CA2337046C - Sustained release pharmaceutical preparation - Google Patents
Sustained release pharmaceutical preparation Download PDFInfo
- Publication number
- CA2337046C CA2337046C CA002337046A CA2337046A CA2337046C CA 2337046 C CA2337046 C CA 2337046C CA 002337046 A CA002337046 A CA 002337046A CA 2337046 A CA2337046 A CA 2337046A CA 2337046 C CA2337046 C CA 2337046C
- Authority
- CA
- Canada
- Prior art keywords
- hydrochloride
- coating
- therapeutic agent
- sodium
- phenytoin
- 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.)
- Expired - Lifetime
Links
- 239000012730 sustained-release form Substances 0.000 title claims abstract description 33
- 238000013268 sustained release Methods 0.000 title claims abstract description 31
- 239000000825 pharmaceutical preparation Substances 0.000 title description 7
- 239000003814 drug Substances 0.000 claims abstract description 142
- 238000000576 coating method Methods 0.000 claims abstract description 85
- 239000011248 coating agent Substances 0.000 claims abstract description 81
- 239000002702 enteric coating Substances 0.000 claims abstract description 65
- 238000009505 enteric coating Methods 0.000 claims abstract description 65
- 239000011253 protective coating Substances 0.000 claims abstract description 19
- 230000001419 dependent effect Effects 0.000 claims abstract description 17
- 229940124597 therapeutic agent Drugs 0.000 claims description 65
- FJPYVLNWWICYDW-UHFFFAOYSA-M sodium;5,5-diphenylimidazolidin-1-ide-2,4-dione Chemical compound [Na+].O=C1[N-]C(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 FJPYVLNWWICYDW-UHFFFAOYSA-M 0.000 claims description 60
- 229960002790 phenytoin sodium Drugs 0.000 claims description 57
- 239000002552 dosage form Substances 0.000 claims description 38
- 229920000642 polymer Polymers 0.000 claims description 34
- 239000000725 suspension Substances 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 28
- 239000000243 solution Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- 239000008188 pellet Substances 0.000 claims description 15
- 238000005507 spraying Methods 0.000 claims description 15
- 239000006186 oral dosage form Substances 0.000 claims description 12
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 210000004051 gastric juice Anatomy 0.000 claims description 11
- 235000019333 sodium laurylsulphate Nutrition 0.000 claims description 11
- DYWNLSQWJMTVGJ-KUSKTZOESA-N Phenylpropanolamine hydrochloride Chemical compound Cl.C[C@H](N)[C@H](O)C1=CC=CC=C1 DYWNLSQWJMTVGJ-KUSKTZOESA-N 0.000 claims description 10
- 239000007884 disintegrant Substances 0.000 claims description 10
- 229960002305 phenylpropanolamine hydrochloride Drugs 0.000 claims description 10
- 239000004014 plasticizer Substances 0.000 claims description 10
- 239000001856 Ethyl cellulose Substances 0.000 claims description 9
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical group CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 229920001249 ethyl cellulose Polymers 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 235000019325 ethyl cellulose Nutrition 0.000 claims description 8
- DBAKFASWICGISY-BTJKTKAUSA-N Chlorpheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 DBAKFASWICGISY-BTJKTKAUSA-N 0.000 claims description 6
- KBAUFVUYFNWQFM-UHFFFAOYSA-N Doxylamine succinate Chemical compound OC(=O)CCC(O)=O.C=1C=CC=NC=1C(C)(OCCN(C)C)C1=CC=CC=C1 KBAUFVUYFNWQFM-UHFFFAOYSA-N 0.000 claims description 6
- ZQDJSWUEGOYDGT-UHFFFAOYSA-N bromazine hydrochloride Chemical compound [Cl-].C=1C=C(Br)C=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 ZQDJSWUEGOYDGT-UHFFFAOYSA-N 0.000 claims description 6
- 229940046978 chlorpheniramine maleate Drugs 0.000 claims description 6
- CGDDQFMPGMYYQP-UHFFFAOYSA-N disopyramide phosphate Chemical compound OP(O)(O)=O.C=1C=CC=NC=1C(C(N)=O)(CCN(C(C)C)C(C)C)C1=CC=CC=C1 CGDDQFMPGMYYQP-UHFFFAOYSA-N 0.000 claims description 6
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 6
- ZEEXVYNJSAWEML-UHFFFAOYSA-N 3-[4-(4-methylphenyl)sulfanyl-3-nitrophenyl]prop-2-enoic acid Chemical compound C1=CC(C)=CC=C1SC1=CC=C(C=CC(O)=O)C=C1[N+]([O-])=O ZEEXVYNJSAWEML-UHFFFAOYSA-N 0.000 claims description 5
- MEAPRSDUXBHXGD-UHFFFAOYSA-N 3-chloro-n-(4-propan-2-ylphenyl)propanamide Chemical compound CC(C)C1=CC=C(NC(=O)CCCl)C=C1 MEAPRSDUXBHXGD-UHFFFAOYSA-N 0.000 claims description 5
- 229960001377 benactyzine hydrochloride Drugs 0.000 claims description 5
- 229940068716 bromodiphenhydramine hydrochloride Drugs 0.000 claims description 5
- GVNWHCVWDRNXAZ-BTJKTKAUSA-N carbinoxamine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(OCCN(C)C)C1=CC=C(Cl)C=C1 GVNWHCVWDRNXAZ-BTJKTKAUSA-N 0.000 claims description 5
- UKPBEPCQTDRZSE-UHFFFAOYSA-N cyclizine hydrochloride Chemical compound Cl.C1CN(C)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UKPBEPCQTDRZSE-UHFFFAOYSA-N 0.000 claims description 5
- 229960001677 cyclizine hydrochloride Drugs 0.000 claims description 5
- MZDOIJOUFRQXHC-UHFFFAOYSA-N dimenhydrinate Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 MZDOIJOUFRQXHC-UHFFFAOYSA-N 0.000 claims description 5
- 229960004993 dimenhydrinate Drugs 0.000 claims description 5
- 229960001863 disopyramide phosphate Drugs 0.000 claims description 5
- 229960005008 doxylamine succinate Drugs 0.000 claims description 5
- GDCRSXZBSIRSFR-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCOC(=O)C=C GDCRSXZBSIRSFR-UHFFFAOYSA-N 0.000 claims description 5
- ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 claims description 5
- 229960003220 hydroxyzine hydrochloride Drugs 0.000 claims description 5
- 229940070023 iproniazide Drugs 0.000 claims description 5
- KRPAJLYSLFNDOA-UHFFFAOYSA-N mephenesin carbamate Chemical compound CC1=CC=CC=C1OCC(O)COC(N)=O KRPAJLYSLFNDOA-UHFFFAOYSA-N 0.000 claims description 5
- 229950006838 mephenesin carbamate Drugs 0.000 claims description 5
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 5
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims description 5
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 claims description 5
- 229960002532 methamphetamine hydrochloride Drugs 0.000 claims description 5
- 229960001526 phenyltoloxamine Drugs 0.000 claims description 5
- XXPDBLUZJRXNNZ-UHFFFAOYSA-N promethazine hydrochloride Chemical compound Cl.C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 XXPDBLUZJRXNNZ-UHFFFAOYSA-N 0.000 claims description 5
- 229960002244 promethazine hydrochloride Drugs 0.000 claims description 5
- 229960004604 propranolol hydrochloride Drugs 0.000 claims description 5
- XYITYKDGJLHYPW-UHFFFAOYSA-M sodium 2-iodohippurate Chemical compound [Na+].[O-]C(=O)CNC(=O)C1=CC=CC=C1I XYITYKDGJLHYPW-UHFFFAOYSA-M 0.000 claims description 5
- AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 claims description 5
- 229960000340 thiopental sodium Drugs 0.000 claims description 5
- CIVCELMLGDGMKZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC(Cl)=C(C(O)=O)C(Cl)=N1 CIVCELMLGDGMKZ-UHFFFAOYSA-N 0.000 claims description 4
- MFOCDFTXLCYLKU-CMPLNLGQSA-N Phendimetrazine Chemical compound O1CCN(C)[C@@H](C)[C@@H]1C1=CC=CC=C1 MFOCDFTXLCYLKU-CMPLNLGQSA-N 0.000 claims description 4
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 229960000456 carbinoxamine maleate Drugs 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 229960000525 diphenhydramine hydrochloride Drugs 0.000 claims description 4
- MZNZKBJIWPGRID-UHFFFAOYSA-N diphenylphosphorylmethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)CP(C=1C=CC=CC=1)C1=CC=CC=C1 MZNZKBJIWPGRID-UHFFFAOYSA-N 0.000 claims description 4
- 229960004842 ephedrine sulfate Drugs 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 229950000498 methaphenilene Drugs 0.000 claims description 4
- 229960000436 phendimetrazine Drugs 0.000 claims description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 239000002518 antifoaming agent Substances 0.000 claims description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
- IZRPKIZLIFYYKR-UHFFFAOYSA-N phenyltoloxamine Chemical compound CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1 IZRPKIZLIFYYKR-UHFFFAOYSA-N 0.000 claims description 3
- 235000000346 sugar Nutrition 0.000 claims description 3
- 229920000178 Acrylic resin Polymers 0.000 claims description 2
- 239000004925 Acrylic resin Substances 0.000 claims description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
- 229920001800 Shellac Polymers 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
- 239000004208 shellac Substances 0.000 claims description 2
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 claims description 2
- 229940113147 shellac Drugs 0.000 claims description 2
- 235000013874 shellac Nutrition 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- 239000001993 wax Substances 0.000 claims description 2
- NYMGNSNKLVNMIA-UHFFFAOYSA-N Iproniazid Chemical compound CC(C)NNC(=O)C1=CC=NC=C1 NYMGNSNKLVNMIA-UHFFFAOYSA-N 0.000 claims 2
- LDYJXVUOVPVZKA-UHFFFAOYSA-N Methaphenilene Chemical compound C=1C=CC=CC=1N(CCN(C)C)CC1=CC=CS1 LDYJXVUOVPVZKA-UHFFFAOYSA-N 0.000 claims 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 abstract description 67
- 229960002036 phenytoin Drugs 0.000 abstract description 37
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 abstract description 36
- 239000004480 active ingredient Substances 0.000 abstract description 12
- 238000012377 drug delivery Methods 0.000 abstract description 9
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 abstract 1
- 210000002784 stomach Anatomy 0.000 description 27
- 239000002253 acid Substances 0.000 description 22
- 238000010521 absorption reaction Methods 0.000 description 19
- 239000011324 bead Substances 0.000 description 19
- 210000002381 plasma Anatomy 0.000 description 15
- 230000036470 plasma concentration Effects 0.000 description 15
- 230000001225 therapeutic effect Effects 0.000 description 15
- 229920003134 Eudragit® polymer Polymers 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 239000003094 microcapsule Substances 0.000 description 14
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000013543 active substance Substances 0.000 description 11
- 239000002775 capsule Substances 0.000 description 11
- 210000002429 large intestine Anatomy 0.000 description 10
- 210000001072 colon Anatomy 0.000 description 9
- 210000000936 intestine Anatomy 0.000 description 9
- 239000001961 anticonvulsive agent Substances 0.000 description 8
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- 230000008901 benefit Effects 0.000 description 7
- 230000003111 delayed effect Effects 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 210000000813 small intestine Anatomy 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
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- 102220570135 Histone PARylation factor 1_L30D_mutation Human genes 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000000540 analysis of variance Methods 0.000 description 4
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- 230000002496 gastric effect Effects 0.000 description 4
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- -1 phenytoin sodium Chemical compound 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZZYHCCDMBJTROG-UHFFFAOYSA-N 2-(2-benzylphenoxy)ethyl-dimethylazanium;3-carboxy-3,5-dihydroxy-5-oxopentanoate Chemical compound OC(=O)CC(O)(C(O)=O)CC([O-])=O.C[NH+](C)CCOC1=CC=CC=C1CC1=CC=CC=C1 ZZYHCCDMBJTROG-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229920003091 Methocel™ Polymers 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004148 curcumin Substances 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
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- 238000011068 loading method Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- YPDVTKJXVHYWFY-UHFFFAOYSA-N phosphoric acid;n'-propan-2-ylpyridine-4-carbohydrazide Chemical compound OP(O)(O)=O.CC(C)NNC(=O)C1=CC=NC=C1 YPDVTKJXVHYWFY-UHFFFAOYSA-N 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000007619 statistical method Methods 0.000 description 3
- 230000002459 sustained effect Effects 0.000 description 3
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- 206010010904 Convulsion Diseases 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000003556 anti-epileptic effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- FWYFIIQCOLEFQP-UHFFFAOYSA-N dimethyl-[2-[n-(thiophen-2-ylmethyl)anilino]ethyl]azanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1N(CC[NH+](C)C)CC1=CC=CS1 FWYFIIQCOLEFQP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
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- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 2
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- 150000005846 sugar alcohols Chemical class 0.000 description 2
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- UESCARMREGSPTP-UHFFFAOYSA-N 2-(carbamoylamino)-2,2-diphenylacetic acid Chemical compound C=1C=CC=CC=1C(C(O)=O)(NC(=O)N)C1=CC=CC=C1 UESCARMREGSPTP-UHFFFAOYSA-N 0.000 description 1
- NFLLKCVHYJRNRH-UHFFFAOYSA-N 8-chloro-1,3-dimethyl-7H-purine-2,6-dione 2-(diphenylmethyl)oxy-N,N-dimethylethanamine Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Cl)=N2.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 NFLLKCVHYJRNRH-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- ODBLHEXUDAPZAU-ZAFYKAAXSA-N D-threo-isocitric acid Chemical compound OC(=O)[C@H](O)[C@@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-ZAFYKAAXSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001005836 Euchloe ausonia Species 0.000 description 1
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- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
- A61K9/5078—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings with drug-free core
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- 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
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5073—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals having two or more different coatings optionally including drug-containing subcoatings
-
- 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
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
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- 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
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
- A61K9/5005—Wall or coating material
- A61K9/5021—Organic macromolecular compounds
- A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
- A61K9/5042—Cellulose; Cellulose derivatives, e.g. phthalate or acetate succinate esters of hydroxypropyl methylcellulose
- A61K9/5047—Cellulose ethers containing no ester groups, e.g. hydroxypropyl methylcellulose
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
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|---|---|---|---|
| US09/111,188 US5968554A (en) | 1998-07-07 | 1998-07-07 | Sustained release pharmaceutical preparation |
| US09/111,188 | 1998-07-07 | ||
| US09/338,716 | 1999-06-23 | ||
| US09/338,716 US6312728B1 (en) | 1998-07-07 | 1999-06-23 | Sustained release pharmaceutical preparation |
| PCT/US1999/014204 WO2000001369A1 (en) | 1998-07-07 | 1999-06-25 | Sustained release pharmaceutical preparation |
Publications (2)
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|---|---|
| CA2337046A1 CA2337046A1 (en) | 2000-01-13 |
| CA2337046C true CA2337046C (en) | 2005-08-16 |
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|---|---|
| US (1) | US6312728B1 (enExample) |
| EP (1) | EP1094790B9 (enExample) |
| JP (1) | JP2003524592A (enExample) |
| AT (1) | ATE274344T1 (enExample) |
| AU (1) | AU5084299A (enExample) |
| CA (1) | CA2337046C (enExample) |
| DE (1) | DE69919713T2 (enExample) |
| ES (1) | ES2226412T3 (enExample) |
| IL (1) | IL140761A0 (enExample) |
| WO (1) | WO2000001369A1 (enExample) |
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| SE9803871D0 (sv) * | 1998-11-11 | 1998-11-11 | Pharmacia & Upjohn Ab | Therapeutic method and formulation |
| US20030068356A1 (en) * | 2001-07-10 | 2003-04-10 | Pather S. Indiran | Sequential drug delivery systems |
| US6572889B1 (en) | 2002-03-07 | 2003-06-03 | Noveon Ip Holdings Corp. | Controlled release solid dosage carbamazepine formulations |
| US20040043067A1 (en) * | 2002-06-19 | 2004-03-04 | Salamone Joseph C. | Fluorosiloxane matrix controlled diffusion drug delivery systems |
| MY142204A (en) | 2002-07-25 | 2010-10-29 | Pharmacia Corp | Pramipexole once-daily dosage form |
| BR0315731A (pt) * | 2002-10-30 | 2005-09-06 | Pharmacia Corp | Comprimidos orais de liberação prolongada e métodos para fabricar e usar os mesmos |
| US7988993B2 (en) * | 2002-12-09 | 2011-08-02 | Andrx Pharmaceuticals, Inc. | Oral controlled release dosage form |
| US20040253293A1 (en) * | 2003-06-16 | 2004-12-16 | Afshin Shafiee | Rate controlled release of a pharmaceutical agent in a biodegradable device |
| JP2007507491A (ja) * | 2003-09-29 | 2007-03-29 | シージェー コーポレーション | 徐放性製剤 |
| US7670624B2 (en) * | 2004-01-29 | 2010-03-02 | Astella Pharma Inc. | Gastrointestinal-specific multiple drug release system |
| WO2005117697A2 (en) * | 2004-05-28 | 2005-12-15 | Narayanan Ramasubramanian | Unified indigestion package and process for patient compliance with prescribed medication regimen |
| US9592197B2 (en) * | 2004-12-16 | 2017-03-14 | Sovereign Pharmaceuticals, Llc | Dosage form containing diphenhydramine and another drug |
| US20070003622A1 (en) * | 2004-12-16 | 2007-01-04 | Sovereign Pharmaceuticals, Ltd. | Diphenhydramine containing dosage form |
| US20060034910A1 (en) * | 2004-08-09 | 2006-02-16 | Sanjay Patel | Pharmaceutical composition for extended release of phenytoin sodium |
| ME01316B (me) | 2004-08-13 | 2013-12-20 | Boehringer Ingelheim Int | Formulacija tablete sa produženim oslobađanjem koji sadrži pramipeksol ili njegovu farmaceutski prihvatljivu so |
| UA88477C2 (ru) | 2004-08-13 | 2009-10-26 | Бёрингер Ингельхайм Интернациональ Гмбх | Композиция пеллеты пролонгированного высвобождения, которая содержит прамипексол или его фармацевтически приемлемую соль, способ ее изготовления и ее применение |
| US20060134175A1 (en) * | 2004-12-22 | 2006-06-22 | Stephen Bartels | Drug eluting pharmaceutical delivery system for treatment of ocular disease and method of use |
| US7529255B2 (en) * | 2005-04-21 | 2009-05-05 | Microsoft Corporation | Peer-to-peer multicasting using multiple transport protocols |
| BRPI0707736A2 (pt) | 2006-02-13 | 2011-05-10 | Vanda Pharmaceuticals Inc | formulaÇÕes de imidazolilalquil-piridinas de dosagem estÁvel |
| JP5228359B2 (ja) * | 2007-04-12 | 2013-07-03 | ニプロ株式会社 | 主薬粒子及びその製造方法ならびに口腔内崩壊錠 |
| PL2152250T3 (pl) | 2007-05-07 | 2020-06-15 | Evonik Röhm Gmbh | Stałe postaci dawkowania zawierające otoczkę dojelitową o przyspieszonym uwalnianiu leku |
| EP2222301B1 (en) * | 2007-12-13 | 2014-10-08 | Vanda Pharmaceuticals Inc. | Method and composition for treating an alpha adrenoceptor-mediated condition |
| EP2222300B1 (en) | 2007-12-13 | 2014-06-11 | Vanda Pharmaceuticals Inc. | Method and composition for treating a serotonin receptor-mediated condition |
| US20090214665A1 (en) * | 2008-02-26 | 2009-08-27 | Lai Felix S | Controlled Release Muscarinic Receptor Antagonist Formulation |
| US8663671B2 (en) * | 2009-11-05 | 2014-03-04 | Philip Morris Usa Inc. | Methods and compositions for producing hydrogel capsules coated for low permeability and physical integrity |
| US8999393B1 (en) | 2013-01-09 | 2015-04-07 | Edgemont Pharmaceuticals Llc | Sustained release formulations of lorazepam |
| BR112022012514A2 (pt) | 2019-12-27 | 2022-09-06 | Evelo Biosciences Inc | Formas de dosagem sólidas que contêm bactérias e vesículas extracelulares microbianas |
| WO2021146523A1 (en) | 2020-01-17 | 2021-07-22 | Evelo Biosciences, Inc. | Solid dosage forms with improved disintegration profiles |
| CN115551486A (zh) | 2020-04-17 | 2022-12-30 | 伊夫罗生物科学公司 | 具有改善的崩解谱的固体剂型 |
| AU2021342481A1 (en) | 2020-09-18 | 2023-05-04 | Evelo Biosciences, Inc. | Solid dosage forms of bacteria |
| US20240024377A1 (en) | 2020-10-29 | 2024-01-25 | Evelo Biosciences, Inc. | Compositions comprising spirulina components |
| JP2024501481A (ja) | 2020-12-14 | 2024-01-12 | エヴェロ バイオサイエンシズ，インコーポレーテッド | 細胞外小胞調製物 |
| WO2022140396A1 (en) | 2020-12-22 | 2022-06-30 | Evelo Biosciences, Inc. | Compositions comprising animal hemoglobin |
| US20240423924A1 (en) | 2021-01-26 | 2024-12-26 | Evelo Biosciences, Inc. | Prevotella extracellular vesicle preparations |
| EP4297762A1 (en) | 2021-02-26 | 2024-01-03 | Evelo Biosciences, Inc. | Compositions and methods for reducing cytokine expression |
| WO2022187578A1 (en) | 2021-03-05 | 2022-09-09 | Evelo Biosciences, Inc. | Solid dosage forms |
| TW202304415A (zh) | 2021-04-08 | 2023-02-01 | 美商艾弗洛生物科技股份有限公司 | 含有細菌的藥物製劑 |
| WO2022221183A1 (en) | 2021-04-12 | 2022-10-20 | Evelo Biosciences, Inc. | Fournierella extracellular vesicle preparations |
| WO2022251166A2 (en) | 2021-05-25 | 2022-12-01 | Evelo Biosciences, Inc. | Bacterial compositions comprising soy hemoglobin |
| WO2023049268A1 (en) | 2021-09-24 | 2023-03-30 | Evelo Biosciences, Inc. | Solid dosage forms containing bacteria and microbial extracellular vesicles |
| WO2023114300A1 (en) | 2021-12-14 | 2023-06-22 | Evelo Biosciences, Inc. | Fournierella massiliensis bacteria extracellular vesicle preparations |
| WO2023114295A1 (en) | 2021-12-14 | 2023-06-22 | Evelo Biosciences, Inc. | Veillonella parvula bacteria extracellular vesicle preparations |
| WO2023114293A1 (en) | 2021-12-14 | 2023-06-22 | Evelo Biosciences, Inc. | Extracellular vesicle assays |
| WO2023146843A1 (en) | 2022-01-25 | 2023-08-03 | Evelo Biosciences, Inc. | Extracellular vesicle compositions and methods of use |
| WO2023183396A1 (en) | 2022-03-22 | 2023-09-28 | Evelo Biosciences, Inc. | Compositions and methods of treating inflammation using prevotella histicola |
| WO2023200837A1 (en) | 2022-04-13 | 2023-10-19 | Evelo Biosciences, Inc. | Compositions and methods of treating inflammation using prevotella histicola |
| WO2023239728A1 (en) | 2022-06-07 | 2023-12-14 | Evelo Biosciences, Inc. | Compositions and methods of treating inflammation using prevotella histicola extracellular vesicles |
| WO2024102226A1 (en) | 2022-10-14 | 2024-05-16 | Evelo Biosciences, Inc. | Methods for assaying drug substances and drug products by using cell lines with nf-kb- inducible reporter genes |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994260A (en) | 1982-05-28 | 1991-02-19 | Astra Lakemedel Aktiebolag | Pharmaceutical mixture |
| US5238686A (en) | 1986-03-27 | 1993-08-24 | Kinaform Technology, Inc. | Sustained-release pharmaceutical preparation |
| US4968508A (en) | 1987-02-27 | 1990-11-06 | Eli Lilly And Company | Sustained release matrix |
| US5540945A (en) * | 1989-05-11 | 1996-07-30 | Chugai Seiyaku Kabushiki Kaisha | Pharmaceutical preparations for oral administration that are adapted to release the drug at appropriate sites in the intestines |
| IL95423A (en) * | 1989-09-21 | 1994-11-11 | American Cyanamid Co | Pulsatile once-a-day delivery systems for minocycline |
| EP0497977B1 (en) * | 1989-10-26 | 1995-03-15 | Nippon Shinyaku Company, Limited | Gastric preparation |
| US5229131A (en) | 1990-02-05 | 1993-07-20 | University Of Michigan | Pulsatile drug delivery system |
| US5188836A (en) | 1990-07-27 | 1993-02-23 | Warner-Lambert Company | Sustained release formulations |
| US5102668A (en) | 1990-10-05 | 1992-04-07 | Kingaform Technology, Inc. | Sustained release pharmaceutical preparation using diffusion barriers whose permeabilities change in response to changing pH |
| US5286493A (en) | 1992-01-27 | 1994-02-15 | Euroceltique, S.A. | Stabilized controlled release formulations having acrylic polymer coating |
| DE19630035A1 (de) * | 1996-07-25 | 1998-01-29 | Asta Medica Ag | Tramadol Multiple Unit Formulierungen |
| US5885616A (en) * | 1997-08-18 | 1999-03-23 | Impax Pharmaceuticals, Inc. | Sustained release drug delivery system suitable for oral administration |
| US5968554A (en) * | 1998-07-07 | 1999-10-19 | Cascade Development, Inc. A Subsidiary Of Cardinal Health, Inc. | Sustained release pharmaceutical preparation |
-
1999
- 1999-06-23 US US09/338,716 patent/US6312728B1/en not_active Expired - Lifetime
- 1999-06-25 JP JP2000557816A patent/JP2003524592A/ja active Pending
- 1999-06-25 IL IL14076199A patent/IL140761A0/xx unknown
- 1999-06-25 WO PCT/US1999/014204 patent/WO2000001369A1/en not_active Ceased
- 1999-06-25 ES ES99935347T patent/ES2226412T3/es not_active Expired - Lifetime
- 1999-06-25 AT AT99935347T patent/ATE274344T1/de not_active IP Right Cessation
- 1999-06-25 EP EP99935347A patent/EP1094790B9/en not_active Expired - Lifetime
- 1999-06-25 AU AU50842/99A patent/AU5084299A/en not_active Abandoned
- 1999-06-25 DE DE69919713T patent/DE69919713T2/de not_active Expired - Lifetime
- 1999-06-25 CA CA002337046A patent/CA2337046C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE69919713T2 (de) | 2005-09-22 |
| EP1094790B9 (en) | 2005-05-04 |
| WO2000001369A1 (en) | 2000-01-13 |
| EP1094790B1 (en) | 2004-08-25 |
| EP1094790A1 (en) | 2001-05-02 |
| AU5084299A (en) | 2000-01-24 |
| ES2226412T3 (es) | 2005-03-16 |
| IL140761A0 (en) | 2002-02-10 |
| US6312728B1 (en) | 2001-11-06 |
| CA2337046A1 (en) | 2000-01-13 |
| EP1094790A4 (en) | 2003-03-12 |
| JP2003524592A (ja) | 2003-08-19 |
| ATE274344T1 (de) | 2004-09-15 |
| DE69919713D1 (de) | 2004-09-30 |
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| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20190625 |