CA2455392A1 - Controlled release composition comprising lactic acid polymer and hydroxynaphthoic acid, and method of producing the same - Google Patents

Controlled release composition comprising lactic acid polymer and hydroxynaphthoic acid, and method of producing the same Download PDF

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Publication number
CA2455392A1
CA2455392A1 CA002455392A CA2455392A CA2455392A1 CA 2455392 A1 CA2455392 A1 CA 2455392A1 CA 002455392 A CA002455392 A CA 002455392A CA 2455392 A CA2455392 A CA 2455392A CA 2455392 A1 CA2455392 A1 CA 2455392A1
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Prior art keywords
controlled release
release composition
salt
composition according
weight
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Granted
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CA002455392A
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French (fr)
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CA2455392C (en
Inventor
Kazumichi Yamamoto
Akiko Yamada
Yoshio Hata
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Takeda Pharmaceutical Co Ltd
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/08—Peptides having 5 to 11 amino acids
    • A61K38/09—Luteinising hormone-releasing hormone [LHRH], i.e. Gonadotropin-releasing hormone [GnRH]; Related peptides
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/22—Hormones
    • A61K38/24—Follicle-stimulating hormone [FSH]; Chorionic gonadotropins, e.g. HCG; Luteinising hormone [LH]; Thyroid-stimulating hormone [TSH]
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
    • A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)
    • 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
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/06—Antiabortive agents; Labour repressants
    • 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
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • 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
    • A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
    • 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
    • A61P15/18—Feminine contraceptives
    • 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
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones

Abstract

A controlled release composition containing a physiologically active substance in high content, suppressing the initial excess release, and achieving a stable release speed over a long period of time is provided. A controlled release composition comprising (1) a physiologically active substance or salt thereof in an amount of about 14% (w/w) to about 24% (w/w) based on the total composition weight, (2) hydroxynaphthoic acid selected from the group consisting of 3-hydroxy-2-naphthoic acid and 1-hydroxy-2-naphthoic acid or salt thereof, and (3) a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5% by weight or less, wherein the molar ratio of said hydroxynaphthoic acid or salt thereof to said physiologically active substance or salt thereof is from 3:4 to 4:3.

Claims (37)

1. A controlled release composition comprising (1) a physiologically active substance or salt thereof in an amount of about 14% (w/w) to about 24% (w/w) based on the total composition weight, (2) hydroxynaphthoic acid selected from the group consisting of 3-hydroxy-2-naphthoic acid and 1-hydroxy-2-naphthoic acid or salt thereof, and (3) a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5% by weight or less, wherein the molar ratio of said hydroxynaphthoic acid or salt thereof to said physiologically active substance or salt thereof is from 3:4 to 4:3.
2. The controlled release composition according to Claim 1 wherein the lactic acid polymer has a weight-average molecular weight of 15000 to 30000.
3. The controlled release composition according to Claim 1 wherein the physiologically active substance is a LH-RH
derivative.
4. The controlled release composition according to Claim 3 wherein the LH-RH derivative is a peptide of the formula:
5-oxo-Pro-His-Trp-Ser-Tyr-Y-Leu-Arg-Pro-Z
[wherein, Y represents DLeu, DAla, DTrp, DSer(tBu), D2Nal or DHis (ImBzl), and Z represents NH-C2H5 or Gly-NH2.], or a salt thereof.

5. The controlled release composition according to Claim 1 wherein the physiologically active substance or salt thereof is a LH-RH derivative of the formula:
5-oxo-Pro-His-Trp-Ser-Tyr-DLeu-Leu-Arg-Pro-NH-C2H5 or an acetate salt thereof, and the hydroxynaphthoic acid is 3-hydroxy-2-naphthoic acid or 1-hydroxy-2-naphthoic acid.
6. A medicine comprising the controlled release composition according to Claim 1.
7. A preventive or curative drug for prostatic cancer, prostatic hyperplasia, endometriosis, uterine myoma, uterine fibroma, precocious puberty, dysmenorrhea or breast cancer or a contraceptive agent, comprising the controlled release composition according to Claim 3.
8. An agent for preventing recurrence of breast cancer after the operation for premenopausal breast cancer, which comprises the sustained-release composition according to claim 3.
9. A method of preventing or curing prostatic cancer, prostatic hyperplasia, endometriosis, uterine myoma, uterine fibroma, precocious puberty, dysmenorrhea or breast cancer or a method of contraception, comprising administrating an effective amount of the controlled release composition according to Claim 3 to mammals.
10. A method for preventing recurrence of breast cancer after the operation for premenopausal breast cancer, which comprises administering to a mammal an effective dose of the sustained-release composition according to claim 3.
11. A controlled release composition comprising a physiologically active substance or salt thereof, and a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5% by weight or less.
12. A controlled release composition comprising a physiologically active substance or salt thereof, hydroxynaphthoic acid or salt thereof, and a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5% by weight or less.
13. The controlled release composition according to Claim 11, comprising (1) a physiologically active substance or salt thereof in an amount of about 3% (w/w) to about 240 (w/w) based on the total composition weight, and (2) a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5o by weight or less.
14. The controlled release composition according to any of Claims 11 to 13 wherein the lactic acid polymer has a content of polymers having molecular weights of 3000 or less is about 1.5% by weight or less.
15. The controlled release composition according to any of Claims 11 to 13 wherein the lactic acid polymer has a content of polymers having molecular weights of 1000 or less is about 0.1% by weight or less.
16. The controlled release composition according to any of Claims 11 to 15 wherein the lactic acid polymer has a weight-average molecular weight of 15000 to 40000.
17. The controlled release composition according to any of Claims 11 to 15 wherein the lactic acid polymer has a weight-average molecular weight of 17000 to 26000.
18. The controlled release composition according to Claim 12 wherein the hydroxynaphthoic acid is 3-hydroxy-2-naphthoic acid or 1-hydroxy-2-naphthoic acid.
19. The controlled release composition according to Claim 11 or 13 wherein the physiologically active substance is a physiologically active peptide.
20. The controlled release composition according to Claim 12 wherein the physiologically active substance is a physiologically active peptide.
21. The controlled release composition according to Claim 19 wherein the physiologically active substance is a LH-RH
derivative.
22. The controlled release composition according to Claim 20 wherein the physiologically active substance is a LH-RH
derivative.
23. The controlled release composition according to Claim 21 or 22 wherein the LH-RH derivative is a peptide of the formula:

5-oxo-Pro-His-Trp-Ser-Tyr-Y-Leu-Arg-Pro-Z
[wherein, Y represents DLeu, DAla, DTrp, DSer(tBu), D2Nal or DHis (ImBzl), and Z represents NH-C2H5 or Gly-NH2.], or a salt thereof.
24. The controlled release composition according to Claim 21 wherein the LH-RH derivative or salt thereof is contained in an amount of 30 (w/w) to 24% (w/w) in the controlled release composition.
25. The controlled release composition according to Claim 22 wherein the molar ratio of the hydroxynaphthoic acid or salt thereof to the LH-RH derivative or salt thereof is from 3:4 to 4:3.
26. The controlled release composition according to Claim 22 wherein the LH-RH derivative or salt thereof is contained in an amount of 140 (w/w) to 240 (w/w) in the controlled release composition.
27. The controlled release composition according to any of Claims 11 to 13 which is used for injection.
28. A method of producing the controlled release composition according to Claim 11, comprising removing a solvent from a mixed solution of a physiologically active substance or salt thereof, and a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5% by weight or less.
29. A method of producing the controlled release composition according to Claim 12, comprising removing a solvent from a mixed solution of a physiologically active substance or salt thereof, hydroxynaphthoic acid or salt thereof, and a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5o by weight or less.
30. The method of producing a controlled release composition according to Claim 29, comprising mixing and dispersing a physiologically active substance or salt thereof into an organic solvent solution containing hydroxynaphthoic acid or salt thereof, and a lactic acid polymer or salt thereof having a weight-average molecular weight of 15000 to 50000 in which the content of polymers having molecular weights of 5000 or less is about 5% by weight or less, then, removing said organic solvent.
31. The method of producing a controlled release composition according to Claim 30 wherein the physiologically active substance or salt thereof is an aqueous solution containing a physiologically active substance or salt thereof.
32. The production method according to Claim 30 wherein the salt of a physiologically active substance is a salt with a free base or acid.
33. A medicine comprising the controlled release composition according to any of Claims 11 to 13.
34. A preventive or curative drug for prostatic cancer, prostatic hyperplasia, endometriosis, uterine myoma, uterine fibroma, precocious puberty, dysmenorrhea or breast cancer or a contraceptive agent, comprising the controlled release composition according to Claim 21 or 22.
35. An agent for preventing recurrence of breast cancer after the operation for premenopausal breast cancer, comprising the controlled release composition according to Claim 21 or 22.
36. A method of preventing or curing prostatic cancer, prostatic hyperplasia, endometriosis, uterine myoma, uterine fibroma, precocious puberty, dysmenorrhea or breast cancer or a method of contraception, comprising administrating an effective amount of the controlled release composition for mammals according to Claim 21 or 22, to mammals.
37. A method of preventing recurrence of breast cancer after the operation for premenopausal breast cancer, comprising administrating an effective amount of the controlled release composition for mammals according to Claim 21 or 22, to mammals.
CA2455392A 2001-06-29 2002-06-28 Controlled release composition comprising lactic acid polymer and hydroxynaphthoic acid, and method of producing the same Expired - Fee Related CA2455392C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
JP2001199484 2001-06-29
JP2001-199484 2001-06-29
JP2001340993 2001-11-06
JP2001-340993 2001-11-06
PCT/JP2002/006527 WO2003002092A2 (en) 2001-06-29 2002-06-28 Controlled release composition comprising lactic acid polymer and hydroxynaphthoic acid, and method of producing the same

Publications (2)

Publication Number Publication Date
CA2455392A1 true CA2455392A1 (en) 2003-01-09
CA2455392C CA2455392C (en) 2011-11-22

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CA2455392A Expired - Fee Related CA2455392C (en) 2001-06-29 2002-06-28 Controlled release composition comprising lactic acid polymer and hydroxynaphthoic acid, and method of producing the same

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US (4) US7429559B2 (en)
EP (3) EP1949936B1 (en)
JP (5) JP2003206240A (en)
KR (2) KR100916173B1 (en)
CN (3) CN100348265C (en)
AR (2) AR034641A1 (en)
AT (3) ATE387937T1 (en)
AU (2) AU2002311631B2 (en)
BR (1) BRPI0210561B8 (en)
CA (1) CA2455392C (en)
CO (1) CO5540367A2 (en)
CR (1) CR11283A (en)
CY (2) CY1105071T1 (en)
CZ (1) CZ306327B6 (en)
DE (2) DE60211464T3 (en)
DK (2) DK1949936T3 (en)
ES (2) ES2263788T5 (en)
HK (1) HK1056332A1 (en)
HU (1) HU230351B1 (en)
IL (3) IL159059A0 (en)
MX (1) MXPA03011456A (en)
MY (1) MY142066A (en)
NO (1) NO331883B1 (en)
NZ (2) NZ541884A (en)
PE (1) PE20030066A1 (en)
PL (1) PL204903B1 (en)
PT (2) PT1330293E (en)
RU (1) RU2301661C2 (en)
SG (1) SG180015A1 (en)
SI (1) SI1949936T1 (en)
SK (1) SK287577B6 (en)
TW (2) TWI332407B (en)
WO (1) WO2003002092A2 (en)
ZA (1) ZA200309152B (en)

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