CA2020818A1 - Emulsions contenant des aminopolysaccharides - Google Patents

Emulsions contenant des aminopolysaccharides

Info

Publication number: CA2020818A1
Authority: CA; Canada
Prior art keywords: delivery system; chitosan; chitosonium; delivery; active
Prior art date: 1989-07-11
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

CA 2020818

Other languages

English (en)

Inventor

George L. Ii Brode

George A. Salensky

William C. Harris, Jr.

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.)

Union Carbide Chemicals and Plastics Technology LLC

Original Assignee

Union Carbide Chemicals and Plastics Technology LLC

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.)

1989-07-11

Filing date

1990-07-10

Publication date

1991-01-12

1990-07-10 Application filed by Union Carbide Chemicals and Plastics Technology LLC filed Critical Union Carbide Chemicals and Plastics Technology LLC

1990-07-10 Priority to CA 2020818 priority Critical patent/CA2020818A1/fr

1991-01-12 Publication of CA2020818A1 publication Critical patent/CA2020818A1/fr

Status Abandoned legal-status Critical Current

Links

239000000839 emulsion Substances 0.000 title claims abstract description 22
238000012384 transportation and delivery Methods 0.000 claims abstract description 138
229920001661 Chitosan Polymers 0.000 claims abstract description 88
239000012223 aqueous fraction Substances 0.000 claims abstract description 28
229920000642 polymer Polymers 0.000 claims abstract description 26
230000001225 therapeutic effect Effects 0.000 claims abstract description 25
230000000699 topical effect Effects 0.000 claims abstract description 21
238000011282 treatment Methods 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims description 51
239000000758 substrate Substances 0.000 claims description 32
239000003085 diluting agent Substances 0.000 claims description 14
238000004458 analytical method Methods 0.000 claims description 13
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 6
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208000034423 Delivery Diseases 0.000 claims description 5
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ODHCTXKNWHHXJC-VKHMYHEASA-M 5-oxo-L-prolinate Chemical compound [O-]C(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-M 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
230000001804 emulsifying effect Effects 0.000 claims description 3
LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
229920000915 polyvinyl chloride Polymers 0.000 claims description 3
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YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 3
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 13
229910052801 chlorine Inorganic materials 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
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229920002554 vinyl polymer Polymers 0.000 description 12
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 6
125000002091 cationic group Chemical group 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
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239000004215 Carbon black (E152) Substances 0.000 description 5
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
235000019445 benzyl alcohol Nutrition 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
239000003906 humectant Substances 0.000 description 5
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150000002430 hydrocarbons Chemical class 0.000 description 5
239000002480 mineral oil Substances 0.000 description 5
235000010446 mineral oil Nutrition 0.000 description 5
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 5
150000002894 organic compounds Chemical class 0.000 description 5
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230000000717 retained effect Effects 0.000 description 5
230000009885 systemic effect Effects 0.000 description 5
238000005406 washing Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000007423 decrease Effects 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
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JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
238000009740 moulding (composite fabrication) Methods 0.000 description 4
235000001968 nicotinic acid Nutrition 0.000 description 4
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239000011664 nicotinic acid Substances 0.000 description 4
239000007764 o/w emulsion Substances 0.000 description 4
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RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
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WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 description 3
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SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
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KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
229960003495 thiamine Drugs 0.000 description 1
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AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
229960001017 tolmetin Drugs 0.000 description 1
UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
229960004880 tolnaftate Drugs 0.000 description 1
FUSNMLFNXJSCDI-UHFFFAOYSA-N tolnaftate Chemical compound C=1C=C2C=CC=CC2=CC=1OC(=S)N(C)C1=CC=CC(C)=C1 FUSNMLFNXJSCDI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
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229960001727 tretinoin Drugs 0.000 description 1
229960004319 trichloroacetic acid Drugs 0.000 description 1
229960001082 trimethoprim Drugs 0.000 description 1
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
210000003708 urethra Anatomy 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
229960003165 vancomycin Drugs 0.000 description 1
MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1
230000002792 vascular Effects 0.000 description 1
229960003636 vidarabine Drugs 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000019155 vitamin A Nutrition 0.000 description 1
239000011719 vitamin A Substances 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
235000019168 vitamin K Nutrition 0.000 description 1
239000011712 vitamin K Substances 0.000 description 1
150000003721 vitamin K derivatives Chemical class 0.000 description 1
229940045997 vitamin a Drugs 0.000 description 1
229940011671 vitamin b6 Drugs 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
229940046010 vitamin k Drugs 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
229960003414 zomepirac Drugs 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1

Landscapes

Medicinal Preparation (AREA)
Cosmetics (AREA)

CA 2020818 1989-07-11 1990-07-10 Emulsions contenant des aminopolysaccharides Abandoned CA2020818A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2020818 CA2020818A1 (fr)	1989-07-11	1990-07-10	Emulsions contenant des aminopolysaccharides

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7-379,949		1989-07-11
CA 2020818 CA2020818A1 (fr)	1989-07-11	1990-07-10	Emulsions contenant des aminopolysaccharides

Publications (1)

Publication Number	Publication Date
CA2020818A1 true CA2020818A1 (fr)	1991-01-12

Family

ID=4145447

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2020818 Abandoned CA2020818A1 (fr)	1989-07-11	1990-07-10	Emulsions contenant des aminopolysaccharides

Country Status (1)

Country	Link
CA (1)	CA2020818A1 (fr)

1990
- 1990-07-10 CA CA 2020818 patent/CA2020818A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1990-07-10	EEER	Examination request
1993-01-12	FZDE	Dead

Publication	Publication Date	Title
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AU625075B2 (en)	1992-07-02	Delivery system for pharmaceutical or therapeutic actives
US5874074A (en)	1999-02-23	Occlusive/semi-occlusive lotion for treatment of a skin disease or disorder
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DE69214768T2 (de)	1997-05-28	Felbinac enthaltendes Arzneimittel
US4997643A (en)	1991-03-05	Polymeric salt delivery systems
AU2019329007B2 (en)	2025-05-29	Semi-solid, oil-based pharmaceutical compositions containing pirfenidone for application in tissue repair
EP0725083A1 (fr)	1996-08-07	Acide hyaluronique acetyle a faible poids moleculaire, emollient, et procedes d'obtention et de purification de cet acide
JPH05310549A (ja)	1993-11-22	皮膚外用剤
JP5604792B2 (ja)	2014-10-15	外用医薬組成物
EP0408069A2 (fr)	1991-01-16	Emulsions contenant des amino-polysaccharides
JPH0624953A (ja)	1994-02-01	抗紅斑活性を持つ組成物の化粧品的使用と対応する組成物
JPH0665049A (ja)	1994-03-08	皮膚外用剤
IE59082B1 (en)	1994-01-12	Preventive drugs for elastosis
JPH10236918A (ja)	1998-09-08	皮膚貼付剤
JP3162690B2 (ja)	2001-05-08	化粧用配合物
CA2020818A1 (fr)	1991-01-12	Emulsions contenant des aminopolysaccharides
JPH11116458A (ja)	1999-04-27	皮膚外用剤組成物
JP4193016B2 (ja)	2008-12-10	皮膚外用剤
CA2020962A1 (fr)	1991-01-13	Systemes ameliores de liberation d'ingredients actifs pharmaceutiques ou therapeutiques
JPH06145037A (ja)	1994-05-24	皮膚外用剤
JP3135295B2 (ja)	2001-02-13	皮膚外用剤