1 and 4 condensed with carbocyclic rings or carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (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)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Lubricants (AREA)
CA002059704A 1991-01-22 1992-01-20 [[2-(amino-3,4-dioxo-1-cyclobuten-1-yl)amino]alkyl]-acid derivatives Expired - Fee Related CA2059704C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US64415791A 1991-01-22 1991-01-22
US644,157 1991-01-22
US806,861 1991-12-17
US07/806,861 US5168103A (en) 1991-01-22 1991-12-17 [[2-(amino-3,4-dioxo-1-cyclobuten-1-yl) amino]alkyl]-acid derivatives

Publications (2)

Publication Number Publication Date
CA2059704A1 CA2059704A1 (en) 1992-07-23
CA2059704C true CA2059704C (en) 2002-07-16

Family

ID=27094416

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002059704A Expired - Fee Related CA2059704C (en) 1991-01-22 1992-01-20 [[2-(amino-3,4-dioxo-1-cyclobuten-1-yl)amino]alkyl]-acid derivatives

Country Status (23)

Country Link
US (2) US5168103A (enExample)
EP (1) EP0496561B1 (enExample)
JP (1) JP3167770B2 (enExample)
KR (1) KR100206055B1 (enExample)
AT (1) ATE119873T1 (enExample)
AU (1) AU639629B2 (enExample)
CA (1) CA2059704C (enExample)
CZ (1) CZ286407B6 (enExample)
DE (1) DE69201655T2 (enExample)
DK (1) DK0496561T3 (enExample)
ES (1) ES2071428T3 (enExample)
FI (1) FI105551B (enExample)
GR (1) GR3015456T3 (enExample)
HK (1) HK1005588A1 (enExample)
HU (2) HU215838B (enExample)
IE (1) IE65873B1 (enExample)
IL (1) IL100679A (enExample)
MX (1) MX9200240A (enExample)
NZ (1) NZ241330A (enExample)
RU (1) RU2039035C1 (enExample)
SK (1) SK280268B6 (enExample)
TW (1) TW211564B (enExample)
UA (1) UA27741C2 (enExample)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL110309A0 (en) * 1993-07-15 1994-10-21 Univ Kentucky Res Found A method of protecting against neuron loss
KR970002653B1 (ko) * 1993-12-16 1997-03-07 엘지전자 주식회사 냉장고
US5631401A (en) * 1994-02-09 1997-05-20 Abbott Laboratories Inhibitors of protein farnesyltransferase and squalene synthase
US5466712A (en) * 1994-11-04 1995-11-14 American Home Products Corporation Substituted n-aryl-1,2-diaminocyclobutene-3,4-diones
UA67725C2 (en) * 1996-06-03 2004-07-15 Cephalon Inc K-252a derivatives and a method for improvement of functioning and cell survival enhancement
US5780505A (en) * 1996-07-17 1998-07-14 American Home Products Corporation Substituted N-arylmethylamino derivatives of cyclobutene-3, 4-diones
US5846999A (en) * 1996-07-17 1998-12-08 American Home Products Corporation Substituted N-arylmethylamino derivatives of cyclobutene-3,4-diones
DE69717841T2 (de) * 1996-07-17 2003-05-28 Wyeth, Madison Substituierte n-arylmethylamino-cyclobuten-3,4-dion-derivate
US5763474A (en) * 1996-07-17 1998-06-09 American Home Products Corporation Substituted N-arylmethylamino derivatives of cyclobutene-3,4-diones
US5750574A (en) * 1996-07-17 1998-05-12 American Home Products Corporation Fluorinated N-arylmethylamino derivatives of cyclobutene-3,4-diones
US5840764A (en) * 1997-01-30 1998-11-24 American Home Products Corporation Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones
US5990307A (en) * 1997-08-01 1999-11-23 American Home Products Corporation Process for the preparation of [2-((8.9)-Dioxo-2,6-Diazabicyclo [5.2.0]-Non-1(7)-en-2yl) Ethyl]Phosphonic acid
BR9811807A (pt) * 1997-08-01 2000-08-15 American Home Prod Processo para a preparação de ácido [2-(8,9)-dioxo-2,6-diazabiciclo-[5.2.0]-non-1(7)-en-2-il)-etil] fosfÈnico
JPH1177971A (ja) * 1997-09-05 1999-03-23 Shinano Kenshi Co Ltd ブランケット胴及び該ブランケット胴を備えたオフセット印刷装置
AU765603C (en) 1998-04-14 2004-08-05 General Hospital Corporation, The Methods for treating neuropsychiatric disorders
US6376555B1 (en) 1998-12-04 2002-04-23 American Home Products Corporation 4-substituted-3-substituted-amino-cyclobut-3-ene-1,2-diones and analogs thereof as novel potassium channel openers
US6166050A (en) * 1998-12-14 2000-12-26 American Home Products Corporation 3,4-diamino-3-cyclobutene-1,2-dione derivatives which inhibit leukocyte adhesion mediated by VLA-4
US7205404B1 (en) * 1999-03-05 2007-04-17 Metabasis Therapeutics, Inc. Phosphorus-containing prodrugs
KR100565008B1 (ko) * 2000-02-01 2006-03-30 주식회사유한양행 4-하이드라지노-3-사이클로부텐-1,2-다이온 유도체 및이들의 제조 방법
KR100742086B1 (ko) * 2001-07-27 2007-07-23 주식회사유한양행 4-페닐-3-사이클로부텐-1,2-다이온 유도체 및 그의 제조방법
UA78529C2 (en) * 2001-10-10 2007-04-10 Wyeth Corp Derivatives of [[2-(amino-3,4-dioxo-1-cyclobutene-1-yl)amino]alkyl] acid for treating pain
AU2004229567A1 (en) * 2003-04-09 2004-10-28 Wyeth Pharmaceutical compositions for intranasal administration of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1 (7)-en-2-yl)alkyl] phosphonic acid and derivatives and methods of use thereof
WO2004092189A1 (en) * 2003-04-09 2004-10-28 Wyeth Derivatives of 2-(8,9-dioxo-2,6-diazabicyclo(5.2.0)non-1(7)-en-2-yl)alkyl phosphonic acid and their use as n-methyl-d-aspartate (nmda) recetor antagonists
US20050142192A1 (en) * 2003-10-15 2005-06-30 Wyeth Oral administration of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)alkyl] phosphonic acid and derivatives
TW200514775A (en) * 2003-10-22 2005-05-01 Wyeth Corp Methods for the preparation of {2-[(8,9)-dioxo-2,6-diaza-bicyclo[5.2.0]-non-1(7)-en-2-yl]ethyl} phosphonic acid and esters thereof
EP1742914A1 (en) * 2004-02-27 2007-01-17 Schering Corporation Cyclobutenedione groups-containing compounds as inhibitors of hepatitis c virus ns3 serine protease
US7635694B2 (en) 2004-02-27 2009-12-22 Schering Corporation Cyclobutenedione-containing compounds as inhibitors of hepatitis C virus NS3 serine protease
KR20070100233A (ko) * 2004-10-08 2007-10-10 와이어쓰 [2-(8,9-디옥소-2,6-디아자바이사이클로[5.2.0]논-1(7)-엔-2-일)알킬]포스폰산의 유도체 및 이의 제조 방법
US20090061024A1 (en) * 2007-08-27 2009-03-05 Wyeth Compositions and methods employing nmda antagonists for achieving an anesthetic-sparing effect
MX2011003015A (es) 2008-09-18 2011-11-18 Univ Northwestern Moduladores del receptor de n-metil-d-aspartato, y usos de los mismos.
BRPI1009900A2 (pt) 2009-03-19 2016-03-15 Wyeth Llc métodos para a preparação de ácido [2-(8,9-dioxo-2,6-diazabiciclo[5.2.0]non-1(7)-en-2-il)etil]fosfônico e seus precursores
US9737531B2 (en) 2012-07-12 2017-08-22 Glytech, Llc Composition and method for treatment of depression and psychosis in humans
WO2014120784A1 (en) 2013-01-29 2014-08-07 Naurex, Inc. Spiro-lactam nmda receptor modulators and uses thereof
SG11201505937SA (en) 2013-01-29 2015-09-29 Naurex Inc Spiro-lactam nmda receptor modulators and uses thereof
JP6419087B2 (ja) 2013-01-29 2018-11-07 アプティニックス インコーポレイテッド スピロラクタム系nmda受容体モジュレーターおよびその使用
CA2898861C (en) 2013-01-29 2021-07-20 Naurex, Inc. Spiro-lactam nmda receptor modulators and uses thereof
CN105308049A (zh) 2013-01-29 2016-02-03 阿普廷伊克斯股份有限公司 螺-内酰胺nmda受体调节剂及其用途
EP3623364A1 (en) 2014-02-13 2020-03-18 Ligand Pharmaceuticals, Inc. Prodrug compounds and their uses
CN106687118A (zh) 2014-07-02 2017-05-17 配体药物公司 前药化合物及其用途
PE20190174A1 (es) 2016-05-19 2019-02-01 Aptinyx Inc Moduladores del receptor espiro-lactama n-metil-d-aspartato y usos de los mismos
WO2017201285A1 (en) 2016-05-19 2017-11-23 Aptinyx Inc. Spiro-lactam nmda receptor modulators and uses thereof
JP2019527235A (ja) 2016-08-01 2019-09-26 アプティニックス インコーポレイテッド スピロ−ラクタム及びビス−スピロ−ラクタムnmda受容体修飾因子及びその使用
PE20190501A1 (es) 2016-08-01 2019-04-10 Aptinyx Inc Moduladores nmda espiro-lactam y metodos de uso de los mismos
EP3490992B1 (en) 2016-08-01 2023-03-22 Aptinyx Inc. Spiro-lactam nmda receptor modulators and uses thereof
CN109890825B (zh) 2016-08-01 2022-03-11 阿普廷伊克斯股份有限公司 螺-内酰胺nmda受体调节剂及其用途
CA3031534C (en) 2016-08-01 2023-10-17 Aptinyx Inc. Spiro-lactam nmda receptor modulators and uses thereof
CA3067162A1 (en) 2017-06-12 2018-12-20 Glytech Llc. Composition and method for treatment or depression and psychosis in humans
WO2019139919A1 (en) 2018-01-09 2019-07-18 Ligand Pharmaceuticals, Inc. Acetal compounds and therapeutic uses thereof
PE20210455A1 (es) 2018-01-31 2021-03-08 Aptinyx Inc Moduladores del receptor nmda espiro-lactama y usos de los mismos
US12012413B2 (en) 2019-11-11 2024-06-18 Tenacia Biotechnology (Hong Kong) Co., Limited Methods of treating painful diabetic peripheral neuropathy

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1518660A1 (de) * 1965-07-09 1969-08-14 Huels Chemische Werke Ag Verfahren zur Herstellung aminosubstituierter Dioxocyclobutene
GB1563090A (en) * 1975-07-31 1980-03-19 Smith Kline French Lab Cyclobutene-diones
US4390701A (en) * 1981-05-18 1983-06-28 Bristol-Myers Company 1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione
AU1956283A (en) * 1982-10-02 1984-04-05 Smith Kline & French Laboratories Limited 1-(3-(4-(substited aminomethyl)pyrid-2-yl-oxy)-prop-1-yl- amino) - 2-aminocyclobut-i-ene-3,4-diones
US4927970A (en) * 1987-05-14 1990-05-22 Bristol-Myers Company Substituted 3-cyclobutene-1,2-dione intermediates
US4902687A (en) * 1989-03-27 1990-02-20 Eli Lilly And Company Excitatory amino acid receptor antagonists

Also Published As

Publication number Publication date
IE65873B1 (en) 1995-11-29
HU9200192D0 (en) 1992-04-28
DK0496561T3 (da) 1995-05-22
JPH04321654A (ja) 1992-11-11
FI105551B (fi) 2000-09-15
HU215838B (hu) 2000-06-28
IE920176A1 (en) 1992-07-29
AU639629B2 (en) 1993-07-29
EP0496561A2 (en) 1992-07-29
EP0496561B1 (en) 1995-03-15
NZ241330A (en) 1993-10-26
TW211564B (enExample) 1993-08-21
SK280268B6 (sk) 1999-10-08
AU1030192A (en) 1992-07-30
MX9200240A (es) 1994-03-31
JP3167770B2 (ja) 2001-05-21
HK1005588A1 (en) 1999-01-15
ATE119873T1 (de) 1995-04-15
EP0496561A3 (en) 1992-12-23
DE69201655D1 (de) 1995-04-20
KR920014765A (ko) 1992-08-25
CZ286407B6 (en) 2000-04-12
HU211653A9 (en) 1995-12-28
GR3015456T3 (en) 1995-06-30
KR100206055B1 (ko) 1999-07-01
US5168103A (en) 1992-12-01
FI920261L (fi) 1992-08-23
US5240946A (en) 1993-08-31
CA2059704A1 (en) 1992-07-23
UA27741C2 (uk) 2000-10-16
CZ14492A3 (en) 1994-01-19
SK14492A3 (en) 1995-02-08
RU2039035C1 (ru) 1995-07-09
ES2071428T3 (es) 1995-06-16
IL100679A (en) 1996-10-31
DE69201655T2 (de) 1995-07-13
FI920261A0 (fi) 1992-01-21
HUT61970A (en) 1993-03-29
IL100679A0 (en) 1992-09-06

Similar Documents

Publication Publication Date Title
EP0496561B1 (en) [[(2-Amino-3,4-dioxo-1-cyclobuten-1-yl)amino]alkyl]-acid derivatives
HK1005588B (en) [[(2-amino-3,4-dioxo-1-cyclobuten-1-yl)amino]alkyl]-acid derivatives
CS20192A3 (en) Amino acid derivatives, process of their preparation and use
US5273989A (en) 3,5-disubstituted 2-isoxazolines and isoxazoles, agents containing them and their use
HUT53879A (en) Improved process for producing decahydro-isoquinoline derivatives
GB2198134A (en) Substituted alpha -amino acids, their preparation and pharmaceutical compositions containing them
AU656811B2 (en) Benzimidazole phosphono-amino acids
US5424441A (en) N-aralkyl-and N-heteroaralkyl-aminoalkanephosphinic acids
Urbanovský et al. Selective and clean synthesis of aminoalkyl-H-phosphinic acids from hypophosphorous acid by phospha-Mannich reaction
CZ20021984A3 (cs) Nové (aminopropyl)methylfosfinové kyseliny
KR960008094B1 (ko) 아미노메틸렌 포스포노알킬포스피네이트의 합성방법
EP0418863B1 (en) NMDA antagonists
AU652399B2 (en) New heterocyclic compounds as antagonists of excitatory amino acid receptors, processes for their preparation and their use
AU746119B2 (en) Process for the preparation of (2-((8,9)- dioxo-2,6-diazabicyclo (5.2.0)-non-1(7)-en-2-yl)-ethyl) phosphonic acid
EP0879238B1 (en) Benzimidazole phosphono-amino acids
HU201302B (en) Process for production of peridiazodiazepines and medical compositions contqining them

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed