IP Library Granted Patent US 8,735,419
Granted Patent B2
US 8,735,419 · App. 13/371,238 · Granted May 27, 2014

Forms of rifaximin and uses thereof

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Quick Facts
Patent No.
US 8,735,419
App. No.
13/371,238
Granted
May 27, 2014
Kind
B2
Abstract

Embodiments relate to Rifaximin polymorphic, salt, and hydrate forms, methods of producing polymorphic forms and to their use in medicinal preparations and to therapeutic methods using them.

Claims (28)

1. A rifaximin polymorph Form Mu, or a salt, or hydrate form thereof, having an X-ray powder diffraction comprising peaks, in terms of 2θ, at

two or more of about 4.72, about 4.79, and about 6.29; or

two or more of about 4.72, about 4.79, and about 7.44; or

two or more of about 4.72, about 4.79, and about 8.11; or

two or more of about 4.72, about 8.11, and about 10.32; or

two or more of about 4.72, about 6.94, and about 11.20; or

two or more of about 4.72, about 4.79, and about 12.09; or

two or more of about 4.72, about 4.79, about 6.29, about 6.94, about 7.44, about 7.84, about 8.11, about 8.36, about 8.55, about 8.70, about 8.88, and about 9.60; or

two or more of about 4.72, about 4.79, about 6.29, about 6.94, about 7.44, about 7.84, about 8.11, about 8.36, about 8.55, about 8.70, about 8.88, about 9.60, about 10.15, about 10.32, about 10.88, about 11.02, and about 11.20.

2. A rifaximin polymorph Form Pi, or a salt, or hydrate form thereof, having an X-ray powder diffraction comprising peaks, in terms of 2, at about 6.91, about 7.16, and about 9.15.

3. A rifaximin polymorph Form Omicron, or a salt, or hydrate form thereof, having an X-ray powder diffraction comprising peaks, in terms of 2θ, at

two or more of about 5.87, about 6.99, and about 7.77; or

two or more of about 5.87, about 6.99, and about 8.47; or

two or more of about 5.87, about 6.99, and about 9.13; or

two or more of about 5.87, about 6.99, and about 9.58; or

two or more of about 5.87, about 6.99, and about 9.74; or

two or more of about 5.87, about 6.99, and about 12.35; or

two or more of about 5.87, about 6.99, and about 13.27; or

two or more of about 5.87, about 6.99, and about 13.69.

4. The Form Mu of rifaximin according to claim 1 , wherein the rifaximin Form contains less than 5% by weight impurities.

5. The Form Mu of rifaximin according to claim 1 , wherein one or more of the rifaximin forms is at least 50% pure, at least 75% pure, at least 80% pure, at least 90% pure, at least 95% pure, or at least 98% pure.

6. A pharmaceutical composition comprising the polymorph Form Mu of rifaximin according to claim 1 , the polymorph Form Pi of rifaximin according to claim 2 , or the polymorph Form Omicron according to claim 3 , or a salt, or hydrate form thereof, and a pharmaceutically acceptable carrier.

7. A method of treating a bowel related disorder, comprising administering to a subject in need thereof and effective amount of the polymorph Form Mu of rifaximin according to claim 1 , the polymorph Form Pi of rifaximin according to claim 2 , or the polymorph Form Omicron according to claim 3 , or a salt, or hydrate form thereof.

8. The Form Pi of rifaximin according to claim 2 , wherein the rifaximin Form contains less than 5% by weight impurities.

9. The Form Pi of rifaximin according to claim 2 , wherein one or more of the rifaximin forms is at least 50% pure, at least 75% pure, at least 80% pure, at least 90% pure, at least 95% pure, or at least 98% pure.

10. The Form Omicron of rifaximin according to claim 3 , wherein the rifaximin Form contains less than 5% by weight impurities.

11. The Form Omicron of rifaximin according to claim 3 , wherein one or more of the rifaximin forms is at least 50% pure, at least 75% pure, at least 80% pure, at least 90% pure, at least 95% pure, or at least 98% pure.

12. The pharmaceutical composition according to claim 6 , wherein one or more of the rifaximin forms are formulated as coated or uncoated tablets, hard or soft gelatin capsules, sugar-coated pills, lozenges, wafer sheets, pellets or powders in a sealed packet.

Assignments (19)
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 & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
Reel/Frame 073654/0242 →
RELEASE OF SECURITY INTEREST Recorded Nov 20, 2025
From: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
To: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
Reel/Frame 073637/0126 →
U.S. PATENT SECURITY AGREEMENT Recorded Jun 13, 2025
From: MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; BAUSCH HEALTH US, LLC (F/K/A VALEANT PHARMACEUTICALS NORTH AMERICA LLC); PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; BAUSCH HEALTH AMERICAS, INC.; SOLTA MEDICAL, INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 071566/0200 →
U.S. PATENT SECURITY AGREEMENT Recorded Jun 13, 2025
From: MEDICIS PHARMACEUTICAL CORPORATION; ORAPHARMA, INC.; BAUSCH HEALTH US, LLC (F/K/A VALEANT PHARMACEUTICALS NORTH AMERICA LLC); PRECISION DERMATOLOGY, INC.; SALIX PHARMACEUTICALS, INC.; SANTARUS, INC.; BAUSCH HEALTH AMERICAS, INC.; SOLTA MEDICAL, INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 071564/0463 →
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 (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 AGREEMENT Recorded Feb 10, 2022
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON
Reel/Frame 059121/0001 →
SECURITY INTEREST Recorded Jun 8, 2021
From: BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.; BAUSCH HEALTH AMERICAS, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 056811/0814 →
SECURITY INTEREST Recorded Mar 11, 2019
From: BAUSCH HEALTH AMERICAS, INC.; BAUSCH & LOMB INCORPORATED; BAUSCH HEALTH US, LLC; SOLTA MEDICAL, INC.; MEDICIS PHARMACEUTICAL CORPORATION; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.; ORAPHARMA, INC.; PRECISION DERMATOLOGY, INC.
To: THE BANK OF NEW YORK MELLON, AS NOTES COLLATERAL AGENT
Reel/Frame 048556/0758 →
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 →
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 Jul 19, 2017
From: SALIX PHARMACEUTICALS, LTD
To: THE BANK OF NEW YORK MELLON
Reel/Frame 043041/0880 →
SECURITY AGREEMENT Recorded Apr 2, 2015
From: GLYCYX PHARMACEUTICALS, LTD.; SALIX PHARMACEUTICALS, INC.; SALIX PHARMACEUTICALS, LTD.; SANTARUS, INC.
To: BARCLAYS BANK PLC, AS COLLATERAL AGENT
Reel/Frame 035364/0396 →
RELEASE OF SECURITY INTEREST Recorded Apr 1, 2015
From: JEFFERIES FINANCE LLC
To: SALIX PHARMACEUTICALS, LTD.
Reel/Frame 035353/0661 →
SECURITY AGREEMENT Recorded Jan 2, 2014
From: SALIX PHARMACEUTICALS, LTD.
To: JEFFERIES FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 031896/0752 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2012
From: APTUIT, INC.
To: SALIX PHARMACEUTICALS, LTD.
Reel/Frame 028113/0635 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 26, 2012
From: PARENT, STEPHAN D.; MCQUEEN, LISA L.; ANDRES, PATRICIA; SHIELDS, PAUL; WU, YIDUO; DING, FEI; SMIT, JARED P.
To: APTUIT, INC.
Reel/Frame 028113/0545 →