IT1299266B1 - Inibitori reversibili della carnitina palmitoil trasferasi - Google Patents

Inibitori reversibili della carnitina palmitoil trasferasi

Info

Publication number
IT1299266B1
IT1299266B1 IT98MI001075A ITMI981075A IT1299266B1 IT 1299266 B1 IT1299266 B1 IT 1299266B1 IT 98MI001075 A IT98MI001075 A IT 98MI001075A IT MI981075 A ITMI981075 A IT MI981075A IT 1299266 B1 IT1299266 B1 IT 1299266B1
Authority
IT
Italy
Prior art keywords
carnitine
reversible
palmitoil
inhibitors
transferred
Prior art date
Application number
IT98MI001075A
Other languages
English (en)
Inventor
Fabio Giannessi
Mauro Marzi
Patrizia Minetti
Maria Ornella Tinti
Angelis Francesco De
Piero Chiodi
Arduino Arduini
Original Assignee
Sigma Tau Ind Farmaceuti
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
Priority to IT98MI001075A priority Critical patent/IT1299266B1/it
Application filed by Sigma Tau Ind Farmaceuti filed Critical Sigma Tau Ind Farmaceuti
Priority to EP04009193A priority patent/EP1484313B1/en
Priority to CA2329930A priority patent/CA2329930C/en
Priority to JP2000549576A priority patent/JP5127093B2/ja
Priority to HK01102605.2A priority patent/HK1033573B/en
Priority to KR1020007012826A priority patent/KR100585443B1/ko
Priority to PCT/IT1999/000126 priority patent/WO1999059957A1/en
Priority to EP99921135A priority patent/EP1077925B1/en
Priority to AT99921135T priority patent/ATE276230T1/de
Priority to DK99921135T priority patent/DK1077925T3/da
Priority to ES04009193T priority patent/ES2345100T3/es
Priority to PT99921135T priority patent/PT1077925E/pt
Priority to DE69920208T priority patent/DE69920208T2/de
Priority to AU38473/99A priority patent/AU3847399A/en
Priority to DK04009193.6T priority patent/DK1484313T3/da
Priority to PT04009193T priority patent/PT1484313E/pt
Priority to ES99921135T priority patent/ES2230854T3/es
Priority to DE69942315T priority patent/DE69942315D1/de
Priority to AT04009193T priority patent/ATE465988T1/de
Publication of ITMI981075A1 publication Critical patent/ITMI981075A1/it
Publication of IT1299266B1 publication Critical patent/IT1299266B1/it
Application granted granted Critical
Priority to US09/677,328 priority patent/US6369073B1/en
Priority to US09/986,327 priority patent/US6444701B1/en
Priority to US11/606,322 priority patent/USRE40861E1/en
Priority to US11/607,078 priority patent/USRE41226E1/en
Priority to CY20101100655T priority patent/CY1110200T1/el

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07C229/22—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 the carbon skeleton being further substituted by oxygen atoms
    • 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
    • C07C229/26—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 more than one amino group bound to the carbon skeleton, e.g. lysine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
    • C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C275/16—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/06—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
    • C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic 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
    • C07D295/04—Heterocyclic 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
    • C07D295/14—Heterocyclic 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
    • C07D295/145—Heterocyclic 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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic 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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • 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
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Child & Adolescent Psychology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Enzymes And Modification Thereof (AREA)
IT98MI001075A 1998-05-15 1998-05-15 Inibitori reversibili della carnitina palmitoil trasferasi IT1299266B1 (it)

Priority Applications (24)

Application Number Priority Date Filing Date Title
IT98MI001075A IT1299266B1 (it) 1998-05-15 1998-05-15 Inibitori reversibili della carnitina palmitoil trasferasi
AU38473/99A AU3847399A (en) 1998-05-15 1999-05-11 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
JP2000549576A JP5127093B2 (ja) 1998-05-15 1999-05-11 カルニチンパルミトイル−トランスフェラーゼの可逆的阻害活性を有する化合物
HK01102605.2A HK1033573B (en) 1998-05-15 1999-05-11 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
KR1020007012826A KR100585443B1 (ko) 1998-05-15 1999-05-11 카르니틴 팔미토일-트랜스퍼라제의 활성을 가역적으로억제하는 화합물
PCT/IT1999/000126 WO1999059957A1 (en) 1998-05-15 1999-05-11 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
EP99921135A EP1077925B1 (en) 1998-05-15 1999-05-11 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
AT99921135T ATE276230T1 (de) 1998-05-15 1999-05-11 Verbindungen, die als reversible inhibitoren der carnitin palmitoyltransferase wirsam sind
DK99921135T DK1077925T3 (da) 1998-05-15 1999-05-11 Forbindelser med reversibel inhiberende aktivitet af carnitinpalmitoyltransferase
ES04009193T ES2345100T3 (es) 1998-05-15 1999-05-11 Compuestos que tienen actividad inhibidora reversible de carnitina palmitoiltransferasa.
PT99921135T PT1077925E (pt) 1998-05-15 1999-05-11 Compostos possuindo actividade de inibicao reversivel de palmitoil-transferasede carnitina
CA2329930A CA2329930C (en) 1998-05-15 1999-05-11 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
EP04009193A EP1484313B1 (en) 1998-05-15 1999-05-11 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
DE69920208T DE69920208T2 (de) 1998-05-15 1999-05-11 Verbindungen, die als reversible inhibitoren der carnitin palmitoyltransferase wirsam sind
DK04009193.6T DK1484313T3 (da) 1998-05-15 1999-05-11 Forbindelser, som har reversibel inhiberende aktivitet af carnitin-palmitoyltransferase
ES99921135T ES2230854T3 (es) 1998-05-15 1999-05-11 Compuestos que tienen actividad inhibidora reversible de carnitin.-palmitoil transferasa.
DE69942315T DE69942315D1 (de) 1998-05-15 1999-05-11 Verbindungen, die als reversible Inhibitoren der Carnitin Palmitoyltransferase wirksam sind
AT04009193T ATE465988T1 (de) 1998-05-15 1999-05-11 Verbindungen, die als reversible inhibitoren der carnitin palmitoyltransferase wirksam sind
PT04009193T PT1484313E (pt) 1998-05-15 1999-05-11 Compostos que apresentam acã†o inibidora reversvel das carnitina-palmitoil transferases
US09/677,328 US6369073B1 (en) 1998-05-15 2000-10-02 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
US09/986,327 US6444701B1 (en) 1998-05-15 2001-11-08 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
US11/606,322 USRE40861E1 (en) 1998-05-15 2006-11-30 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
US11/607,078 USRE41226E1 (en) 1998-05-15 2006-12-01 Compounds having reversible inhibiting activity of carnitine palmitoyl-transferase
CY20101100655T CY1110200T1 (el) 1998-05-15 2010-07-13 Ενώσεις που εχουν παρεμποδιστική δραση της παλμιτοϋλ-τρανσφερασης της καρνιτίνης

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT98MI001075A IT1299266B1 (it) 1998-05-15 1998-05-15 Inibitori reversibili della carnitina palmitoil trasferasi

Publications (2)

Publication Number Publication Date
ITMI981075A1 ITMI981075A1 (it) 1999-11-15
IT1299266B1 true IT1299266B1 (it) 2000-02-29

Family

ID=11380036

Family Applications (1)

Application Number Title Priority Date Filing Date
IT98MI001075A IT1299266B1 (it) 1998-05-15 1998-05-15 Inibitori reversibili della carnitina palmitoil trasferasi

Country Status (14)

Country Link
US (4) US6369073B1 (it)
EP (2) EP1484313B1 (it)
JP (1) JP5127093B2 (it)
KR (1) KR100585443B1 (it)
AT (2) ATE465988T1 (it)
AU (1) AU3847399A (it)
CA (1) CA2329930C (it)
CY (1) CY1110200T1 (it)
DE (2) DE69942315D1 (it)
DK (2) DK1484313T3 (it)
ES (2) ES2230854T3 (it)
IT (1) IT1299266B1 (it)
PT (2) PT1484313E (it)
WO (1) WO1999059957A1 (it)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
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IT1299266B1 (it) 1998-05-15 2000-02-29 Sigma Tau Ind Farmaceuti Inibitori reversibili della carnitina palmitoil trasferasi
US6822115B2 (en) * 1999-06-30 2004-11-23 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Synthesis of (R) and (S)-aminocarnitine, (R) and (S)-4-phosphonium-3-amino-butanoate, (R) and (S) 3,4-diaminobutanoic acid, and their derivatives starting from D- and L-aspartic acid
IT1317885B1 (it) * 2000-08-01 2003-07-15 Sigma Tau Ind Farmaceuti Uso di fibrati per la preparazione di un medicamento utile neltrattamento dell'insufficienza cardiaca congestizia.
ITRM20010456A1 (it) * 2001-07-26 2003-01-27 Sigma Tau Ind Farmaceuti Procedimento per la preparazione di (r)- o (s)- amminocarnitina sale interno, dei suoi sali e dei suoi derivati.
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US7041286B2 (en) * 2003-07-23 2006-05-09 Nerenberg Arnold P Composition for mitigating a pernicious thrombotic event
US8314144B2 (en) 2004-02-12 2012-11-20 Defiante Farmaceutica, S.A. Compounds having antitumor activity
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WO2009002433A1 (en) * 2007-06-22 2008-12-31 Dara Biosciences, Inc. Compositions and methods for treating skin disorders
WO2009015485A1 (en) * 2007-08-01 2009-02-05 University Health Network Cyclic inhibitors of carnitine palmitoyltransferase and treating cancer
WO2009019199A1 (en) * 2007-08-07 2009-02-12 Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. Crystalline teglicar
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EP1484313B1 (en) 2010-04-28
ATE276230T1 (de) 2004-10-15
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WO1999059957A1 (en) 1999-11-25
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DE69920208T2 (de) 2005-10-20
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US6444701B1 (en) 2002-09-03
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US20020052348A1 (en) 2002-05-02
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US6369073B1 (en) 2002-04-09
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CA2329930C (en) 2010-02-23
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