IP Library Granted Patent US 8,513,275
Granted Patent B2
US 8,513,275 · App. 13/152,804 · Granted Aug 20, 2013

Forms of rifaximin and uses thereof

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 8,513,275
App. No.
13/152,804
Granted
Aug 20, 2013
Kind
B2
Abstract

The present invention relates to new rifaximin forms kappa, theta, rifaximin:piperazine cocrystal 1 and rifaximin:piperazine cocrystal 2, methods of making same and to their use in medicinal preparations and therapeutic methods.

Claims (43)

1. A rifaximin polymorph Form kappa, a rifaximin polymorph Form theta, a rifaximin:piperazine cocrystal 1 or a rifaximin:piperazine cocrystal 2 wherein:

the polymorph Form kappa exhibits an X-ray powder diffraction pattern having characteristic peaks expressed in degrees 2θ at

6.45-6.67, 6.83-6.94 and 7.68-7.78;

6.45-6.67, 6.83-6.94 and 18.46-18.61;

6.45-6.67, 6.83-6.94 and 7.52-7.56;

6.83-6.94, 7.68-7.78 and 18.46-18.61;

6.45-6.67, 6.83-6.94, 7.68-7.78 and 18.46-18.61;

6.83-6.94, 7.52-7.56, 7.68-7.78 and 18.46-18.61;

6.45-6.67, 6.83-6.94, 7.52-7.56, 7.68-7.78 and 18.46-18.61;

6.45-6.67, 6.83-6.94, 7.52-7.56, 7.68-7.78, 8.30-8.34 and 18.46-18.61; or

5.41-5.65, 6.45-6.67, 6.83-6.94, 7.52-7.56, 7.68-7.78, 8.30-8.34 and 18.46-18.61;

the polymorph Form theta exhibits an X-ray powder diffraction pattern having characteristic peaks expressed in degrees 2θ at

5.48, 7.00, 7.75, 8.72, 9.09, or 10.96;

5.48, 7.00, 7.75, 8.72, 9.09, and 10.96;

5.48, 7.00, 7.75, or 5.48, 7.75, and 8.72;

5.48, 7.00, and 8.72;

5.48, 8.72, and 9.09;

5.48, 9.09, and 10.96;

7.75, 8.72, and 9.09;

7.00, 7.75, 8.72, and 10.96;

8.72, 9.09, and 10.96;

7.00, 7.75, 8.72, and 10.96; or

7.00, 8.72, and 10.96;

the rifaximin:piperazine cocrystal 1 exhibits an X-ray powder diffraction pattern having characteristic peaks expressed in degrees 2θ at

5.74, 6.58, 7.49, 8.21, and 9.83;

5.74, 7.49, 8.21, and 9.83;

5.74, 6.58, 8.21, and 9.83;

5.74, 6.58, 7.49, and 9.83; or

5.74, 6.58, 7.49, and 8.21; and

the rifaximin:piperazine cocrystal 2 exhibits an X-ray powder diffraction pattern having characteristic peaks expressed in degrees 2θ at

3.64, 5.58, 6.45, 7.29, 7.60, 8.27, and 9.01;

5.58, 6.45, 7.29, 7.60, 8.27, and 9.01;

3.64, 6.45, 7.29, 7.60, 8.27, and 9.01;

3.64, 5.58, 7.29, 7.60, 8.27, and 9.01;

3.64, 5.58, 6.45, 7.60, 8.27, and 9.01;

3.64, 5.58, 6.45, 7.29, 7.60, and 9.01;

3.64, 5.58, 6.45, 7.29, 7.60, and 8.27; or

3.64, 5.58, 6.45, 7.29, and 7.60.

2. The rifaximin polymorph Form kappa, Form theta, rifaximin:piperazine cocrystal 1 or rifaximin:piperazine cocrystal 2 according to claim 1 , containing less than 5% by weight total impurities.

3. The rifaximin polymorph Form kappa, Form theta, rifaximin:piperazine cocrystal 1 or rifaximin:piperazine cocrystal 2 according to claim 1 , wherein the compound is at least 50% pure, or at least 75% pure, or at least 80% pure, or at least 90% pure, or at least 95% pure, or at least 98% pure.

4. A pharmaceutical composition comprising the rifaximin polymorph Form kappa, Form theta, rifaximin:piperazine cocrystal 1 or rifaximin:piperazine cocrystal 2 according to claim 1 ; and a pharmaceutically acceptable carrier.

5. The composition according to claim 1 , wherein one or more of rifaximin polymorph Form kappa, Form theta, rifaximin:piperazine cocrystal 1 or rifaximin:piperazine cocrystal 2 are formulated as coated or uncoated tablets, hard or soft gelatin capsules, sugar-coated pills, lozenges, wafer sheets, pellets or powders in sealed packets.

6. A process for producing rifaximin polymorph Form kappa of claim 1 , comprising agitating rifaximin polymorph Form a of rifaximin below 60° C. until a precipitate results; and filtering said precipitate.

Assignments (19)
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: 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 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: THE BANK OF NEW YORK MELLON
Reel/Frame 071564/0463 →
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 →
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 25, 2019
From: SALIX PHARMACEUTICALS, LTD.
To: SALIX PHARMACEUTICALS, INC.
Reel/Frame 049579/0675 →
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: 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 →
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 Jul 8, 2013
From: WU, YIDUO; PARENT, STEPHAN D.; SCHULTHEISS, NATHAN CARL; BEVILL, MELANIE JANELLE; VLAHOVA, PETINKA; HOUSTON, TRAVIS L.
To: APTUIT, INC.
Reel/Frame 030750/0317 →