CA2382886A1 - Benzamide formulation with histone deacetylase inhibitor activity - Google Patents

Benzamide formulation with histone deacetylase inhibitor activity Download PDF

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Publication number
CA2382886A1
CA2382886A1 CA002382886A CA2382886A CA2382886A1 CA 2382886 A1 CA2382886 A1 CA 2382886A1 CA 002382886 A CA002382886 A CA 002382886A CA 2382886 A CA2382886 A CA 2382886A CA 2382886 A1 CA2382886 A1 CA 2382886A1
Authority
CA
Canada
Prior art keywords
pharmaceutically acceptable
histone deacetylase
benzamide
injections
prepared
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.)
Granted
Application number
CA002382886A
Other languages
French (fr)
Other versions
CA2382886C (en
Inventor
Masahiko Ishibashi
Masahiro Sakabe
Ikuo Sakai
Tsuneji Suzuki
Tomoyuki Ando
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.)
Bayer Pharma AG
Original Assignee
Schering Aktiengesellschaft
Masahiko Ishibashi
Masahiro Sakabe
Ikuo Sakai
Tsuneji Suzuki
Tomoyuki Ando
Bayer Schering Pharma Aktiengesellschaft
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 Schering Aktiengesellschaft, Masahiko Ishibashi, Masahiro Sakabe, Ikuo Sakai, Tsuneji Suzuki, Tomoyuki Ando, Bayer Schering Pharma Aktiengesellschaft filed Critical Schering Aktiengesellschaft
Publication of CA2382886A1 publication Critical patent/CA2382886A1/en
Application granted granted Critical
Publication of CA2382886C publication Critical patent/CA2382886C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Transplantation (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

There are provided pharmaceutical formulations with improved oral absorptivity and injections that contain, as active ingredients, high concentrations of benzamide derivatives and their pharmaceutically acceptable salts, which are useful as histone deacetylase inhibitors. A pharmaceutical solution is prepared by dissolving a benzamide derivative or a pharmaceutically acceptable salt thereof in an organic solvent and/or acidic liquid, and a pharmaceutical formulation is prepared by adding a surfactant, an acidic substance and/or a polyethylene glycol. The present invention has enabled dissolution of benzamide derivatives or their pharmaceutically acceptable salts at high concentrations, to prepare practical injections and oral liquid formulations and improve absorptivity with oral administration.
CA002382886A 1999-08-30 2000-08-29 Benzamide formulation with histone deacetylase inhibitor activity Expired - Fee Related CA2382886C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP11/242444 1999-08-30
JP24244499A JP2001081031A (en) 1999-08-30 1999-08-30 Benzamide derivative-containing preparation having improved solubility and oral adsorption
PCT/EP2000/008421 WO2001016106A1 (en) 1999-08-30 2000-08-29 Benzamide formulation with histone deacetylase inhibitor activity

Publications (2)

Publication Number Publication Date
CA2382886A1 true CA2382886A1 (en) 2001-03-08
CA2382886C CA2382886C (en) 2009-06-09

Family

ID=17089193

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002382886A Expired - Fee Related CA2382886C (en) 1999-08-30 2000-08-29 Benzamide formulation with histone deacetylase inhibitor activity

Country Status (32)

Country Link
US (1) US6638530B1 (en)
EP (1) EP1208086B1 (en)
JP (2) JP2001081031A (en)
KR (1) KR100712640B1 (en)
CN (1) CN1147472C (en)
AR (1) AR025434A1 (en)
AT (1) ATE318258T1 (en)
AU (1) AU773617B2 (en)
BG (1) BG65544B1 (en)
BR (1) BR0013648A (en)
CA (1) CA2382886C (en)
CZ (1) CZ301737B6 (en)
DE (1) DE60026144T2 (en)
DK (1) DK1208086T3 (en)
EE (1) EE05063B1 (en)
ES (1) ES2259289T3 (en)
HK (1) HK1046277B (en)
HR (1) HRP20020182B1 (en)
HU (1) HUP0203330A3 (en)
IL (2) IL148357A0 (en)
MX (1) MXPA02002090A (en)
NO (1) NO322532B1 (en)
NZ (1) NZ517520A (en)
PL (1) PL201274B1 (en)
PT (1) PT1208086E (en)
RU (1) RU2260428C2 (en)
SI (1) SI1208086T1 (en)
SK (1) SK287252B6 (en)
TW (1) TWI268778B (en)
UA (1) UA72541C2 (en)
WO (1) WO2001016106A1 (en)
ZA (1) ZA200201424B (en)

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US8119159B2 (en) * 1999-02-22 2012-02-21 Merrion Research Iii Limited Solid oral dosage form containing an enhancer
EP1374855A1 (en) * 2001-03-30 2004-01-02 Takeda Chemical Industries, Ltd. Medicinal solutions
US6897220B2 (en) 2001-09-14 2005-05-24 Methylgene, Inc. Inhibitors of histone deacetylase
US7868204B2 (en) 2001-09-14 2011-01-11 Methylgene Inc. Inhibitors of histone deacetylase
AU2006252047B2 (en) * 2001-09-14 2010-02-11 Methylgene Inc. Inhibitors of histone deacetylase
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US6706686B2 (en) 2001-09-27 2004-03-16 The Regents Of The University Of Colorado Inhibition of histone deacetylase as a treatment for cardiac hypertrophy
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WO2003070691A1 (en) * 2002-02-21 2003-08-28 Osaka Industrial Promotion Organization N-hydroxycarboxamide derivative
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JP2006520796A (en) 2003-03-17 2006-09-14 タケダ サン ディエゴ インコーポレイテッド Histone deacetylase inhibitor
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EP1663953A1 (en) * 2003-09-24 2006-06-07 Methylgene, Inc. Inhibitors of histone deacetylase
JP5107579B2 (en) 2003-12-02 2012-12-26 ザ オハイオ ステート ユニバーシティー リサーチ ファウンデーション Zn2 + chelate motif tethered short chain fatty acids as a novel class of histone deacetylase inhibitors
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US7604939B2 (en) * 2005-03-01 2009-10-20 The Regents Of The University Of Michigan Methods of identifying active BRM expression-promoting HDAC inhibitors
US20100087328A1 (en) * 2005-03-01 2010-04-08 The Regents Of The University Of Michigan Brm expression and related diagnostics
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Also Published As

Publication number Publication date
AU773617B2 (en) 2004-05-27
BG65544B1 (en) 2008-11-28
KR100712640B1 (en) 2007-05-02
CN1147472C (en) 2004-04-28
SI1208086T1 (en) 2006-08-31
EP1208086A1 (en) 2002-05-29
EE05063B1 (en) 2008-08-15
KR20020023424A (en) 2002-03-28
ZA200201424B (en) 2002-11-27
JP2003508386A (en) 2003-03-04
PT1208086E (en) 2006-07-31
AR025434A1 (en) 2002-11-27
CA2382886C (en) 2009-06-09
DE60026144T2 (en) 2006-11-16
CZ301737B6 (en) 2010-06-09
PL201274B1 (en) 2009-03-31
MXPA02002090A (en) 2003-08-20
SK2612002A3 (en) 2002-09-10
NO20020952L (en) 2002-03-20
EP1208086B1 (en) 2006-02-22
HRP20020182B1 (en) 2007-08-31
ES2259289T3 (en) 2006-10-01
HK1046277A1 (en) 2003-01-03
NO20020952D0 (en) 2002-02-27
WO2001016106A1 (en) 2001-03-08
TWI268778B (en) 2006-12-21
DK1208086T3 (en) 2006-06-19
JP2001081031A (en) 2001-03-27
ATE318258T1 (en) 2006-03-15
IL148357A0 (en) 2002-09-12
NO322532B1 (en) 2006-10-23
RU2260428C2 (en) 2005-09-20
DE60026144D1 (en) 2006-04-27
BG106439A (en) 2002-11-29
EE200200097A (en) 2003-04-15
IL148357A (en) 2006-12-10
HUP0203330A2 (en) 2003-02-28
SK287252B6 (en) 2010-04-07
NZ517520A (en) 2003-05-30
AU6841600A (en) 2001-03-26
HRP20020182A2 (en) 2004-02-29
HUP0203330A3 (en) 2004-03-01
BR0013648A (en) 2002-05-07
PL353063A1 (en) 2003-10-06
UA72541C2 (en) 2005-03-15
US6638530B1 (en) 2003-10-28
HK1046277B (en) 2004-11-26
CZ2002724A3 (en) 2002-07-17
CN1371366A (en) 2002-09-25

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