CA2492718A1 - Prodrugs of proton pump inhibitors - Google Patents
Prodrugs of proton pump inhibitors Download PDFInfo
- Publication number
- CA2492718A1 CA2492718A1 CA002492718A CA2492718A CA2492718A1 CA 2492718 A1 CA2492718 A1 CA 2492718A1 CA 002492718 A CA002492718 A CA 002492718A CA 2492718 A CA2492718 A CA 2492718A CA 2492718 A1 CA2492718 A1 CA 2492718A1
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- CA
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- Prior art keywords
- compound
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- formula
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- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Abstract
Prodrugs of proton pump inhibitors of Formulas 1 through 4, (I-IV), where the symbols are as defined in the specification, and the R group includes at least one acidic group or its pharmaceutically acceptable salt, have improved aqueous solubility and bioavailability.
Claims (36)
1. A compound of Formula 1, Formula 2, Formula 3 or of Formula 4 or isomers of the compounds of Formulas 2 and 3 where the OCH3, and HF2CO groups, respectively are linked to the 6 position of the benzimidazole ring, and wherein R represents the groups selected from Formulas (i) through (viii);
the dashed line represents the bond connecting the R group with the SO2 group, Y is a straight chained or branch-chained disubstituted alkyl group of 1 to 8 carbons, or Y is N;
R1 and R2 independently are H, a straight chained or branch-chained di- or trisubstituted alkyl group of 1 to 12 carbons including 1 or two R5 groups, or a straight chained or branch-chained saturated hydrocarbon skeleton having no more than 12 carbons including 1 or two R5 groups and optionally further including one to three X groups where X is independently selected from the group consisting of-O-, -S-, -NR6-, -NHCO-, -CONH-, -CONHCO-, -COO-, -OCO- and a disubstituted phenyl group which can optionally be substituted with one or two halogen atoms or with one or two R3 groups; or the R5 group is directly attached without an intervening R1 or R2 group to the aromatic or heteroaromatic ring or to the Y group of formulas (i) through (viii);
R3 and R4 independently are H, alkyl of 1 to 3 carbons, fluoroalkyl of 1 to 3 carbons, O-alkyl of 1 to 3 carbons, O-fluoroalkyl of 1 to 3 carbons, S-alkyl of 1 to 3 carbons, S-fluoroalkyl of 1 to 3 carbons;
R5 is independently H, COOH or a tetrazole moiety;
R6 is H or alkyl of 1 to 3 carbons;
with the provisos that at least one the R5 and R2 groups is not H, and at least one R5 is not H and no more than two R5 groups are COOH or tetrazole whereby the compound includes at least one but no more than two COOH or tetrazole groups;
when Y is -N then neither of the R1 and R2 groups is H, or a pharmaceutically acceptable salt of said compound.
the dashed line represents the bond connecting the R group with the SO2 group, Y is a straight chained or branch-chained disubstituted alkyl group of 1 to 8 carbons, or Y is N;
R1 and R2 independently are H, a straight chained or branch-chained di- or trisubstituted alkyl group of 1 to 12 carbons including 1 or two R5 groups, or a straight chained or branch-chained saturated hydrocarbon skeleton having no more than 12 carbons including 1 or two R5 groups and optionally further including one to three X groups where X is independently selected from the group consisting of-O-, -S-, -NR6-, -NHCO-, -CONH-, -CONHCO-, -COO-, -OCO- and a disubstituted phenyl group which can optionally be substituted with one or two halogen atoms or with one or two R3 groups; or the R5 group is directly attached without an intervening R1 or R2 group to the aromatic or heteroaromatic ring or to the Y group of formulas (i) through (viii);
R3 and R4 independently are H, alkyl of 1 to 3 carbons, fluoroalkyl of 1 to 3 carbons, O-alkyl of 1 to 3 carbons, O-fluoroalkyl of 1 to 3 carbons, S-alkyl of 1 to 3 carbons, S-fluoroalkyl of 1 to 3 carbons;
R5 is independently H, COOH or a tetrazole moiety;
R6 is H or alkyl of 1 to 3 carbons;
with the provisos that at least one the R5 and R2 groups is not H, and at least one R5 is not H and no more than two R5 groups are COOH or tetrazole whereby the compound includes at least one but no more than two COOH or tetrazole groups;
when Y is -N then neither of the R1 and R2 groups is H, or a pharmaceutically acceptable salt of said compound.
2. A compound in accordance with Claim 1 which has the structure in accordance with Formula 1.
3. A compound in accordance with Claim 1 which has the structure in accordance with Formula 2.
4. A compound in accordance with Claim 1 which has the structure in accordance with Formula 3.
5. A compound in accordance with Claim 1 which has the structure in accordance with Formula 4.
6. A compound in accordance with Claim 1 where R5 is independently selected from H and COON, or a pharmaceutically acceptable salt of said compound.
7. A compound in accordance with Claim 1 where the formula includes at least one X group.
8. A compound in accordance with Claim 1 where at least one X is O.
9. A compound in accordance with Claim 1 where at least one X is CONH.
10. A compound in accordance with Claim 1 having two R5 groups which represent COOH, or a pharmaceutically acceptable salt of said compound.
11. A compound in accordance with Claim 1 where R represents formula (i).
12. A compound in accordance with Claim 1 wherein Formula 1 has the structure of Formula 1a, Formula 2 has the structure of Formula 2a, Formula 3 has the structure of Formula 3a and Formula 4 has the structure of Formula 4a or isomers of the compounds of Formulas 2a and 3a where the OCH3, and HF2CO groups, respectively are linked to the 6 position of the benzimidazole ring, R1 and R2 independently are H, a straight chained or branch-chained di- or trisubstituted alkyl group of 1 to 12 carbons including 1 or two R5 groups, or a straight chained or branch-chained saturated hydrocarbon skeleton having no more than 12 carbons including 1 or two R5 groups and optionally further including one to three X groups where X is independently selected from the group consisting of -O-, -S-, -NR6-, -NHCO-, -CONH-, -CONHCO-, -COO-, -OCO- and a disubstituted phenyl group which can optionally be substituted with one or two halogen atoms or with one or two R3 groups; or the R5 group is directly attached without an intervening R1 or R2 group to the aromatic ring ;
R5 is independently H or COOH;
with the provisos that at least one the R1 and R2 groups is not H, and at least one R5 is not H and no more than two R5 groups are COOH whereby the compound includes at least one but no more than two COOH groups;
or a pharmaceutically acceptable salt of said compound.
R5 is independently H or COOH;
with the provisos that at least one the R1 and R2 groups is not H, and at least one R5 is not H and no more than two R5 groups are COOH whereby the compound includes at least one but no more than two COOH groups;
or a pharmaceutically acceptable salt of said compound.
13. A compound in accordance with Claim 12 that has Formula 1a.
14. A compound in accordance with Claim 12 that has Formula 2a.
15. A compound in accordance with Claim 14 where the CH3O group is in the 5 position of the benzimidazole moiety.
16. A compound in accordance with Claim 12 that has Formula 3a.
17. A compound in accordance with Claim 14 where the HF2CO group is in the 5 position of the benzimidazole moiety.
18. A compound in accordance with Claim 12 that has Formula 4a.
19. A compound in accordance with Claim 12 that includes only one COOH group, or its pharmaceutically acceptable salt.
20. A compound in accordance with Claim 12 that includes only two COOH groups, or its pharmaceutically acceptable salt.
21. A compound in accordance with Claim 12 where R2, R3 and R4 are hydrogen and R1 is OCH2COOH attached in the 4 position on the phenyl ring relative to the sulfonyl group, or its pharmaceutically acceptable salt.
22. A compound in accordance with Claim 1 wherein Formula 1, Formula 2, Formula 3 or of Formula 4 are further defined as shown below or isomers of the compounds of Formulas 2 and 3 where the OCH3, and HF2CO groups, respectively are linked to the 6 position of the benzimidazole ring, and wherein R represents the groups selected from Formulas (a) through (s), the dashed line represents the bond connecting the R group with the SO2 group, or a pharmaceutically acceptable salt of said compound.
23. A compound in accordance with Claim 22 of Formula 1.
24. A compound in accordance with Claim 22 of Formula 2.
25. A compound in accordance with Claim 24 where the CH3O group is in the 5 position of the benzimidazole moiety.
26. A compound in accordance with Claim 22 of Formula 3.
27. A compound in accordance with Claim 26 where the HF2O group is in the 5 position of the benzimidazole moiety.
28. A compound in accordance with Claim 22 of Formula 4.
29. A compound in accordance with Claim 22 that has the formula or a pharmaceutically acceptable salt of said compound.
30. A compound in accordance with Claim 22 that has the formula or a pharmaceutically acceptable salt thereof
31. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound in accordance with Claim 1.
32. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound in accordance with Claim 12.
33. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound in accordance with Claim 22.
34. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound in accordance with Claim 29.
35. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound in accordance with Claim 30.
36. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound in accordance with Claim 1, 12, 22, 29 or 30 and a proton pump inhibitor drug selected from the groups consisting of the formulas (w), (x) (y) and (z)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39745902P | 2002-07-19 | 2002-07-19 | |
| US60/397,459 | 2002-07-19 | ||
| PCT/US2003/022419 WO2004009583A2 (en) | 2002-07-19 | 2003-07-15 | Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2492718A1 true CA2492718A1 (en) | 2004-01-29 |
| CA2492718C CA2492718C (en) | 2010-12-21 |
Family
ID=30771064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2492718A Expired - Lifetime CA2492718C (en) | 2002-07-19 | 2003-07-15 | Prodrugs of proton pump inhibitors |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US6897227B2 (en) |
| EP (1) | EP1556371B1 (en) |
| JP (1) | JP4463103B2 (en) |
| KR (2) | KR100788778B1 (en) |
| AT (1) | ATE323695T1 (en) |
| AU (1) | AU2003259154B2 (en) |
| BR (1) | BR0312802A (en) |
| CA (1) | CA2492718C (en) |
| CO (1) | CO5690576A2 (en) |
| DE (1) | DE60304726T2 (en) |
| DK (1) | DK1556371T3 (en) |
| ES (1) | ES2263028T3 (en) |
| HK (1) | HK1079207A1 (en) |
| IL (1) | IL166371A0 (en) |
| MX (1) | MXPA05000657A (en) |
| NO (1) | NO20050801L (en) |
| NZ (1) | NZ538221A (en) |
| PL (1) | PL375255A1 (en) |
| PT (1) | PT1556371E (en) |
| RU (1) | RU2292342C2 (en) |
| TW (1) | TW200502231A (en) |
| WO (1) | WO2004009583A2 (en) |
| ZA (1) | ZA200501116B (en) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6852739B1 (en) * | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
| EP1534278A4 (en) * | 2002-08-01 | 2006-09-06 | Nitromed Inc | Nitrosated proton pump inhibitors, compositions and methods of use |
| EP1644352A1 (en) * | 2003-07-15 | 2006-04-12 | Allergan, Inc. | Process for preparing isomerically pure prodrugs of proton pump inhibitors |
| WO2005039640A1 (en) * | 2003-10-03 | 2005-05-06 | Allergan Inc. | Compositions comprising trefoil factor family peptides and/or mucoadhesives and proton pump inhibitor prodrugs |
| US20050075371A1 (en) * | 2003-10-03 | 2005-04-07 | Allergan, Inc. | Methods and compositions for the oral administration of prodrugs of proton pump inhibitors |
| AU2005216862A1 (en) * | 2004-02-18 | 2005-09-09 | Allergan, Inc. | Compositions comprising prodrugs of proton pump inhibitors |
| EP1715854A2 (en) * | 2004-02-18 | 2006-11-02 | Allergan, Inc. | Prodrugs for the intravenous administration of proton pump inhibitors |
| BRPI0507796A (en) * | 2004-03-11 | 2007-07-17 | Allergan Inc | methods and compositions for treating conditions related to gastric acid secretion |
| US7176319B2 (en) | 2004-04-28 | 2007-02-13 | Hetero Drugs Limited | Process for substituted sulfoxides |
| WO2007073301A1 (en) * | 2005-12-23 | 2007-06-28 | Astrazeneca Ab | Benzoimidazole derivatives as prodrugs of proton pump inhibitors |
| WO2007081871A1 (en) * | 2006-01-10 | 2007-07-19 | Allergan, Inc. | Therapeutic salt compositions of sulfonyl ester prodrugs of proton pump inhibitors and methods for their preparation |
| JP2009536195A (en) * | 2006-05-09 | 2009-10-08 | アストラゼネカ・アクチエボラーグ | Parenteral formulations containing proton pump inhibitors sterilized by ionizing radiation in the final container |
| US20070293543A1 (en) * | 2006-06-19 | 2007-12-20 | Edward Lee | THRESHOLD BLOOD OMEPRAZOLE CONCENTRATION IS 50 NG/ML FOR THE MAINTENANCE OF INTRAGASTRIC pH OF AT LEAST 4.0 AFTER ORAL DOSING WITH CMA-OMEPRAZOLE, AGN 201904-Z |
| WO2008036211A1 (en) * | 2006-09-19 | 2008-03-27 | Alevium Pharmaceuticals, Inc. | Prodrugs of proton pump inhibitors including the (1h-pyrrol-1-yl)-1h-benzimidazole moiety |
| WO2008036201A1 (en) * | 2006-09-19 | 2008-03-27 | Alevium Pharmaceuticals, Inc. | Prodrugs of proton pump inhibitors including the 1h-imidazo[4,5-b] pyridine moiety |
| KR20090035195A (en) * | 2007-10-05 | 2009-04-09 | 엘지전자 주식회사 | Plasma display apparatus |
| US20100265240A1 (en) * | 2007-10-05 | 2010-10-21 | Lg Electronics Inc. | Plasma display device |
| KR100895333B1 (en) * | 2007-11-01 | 2009-05-07 | 엘지전자 주식회사 | Method for driving plasma display panel and plasma display device thereof |
| WO2012051036A1 (en) | 2010-10-11 | 2012-04-19 | Merck Sharp & Dohme Corp. | Quinazolinone-type compounds as crth2 antagonists |
| EP2661265B1 (en) | 2010-12-23 | 2017-03-08 | Merck Sharp & Dohme Corp. | Quinolines and aza-quinolines as crth2 receptor modulators |
| RU2589709C2 (en) | 2010-12-23 | 2016-07-10 | Мерк Шарп Энд Домэ Корп. | Quinoxalines and azaquinoxalines as crth2 receptor modulators |
| CA2973370A1 (en) * | 2015-01-09 | 2016-07-14 | The Regents Of The University Of California | Compositions and methods for treating gastrointestinal infections |
| CN108997177A (en) * | 2018-09-04 | 2018-12-14 | 邵阳学院 | A kind of method of microwave assisted N- benzenesulfonyl nitrobenzene amine compound synthesis |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US430042A (en) * | 1890-06-10 | Valve | ||
| SE416649B (en) | 1974-05-16 | 1981-01-26 | Haessle Ab | PROCEDURE FOR THE PREPARATION OF SUBSTANCES WHICH PREVENT Gastric acid secretion |
| SE7804231L (en) | 1978-04-14 | 1979-10-15 | Haessle Ab | Gastric acid secretion |
| JPS6150978A (en) | 1984-08-16 | 1986-03-13 | Takeda Chem Ind Ltd | Pyridine derivative and preparation thereof |
| IL76839A (en) | 1984-10-31 | 1988-08-31 | Byk Gulden Lomberg Chem Fab | Picoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| SE8505112D0 (en) | 1985-10-29 | 1985-10-29 | Haessle Ab | NOVEL PHARMACOLOGICAL COMPOUNDS |
| US4758597A (en) | 1987-05-15 | 1988-07-19 | University Patents, Inc. | Carenadiol and derivatives |
| US4965269A (en) | 1989-12-20 | 1990-10-23 | Ab Hassle | Therapeutically active chloro substituted benzimidazoles |
| US5045522A (en) | 1990-03-27 | 1991-09-03 | Phillips Petroleum Company | Absorption composition comprising zinc titanate for removal of hydrogen sulfide from fluid streams |
| ES2140391T3 (en) | 1990-06-20 | 2000-03-01 | Astra Ab | DERIVATIVES OF DIALCOXI-PIRIDINIL-BENCIMIDAZOLE, PROCEDURE FOR ITS PREPARATION AND ITS PHARMACEUTICAL USE. |
| SE9301830D0 (en) | 1993-05-28 | 1993-05-28 | Ab Astra | NEW COMPOUNDS |
| SK281465B6 (en) * | 1994-06-10 | 2001-04-09 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Substituted arylalkylthioalkylthiopyridines, method of their preparation, their use |
| US5708017A (en) | 1995-04-04 | 1998-01-13 | Merck & Co., Inc. | Stable, ready-to-use pharmaceutical paste composition containing proton pump inhibitors |
| US6093734A (en) | 1998-08-10 | 2000-07-25 | Partnership Of Michael E. Garst, George Sachs, And Jai Moo Shin | Prodrugs of proton pump inhibitors |
| BR9912937A (en) * | 1998-08-10 | 2001-05-08 | Partnership Of Michael E Garst | Proton pump inhibitor prodrugs |
| CN1141305C (en) * | 1998-08-12 | 2004-03-10 | 三角药物公司 | Manufacture of 1,3-oxathiolane nucleosides |
| SE0002476D0 (en) | 2000-06-30 | 2000-06-30 | Astrazeneca Ab | New compounds |
| US6599167B2 (en) | 2000-09-27 | 2003-07-29 | Glenn Waltz | Game call holder and amplifying device |
| WO2002030920A1 (en) * | 2000-10-12 | 2002-04-18 | Takeda Chemical Industries, Ltd. | Benzimidazole compounds, process for producing the same and use thereof |
-
2003
- 2003-07-15 JP JP2004523537A patent/JP4463103B2/en not_active Expired - Fee Related
- 2003-07-15 RU RU2005105564/04A patent/RU2292342C2/en not_active IP Right Cessation
- 2003-07-15 BR BR0312802-4A patent/BR0312802A/en not_active IP Right Cessation
- 2003-07-15 ES ES03765694T patent/ES2263028T3/en not_active Expired - Lifetime
- 2003-07-15 MX MXPA05000657A patent/MXPA05000657A/en active IP Right Grant
- 2003-07-15 DK DK03765694T patent/DK1556371T3/en active
- 2003-07-15 AU AU2003259154A patent/AU2003259154B2/en not_active Ceased
- 2003-07-15 EP EP03765694A patent/EP1556371B1/en not_active Expired - Lifetime
- 2003-07-15 US US10/620,252 patent/US6897227B2/en not_active Expired - Lifetime
- 2003-07-15 PT PT03765694T patent/PT1556371E/en unknown
- 2003-07-15 PL PL03375255A patent/PL375255A1/en not_active Application Discontinuation
- 2003-07-15 CA CA2492718A patent/CA2492718C/en not_active Expired - Lifetime
- 2003-07-15 AT AT03765694T patent/ATE323695T1/en not_active IP Right Cessation
- 2003-07-15 DE DE60304726T patent/DE60304726T2/en not_active Expired - Lifetime
- 2003-07-15 KR KR1020057000899A patent/KR100788778B1/en not_active IP Right Cessation
- 2003-07-15 KR KR1020067026729A patent/KR100822981B1/en not_active IP Right Cessation
- 2003-07-15 WO PCT/US2003/022419 patent/WO2004009583A2/en active IP Right Grant
- 2003-07-15 NZ NZ538221A patent/NZ538221A/en unknown
- 2003-11-07 TW TW092131253A patent/TW200502231A/en unknown
-
2005
- 2005-01-18 IL IL16637105A patent/IL166371A0/en unknown
- 2005-01-20 US US11/039,630 patent/US20050182101A1/en not_active Abandoned
- 2005-01-20 US US11/039,631 patent/US20050143423A1/en not_active Abandoned
- 2005-02-08 ZA ZA200501116A patent/ZA200501116B/en unknown
- 2005-02-15 CO CO05013468A patent/CO5690576A2/en not_active Application Discontinuation
- 2005-02-15 NO NO20050801A patent/NO20050801L/en not_active Application Discontinuation
-
2006
- 2006-01-11 HK HK06100445A patent/HK1079207A1/en not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20230717 |