CA2176604A1 - Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin - Google Patents

Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin

Info

Publication number
CA2176604A1
CA2176604A1 CA002176604A CA2176604A CA2176604A1 CA 2176604 A1 CA2176604 A1 CA 2176604A1 CA 002176604 A CA002176604 A CA 002176604A CA 2176604 A CA2176604 A CA 2176604A CA 2176604 A1 CA2176604 A1 CA 2176604A1
Authority
CA
Canada
Prior art keywords
hydroxy
hecpt
stable formulation
ethyl camptothecin
camptothecin
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
CA002176604A
Other languages
French (fr)
Other versions
CA2176604C (en
Inventor
Kochat Haridas
Frederick Herman Hausheer
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.)
BioNumerik Pharmaceuticals Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2176604A1 publication Critical patent/CA2176604A1/en
Application granted granted Critical
Publication of CA2176604C publication Critical patent/CA2176604C/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
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/4858—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

Abstract

10-hydroxy 7-ethyl camptothecin (HECPT), an active metabolite of the camptothecin analog CPT-11, is poorly soluble in water.
Because of its poor solubility, HECPT has not been directly administered by parenteral or oral routes in human patients for the purpose of inhibiting the growth of tumors. The invention provides a pharmaceutically acceptable formulation in the form of an acidic solution or suspension comprising (1) HECPT, preponderantly in the desired lactone form (1a) and (2) dimethylisosorbide or dimethylacetamide.
CA002176604A 1993-12-22 1994-12-19 Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin Expired - Fee Related CA2176604C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US08/172,620 US5447936A (en) 1993-12-22 1993-12-22 Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin and methods for uses thereof
US08/172,620 1993-12-22
PCT/EP1994/004210 WO1995017187A1 (en) 1993-12-22 1994-12-19 Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin

Publications (2)

Publication Number Publication Date
CA2176604A1 true CA2176604A1 (en) 1995-06-29
CA2176604C CA2176604C (en) 2006-12-05

Family

ID=22628472

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002176604A Expired - Fee Related CA2176604C (en) 1993-12-22 1994-12-19 Lactone stable formulation of 10-hydroxy 7-ethyl camptothecin

Country Status (8)

Country Link
US (3) US5447936A (en)
EP (1) EP0735876B1 (en)
JP (1) JP4177890B2 (en)
AT (1) ATE202932T1 (en)
CA (1) CA2176604C (en)
DE (1) DE69427708T2 (en)
ES (1) ES2160693T3 (en)
WO (1) WO1995017187A1 (en)

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Also Published As

Publication number Publication date
ATE202932T1 (en) 2001-07-15
WO1995017187A1 (en) 1995-06-29
US5447936A (en) 1995-09-05
CA2176604C (en) 2006-12-05
ES2160693T3 (en) 2001-11-16
JPH09507056A (en) 1997-07-15
EP0735876B1 (en) 2001-07-11
DE69427708T2 (en) 2001-10-25
US5674873A (en) 1997-10-07
US5674874A (en) 1997-10-07
DE69427708D1 (en) 2001-08-16
EP0735876A1 (en) 1996-10-09
JP4177890B2 (en) 2008-11-05

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