EP1332128A1 - Derives benzamidine comportant un groupe sulfate, servant d'antagonistes de ltb4 - Google Patents

Derives benzamidine comportant un groupe sulfate, servant d'antagonistes de ltb4

Info

Publication number
EP1332128A1
EP1332128A1 EP01978439A EP01978439A EP1332128A1 EP 1332128 A1 EP1332128 A1 EP 1332128A1 EP 01978439 A EP01978439 A EP 01978439A EP 01978439 A EP01978439 A EP 01978439A EP 1332128 A1 EP1332128 A1 EP 1332128A1
Authority
EP
European Patent Office
Prior art keywords
group
formula
independently represent
alkyl
compounds
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Withdrawn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
EP01978439A
Other languages
German (de)
English (en)
Inventor
Ralf Anderskewitz
Kurt Schromm
Franz Birke
Hans Michael Jennewein
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Boehringer Ingelheim Pharma GmbH and Co KG
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 Boehringer Ingelheim Pharma GmbH and Co KG filed Critical Boehringer Ingelheim Pharma GmbH and Co KG
Publication of EP1332128A1 publication Critical patent/EP1332128A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/22—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to carbon atoms of six-membered aromatic rings
    • C07C305/24—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to carbon atoms of six-membered aromatic rings of non-condensed six-membered aromatic rings
    • 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
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to new sulfooxybenzamides of the formula I
  • Benzamidine derivatives are known from the prior art as active ingredients with valuable pharmaceutical properties.
  • international patent applications WO 97/21670 and WO 98/11062 disclose, inter alia, benzamidines which have free hydroxyl groups.
  • benzamidines containing sulfate groups there is no reference to benzamidines containing sulfate groups.
  • the object of the present invention is to provide new ETB 4 antagonists which, due to their LJB 4 antagonistic properties, have a wide range of possible uses in the therapeutic field.
  • the invention thus relates to sulfooxybenza ide of the general formula 1 in which
  • a J and A 2 each independently for one, optionally by one or more
  • Haloalkyl groups or Ci-Cg-alkoxy groups substituted 1,4-phenylene or
  • Z 1 and Z 2 each independently represent a group of the formula
  • R 1 is hydrogen, hydroxy, -COO-Ci-Cg-alkyl or -COO-C C 4 -alkyl-phenyl, in which in the above Group of the phenyl ring each
  • C 1 -C 4 alkyl or CC alkoxy can be substituted, R 2 and R 3 each independently of one another for a hydrogen or halogen atom, or a Ci-Cg-alkyl, C C_-haloalkyl, dC 8 alkoxy, aryl, aryloxy or
  • Aralkyl group, R 4 and R 5 each independently represent hydrogen or CC alkyl, X 1 and X 2 each independently represent -O-, -S-, -NH- or a single bond,
  • X J and X 4 each independently represent -O-, -S-, -NH- or a single bond
  • m and n each independently represent 0 or 1
  • r and s each independently represent an integer from 1 to 8
  • a 1 and A 2 each independently represent a 1,4-phenylene or 1,3-phenylene group which is optionally substituted by a C 1 -C 4 -alkyl group or C 2 -C 4 -alkenyl group,
  • Z 1 and Z 2 each independently represent a group of the formula -X 3 - (CH 2 ) S -X 4 - or a single bond,
  • R ' represents hydrogen
  • R 2 and R 3 each represent a hydrogen atom
  • R 4 and R 5 each independently represent C 1 -C 4 -alkyl
  • X 1 and X 2 each independently represent -O- or a single bond
  • X J and X 4 each independently represent -O- or a single bond
  • m and n each independently represent 0 or 1
  • r and s each independently represent an integer from 1 to 3.
  • a further preferred embodiment is the compounds of the formula I in which Z ° represents a group of the formula -CR 4 R 5 -, A 1 and A 2 each independently represent an optionally substituted by a C ⁇ -C 4 - alkyl group or C 2 -C 4 alkenyl group substituted 1,4-phenylene or 1,3-phenylene group, preferably A is 1,4-phenylene 1 and A 2 1,3-phenylene, Z 1 and Z 2 each independently represent a group of the formula -X 3 - (CH 2 ) S -X 4 -, preferably Z 1 denotes -O-CHz- and Z 2 - CH 2 -O-
  • R 1 represents hydrogen
  • R 2 and R 3 each represent a hydrogen atom
  • R 4 and R 5 each represent methyl
  • X 3 and X 4 each independently represent -O- or a single bond, m and n each represent 1, and s represents 1.
  • 1,4- -phenylene group preferably a 1,4- -phenylene group substituted by a /. -Propyl or AJlyl group,
  • Z 2 represents a single bond
  • R 1 represents hydrogen
  • R 2 and R 3 each represent a hydrogen atom
  • X 1 and X 2 are each independently -O-, m is 0, n is 1, and r 2 is.
  • CC "- alkyl and CC - alkyl generally represents a branched or unbranched hydrocarbon radical having 1 to 4 or 8 carbon atoms, which may optionally be substituted by one or more halogen atoms, preferably fluorine, which are identical to one another or can be different.
  • halogen atoms preferably fluorine
  • C 2 -C 8 alkenyl and C 2 -C 4 alkenyl generally represent a branched or unbranched unsaturated hydrocarbon radical having 2 to 4 or 8 carbon atoms, optionally with one or more halogen atoms, preferably fluorine - Can be substituted, which can be the same or different from each other.
  • the following hydrocarbon radicals may be mentioned as examples:
  • the group - (CH 2 ) r - or - (CH 2 ) S - means a branched or unbranched double-bonded hydrocarbon bridge with 1 to 8 carbon atoms, which can optionally be substituted by one or more halogen atoms, preferably fluorine, which can be the same or different from one another.
  • Aryl generally represents an aromatic radical having 6 to 10 carbon atoms, preferably phenyl, the aromatic having one or more lower alkyl group (s), lower alkenyl group (s), trifluoromethyl group (s), cyano group (s), alkoxy group (s), nitro group (n), amino group (s) and / or one or more halogen atom (s) - mutually identical or different - can be substituted;
  • the preferred aryl radical is an optionally substituted phenyl radical, halogen - such as fluorine, chlorine or bromine - and hydroxyl being preferred as substituents.
  • Alkoxy generally represents a straight-chain or branched hydrocarbon radical with 1 to 8 carbon atoms bound via an oxygen atom.
  • a lower alkoxy radical having 1 to 3 carbon atoms is preferred.
  • the methoxy group is particularly preferred.
  • Aryloxy generally represents an aromatic radical having 6 to 10 carbon atoms, preferably phenoxy, which is bonded via an oxygen, the aromatic having one or more lower alkyl group (s), lower alkenyl group (s), trifluoromethyl group (s), cyano group (s), alkoxy group ( n), nitro group (s), amino group (s) and / or one or more halogen atom (s) - mutually identical or different - can be substituted; the preferred aryl radical is an optionally substituted phenyl radical, halogen - such as fluorine, chlorine or bromine - and hydroxyl being preferred as substituents.
  • Aralkyl generally represents an aromatic radical having 6 to 10 carbon atoms, preferably phenylalkyl, bonded via an alkylene group, the aromatic group having one or more lower alkyl group (s), lower alkenyl group (s), trifluoromethyl group (s), cyano group (s), alkoxy group ( n), nitro group (s), amino group (s) and / or one or more halogen atom (s) - mutually identical or different - can be substituted; the preferred aryl radical is an optionally substituted phenyl radical, halogen - such as fluorine, chlorine or bromine - and hydroxyl being preferred as substituents.
  • the alkylene group is usually a double-bonded hydrocarbon bridge with 1 to 8 carbon atoms, preferably 1 to 3 carbon atoms, optionally with one or more
  • Halogen atom (s) - preferably fluorine - may be substituted, which may be the same or different from one another.
  • Very particularly preferred compounds are those of the formulas 1A and IB,
  • the compounds IA and IB can arise in vivo as metabolites of a corresponding LTB4-antagonistic compound with a free hydroxy group and have the following Kj values in the receptor binding test:
  • the compounds of the formula I are distinguished by a wide range of possible uses in the therapeutic field. Emphasis should be placed on those applications for which the LTB4 receptor antagonistic properties play a role.
  • the following are particularly worth mentioning: arthritis, asthma, chronic obstructive pulmonary diseases, such as chronic bronchitis, psoriasis, ulcerative colitis, gastro- or enteropathy induced by non-steroidal anti-inflammatory drugs, cystic or pulmonary fibrosis, Alzheimer's disease, shock, reperfusion damage / ischemic heart attack or stroke , Atherosclerosis, multiple sclerosis, autoimmune diseases, malignant neoplasia, alveolitis
  • the new compounds can also be used to treat diseases or conditions in which the passage of cells from the blood via the vascular endothelium into the tissue is important (for example metastasis) or diseases and conditions in which the combination of LTB4 or another active substance (for example 12-HETE) with the LTB4 receptor has an influence on cell proliferation (for example chronic mye
  • the new compounds can also be used in combination with other active ingredients, such as those used for the same indications, or e.g. With
  • Antihistamines PDE4 inhibitors, peptido-leukotriene antagonists and / or PAF-
  • Antagonists. Administration can be topical, oral, transdermal, nasal, parenteral or inhalative. Tests such as those in WO 93/16036, pp. 15 to 17, for example, are suitable for the pharmacological and biochemical investigation of the effects on the content
  • the therapeutic or prophylactic dose depends - apart from the potency of the individual compounds and the body weight of the patient - on the
  • the dose is between 10 and 500 mg, preferably between 20 and 250 mg.
  • between about 0.5 and 25, preferably between about 2 and 20 mg of active ingredient are administered to the patient.
  • Inhalation solutions generally contain between about 0.5 and 5% active ingredient.
  • the new compounds can be administered in customary preparations, for example as tablets, dragées, capsules, wafers, powders, granules, solutions, emulsions, syrups, inhalation aerosols, ointments, suppositories
  • Active ingredient according to the invention 20 parts by weight
  • the ingredients are processed in the usual way to tablets of 500 mg weight.
  • the active substance content can be increased or decreased and the amount of glucose reduced or increased accordingly.
  • Active ingredient according to the invention 100 parts by weight
  • the ingredients are processed in the usual way into suppositories weighing 1.7 g.
  • Micronized active ingredient powder (compound of the formula I; particle size approx. 0.5 to 7 ⁇ m) is filled into hard gelatin capsules in an amount of 5 mg, optionally with the addition of micronized lactose.
  • the powder is extracted from conventional inhalation devices, e.g. according to DE-A 33 45 722, to which reference is hereby made, inhaled.
  • the compounds according to the invention are prepared by methods which are known per se from the prior art. So the connections of the general Formula I can be prepared in such a way that the hydroxyl-containing benzamides of the formula II known for example from the international patent applications WO 97/21670 and WO 98/1 1062
  • X is a leaving group which can be substituted by a phenol oxygen, preferably a halogen atom, in particular chlorine, preferably in the presence of a weak base and a metal iodide.

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Pulmonology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Dermatology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Transplantation (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne de nouveaux sulfooxybenzamides de la formule (I) dans laquelle Z0 est un groupe choisi parmi les formules -X1-(CH2)r-X2- et -CR?4R5- ; A1 et A2¿ sont indépendamment l'un de l'autre des groupes 1,4-phénylène ou 1,3-phénylène éventuellements substitués par un ou plusieurs atomes halogène, des groupes C¿1?-C8-alkyl, des groupes C2-C8-alcényl, des groupes C1-C8-haloalkyl ou des groupes C1-C8-alkoxy, Z?1 et Z2¿ sont indépendamment l'un de l'autre un groupe de formule -X3-(CH2)8-X4- ou une liaison simple ; et, m et n sont indépendamment l'un de l'autre 0 ou 1, les restes R?1, R2, R3, R4, R5, X1, X2, X3, X4¿, r et s ayant la signification donnée dans le descriptif. L'invention concerne également des procédés de fabrication des composés selon l'invention, et leur utilisation en tant qu'agents pharmaceutiques, en particulier en tant qu'antagonistes de leucotriène B¿4?(LTB4).
EP01978439A 2000-10-24 2001-10-19 Derives benzamidine comportant un groupe sulfate, servant d'antagonistes de ltb4 Withdrawn EP1332128A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10052333A DE10052333A1 (de) 2000-10-24 2000-10-24 Neue Sulfooxybenzamide
DE10052333 2000-12-01
PCT/EP2001/012127 WO2002034715A1 (fr) 2000-10-24 2001-10-19 Derives benzamidine comportant un groupe sulfate, servant d'antagonistes de ltb4

Publications (1)

Publication Number Publication Date
EP1332128A1 true EP1332128A1 (fr) 2003-08-06

Family

ID=7660637

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01978439A Withdrawn EP1332128A1 (fr) 2000-10-24 2001-10-19 Derives benzamidine comportant un groupe sulfate, servant d'antagonistes de ltb4

Country Status (8)

Country Link
EP (1) EP1332128A1 (fr)
JP (1) JP3917516B2 (fr)
AU (1) AU2002210558A1 (fr)
CA (1) CA2425368C (fr)
DE (1) DE10052333A1 (fr)
MX (1) MXPA03003465A (fr)
PE (1) PE20020542A1 (fr)
WO (1) WO2002034715A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100402494C (zh) * 2005-08-25 2008-07-16 江苏吴中苏药医药开发有限责任公司 肌醇硫酸酯铝及其制备方法和口服组合物、应用

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1997491B1 (fr) * 2004-07-14 2010-09-22 Inflammation Research Center Company Ltd. Procédé d'inhibition d'une métastase de tumeur
DE602005019897D1 (de) * 2005-07-08 2010-04-22 Leopold Franzens Uni Innsbruck Verwendung von Extrakten und Inhaltsstoffen aus Leontopodium zur Steigerung der cholinergen Funktion
AU2012228755B2 (en) 2011-03-16 2017-03-23 Creative Therapeutics Gmbh Substituted diphenyl derivatives
AU2018266393A1 (en) 2017-05-12 2019-12-19 Riken Class A GPCR-binding compound modifier

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0625138B1 (fr) * 1992-02-05 1999-06-02 BOEHRINGER INGELHEIM INTERNATIONAL GmbH Nouveaux derives de l'amidine, leur fabrication et leur application en tant que medicaments ayant un effet antagoniste a ltb4
DE19546452A1 (de) * 1995-12-13 1997-06-19 Boehringer Ingelheim Kg Neue Phenylamidinderivate, Verfahren zu ihrer Herstelung und ihre Verwendung als Arzneimittel
DE19636689A1 (de) * 1996-09-10 1998-03-12 Boehringer Ingelheim Kg Neue Benzamidinderivate

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0234715A1 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100402494C (zh) * 2005-08-25 2008-07-16 江苏吴中苏药医药开发有限责任公司 肌醇硫酸酯铝及其制备方法和口服组合物、应用

Also Published As

Publication number Publication date
MXPA03003465A (es) 2004-12-06
CA2425368A1 (fr) 2003-04-08
CA2425368C (fr) 2008-12-09
AU2002210558A1 (en) 2002-05-06
JP2004512322A (ja) 2004-04-22
DE10052333A1 (de) 2002-05-02
WO2002034715A1 (fr) 2002-05-02
JP3917516B2 (ja) 2007-05-23
PE20020542A1 (es) 2002-07-16

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