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AR248128A1 - Procedimiento para preparar esteres aromaticos sensibles o insensibles a oxidantes, utiles como inhibidores de la elastasa neutrofilica humana. - Google Patents

Procedimiento para preparar esteres aromaticos sensibles o insensibles a oxidantes, utiles como inhibidores de la elastasa neutrofilica humana.

Info

Publication number
AR248128A1
AR248128A1 AR91319728A AR31972891A AR248128A1 AR 248128 A1 AR248128 A1 AR 248128A1 AR 91319728 A AR91319728 A AR 91319728A AR 31972891 A AR31972891 A AR 31972891A AR 248128 A1 AR248128 A1 AR 248128A1
Authority
AR
Argentina
Prior art keywords
alkyl
alcoxy
cycloalkyl
insensitive
inhibitors
Prior art date
Application number
AR91319728A
Other languages
English (en)
Original Assignee
Cortech Inc
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 Cortech Inc filed Critical Cortech Inc
Application granted granted Critical
Publication of AR248128A1 publication Critical patent/AR248128A1/es

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/59Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen 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
    • C07D295/04Heterocyclic 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 substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14Heterocyclic 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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155Heterocyclic 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 substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/08Vasodilators for multiple indications
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/39Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C205/42Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/43Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/28Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/41Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
    • C07C309/42Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/16Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides
    • C07C317/44Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46Friedel-Crafts reactions
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/017Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/02Systems containing only non-condensed rings with a three-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/04Systems containing only non-condensed rings with a four-membered ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pulmonology (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)
  • Emergency Lowering Means (AREA)
  • Indole Compounds (AREA)
  • Pyrrole Compounds (AREA)

Abstract

PROCEDIMIENTO PARA PREPARAR COMPUESTOS DE FENIL O TETRAHIDRO NAFTILALCONOATOS DE FENILO, INSENSIBLES A LOS OXIDANTES, UTILES COMO INHIBIDORES DE ELASTASA NEUTROFILICA HUMANA, DE FORMULA VI, DONDE: R1 Y R2 SON H, ALQUILO, CICLOALQUILO O JUNTOS FORMAN METILENO -(CH2)N- DONDE N ES DE 1 A 6;R3 ES R3 O R3 PG, DONDE PG ES UN GRUPO PROTECTOR DONDE R3 ES H, HALOGENO, HALOALQUILO, ALQUILO, ALCOXI, ALQUENILO, CICLOALQUILO, ARILO MONO O DICICLICO, -ZR5 DONDE Z ES O, S, S(O) O SO2 Y R5 ES H, ALQUILO, CICLOALQUILO O FENILO;-NR6R7 DONDE R6 Y R7 SON H, ALQUILO, CICLOALQUILO, FENILO, ALCOXI, -C(O)R8 DONDE R8 ES ALQUILO, CICLOALQUILO, FENILO, CH3OC(O)CH2CH2-, HOOCCH2CH2-, NAO3SCH2NHC(O)CH2CH2- O R6 Y R7 JUNTOS FORMAN -C(O)CH2CH2C(O)-, -C(O)-C6H4-C(O) O (CH2)X- DONDE X ES 2, 3, 4, 5, O 6; MORFOLINO, IMIDAZOL O PIPERAZINO UNIDOS AL ANILLO FENILO A TRAVES DE NITROGENO;O R3 ES ALQUILENO SUSTITUIDO O NO POR ALCOXI O POR -O-(CH2)N-O- DONDE N VALE 2, 3 O 4, R4 ES HALOGENO, -C(O)CH3, S(O)PR9 DONDE P ES 0 , 1 O 2 Y R9 ES HIDROXI, -ONA O ALQUILO SUSTITUIDO O NO O CICLOALQUILO SUSTITUIDO O NO; O LAS SALES NO TOXICAS Y FARMACEUTICAMENTE ACEPTABLES DE LOS MISMOS, QUE CONSISTE EN:(A) HACER REACCIONAR UN ACIDO FENILACETICO DE FORMULA XXVIII;CON UN ALCOHOL EN MEDIO ACIDO PARA DAR COMPUESTO DE FORMULA XXIX;(B) CUANDO R1 O R2 NO ES H, TRATAR XXIX CON R1X Y/O R2X, PARA DAR XXX; (C) OBTENER EL CLORURO DE ACIDO II; (D) HACER REACCIONAR II, EN UNA BASE ORGANICA CON UN COMPUESTO III, (E) ELIMINAR LOS PG; (F) OXIDAR.
AR91319728A 1990-05-22 1991-05-21 Procedimiento para preparar esteres aromaticos sensibles o insensibles a oxidantes, utiles como inhibidores de la elastasa neutrofilica humana. AR248128A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US07/528,967 US5214191A (en) 1990-05-22 1990-05-22 Oxidant sensitive and insensitive aromatic esters as inhibitors of human neutrophil elastase

Publications (1)

Publication Number Publication Date
AR248128A1 true AR248128A1 (es) 1995-06-30

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Family Applications (1)

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AR91319728A AR248128A1 (es) 1990-05-22 1991-05-21 Procedimiento para preparar esteres aromaticos sensibles o insensibles a oxidantes, utiles como inhibidores de la elastasa neutrofilica humana.

Country Status (16)

Country Link
US (1) US5214191A (es)
EP (1) EP0465802A1 (es)
JP (1) JPH04226939A (es)
KR (1) KR920005712A (es)
CN (1) CN1056680A (es)
AR (1) AR248128A1 (es)
AU (1) AU640777B2 (es)
CA (1) CA2042904A1 (es)
FI (1) FI912468L (es)
HU (1) HUT58265A (es)
IE (1) IE911732A1 (es)
IL (1) IL98202A0 (es)
NO (1) NO175714C (es)
NZ (1) NZ238168A (es)
PT (1) PT97727A (es)
ZA (1) ZA913727B (es)

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AU647838B2 (en) * 1990-11-07 1994-03-31 Cortech, Inc. Ester inhibitors
US5240956A (en) * 1990-11-07 1993-08-31 Cortech, Inc. Ester inhibitors
US5216022A (en) * 1991-12-19 1993-06-01 Cortech, Inc. Aromatic esters of phenylenedialkanoates as inhibitors of human neutrophil elastase
US5795890A (en) * 1995-09-27 1998-08-18 Ono Pharmaceutical Co., Ltd. Sulfonamide derivatives
EP0994104A4 (en) * 1996-06-27 2001-09-12 Ono Pharmaceutical Co ARYL SULFIDE, SULFOXIDE AND SULPHONE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING THEM AS AN ACTIVE INGREDIENT
FR2755015B1 (fr) * 1996-10-25 1998-12-24 Sod Conseils Rech Applic Utilisation d'un extrait flavonoidique de ginkgo biloba substantiellement depourvu de terpenes, dans le domaine buccodentaire, et composition contenant un tel extrait
US6300514B1 (en) 1997-06-25 2001-10-09 Ono Pharmaceutical Co., Ltd. Aryl (sulfide, sulfoxide and sulfone) derivatives and drugs containing the same as the active ingredient
WO2000051625A1 (en) * 1999-03-05 2000-09-08 The Trustees Of University Technology Corporation Inhibitors of serine protease activity, methods and compositions for treatment of herpes viruses
AU3511500A (en) 1999-03-05 2000-09-21 Trustees Of University Technology Corporation, The Inhibitors of serine protease activity, methods and compositions for treatment of nitric oxide-induced clinical conditions
US6849605B1 (en) 1999-03-05 2005-02-01 The Trustees Of University Technology Corporation Inhibitors of serine protease activity, methods and compositions for treatment of viral infections
US6355666B1 (en) 2000-06-23 2002-03-12 Medinox, Inc. Protected forms of pharmacologically active agents and uses therefor
ES2333337T3 (es) 2000-08-29 2010-02-19 Biocon Limited Uso de una composicion farmaceutica que contiene un derivado de acido para-aminofenilacetico para tratar afecciones inflamatorias del tracto gastrointestinal.
US6548099B1 (en) 2000-11-28 2003-04-15 Hershey Foods Corporation Process for crystallizing amorphous lactose in milk powder
US8048924B2 (en) 2001-08-29 2011-11-01 Biocon Limited Methods and compositions employing 4-aminophenylacetic acid compounds
US20040220242A1 (en) * 2003-05-02 2004-11-04 Leland Shapiro Inhibitors of serine protease activity, methods and compositions for treatment of nitric oxide induced clinical conditions
TWI328009B (en) 2003-05-21 2010-08-01 Glaxo Group Ltd Quinoline derivatives as phosphodiesterase inhibitors
EP1773767B1 (en) 2004-07-07 2016-03-09 Biocon Limited Synthesis of azo bonded immunoregulatory compounds
US7741359B2 (en) * 2005-05-27 2010-06-22 Antibe Therapeutics Inc. Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
EP2041108B1 (en) * 2006-07-18 2014-05-21 Antibe Holdings Inc. 4-hydroxythiobenzamide derivatives of drugs

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CA949912A (en) * 1970-12-01 1974-06-25 Steven P. Cahill Carriage apparatus for serial printer
US3954767A (en) * 1972-05-17 1976-05-04 Esteve Subirana Antonio Piperazine salts of 2,5-dihydroxy benzene sulfonic acid mono- and diesters
CH591437A5 (es) * 1974-05-08 1977-09-15 Esteve Dr Lab Del Sa
US4115648A (en) * 1974-09-13 1978-09-19 Laboratorios Del Dr. Esteve, S.A. 2,5-Dihydroxy benzene sulfonic acid mono esters
FR2508033A1 (fr) * 1981-06-23 1982-12-24 Fabre Sa Pierre Aryl-1 aminomethyl-2 cyclopropanes carboxylates (z), leur preparation et leur application en tant que medicaments utiles dans le traitement d'algies diverses
DE3443308A1 (de) * 1984-11-28 1986-05-28 Bayer Ag, 5090 Leverkusen 1-heteroaryl-4-aryl-pyrazolin-5-one zur verwendung als arzneimittel

Also Published As

Publication number Publication date
NO175714C (no) 1994-11-23
FI912468A7 (fi) 1991-11-23
NO911956L (no) 1991-11-25
CA2042904A1 (en) 1991-11-23
FI912468A0 (fi) 1991-05-21
JPH04226939A (ja) 1992-08-17
IE911732A1 (en) 1991-12-04
PT97727A (pt) 1992-02-28
US5214191A (en) 1993-05-25
FI912468L (fi) 1991-11-23
NO911956D0 (no) 1991-05-21
AU7707691A (en) 1991-11-28
IL98202A0 (en) 1992-06-21
AU640777B2 (en) 1993-09-02
HU911703D0 (en) 1991-12-30
NZ238168A (en) 1995-07-26
KR920005712A (ko) 1992-04-03
EP0465802A1 (en) 1992-01-15
CN1056680A (zh) 1991-12-04
HUT58265A (en) 1992-02-28
NO175714B (no) 1994-08-15
ZA913727B (en) 1992-02-26

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