CA2421114A1 - 5-asa derivatives having anti-inflammatory and antibiotic activity and methods of treating diseases therewith - Google Patents
5-asa derivatives having anti-inflammatory and antibiotic activity and methods of treating diseases therewith Download PDFInfo
- Publication number
- CA2421114A1 CA2421114A1 CA002421114A CA2421114A CA2421114A1 CA 2421114 A1 CA2421114 A1 CA 2421114A1 CA 002421114 A CA002421114 A CA 002421114A CA 2421114 A CA2421114 A CA 2421114A CA 2421114 A1 CA2421114 A1 CA 2421114A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- pharmaceutical composition
- hydroxy
- disease
- phenylazo
- Prior art date
- 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.)
- Granted
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Abstract
Compounds are disclosed represented by the following formula (I): where R1 i s a substituted or unsubstituted phenyl group, and where Z is selected such th at a compound, Z-R1-NH2, formed by cleavage of the azo bond is a non-absorbable antibiotic; or an ester or pharmacologically acceptable salt of the compound of formula (I). Compounds of the present invention may be utilized for the prophylaxis or treatment of various diseases including, but not limited to, intestinal diseases such as inflammatory bowel disease and/or traveler's diarrhea, liver diseases such as hepatic encephalopathy, and/or diseases treatable by a non-absorbable antibiotic.
Claims (60)
1. A compound of the formula:
where X is~SO2~or~CO~and Y is:
where n is an integer from 1 to 3;
or the esters or pharmacologically acceptable salts thereof.
where X is~SO2~or~CO~and Y is:
where n is an integer from 1 to 3;
or the esters or pharmacologically acceptable salts thereof.
2. The compound according to Claim 1, wherein X is ~SO2~ and Y is:
where n is an integer from 1 to 3.
where n is an integer from 1 to 3.
3. The compound according to Claim 1, 5-[4-(2-carboxy-acetylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
4. The compound according to Claim 1,5-[4-(4-carboxy-butyrylsulfoamoyl)-phenylazo]-2-hydroxy-benzoic acid.
5. The compound according to Claim 1,5-[4-(3-carboxy-propionylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
6. A pharmaceutical composition for the treatment of an intestinal disease in subjects in need of such treatment, comprising an amount effective to treat the intestinal bowel disease of a compound of the formula:
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof, in admixture with a solid or liquid pharmaceutical diluent or carrier.
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof, in admixture with a solid or liquid pharmaceutical diluent or carrier.
7. The pharmaceutical composition according to Claim 6, wherein X is ~SO2~ and Y is:
where n is an integer from 1 to 3.
where n is an integer from 1 to 3.
8. The pharmaceutical composition according to Claim 6, wherein the compound is 5-[4-(2-carboxy-acetylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
9. The pharmaceutical composition according to Claim 6, wherein the compound is 5-[4-(4-carboxy-butyrylsulfoamoyl)-phenylazo]-2-hydroxy-benzoic acid.
10. The pharmaceutical composition according to Claim 6, wherein the compound is 5-[4-(3-carboxy-propionylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
11. A method of treating an intestinal disease in a subject in need of such treatment, said method comprising administering to the subject an amount effective to treat the intestinal disease of a compound having the following formula:
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof.
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof.
12. The method according to Claim 11, wherein X is ~SO2~ and Y is:
where n is an integer from 1 to 3.
where n is an integer from 1 to 3.
13. The method according to Claim 11, wherein the compound is 5-[4-(2-carboxy-acetylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
14. The method according to Claim 11, wherein the compound is 5-[4-(4-carboxy-butyrylsulfoamoyl)-phenylazo]-2-hydroxy-benzoic acid.
15. The method according to Claim 11, wherein the compound is 5-[4-(3-carboxy-propionylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
16. The method according to Claim 11, wherein the intestinal disease is Crohn's disease.
17. The method according to Claim 11, wherein the intestinal disease is ulcerative colitis.
18. The method according to Claim 11, wherein the intestinal disease is traveler's diarrhea.
19. A pharmaceutical composition for the treatment of a liver disease in subjects in need of such treatment, comprising an amount effective to treat the liver disease of a compound of the formula:
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof, in admixture with a solid or liquid pharmaceutical diluent or carrier.
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof, in admixture with a solid or liquid pharmaceutical diluent or carrier.
20. The pharmaceutical composition according to Claim 19, wherein X is ~SO2~ and Y is:
where n is an integer from 1 to 3.
where n is an integer from 1 to 3.
21. The pharmaceutical composition according to Claim 19, wherein the compound is 5-[4-(2-carboxy-acetylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
22. The pharmaceutical composition according to Claim 19, wherein the compound is 5-[4-(4-carboxy-butyrylsulfoamoyl)-phenylazo]-2-hydroxy-benzoic acid.
23. The pharmaceutical composition according to Claim 19, wherein the compound is 5-[4-(3-carboxy-propionylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
24. A method of treating a liver disease in a subject in need of such treatment, said method comprising administering to the subject an amount effective to treat the liver disease of a compound having the following formula:
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof.
where X is ~SO2~or~CO~ and Y is:
where n is an integer from 1 to 3;
or an ester or pharmacologically acceptable salt thereof.
25. The method according to Claim 24, wherein X is ~SO2~ and Y is:
26 where n is an integer from 1 to 3.
26. The method according to Claim 24, wherein the compound is 5-[4-(2-carboxy-acetylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
26. The method according to Claim 24, wherein the compound is 5-[4-(2-carboxy-acetylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
27. The method according to Claim 24, wherein the compound is 5-[4-(4-carboxy-butyrylsulfoamoyl)-phenylazo]-2-hydroxy-benzoic acid.
28. The method according to Claim 24, wherein the compound is 5-[4-(3-carboxy-propionylsulfamoyl)-phenylazo]-2-hydroxy-benzoic acid.
29. The method according to Claim 24, wherein the liver disease is hepatic encephalopathy.
30. A compound of the formula:
where R1 is a substituted or unsubstituted phenyl group, and where Z is selected such that a compound, Z-R1-NH2, formed by cleavage of the azo bond is a non-absorbable antibiotic;
or an ester or pharmacologically acceptable salt of the compound of Formula I.
where R1 is a substituted or unsubstituted phenyl group, and where Z is selected such that a compound, Z-R1-NH2, formed by cleavage of the azo bond is a non-absorbable antibiotic;
or an ester or pharmacologically acceptable salt of the compound of Formula I.
31. The compound according to Claim 30, wherein Z is a moiety comprising carbonyl, sulfur, sulfinyl or sulfonyl; and a primary, secondary or tertiary amine.
32. The compound according to Claim 30, wherein Z is a moiety comprising sulfur, sulfinyl or sulfonyl; and a primary, secondary or tertiary amine.
33. The compound according to Claim 30, wherein Z is -X-V, where X is carbonyl, sulfur, sulfinyl or sulfonyl; and V is a moiety comprising a primary, secondary or tertiary amine.
34. The compound according to Claim 33, wherein X is sulfur, sulfinyl or sulfonyl.
35. The compound according to Claim 33, wherein V is -NH-Y, where Y
is selected from the group consisting of:
, where X' is O or S;
, where n = 1 to 10, and X" = O or S; and where R2 is hydrogen or hydroxy, and R3 is selected from the group consisting of:
is selected from the group consisting of:
, where X' is O or S;
, where n = 1 to 10, and X" = O or S; and where R2 is hydrogen or hydroxy, and R3 is selected from the group consisting of:
36. The compound according to Claim 33, wherein V is:
where R4 is substituted or unsubstituted phenyl, and R5 is selected from the group consisting of:
where R6 is a linear or branched alkyl having 1 to 10 carbon atoms.
where R4 is substituted or unsubstituted phenyl, and R5 is selected from the group consisting of:
where R6 is a linear or branched alkyl having 1 to 10 carbon atoms.
37. The compound according to Claim 36, wherein R4 is an unsubstituted phenyl group.
38. The compound according to Claim 36, wherein R6 is a linear or branched alkyl having 1 to 4 carbon atoms.
39. A pharmaceutical composition for the treatment of a disease that is treatable by a non-absorbable antibiotic in subjects in need of such treatment, comprising an amount effective to treat the disease of a compound of the formula:
where R1 is a substituted or unsubstituted phenyl group, and where Z is selected such that a compound, Z-R1-NH2, formed by cleavage of the azo bond is a non-absorbable antibiotic; or an ester or pharmacologically acceptable salt of the compound of Formula I, in admixture with a solid or liquid pharmaceutical diluent or carrier.
where R1 is a substituted or unsubstituted phenyl group, and where Z is selected such that a compound, Z-R1-NH2, formed by cleavage of the azo bond is a non-absorbable antibiotic; or an ester or pharmacologically acceptable salt of the compound of Formula I, in admixture with a solid or liquid pharmaceutical diluent or carrier.
40. The pharmaceutical composition according to Claim 39, wherein Z is a moiety comprising carbonyl, sulfur, sulfinyl or sulfonyl; and a primary, secondary or tertiary amine.
41. The pharmaceutical composition according to Claim 39, wherein Z is a moiety comprising sulfur, sulfinyl or sulfonyl; and a primary, secondary or tertiary amine.
42. The pharmaceutical composition according to Claim 39, wherein Z is -X-V, where X is carbonyl, sulfur, sulfinyl or sulfonyl; and V is a moiety comprising a primary, secondary or tertiary amine.
43. The pharmaceutical composition according to Claim 42, wherein X is sulfur, sulfinyl or sulfonyl.
44. The pharmaceutical composition according to Claim 42, wherein V is -NH-Y, where Y is selected from the group consisting of:
, where X' is O or S;
, where n = 1 to 10, and X" = O or S; and where R2 is hydrogen or hydroxy, and R3 is selected from the group consisting of:
, where X' is O or S;
, where n = 1 to 10, and X" = O or S; and where R2 is hydrogen or hydroxy, and R3 is selected from the group consisting of:
45. The pharmaceutical composition according to Claim 42, wherein V is:
where R4 is substituted or unsubstituted phenyl, and R5 is selected from the group consisting of:
where R6 is a linear or branched alkyl having 1 to 10 carbon atoms.
where R4 is substituted or unsubstituted phenyl, and R5 is selected from the group consisting of:
where R6 is a linear or branched alkyl having 1 to 10 carbon atoms.
46. The pharmaceutical composition according to Claim 45, wherein R4 is an unsubstituted phenyl group.
47. The pharmaceutical composition according to Claim 45, wherein R6 is a linear or branched alkyl having 1 to 4 carbon atoms.
48. A method of treating a disease treatable by a non-absorbable antibiotic in a subject in need of such treatment, said method comprising administering to the subject an amount effective to treat the disease of a compound having the following formula:
where R1 is a substituted or unsubstituted phenyl group, and where Z is selected such that a compound, Z-R1-NH2, formed by cleavage of the azo bond is a non-absorbable antibiotic;
or an ester or pharmacologically acceptable salt of the compound of Formula I.
where R1 is a substituted or unsubstituted phenyl group, and where Z is selected such that a compound, Z-R1-NH2, formed by cleavage of the azo bond is a non-absorbable antibiotic;
or an ester or pharmacologically acceptable salt of the compound of Formula I.
49. The method according to Claim 48, wherein Z is a moiety comprising carbonyl, sulfur, sulfinyl or sulfonyl; and a primary, secondary or tertiary amine.
50. The method according to Claim 48, wherein Z is a moiety comprising sulfur, sulfinyl or sulfonyl; and a primary, secondary or tertiary amine.
51. The method according to Claim 48, wherein Z is X-V, where X is carbonyl, sulfur, sulfonyl or sulfonyl; and V is a moiety comprising a primary, secondary or tertiary amine.
52. The method according to Claim 51, wherein X is sulfur, sulfinyl or sulfonyl.
53. The method according to Claim 51, wherein V is -NH-Y, where Y is selected from the group consisting of:
, where X' is O or S;
, where n = 1 to 10, and X" = O or S; and where R2 is hydrogen or hydroxy, and R3 is selected from the group consisting of:
, where X' is O or S;
, where n = 1 to 10, and X" = O or S; and where R2 is hydrogen or hydroxy, and R3 is selected from the group consisting of:
54. The method according to Claim 51, wherein V is:
where R4 is substituted or unsubstituted phenyl, and R5 is selected from the group consisting of:
where R6 is a linear or branched alkyl having 1 to 10 carbon atoms.
where R4 is substituted or unsubstituted phenyl, and R5 is selected from the group consisting of:
where R6 is a linear or branched alkyl having 1 to 10 carbon atoms.
55. The method according to Claim 54, wherein R4 is an unsubstituted phenyl group.
56. The method according to Claim 54, wherein R6 is a linear or branched alkyl having 1 to 4 carbon atoms.
57. The method according to Claim 48, wherein the disease is Crohn's disease.
58. The method according to Claim 48, wherein the disease is ulcerative colitis.
59. The method according to Claim 48, wherein the disease is traveler's diarrhea.
60. The method according to Claim 48, wherein the disease is hepatic encephalopathy.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22868200P | 2000-08-29 | 2000-08-29 | |
| US60/228,682 | 2000-08-29 | ||
| PCT/US2001/041910 WO2002018330A1 (en) | 2000-08-29 | 2001-08-28 | 5-asa derivatives having anti-inflammatory and antibiotic activity and methods of treating diseases therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2421114A1 true CA2421114A1 (en) | 2002-03-07 |
| CA2421114C CA2421114C (en) | 2010-12-07 |
Family
ID=22858177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2421114A Expired - Lifetime CA2421114C (en) | 2000-08-29 | 2001-08-28 | 5-asa derivatives having anti-inflammatory and antibiotic activity and methods of treating diseases therewith |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6458776B1 (en) |
| EP (1) | EP1313699B1 (en) |
| JP (1) | JP5112595B2 (en) |
| AT (1) | ATE460394T1 (en) |
| AU (1) | AU2001285489A1 (en) |
| CA (1) | CA2421114C (en) |
| DE (1) | DE60141520D1 (en) |
| IL (2) | IL154537A0 (en) |
| MX (1) | MXPA03001786A (en) |
| WO (1) | WO2002018330A1 (en) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60115465T2 (en) | 2000-08-29 | 2006-08-03 | Nobex Corp. | IMMUNO-REGULATING COMPOUNDS, DERIVATIVES AND THEIR USE |
| US8048924B2 (en) | 2001-08-29 | 2011-11-01 | Biocon Limited | Methods and compositions employing 4-aminophenylacetic acid compounds |
| JP2006510586A (en) * | 2002-08-29 | 2006-03-30 | ユニバーシティー オブ サザンプトン | Methods of using apoptosis inducers in the preparation of drugs for the treatment of liver disease |
| EP1603556A2 (en) * | 2003-03-06 | 2005-12-14 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Sod mimic multifunctional compounds for treating inflammatory bowel disease |
| SE0300807L (en) * | 2003-03-25 | 2004-03-30 | Sven Kindblom | Shock absorber for height adjustment |
| BRPI0412265A (en) | 2003-07-23 | 2006-09-05 | Novartis Ag | use of calcitonin in osteoarthritis |
| JP2007520495A (en) | 2004-02-06 | 2007-07-26 | ボロディー トーマス ユリウス | Use of aminosalicylic acid in diarrhea-type irritable bowel syndrome |
| JP5009152B2 (en) * | 2004-05-28 | 2012-08-22 | サリックス ファーマシューティカルズ， インコーポレイテッド | Prevention, treatment, and recovery of radiation-induced enteritis |
| DK1773767T3 (en) | 2004-07-07 | 2016-03-21 | Biocon Ltd | Synthesis of azo bound in immune regulatory relations |
| US7498355B2 (en) * | 2005-05-27 | 2009-03-03 | Antibe Therapeutics Inc. | Derivatives of 4- or 5-aminosalicylic acid |
| US7741359B2 (en) * | 2005-05-27 | 2010-06-22 | Antibe Therapeutics Inc. | Hydrogen sulfide derivatives of non-steroidal anti-inflammatory drugs |
| US20060270635A1 (en) * | 2005-05-27 | 2006-11-30 | Wallace John L | Derivatives of 4- or 5-aminosalicylic acid |
| WO2006125293A1 (en) * | 2005-05-27 | 2006-11-30 | Antibe Therapeutics Inc. | Derivatives of 4- or 5-aminosalicylic acid |
| CN101247812A (en) * | 2005-08-24 | 2008-08-20 | 萨利克斯药品公司 | Balsalazide formulations and manufacture and use thereof |
| US8921344B2 (en) * | 2006-11-03 | 2014-12-30 | Salix Pharmaceuticals, Inc. | Formulations and uses of 2-hydroxy-5-phenylazobenzoic acid derivatives |
| US7452872B2 (en) | 2005-08-24 | 2008-11-18 | Salix Pharmaceuticals, Inc. | Formulations and uses of 2-hydroxy-5-phenylazobenzoic acid derivatives |
| EP1951207A2 (en) | 2005-11-17 | 2008-08-06 | Novartis AG | Pharmaceutical composition |
| EP1996710B1 (en) * | 2006-03-09 | 2019-08-14 | Salix Pharmaceuticals, Inc. | Rifaximin anti-rectal dysfunction preparation |
| JP5421098B2 (en) * | 2006-06-06 | 2014-02-19 | ジーアイケア ファーマ インク． | Trimebutine and N-demethylated trimebutine salts |
| US7271253B1 (en) * | 2006-08-10 | 2007-09-18 | Apotex Pharmachem Inc. | Safe process for the preparation of balsalazide |
| JPWO2008114831A1 (en) * | 2007-03-20 | 2010-07-08 | 国立大学法人 岡山大学 | Antibacterial agent having sulfonamide group |
| US20090098088A1 (en) * | 2007-10-10 | 2009-04-16 | The Procter & Gamble Company | Methods And Kits For The Treatment Of Diverticular Conditions |
| BRPI0911998A2 (en) * | 2008-05-01 | 2015-10-13 | Procter & Gamble | Methods and Kits for the Treatment of Inflammatory Bowel Disorder Conditions |
| CN105348184B (en) * | 2015-11-26 | 2020-12-29 | 苏州统华药品有限公司 | Preparation method of sulfasalazine |
| CN111511350B (en) | 2017-07-07 | 2023-10-13 | 埃皮辛特瑞柯斯公司 | Compositions for parenteral administration of therapeutic agents |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2270676A (en) * | 1936-08-20 | 1942-01-20 | Winthrop Chem Co Inc | Sulphonic acid amide compound |
| US2396145A (en) * | 1940-12-14 | 1946-03-05 | Pharmscia Ab | Heterocyclic sulphonamido azo compounds |
| BE791889A (en) * | 1971-11-26 | 1973-05-24 | Pharmacia Ab | NEW DERIVATIVES OF PYRIDINE |
| JPS5353449A (en) * | 1976-10-22 | 1978-05-15 | Sofuia Kk | Picture type pachinko game machine |
| US4412992A (en) * | 1980-07-21 | 1983-11-01 | Biorex Laboratories Limited | 2-Hydroxy-5-phenylazobenzoic acid derivatives and method of treating ulcerative colitis therewith |
| SU1011126A1 (en) * | 1981-07-14 | 1983-04-15 | Всесоюзный научно-исследовательский и испытательный институт медицинской техники | Method of treating diabetes mellitus |
| CS142691A3 (en) * | 1991-05-15 | 1992-11-18 | Vyzk Ustav Farm Biochem Sp | Process for preparing 5-//4-/(4',6'-dimethyl-2-pyrimidinyl)sulfamoyl/phenyl/azo/-acetylsalicylic acid |
| SE9700934D0 (en) * | 1997-03-14 | 1997-03-14 | Astra Ab | New formulation |
-
2001
- 2001-08-28 DE DE60141520T patent/DE60141520D1/en not_active Expired - Lifetime
- 2001-08-28 JP JP2002523448A patent/JP5112595B2/en not_active Expired - Fee Related
- 2001-08-28 MX MXPA03001786A patent/MXPA03001786A/en unknown
- 2001-08-28 IL IL15453701A patent/IL154537A0/en unknown
- 2001-08-28 AU AU2001285489A patent/AU2001285489A1/en not_active Abandoned
- 2001-08-28 CA CA2421114A patent/CA2421114C/en not_active Expired - Lifetime
- 2001-08-28 EP EP01964654A patent/EP1313699B1/en not_active Expired - Lifetime
- 2001-08-28 AT AT01964654T patent/ATE460394T1/en not_active IP Right Cessation
- 2001-08-28 WO PCT/US2001/041910 patent/WO2002018330A1/en active Application Filing
- 2001-08-29 US US09/942,510 patent/US6458776B1/en not_active Expired - Lifetime
-
2003
- 2003-02-19 IL IL154537A patent/IL154537A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2421114C (en) | 2010-12-07 |
| AU2001285489A1 (en) | 2002-03-13 |
| EP1313699B1 (en) | 2010-03-10 |
| US20020111334A1 (en) | 2002-08-15 |
| US6458776B1 (en) | 2002-10-01 |
| IL154537A0 (en) | 2003-09-17 |
| EP1313699A1 (en) | 2003-05-28 |
| JP2004507521A (en) | 2004-03-11 |
| WO2002018330A1 (en) | 2002-03-07 |
| DE60141520D1 (en) | 2010-04-22 |
| ATE460394T1 (en) | 2010-03-15 |
| MXPA03001786A (en) | 2003-06-04 |
| IL154537A (en) | 2013-07-31 |
| JP5112595B2 (en) | 2013-01-09 |
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Effective date: 20210830 |