CA2493391A1 - Novel thiophene glycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof - Google Patents

Novel thiophene glycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof Download PDF

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CA2493391A1
CA2493391A1 CA002493391A CA2493391A CA2493391A1 CA 2493391 A1 CA2493391 A1 CA 2493391A1 CA 002493391 A CA002493391 A CA 002493391A CA 2493391 A CA2493391 A CA 2493391A CA 2493391 A1 CA2493391 A1 CA 2493391A1
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alkyl
phenyl
alkoxy
hydrogen
replaced
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CA2493391C (en
Inventor
Heiner Glombik
Wendelin Frick
Hubert Heuer
Werner Kramer
Harm Brummerhop
Oliver Plettenburg
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Sanofi Aventis Deutschland GmbH
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Aventis Pharma Deutschland Gmbh
Heiner Glombik
Wendelin Frick
Hubert Heuer
Werner Kramer
Harm Brummerhop
Oliver Plettenburg
Sanofi-Aventis Deutschland Gmbh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • 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
    • A61P3/08—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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • 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
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • 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

Abstract

The invention relates to novel thiophenylglycoside derivatives of formula (I), where the groups have the given meanings, the physiologically-acceptable salts and methods for production thereof. The compounds are suitable as anti-diabetics for example.

Claims (17)

1. A compound of the formula I
in which R1, R2 are hydrogen, F, Cl, Br, I, OH, NO2, CN, COOH, CO(C1-C6)-alkyl, COO(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, (C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy;
HO-(C1-C8)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, phenyl, benzyl, (C1-C4)-alkylcarbonyl, where one, more than one or all hydrogen(s) in the alkyl and alkoxy radicals may be replaced by fluorine;
SO2-NH2, SO2NH(C1-C6)-alkyl, SO2N[(C1-C6)-alkyl]2, S-(C1-C6)-alkyl, S-(CH2)0-phenyl, SO-(C1-C6)-alkyl, SO-(CH2)0-phenyl, SO2-(C1-C6)-alkyl, SO2-(CH2)0-phenyl, where o may be 0-6 and the phenyl radical may be substituted up to twice by F, Cl, Br, OH, CF3, NO2, CN, OCF3, (C1-C6)-alkoxy, (C1-C6)-alkyl, NH2;
NH2, NH-(C1-C6)-alkyl, N((C1-C6)-alkyl)2, NH(C1-C7)-acyl, phenyl, O-(CH2)0-phenyl, where o may be 0-6 and where the phenyl ring may be substituted one to 3 times by F, Cl, Br, I, OH, CF3, Na2, CN, OCF3, (C1-C6)-alkoxy, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2-CH3, COOH, COO-(C1-C6)-alkyl, CONH2;
A is (C0-C15)-alkanediyl, where one or more carbon atoms in the alkanediyl radical may be replaced independently of one another by -O-, -(C=O)-, -CH=CH-, -C=C-, -S-, -CH(OH)-, -CHF-, -CF2-, -(S=O)-, -(SO2)-, -N((C1-C6)-alkyl)-, -N((C1-C6)-alkylphenyl)- or -NH-;
n is a number from 0 to 4;
Cyc1 is a 3- to 7-membered, saturated, partially saturated or unsaturated ring, where 1 carbon atom may be replaced by O or S;
R3, R4, R5 are hydrogen, F, Cl, Br, I, OH, NO2, CN, COOH, COO(C1-C6)-alkyl, CO(C1-C4)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C12)-alkoxy, HO-(C~-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, where one, more than one or all hydrogen(s) in the alkyl and alkoxy radicals may be replaced by fluorine;
SO2-NH2, SO2NH(C1-C6)-alkyl, SO2N[(C1-C6)-alkyl]2, S-(C1-C6)-alkyl, S-(CH2)0-phenyl, SO-(C1-C6)-alkyl, SO-(CH2)o-phenyl, SO2-(C1-C6)-alkyl, SO2-(CH2)o-phenyl, where o may be 0-6 and the phenyl radical may be substituted up to twice by F, Cl, Br, OH, CF3, NO2, CN, OCF3, (C1-C6)-alkoxy, (C1-C6)-alkyl, NH2;
NH2, NH-(C1-C6}-alkyl, N((C1-C6)-alkyl)2, NH(C1-C7)-acyl, phenyl, (CH2)0-phenyl, O-(CH2)0-phenyl, where o may be 0-6 and where the phenyl ring may be substituted one to 3 times by F, Cl, Br, I, OH, CF3, NO2, CN, OCF3, (C1-C8)-alkoxy, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2-CH3, COOH, COO-(C1-C6)-alkyl, CONH2;
or R3 and R4 together with the carbon atoms carrying them are a 5- to 7-membered, saturated, partially or completely unsaturated ring Cyc2, where 1 or 2 carbon atoms) in the ring may also be replaced by N, O or S, and Cyc2 may optionally be substituted by (C1-C6)-alkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyl, where in each case one CH2 group may be replaced by O, or substituted by H, F, Cl, OH, CF3, NO2, CN, COO(C1-C4)-alkyl, CONH2, CONH(C1-C4)-alkyl, OCF3, and R5 is hydrogen;
and the pharmaceutically acceptable salts thereof.
2. A compound of the formula I as claimed in claim 1, in which A is linked to the thienyl ring in position 2.
3. A compound of the formula I as claimed in claim 1 or 2, in which R1, R2 are hydrogen, F, Cl, Br, I, OH, NO2, CN, COOH, CO(C1-C6)-alkyl, COO(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C6)-alkoxy, HO-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, phenyl, benzyl, (C1-C4)-alkylcarbonyl, SO-(C1-C6)-alkyl, where one, more than one or all hydrogen(s) in the alkyl and alkoxy radicals may be replaced by fluorine;
A is (C0-C15)-alkanediyl, where one or more carbon atoms) in the alkanediyl radical may be replaced independently of one another by -O-, -(C=O)-, -CH=CH-, -C.ident.C-, -S-, -CH(OH)-, -CHF-, -CF2-, -(S=O)-, -(SO2)-, -N((C1-C6)-alkyl)-, -N((C1-C6)-alkylphenyl)- or -NH-;
n is a number 2 or 3;
Cyc1 is a 5- to 6-membered, saturated, partially saturated or unsaturated ring, where 1 carbon atom may be replaced by O or S;
R3, R4, R5 are hydrogen, F, Cl, Br, I, OH, NO2, CN, COOH, COO(C1-C6)-alkyl, CO(C1-C4)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON[(C1-C6)-alkyl]2, (C1-C8)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1-C12)-alkoxy, HO-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkylphenyl, (C1-C4)-alkoxyphenyl, S-(C1-C1)-alkyl, SO-(C1-C6)-alkyl, where one, more than one or all hydrogen(s) in the alkyl and alkoxy radicals may be replaced by fluorine;
or R3 and R4 together with the carbon atoms carrying them are a 5- to 7-membered, saturated, partially or completely unsaturated ring Cyc2, where 1 or 2 carbon atom(s) in the ring may also be replaced by N, O or S, and Cyc2 may optionally be substituted by (C1-C6)-alkyl, (C2-C5)-alkenyl, (C2-C5)-alkynyl, where in each case one CH2 group may be replaced by O, or substituted by H, F, Cl, OH, CF3, NO2, CN, COO(C1-C4)-alkyl, CONH2, CONH(C1-C4)-alkyl, OCF3, and R5 is hydrogen.
4. A compound of the formula I as claimed in claims 1 to 3, in which R1, R2 are hydrogen, (C1-C6)-alkyl, (C1-C4)-alkoxy, HO-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, F, Cl, CF3, OCF3, OCH2CF3 (C1-C4)-alkyl-CF2-, phenyl, benzyl, (C1-C4)-alkylcarbonyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, COO(C1-C4)-alkyl;
A is -CH=CH-CH2- or (C1-C4)-alkanediyl, where one or two CH2 groups may also be replaced by -(C=O)-, -CH=CH-, -CH(OH)-, -NH-, -CHF-, -CF2-, -O-, n is a number 2 or 3;
Cyc1 is unsaturated ring, where 1 carbon atom may be replaced by O or S;
R3, R4, R5 are hydrogen, F, Cl, Br, I, NO2, OH, CN, (C1-C6)-alkyl, (C1-C6)-alkoxy, OCF3, OCH2CF3, S-(C1-C4)-alkyl, COOH, HO-(C1-C4)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C2)-alkylphenyl, (C1-C2)-alkoxyphenyl, or R3 and R4 together are -CH=CH-O-, -CH=CH-S-, -O-(CH2)p-O-, with p = 1 or 2, -O-CF2-O-, -CH=CH-CH=CH-, and R5 is hydrogen.
5. A compound of the formula I as claimed in claims 1 to 4, in which R2 is hydrogen.
6. A compound of the formula I as claimed in claims 1 to 5, in which R1 is hydrogen, CF3, (C1-C4)-alkyl, phenyl, R2 is hydrogen, A is -CH2-, -C2H4-, -C3H4, -CH(OH)-, -(C=O)-, -CH=CH-, -CH=CH-CH2-, -CO-CH2-CH2- or -CO-NH-CH2-;
n is a number 2 or 3;
Cyc1 is unsaturated ring, where 1 carbon atom may be replaced by S;
R3,R4,R5 are hydrogen, F, Cl, I, NO2, OH, CN, (C1-C6)-alkyl, (C1-C8)-alkoxy, O-CH2-phenyl, OCF3, S-CH3, COOH or R3 and R4 together are -CH=CH-O-, -O-(CH2)p-O-, with p = 1 or 2, -O-CF2-O-, -CH=CH-CH=CH-, and R5 is hydrogen.
7. A compound of the formula I as claimed in claims 1 to 6, in which A is -CH2- or -CH2-CH2-.
8. A compound of the formula I as claimed in claims 1 to 7, in which Cyc1 is phenyl.
9. A compound of the formula I as claimed in claims 1 to 7, in which Cyc1 is thienyl.
10. A compound of the formula I as claimed in claims 1 to 8, in which Cyc1 is monosubstituted.
11. A medicament comprising one or more of the compounds as claimed in one or more of claims 1 to 10.
12. A medicament comprising one or more of the compounds as claimed in one or more of claims 1 to 10 and one or more blood glucose-lowering active ingredients.

67~
13. ~The use of the compounds as claimed in one or more of claims 1 to 10 for producing a medicament for the treatment of type 1 and type 2 diabetes.
14. ~The use of the compounds as claimed in one or more of claims 1 to 10 for producing a medicament for lowering blood glucose.
15. ~The use of the compounds as claimed in one or more of claims 1 to 10 in combination with at least one other blood glucose-lowering active ingredient for producing a medicament for the treatment of type 1 and type 2 diabetes.
16. ~The use of the compounds as claimed in one or more of claims 1 to 10 in combination with at least one other blood glucose-lowering active ingredient for producing a medicament for lowering blood glucose.
17. ~A process for producing a medicament comprising one or more of the compounds as claimed in one or more of claims 1 to 10, which comprises mixing the active ingredient with a pharmaceutically suitable carrier and converting this mixture into a form suitable for administration.
CA2493391A 2002-07-11 2003-06-27 Novel thiophene glycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof Expired - Fee Related CA2493391C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10231370A DE10231370B4 (en) 2002-07-11 2002-07-11 Thiophene glycoside derivatives, medicaments containing these compounds and methods of making these medicaments
DE10231370.9 2002-07-11
PCT/EP2003/006841 WO2004007517A1 (en) 2002-07-11 2003-06-27 Novel thiophenylglycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof

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CA2493391A1 true CA2493391A1 (en) 2004-01-22
CA2493391C CA2493391C (en) 2010-06-15

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US8048897B2 (en) 2004-07-26 2011-11-01 Chugai Seiyaku Kabushiki Kaisha Cyclohexane derivative, prodrug thereof and salt thereof, and therapeutic agent containing the same for diabetes

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