CA2160692A1 - Microspheres proteiniques, vegetales, hydrolysees et modifiees; methodes de preparation et d'utilisation - Google Patents

Microspheres proteiniques, vegetales, hydrolysees et modifiees; methodes de preparation et d'utilisation

Info

Publication number: CA2160692A1
Authority: CA; Canada
Prior art keywords: composition according; vegetable protein; active agent; biologically; microsphere
Prior art date: 1993-04-22
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

Application number

CA002160692A

Other languages

English (en)

Inventor

Sam J. Milstein

Evgueni Barantsevitch

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.)

Emisphere Technologies 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.)

1993-04-22

Filing date

1994-04-22

Publication date

1994-10-27

1993-04-22 Priority claimed from US08/051,739 external-priority patent/US5401516A/en

1994-04-22 Application filed by Individual filed Critical Individual

1994-10-27 Publication of CA2160692A1 publication Critical patent/CA2160692A1/fr

Status Abandoned legal-status Critical Current

Links

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230000007017 scission Effects 0.000 description 2
239000002195 soluble material Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
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238000012546 transfer Methods 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
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244000151282 Eucalyptus cambageana Species 0.000 description 1
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240000007926 Ocimum gratissimum Species 0.000 description 1
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102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
108010039918 Polylysine Proteins 0.000 description 1
241000288906 Primates Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000019764 Soybean Meal Nutrition 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
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239000002671 adjuvant Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000005571 anion exchange chromatography Methods 0.000 description 1
239000003124 biologic agent Substances 0.000 description 1
229960003773 calcitonin (salmon synthetic) Drugs 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
238000002144 chemical decomposition reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
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238000011161 development Methods 0.000 description 1
102000038379 digestive enzymes Human genes 0.000 description 1
108091007734 digestive enzymes Proteins 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
230000007515 enzymatic degradation Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229960005051 fluostigmine Drugs 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000005484 gravity Effects 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229940047124 interferons Drugs 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
239000003055 low molecular weight heparin Substances 0.000 description 1
229940127215 low-molecular weight heparin Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
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235000011090 malic acid Nutrition 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
229940125395 oral insulin Drugs 0.000 description 1
229940126701 oral medication Drugs 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000035699 permeability Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
150000007660 quinolones Chemical class 0.000 description 1
238000011160 research Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
108010068072 salmon calcitonin Proteins 0.000 description 1
238000013341 scale-up Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
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229940124597 therapeutic agent Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229940108519 trasylol Drugs 0.000 description 1

Classifications

- 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
- A61K9/1658—Proteins, e.g. albumin, gelatin

Landscapes

Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)

CA002160692A 1993-04-22 1994-04-22 Microspheres proteiniques, vegetales, hydrolysees et modifiees; methodes de preparation et d'utilisation Abandoned CA2160692A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/051,739 US5401516A (en)	1992-12-21	1993-04-22	Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof
US051,739		1993-04-22

Publications (1)

Publication Number	Publication Date
CA2160692A1 true CA2160692A1 (fr)	1994-10-27

Family

ID=21973101

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002160692A Abandoned CA2160692A1 (fr)	1993-04-22	1994-04-22	Microspheres proteiniques, vegetales, hydrolysees et modifiees; methodes de preparation et d'utilisation

Country Status (7)

Country	Link
EP (1)	EP0696192A4 (fr)
JP (1)	JPH08509231A (fr)
AU (1)	AU6668594A (fr)
CA (1)	CA2160692A1 (fr)
WO (1)	WO1994023702A1 (fr)
ZA (1)	ZA939608B (fr)
ZW (1)	ZW17893A1 (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5667806A (en) *	1995-06-07	1997-09-16	Emisphere Technologies, Inc.	Spray drying method and apparatus
AU2595697A (en)	1996-03-29	1997-10-22	Emisphere Technologies, Inc.	Compounds and compositions for delivering active agents
US6358504B1 (en)	1997-02-07	2002-03-19	Emisphere Technologies, Inc.	Compounds and compositions for delivering active agents
DK1808438T3 (da)	1999-06-29	2014-10-27	Mannkind Corp	Rensning og stabilisering af peptid og proteiner i lægemidler
US9006175B2 (en)	1999-06-29	2015-04-14	Mannkind Corporation	Potentiation of glucose elimination
AU2003220125B2 (en)	2002-03-20	2006-06-15	Mannkind Corporation	Inhalation apparatus
PL1786784T3 (pl)	2004-08-20	2011-04-29	Mannkind Corp	Kataliza syntezy diketopiperazyn
EP2314298B1 (fr)	2004-08-23	2015-05-27	MannKind Corporation	Microparticules comprenant des sels de diketopiperazine permettant l'administration de médicaments
US20080160084A1 (en)	2004-12-22	2008-07-03	Colarome, Inc.	Natural Water-Insoluble Encapsulation Compositions and Processes for Preparing Same
AU2006290870B2 (en)	2005-09-14	2013-02-28	Mannkind Corporation	Method of drug formulation based on increasing the affinity of active agents for crystalline microparticle surfaces
DK1986679T3 (da)	2006-02-22	2017-11-20	Mannkind Corp	Fremgangsmåde til forbedring af mikropartiklers farmaceutiske egenskaber omfattende diketopiperazin og et aktivt indholdsstof
CN103252007B (zh)	2008-06-13	2016-06-22	曼金德公司	干粉吸入器和用于药物输送的系统
US8485180B2 (en)	2008-06-13	2013-07-16	Mannkind Corporation	Dry powder drug delivery system
JP5479465B2 (ja)	2008-06-20	2014-04-23	マンカインドコーポレイション	吸入努力をリアルタイムにプロファイルする対話式機器および方法
TWI614024B (zh)	2008-08-11	2018-02-11	曼凱公司	超快起作用胰島素之用途
US8314106B2 (en)	2008-12-29	2012-11-20	Mannkind Corporation	Substituted diketopiperazine analogs for use as drug delivery agents
EP2676695A3 (fr)	2009-03-11	2017-03-01	MannKind Corporation	Appareil, système et procédé de mesure de résistance d'un inhalateur
KR101875969B1 (ko)	2009-06-12	2018-07-06	맨카인드 코포레이션	한정된 비표면적을 갖는 디케토피페라진 마이크로입자
WO2011056889A1 (fr)	2009-11-03	2011-05-12	Mannkind Corporation	Appareil et méthode de simulation d'efforts d'inhalation
RU2531455C2 (ru)	2010-06-21	2014-10-20	Маннкайнд Корпорейшн	Системы и способы доставки сухих порошковых лекарств
CN105667994B (zh)	2011-04-01	2018-04-06	曼金德公司	用于药物药盒的泡罩包装
WO2012174472A1 (fr)	2011-06-17	2012-12-20	Mannkind Corporation	Microparticules de dicétopipérazine de capacité élevée
WO2013063160A1 (fr)	2011-10-24	2013-05-02	Mannkind Corporation	Procédés et compositions pour traiter la douleur
SG11201500218VA (en)	2012-07-12	2015-03-30	Mannkind Corp	Dry powder drug delivery systems and methods
EP2911690A1 (fr)	2012-10-26	2015-09-02	MannKind Corporation	Compositions et procédés de vaccin antigrippal inhalable
EP2970149B1 (fr)	2013-03-15	2019-08-21	MannKind Corporation	Compositions de dicétopipérazine microcristallines et procédés
CN105451716A (zh)	2013-07-18	2016-03-30	曼金德公司	热稳定性干粉药物组合物和方法
WO2015021064A1 (fr)	2013-08-05	2015-02-12	Mannkind Corporation	Appareil d'insufflation et procédés
US10307464B2 (en)	2014-03-28	2019-06-04	Mannkind Corporation	Use of ultrarapid acting insulin
US10561806B2 (en)	2014-10-02	2020-02-18	Mannkind Corporation	Mouthpiece cover for an inhaler

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3565559A (en) *	1968-03-11	1971-02-23	Sumitomo Chemical Co	Process for making microcapsules
JP2670680B2 (ja) *	1988-02-24	1997-10-29	株式会社ビーエムジー	生理活性物質含有ポリ乳酸系微小球およびその製造法
US5401516A (en) *	1992-12-21	1995-03-28	Emisphere Technologies, Inc.	Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof

1993
- 1993-12-22 ZA ZA939608A patent/ZA939608B/xx unknown
- 1993-12-30 ZW ZW17893A patent/ZW17893A1/xx unknown
1994
- 1994-04-22 CA CA002160692A patent/CA2160692A1/fr not_active Abandoned
- 1994-04-22 AU AU66685/94A patent/AU6668594A/en not_active Abandoned
- 1994-04-22 WO PCT/US1994/004561 patent/WO1994023702A1/fr not_active Ceased
- 1994-04-22 JP JP6523596A patent/JPH08509231A/ja active Pending
- 1994-04-22 EP EP94915419A patent/EP0696192A4/fr not_active Withdrawn

Also Published As

Publication number	Publication date
ZA939608B (en)	1994-08-24
EP0696192A1 (fr)	1996-02-14
ZW17893A1 (en)	1994-07-27
JPH08509231A (ja)	1996-10-01
WO1994023702A1 (fr)	1994-10-27
EP0696192A4 (fr)	1996-09-11
AU6668594A (en)	1994-11-08

Publication	Publication Date	Title
US5540939A (en)	1996-07-30	Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof
CA2160692A1 (fr)	1994-10-27	Microspheres proteiniques, vegetales, hydrolysees et modifiees; methodes de preparation et d'utilisation
WO1994014420A9 (fr)	1994-08-18	Microspheres de proteine vegetale hydrolysee modifiee, et leurs procedes de preparation et d'utilisation
US5451410A (en)	1995-09-19	Modified amino acids for encapsulating active agents
US5447728A (en)	1995-09-05	Desferrioxamine oral delivery system
US5811127A (en)	1998-09-22	Desferrioxamine oral delivery system
US6413550B1 (en)	2002-07-02	Proteinoid carriers and methods for preparation and use thereof
EP0630236B1 (fr)	1996-01-10	Systeme d"administration de medicaments a base de dicetopiperazine
AU626031B2 (en)	1992-07-23	New solid porous unitary form comprising micro-particles and/or nano-particles, and its preparation
US4976968A (en)	1990-12-11	Anhydrous delivery systems for pharmacological agents
US5541155A (en)	1996-07-30	Acids and acid salts and their use in delivery systems
KR100479895B1 (ko)	2005-08-04	형태학적으로균일한마이크로캡슐의제조방법및이방법에의해제조된마이크로캡슐
US5601846A (en)	1997-02-11	Proteinoid microspheres and methods for preparation and use thereof
WO1993025583A9 (fr)	1994-02-03	Proteinoides vecteurs ainsi que leurs procedes de preparation et d'utilisation
JPH08509474A (ja)	1996-10-08	経口薬剤移送組成物およびその方法
AU2004277419A1 (en)	2005-04-14	Nanoparticulate therapeutic biologically active agents
JPH0436233A (ja)	1992-02-06	生理活性物質含有生体内分解吸収性の徐放性製剤
Saez et al.	2007	Microspheres as delivery systems for the controlled release of peptides and proteins
CN1257708C (zh)	2006-05-31	改进的包埋水溶性药物或疫苗的高分子微球的制备方法
JPH08511545A (ja)	1996-12-03	プロテイノイド担体並びにその製造方法および使用方法
KR100342746B1 (ko)	2002-07-03	인슐린의 방출제어제제 및 그 방법
CN101773479A (zh)	2010-07-14	壳－核双层微球的制备方法
HU207439B (en)	1993-04-28	Method for producing micro-capsuled medicine preparations

Legal Events

Date	Code	Title	Description
2002-04-22	FZDE	Dead