IP Library Granted Patent US 8,110,219
Granted Patent B2
US 8,110,219 · App. 12/328,828 · Granted Feb 7, 2012

Controlled release dosage forms

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Quick Facts
Patent No.
US 8,110,219
App. No.
12/328,828
Granted
Feb 7, 2012
Kind
B2
Abstract

The invention provides stable controlled release monolithic coating compositions for use in coating pharmaceutical oral dosage forms comprising a polyglycol having a melting point greater than 55° C. and an aqueous dispersion of a neutral ester copolymer lacking functional groups.

Claims (39)

1. A controlled release oral dosage form comprising:

a) a core, wherein said core comprises:

i) an effective amount of metformin hydrochloride, and

ii) one or more first pharmaceutically acceptable excipients, and

b) a stable controlled release monolithic coating surrounding the core, wherein the stable controlled release coating is formed by a process comprising:

coating the core with a coating composition to form a coated core, and curing the coated core to form the stable controlled release coating, wherein the coating composition comprises

i) an aqueous dispersion of a neutral ester copolymer without any functional groups;

ii) a poly glycol having a melting point of at least about 55° C., and

iii) one or more second pharmaceutically acceptable excipients; and wherein the curing is conducted at a temperature at least equal to or greater than the melting point of the poly glycol,

wherein the stable controlled release coating hydrates when placed into water, and wherein the one or more first pharmaceutically acceptable excipients comprises cross-linked polyvinylpyrrolidone.

2. The controlled release oral dosage form of claim 1 wherein the effective amount of the metformin hydrochloride is more than about 500 mg.

3. The controlled release oral dosage form of claim 1 wherein the effective amount of the metformin hydrochloride is about 1000 mg.

4. The controlled release oral dosage form of claim 1 wherein the dosage form floats when placed in an aqueous environment.

5. The controlled release oral dosage form of claim 1 wherein the dosage form expands when placed in an aqueous environment.

6. The controlled release oral dosage form of claim 1 wherein upon oral administration to a patient, an effective amount of the metformin hydrochloride is released into a region of the patient's upper gastrointestinal tract.

7. The controlled release oral dosage form of claim 1 wherein upon oral administration to a patient, the dosage form remains substantially intact until substantially all of the active agent is released.

8. The controlled release oral dosage form of claim 1 wherein the stable controlled release monolithic coating is formed by a process that excludes usage of an organic solvent.

9. The controlled release oral dosage form of claim 1 , wherein the one or more first pharmaceutically acceptable excipients comprises at least one of colloidal silicon dioxide, polyvinyl alcohol, crospovidone, glyceryl behenate, and a mixture thereof

10. The controlled release oral dosage form of claim 1 , wherein the one or more second pharmaceutically acceptable excipients comprises at least one of hypromellose, talc, titanium dioxide, simethicone, polysorbate 80, and a mixture thereof

11. The controlled release oral dosage form of claim 1 , wherein the one or more second pharmaceutically acceptable excipients comprises at least one of an anti-tacking agent agent, an emulsifying agent agent, a hydrophilic agent, an antifoaming agent, a flavorant, a colorant, a sweetener and a mixture thereof

12. The controlled release oral dosage form of claim 1 wherein the aqueous dispersion of neutral ester copolymer without any functional groups comprises at least one of a 30% aqueous dispersion of a neutral copolymer based on ethyl acrylate and methacrylate, a 40% aqueous dispersion of a neutral copolymer based on ethyl acrylate and methacrylate, and mixtures thereof.

13. The controlled release oral dosage form of claim 1 wherein the poly glycol comprises at least one of polyethylene glycol 4000, polyethylene glycol 4600, polyethylene glycol 6000, polyethylene glycol 8000, polyethylene glycol 10000, polyethylene glycol 12000, polyethylene glycol 20000, polyethylene glycol 35000, poloxamer 188, poloxamer 338, poloxamer 407, polyethylene oxides, polyoxyethylene alkyl ethers, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene stearates, and a mixture thereof.

14. The controlled release oral dosage form of claim 1 wherein the curing is conducted for a time period of from about 1 to about 24 hours.

15. The controlled release oral dosage form of claim 1 wherein the curing is conducted for a time period of from about 1 to about 16 hours.

16. The controlled release oral dosage form of claim 1 wherein the curing is conducted for a time period of from about 2 to about 7 hours.

17. The controlled release oral dosage form of claim 1 wherein the curing is conducted for a time period of from about 4 to about 7 hours.

18. The controlled release oral dosage form of claim 1 wherein the curing is conducted for a time period of from about 2 to about 4 hours.

19. The controlled release oral dosage form of claim 1 wherein the curing is conducted for a time period of from about 1 to about 3 hours.

20. The controlled release oral dosage form of claim 1 wherein the curing is conducted at a temperature at least equal to or greater than about 60 degrees C.

21. A controlled release oral dosage form comprising:

a) a core, wherein said core comprises:

i) metformin hydrochloride, and

ii) one or more first pharmaceutically acceptable excipients, and

b) a stable controlled release monolithic coating surrounding the core, wherein the stable controlled release monolithic coating is formed by a process comprising:

coating the core with a coating composition to form a coated core, and curing the coated core to form the stable controlled release coating, wherein the coating composition comprises

i) an ethyl acrylate and methyl methacrylate copolymer dispersion;

ii) a poly glycol comprising at least one of polyethylene glycol 4000, polyethylene glycol 4600, polyethylene glycol 6000, polyethylene glycol 8000, polyethylene glycol 10000, polyethylene glycol 12000, polyethylene glycol 20000, polyethylene glycol 35000, and a mixture thereof, and

iii) one or more second pharmaceutically acceptable excipients wherein the poly glycol has a melting point of at least about 55° C; and wherein the curing is conducted at a temperature at least equal to or greater than the melting point of the poly glycol,

wherein the stable controlled release coating hydrates when placed into water, and wherein the one or more first pharmaceutically acceptable excipients comprises cross-linked polyvinylpyrrolidone.

Assignments (24)
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 073637/0001 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMA POLAND SPOLKA Z ORGANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z.O.O.
Reel/Frame 073637/0222 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
Reel/Frame 073654/0300 →
RELEASE OF SECURITY INTEREST Recorded Apr 8, 2025
From: BARCLAYS BANK PLC, AS COLLATERAL AGENT
To: SOLTA MEDICAL, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH IRELAND LIMITED (F/K/A/ VALEANT PHARMACEUTICALS IRELAND LIMITED); SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD; SANTARUS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; HUMAX PHARMACEUTICAL S.A.; SOLTA MEDICAL IRELAND LIMITED; BAUSCH & LOMB MEXICO, S.A. DE C.V.; BAUSCH+LOMB OPS B.V.; BAUSCH HEALTH AMERICAS, INC.; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH HOLDCO LIMITED; BAUSCH HEALTH MAGYARORSZAG KFT (A/K/A BAUSCH HEALTH HUNGARY LLC); BAUSCH HEALTH POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA (F/K/A VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA); BAUSCH HEALTH US, LLC; BAUSCH HEALTH, CANADA INC. / SANTE BAUSCH, CANADA INC.; ICN POLFA RZESZOW SPOLKA AKCYJNA (A/K/A ICN POLFA RZESZOW S.A.); ORAPHARMA, INC.; PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA SPOLKA AKCYJNA (A/K/A PRZEDSIEBIORSTWO FARMACEUTYCZNE JELFA S.A.); SOLTA MEDICAL DUTCH HOLDINGS B.V.; V-BAC HOLDING CORP.; VRX HOLDCO LLC; 1261229 B.C. LTD.; 1530065 B.C. LTD.
Reel/Frame 070778/0199 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Nov 4, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061882/0708 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Nov 4, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 062078/0276 →
SECURITY AGREEMENT (SECOND LIEN) Recorded Oct 5, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061606/0468 →
SECURITY AGREEMENT (FIRST LIEN) Recorded Oct 4, 2022
From: BAUSCH HEALTH US, LLC; BAUSCH HEALTH AMERICAS, INC.; MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 061595/0066 →
SECURITY INTEREST Recorded Jun 13, 2022
From: BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; BAUSCH HEALTH IRELAND LIMITED; SOLTA MEDICAL IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON
Reel/Frame 060346/0705 →
SECURITY INTEREST Recorded Oct 5, 2021
From: BAUSCH & LOMB IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; DR. GERHARD MANN CHEM.-PHARM. FABRIK GMBH; TECHNOLAS PERFECT VISION GMBH
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 057821/0800 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Jul 3, 2019
From: BAUSCH HEALTH IRELAND LIMITED; BAUSCH HEALTH COMPANIES INC.; BAUSCH HEALTH, CANADA INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT PHARMACEUTICALS LUXEMBOURG S.À R.L.; VALEANT PHARMA POLAND SPOLKA Z OGRANICZONA ODPOWIEDZIALNOSCIA; VALEANT SP. Z O. O.
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 049672/0652 →
MERGER Recorded Apr 22, 2019
From: VALEANT INTERNATIONAL BERMUDA
To: VALEANT HOLDINGS IRELAND
Reel/Frame 048954/0344 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 22, 2019
From: VALEANT HOLDINGS IRELAND
To: BAUSCH HEALTH IRELAND LIMITED
Reel/Frame 048954/0715 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 045444/0299 →
SECURITY INTEREST Recorded Feb 26, 2018
From: ATON PHARMA, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH & LOMB PHARMA HOLDINGS CORP.; COMMONWEALTH LABORATORIES, LLC; DOW PHARMACEUTICAL SCIENCES, INC.; ECR PHARMACEUTICALS CO., INC.; LABORATOIRE CHAUVIN S.A.S.; MEDICIS PHARMACEUTICAL CORPORATION; ONPHARMA INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; SOLTA MEDICAL, INC.; SYNERGETICS USA, INC.; TECHNOLAS PERFECT VISION GMBH; VALEANT CANADA LP; VALEANT PHARMACEUTICALS INTERNATIONAL; VALEANT PHARMACEUTICALS INTERNATIONAL, INC.; VALEANT PHARMACEUTICALS NORTH AMERICA LLC; WIRRA IP PTY LIMITED; VALEANT PHARMA POLAND SP. Z O.O.; VALEANT PHARMACEUTICALS LUXEMBOURG S.A R.L.; VALEANT PHARMACEUTICALS IRELAND LIMITED
To: THE BANK OF NEW YORK MELLON, AS COLLATERAL AGENT
Reel/Frame 045444/0634 →
NOTICE OF SUCCESSION OF AGENCY Recorded Jan 9, 2015
From: GOLDMAN SACHS LENDING PARTNERS, LLC
To: BARCLAYS BANK PLC, AS SUCCESSOR AGENT
Reel/Frame 034749/0689 →
CHANGE IN NAME AND COUNTRY OF INCORPORATION Recorded Aug 9, 2012
From: VALEANT INTERNATIONAL (BARBADOS) SRL
To: VALEANT INTERNATIONAL BERMUDA
Reel/Frame 028757/0052 →
SECURITY AGREEMENT Recorded Jul 18, 2011
From: VALEANT INTERNATIONAL (BARBADOS) SRL, A BARBADOS INTERNATIONAL SOCIETY WITH RESTRICTED LIABILITY; BIOVALE LABORATORIES INTERNATIONAL (BARBADOS) SRL, A BARBADOS INTERNATIONAL SOCIETY WITH RESTRICTED LIABILITY
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 026605/0801 →
CHANGE OF NAME Recorded Jun 7, 2011
From: BIOVAIL LABORATORIES INTERNATIONAL SRL
To: VALEANT INTERNATIONAL (BARBADOS) SRL
Reel/Frame 026404/0095 →
PATENT SECURITY RELEASE AGREEMENT Recorded Mar 14, 2011
From: GOLDMAN SACHS LENDING PARTNERS LLC
To: BIOVAIL INTERNATIONAL LABORATORIES SRL; BIOVAIL INTERNATIONAL LABORATORIES (BARBADOS) SRL
Reel/Frame 025950/0073 →
RELEASE OF SECURITY AGREEMENT Recorded Oct 6, 2010
From: JPMORGAN CHASE BANK, N.A., TORONTO BRANCH
To: BIOVAIL CORPORATION; BIOVAIL LABORATORIES INTERNATIONAL SRL
Reel/Frame 025095/0479 →
SECURITY AGREEMENT Recorded Oct 4, 2010
From: BIOVAIL INTERNATIONAL LABORATORIES SRL; BIOVAIL INTERNATIONAL LABORATORIES (BARBADOS) SRL
To: GOLDMAN SACHS LENDING PARTNERS LLC, AS COLLATERAL AGENT
Reel/Frame 025084/0022 →
PATENT AND TRADEMARK SECURITY AGREEMENT Recorded Jun 11, 2009
From: BIOVAIL LABORATORIES INTERNATIONAL SRL
To: J.P. MORGAN CHASE BANK, N.A., TORONTO BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 022813/0195 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 3, 2009
From: FRISBEE, STEVEN
To: BIOVAIL LABORATORIES INTERNATIONAL S.R.L.
Reel/Frame 022335/0655 →