OA10554A - Compounds and pharmaceutical compositions containing them - Google Patents

Compounds and pharmaceutical compositions containing them Download PDF

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Publication number
OA10554A
OA10554A OA70171A OA70171A OA10554A OA 10554 A OA10554 A OA 10554A OA 70171 A OA70171 A OA 70171A OA 70171 A OA70171 A OA 70171A OA 10554 A OA10554 A OA 10554A
Authority
OA
OAPI
Prior art keywords
formula
pyridyl
compound
aminomethylphosphonate
diethyl
Prior art date
Application number
OA70171A
Other languages
English (en)
Inventor
Lan Mong Nguyen
Eric Niesor
Craig Leigh Bentzen
Hieu Trung Phan
Vinh Van Diep
Simon Floret
Raymond Azoulay
Original Assignee
Symphar Sa
Smithkline Beecham Plc
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 Symphar Sa, Smithkline Beecham Plc filed Critical Symphar Sa
Publication of OA10554A publication Critical patent/OA10554A/en

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Classifications

    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
    • 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
    • A61K31/66—Phosphorus compounds
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • 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
    • 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
    • C07F9/4056—Esters of arylalkanephosphonic 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/58—Pyridine rings
    • 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
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings
    • 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
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (22)

  1. 39 010554 Claims
    X1 is H, C(i-3)alkyl, hydroxy or C(i_4)alkoxy;is C(i_3)alkyl or C(i_4)alkoxy; X^ is H or C(i _4)alkyl; Rl, R^, which may be identical or different, are H or C(j.3)alkyl; B is CH2CH2, CH=CH, or CH2; n is zéro or 1; Z is H or a C^j.gjalkyl group; misOorl; X4 is H, or C(i _g)alkyl, Cq .g^alkoxy or halo; and the pyridyl ring is attached by the ring carbon a- or β- to the nitrogen (2- or3-pyridyl); or a pharmaceutically acceptable sait, thereof; and
  2. 2. A compound as claimed in claim 1 in which, in the compound of formula (la),χΐ is hydrogen, methyl or methoxy.
  3. 3. A compound as claimed claim 1 or 2 in which, in the compound of formula(la), X^ is methyl or methoxy.
  4. 4. A compound as claimed in claim 1 in which, in the compound of formula (la),X1 and X^ are both C(i_4)alkoxy or one of X^ and X^ is C(i.3)alkyl and theother is C(i_4)alkoxy.
  5. 5. A compound as claimed in claim 1 in which, in the compound of formula (la),χΐ and X^ are methoxy and methoxy, methoxy and methyl, n-propyl or iso-propyk or methyl and methyl or t-butyl, respectively. 010554
  6. 6. A compound as claimed in any one of daims 1 to 5 in which, in the compoundof formula (la), is hydrogen.
  7. 7. A compound as claimed in any one of daims 1 to 6 in which, in the compoundof formula (la), (B)n is a direct bond.
  8. 8. A compound as claimed in any one of daims 1 to 7 in which, in the compoundof formula (la), Rl and R^ is each a straight or branched C(i_3)alkyl group.
  9. 9. A compound as claimed in daim 8 in which, in the compound of formula (la),Rl and R^ is each a C2 or C3 alkyl group.
  10. 10. A compound as claimed in any one of daims 1 to 9 in which, in thecompound of formula (la), Z is hydrogen.
  11. 11. A compound as claimed in any one of daims 1 to 10 in which, in thecompound of formula (la), X^ is hydrogen or methyl which is preferably on thering carbon adjacent to N.
  12. 12. A compound as claimed in any one of daims 1 to 11 in which, in thecompound of formula (la), the pyridyl ring is attached by the ring carbon β- to thenitrogen (3-pyridyl).
  13. 13. A compound of formula (la) as defined in daim 1 selected from:diethyl a-(4-hydroxyphenyl)-N-(3-pyridyl)-aminomethylphosphonate,diethyl a-(3,4-methylenedioxyphenyl)-N-(3-pyridyl)-aminophosphonate,diethyl a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(3-pyridyl)-aminomethylphosphonate, dimethyl a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(3-pyridyl)- aminomethylphosphonate, diisopropyl ct-(3,5-dimethoxy-4-hydroxyphenyi)-N-(3-pyridyl)- aminomethylphosphonate, diethyl a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(2-pyridyl)- aminomethylphosphonate, diethyl a-(3,5-dimethoxy-4-hydroxyphenyI)-N-(4-pyridyl)- aminomethylphosphonate, 41 010554 diethyl a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(2-picolyl)- aminomethylphosphonate, diethyl a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(3-picolyl)- aminomethylphosphonate, diethyl a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(4-picolyl)- aminomethylphosphonate, diethyl a-(4-hydroxy-3-methoxyphenyl)-N-(3-pyridyl)-aminomethylphosphonate,diethyl a-(3-ethoxy-4-hydroxyphenyl)-N-(3-pyridyl)-aminomethylphosphonate,diethyl a-(3,4,5-trimethoxyphenyl)-N-(3-pyridyl)-aminomethylphosphonate,diethyl <x-(3,5-dimethyl-4-hydroxyphenyl)-N-(3-pyridyl)- aminomethylphosphonate, (+)-diethy 1 a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(3-pyridyl)- aminomethyiphosphonate, (-)-diethyl a-(3,5-dimethoxy-4-hydroxyphenyl)-N-(3-pyridyl)- aminomethylphosphonate. diisopropyl a-(3,5-di-methoxy-4-hydroxyphenyl)-N-[5-(2methyl-pyridyl)]-aminomethylphosphonate, diethyl a-(4-hydroxy-3-methoxy-5-methylphenyl)-N-(3-pyridyl)-amino-methylphosphonate, diisopropyl a-(4-hydroxy-3-methoxy-5-methylphenyl)-N-(3-pyridyl)-amino-methylphosphonate, diethyl a-(4-hydroxy-3-methoxy-5-n-propylphenyl)-N-(3-pyridyl)- aminomethylphosphonate; and diisopropyl a-(4-hydroxy-3-methoxy-5-n-propylphenyI)-N-(3-pyridyl)-aminomethylphosphonate.
  14. 14. A pharmaceutical composition comprising a compound of formula (la) asdefined in claim 1 and a pharmaceutically acceptable carrier or excipient.
  15. 15. A compound of formula (la) as defined in claim 1 for use in therapy.
  16. 16. The use of a compound of formula (la) as defined in claim 1 for themanufacture of a médicament for the treatment of peripheral artery disease bydecreasing plasma lipoprotein(a) levels. 42 010554
  17. 17. The use of a compound of formula (la) as defined in claim 1 for themanufacture of a médicament for the treatment of thrombosis by decreasingplasma lipoprotein(a) levels.
  18. 18. The use of a compound of formula (la) as defined in claim 1 for themanufacture of a médicament for the treatment of restenosis followingangioplasty by decreasing plasma lipoprotein(a) levels.
  19. 19. The use of a compound of formula (la) as defined in claim 1 for themanufacture of a médicament for the treatment of atherosclerosis by decreasingplasma lipoprotein(a) levels.
  20. 20. A process for preparing a compound of formula (la) as defined in claim 1which process comprises (a) when Z is hydrogen, treating an imine of formula (II):
    (Π) in which B, , X2, χ3 and n are as defined in claim 21 ; with a phosphite compound of formula (III): HPO(ORl)(OR2) (III) in which Rl and R2 are as defined in claim 1 ; or a trialkyl silyl dérivative or métalsait thereof; in the presence or absence of a catalyst, optionally in a solvent; (b) for compounds of formula (la) in which Z is not hydrogen, treating equimolaramounts of an aldéhyde of formula (V): 1 010554 4?
    (B)nCHO (V) in which B, χΐ, X2, χ3 and n are as defîned in claim 21 ;with a secondary amine of formula (VII): HNZA (VII) in which Z is a C^.g^alkyl group and A is as hereinbefore defîned; anda phosphite of formula (III); (c) in compounds of formula (I) in which m is not zéro, treating a compound offormula (VIII):
    (VIII) in which B, R1, R2, X1, X2, X3 and n are as defîned in claim 21 ;an aldéhyde of formula (IX): X4-+ j“(CH2WH0 (IX) in which m is an integer from 1 to 5 and X4 is as hereinbefore defînedunder reductive amination conditions.
  21. 21. A process for preparing an individual enantiomer of an aminophosphonate offormula (la) as defîned in claim 1 which process comprises treating either of the 44 010554 (+) or (-) enantiomer of the α-substituted aminomethylphosphonate of formula (X):
    (X) in which B, RJ, R^, χΐ, χ2, χ3 and n are as defined in claim 1 ;with an aldéhyde of formula (XI): R3-CHO (XI) in which R3 is an alkyl group from 1 to 4 carbon atoms, a perfluoroalkyl groupfrom 1 to 4 carbon atoms; under reductive amination conditions.
  22. 22. A process as claimed in claim 21 in which the reaction is carried out in thepresence of sodium cyanoborohydride in an alcoholic solvent, preferablymethanol, at a pH between 3 to 6 and at a température between 0°C and 25°C.
OA70171A 1995-06-30 1997-12-30 Compounds and pharmaceutical compositions containing them OA10554A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH01920/95A CH690264A5 (fr) 1995-06-30 1995-06-30 Dérivés aminophosphonates substitués, leur procédé de préparation et leur utilisation pour la préparation de compositions pharmaceutiques.

Publications (1)

Publication Number Publication Date
OA10554A true OA10554A (en) 2002-05-29

Family

ID=4221681

Family Applications (1)

Application Number Title Priority Date Filing Date
OA70171A OA10554A (en) 1995-06-30 1997-12-30 Compounds and pharmaceutical compositions containing them

Country Status (27)

Country Link
US (2) US6060464A (fr)
EP (1) EP0835116A1 (fr)
JP (1) JPH11508576A (fr)
KR (1) KR19990028542A (fr)
CN (1) CN1113654C (fr)
AP (1) AP778A (fr)
AR (1) AR004498A1 (fr)
AU (1) AU705206B2 (fr)
BG (1) BG102215A (fr)
BR (1) BR9609653A (fr)
CA (1) CA2225391A1 (fr)
CH (1) CH690264A5 (fr)
CZ (1) CZ422097A3 (fr)
EA (1) EA199800106A1 (fr)
HU (1) HUP9901684A3 (fr)
IL (1) IL122717A0 (fr)
MA (1) MA24340A1 (fr)
MX (1) MX9800189A (fr)
NO (1) NO976128L (fr)
NZ (1) NZ312696A (fr)
OA (1) OA10554A (fr)
PL (1) PL187024B1 (fr)
SK (1) SK178397A3 (fr)
TR (1) TR199701700T1 (fr)
TW (1) TW413681B (fr)
WO (1) WO1997002037A1 (fr)
ZA (1) ZA965505B (fr)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6548084B2 (en) 1995-07-20 2003-04-15 Smithkline Beecham Plc Controlled release compositions
GB9626615D0 (en) * 1996-12-20 1997-02-05 Symphar Sa Novel compounds
GB9626536D0 (en) * 1996-12-20 1997-02-05 Symphar Sa Novel compounds
GB9626616D0 (en) * 1996-12-20 1997-02-05 Symphar Sa Novel compounds
DE19748659A1 (de) * 1997-11-04 1999-05-06 Hoechst Ag Aminophosphoniumgruppen enthaltende vernetzte Copolymere für medizinische Verwendungen
US6017918A (en) * 1998-08-06 2000-01-25 Warner-Lambert Company Phenyl glycine compounds and methods of treating atherosclerosis and restenosis
US6284795B1 (en) 1998-09-04 2001-09-04 Warner-Lambert Company Sulfonamide compounds and methods of treating atherosclerosis and restenosis
IL149308A0 (en) 1999-10-27 2002-11-10 Teva Pharma Use of 1-aminoindan derivatives for treatment of manic disorders
NZ520752A (en) 2000-02-16 2004-03-26 Smithkline Beecham P Pyrimidine-4-one derivatives as LDL-PLA2 inhibitors
US20030114421A1 (en) * 2000-09-27 2003-06-19 Phan Hieu Trung Alpha-substituted beta-aminoethyl phosphonate derivatives
EP1320536A1 (fr) * 2000-09-27 2003-06-25 Ilex Oncology Research S.A. $g(b)-AMINOETHYLPHOSPHONATES $g(a)-SUBSTITUES
GB0024808D0 (en) 2000-10-10 2000-11-22 Smithkline Beecham Plc Novel compounds
GB0025849D0 (en) * 2000-10-23 2000-12-06 Smithkline Beecham Plc Novel compounds
MXPA04007797A (es) * 2002-02-11 2005-09-08 Ilex Products Inc Derivados de fosfonato heteroarilalquilo a-sustituidos.
AU2003228990A1 (en) * 2002-05-11 2003-11-11 Ilex Products, Inc. Hydroxyphosphonates and phosphonophosphates as apolipoprotein e modulators
EP1534679A4 (fr) * 2002-08-30 2007-06-06 Biostratum Inc Inhibiteurs de produits terminaux avances de glycation post-amadori
KR101861883B1 (ko) 2010-12-06 2018-05-28 글락소 그룹 리미티드 Lp-PLA₂에 의해 매개되는 질환 또는 상태의 치료에 사용하기 위한 피리미디논 화합물
EP2739627A4 (fr) 2011-07-27 2015-01-21 Glaxo Group Ltd Composés 2,3-dihydroimidazo[1,2-c]pyrimidin-5(1h)-one et utilisation en tant qu'inhibiteurs de lp-pla2
EP2736908A1 (fr) 2011-07-27 2014-06-04 Glaxo Group Limited Composés pyrimidones bicycliques
SI2751094T1 (sl) 2011-09-01 2018-10-30 Glaxo Group Limited Nova kristalinična oblika
UY35276A (es) 2013-01-25 2014-08-29 Glaxosmithkline Ip Dev Ltd Nuevos compuestos que inhiben la actividad de Lp-PLA2
CA2899124A1 (fr) 2013-01-25 2014-07-31 Glaxosmithkline Intellectual Property Development Limited Composes
BR112015017397A2 (pt) 2013-01-25 2017-07-11 Glaxosmithkline Ip Dev Ltd compostos pirimidona bicíclica como inibidores de lp-pla2
WO2016012917A1 (fr) 2014-07-22 2016-01-28 Glaxosmithkline Intellectual Property Development Limited Dérivés 1,2,3,5-tétrahydro-imidazo [1,2-c]pyrimidine utiles pour le traitement de maladies et de troubles médiés par la lp-pla2
WO2016012916A1 (fr) 2014-07-22 2016-01-28 Glaxosmithkline Intellectual Property Development Limited Dérivés 1,2,3,5-tétrahydro-imidazo [1,2-c]pyrimidine utiles pour le traitement de maladies et de troubles médiés par la lp-pla2
CN114805389B (zh) 2019-11-09 2023-08-29 上海赛默罗生物科技有限公司 三环二氢咪唑并嘧啶酮衍生物、其制备方法、药物组合物和用途
CN115304620A (zh) 2021-05-07 2022-11-08 上海赛默罗生物科技有限公司 嘧啶酮衍生物、其制备方法、药物组合物和用途

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH683996A5 (fr) * 1992-03-05 1994-06-30 Symphar Sa Dérivés aminophosphonates substitués, leur procédé de préparation et compositions pharmaceutiques les contenant.
DE4433244A1 (de) * 1994-09-19 1996-03-28 Hoechst Ag Aminomethylphosphon- und Aminomethylphosphinsäure-Derivate und deren Verwendung zur Behandlung von degenerativen Gelenkserkrankungen

Also Published As

Publication number Publication date
AU705206B2 (en) 1999-05-20
AR004498A1 (es) 1998-12-16
US6660724B1 (en) 2003-12-09
CZ422097A3 (cs) 1998-10-14
HUP9901684A3 (en) 2000-04-28
KR19990028542A (ko) 1999-04-15
ZA965505B (en) 1998-03-30
JPH11508576A (ja) 1999-07-27
CN1113654C (zh) 2003-07-09
MX9800189A (es) 1998-04-30
CA2225391A1 (fr) 1997-01-23
EP0835116A1 (fr) 1998-04-15
US6060464A (en) 2000-05-09
PL324341A1 (en) 1998-05-25
NO976128D0 (no) 1997-12-29
AU6418596A (en) 1997-02-05
EA199800106A1 (ru) 1998-08-27
MA24340A1 (fr) 1998-07-01
PL187024B1 (pl) 2004-04-30
CH690264A5 (fr) 2000-06-30
IL122717A0 (en) 1998-08-16
NZ312696A (en) 1999-10-28
TR199701700T1 (xx) 1998-03-21
TW413681B (en) 2000-12-01
NO976128L (no) 1998-02-10
AP9701160A0 (en) 1998-01-31
CN1193913A (zh) 1998-09-23
WO1997002037A1 (fr) 1997-01-23
AP778A (en) 1999-10-29
BR9609653A (pt) 1999-12-21
BG102215A (en) 1998-09-30
SK178397A3 (en) 1998-06-03
HUP9901684A2 (hu) 1999-09-28

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