NZ730538B2 - Pharmaceutical composition with improved stability - Google Patents
Pharmaceutical composition with improved stabilityInfo
- Publication number
- NZ730538B2 NZ730538B2 NZ730538A NZ73053815A NZ730538B2 NZ 730538 B2 NZ730538 B2 NZ 730538B2 NZ 730538 A NZ730538 A NZ 730538A NZ 73053815 A NZ73053815 A NZ 73053815A NZ 730538 B2 NZ730538 B2 NZ 730538B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- lactide
- poly
- glycolide
- less
- weight
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims abstract 10
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 claims abstract 8
- 238000000034 method Methods 0.000 claims abstract 8
- 229920000747 poly(lactic acid) Polymers 0.000 claims abstract 7
- 229940065514 poly(lactide) Drugs 0.000 claims abstract 7
- -1 poly(lactide) Polymers 0.000 claims abstract 7
- 239000000178 monomer Substances 0.000 claims abstract 6
- 239000002253 acid Substances 0.000 claims abstract 4
- 230000000975 bioactive effect Effects 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims abstract 3
- 108010000817 Leuprolide Proteins 0.000 claims abstract 2
- 108010050144 Triptorelin Pamoate Proteins 0.000 claims abstract 2
- 238000012377 drug delivery Methods 0.000 claims abstract 2
- 239000007972 injectable composition Substances 0.000 claims abstract 2
- GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 claims abstract 2
- 229960004338 leuprorelin Drugs 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- VXKHXGOKWPXYNA-PGBVPBMZSA-N triptorelin Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 VXKHXGOKWPXYNA-PGBVPBMZSA-N 0.000 claims abstract 2
- 229960004824 triptorelin Drugs 0.000 claims abstract 2
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 claims 2
- JJTUDXZGHPGLLC-ZXZARUISSA-N (3r,6s)-3,6-dimethyl-1,4-dioxane-2,5-dione Chemical compound C[C@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-ZXZARUISSA-N 0.000 claims 1
- RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims 1
- 101150008417 LIN gene Proteins 0.000 claims 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 108010069236 Goserelin Proteins 0.000 abstract 1
- BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000013270 controlled release Methods 0.000 abstract 1
- 229960002913 goserelin Drugs 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
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
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/59—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
- A61K47/593—Polyesters, e.g. PLGA or polylactide-co-glycolide
-
- 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
- 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
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
Abstract
The present invention provides an injectable composition for controlled release drug delivery and the process of making the same, where the composition comprises: a lactate based polymer selected from poly(lactide-co-glycolide) or poly(lactide) having a weight average molecular weight between 5,000 and 50,000 dalton, an acid number of less than 3 mgKOH/g and the content of residual lactide monomers in the lactate-based polymer of less than about 0.3% by weight; a pharmaceutically acceptable organic solvent; and a bioactive substance or a salt thereof selected from leuprolide, goserelin, triptorelin, and combinations thereof in the molecular structure that is capable of reacting with lactide monomer to form a conjugate; and where the composition reduces the formation of the conjugate.
Claims (7)
1. A process for making an injectable composition for lled release drug delivery comprising: combining poly(lactide-co-glycolide) or poly(lactide) having a weight average molecular weight between 5,000 and 50,000 dalton, an acid number of less than 3 mgKOH/g and the content of residual lactide monomers in the poly(lactide-co-glycolide) or actide) of less than 0.3% by weight; with a pharmaceutically acceptable organic t; and a bioactive substance or a salt thereof that contains an amino acid serine in the molecular structure that is capable of reacting with lactide monomer to form a conjugate, wherein the bioactive substance is ed from the group consisting of leuprolide, lin, triptorelin, and combinations thereof; with the proviso that no acid additive is added in making the composition.
2. The process of claim 1 where the lactide in the poly(lactide-co-glycolide) or poly(lactide) is D-lactide, D,L-lactide, L,D-lactide, L-lactide, (R,R)-Lactide, lactide and meso-lactide or any combination thereof.
3. The process of claim 1 wherein the poly(lactide-co-glycolide) or poly(lactide) has the content of residual e monomers of less than 0.2% by weight.
4. The process of claim 1 wherein the poly(lactide-co-glycolide) or actide) has the content of residual lactide monomers of less than 0.1% by weight.
5. The process of claim 1 wherein the poly(lactide-co-glycolide) or poly(lactide) has an acid number of less than 2 mgKOH/g.
6. The process of claim 1, wherein the poly(lactide-co-glycolide) or poly(lactide) is ctide.
7. The process of claim 1, wherein the poly(lactide-co-glycolide) or poly(lactide) is poly(lactide-co-glycolide) having the ratio of lactide/glycolide from
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462064008P | 2014-10-15 | 2014-10-15 | |
| PCT/US2015/055634 WO2016061296A1 (en) | 2014-10-15 | 2015-10-15 | Pharmaceutical composition with improved stability |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ730538A NZ730538A (en) | 2024-01-26 |
| NZ730538B2 true NZ730538B2 (en) | 2024-04-30 |
Family
ID=
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