WO2003084525A1 - Nouvelle association d'un antithrombotique et d'aspirine - Google Patents

Nouvelle association d'un antithrombotique et d'aspirine Download PDF

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Publication number
WO2003084525A1
WO2003084525A1 PCT/FR2003/001054 FR0301054W WO03084525A1 WO 2003084525 A1 WO2003084525 A1 WO 2003084525A1 FR 0301054 W FR0301054 W FR 0301054W WO 03084525 A1 WO03084525 A1 WO 03084525A1
Authority
WO
WIPO (PCT)
Prior art keywords
aspirin
compound
pharmaceutically acceptable
pharmaceutical composition
association
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/FR2003/001054
Other languages
English (en)
French (fr)
Inventor
Tony Verbeuren
Gilbert Lavielle
Bernard Cimetiere
Marie-Odile Vallez
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Les Laboratoires Servier SAS
Original Assignee
Les Laboratoires Servier SAS
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 JP2003581765A priority Critical patent/JP4065853B2/ja
Priority to MXPA04009760A priority patent/MXPA04009760A/es
Priority to EP03745819A priority patent/EP1496884B1/fr
Priority to CA002480697A priority patent/CA2480697A1/fr
Priority to NZ535430A priority patent/NZ535430A/en
Priority to SI200330326T priority patent/SI1496884T1/sl
Priority to UA20041109009A priority patent/UA79457C2/uk
Priority to BR0309019-1A priority patent/BR0309019A/pt
Priority to EA200401293A priority patent/EA006978B1/ru
Priority to US10/509,605 priority patent/US7618955B2/en
Priority to HK05108135.4A priority patent/HK1076034B/xx
Priority to AU2003246774A priority patent/AU2003246774B2/en
Application filed by Les Laboratoires Servier SAS filed Critical Les Laboratoires Servier SAS
Priority to DE60306133T priority patent/DE60306133T2/de
Priority to KR1020047015845A priority patent/KR100645143B1/ko
Publication of WO2003084525A1 publication Critical patent/WO2003084525A1/fr
Anticipated expiration legal-status Critical
Priority to NO20044700A priority patent/NO20044700L/no
Priority to CY20061101027T priority patent/CY1105106T1/el
Ceased legal-status Critical Current

Links

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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
    • 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
    • A61K31/60—Salicylic acid; Derivatives thereof
    • A61K31/612—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid
    • A61K31/616—Salicylic acid; Derivatives thereof having the hydroxy group in position 2 esterified, e.g. salicylsulfuric acid by carboxylic acids, e.g. acetylsalicylic acid
    • 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
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • 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
    • 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
    • A61P9/12—Antihypertensives

Definitions

  • the subject of the new invention is a new combination of an antithrombotic and aspirin and the pharmaceutical compositions containing them.
  • the present invention relates to the combination of a TP receptor antagonist and aspirin.
  • Thromboxane A is an unstable metabolite of arachidonic acid which is involved in the pathogenesis of many disorders of the blood circulation. Thromboxane A 2 is a powerful platelet activator but also a powerful vasoconstrictor which has proliferative and pro-adhesive cellular properties.
  • TXA 2 and other metabolites of arachidonic acid such as endoperoxide (PGH 2 ), HETE and isoprostanes work through common receptors called TP receptors.
  • antiplatelet agents with aspirin have been described in the literature. These antiaggregating agents acting on platelet aggregation pathways (such as the purinergic pathways, ADP) which are different from those of aspirin which acts by the metabolism of arachidonic acid, it was expected to observe additive effects d activity between these compounds.
  • ADP purinergic pathways
  • compound A and aspirin both act on the pathways of arachidonic acid metabolism: the former acts by irreversibly inhibiting the cyclooxygenases which transform arachidonic acid into endoperoxide (PGH), the second acts by opposing the activity of certain metabolites of arachidonic acid such as thromboxane A, isoprostanes and endoperoxide.
  • PSH endoperoxide
  • the compound (A) and the aspirin can be in the form of pharmaceutically acceptable salts.
  • addition salts of compound (A) non-limiting mention may be made of the addition salts with a pharmaceutically acceptable base such as the sodium, potassium, tert-butylamine, diethylamine, etc. salts.
  • the salt used will be the sodium salt.
  • addition salts of aspirin non-limiting mention may be made of the addition salts with a pharmaceutically acceptable acid such as acetate, benzoate, fumarate, maleate, citrate, tartrate, lysine salt, etc. .
  • the compound (A) preferably has the absolute configuration (R).
  • the present invention also relates to pharmaceutical compositions containing a combination of compound (A) and aspirin, optionally in the form of pharmaceutically acceptable salts with one or more inert, non-toxic and suitable excipients.
  • compositions according to the invention mention may be made more particularly of those which are suitable for oral, parenteral, nasal administration, simple or coated tablets, sublingual tablets, capsules, tablets, suppositories, creams, ointments , dermal gels, etc.
  • the dosage is adaptable depending on the nature and severity of the condition, the route of administration and the age and weight of the patient.
  • the amounts of the active principles are between 1 and 300 mg for the compound (A) and between 10 and 1000 mg for the aspirin.
  • compositions according to the invention are therefore useful for the treatment of atherothrombotic diseases in which the activation of TP receptors and / or the formation of metabolites are involved as well as for the treatment of the consequences of these diseases.
  • pathologies include but are not limited to stable or unstable angina, endothelial or vascular dysfunction which accompanies diseases such as hypertension, diabetes, heart failure, disorders of the cardiovascular or cerebrovascular system, or thromboembolic disorders associated in particular with atherosclerosis.
  • the associations according to the invention were studied and the synergistic effect was demonstrated in an arterial thrombosis test in the guinea pig.
  • the guinea pigs are anesthetized with ketamine + xylazine (90 + 12) mg.kg i.m ..
  • the trachea is cannulated and the animals are kept breathing spontaneously.
  • the jugular vein is cannulated, allowing intravenous administration of the products to be tested.
  • the carotid artery is isolated, a Doppler probe is installed allowing the measurement of arterial blood flow. After stabilization, a lesion of the arterial wall is created by forceps, applied distal to the Doppler probe. Following this lesion, the blood flow decreases.
  • the antithrombotic activity of compound (A) is potentiated and increased by at least 30 times. Indeed, from the dose of 0.01 mg / kg, this effect is observed. This means that there is a very significant synergistic effect when these two active ingredients are administered simultaneously.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Obesity (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/FR2003/001054 2002-04-05 2003-04-04 Nouvelle association d'un antithrombotique et d'aspirine Ceased WO2003084525A1 (fr)

Priority Applications (16)

Application Number Priority Date Filing Date Title
MXPA04009760A MXPA04009760A (es) 2002-04-05 2003-04-04 Nueva asociacion de un agente antitrombotico con aspirina y su uso para tratamiento de enfermedades aterotromboticas.
EP03745819A EP1496884B1 (fr) 2002-04-05 2003-04-04 Association d'un antithrombotique et d'aspirin et son utilisation pour le traitement des maladies thrombotiques atherosclereuses
CA002480697A CA2480697A1 (fr) 2002-04-05 2003-04-04 Association d'un antithrombotique et d'aspirine
NZ535430A NZ535430A (en) 2002-04-05 2003-04-04 Novel association of an antithrombotic agent with aspirin and use thereof for treating atherothrombotic diseases
SI200330326T SI1496884T1 (sl) 2002-04-05 2003-04-04 Kombinacija antitrombotika in aspirina in njena uporaba za zdravljenje aterotromboticnih bolezni
UA20041109009A UA79457C2 (en) 2002-04-05 2003-04-04 Association of antithrombotic agent with aspirin and pharmaceutical composition for treating atherothrombotic diseases
BR0309019-1A BR0309019A (pt) 2002-04-05 2003-04-04 Associação de um antitrombótico e de aspirina, e sua utilização para o tratamento das doenças aterotrombóticas
US10/509,605 US7618955B2 (en) 2002-04-05 2003-04-04 Association of an antithrombotic and aspirin
EA200401293A EA006978B1 (ru) 2002-04-05 2003-04-04 Новое сочетание антитромботического агента и аспирина
JP2003581765A JP4065853B2 (ja) 2002-04-05 2003-04-04 抗血栓剤とアスピリンとの新規な組み合わせ及びアテローム血栓性疾患を処置するためのその使用
AU2003246774A AU2003246774B2 (en) 2002-04-05 2003-04-04 Novel association of an antithrombotic agent with aspirin and use thereof for treating atherothrombotic diseases
HK05108135.4A HK1076034B (en) 2002-04-05 2003-04-04 Novel association of an antithrombotic agent with aspirin and use thereof for the manufacture of a medicament for treating atherothrombotic diseases
DE60306133T DE60306133T2 (de) 2002-04-05 2003-04-04 Verbindung eines antithrombotischen mittels mit aspirin und dessen verwendung zur behandlung von atherothrombotischen erkrankungen
KR1020047015845A KR100645143B1 (ko) 2002-04-05 2003-04-04 항혈전제와 아스피린의 결합체 및 이의 죽상혈전성 질환을치료하기 위한 용도
NO20044700A NO20044700L (no) 2002-04-05 2004-10-29 Ny assoiasjon av et antitrombotisk middel og aspirin
CY20061101027T CY1105106T1 (el) 2002-04-05 2006-07-24 Συνδυασμος ενος αντιθρομβωτικου και ασπιρινης και η χρηση τους για την θεραπεια θρομβωτικων και αρτηριοσκληρωτικων ασθενειων

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0204222A FR2838057B1 (fr) 2002-04-05 2002-04-05 Nouvelle association d'un antithrombotique et d'aspirine
FR02/04222 2002-04-05

Publications (1)

Publication Number Publication Date
WO2003084525A1 true WO2003084525A1 (fr) 2003-10-16

Family

ID=28052120

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2003/001054 Ceased WO2003084525A1 (fr) 2002-04-05 2003-04-04 Nouvelle association d'un antithrombotique et d'aspirine

Country Status (26)

Country Link
US (1) US7618955B2 (https=)
EP (1) EP1496884B1 (https=)
JP (1) JP4065853B2 (https=)
KR (1) KR100645143B1 (https=)
CN (1) CN1297265C (https=)
AR (1) AR039253A1 (https=)
AT (1) ATE329591T1 (https=)
AU (1) AU2003246774B2 (https=)
BR (1) BR0309019A (https=)
CA (1) CA2480697A1 (https=)
CY (1) CY1105106T1 (https=)
DE (1) DE60306133T2 (https=)
DK (1) DK1496884T3 (https=)
EA (1) EA006978B1 (https=)
ES (1) ES2264533T3 (https=)
FR (1) FR2838057B1 (https=)
GE (1) GEP20074101B (https=)
MA (1) MA27114A1 (https=)
MX (1) MXPA04009760A (https=)
NO (1) NO20044700L (https=)
NZ (1) NZ535430A (https=)
PL (1) PL371620A1 (https=)
PT (1) PT1496884E (https=)
UA (1) UA79457C2 (https=)
WO (1) WO2003084525A1 (https=)
ZA (1) ZA200407593B (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2920772A1 (fr) * 2007-09-11 2009-03-13 Servier Lab Association entre un anti-atherothrombotique et un inhibiteur de l'enzyme de conversion de l'angiotensine

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SMP200800012B (it) * 2005-07-22 2008-02-27 Procter & Gamble Composizioni per ridurre l'incidenza di aritmia indotta da farmaco
EP2155195B1 (en) * 2007-04-13 2014-07-16 Millennium Pharmaceuticals, Inc. Combination anticoagulant therapy with a compound that acts as a factor Xa inhibitor
JP2009001537A (ja) * 2007-06-25 2009-01-08 Lab Servier 血管障害の処置を目的とする医薬の入手における抗アテローム血栓化合物の使用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0648741A1 (fr) * 1993-10-15 1995-04-19 Adir Et Compagnie Dérivés de 1,2,3,4-tétrahydronaphtalène, de chromanne et de thiochrtomanne comme agents antithromotiques

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0648741A1 (fr) * 1993-10-15 1995-04-19 Adir Et Compagnie Dérivés de 1,2,3,4-tétrahydronaphtalène, de chromanne et de thiochrtomanne comme agents antithromotiques

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CAYATTE ANTONIO J ET AL: "The thromboxane receptor antagonist S18886 but not aspirin inhibits atherogenesis in apo E-deficient mice: Evidence that eicosanoids other than thromboxane contribute to atherosclerosis.", ARTERIOSCLEROSIS THROMBOSIS AND VASCULAR BIOLOGY, vol. 20, no. 7, July 2000 (2000-07-01), pages 1724 - 1728, XP002223658, ISSN: 1079-5642 *
CIMETIÈRE B, DUBUFFET T, LANDRAS C, DESCOMBES J-J, SIMONET S, VERBEUREN TJ, LAVIELLE G: "New tetrahydronaphthalene derivatives as combined thromboxane receptor antagonists and thromboxane synthase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, 1998, pages 1381 - 1386, XP002223657 *
CIMETIERE BERNARD ET AL: "Synthesis and biological evaluation of new tetrahydronaphthalene derivatives as thromboxane receptor antagonists.", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 8, no. 11, 2 June 1998 (1998-06-02), pages 1375 - 1380, XP002223659, ISSN: 0960-894X *
MUTSCHLER E, GEISSLINGER G, KROEMER HK, SCHÄFER-KORTING M: "Mutschler Arzneimittelwirkungen - Lehrbuch der Pharmakologie und Toxikologie, 8. Auflage", 2001, WISSENSCHAFTLICHE VERLAGSGESELLSCHAFT MBH, STUTTGART, XP002223660 *
SIMONET S, DESCOMBES J-J, VALLEZ M-O, DUBUFFET T, LAVIELLE G, VERBEUREN TJ: "S 18886, A New Thromboxane (TP)-Receptor Antagonist is the Active Isomer of S 18204 in All Species, Except in the Guinea-Pig", ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY, vol. 433, 1997, US, pages 173 - 176, XP008010971 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2920772A1 (fr) * 2007-09-11 2009-03-13 Servier Lab Association entre un anti-atherothrombotique et un inhibiteur de l'enzyme de conversion de l'angiotensine
EP2036886A1 (fr) * 2007-09-11 2009-03-18 Les Laboratoires Servier Association entre un anti-athérothrombotique et un inhibiteur de l'enzyme de conversion de l'angiotensine
WO2009066035A3 (fr) * 2007-09-11 2009-08-27 Les Laboratoires Servier Association entre un anti-atherothrombotique et un inhibiteur de l'enzyme de conversion de l'angiotensine

Also Published As

Publication number Publication date
US7618955B2 (en) 2009-11-17
FR2838057A1 (fr) 2003-10-10
FR2838057B1 (fr) 2005-07-08
ES2264533T3 (es) 2007-01-01
UA79457C2 (en) 2007-06-25
HK1076034A1 (en) 2006-01-06
AU2003246774B2 (en) 2007-02-15
PT1496884E (pt) 2006-09-29
JP4065853B2 (ja) 2008-03-26
CN1646111A (zh) 2005-07-27
NZ535430A (en) 2006-09-29
CY1105106T1 (el) 2009-11-04
NO20044700L (no) 2004-10-29
EA200401293A1 (ru) 2005-02-24
EP1496884A1 (fr) 2005-01-19
BR0309019A (pt) 2005-02-01
DE60306133T2 (de) 2007-01-04
ZA200407593B (en) 2006-07-26
ATE329591T1 (de) 2006-07-15
CN1297265C (zh) 2007-01-31
MA27114A1 (fr) 2004-12-20
GEP20074101B (en) 2007-05-10
DK1496884T3 (da) 2006-10-02
JP2005528376A (ja) 2005-09-22
CA2480697A1 (fr) 2003-10-16
KR20040098053A (ko) 2004-11-18
KR100645143B1 (ko) 2006-11-10
DE60306133D1 (de) 2006-07-27
MXPA04009760A (es) 2004-12-13
US20050143354A1 (en) 2005-06-30
EP1496884B1 (fr) 2006-06-14
PL371620A1 (en) 2005-06-27
AU2003246774A1 (en) 2003-10-20
EA006978B1 (ru) 2006-06-30
AR039253A1 (es) 2005-02-16

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