CA2174961A1 - Desferrioxamine oral delivery system - Google Patents
Desferrioxamine oral delivery systemInfo
- Publication number
- CA2174961A1 CA2174961A1 CA002174961A CA2174961A CA2174961A1 CA 2174961 A1 CA2174961 A1 CA 2174961A1 CA 002174961 A CA002174961 A CA 002174961A CA 2174961 A CA2174961 A CA 2174961A CA 2174961 A1 CA2174961 A1 CA 2174961A1
- Authority
- CA
- Canada
- Prior art keywords
- composition
- amino acids
- amino acid
- active agent
- phenylalanine
- 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.)
- Granted
Links
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/28—Compounds containing heavy metals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
- A61K31/727—Heparin; Heparan
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/19—Cytokines; Lymphokines; Interferons
- A61K38/21—Interferons [IFN]
- A61K38/212—IFN-alpha
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- 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
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- A—HUMAN NECESSITIES
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- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
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- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
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- 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
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- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/167—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction with an outer layer or coating comprising drug; with chemically bound drugs or non-active substances on their surface
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/84—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
Abstract
Modified amino acids and methods for their preparation and use as oral delivery systems for pharmaceutical agents are described.
The modified amino acids are preparable by reacting single amino acids or mixtures of two or more kinds of amino acids with an amino modifying agent such as benzene sulfonyl chloride, benzoyl chloride, and hippuryl chloride. The modified amino acids may form encapsulating microspheres in the presence of the active agent under sphere-forming conditions. Alternatively, the modified amino acids may be used as a carrier by simply mixing the amino acids with the active agent. The preferred acylated amino acid carrier is salicyloyl-phenylalanine. The modified amino acids are particularly useful in delivering biologically active agents, e.g., desferrioxamine, insulin or cromolyn sodium, or other agents which are sensitive to the denaturing conditions of the gastrointestinal tract.
The modified amino acids are preparable by reacting single amino acids or mixtures of two or more kinds of amino acids with an amino modifying agent such as benzene sulfonyl chloride, benzoyl chloride, and hippuryl chloride. The modified amino acids may form encapsulating microspheres in the presence of the active agent under sphere-forming conditions. Alternatively, the modified amino acids may be used as a carrier by simply mixing the amino acids with the active agent. The preferred acylated amino acid carrier is salicyloyl-phenylalanine. The modified amino acids are particularly useful in delivering biologically active agents, e.g., desferrioxamine, insulin or cromolyn sodium, or other agents which are sensitive to the denaturing conditions of the gastrointestinal tract.
Claims (23)
1. A composition of matter comprising (a) an biologically active agent selected from the group consisting of desferrioxamine, insulin and cromolyn sodium; and (b) an acylated amino acid carrier.
2. The composition as defined in claim 1 wherein said biologically active agent is desferrioxamine.
3. The composition as defined in claim 1 wherein said biologically active agent is insulin.
4. The composition as defined in claim 1 wherein said biologically active agent is cromolyn sodium.
5. The composition as defined in claim 1 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
6. The composition as defined in claim 2 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
7. The composition as defined in claim 3 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
8. The composition as defined in claim 4 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
9. A pharmaceutical composition comprising;
(a) a biologically active agent selected from the group consisting of desferrioxamine, insulin and cromolyn sodium;
(b) an acylated amino acid carrier; and (c) a pharmaceutically acceptable carrier or diluent.
(a) a biologically active agent selected from the group consisting of desferrioxamine, insulin and cromolyn sodium;
(b) an acylated amino acid carrier; and (c) a pharmaceutically acceptable carrier or diluent.
10. The pharmaceutical composition as defined in claim 9 wherein said biologically active agent is desferrioxamine.
11. The pharmaceutical composition as defined in claim 9 wherein said biologically active agent is insulin.
12. The pharmaceutical composition as defined in claim 9 wherein said biologically active agent is cromolyn sodium.
13. The pharmaceutical composition as defined in claim 9 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
14. The pharmaceutical composition as defined in claim 10 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
15. The pharmaceutical composition as defined in claim 11 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
16. The pharmaceutical composition as defined in claim 12 wherein said acylated amino acid carrier comprises salicyloyl-phenylalanine.
17. A method of lowering iron concentration in a mammal comprising orally administering a composition as defined in claim 2.
18. A method of lowering iron concentration in a mammal comprising orally administering a composition as defined in claim 6.
19. A method of treating diabetes in a mammal in need of such treatment comprising orally administering a composition as defined in claim 3.
20. A method of treating diabetes in a mammal in need of such treatment comprising orally administering a composition as defined in claim 7.
21. A method of treating respiratory afflictions in a mammal in need of such treatment comprising orally administering a composition as defined in claim 4.
22. A method of treating respiratory afflictions in a mammal in need of such treatment comprising orally administering a composition as defined in claim 8.
23. A dosage unit form comprising (A) a pharmacological composition as defined in claim 9; and (B) (a) an excipient, (b) a diluent, (c) a disintegrant, (d) a lubricant, (e) a plasticizer, (f) a colorant, (g) a dosing vehicle, or (h) any combination thereof.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14357193A | 1993-10-26 | 1993-10-26 | |
US08/143,571 | 1993-10-26 | ||
US08/168,776 US5447728A (en) | 1992-06-15 | 1993-12-16 | Desferrioxamine oral delivery system |
US08/168,776 | 1993-12-16 | ||
PCT/US1994/012333 WO1995011690A1 (en) | 1993-10-26 | 1994-10-24 | Desferrioxamine oral delivery system |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2174961A1 true CA2174961A1 (en) | 1995-05-04 |
CA2174961C CA2174961C (en) | 2011-05-03 |
Family
ID=26841181
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2174961A Expired - Lifetime CA2174961C (en) | 1993-10-26 | 1994-10-24 | Desferrioxamine oral delivery system |
Country Status (10)
Country | Link |
---|---|
US (1) | US5447728A (en) |
EP (2) | EP0726771B1 (en) |
JP (1) | JPH09504300A (en) |
AT (2) | ATE286383T1 (en) |
AU (1) | AU8093694A (en) |
CA (1) | CA2174961C (en) |
DE (2) | DE69434224T2 (en) |
ES (2) | ES2234487T3 (en) |
IL (1) | IL111385A0 (en) |
WO (1) | WO1995011690A1 (en) |
Families Citing this family (91)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6099856A (en) | 1992-06-15 | 2000-08-08 | Emisphere Technologies, Inc. | Active agent transport systems |
US5714167A (en) | 1992-06-15 | 1998-02-03 | Emisphere Technologies, Inc. | Active agent transport systems |
US6344213B1 (en) | 1996-03-29 | 2002-02-05 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
US5693338A (en) | 1994-09-29 | 1997-12-02 | Emisphere Technologies, Inc. | Diketopiperazine-based delivery systems |
US5578323A (en) | 1992-06-15 | 1996-11-26 | Emisphere Technologies, Inc. | Proteinoid carriers and methods for preparation and use thereof |
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EP1025840B1 (en) * | 1993-04-22 | 2005-06-29 | Emisphere Technologies, Inc. | Oral drug compositions |
-
1993
- 1993-12-16 US US08/168,776 patent/US5447728A/en not_active Expired - Lifetime
-
1994
- 1994-10-24 AT AT00117452T patent/ATE286383T1/en not_active IP Right Cessation
- 1994-10-24 DE DE69434224T patent/DE69434224T2/en not_active Expired - Fee Related
- 1994-10-24 JP JP7512827A patent/JPH09504300A/en not_active Ceased
- 1994-10-24 EP EP94932077A patent/EP0726771B1/en not_active Expired - Lifetime
- 1994-10-24 IL IL11138594A patent/IL111385A0/en unknown
- 1994-10-24 ES ES00117452T patent/ES2234487T3/en not_active Expired - Lifetime
- 1994-10-24 ES ES94932077T patent/ES2171471T3/en not_active Expired - Lifetime
- 1994-10-24 AU AU80936/94A patent/AU8093694A/en not_active Abandoned
- 1994-10-24 WO PCT/US1994/012333 patent/WO1995011690A1/en active IP Right Grant
- 1994-10-24 AT AT94932077T patent/ATE212186T1/en active
- 1994-10-24 EP EP00117452A patent/EP1072255B8/en not_active Expired - Lifetime
- 1994-10-24 DE DE69429729T patent/DE69429729T2/en not_active Expired - Fee Related
- 1994-10-24 CA CA2174961A patent/CA2174961C/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
ATE286383T1 (en) | 2005-01-15 |
EP1072255B1 (en) | 2005-01-05 |
DE69429729T2 (en) | 2002-08-14 |
DE69434224T2 (en) | 2005-08-25 |
EP1072255B8 (en) | 2005-04-13 |
EP1072255A2 (en) | 2001-01-31 |
EP0726771A1 (en) | 1996-08-21 |
US5447728A (en) | 1995-09-05 |
AU8093694A (en) | 1995-05-22 |
ES2234487T3 (en) | 2005-07-01 |
DE69429729D1 (en) | 2002-03-14 |
ATE212186T1 (en) | 2002-02-15 |
DE69434224D1 (en) | 2005-02-10 |
EP0726771A4 (en) | 1997-01-29 |
EP1072255A3 (en) | 2001-09-26 |
ES2171471T3 (en) | 2002-09-16 |
IL111385A0 (en) | 1994-12-29 |
JPH09504300A (en) | 1997-04-28 |
EP0726771B1 (en) | 2002-01-23 |
CA2174961C (en) | 2011-05-03 |
WO1995011690A1 (en) | 1995-05-04 |
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