CA2321924A1 - Butorphanol sustained release formulations - Google Patents
Butorphanol sustained release formulations Download PDFInfo
- Publication number
- CA2321924A1 CA2321924A1 CA002321924A CA2321924A CA2321924A1 CA 2321924 A1 CA2321924 A1 CA 2321924A1 CA 002321924 A CA002321924 A CA 002321924A CA 2321924 A CA2321924 A CA 2321924A CA 2321924 A1 CA2321924 A1 CA 2321924A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- butorphanol
- oil
- hours
- concentration
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 95
- IFKLAQQSCNILHL-QHAWAJNXSA-N butorphanol Chemical compound N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 IFKLAQQSCNILHL-QHAWAJNXSA-N 0.000 title claims abstract description 68
- 229960001113 butorphanol Drugs 0.000 title claims abstract description 60
- 238000009472 formulation Methods 0.000 title abstract description 34
- 238000013268 sustained release Methods 0.000 title abstract description 10
- 239000012730 sustained-release form Substances 0.000 title abstract description 10
- 239000012458 free base Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 10
- 208000002193 Pain Diseases 0.000 claims description 21
- 239000003921 oil Substances 0.000 claims description 17
- 235000019198 oils Nutrition 0.000 claims description 17
- 230000036407 pain Effects 0.000 claims description 16
- GMTYREVWZXJPLF-AFHUBHILSA-N butorphanol D-tartrate Chemical group OC(=O)[C@@H](O)[C@H](O)C(O)=O.N1([C@@H]2CC3=CC=C(C=C3[C@@]3([C@]2(CCCC3)O)CC1)O)CC1CCC1 GMTYREVWZXJPLF-AFHUBHILSA-N 0.000 claims description 11
- -1 fatty acid ester Chemical class 0.000 claims description 11
- 229960001590 butorphanol tartrate Drugs 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 10
- 239000000194 fatty acid Substances 0.000 claims description 10
- 229930195729 fatty acid Natural products 0.000 claims description 10
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 10
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 10
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 8
- 229920000053 polysorbate 80 Polymers 0.000 claims description 8
- 239000003755 preservative agent Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000003549 soybean oil Substances 0.000 claims description 8
- 235000012424 soybean oil Nutrition 0.000 claims description 8
- 239000000375 suspending agent Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 230000002335 preservative effect Effects 0.000 claims description 7
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical group CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 6
- 238000013270 controlled release Methods 0.000 claims description 6
- 239000011859 microparticle Substances 0.000 claims description 6
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 5
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 5
- 229960002216 methylparaben Drugs 0.000 claims description 5
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 5
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 5
- 229960003415 propylparaben Drugs 0.000 claims description 5
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 4
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 4
- 229940068968 polysorbate 80 Drugs 0.000 claims description 4
- 235000019483 Peanut oil Nutrition 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 235000012343 cottonseed oil Nutrition 0.000 claims description 3
- 239000002385 cottonseed oil Substances 0.000 claims description 3
- 239000000312 peanut oil Substances 0.000 claims description 3
- 239000008159 sesame oil Substances 0.000 claims description 3
- 235000011803 sesame oil Nutrition 0.000 claims description 3
- 239000012062 aqueous buffer Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 abstract description 21
- 239000012053 oil suspension Substances 0.000 abstract description 20
- 230000007774 longterm Effects 0.000 abstract description 7
- 230000036592 analgesia Effects 0.000 abstract description 5
- 239000003814 drug Substances 0.000 description 28
- 229940079593 drug Drugs 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000725 suspension Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 241000282472 Canis lupus familiaris Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000036470 plasma concentration Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 208000000094 Chronic Pain Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 3
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 238000010268 HPLC based assay Methods 0.000 description 2
- 208000004550 Postoperative Pain Diseases 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 208000005298 acute pain Diseases 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000007979 citrate buffer Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000021474 generally recognized As safe (food) Nutrition 0.000 description 2
- 235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 229940049964 oleate Drugs 0.000 description 2
- 239000000014 opioid analgesic Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- NRJAVPSFFCBXDT-HUESYALOSA-N 1,2-distearoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC NRJAVPSFFCBXDT-HUESYALOSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 101150066284 DET2 gene Proteins 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 108010007979 Glycocholic Acid Proteins 0.000 description 1
- 208000000913 Kidney Calculi Diseases 0.000 description 1
- RFDAIACWWDREDC-UHFFFAOYSA-N Na salt-Glycocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 RFDAIACWWDREDC-UHFFFAOYSA-N 0.000 description 1
- 206010029148 Nephrolithiasis Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940090047 auto-injector Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 150000001840 cholesterol esters Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- QYIXCDOBOSTCEI-NWKZBHTNSA-N coprostanol Chemical compound C([C@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-NWKZBHTNSA-N 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000835 electrochemical detection Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 description 1
- 229940099347 glycocholic acid Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000013269 sustained drug release Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K47/02—Inorganic compounds
-
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3021798A | 1998-02-25 | 1998-02-25 | |
| US09/030,217 | 1998-02-25 | ||
| PCT/US1999/004113 WO1999043300A1 (en) | 1998-02-25 | 1999-02-25 | Butorphanol sustained release formulations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2321924A1 true CA2321924A1 (en) | 1999-09-02 |
Family
ID=21853121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002321924A Abandoned CA2321924A1 (en) | 1998-02-25 | 1999-02-25 | Butorphanol sustained release formulations |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6197344B1 (enExample) |
| EP (1) | EP1056443B1 (enExample) |
| JP (1) | JP2002504505A (enExample) |
| AT (1) | ATE265846T1 (enExample) |
| AU (1) | AU753278B2 (enExample) |
| CA (1) | CA2321924A1 (enExample) |
| DE (1) | DE69917000T2 (enExample) |
| WO (1) | WO1999043300A1 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6680067B2 (en) * | 2001-11-26 | 2004-01-20 | Oliver Yoa-Pu Hu | Controlled-release pharmaceutical preparation containing nalbuphine and a process for preparing the same |
| PL223471B1 (pl) * | 2002-03-15 | 2016-10-31 | Cypress Bioscience Inc | Kompozycja farmaceutyczna zawierająca milnacypran do stosowania w leczeniu zespołu nadwrażliwości jelita grubego |
| AU2003272601B2 (en) * | 2002-09-20 | 2009-05-07 | Alpharma Pharmaceuticals, Llc | Sustained-release opioid formulations and methods of use |
| US20060003004A1 (en) * | 2002-10-25 | 2006-01-05 | Collegium Pharmaceutical, Inc. | Pulsatile release compositions of milnacipran |
| US20040132826A1 (en) * | 2002-10-25 | 2004-07-08 | Collegium Pharmaceutical, Inc. | Modified release compositions of milnacipran |
| US20040228830A1 (en) * | 2003-01-28 | 2004-11-18 | Collegium Pharmaceutical, Inc. | Multiparticulate compositions of milnacipran for oral administration |
| RU2254852C1 (ru) * | 2004-01-23 | 2005-06-27 | Ефим Давыдович Нежинский | Раствор для инъекций, обладающий выраженным анальгетическим действием, и способ его получения |
| WO2008106571A2 (en) * | 2007-02-28 | 2008-09-04 | Abbott Laboratories | Sustained release parenteral formulations of buprenorphine |
| CA2816420C (en) * | 2010-10-29 | 2018-01-16 | Najib Babul | Compositions of (-)-17-(cyclobutylmethyl)morphinan-3,14-diol |
| TW201618783A (zh) | 2014-08-07 | 2016-06-01 | 艾森塔製藥公司 | 以布魯頓(Bruton)氏酪胺酸激酶(BTK)佔據和BTK再合成速率為基礎之治療癌症、免疫和自體免疫疾病及發炎性疾病之方法 |
| US11234974B2 (en) | 2015-05-28 | 2022-02-01 | Lumosa Therapeutics Co., Ltd. | Pharmaceutical formulations for sustained release of sebacoyl dinalbuphine ester |
| CN106376232B (zh) | 2015-05-28 | 2021-06-11 | 顺天医药生技股份有限公司 | 用于持续释放癸二酰二纳布啡酯的药物制剂 |
| US10183018B2 (en) | 2015-05-28 | 2019-01-22 | Lumosa Therapeutics Co., Ltd. | Pharmaceutical formulations for sustained release of sebacoyl dinalbuphine ester |
| CN111904928A (zh) * | 2019-05-07 | 2020-11-10 | 江苏恒瑞医药股份有限公司 | 一种包含布托啡诺的可注射的药物组合物及其制备方法 |
| CN116818928B (zh) * | 2023-04-28 | 2024-04-19 | 杭州沐源生物医药科技有限公司 | 一种酒石酸布托啡诺注射液中杂质的分离检测方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE788478A (fr) | 1971-09-08 | 1973-03-06 | Bristol Myers Co | Procede de preparation de composes analgesiques |
| CA1098444A (en) * | 1975-05-26 | 1981-03-31 | Leo Geller | Peptide preparations with prolonged action |
| US4338324A (en) * | 1981-03-17 | 1982-07-06 | Mcneilab, Inc. | Analgesic potentiation |
| US4322427A (en) | 1981-04-16 | 1982-03-30 | Bristol-Myers Company | Analgetic compositions and methods of use |
| US4464378A (en) * | 1981-04-28 | 1984-08-07 | University Of Kentucky Research Foundation | Method of administering narcotic antagonists and analgesics and novel dosage forms containing same |
| AU614527B2 (en) * | 1987-07-24 | 1991-09-05 | Nexstar Pharmaceuticals, Inc. | Opioid analgesic liposomal delivery-release system |
| FR2663223B1 (fr) * | 1990-06-14 | 1994-12-02 | Af Aplicaciones Far Lab | Forme galenique parenterale. |
| US5478577A (en) * | 1993-11-23 | 1995-12-26 | Euroceltique, S.A. | Method of treating pain by administering 24 hour oral opioid formulations exhibiting rapid rate of initial rise of plasma drug level |
| GB9202464D0 (en) * | 1992-02-05 | 1992-03-18 | Danbiosyst Uk | Composition for nasal administration |
| GB9226905D0 (en) * | 1992-12-24 | 1993-02-17 | Wellcome Found | Pharmaceutical preparation |
| JP2596255Y2 (ja) | 1993-03-23 | 1999-06-07 | ナカミチ株式会社 | ディスク再生装置 |
| DE69603577T2 (de) | 1995-02-10 | 1999-11-25 | Medtronic, Inc. | Verfahren und vorrichtung zur verabreichung von analgetika |
| TW487572B (en) * | 1996-05-20 | 2002-05-21 | Janssen Pharmaceutica Nv | Aqueous suspensions of 9-hydroxyrisperidone fatty acid esters |
-
1999
- 1999-02-25 WO PCT/US1999/004113 patent/WO1999043300A1/en not_active Ceased
- 1999-02-25 AT AT99936027T patent/ATE265846T1/de not_active IP Right Cessation
- 1999-02-25 CA CA002321924A patent/CA2321924A1/en not_active Abandoned
- 1999-02-25 DE DE69917000T patent/DE69917000T2/de not_active Expired - Fee Related
- 1999-02-25 AU AU33112/99A patent/AU753278B2/en not_active Ceased
- 1999-02-25 JP JP2000533099A patent/JP2002504505A/ja active Pending
- 1999-02-25 EP EP99936027A patent/EP1056443B1/en not_active Expired - Lifetime
- 1999-10-28 US US09/429,391 patent/US6197344B1/en not_active Expired - Fee Related
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| Publication number | Publication date |
|---|---|
| WO1999043300A1 (en) | 1999-09-02 |
| JP2002504505A (ja) | 2002-02-12 |
| AU753278B2 (en) | 2002-10-10 |
| EP1056443A1 (en) | 2000-12-06 |
| EP1056443B1 (en) | 2004-05-06 |
| ATE265846T1 (de) | 2004-05-15 |
| DE69917000T2 (de) | 2005-04-21 |
| US6197344B1 (en) | 2001-03-06 |
| DE69917000D1 (de) | 2004-06-09 |
| AU3311299A (en) | 1999-09-15 |
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