CH680650A5 - - Google Patents
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- Publication number
- CH680650A5 CH680650A5 CH504/90A CH50490A CH680650A5 CH 680650 A5 CH680650 A5 CH 680650A5 CH 504/90 A CH504/90 A CH 504/90A CH 50490 A CH50490 A CH 50490A CH 680650 A5 CH680650 A5 CH 680650A5
- Authority
- CH
- Switzerland
- Prior art keywords
- components
- fatty acid
- weight
- cyclosporin
- acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 102
- 229960001265 ciclosporin Drugs 0.000 claims description 99
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 91
- 108010036949 Cyclosporine Proteins 0.000 claims description 89
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 80
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 73
- 229930182912 cyclosporin Natural products 0.000 claims description 73
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 68
- 239000000194 fatty acid Substances 0.000 claims description 68
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 65
- 229930195729 fatty acid Natural products 0.000 claims description 65
- 239000000047 product Substances 0.000 claims description 56
- -1 fatty acid ester Chemical class 0.000 claims description 50
- 229930105110 Cyclosporin A Natural products 0.000 claims description 49
- 150000004665 fatty acids Chemical class 0.000 claims description 41
- 235000011187 glycerol Nutrition 0.000 claims description 28
- 239000000470 constituent Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 238000005809 transesterification reaction Methods 0.000 claims description 23
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 21
- 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 claims description 21
- 239000000600 sorbitol Substances 0.000 claims description 21
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 21
- 239000008158 vegetable oil Substances 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 19
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- 230000036961 partial effect Effects 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 12
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- WMNULTDOANGXRT-UHFFFAOYSA-N bis(2-ethylhexyl) butanedioate Chemical compound CCCCC(CC)COC(=O)CCC(=O)OCC(CC)CCCC WMNULTDOANGXRT-UHFFFAOYSA-N 0.000 claims description 2
- 229920001400 block copolymer Polymers 0.000 claims description 2
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003904 phospholipids Chemical class 0.000 claims description 2
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 claims description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims 1
- 108010036941 Cyclosporins Proteins 0.000 description 24
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 14
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- 239000002285 corn oil Substances 0.000 description 13
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 12
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- 239000002609 medium Substances 0.000 description 11
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 11
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 11
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- 150000003626 triacylglycerols Chemical class 0.000 description 11
- 210000002966 serum Anatomy 0.000 description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 9
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- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 9
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- 235000021313 oleic acid Nutrition 0.000 description 9
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- 238000000034 method Methods 0.000 description 8
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 7
- OIQOAYVCKAHSEJ-UHFFFAOYSA-N 2-[2,3-bis(2-hydroxyethoxy)propoxy]ethanol;hexadecanoic acid;octadecanoic acid Chemical compound OCCOCC(OCCO)COCCO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OIQOAYVCKAHSEJ-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229910001868 water Inorganic materials 0.000 description 7
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 6
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 6
- 235000021314 Palmitic acid Nutrition 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000000787 lecithin Substances 0.000 description 6
- 235000010445 lecithin Nutrition 0.000 description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 6
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- 239000003381 stabilizer Substances 0.000 description 6
- 208000023275 Autoimmune disease Diseases 0.000 description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 5
- 206010029164 Nephrotic syndrome Diseases 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 5
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- 239000006184 cosolvent Substances 0.000 description 5
- 150000005690 diesters Chemical class 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
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- 235000020778 linoleic acid Nutrition 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 5
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- 230000000704 physical effect Effects 0.000 description 5
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 4
- 101100248253 Arabidopsis thaliana RH40 gene Proteins 0.000 description 4
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- 125000005456 glyceride group Chemical group 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
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- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 3
- NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 3
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- GEUKOOCPPICVTB-SMOCYEBVSA-N (3s,6s,9s,12r,15s,18s,21s,24s,30s)-33-[(1r,2r)-1-hydroxy-2-methylhexyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21,30-tri(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32- Chemical compound CCCC[C@@H](C)[C@@H](O)C1N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](C(C)C)NC1=O GEUKOOCPPICVTB-SMOCYEBVSA-N 0.000 description 2
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- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
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- AHQFCPOIMVMDEZ-UNISNWAASA-N (e,2s,3r,4r)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoic acid Chemical group CN[C@H](C(O)=O)[C@H](O)[C@H](C)C\C=C\C AHQFCPOIMVMDEZ-UNISNWAASA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- OVYMWJFNQQOJBU-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl octanoate Chemical compound CCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC OVYMWJFNQQOJBU-UHFFFAOYSA-N 0.000 description 1
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- 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
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Gastroenterology & Hepatology (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB898903804A GB8903804D0 (en) | 1989-02-20 | 1989-02-20 | Improvements in or relating to organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH680650A5 true CH680650A5 (sv) | 1992-10-15 |
Family
ID=10651981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH504/90A CH680650A5 (sv) | 1989-02-20 | 1990-02-16 |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPH0611703B2 (sv) |
| BE (1) | BE1005236A3 (sv) |
| CH (1) | CH680650A5 (sv) |
| CY (1) | CY1886A (sv) |
| DE (1) | DE4005190A1 (sv) |
| FR (1) | FR2643262B1 (sv) |
| GB (2) | GB8903804D0 (sv) |
| HK (1) | HK149595A (sv) |
| IT (1) | IT1240765B (sv) |
Families Citing this family (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5639724A (en) | 1984-07-24 | 1997-06-17 | Sandoz Ltd. | Cyclosporin galenic forms |
| GB8904182D0 (en) * | 1989-02-23 | 1989-04-05 | Glaxo Canada | Pharmaceutical compositions |
| HU208491B (en) * | 1990-11-27 | 1993-11-29 | Gyogyszerkutato Intezet | Process for producing oral pharmaceutical composition containing cyclosporin |
| AU688920B2 (en) * | 1991-06-27 | 1998-03-19 | Novartis Ag | Transesterified corn oil products |
| US6262022B1 (en) | 1992-06-25 | 2001-07-17 | Novartis Ag | Pharmaceutical compositions containing cyclosporin as the active agent |
| GB9113872D0 (en) * | 1991-06-27 | 1991-08-14 | Sandoz Ag | Improvements in or relating to organic compounds |
| IL102236A0 (en) * | 1991-06-27 | 1993-01-14 | Ltt Inst Co Ltd | Topical preparations containing cyclosporin |
| ES2098739T3 (es) | 1992-05-13 | 1997-05-01 | Sandoz Ltd | Composiciones oftalmicas conteniendo una cyclosporin. |
| US5759566A (en) * | 1992-07-28 | 1998-06-02 | Poli Industria Chimica Spa | Microemulsion pharmaceutical compositions for the delivery of pharmaceutically active agents |
| EP0589843B1 (en) * | 1992-09-25 | 2001-11-28 | Novartis AG | Pharmaceutical compositions containing cyclosporins |
| DE4412201A1 (de) * | 1993-04-20 | 1994-11-10 | Rentschler Arzneimittel | Neue pharmazeutische Zubereitungen zur oralen Verabreichung enthaltend Cyclosporin |
| CA2161143A1 (en) † | 1993-04-20 | 1994-10-27 | Monika Fleck | New pharmaceutical preparations comprising cyclosporin for oral administration |
| NZ247516A (en) * | 1993-04-28 | 1995-02-24 | Bernard Charles Sherman | Water dispersible pharmaceutical compositions comprising drug dissolved in solvent system comprising at least one alcohol and at least one surfactant |
| DE4322826A1 (de) * | 1993-07-08 | 1995-01-12 | Galenik Labor Freiburg Gmbh | Pharmazeutisches Präparat |
| DE4340781C3 (de) * | 1993-11-30 | 2000-01-27 | Novartis Ag | Cyclosporin enthaltende flüssige Zubereitungen und Verfahren zu ihrer Herstellung |
| WO1995022343A1 (fr) * | 1994-02-17 | 1995-08-24 | Shiseido Company, Ltd. | Composition d'emulsion a base de cyclosporine |
| US5891846A (en) * | 1994-02-17 | 1999-04-06 | Shiseido Company, Ltd. | Cyclosporin-containing emulsion composition |
| GB9405304D0 (en) * | 1994-03-16 | 1994-04-27 | Scherer Ltd R P | Delivery systems for hydrophobic drugs |
| US5474979A (en) * | 1994-05-17 | 1995-12-12 | Allergan, Inc. | Nonirritating emulsions for sensitive tissue |
| RU2158601C2 (ru) | 1994-11-03 | 2000-11-10 | Новартис Аг | Новые лекарственные формы циклоспорина для орального применения с простым составом и высокой биодоступностью и способ их получения |
| US5603951A (en) * | 1994-11-09 | 1997-02-18 | Hanmi Pharm. Ind. Co., Ltd. | Cyclosporin-containing soft capsule compositions |
| KR0167613B1 (ko) * | 1994-12-28 | 1999-01-15 | 한스 루돌프 하우스, 니콜 케르커 | 사이클로스포린-함유 연질캅셀제 조성물 |
| US5766629A (en) | 1995-08-25 | 1998-06-16 | Sangstat Medical Corporation | Oral cyclosporin formulations |
| US5962019A (en) * | 1995-08-25 | 1999-10-05 | Sangstat Medical Corporation | Oral cyclosporin formulations |
| US5834017A (en) * | 1995-08-25 | 1998-11-10 | Sangstat Medical Corporation | Oral cyclopsporin formulations |
| US5827822A (en) * | 1996-03-25 | 1998-10-27 | Sangstat Medical Corporation | Cyclosporin a formulations as nanoparticles |
| DE19549852B4 (de) | 1995-11-29 | 2009-06-04 | Novartis Ag | Cyclosporin enthaltende Präparate |
| CZ288631B6 (cs) * | 1996-01-18 | 2001-08-15 | Galena, A. S. | Léčivé přípravky s obsahem cyklosporinu |
| US5858401A (en) | 1996-01-22 | 1999-01-12 | Sidmak Laboratories, Inc. | Pharmaceutical composition for cyclosporines |
| DE29824679U1 (de) | 1997-01-30 | 2002-03-28 | Novartis Ag, Basel | Pharmazeutische Zusammensetzungen |
| WO1998040094A1 (en) * | 1997-03-12 | 1998-09-17 | Abbott Laboratories | Hydrophilic binary systems for the administration of cyclosporine |
| JP2001515491A (ja) * | 1997-03-12 | 2001-09-18 | アボツト・ラボラトリーズ | 親油性化合物の投与のための親油性二成分系 |
| ATE225174T1 (de) | 1997-07-29 | 2002-10-15 | Upjohn Co | Selbstemulgierende formulierung enthaltend saure lipophile verbindungen |
| KR100509130B1 (ko) | 1997-07-29 | 2005-08-18 | 파마시아 앤드 업존 캄파니 엘엘씨 | 친지성 화합물의 자가유화 제제 |
| US6187747B1 (en) | 1997-09-08 | 2001-02-13 | Panacea Biotech Limited | Pharmaceutical composition comprising cyclosporin |
| US6008191A (en) * | 1997-09-08 | 1999-12-28 | Panacea Biotec Limited | Pharmaceutical compositions containing cyclosporin |
| US6346511B1 (en) | 1997-09-08 | 2002-02-12 | Panacea Biotec Limited | Pharmaceutical composition comprising cyclosporin |
| US5981607A (en) * | 1998-01-20 | 1999-11-09 | Allergan | Emulsion eye drop for alleviation of dry eye related symptoms in dry eye patients and/or contact lens wearers |
| ID25908A (id) * | 1998-03-06 | 2000-11-09 | Novartis Ag | Prakonsentrat-prakonsentrat emulsi yang mengandung siklosporin atau makrolida |
| DE19859910C2 (de) * | 1998-12-23 | 2001-03-22 | Ratiopharm Gmbh | Orales Arzneimittel |
| US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| GB9912476D0 (en) | 1999-05-28 | 1999-07-28 | Novartis Ag | Organic compounds |
| AU2127400A (en) * | 1999-11-02 | 2001-05-14 | Cipla Limited | A pharmaceutical composition for the administration of water-insoluble pharmaceutically active substances and process for preparation thereof |
| GB2362573A (en) * | 2000-05-25 | 2001-11-28 | Cipla Ltd | Cyclosporin formulation |
| DK1151755T3 (da) * | 2000-05-04 | 2005-06-27 | Panacea Biotec Ltd | Farmaceutisk præparat indeholdende cyclosporin som aktiv bestanddel |
| DE10030378A1 (de) * | 2000-06-21 | 2002-03-14 | Audit Inst For Medical Service | Neue pharmazeutische Zusammensetzung zur topischen Anwendung von wasserunlöslichen und/oder schwer wasserlöslichen Wirkstoffen |
| US6979672B2 (en) | 2002-12-20 | 2005-12-27 | Polichem, S.A. | Cyclosporin-based pharmaceutical compositions |
| JP4381037B2 (ja) | 2003-06-04 | 2009-12-09 | 花王株式会社 | 油脂組成物 |
| ES2573539T3 (es) | 2005-03-21 | 2016-06-08 | Teva Czech Industries S.R.O. | Inhibidor de la cristalización y su uso en cápsulas de gelatina |
| US8492369B2 (en) | 2010-04-12 | 2013-07-23 | Clarus Therapeutics Inc | Oral testosterone ester formulations and methods of treating testosterone deficiency comprising same |
| KR20080009201A (ko) | 2005-04-15 | 2008-01-25 | 클라루스 쎄러퓨틱스, 아이엔씨. | 소수성 약물의 약물전달시스템 및 이를 포함하는 조성물 |
| FR2914188B1 (fr) * | 2007-03-28 | 2012-06-22 | Trophos | Nouvelle composition a base d'oxime de cholest-4-en-3-one |
| GB2451811A (en) | 2007-08-09 | 2009-02-18 | Ems Sa | Delivery composition for solubilising water-insoluble pharmaceutical active ingredients |
| US11304960B2 (en) | 2009-01-08 | 2022-04-19 | Chandrashekar Giliyar | Steroidal compositions |
| CA2690490C (en) * | 2010-01-19 | 2012-06-26 | Accucaps Industries Limited | Pharmaceutical formulations of loratadine for encapsulation and combinations thereof |
| US20180153904A1 (en) | 2010-11-30 | 2018-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9034858B2 (en) | 2010-11-30 | 2015-05-19 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US9358241B2 (en) | 2010-11-30 | 2016-06-07 | Lipocine Inc. | High-strength testosterone undecanoate compositions |
| US20120148675A1 (en) | 2010-12-10 | 2012-06-14 | Basawaraj Chickmath | Testosterone undecanoate compositions |
| US10894009B2 (en) | 2014-01-16 | 2021-01-19 | Maruho Co., Ltd. | Topical agent for transdermal administration |
| WO2016033549A2 (en) | 2014-08-28 | 2016-03-03 | Lipocine Inc. | (17-ß)-3-OXOANDROST-4-EN-17-YL TRIDECANOATE COMPOSITIONS AND METHODS OF THEIR PREPARATION AND USE |
| WO2016033556A1 (en) | 2014-08-28 | 2016-03-03 | Lipocine Inc. | BIOAVAILABLE SOLID STATE (17-β)-HYDROXY-4-ANDROSTEN-3-ONE ESTERS |
| US20180147215A1 (en) | 2016-11-28 | 2018-05-31 | Lipocine Inc. | Oral testosterone undecanoate therapy |
| EP3952899A1 (en) | 2019-04-11 | 2022-02-16 | R.P. Scherer Technologies, LLC | Formulation for oral delivery of proteins, peptides and small molecules with poor permeability |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2907460A1 (de) * | 1978-03-07 | 1979-09-13 | Sandoz Ag | Neue resorbierbare galenische kompositionen |
| CH641356A5 (en) * | 1979-02-27 | 1984-02-29 | Sandoz Ag | Pharmaceutical compositions containing cyclosporin |
| BE895724A (fr) * | 1982-02-01 | 1983-07-28 | Sandoz Sa | Nouvelle utilisation therapeutique de la dihydrocyclosporine d |
-
1989
- 1989-02-20 GB GB898903804A patent/GB8903804D0/en active Pending
-
1990
- 1990-02-16 GB GB9003616A patent/GB2228198B/en not_active Expired - Lifetime
- 1990-02-16 CH CH504/90A patent/CH680650A5/de not_active IP Right Cessation
- 1990-02-19 BE BE9000181A patent/BE1005236A3/fr not_active IP Right Cessation
- 1990-02-19 JP JP2038168A patent/JPH0611703B2/ja not_active Expired - Lifetime
- 1990-02-19 FR FR9002086A patent/FR2643262B1/fr not_active Expired - Lifetime
- 1990-02-19 DE DE4005190A patent/DE4005190A1/de not_active Ceased
- 1990-02-20 IT IT47650A patent/IT1240765B/it active IP Right Grant
-
1995
- 1995-09-21 HK HK149595A patent/HK149595A/xx not_active IP Right Cessation
-
1996
- 1996-04-05 CY CY188696A patent/CY1886A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE1005236A3 (fr) | 1993-06-08 |
| JPH02255623A (ja) | 1990-10-16 |
| GB9003616D0 (en) | 1990-04-11 |
| HK149595A (en) | 1995-09-29 |
| GB2228198A (en) | 1990-08-22 |
| IT9047650A0 (it) | 1990-02-20 |
| JPH0611703B2 (ja) | 1994-02-16 |
| IT9047650A1 (it) | 1990-08-21 |
| FR2643262B1 (fr) | 1993-06-11 |
| IT1240765B (it) | 1993-12-17 |
| GB8903804D0 (en) | 1989-04-05 |
| GB2228198B (en) | 1992-12-16 |
| FR2643262A1 (fr) | 1990-08-24 |
| DE4005190A1 (de) | 1990-08-23 |
| CY1886A (en) | 1996-04-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PFA | Name/firm changed |
Owner name: SANDOZ AG TRANSFER- NOVARTIS AG |
|
| PL | Patent ceased |