CA2472432C - Comprime mou contenant des matieres cellulosiques a poids moleculaire eleve - Google Patents

Comprime mou contenant des matieres cellulosiques a poids moleculaire eleve Download PDF

Info

Publication number: CA2472432C
Authority: CA; Canada
Prior art keywords: dosage form; percent; mixtures; hydroxyalkylcellulose; active ingredient
Prior art date: 2003-06-27
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

CA 2472432

Other languages

English (en)

Other versions

CA2472432A1 (fr

Inventor

David Wynn

Nick Parikh

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.)

Kenvue Brands LLC

Original Assignee

McNeil PPC 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.)

2003-06-27

Filing date

2004-06-25

Publication date

2012-02-21

2003-06-27 Priority claimed from US10/608,681 external-priority patent/US20040265373A1/en

2003-06-27 Priority claimed from US10/607,766 external-priority patent/US20040265372A1/en

2004-06-25 Application filed by McNeil PPC Inc filed Critical McNeil PPC Inc

2004-12-27 Publication of CA2472432A1 publication Critical patent/CA2472432A1/fr

2012-02-21 Application granted granted Critical

2012-02-21 Publication of CA2472432C publication Critical patent/CA2472432C/fr

2024-06-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000004480 active ingredient Substances 0.000 claims abstract description 56
229920013821 hydroxy alkyl cellulose Polymers 0.000 claims abstract description 46
238000000576 coating method Methods 0.000 claims abstract description 41
239000011248 coating agent Substances 0.000 claims abstract description 39
239000011159 matrix material Substances 0.000 claims abstract description 27
239000012729 immediate-release (IR) formulation Substances 0.000 claims abstract description 17
210000000214 mouth Anatomy 0.000 claims abstract description 16
239000002552 dosage form Substances 0.000 claims description 86
239000000203 mixture Substances 0.000 claims description 57
239000002245 particle Substances 0.000 claims description 53
229920000642 polymer Polymers 0.000 claims description 47
239000003826 tablet Substances 0.000 claims description 38
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 34
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 33
230000000873 masking effect Effects 0.000 claims description 31
229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 26
235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 26
239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 24
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 23
229960001680 ibuprofen Drugs 0.000 claims description 23
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 22
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 18
229920002301 cellulose acetate Polymers 0.000 claims description 17
239000001863 hydroxypropyl cellulose Substances 0.000 claims description 17
239000007864 aqueous solution Substances 0.000 claims description 15
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 10
239000001856 Ethyl cellulose Substances 0.000 claims description 9
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims description 9
235000019325 ethyl cellulose Nutrition 0.000 claims description 9
229920001249 ethyl cellulose Polymers 0.000 claims description 9
229960005489 paracetamol Drugs 0.000 claims description 9
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 9
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
230000009747 swallowing Effects 0.000 claims description 9
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 claims description 8
229930195725 Mannitol Natural products 0.000 claims description 8
229920001577 copolymer Polymers 0.000 claims description 8
238000001035 drying Methods 0.000 claims description 8
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 claims description 8
239000000594 mannitol Substances 0.000 claims description 8
235000010355 mannitol Nutrition 0.000 claims description 8
239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 7
150000001720 carbohydrates Chemical class 0.000 claims description 7
229920006217 cellulose acetate butyrate Polymers 0.000 claims description 7
235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 7
239000007891 compressed tablet Substances 0.000 claims description 6
229920003063 hydroxymethyl cellulose Polymers 0.000 claims description 6
229940031574 hydroxymethyl cellulose Drugs 0.000 claims description 6
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 claims description 6
230000007935 neutral effect Effects 0.000 claims description 6
229920003169 water-soluble polymer Polymers 0.000 claims description 6
BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 5
229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 5
229920002284 Cellulose triacetate Polymers 0.000 claims description 5
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 5
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 5
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 5
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 5
NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 claims description 5
229960000590 celecoxib Drugs 0.000 claims description 5
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 claims description 5
229940081734 cellulose acetate phthalate Drugs 0.000 claims description 5
JURKNVYFZMSNLP-UHFFFAOYSA-N cyclobenzaprine Chemical compound C1=CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 JURKNVYFZMSNLP-UHFFFAOYSA-N 0.000 claims description 5
229960003572 cyclobenzaprine Drugs 0.000 claims description 5
229960001259 diclofenac Drugs 0.000 claims description 5
DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 5
229960002390 flurbiprofen Drugs 0.000 claims description 5
SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 5
DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 5
229960000991 ketoprofen Drugs 0.000 claims description 5
229960001929 meloxicam Drugs 0.000 claims description 5
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 5
229960002009 naproxen Drugs 0.000 claims description 5
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 5
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 5
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 5
229940068968 polysorbate 80 Drugs 0.000 claims description 5
229920000053 polysorbate 80 Polymers 0.000 claims description 5
229960000371 rofecoxib Drugs 0.000 claims description 5
RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 claims description 5
239000000600 sorbitol Substances 0.000 claims description 5
235000010356 sorbitol Nutrition 0.000 claims description 5
239000000811 xylitol Substances 0.000 claims description 5
235000010447 xylitol Nutrition 0.000 claims description 5
229960002675 xylitol Drugs 0.000 claims description 5
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 5
SPFMQWBKVUQXJV-BTVCFUMJSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;hydrate Chemical compound O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O SPFMQWBKVUQXJV-BTVCFUMJSA-N 0.000 claims description 4
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 4
229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 4
229960000673 dextrose monohydrate Drugs 0.000 claims description 4
238000007907 direct compression Methods 0.000 claims description 4
238000004090 dissolution Methods 0.000 claims description 4
229920000639 hydroxypropylmethylcellulose acetate succinate Polymers 0.000 claims description 4
229960001855 mannitol Drugs 0.000 claims description 4
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 4
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239000001267 polyvinylpyrrolidone Substances 0.000 claims description 4
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SPCKHVPPRJWQRZ-UHFFFAOYSA-N 2-benzhydryloxy-n,n-dimethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 SPCKHVPPRJWQRZ-UHFFFAOYSA-N 0.000 claims description 3
ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims description 3
MKXZASYAUGDDCJ-SZMVWBNQSA-N LSM-2525 Chemical compound C1CCC[C@H]2[C@@]3([H])N(C)CC[C@]21C1=CC(OC)=CC=C1C3 MKXZASYAUGDDCJ-SZMVWBNQSA-N 0.000 claims description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 3
TYVWBCMQECJNSK-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)butan-2-yl]azanium;chloride Chemical compound [Cl-].CC([NH3+])(C)C(C)OC(=O)C(C)=C TYVWBCMQECJNSK-UHFFFAOYSA-N 0.000 claims description 3
GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 claims description 3
229960001803 cetirizine Drugs 0.000 claims description 3
SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 claims description 3
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KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 3
229960001985 dextromethorphan Drugs 0.000 claims description 3
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DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 claims description 3
238000007908 dry granulation Methods 0.000 claims description 3
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 3
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125000005397 methacrylic acid ester group Chemical group 0.000 claims description 3
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239000001923 methylcellulose Substances 0.000 claims description 3
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DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 claims description 3
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XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 3
KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims description 3
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DEGZUQBZHACZKW-UHFFFAOYSA-N 2-(methylamino)ethyl 2-methylprop-2-enoate Chemical compound CNCCOC(=O)C(C)=C DEGZUQBZHACZKW-UHFFFAOYSA-N 0.000 claims description 2
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CA 2472432 2003-06-27 2004-06-25 Comprime mou contenant des matieres cellulosiques a poids moleculaire eleve Expired - Fee Related CA2472432C (fr)

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US10/607,766		2003-06-27
US10/608,681		2003-06-27
US10/608,681 US20040265373A1 (en)	2003-06-27	2003-06-27	Soft tablet containing high molecular weight cellulosics
US10/607,766 US20040265372A1 (en)	2003-06-27	2003-06-27	Soft tablet containing high molecular weight cellulosics

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CA (1)	CA2472432C (fr)

2004
- 2004-06-25 CA CA 2472432 patent/CA2472432C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2472432A1 (fr)	2004-12-27

Legal Events

Date	Code	Title	Description
2009-04-02	EEER	Examination request
2018-08-07	MKLA	Lapsed	Effective date: 20180626

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CN101677967A (zh)	2010-03-24	调释固体或半固体剂型
US20120082729A1 (en)	2012-04-05	Quick dissolve compositions and tablets based thereon
AU2010315414B2 (en)	2015-07-09	Fast dissolving/disintegrating coating compositions
CA2472432C (fr)	2012-02-21	Comprime mou contenant des matieres cellulosiques a poids moleculaire eleve
MX2008004381A (en)	2008-09-02	Oral composition containing a salivation inducing agent