SE445174B - Farmaceutisk komposition innehallande en cyklosporin och en berarsubstans - Google Patents
Farmaceutisk komposition innehallande en cyklosporin och en berarsubstansInfo
- Publication number
- SE445174B SE445174B SE7901683A SE7901683A SE445174B SE 445174 B SE445174 B SE 445174B SE 7901683 A SE7901683 A SE 7901683A SE 7901683 A SE7901683 A SE 7901683A SE 445174 B SE445174 B SE 445174B
- Authority
- SE
- Sweden
- Prior art keywords
- cyclosporin
- weight
- parts
- composition according
- oil
- Prior art date
Links
- 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 title claims description 24
- 108010036949 Cyclosporine Proteins 0.000 title claims description 24
- 229960001265 ciclosporin Drugs 0.000 title claims description 24
- 229930105110 Cyclosporin A Natural products 0.000 title claims description 22
- 229930182912 cyclosporin Natural products 0.000 title claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 239000000126 substance Substances 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 4
- 235000019198 oils Nutrition 0.000 claims description 4
- 239000002285 corn oil Substances 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 108010040786 dihydrocyclosporin C Proteins 0.000 claims description 3
- 239000004006 olive oil Substances 0.000 claims description 3
- 235000008390 olive oil Nutrition 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims 2
- 240000007817 Olea europaea Species 0.000 claims 1
- 229920001515 polyalkylene glycol Polymers 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 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 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 108010036941 Cyclosporins Proteins 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000004698 lymphocyte Anatomy 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000035622 drinking Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229940104230 thymidine Drugs 0.000 description 2
- 235000019489 Almond oil Nutrition 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- 108010062580 Concanavalin A Proteins 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241001149960 Tolypocladium inflatum Species 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 210000004989 spleen cell Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 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
- A61K47/06—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
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1274—Non-vesicle bilayer structures, e.g. liquid crystals, tubules, cubic phases or cochleates; Sponge phases
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dispersion Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Medicinal Preparation (AREA)
Description
7901683-8
... w
w _
van?
ä På
2 »SW
Fä _
fl/ \ val?
(iso-cyklosporin D)
_
w
2 zí
mlmlwL
F".
2 wßw
u whm \ _
m\ u w mß
(cyklosporin A)
(dihydro-cyklosporin C)
10
15
20
25
30
35
7901683-8
l:
Cyklosporin A, dihydrocyklosporin C och isocyklosporin D är de föredragna
cyklosporinerna.
De under a) angivna icke-joniska estrarna kan framställas på i och för sig
i känt sätt, t.ex. som beskrivs i US-PS 3 288 824. Estrarna kan vara transesteri-
fieringsprodukter av tvâ moldelar av en naturlig olja, såsom majsolja, mandelolja,
jordnötsolja, olivolja och/eller palmolja, med en moldel polyetylenglykol med en
molekylvikt på 200 till 800. Sådana estrar finns i handeln under namnet
LABRAFIL (se Fiedler, Lexikon der Hilfstoffe, sid. 320, 1971) och framställs
exempelvis av Lab. Gattefosse, Boulogne sur Seine, Franrike. Den föredragna
- estern får man ur omättad naturlig olja; föredragen är exempelvis en triglycer-
idoleat-polyetylen-blandning, som finns i handeln under namnet LABRAFIL M
191m CS.
Den föredragna totalkoncentrationen av komponenterna liksom vikt~
förhållandet mellan de enskilda komponenterna beror bl.a. på de speciellt
använda komponenterna och särskilt på deras löslighetseffekt och även på den
använda cyklosporinen och cyklosporinens koncentration i den slutgiltiga kom-
positionen.
I allmänhet använder man per lO viktdelar av komponent a) 0,2 till 10
delar av cyklosporinen, särskilt l till 10 delar av cyklosporinen och företrädesvis
I till 7 delar av cyklosporinen.
Viktandelen etanol kan exempelvis uppgå till 2 till 596 för parenterala
kompositioner och l till 20% för kompositioner för oral tillförsel, i vardera fallet
räknat pä hela kompositionen.
Viktandelen av växtoljan kan exempelvis uppgå till 35 till 6096 räknat på
totalkompositionen.
Om en av komponenterna är fast vid rumstemperatur, skall man för
framställning av kompositionerna använda temperaturer upp till ca 70°C för att
få en flytande smälta, i vilken den aktiva substansen kan lösas. Därefter kyls
kompositionerna, varefter de exempelvis mals.
Komponenterna b) och c) kan t.ex. vara närvarande i koncentrationer upp
till 60% av totalkompositionen för att man skall uppnå en tillfredsställande
koncentration av cyklosporinen.
Egenskaperna hos kompositionen enligt uppfinningen kan bestämmas på i
och för sig känt sätt. Lösningarnas stabilitet, särskilt mot utkristallisation av den
aktiva substansen, kan fastställas med användning av kända tester. Fördragbar-
heten för tillförselformerna kan fastställas enligt kända fördragbarhetstester.
Absorptionen av cyklosporinerna, särskilt det snabba inträdandet av en
tillfredsställande koncentration av cyklosporinen-i blodet och den höga totalab-
sorptionen av cyklosporinen under 21+ timmar, fastställs med användning av
lO
15
20
25
30
35
7901683-8
standardtester.
Vid ett test tillförs en farmaceutisk komposition enligt föreliggande
uppfinning till kaniner, råttor, hundar eller rhesusapor oral t, intramuskulärt eller
subkutant i en dos av 2-600 mg av cyklosporinen per kg djurvikt. Blodserumprov
och urinprov tas med regelbundna tidsintervall, exempelvis varje timme, och den
däri ingående peptidkoncentrationen bestäms på i och för sig känt sätt.
Den farmakodynamiska aktiviteten för cyklosporinen kan bestämmas påi
och för sig känt sätt. I fallet cyklosporin A kan peptidens verkan fastställas
genom hämning av lymfocytproliferationen. För detta uppsamlas blodserumet
med regelbundna tidsintervall efter tillförsel av substansen och tillsätts i en
koncentration av 0,3 till 10% in vitro till en mjältcellsuspenson från mus, där
lymfocytproliferationen utlöses genom concanavalin A under en 72 timmars
odlingsperiod. BH-tymidin tillsätts sedan och efter 24 timmar mäts tymidinin-
byggnaden för bestämning av lymfocytproliferationen.
Om så önskas kan peptiden tillföras i radioaktiv form. Exempelvis kan
man i ett experiment tillföra l00 mg BH-märkt cyklosporin A (framställt genom
fermentering av den kända svampstammen Tolypocladium inflatum Gams NRRL
8044 i närvaro av metionin märkt med tritium i SCHB-gruppen), som befinner sig
i en farmaceutisk komposition enligt föreliggande uppfinning, oralt i form av en
dricklösning eller en kapsel, eller intramuskulärt i form av en injektionslösning
till Beagle-hundar av hankön. Blodprov tas från varje hund var 15:e minut efter
tillförseln upp till en timme efter tillförseln och sedan varje timme upp till 8
timmar efter tillförseln. Urinen uppsamlas likaså. Bestämning av radioaktivite-
ten i blodet och i urinen anger peptidabsorptionen.
Mängden av den cyklosporin som skall tillföras i den farmaceutiska
kompositionen enligt föreliggande uppfinning beror givetvis på tillförselsättet,
den önskade effekten och behandlingsbetingelserna.
l allmänhet kommer andelen av den med hjälp av den farmaceutiska
kompositionen enligt föreliggande uppfinning tillförda cyklosporinen att vara av
samma storleksordning som den cyklosporin som tillförs på något annat sätt.
De mängder som erfordras för att man skall uppnå en terapeutisk verkan
är kända. Om man använder kompositioner enligt föreliggande uppfinning, skall
en daglig dos av 3 mg/kg till 50 mg/kg cyklosporiner tillföras för behandling av
kroniska inflammationer och för att man skall uppnå en immunosuppressiv effekt.
Det efterföljande exemplet beskriver uppfinningen.
Exempel: Dricklösning
200 mg cyklosporin A löses direkt under omrörning i l ml blandning av
"Labrafil M 191m CS" och etanol (i förhållandet 40:15) vid ZSOC, och efter tillsats
Claims (7)
10 15 20 25 30 7901683-8 6 av 0,1; ml olivolja eller majsolja filtreras den erhållna lösningen och fylls på små flaskor. Lösningen innehåller per 10 víktdelar "Labrafil" 3 viktdelar cyklosporin A, 3 viktdelar etanol och 5 viktdelar oliv- eller majsolja. PATENTKRAV l. Farmaceutisk komposition innehållande en cyklosporin och en bärar- substans, k ä n n e t e ck n a d av att bärarsubstansen består av följande komponenter: a) en icke-jonisk transesterífieringsprodukt av en oljetriglycerid och en polyalkylenglykol, b) en växtol ja, och c) etanol.
2. Komposítion enligt patentkravet l, k ä n n e t e c k n a d av att cyklosporinen är cyklosporin A och/eller dihydro- cyklosporin C och/eller isocyklosporin D.
3. Komposition enligt patentkravet 1, k ä n n e t e c k n a d av att den under a) angivna komponenten erhållits genom omíörestring av två moldelar naturlig olja med en moldel polyetylenglykol med en molekylvikt från 200 till 800.
4. Komposition enligt något av de föregående patentkraven, k ä n n e t e c k n a d av att den per 10 viktdelar av komponenten a) innehåller 0,2 till l0 delar cyklosporin.
5. Komposition enligt något av de föregående patentkraven, k å n n e t e c k n a d av att den innehåller komponenterna b) och c) tillsammans i en viktandel upp till 60% med avseende på hela kombinationen.
6. i Komposition enligtnågot av de föregående patentkraven, k ä n n e t e c k n a d av att den innehåller komponenten b) i en viktandel från 35 till 60% med avseende på hela kombinationen.
7. Komposition enligt något av de föregående patentkraven, k ä n n e t e c k n a d av att den innehåller komponenten c) i en viktandel från l till 2096 med avseende på hela kombinationen.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH246178A CH636013A5 (en) | 1978-03-07 | 1978-03-07 | More readily absorbable pharmaceutical composition |
| CH863478 | 1978-08-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7901683L SE7901683L (sv) | 1979-09-08 |
| SE445174B true SE445174B (sv) | 1986-06-09 |
Family
ID=25690510
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7901683A SE445174B (sv) | 1978-03-07 | 1979-02-26 | Farmaceutisk komposition innehallande en cyklosporin och en berarsubstans |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4388307A (sv) |
| JP (1) | JPS54132223A (sv) |
| AR (1) | AR223667A1 (sv) |
| AT (1) | AT375828B (sv) |
| AU (1) | AU528714B2 (sv) |
| CA (1) | CA1139667A (sv) |
| CY (1) | CY1285A (sv) |
| DD (1) | DD142149A5 (sv) |
| DE (1) | DE2907460A1 (sv) |
| DK (1) | DK154539C (sv) |
| ES (1) | ES478295A1 (sv) |
| FI (1) | FI65914C (sv) |
| FR (1) | FR2419072A1 (sv) |
| GB (1) | GB2015339B (sv) |
| HK (1) | HK48585A (sv) |
| IE (1) | IE48016B1 (sv) |
| IL (1) | IL56790A (sv) |
| IT (1) | IT1115038B (sv) |
| KE (1) | KE3516A (sv) |
| MY (1) | MY8500134A (sv) |
| NL (2) | NL187260C (sv) |
| NO (2) | NO152635C (sv) |
| NZ (1) | NZ189819A (sv) |
| PH (1) | PH15159A (sv) |
| PT (1) | PT69309A (sv) |
| SE (1) | SE445174B (sv) |
| SG (1) | SG14785G (sv) |
Families Citing this family (155)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE54936B1 (en) * | 1980-02-14 | 1990-03-28 | Sandoz Ltd | A method for the total synthesis of cyclosporins, novel cyclosporins and novel intermediates and methods for their production |
| DE3224619A1 (de) * | 1981-07-14 | 1983-05-19 | Freund Industrial Co., Ltd., Tokyo | Orale pharmazeutische zusammensetzung |
| US4525339A (en) * | 1982-10-15 | 1985-06-25 | Hoffmann-La Roche Inc. | Enteric coated oral dosage form |
| EP0127426A1 (en) * | 1983-05-23 | 1984-12-05 | Takeda Chemical Industries, Ltd. | Percutaneous pharmaceutical compositions for external use |
| US5639724A (en) | 1984-07-24 | 1997-06-17 | Sandoz Ltd. | Cyclosporin galenic forms |
| GB8903804D0 (en) * | 1989-02-20 | 1989-04-05 | Sandoz Ltd | Improvements in or relating to organic compounds |
| US5411951A (en) * | 1984-10-04 | 1995-05-02 | Monsanto Company | Prolonged release of biologically active somatotropin |
| US5474980A (en) * | 1984-10-04 | 1995-12-12 | Monsanto Company | Prolonged release of biologically active somatotropins |
| US4727035A (en) * | 1984-11-14 | 1988-02-23 | Mahoney Walter C | Immunoassay for cyclosporin |
| US4576645A (en) * | 1984-12-06 | 1986-03-18 | Block Drug Co., Inc. | Whipped gel composition |
| JPS61280435A (ja) * | 1985-04-04 | 1986-12-11 | Kanji Takada | サイクロスポリン類のリンパ指向性製剤 |
| US4775659A (en) * | 1985-08-19 | 1988-10-04 | Eli Lilly And Company | Injectable semi-solid formulations |
| GB8524421D0 (en) * | 1985-10-03 | 1985-11-06 | Boots Co Plc | Therapeutic agents |
| US4764381A (en) * | 1985-12-06 | 1988-08-16 | Key Pharmaceuticals, Inc. | Percutaneous penetration enhancer of oleic acid and 2-ethyl-1, 3-hexanediol |
| ATE80295T1 (de) * | 1986-05-02 | 1992-09-15 | Brigham & Womens Hospital | Fettsaeure und cyclosporin enthaltende zusammensetzung mit ermaessigter nephrotoxizitaet. |
| US5118493A (en) * | 1986-05-02 | 1992-06-02 | Brigham And Women's Hospital | Composition having reduced nephrotoxocity comprising a fatty acid containing component and cyclosporine |
| KR880012221A (ko) * | 1987-04-13 | 1988-11-26 | 사노 가즈오 | 에스테르 또는 아미드를 활성성분으로 함유하는 약제 조성물 |
| JP2577049B2 (ja) * | 1987-06-04 | 1997-01-29 | 三共株式会社 | シクロスポリン製剤 |
| GB8717300D0 (en) * | 1987-07-22 | 1987-08-26 | Nat Res Dev | Cyclosporins |
| US4839342A (en) * | 1987-09-03 | 1989-06-13 | University Of Georgia Research Foundation, Inc. | Method of increasing tear production by topical administration of cyclosporin |
| AU620048B2 (en) * | 1987-09-03 | 1992-02-13 | University Of Georgia Research Foundation, Inc., The | Ocular cyclosporin composition |
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1979
- 1979-02-26 FI FI790640A patent/FI65914C/fi not_active IP Right Cessation
- 1979-02-26 SE SE7901683A patent/SE445174B/sv not_active IP Right Cessation
- 1979-02-26 DE DE19792907460 patent/DE2907460A1/de active Granted
- 1979-02-27 FR FR7904989A patent/FR2419072A1/fr active Granted
- 1979-02-27 NO NO790661A patent/NO152635C/no unknown
- 1979-02-27 IT IT48152/79A patent/IT1115038B/it active Protection Beyond IP Right Term
- 1979-02-28 DK DK086079A patent/DK154539C/da not_active IP Right Cessation
- 1979-03-02 CY CY1285A patent/CY1285A/xx unknown
- 1979-03-02 NL NLAANVRAGE7901703,A patent/NL187260C/xx active Protection Beyond IP Right Term
- 1979-03-02 GB GB7907395A patent/GB2015339B/en not_active Expired
- 1979-03-05 AT AT0163779A patent/AT375828B/de not_active IP Right Cessation
- 1979-03-05 NZ NZ189819A patent/NZ189819A/en unknown
- 1979-03-05 PT PT69309A patent/PT69309A/pt unknown
- 1979-03-05 ES ES478295A patent/ES478295A1/es not_active Expired
- 1979-03-05 IL IL56790A patent/IL56790A/xx unknown
- 1979-03-06 CA CA000322853A patent/CA1139667A/en not_active Expired
- 1979-03-06 DD DD79211409A patent/DD142149A5/de not_active IP Right Cessation
- 1979-03-06 PH PH22254A patent/PH15159A/en unknown
- 1979-03-06 AU AU44862/79A patent/AU528714B2/en not_active Expired
- 1979-03-07 JP JP2722879A patent/JPS54132223A/ja active Granted
- 1979-03-07 AR AR275732A patent/AR223667A1/es active
- 1979-08-08 IE IE704/79A patent/IE48016B1/en not_active IP Right Cessation
-
1982
- 1982-02-09 US US06/347,276 patent/US4388307A/en not_active Expired - Lifetime
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1985
- 1985-02-27 SG SG147/85A patent/SG14785G/en unknown
- 1985-03-22 KE KE3516A patent/KE3516A/xx unknown
- 1985-06-20 HK HK485/85A patent/HK48585A/xx not_active IP Right Cessation
- 1985-12-30 MY MY134/85A patent/MY8500134A/xx unknown
-
1993
- 1993-07-02 NL NL930135C patent/NL930135I1/nl unknown
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1994
- 1994-12-28 NO NO1994028C patent/NO1994028I1/no unknown
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