CA2735660C - Dosage forms for weakly ionizable compounds - Google Patents

Dosage forms for weakly ionizable compounds Download PDF

Info

Publication number: CA2735660C
Authority: CA; Canada
Prior art keywords: drug; weight; modifier; acid; self
Prior art date: 2008-09-09
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 - Fee Related

Application number

CA2735660A

Other languages

English (en)

French (fr)

Other versions

CA2735660A1 (en

Inventor

Vikas Agarwal

Sami M. Nazzal

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Cima Labs Inc

Original Assignee

Cima Labs Inc

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.)

2008-09-09

Filing date

2009-09-09

Publication date

2017-05-30

2009-09-09 Application filed by Cima Labs Inc filed Critical Cima Labs Inc

2010-03-18 Publication of CA2735660A1 publication Critical patent/CA2735660A1/en

2017-05-30 Application granted granted Critical

2017-05-30 Publication of CA2735660C publication Critical patent/CA2735660C/en

Status Expired - Fee Related legal-status Critical Current

2029-09-09 Anticipated expiration legal-status Critical

Links

239000002552 dosage form Substances 0.000 title claims abstract description 117
150000001875 compounds Chemical class 0.000 title description 5
239000000203 mixture Substances 0.000 claims abstract description 348
229940079593 drug Drugs 0.000 claims abstract description 330
239000003814 drug Substances 0.000 claims abstract description 330
239000000839 emulsion Substances 0.000 claims abstract description 167
239000004530 micro-emulsion Substances 0.000 claims abstract description 157
239000003002 pH adjusting agent Substances 0.000 claims abstract description 132
238000000034 method Methods 0.000 claims abstract description 46
239000003921 oil Substances 0.000 claims description 241
235000019198 oils Nutrition 0.000 claims description 239
ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims description 133
229960001929 meloxicam Drugs 0.000 claims description 123
239000002245 particle Substances 0.000 claims description 84
239000003463 adsorbent Substances 0.000 claims description 82
239000007787 solid Substances 0.000 claims description 78
239000000843 powder Substances 0.000 claims description 70
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 68
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 60
239000012071 phase Substances 0.000 claims description 56
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 51
239000004094 surface-active agent Substances 0.000 claims description 44
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 36
-1 polyoxyethylene Polymers 0.000 claims description 31
239000006184 cosolvent Substances 0.000 claims description 29
239000008346 aqueous phase Substances 0.000 claims description 28
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 24
239000008213 purified water Substances 0.000 claims description 24
239000000377 silicon dioxide Substances 0.000 claims description 24
235000012239 silicon dioxide Nutrition 0.000 claims description 24
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 24
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 23
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 22
229960003511 macrogol Drugs 0.000 claims description 22
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 21
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 21
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 21
229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 19
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 19
229920002685 Polyoxyl 35CastorOil Polymers 0.000 claims description 18
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 16
229920000053 polysorbate 80 Polymers 0.000 claims description 16
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 15
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 15
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
241000124008 Mammalia Species 0.000 claims description 15
239000005642 Oleic acid Substances 0.000 claims description 15
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 15
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 15
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 14
239000007762 w/o emulsion Substances 0.000 claims description 14
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 12
229920001213 Polysorbate 20 Polymers 0.000 claims description 12
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 12
239000001361 adipic acid Substances 0.000 claims description 12
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 12
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims description 12
239000001095 magnesium carbonate Substances 0.000 claims description 12
229910000021 magnesium carbonate Inorganic materials 0.000 claims description 12
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 12
239000011736 potassium bicarbonate Substances 0.000 claims description 12
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 12
235000015497 potassium bicarbonate Nutrition 0.000 claims description 12
229910000027 potassium carbonate Inorganic materials 0.000 claims description 12
235000011181 potassium carbonates Nutrition 0.000 claims description 12
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 12
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 12
229910000029 sodium carbonate Inorganic materials 0.000 claims description 12
235000017550 sodium carbonate Nutrition 0.000 claims description 12
239000001384 succinic acid Substances 0.000 claims description 12
239000011975 tartaric acid Substances 0.000 claims description 12
235000002906 tartaric acid Nutrition 0.000 claims description 12
235000011037 adipic acid Nutrition 0.000 claims description 11
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 11
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 11
229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 11
235000019796 monopotassium phosphate Nutrition 0.000 claims description 11
229910000403 monosodium phosphate Inorganic materials 0.000 claims description 11
235000019799 monosodium phosphate Nutrition 0.000 claims description 11
239000007764 o/w emulsion Substances 0.000 claims description 11
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims description 11
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 11
HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 claims description 10
RPUHUBBSMULFQR-UHFFFAOYSA-N 5-hydroxy-5-(5-hydroxy-1,3-dimethyl-2,4,6-trioxo-1,3-diazinan-5-yl)-1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(C)C(=O)N(C)C(=O)C1(O)C1(O)C(=O)N(C)C(=O)N(C)C1=O RPUHUBBSMULFQR-UHFFFAOYSA-N 0.000 claims description 10
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 claims description 10
239000004147 Sorbitan trioleate Substances 0.000 claims description 10
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 claims description 10
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 claims description 10
229940093471 ethyl oleate Drugs 0.000 claims description 10
229920001223 polyethylene glycol Chemical group 0.000 claims description 10
235000019337 sorbitan trioleate Nutrition 0.000 claims description 10
229960000391 sorbitan trioleate Drugs 0.000 claims description 10
JYCQQPHGFMYQCF-UHFFFAOYSA-N 4-tert-Octylphenol monoethoxylate Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCO)C=C1 JYCQQPHGFMYQCF-UHFFFAOYSA-N 0.000 claims description 9
208000002193 Pain Diseases 0.000 claims description 9
239000002202 Polyethylene glycol Chemical group 0.000 claims description 9
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 9
235000014380 magnesium carbonate Nutrition 0.000 claims description 9
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 9
229920002113 octoxynol Polymers 0.000 claims description 9
239000002609 medium Chemical group 0.000 claims description 8
GHVNFZFCNZKVNT-UHFFFAOYSA-M decanoate Chemical compound CCCCCCCCCC([O-])=O GHVNFZFCNZKVNT-UHFFFAOYSA-M 0.000 claims description 7
125000005456 glyceride group Chemical group 0.000 claims description 7
VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 7
BHIZVZJETFVJMJ-UHFFFAOYSA-N 2-hydroxypropyl dodecanoate Chemical group CCCCCCCCCCCC(=O)OCC(C)O BHIZVZJETFVJMJ-UHFFFAOYSA-N 0.000 claims description 6
229930003347 Atropine Natural products 0.000 claims description 6
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 6
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims description 6
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 6
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims description 6
229960000396 atropine Drugs 0.000 claims description 6
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 6
229960005091 chloramphenicol Drugs 0.000 claims description 6
229960002155 chlorothiazide Drugs 0.000 claims description 6
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims description 6
229960001076 chlorpromazine Drugs 0.000 claims description 6
CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 claims description 6
229960001380 cimetidine Drugs 0.000 claims description 6
229960003529 diazepam Drugs 0.000 claims description 6
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 6
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 6
229960004166 diltiazem Drugs 0.000 claims description 6
229960000520 diphenhydramine Drugs 0.000 claims description 6
229960001066 disopyramide Drugs 0.000 claims description 6
UVTNFZQICZKOEM-UHFFFAOYSA-N disopyramide Chemical compound C=1C=CC=NC=1C(C(N)=O)(CCN(C(C)C)C(C)C)C1=CC=CC=C1 UVTNFZQICZKOEM-UHFFFAOYSA-N 0.000 claims description 6
LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims description 6
229960004369 flufenamic acid Drugs 0.000 claims description 6
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 6
229960003883 furosemide Drugs 0.000 claims description 6
229960003878 haloperidol Drugs 0.000 claims description 6
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 claims description 6
229960004801 imipramine Drugs 0.000 claims description 6
229960004194 lidocaine Drugs 0.000 claims description 6
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims description 6
229960002695 phenobarbital Drugs 0.000 claims description 6
229960002036 phenytoin Drugs 0.000 claims description 6
229960000244 procainamide Drugs 0.000 claims description 6
REQCZEXYDRLIBE-UHFFFAOYSA-N procainamide Chemical compound CCN(CC)CCNC(=O)C1=CC=C(N)C=C1 REQCZEXYDRLIBE-UHFFFAOYSA-N 0.000 claims description 6
JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 claims description 6
229960000203 propafenone Drugs 0.000 claims description 6
229960003712 propranolol Drugs 0.000 claims description 6
229960002372 tetracaine Drugs 0.000 claims description 6
GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 claims description 6
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 claims description 6
229960001082 trimethoprim Drugs 0.000 claims description 6
GHHURQMJLARIDK-UHFFFAOYSA-N 2-hydroxypropyl octanoate Chemical compound CCCCCCCC(=O)OCC(C)O GHHURQMJLARIDK-UHFFFAOYSA-N 0.000 claims description 5
239000005995 Aluminium silicate Substances 0.000 claims description 5
206010037660 Pyrexia Diseases 0.000 claims description 5
DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 claims description 5
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 5
235000012211 aluminium silicate Nutrition 0.000 claims description 5
SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 claims description 5
239000000440 bentonite Substances 0.000 claims description 5
229910000278 bentonite Inorganic materials 0.000 claims description 5
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 5
239000002285 corn oil Substances 0.000 claims description 5
235000005687 corn oil Nutrition 0.000 claims description 5
GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 claims description 5
KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 claims description 5
229910000271 hectorite Inorganic materials 0.000 claims description 5
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical group O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 5
239000000347 magnesium hydroxide Substances 0.000 claims description 5
229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 5
239000000395 magnesium oxide Substances 0.000 claims description 5
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
239000000391 magnesium silicate Substances 0.000 claims description 5
235000019793 magnesium trisilicate Nutrition 0.000 claims description 5
229940099273 magnesium trisilicate Drugs 0.000 claims description 5
229910000386 magnesium trisilicate Inorganic materials 0.000 claims description 5
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 5
229940057917 medium chain triglycerides Drugs 0.000 claims description 5
229940049964 oleate Drugs 0.000 claims description 5
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 5
229940026235 propylene glycol monolaurate Drugs 0.000 claims description 5
239000000454 talc Substances 0.000 claims description 5
229910052623 talc Inorganic materials 0.000 claims description 5
239000001069 triethyl citrate Substances 0.000 claims description 5
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 claims description 5
235000013769 triethyl citrate Nutrition 0.000 claims description 5
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 4
206010003246 arthritis Diseases 0.000 claims description 4
229960001722 verapamil Drugs 0.000 claims description 4
201000001320 Atherosclerosis Diseases 0.000 claims description 3
208000024172 Cardiovascular disease Diseases 0.000 claims description 3
208000001953 Hypotension Diseases 0.000 claims description 3
208000006673 asthma Diseases 0.000 claims description 3
230000036543 hypotension Effects 0.000 claims description 3
206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims 3
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 3
235000021313 oleic acid Nutrition 0.000 claims 3
239000001593 sorbitan monooleate Substances 0.000 claims 3
235000011069 sorbitan monooleate Nutrition 0.000 claims 3
229940035049 sorbitan monooleate Drugs 0.000 claims 3
239000007909 solid dosage form Substances 0.000 abstract description 24
238000009472 formulation Methods 0.000 description 48
239000003826 tablet Substances 0.000 description 32
239000003795 chemical substances by application Substances 0.000 description 24
238000004090 dissolution Methods 0.000 description 24
239000000463 material Substances 0.000 description 19
238000002156 mixing Methods 0.000 description 18
239000003995 emulsifying agent Substances 0.000 description 15
GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 15
238000010521 absorption reaction Methods 0.000 description 12
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229940071676 hydroxypropylcellulose Drugs 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
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239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
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FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
239000008041 oiling agent Substances 0.000 description 1
239000006191 orally-disintegrating tablet Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000005192 partition Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
229950005134 polycarbophil Drugs 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
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229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
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239000000376 reactant Substances 0.000 description 1
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238000011084 recovery Methods 0.000 description 1
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235000010413 sodium alginate Nutrition 0.000 description 1
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229940010747 sodium hyaluronate Drugs 0.000 description 1
235000018341 sodium sesquicarbonate Nutrition 0.000 description 1
229910000031 sodium sesquicarbonate Inorganic materials 0.000 description 1
YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
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LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Epidemiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA2735660A 2008-09-09 2009-09-09 Dosage forms for weakly ionizable compounds Expired - Fee Related CA2735660C (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US9549308P	2008-09-09	2008-09-09
US61/095,493		2008-09-09
US16199209P	2009-03-20	2009-03-20
US61/161,992		2009-03-20
PCT/US2009/056362 WO2010030667A2 (en)	2008-09-09	2009-09-09	Dosage forms for weakly ionizable compounds

Publications (2)

Publication Number	Publication Date
CA2735660A1 CA2735660A1 (en)	2010-03-18
CA2735660C true CA2735660C (en)	2017-05-30

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Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2735660A Expired - Fee Related CA2735660C (en)	2008-09-09	2009-09-09	Dosage forms for weakly ionizable compounds

Country Status (5)

Country	Link
EP (1)	EP2334302B1 (de)
JP (1)	JP5661630B2 (de)
CA (1)	CA2735660C (de)
MX (1)	MX340669B (de)
WO (1)	WO2010030667A2 (de)

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MX367165B (es) *	2013-04-05	2019-08-07	Scpharmaceuticals Inc	Formulaciones farmacéuticas para administración subcutánea de furosemida.
CN108295264A (zh) *	2018-03-28	2018-07-20	五邑大学	聚乙烯吡咯烷酮k12的应用
WO2020120482A1 (en)	2018-12-10	2020-06-18	Sq Innovation Ag	Pharmaceutical compositions of furosemide and uses thereof
EP3906019B1 (de)	2019-01-04	2025-11-26	SQ Innovation AG	Pharmazeutische zusammensetzungen von furosemid
US12397005B2 (en)	2019-01-04	2025-08-26	Sq Innovation Ag	Pharmaceutical compositions of torsemide and uses thereof
EA202192129A1 (ru)	2019-01-31	2021-10-19	ЭсСиФАРМАСЬЮТИКАЛЗ ИНК.	Концентрированные жидкие фармацевтические составы фуросемида и способы их введения

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US6613332B1 (en) *	1991-06-21	2003-09-02	The University Of Cincinnati	Oral administration of therapeutic proteins
US6350470B1 (en) *	1998-04-29	2002-02-26	Cima Labs Inc.	Effervescent drug delivery system for oral administration
EP2127642A3 (de) *	1998-08-13	2010-02-24	Cima Labs, Inc.	Mikroemulsionen als feste Dosisformen zur oralen Verabreichung
US6228400B1 (en) *	1999-09-28	2001-05-08	Carlsbad Technology, Inc.	Orally administered pharmaceutical formulations of benzimidazole derivatives and the method of preparing the same
WO2001037838A1 (en) *	1999-11-24	2001-05-31	Wakamoto Pharmaceutical Co., Ltd.	Ophthalmic aqueous preparation
WO2002083102A1 (en) *	2001-02-23	2002-10-24	Cima Labs Inc.	Emulsions as solid dosage forms for oral administration
DE102004021281A1 (de) *	2004-04-29	2005-11-24	Boehringer Ingelheim Vetmedica Gmbh	Verwendung von Meloxicam-Formulierungen in der Veterinärmedizin

2009
- 2009-09-09 CA CA2735660A patent/CA2735660C/en not_active Expired - Fee Related
- 2009-09-09 JP JP2011526303A patent/JP5661630B2/ja not_active Expired - Fee Related
- 2009-09-09 MX MX2011002084A patent/MX340669B/es active IP Right Grant
- 2009-09-09 WO PCT/US2009/056362 patent/WO2010030667A2/en not_active Ceased
- 2009-09-09 EP EP09792369.2A patent/EP2334302B1/de not_active Withdrawn - After Issue

Also Published As

Publication number	Publication date
EP2334302A2 (de)	2011-06-22
MX2011002084A (es)	2011-03-29
MX340669B (es)	2016-07-20
WO2010030667A3 (en)	2010-07-22
CA2735660A1 (en)	2010-03-18
WO2010030667A2 (en)	2010-03-18
JP5661630B2 (ja)	2015-01-28
EP2334302B1 (de)	2018-03-21
JP2012502065A (ja)	2012-01-26

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Date	Code	Title	Description
2014-09-19	EEER	Examination request	Effective date: 20140909
2019-10-21	MKLA	Lapsed	Effective date: 20190909

Publication	Publication Date	Title
US6692771B2 (en)	2004-02-17	Emulsions as solid dosage forms for oral administration
ES2341510T3 (es)	2010-06-21	Microemulsiones como formas farmaceuticas solidas para la administracion oral.
RU2207851C2 (ru)	2003-07-10	Терапевтические средства
US20020102301A1 (en)	2002-08-01	Pharmaceutical solid self-emulsifying composition for sustained delivery of biologically active compounds and the process for preparation thereof
JP5491724B2 (ja)	2014-05-14	生物学的利用能を向上した医薬組成物
CA2735660C (en)	2017-05-30	Dosage forms for weakly ionizable compounds
JP2006511536A (ja)	2006-04-06	水貧溶性薬物のバイオアベイラビリティーを改善する自由流動性固形製剤およびその製造方法
AU2019363244B2 (en)	2024-10-03	Pharmaceutical formulation
PT1492511E (pt)	2009-04-09	Formulação farmacêutica oral na forma de suspensão aquosa de microcápsulas para libertação modificada de princípio(s) activo(s)
US4786495A (en)	1988-11-22	Therapeutic agents
US20120213855A1 (en)	2012-08-23	Dosage forms for weakly ionizable compounds
Beri et al.	2013	Development of fast disintegration tablets as oral drug delivery system-A review
JP4656483B2 (ja)	2011-03-23	新規な自己乳化薬物送達システム
US20150342882A1 (en)	2015-12-03	Methods of treatment using cadotril compositions
AU2003222437A1 (en)	2003-12-19	Pharmaceutical formulation in a drug delivery system and process for preparing the same
AU2001241730B2 (en)	2007-03-15	Emulsions as solid dosage forms for oral administration
AU2001241730A1 (en)	2003-04-17	Emulsions as solid dosage forms for oral administration
CN1771949B (zh)	2011-04-20	尼莫地平软胶囊及其制备方法
Akash	2021	Design, Development, and Evaluation of Nsaid Drug in Soft gel Dosage Form
CN102309476A (zh)	2012-01-11	非诺贝特组合物
JP2005255677A (ja)	2005-09-22	シクロスポリン製剤