LT3278B - Microcapsules and process for preparing thereof - Google Patents

Microcapsules and process for preparing thereof Download PDF

Info

Publication number: LT3278B
Authority: LT; Lithuania
Prior art keywords: oil; polypeptide; microcapsules; emulsion; acid
Prior art date: 1990-02-13

Application number

LTIP441A

Other languages

English (en)

Lithuanian (lt)

Inventor

Hiroaki Okada

Yayoi Inoue

Yasuaki Ogawa

Original Assignee

Takeda Chemical Industries Ltd

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.)

1990-02-13

Filing date

1993-03-19

Publication date

1995-05-25

1993-03-19 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1994-11-25 Publication of LTIP441A publication Critical patent/LTIP441A/xx

1995-05-25 Publication of LT3278B publication Critical patent/LT3278B/lt

Links

239000003094 microcapsule Substances 0.000 title claims abstract description 71
238000004519 manufacturing process Methods 0.000 title description 9
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 32
102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 20
229920001184 polypeptide Polymers 0.000 claims abstract description 15
229920001577 copolymer Polymers 0.000 claims abstract description 6
229920001519 homopolymer Polymers 0.000 claims abstract description 6
239000007762 w/o emulsion Substances 0.000 claims abstract description 4
239000003814 drug Substances 0.000 claims description 27
229940079593 drug Drugs 0.000 claims description 26
239000000839 emulsion Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 20
239000012071 phase Substances 0.000 claims description 17
239000008346 aqueous phase Substances 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 10
229940088597 hormone Drugs 0.000 claims description 9
239000005556 hormone Substances 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
238000001035 drying Methods 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
238000005191 phase separation Methods 0.000 claims description 4
102000011923 Thyrotropin Human genes 0.000 claims description 3
108010061174 Thyrotropin Proteins 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
238000002955 isolation Methods 0.000 claims description 2
229960000874 thyrotropin Drugs 0.000 claims description 2
230000001748 thyrotropin Effects 0.000 claims description 2
229920000954 Polyglycolide Polymers 0.000 claims 3
239000004633 polyglycolic acid Substances 0.000 claims 3
HKTRDWYCAUTRRL-YUMQZZPRSA-N Glu-His Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CN=CN1 HKTRDWYCAUTRRL-YUMQZZPRSA-N 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
230000014759 maintenance of location Effects 0.000 claims 1
229920000747 poly(lactic acid) Polymers 0.000 claims 1
239000004626 polylactic acid Substances 0.000 claims 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract description 25
239000000203 mixture Substances 0.000 abstract description 14
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract description 12
239000004310 lactic acid Substances 0.000 abstract description 7
235000014655 lactic acid Nutrition 0.000 abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
238000013268 sustained release Methods 0.000 description 19
239000012730 sustained-release form Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
229920000642 polymer Polymers 0.000 description 18
238000002347 injection Methods 0.000 description 14
239000007924 injection Substances 0.000 description 14
239000006185 dispersion Substances 0.000 description 13
229960000448 lactic acid Drugs 0.000 description 13
239000012153 distilled water Substances 0.000 description 10
239000003921 oil Substances 0.000 description 10
235000019198 oils Nutrition 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
-1 vasoactive gonadal ) Proteins 0.000 description 10
108010000817 Leuprolide Proteins 0.000 description 7
RGLRXNKKBLIBQS-XNHQSDQCSA-N leuprolide acetate Chemical compound CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 RGLRXNKKBLIBQS-XNHQSDQCSA-N 0.000 description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229940040129 luteinizing hormone Drugs 0.000 description 5
239000003755 preservative agent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
102000009151 Luteinizing Hormone Human genes 0.000 description 4
108010073521 Luteinizing Hormone Proteins 0.000 description 4
239000004372 Polyvinyl alcohol Substances 0.000 description 4
230000009471 action Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
229920002451 polyvinyl alcohol Polymers 0.000 description 4
238000007920 subcutaneous administration Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
238000005354 coacervation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
230000002335 preservative effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000008158 vegetable oil Substances 0.000 description 3
239000004475 Arginine Substances 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
108010003422 Circulating Thymic Factor Proteins 0.000 description 2
102000007644 Colony-Stimulating Factors Human genes 0.000 description 2
108010071942 Colony-Stimulating Factors Proteins 0.000 description 2
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 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
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 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
102400001368 Epidermal growth factor Human genes 0.000 description 2
101800003838 Epidermal growth factor Proteins 0.000 description 2
102000003951 Erythropoietin Human genes 0.000 description 2
108090000394 Erythropoietin Proteins 0.000 description 2
102000018233 Fibroblast Growth Factor Human genes 0.000 description 2
108050007372 Fibroblast Growth Factor Proteins 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
239000004793 Polystyrene Substances 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
229920002988 biodegradable polymer Polymers 0.000 description 2
239000004621 biodegradable polymer Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000012377 drug delivery Methods 0.000 description 2
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229940116977 epidermal growth factor Drugs 0.000 description 2
229940105423 erythropoietin Drugs 0.000 description 2
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238000001914 filtration Methods 0.000 description 2
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239000008103 glucose Substances 0.000 description 2
239000003102 growth factor Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
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238000006460 hydrolysis reaction Methods 0.000 description 2
238000002513 implantation Methods 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
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LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
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229910052757 nitrogen Inorganic materials 0.000 description 2
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235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
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OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 2
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NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 2
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238000003756 stirring Methods 0.000 description 2
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239000002736 nonionic surfactant Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000008385 outer phase Substances 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229960001319 parathyroid hormone Drugs 0.000 description 1
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230000035515 penetration Effects 0.000 description 1
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WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000012667 polymer degradation Methods 0.000 description 1
229920000024 polymyxin B Polymers 0.000 description 1
XDJYMJULXQKGMM-UHFFFAOYSA-N polymyxin E1 Natural products CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O XDJYMJULXQKGMM-UHFFFAOYSA-N 0.000 description 1
KNIWPHSUTGNZST-UHFFFAOYSA-N polymyxin E2 Natural products CC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=O)C(CCN)NC1=O KNIWPHSUTGNZST-UHFFFAOYSA-N 0.000 description 1
229960005266 polymyxin b Drugs 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
229940097325 prolactin Drugs 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
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OWMZNFCDEHGFEP-NFBCVYDUSA-N secretin human Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(N)=O)[C@@H](C)O)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)C1=CC=CC=C1 OWMZNFCDEHGFEP-NFBCVYDUSA-N 0.000 description 1
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239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
229960000553 somatostatin Drugs 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229960005202 streptokinase Drugs 0.000 description 1
YRALAIOMGQZKOW-UHFFFAOYSA-N sulfated caerulein Natural products C=1C=CC=CC=1CC(C(N)=O)NC(=O)C(CC(O)=O)NC(=O)C(CCSC)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)CNC(=O)C(C(C)O)NC(=O)C(NC(=O)C(CC(O)=O)NC(=O)C(CCC(N)=O)NC(=O)C1NC(=O)CC1)CC1=CC=C(OS(O)(=O)=O)C=C1 YRALAIOMGQZKOW-UHFFFAOYSA-N 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
LCJVIYPJPCBWKS-NXPQJCNCSA-N thymosin Chemical compound SC[C@@H](N)C(=O)N[C@H](CO)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CO)C(=O)N[C@H](CO)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@H]([C@H](C)O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCCCN)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](C(C)C)C(=O)N[C@H](C(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@H](CCC(O)=O)C(O)=O LCJVIYPJPCBWKS-NXPQJCNCSA-N 0.000 description 1
229960003873 thymostimulin Drugs 0.000 description 1
230000002916 thymostimulin Effects 0.000 description 1
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230000002485 urinary effect Effects 0.000 description 1
229960005356 urokinase Drugs 0.000 description 1
230000002227 vasoactive effect Effects 0.000 description 1
108010049819 vasocortin Proteins 0.000 description 1
229960003726 vasopressin Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- A61K38/06—Tripeptides
- A61K38/066—TRH, thyroliberin, thyrotropin releasing hormone
- 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
- A61K38/08—Peptides having 5 to 11 amino acids
- A61K38/09—Luteinising hormone-releasing hormone [LHRH], i.e. Gonadotropin-releasing hormone [GnRH]; Related peptides
- 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
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
- A61K9/1647—Polyesters, e.g. poly(lactide-co-glycolide)

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Epidemiology (AREA)
Endocrinology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Immunology (AREA)
Gastroenterology & Hepatology (AREA)
Reproductive Health (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Manufacturing Of Micro-Capsules (AREA)
Peptides Or Proteins (AREA)

LTIP441A 1990-02-13 1993-03-19 Microcapsules and process for preparing thereof LT3278B (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP3313390		1990-02-13
JP889691		1991-01-29
JP3032302A JP2653255B2 (ja)	1990-02-13	1991-01-31	長期徐放型マイクロカプセル
CN91101017A CN1055618C (zh)	1990-02-13	1991-02-12	缓释微胶囊的制备方法

Publications (2)

Publication Number	Publication Date
LTIP441A LTIP441A (en)	1994-11-25
LT3278B true LT3278B (en)	1995-05-25

Family

ID=36754781

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP441A LT3278B (en)	1990-02-13	1993-03-19	Microcapsules and process for preparing thereof

Country Status (22)

Country	Link
EP (1)	EP0442671B1 (fr)
JP (1)	JP2653255B2 (fr)
CN (1)	CN1055618C (fr)
AT (1)	ATE123413T1 (fr)
AU (1)	AU645108B2 (fr)
BR (1)	BR9103553A (fr)
CA (1)	CA2036089C (fr)
DE (1)	DE69110150T2 (fr)
DK (1)	DK0442671T3 (fr)
ES (1)	ES2073117T3 (fr)
FI (1)	FI96278C (fr)
HK (1)	HK188095A (fr)
HU (2)	HU206986B (fr)
IE (1)	IE68436B1 (fr)
LT (1)	LT3278B (fr)
LV (1)	LV10041B (fr)
MX (1)	MX9100721A (fr)
NO (1)	NO301405B1 (fr)
NZ (1)	NZ239381A (fr)
PT (1)	PT96727B (fr)
RU (2)	RU2018306C1 (fr)
UY (1)	UY23276A1 (fr)

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Also Published As

Publication number	Publication date
IE68436B1 (en)	1996-06-12
CN1054009A (zh)	1991-08-28
CA2036089A1 (fr)	1991-08-14
HU206986B (en)	1993-03-01
EP0442671A3 (en)	1992-09-02
EP0442671A2 (fr)	1991-08-21
NO301405B1 (no)	1997-10-27
LV10041A (lv)	1994-05-10
FI96278B (fi)	1996-02-29
NO910555L (no)	1991-08-14
ATE123413T1 (de)	1995-06-15
HUT56268A (en)	1991-08-28
PT96727A (pt)	1991-10-31
ES2073117T3 (es)	1995-08-01
JPH04321622A (ja)	1992-11-11
CA2036089C (fr)	2000-12-05
FI910674A0 (fi)	1991-02-12
AU645108B2 (en)	1994-01-06
LTIP441A (en)	1994-11-25
DE69110150D1 (de)	1995-07-13
DK0442671T3 (da)	1995-07-24
AU8179491A (en)	1992-08-06
HU211586A9 (en)	1995-12-28
HK188095A (en)	1995-12-22
NO910555D0 (no)	1991-02-12
JP2653255B2 (ja)	1997-09-17
BR9103553A (pt)	1992-09-29
FI96278C (fi)	1996-06-10
FI910674L (fi)	1991-08-14
RU2098121C1 (ru)	1997-12-10
RU2018306C1 (ru)	1994-08-30
DE69110150T2 (de)	1996-01-25
MX9100721A (es)	1992-07-31
UY23276A1 (es)	1992-01-15
LV10041B (en)	1994-10-20
NZ239381A (en)	1992-12-23
PT96727B (pt)	1998-07-31
CN1055618C (zh)	2000-08-23
EP0442671B1 (fr)	1995-06-07
IE910474A1 (en)	1991-08-14

Legal Events

Date

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Title

Description

2005-08-25

PD9A

Change of patent owner

Owner name: TAKEDA PHARMACEUTICAL COMPANY LIMITED, JP

Effective date: 20050627

2013-05-27

MK9A

Expiry of a patent

Effective date: 20130319

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