WO2006066894A1 - Composes destines au traitement d'un syndrome metabolique - Google Patents

Composes destines au traitement d'un syndrome metabolique Download PDF

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Publication number
WO2006066894A1
WO2006066894A1 PCT/EP2005/013777 EP2005013777W WO2006066894A1 WO 2006066894 A1 WO2006066894 A1 WO 2006066894A1 EP 2005013777 W EP2005013777 W EP 2005013777W WO 2006066894 A1 WO2006066894 A1 WO 2006066894A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
benzoic acid
compound according
acetoxy
compounds
Prior art date
Application number
PCT/EP2005/013777
Other languages
English (en)
Inventor
Urs Scherrer
Anna Sparatore
Original Assignee
Ctg Pharma S.R.L.
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 Ctg Pharma S.R.L. filed Critical Ctg Pharma S.R.L.
Priority to EP05820150A priority Critical patent/EP1836160A1/fr
Priority to US11/722,406 priority patent/US20090036516A1/en
Publication of WO2006066894A1 publication Critical patent/WO2006066894A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/02—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00 containing nitrogen-oxide bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid

Definitions

  • Metabolic Syndrome a newly recognized clinical entity, is also called the “deadly quartet" of insulin
  • cardiovascular disease (3-4 times ) , and greatly increases the risk of developing diabetes (up to 25 times) and aggravates its associated complications .
  • the metabolic syndrome also is associated with an
  • i Metabolic syndrome is characterized by a tissue
  • R - OCOCH 3 , -OH
  • R' is H, methyl , ethyl or
  • Z H, -OCO (CH 2 ) nONO 2 or -O (CH 2 ) n ONO 2 , where n is an integer from 1 to 10
  • X H or - (CH 2 ) n ONO 2 , provided that at least one of Z , X, R and R' contain a NO 2 group or a sulfur atom and that
  • Preferred compounds are:
  • ROS/RNS Species
  • NF-KB ubiquitous nuclear transcription factor KB
  • AGEs advanced glycation endproducts
  • the compounds of the present invention act also as AGE inhibitors .
  • gasotransmitters such as NO or H 2 S occupy a prominent role .
  • important aspects need to be taken into account .
  • gasotransmitters are capable to inhibit effectively oxidative stress , they are themselves often present as radicals , particularly when massively
  • oxidative stress may also impair anti-oxidant defense mechanisms .
  • the oxidative stress may also impair anti-oxidant defense mechanisms .
  • gasotransmitters have the potential to reduce oxidative
  • characteristics of the gasotransmitter are another important aspect that needs to be considered.
  • NO-aspirin is very lipophilic and therefore poorly
  • Lipoic acid is a coenzyme in the oxidative decarboxylation of ⁇ -keto acids and is found in virtually every cell in the body .
  • lipoic acid has some relevant drawbacks , being absorbed by oral route only in a partial
  • the products can be used in racemic mixture or in form of single enantiomer .
  • cardiovascular system for example myocardial and vascular ischemia in general , hypertension systemic and
  • connective tissue disease for example arthritis and connected inflammatory diseases , etc
  • respiratory system for example
  • urogenital system for example impotence, incontinence,
  • central nervous system Alzheimer's disease
  • cutaneous system eczema, neurodermatitis .
  • organs colon, lung, prostate, ovaries , uterus , breast, tongue, liver, bone, etc . ) . . ) , in prevention and/or treatment as monotherapy or in association with other
  • the compounds of the present invention can be used for all the therapeutic indications where the parent
  • non-toxic amines and aminoacids are also part of the present invention .
  • Preferred salts are the salts with arginine and agmatine .
  • L-arginine and agmatine ( its decarboxylated analog) salts are precursors for nitric oxide, an endogenous messenger molecule involved in a variety of endothelium-mediated physiological effects in the vascular system.
  • subj ects may be administered compounds of the present invention at any suitable therapeutically effective and safe dosage, as may be readily determined
  • compounds of the present invention may be administered at a dosage between about 1 and 90 mg/kg, and more preferably between
  • inflammatory disease is metabolic syndrome, diabetes ,
  • formula ( I ) is administered at a dose of about 10 mg to about Ig .
  • the compounds of the present invention can be administered in the form of any pharmaceutical formulation, the nature of which will depend upon the
  • compositions can be prepared by conventional methods , using compatible, pharmaceutically acceptable excipients or vehicles .
  • examples of such compositions include
  • capsules for the preparation of extemporaneous solutions , injectable preparations , rectal , nasal , ocular, vaginal etc .
  • a preferred route of administration is the oral and rectal route .
  • the last step was a nitration with a mixture constituted by 0.25 ml of fuming HNO 3 , 0.63 ml of acetic anhydride and 5.38 ml of methylene choride . This mixture
  • the acylchloride of lipoic acid was prepared adding
  • the 2-acetyl-5- ( 5-bromopentanoyl) benzoic acid was dissolved in acetonitrile and a solution of silver
  • dithiolethione were mixed with 7.5 g of pyridine HCl and the mixture was heated for 25 minutes at 215 0 C .
  • the resulting product was a viscous yellow oil with an
  • dithiolethione were mixed with 7.5 g of pyridine HCl and the mixture was heated for 25 minutes at 215°C .
  • BSO buthionine sulphoximine
  • Vehicle Carboxymethylcellulose 0.5% (w/w) in water

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne des composés représentés par la formule générale (I), dans laquelle R', R, x et z sont tels que définis dans les spécifications, lesquels sont utiles pour le traitement de maladies inflammatoires telles que syndrome métabolique, diabète, obésité, dyslipidémie et résistance à l'insuline.
PCT/EP2005/013777 2003-01-13 2005-12-21 Composes destines au traitement d'un syndrome metabolique WO2006066894A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP05820150A EP1836160A1 (fr) 2004-12-24 2005-12-21 Composes destines au traitement d'un syndrome metabolique
US11/722,406 US20090036516A1 (en) 2003-01-13 2005-12-21 Compounds for treating metabolic syndrome

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2004000724 2004-12-24
ITPCT/IT2004/000724 2004-12-24

Publications (1)

Publication Number Publication Date
WO2006066894A1 true WO2006066894A1 (fr) 2006-06-29

Family

ID=34959966

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/013777 WO2006066894A1 (fr) 2003-01-13 2005-12-21 Composes destines au traitement d'un syndrome metabolique

Country Status (2)

Country Link
EP (1) EP1836160A1 (fr)
WO (1) WO2006066894A1 (fr)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008009127A1 (fr) * 2006-07-18 2008-01-24 Antibe Therapeutics Inc. Dérivés de sulfure d'hydrogène d'anti-inflammatoires non stéroïdiens
WO2008020042A1 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de dérivés de 2,5-dihydroxybenzène pour le traitement de maladies de réaction tissulaire
WO2008020040A2 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de composés et de dérivés de 2,5-dihydroxybenzène pour le traitement de la fibrose
WO2008020037A1 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de dérivés de 2,5-dihydroxybenzène pour le traitement de l'obésité, de l'hirsutisme, de l'hypertricose et des verrues virales
WO2008113863A2 (fr) * 2007-03-22 2008-09-25 Action Medicines, S.L. Dérivés nitrosés de composés de 2,5-dihydroxybenzène
US7498355B2 (en) * 2005-05-27 2009-03-03 Antibe Therapeutics Inc. Derivatives of 4- or 5-aminosalicylic acid
ES2315119A1 (es) * 2006-08-16 2009-03-16 Action Medicines, S.L. Uso de derivados 2,5 -dihidrocibencenicos en la fabricacion de medicamentos y cosmeticos.
US7741359B2 (en) 2005-05-27 2010-06-22 Antibe Therapeutics Inc. Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
WO2010106082A1 (fr) * 2009-03-16 2010-09-23 Genmedica Therapeutics Sl Conjugués anti-inflammatoires et anti-oxydants utiles pour traiter des troubles métaboliques
US7910568B2 (en) 2005-05-27 2011-03-22 Antibe Therapeutics Inc. Derivatives of 4- or 5-aminosalicylic acid
US20110082192A1 (en) * 2009-10-05 2011-04-07 Milne Jill C Lipoic acid acylated salicylate derivatives and their uses
JP2011520836A (ja) * 2008-05-13 2011-07-21 ジェンメディカ・セラピューティックス・ソシエダッド・リミターダ 代謝性障害を治療するのに有用なサリチレートコンジュゲート
CN102417501A (zh) * 2011-09-02 2012-04-18 卞劲松 S-丹参素化合物、合成方法及用途
CN102961375A (zh) * 2012-12-05 2013-03-13 苏州大学 一种ampk激活剂及其在制备治疗糖尿病和/或糖尿病并发症的药物中的应用
US8466197B2 (en) 2010-12-14 2013-06-18 Genmedica Therapeutics Sl Thiocarbonates as anti-inflammatory and antioxidant compounds useful for treating metabolic disorders
CN101501018B (zh) * 2006-07-18 2014-08-27 安泰碧控股公司 非甾体抗炎药的硫化氢衍生物
US9085527B2 (en) 2008-07-08 2015-07-21 Catabasis Pharmaceuticals, Inc. Fatty acid acylated salicylates and their uses
US9139516B2 (en) 2008-07-08 2015-09-22 Catabasis Pharmaceuticals, Inc. Fatty acid acetylated salicylates and their uses
WO2020074964A1 (fr) * 2018-10-11 2020-04-16 Basf As Composés aromatiques et leurs utilisations pharmaceutiques

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5599835A (en) * 1994-11-23 1997-02-04 Fischer; Frederick B. Use of DL-lipoic acid as a medical food in the treatment of diabetes mellitus
WO2000061537A2 (fr) * 1999-04-13 2000-10-19 Nicox S.A. Composes pharmaceutiques
WO2004062598A2 (fr) * 2003-01-13 2004-07-29 Beta Pharma, Inc. Composes anti-inflammatoires et antithrombotiques et leurs compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5599835A (en) * 1994-11-23 1997-02-04 Fischer; Frederick B. Use of DL-lipoic acid as a medical food in the treatment of diabetes mellitus
WO2000061537A2 (fr) * 1999-04-13 2000-10-19 Nicox S.A. Composes pharmaceutiques
WO2004062598A2 (fr) * 2003-01-13 2004-07-29 Beta Pharma, Inc. Composes anti-inflammatoires et antithrombotiques et leurs compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DAVID E. MOLLER: "New Drug Targets for Type 2 Diabetes and the Metabolic Syndrome", NATURE., vol. 414, 13 December 2001 (2001-12-13), MACMILLAN JOURNALS LTD., LONDON, GB, pages 821 - 827, XP002341684 *

Cited By (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7498355B2 (en) * 2005-05-27 2009-03-03 Antibe Therapeutics Inc. Derivatives of 4- or 5-aminosalicylic acid
US8541398B2 (en) 2005-05-27 2013-09-24 Antibe Therapeutics Inc. Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
US8114858B2 (en) 2005-05-27 2012-02-14 Antibe Therapeutics Inc. Derivatives of 4- or 5-aminosalicylic acid
US8114857B2 (en) 2005-05-27 2012-02-14 Antibe Therapeutics Inc. Derivatives of 4- or 5-aminosalicylic acid
US7910568B2 (en) 2005-05-27 2011-03-22 Antibe Therapeutics Inc. Derivatives of 4- or 5-aminosalicylic acid
US7879827B2 (en) 2005-05-27 2011-02-01 Antibe Therapeutics Inc. Derivatives of 4- or 5-aminosalicylic acid
US7741359B2 (en) 2005-05-27 2010-06-22 Antibe Therapeutics Inc. Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
KR101450653B1 (ko) * 2006-07-18 2014-10-14 안티브 홀딩스 인크. 비스테로이드 항염증제의 황화수소 유도체
RU2468019C2 (ru) * 2006-07-18 2012-11-27 Антиб Терапьютикс Инк. Сероводородные производные нестероидных противовоспалительных лекарственных средств
NO342083B1 (no) * 2006-07-18 2018-03-19 Antibe Holdings Inc Hydrogensulfidderivater av ikke-steroide, antiinflammatoriske legemidler, deres anvendelse for fremstilling av et medikament, samt en farmasøytisk sammensetning derav
WO2008009127A1 (fr) * 2006-07-18 2008-01-24 Antibe Therapeutics Inc. Dérivés de sulfure d'hydrogène d'anti-inflammatoires non stéroïdiens
CN101501018B (zh) * 2006-07-18 2014-08-27 安泰碧控股公司 非甾体抗炎药的硫化氢衍生物
AU2007276621B2 (en) * 2006-07-18 2013-08-01 Antibe Therapeutics Inc. Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs
WO2008020042A1 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de dérivés de 2,5-dihydroxybenzène pour le traitement de maladies de réaction tissulaire
WO2008020040A3 (fr) * 2006-08-16 2008-04-10 Action Medicines Sl Utilisation de composés et de dérivés de 2,5-dihydroxybenzène pour le traitement de la fibrose
WO2008020037A1 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de dérivés de 2,5-dihydroxybenzène pour le traitement de l'obésité, de l'hirsutisme, de l'hypertricose et des verrues virales
WO2008020040A2 (fr) * 2006-08-16 2008-02-21 Action Medicines, S.L. Utilisation de composés et de dérivés de 2,5-dihydroxybenzène pour le traitement de la fibrose
ES2315119A1 (es) * 2006-08-16 2009-03-16 Action Medicines, S.L. Uso de derivados 2,5 -dihidrocibencenicos en la fabricacion de medicamentos y cosmeticos.
WO2008113863A3 (fr) * 2007-03-22 2008-12-11 Action Medicines Sl Dérivés nitrosés de composés de 2,5-dihydroxybenzène
WO2008113863A2 (fr) * 2007-03-22 2008-09-25 Action Medicines, S.L. Dérivés nitrosés de composés de 2,5-dihydroxybenzène
JP2011520836A (ja) * 2008-05-13 2011-07-21 ジェンメディカ・セラピューティックス・ソシエダッド・リミターダ 代謝性障害を治療するのに有用なサリチレートコンジュゲート
US9139516B2 (en) 2008-07-08 2015-09-22 Catabasis Pharmaceuticals, Inc. Fatty acid acetylated salicylates and their uses
US9085527B2 (en) 2008-07-08 2015-07-21 Catabasis Pharmaceuticals, Inc. Fatty acid acylated salicylates and their uses
US9708245B2 (en) 2008-07-08 2017-07-18 Catabasis Pharmaceuticals, Inc. Fatty acid acylated salicylates and their uses
US9458094B2 (en) 2008-07-08 2016-10-04 Catabasis Pharmaceuticals, Inc. Fatty acid acetylated salicylates and their uses
US9272984B2 (en) 2008-07-08 2016-03-01 Catabasis Pharmaceuticals, Inc. Fatty acid acetylated salicylates and their uses
AU2010224866C1 (en) * 2009-03-16 2015-01-15 Genmedica Therapeutics Sl Anti-inflammatory and antioxidant conjugates useful for treating metabolic disorders
US8575217B2 (en) 2009-03-16 2013-11-05 Genmedica Therapeutics Sl Anti-inflammatory and antioxidant conjugates useful for treating metabolic disorders
JP2012520342A (ja) * 2009-03-16 2012-09-06 ジェンメディカ・セラピューティックス・ソシエダッド・リミターダ 代謝障害を処置するのに有用な抗炎症剤および抗酸化剤のコンジュゲート
CN102427809B (zh) * 2009-03-16 2014-10-01 根梅迪卡治疗公司 用于治疗代谢性疾病的抗炎剂和抗氧化剂轭合物
WO2010106082A1 (fr) * 2009-03-16 2010-09-23 Genmedica Therapeutics Sl Conjugués anti-inflammatoires et anti-oxydants utiles pour traiter des troubles métaboliques
CN102427809A (zh) * 2009-03-16 2012-04-25 根梅迪卡治疗公司 用于治疗代谢性疾病的抗炎剂和抗氧化剂轭合物
AU2010224866B2 (en) * 2009-03-16 2014-03-06 Genmedica Therapeutics Sl Anti-inflammatory and antioxidant conjugates useful for treating metabolic disorders
US8946451B2 (en) * 2009-10-05 2015-02-03 Catabasis Pharmaceuticals, Inc. Lipoic acid acylated salicylate derivatives and their uses
US20110082192A1 (en) * 2009-10-05 2011-04-07 Milne Jill C Lipoic acid acylated salicylate derivatives and their uses
US8466197B2 (en) 2010-12-14 2013-06-18 Genmedica Therapeutics Sl Thiocarbonates as anti-inflammatory and antioxidant compounds useful for treating metabolic disorders
CN102417501A (zh) * 2011-09-02 2012-04-18 卞劲松 S-丹参素化合物、合成方法及用途
CN102961375B (zh) * 2012-12-05 2015-01-14 苏州大学 一种ampk激活剂及其在制备治疗糖尿病和/或糖尿病并发症的药物中的应用
WO2014086104A1 (fr) * 2012-12-05 2014-06-12 苏州大学 Activateur d'ampk et son application dans la préparation de médicaments pour le traitement du diabète et/ou de complications du diabète
CN102961375A (zh) * 2012-12-05 2013-03-13 苏州大学 一种ampk激活剂及其在制备治疗糖尿病和/或糖尿病并发症的药物中的应用
WO2020074964A1 (fr) * 2018-10-11 2020-04-16 Basf As Composés aromatiques et leurs utilisations pharmaceutiques
CN113166024A (zh) * 2018-10-11 2021-07-23 巴斯夫股份公司 芳族化合物及其医药用途

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