HUP0301742A2 - Colchinol derivatives as angiogenesis inhibitors, process for producing them, pharmaceutical compositions containing them and their use - Google Patents

Colchinol derivatives as angiogenesis inhibitors, process for producing them, pharmaceutical compositions containing them and their use

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Publication number
HUP0301742A2
HUP0301742A2 HU0301742A HUP0301742A HUP0301742A2 HU P0301742 A2 HUP0301742 A2 HU P0301742A2 HU 0301742 A HU0301742 A HU 0301742A HU P0301742 A HUP0301742 A HU P0301742A HU P0301742 A2 HUP0301742 A2 HU P0301742A2
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HU
Hungary
Prior art keywords
group
amino
alkyl
formula
hydroxyl
Prior art date
Application number
HU0301742A
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Hungarian (hu)
Inventor
Jean Claude Arnould
Original Assignee
Angiogene Pharmaceuticals Limited
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Publication date
Application filed by Angiogene Pharmaceuticals Limited filed Critical Angiogene Pharmaceuticals Limited
Publication of HUP0301742A2 publication Critical patent/HUP0301742A2/en
Publication of HUP0301742A3 publication Critical patent/HUP0301742A3/en

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    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • 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
    • 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
    • A61P3/08—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
    • A61P35/00—Antineoplastic agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Rheumatology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Endocrinology (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Obesity (AREA)
  • Ophthalmology & Optometry (AREA)
  • Reproductive Health (AREA)
  • Dermatology (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Cardiology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

A találmány (I) általános képletű vegyületekre, továbbá azokgyógyászatilag alkalmazható sóira, szolvátjaira és előgyógyszerformáira vonatkozik - a képletben R1, R2 és R3 egymástól függetlenülhidroxilcsoportot, foszforil-oxi-csoportot (-OPO3H2), 1-4 szénatomosalkoxicsoportot vagy hidroxilcsoporton képezett, in vivo körülményekközött hidrolizálható észtercsoportot jelent azzal a feltétellel, hogyR1, R2 és R3 közül legalább kettő 1-4 szénatomos alkoxicsoportotjelent; A -CO-, -C(O)O-, -CON(R8)-, -SO2- vagy -SO2N(R8)- képletűcsoportot jelent, Ra és Rb egymástól függetlenül hidrogénatomot,hidroxilcsoportot vagy aminocsoportot jelent; a értéke 1, 2, 3 vagy 4;B vegyértékkötést vagy -O-, -CO-, -N(R9)CO-, -CON(R9)-, -C(O)O-, -N(R9)-, -N(R9)C(O)O-, -N(R9)CON(R10)-, -N(R9)SO2- vagy -SO2N(R9)-képletű csoportot jelent; b értéke 0, 1, 2, 3 vagy 4, azzal afeltétellel, hogy ha b értéke 0, akkor B vegyértékkötést jelent; Dkarboxil-, szulfo-, tetrazolil-, imidazolil-, foszforil-oxi-,hidroxil-, amino-, N-(1-4 szénatomos alkil)-amino- vagy N,N-di-(1-4szénatomos alkil)-amino-csoportot vagy -Y1-(CH2)cR11 vagy -NHCH(R12)COOH képletű csoportot jelent; R5 1-4 szénatomosalkoxicsoportot jelent; R4 és R6 egymástól függetlenül hidrogén- vagyfluoratomot vagy nitro-, amino-, N-(1-4 szénatomos alkil)-amino-, N,N-di-(1-4 szénatomos alkil)-amino-, hidroxil-, 1-4 szénatomos alkoxi-vagy 1-4 szénatomos alkilcsoportot jelent; és R7 hidrogénatomot vagy1-4 szénatomos alkil-, (1-3 szénatomos alkoxi)-(1-3 szénatomosalkil)-, amino-(1-3 szénatomos alkil)- vagy hidroxi-(1-3 szénatomosalkil)-csoportot jelent. ÓThe invention relates to compounds of the general formula (I), as well as to their medicinally applicable salts, solvates and prodrug forms - in the formula, R1, R2 and R3 are independently a hydroxyl group, a phosphoryloxy group (-OPO3H2), a 1-4 carbon alkoxy group or formed on a hydroxyl group, under in vivo conditions means a hydrolyzable ester group under the condition that at least two of R1, R2 and R3 represent 1-4 carbon alkoxy groups; -CO-, -C(O)O-, -CON(R8)-, -SO2- or -SO2N(R8)- means a group of the formula, Ra and Rb independently of each other means a hydrogen atom, a hydroxyl group or an amino group; the value of a is 1, 2, 3 or 4; B is a valence bond or -O-, -CO-, -N(R9)CO-, -CON(R9)-, -C(O)O-, -N(R9)- , represents a group of the formula -N(R9)C(O)O-, -N(R9)CON(R10), -N(R9)SO2- or -SO2N(R9); b is 0, 1, 2, 3 or 4, provided that if b is 0, then B is a covalent bond; Dcarboxyl-, sulfo-, tetrazolyl-, imidazolyl-, phosphoryloxy-, hydroxyl-, amino-, N-(C1-4alkyl)amino- or N,N-di-(C1-4alkyl)amino represents a group of the formula -Y1-(CH2)cR11 or -NHCH(R12)COOH; R5 represents a C1-C4 alkoxy group; R4 and R6 are independently hydrogen or fluorine or nitro-, amino-, N-(C1-4 alkyl)amino-, N,N-di-(C1-4 alkyl)amino-, hydroxyl-, 1- represents a C4-alkyl or C1-C4 alkyl group; and R7 represents a hydrogen atom or a C1-4 alkyl, (C1-3 alkoxy)-(C1-3 alkyl), amino-(C1-3 alkyl) or hydroxy-(C1-3 alkyl) group. HE

HU0301742A 2000-07-07 2001-07-04 Colchinol derivatives as angiogenesis inhibitors, process for producing them, pharmaceutical compositions containing them and their use HUP0301742A3 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP00401976 2000-07-07
EP00401977 2000-07-07
PCT/GB2001/002964 WO2002008213A1 (en) 2000-07-07 2001-07-04 Colchinol derivatives as angiogenesis inhibitors

Publications (2)

Publication Number Publication Date
HUP0301742A2 true HUP0301742A2 (en) 2003-09-29
HUP0301742A3 HUP0301742A3 (en) 2005-08-29

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ID=26073520

Family Applications (1)

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HU0301742A HUP0301742A3 (en) 2000-07-07 2001-07-04 Colchinol derivatives as angiogenesis inhibitors, process for producing them, pharmaceutical compositions containing them and their use

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Country Link
EP (1) EP1301498A1 (en)
JP (1) JP2004504391A (en)
KR (1) KR20030022264A (en)
CN (1) CN1255392C (en)
AU (2) AU2001266232B2 (en)
BR (1) BR0112225A (en)
CA (1) CA2410562A1 (en)
CZ (1) CZ200331A3 (en)
EE (1) EE200300015A (en)
HU (1) HUP0301742A3 (en)
IL (1) IL153325A0 (en)
IS (1) IS6668A (en)
MX (1) MXPA02012903A (en)
NO (1) NO20030055D0 (en)
NZ (1) NZ522661A (en)
PL (1) PL359181A1 (en)
RU (1) RU2003103603A (en)
SK (1) SK52003A3 (en)
WO (1) WO2002008213A1 (en)

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