EP1404322A2 - Derives de 1-acide butane, preparations pharmaceutiques comportant ces derives et utilisations de ces derives - Google Patents

Derives de 1-acide butane, preparations pharmaceutiques comportant ces derives et utilisations de ces derives

Info

Publication number
EP1404322A2
EP1404322A2 EP02750523A EP02750523A EP1404322A2 EP 1404322 A2 EP1404322 A2 EP 1404322A2 EP 02750523 A EP02750523 A EP 02750523A EP 02750523 A EP02750523 A EP 02750523A EP 1404322 A2 EP1404322 A2 EP 1404322A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
aryl
cycloalkyl
clδ
compound
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.)
Withdrawn
Application number
EP02750523A
Other languages
German (de)
English (en)
Inventor
Erich Eigenbrodt
Stefan Müllner
Sybille Mazurek
Hugo Fasold
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.)
ScheBo Biotech AG
Original Assignee
ScheBo Biotech AG
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 ScheBo Biotech AG filed Critical ScheBo Biotech AG
Publication of EP1404322A2 publication Critical patent/EP1404322A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • 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
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • 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
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • 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
    • A61K31/275—Nitriles; Isonitriles
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/401—Proline; Derivatives thereof, e.g. captopril
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
    • A61K31/6615—Compounds having two or more esterified phosphorus acid groups, e.g. inositol triphosphate, phytic acid
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7024—Esters of saccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock

Definitions

  • 1-butanoic acid derivatives pharmaceutical compositions containing such derivatives and uses of such derivatives.
  • the invention relates to butanoic acid derivatives, pharmaceutical compositions containing such derivatives and uses of such derivatives for the production of pharmaceutical compositions for the treatment of various diseases.
  • Cancer is one of the leading causes of death these days and the number of cancer cases in industrialized countries is constantly increasing. This is mainly due to the fact that malignant tumors are a disease of old age and, thanks to the successful fight against infectious diseases, more people are reaching this age. Despite all the advances in the diagnostic and therapeutic fields, the prospects for a cure for the most common internal cancer forms are rarely over 20%. A cancerous growth can currently be destroyed or inhibited in its growth. A regression of a tumor cell into a normal cell cannot yet be achieved. The main therapeutic measures, surgery and radiation, remove cancer cells from the body. The cancer chemotherapeutics currently in use, the cytostatics, only lead to the destruction or damage of tumor cells. The effect is in the in most cases so little specific that serious damage to healthy cells occurs at the same time.
  • tumor cells have a • different metabolism, in particular glycolysis, from healthy cells.
  • a change in the isoenzyme system involved in glycolysis and a change in the transport of NADH is typical for tumor cells.
  • Et al the activity of the enzymes of glycolysis is increased. This also allows high sales under the aerobic conditions typical of tumor cells.
  • E. Eigenbrodt et al. Biochemical an Molecular Aspects of Selected Cancers, Vol. 2, pp. 311 ff., 1994.
  • the present invention is based on the technical problem of specifying active substances which are able to inhibit the proliferation of cancer cells and thus the growth of neoplastic tumors, as well as excessive ones
  • the invention teaches the use of a compound of formula I.
  • a and b can be the same or different 'and values of 0 or 1.
  • R -H, Cl-Cl ⁇ alkyl, cycloalkyl or aryl
  • R2 -0X1 ,. -SX1, -COO " , - (CH 2 ) n -COOXl or.
  • a pharmaceutical composition for the treatment and / or prophylaxis of diseases from the group consisting of "neoplastic tumors, inflammatory diseases, autoimmune diseases, degenerative joint diseases, diseases of the rheumatic type with cartilage degradation, chronic polyarthritis, joint trauma, immobilization-related cartilage loss , septic shock, diseases with impaired leukocyte adhesion, diseases caused by increased TNFalpha concentrations, cachexia, Crohn's disease, rejection reactions after Tr ⁇ implantation ".
  • the invention teaches a pharmaceutical composition containing a compound of formula I.
  • At least one physiologically compatible auxiliary and / or carrier substance at least one physiologically compatible auxiliary and / or carrier substance.
  • alkyl includes linear and branched alkyl groups.
  • cycloalkyl also includes cycloalkyl groups with linear or branched alkyl substituents.
  • aryl also includes aralkyl groups, where alkyl substituents can be alkyl or cycloalkyl.
  • a pharmaceutical composition according to the invention can contain several different compounds falling under the above definitions.
  • a pharmaceutical composition according to the invention can additionally contain an active ingredient different from the compound of the formula I. Then it is a combination product.
  • the various active ingredients used can be prepared in a single dosage form, i.e. the active ingredients are: mixed in the dosage form.
  • Rl -H, methyl or ethyl
  • Counter ions for ionic compounds according to formula I are Na + , K +, Li +, cycloheylammmonium, or basic amino acids (for example lysine, argini, ornithine, glutanin).
  • compositions prepared with the inventive compounds may be administered orally, intramuscularly, periarticularly, intraarticularly, 'administered intravenously, intraperitoneally, subcutaneously, or rectally.
  • the invention relates to processes for the production of medicaments, which are characterized in that at least one compound of the formula I is brought into a suitable administration form with a pharmaceutically suitable and physiologically compatible carrier and, if appropriate, other suitable active ingredients, additives or auxiliaries.
  • Suitable solid or liquid pharmaceutical preparation forms are, for example, granules, powders, dragees, tablets, (micro) capsules, suppositories, syrups, juices, suspensions, emulsions, drops or injectable solutions and preparations with a protracted Active ingredient release, in the production of which conventional auxiliaries such as carriers, disintegrants, binders, coatings, quelants, lubricants or lubricants, flavors, sweeteners and solubilizers are used.
  • conventional auxiliaries such as carriers, disintegrants, binders, coatings, quelants, lubricants or lubricants, flavors, sweeteners and solubilizers are used.
  • Auxiliaries include magnesium carbonate, titanium dioxide, lactose, mannitol and other sugars, talc, milk protein, gelatin, starch, cellulose and its derivatives, animal and vegetable oils such as cod liver oil, sunflower, peanut or sesame oil, polyethylene glycols and solvents such as sterile water and mono- or polyhydric alcohols, e.g. Called glycerin.
  • the medicaments are preferably produced and administered in dosage units, each unit containing as active ingredient a certain dose of the compound of the formula I according to the invention.
  • this dose can be 1 to 1000 mg, preferably 50 to 300 mg, and in the case of injection solutions in ampoule form 0.3 to 300 mg, preferably 10 to 100 mg.
  • Daily doses of 20 to 1000 mg of active ingredient, preferably 100 to 500 mg, are indicated for the treatment of an adult patient weighing 50 to 100 kg, for example 70 kg. Under certain circumstances, however, higher or lower daily doses may also be appropriate.
  • the daily dose can be administered either by single administration in the form of a single dosage unit or else several smaller dosage units, or by multiple administration of divided doses at certain intervals. The invention is explained in more detail below on the basis of examples which merely illustrate embodiments.
  • the Novikof f-hepatoma cells used came from the tumor bank of the German Cancer Research Center,
  • L-cycloserine or dehydrothreonine was dissolved in a solvent suitable for use in cell cultures, such as. B. Water, dil. Ethanol, dimethyl sulfoxide or the like a. , added to the culture medium in increasing concentration, e.g. B. L-cycloserine (Compound 16) or dehydrothreonine (Compound 2) in the concentration range from 80uM - 5000 ⁇ M; Carbomethoxypropionyl cyanide (Compound 13) from 100 ⁇ M - 300 ⁇ M). After four days of cultivation, the number of cells per bottle was counted. The results are shown in FIGS. 1 and 2 and a dose-dependent inhibition of proliferation can be seen in comparison to the control sample without adding a compound according to the invention.
  • CMPC carbomethoxypropionyl cyanide

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Pain & Pain Management (AREA)
  • Diabetes (AREA)
  • Transplantation (AREA)
  • Dermatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux dérivés d'acide butane contenant un groupe cyanure, des préparations pharmaceutiques comportant des dérivés d'acide butane et des utilisations de dérivés d'acide butane dans la production de préparations pharmaceutiques destinées au traitement de diverses maladies.
EP02750523A 2001-03-13 2002-03-12 Derives de 1-acide butane, preparations pharmaceutiques comportant ces derives et utilisations de ces derives Withdrawn EP1404322A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10112924 2001-03-13
DE10112924A DE10112924A1 (de) 2001-03-13 2001-03-13 1-Butansäurederivate, pharmazeutische Zusammensetzungen enthaltend solche Derivate und Verwendungen solcher Derivate
PCT/DE2002/000922 WO2002072534A2 (fr) 2001-03-13 2002-03-12 Derives de 1-acide butane, preparations pharmaceutiques comportant ces derives et utilisations de ces derives

Publications (1)

Publication Number Publication Date
EP1404322A2 true EP1404322A2 (fr) 2004-04-07

Family

ID=7677848

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02750523A Withdrawn EP1404322A2 (fr) 2001-03-13 2002-03-12 Derives de 1-acide butane, preparations pharmaceutiques comportant ces derives et utilisations de ces derives

Country Status (7)

Country Link
US (2) US20040266873A1 (fr)
EP (1) EP1404322A2 (fr)
JP (1) JP2004525126A (fr)
AU (1) AU2002308369A1 (fr)
CA (1) CA2458479A1 (fr)
DE (1) DE10112924A1 (fr)
WO (1) WO2002072534A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10112925A1 (de) * 2001-03-13 2002-10-02 Erich Eigenbrodt Verwendung von Zuckerphosphaten, Zuckerphosphatanalogen, Aminosäuren, Aminosäureanalogen zur Modulation von Transaminasen und/oder der Assoziation p36/Malat Dehydrogenase
WO2006024492A2 (fr) * 2004-08-30 2006-03-09 Interstitial Therapeutics Implant medical comprenant des inhibiteurs de la synthese atp

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1091089A (en) * 1965-08-20 1967-11-15 Pierre Wirth Organic base salts of n-carbamyl-aspartic acids
US6090414A (en) * 1970-05-20 2000-07-18 Life Science Labs, Inc. Method and composition to reduce cancer incidence
FR2315916A2 (fr) * 1976-03-23 1977-01-28 Univ Johns Hopkins Melanges therapeutiques comprenant des analogues alpha hydroxy acides d'acides amines essentiels et leur administration a l'homme en vue de l'amelioration de la synthese proteique et la suppression de la formation d'uree
GB2127809B (en) * 1982-09-28 1986-03-12 Ciba Geigy Ag Certain b-oxo-a-carbamoyl-pyrrolepropionitriles
US5200526A (en) * 1987-04-27 1993-04-06 The Governors Of The University Of Alberta Syntheses of optically pure α-amino acids from 3-amino-2-oxetanone salts
JPH06256184A (ja) * 1993-03-05 1994-09-13 Morishita Roussel Kk 癌患者用アミノ酸製剤
DE19610955A1 (de) * 1996-03-20 1997-09-25 Hoechst Ag Kombinationspräparat, enthaltend 5-Methylisoxazol-4-carbonsäure-(4-trifluormethyl)- anilid und N-(4-Trifluormethylphenyl)-2-cyan-3- hydroxycrotonsäureamid
US5885786A (en) * 1996-04-19 1999-03-23 John Wayne Cancer Institute Methods for screening of substances for inhibition of multidrug resistance
HUP9602024A3 (en) * 1996-07-25 1999-05-28 Toth Sandor Pharmaceutical composition containing aminoacid for external use
MXPA00010150A (es) * 1998-04-17 2002-05-14 Parker Hughes Inst Inhibidores de btk y metodos para su identificacion y uso.
DE19857009A1 (de) * 1998-12-10 2000-06-15 Aventis Pharma Gmbh Zubereitung mit verbesserter therapeutischer Breite, enthaltend Nukleotidsyntheseinhibitoren

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02072534A2 *

Also Published As

Publication number Publication date
AU2002308369A1 (en) 2002-09-24
US20040266873A1 (en) 2004-12-30
WO2002072534A2 (fr) 2002-09-19
CA2458479A1 (fr) 2002-09-19
WO2002072534A3 (fr) 2003-08-28
JP2004525126A (ja) 2004-08-19
US20100256230A1 (en) 2010-10-07
DE10112924A1 (de) 2002-10-02

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