WO2003024946A3 - Derives d'oxamate contenant un heterocycle azote a substitutions diverses - Google Patents

Derives d'oxamate contenant un heterocycle azote a substitutions diverses Download PDF

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Publication number
WO2003024946A3
WO2003024946A3 PCT/EP2002/009435 EP0209435W WO03024946A3 WO 2003024946 A3 WO2003024946 A3 WO 2003024946A3 EP 0209435 W EP0209435 W EP 0209435W WO 03024946 A3 WO03024946 A3 WO 03024946A3
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WO
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Prior art keywords
substituted nitrogen
derivatives containing
nitrogen heterocycle
variously substituted
oxamate derivatives
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PCT/EP2002/009435
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English (en)
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WO2003024946A2 (fr
Inventor
Gerard Moinet
Caroline Leriche
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Merck Patent Gmbh
Gerard Moinet
Caroline Leriche
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Application filed by Merck Patent Gmbh, Gerard Moinet, Caroline Leriche filed Critical Merck Patent Gmbh
Priority to AU2002337009A priority Critical patent/AU2002337009A1/en
Publication of WO2003024946A2 publication Critical patent/WO2003024946A2/fr
Publication of WO2003024946A3 publication Critical patent/WO2003024946A3/fr

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/42One nitrogen atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic 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
    • C07D211/08Heterocyclic 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18Heterocyclic 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30Heterocyclic 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32Heterocyclic 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/06Heterocyclic 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
    • C07D211/08Heterocyclic 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18Heterocyclic 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34Heterocyclic 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61Halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72Nitrogen atoms
    • C07D213/74Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/36Sulfur atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182Radicals derived from carboxylic acids
    • C07D295/185Radicals derived from carboxylic acids from aliphatic carboxylic acids
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205Radicals derived from carbonic acid
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26Sulfur atoms
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    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings 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
    • C07D307/24Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom 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
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    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
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    • C07D317/44Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58Radicals substituted by nitrogen atoms
    • CCHEMISTRY; METALLURGY
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30Hetero atoms other than halogen
    • C07D333/34Sulfur atoms
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    • C07D333/26Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D333/00Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems

Abstract

L'invention concerne des composés de formule générale (I), dans laquelle R, R1, R2, R3, R4 et X sont tels que définis dans la revendication n°1. Ces composés peuvent être utilisés dans le traitement de pathologies associées au syndrome d'insulinorésistance.
PCT/EP2002/009435 2001-09-14 2002-08-23 Derives d'oxamate contenant un heterocycle azote a substitutions diverses WO2003024946A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002337009A AU2002337009A1 (en) 2001-09-14 2002-08-23 Oxamate derivatives containing a variously substituted nitrogen heterocycle

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0111950A FR2829766A1 (fr) 2001-09-14 2001-09-14 Derives d'oxamates comportant un heterocycle azote diversement substitue
FR01/11950 2001-09-14

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WO2003024946A2 WO2003024946A2 (fr) 2003-03-27
WO2003024946A3 true WO2003024946A3 (fr) 2003-12-04

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FR (1) FR2829766A1 (fr)
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GB201118613D0 (en) * 2011-10-27 2011-12-07 Nat Univ Ireland Compounds
RS55532B1 (sr) 2012-03-16 2017-05-31 Vitae Pharmaceuticals Inc Modulatori jetrenog x receptora
EA026907B1 (ru) 2012-03-16 2017-05-31 Вайтаи Фармасьютиклз, Инк. Модуляторы x рецепторов печени
CN104968656B (zh) * 2012-12-19 2017-08-11 诺华股份有限公司 自分泌运动因子抑制剂
US9409895B2 (en) * 2012-12-19 2016-08-09 Novartis Ag Autotaxin inhibitors
MY191366A (en) 2013-03-13 2022-06-20 Forma Therapeutics Inc Novel compounds and compositions for inhibition of fasn
TWI767148B (zh) 2018-10-10 2022-06-11 美商弗瑪治療公司 抑制脂肪酸合成酶(fasn)
US10793554B2 (en) 2018-10-29 2020-10-06 Forma Therapeutics, Inc. Solid forms of 4-(2-fluoro-4-(1-methyl-1H-benzo[d]imidazol-5-yl)benzoyl)piperazin-1-yl)(1-hydroxycyclopropyl)methanone

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GB1515291A (en) * 1975-05-05 1978-06-21 Shell Int Research Organic compositions containing an antioxidant
EP0106462A2 (fr) * 1982-09-04 1984-04-25 Pfizer Limited Dihydropyridines
EP0469889A1 (fr) * 1990-08-02 1992-02-05 Zeneca Limited Dérivés de (p-Carbonylaminophényl)-sulphonyl-nitrométhanes
EP0718287A2 (fr) * 1994-12-23 1996-06-26 Dr. Karl Thomae GmbH Dérivés de pipérazine, médicaments les contenant, leur application, et procédés pour leur préparation
WO1996020173A1 (fr) * 1994-12-23 1996-07-04 Dr. Karl Thomae Gmbh Derives de piperazine, medicaments contenant ces composes, leur utilisation et leur procede de preparation
WO1999046237A1 (fr) * 1998-03-12 1999-09-16 Novo Nordisk A/S Modulateurs de proteine-tyrosine-phosphatases
WO2000059880A1 (fr) * 1999-04-02 2000-10-12 Abbott Laboratories Composes inhibiteur de l'adhesion cellulaire, anti-inflammatoires et immunosuppresseurs
WO2001007440A1 (fr) * 1999-07-21 2001-02-01 Boehringer Ingelheim Pharmaceuticals, Inc. Anti-inflammatoires a base d'imidazoimidazoles et de triazoles
WO2001094342A1 (fr) * 2000-06-05 2001-12-13 Dong A Pharm. Co., Ltd. Nouveaux derives oxazolidinone et processus de preparation de ces derives

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GB1515291A (en) * 1975-05-05 1978-06-21 Shell Int Research Organic compositions containing an antioxidant
EP0106462A2 (fr) * 1982-09-04 1984-04-25 Pfizer Limited Dihydropyridines
EP0469889A1 (fr) * 1990-08-02 1992-02-05 Zeneca Limited Dérivés de (p-Carbonylaminophényl)-sulphonyl-nitrométhanes
EP0718287A2 (fr) * 1994-12-23 1996-06-26 Dr. Karl Thomae GmbH Dérivés de pipérazine, médicaments les contenant, leur application, et procédés pour leur préparation
WO1996020173A1 (fr) * 1994-12-23 1996-07-04 Dr. Karl Thomae Gmbh Derives de piperazine, medicaments contenant ces composes, leur utilisation et leur procede de preparation
WO1999046237A1 (fr) * 1998-03-12 1999-09-16 Novo Nordisk A/S Modulateurs de proteine-tyrosine-phosphatases
WO2000059880A1 (fr) * 1999-04-02 2000-10-12 Abbott Laboratories Composes inhibiteur de l'adhesion cellulaire, anti-inflammatoires et immunosuppresseurs
WO2001007440A1 (fr) * 1999-07-21 2001-02-01 Boehringer Ingelheim Pharmaceuticals, Inc. Anti-inflammatoires a base d'imidazoimidazoles et de triazoles
WO2001094342A1 (fr) * 2000-06-05 2001-12-13 Dong A Pharm. Co., Ltd. Nouveaux derives oxazolidinone et processus de preparation de ces derives

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Title
CHEMICAL ABSTRACTS, vol. 69, no. 17, 21 October 1968, Columbus, Ohio, US; abstract no. 67324, KATAOKA, HIROSHI ET AL: "Synthesis of oligomer of trans-2,5-dimethylpiperazine oxamide having terminal amino groups" *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; XP002201589, retrieved from STN Database accession no. 69:67324 *
G. RODALSKY: "Untersuchungen aus dem organischen Laboratorium der technischen Hochschule zu Dresden", J. PRAKT. CHEM., vol. 53, 1896, pages 19 - 24, XP008003576 *
H. MORREN ET AL.: "Contribution à l'étude des dérivés filaricides de la N.methylpipérazine", BULLETIN DES SOCIETES CHIMIQUES BELGES., vol. 59, 1950, PERGAMON PRESS LTD. OXFORD., GB, pages 228 - 237, XP002201587 *
MAYER, P. ET AL: "Metabolism of O,O-dipropyl S-[2-(2'-methyl-1'-piperidinyl)-2-oxo- ethyl] phosphorodithioate (C 19 490) in paddy rice", AGRIC. BIOL. CHEM. (1981), 45(2), 355-60, XP002201588 *
RYLSKI, LESZEK ET AL: "Synthesis of basic amides derived from.alpha.,.alpha.-bis(4- methoxyphenyl)glycolicacid", ACTA POL. PHARM. (1971), 28(3), 267-72, XP008003589 *
YUKI GOSEI KAGAKU KYOKAI SHI (1968), 26(5), 424-7 *

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FR2829766A1 (fr) 2003-03-21
WO2003024946A2 (fr) 2003-03-27

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