Pseudopolymorphic forms of a HIV protease inhibitor

• US 8,518,987 B2
• Filed: 08/06/2009
• Issued: 08/27/2013
• Est. Priority Date: 05/16/2002
• Status: Expired due to Term

• Current Assignee: Janssen Sciences Ireland Unlimited Company (Johnson & Johnson)
• Original Assignee: Janssen R&D Ireland (Johnson & Johnson)
• Inventors: Vermeersch, Hans Wim Pieter, Thone, Daniel Joseph Christiaan, Janssens, Luc Donne Marie-Louise, Wigerinck, Piet Tom Bert Paul
• Primary Examiner(s): CHANG, CELIA C
• Application Number:
  US12/536,807
• Publication Number:
  US 20100204316A1
• Time in Patent Office: 1,482 Days
• Field of Search: 514/456, 549/396
• US Class Current: 514/456
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 31/18 for HIV
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 493/04 Ortho-condensed systems

Abstract

New pseudopolymorphic forms of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate and processes for producing them are disclosed.

Claims

1. A hydrate of the compound (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[[(4-aminophenyl) sulfonyl] (isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate in which the ratio of the compound to water is about 1:

0.5 to about 1;

3.

9. The hydrate of claim 1 wherein the ratio of the compound to water is about 1:

1 to about 1;

2.

10. The hydrate of claim 1 wherein the ratio of the compound to water is about 1:

0.5.

11. The hydrate of claim 1 wherein the ratio of the compound to water is about 1:

1.

12. The hydrate of claim 1, wherein the ratio of the compound to water is about 1:

2.

13. The hydrate of claim 1 wherein the ratio of the compound to water is about 1:

3.

2. A hydrate having the formula:

3. A composition comprising a hydrate of the compound (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate, in which the ratio of compound to water is about 1:

0.5 to about 1;

3, and an inert carrier.

4. The composition of claim 3 wherein the inert carrier is a pharmaceutically acceptable carrier.

5. The composition of claim 4 wherein the pharmaceutically acceptable carrier is a solid inert carrier.

14. The composition of claim 3 wherein the ratio of the compound to water is about 1:

1 to about 1;

2.

15. The composition of claim 3 wherein the ratio of the compound to water is about 1:

0.5.

16. The composition of claim 3 wherein the ratio of the compound to water is about 1:

1.

17. The composition of claim 3 wherein the ratio of the compound to water is about 1:

2.

18. The composition of claim 3 wherein the ratio of the compound to water is about 1:

3.

19. The composition of claim 3 further comprising amorphous (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[[(4-aminophenyl)sulfonyl](isobutyl)amino]-1-benzyl-2-hydroxypropylcarbamate.

6. A composition comprising a hydrate having the formula:

7. The composition of claim 6 wherein the inert carrier is a pharmaceutically acceptable carrier.

8. The composition of claim 7 wherein the pharmaceutically acceptable carrier is a solid inert carrier.