WO1993015044A1 - Derives d'acide n-benzyloxamique, d'oxamate et d'oxamide et leur utilisation comme inhibiteurs du facteur de necrose tumorale (fnt) et de la phosphodiesterase iv (pde iv) - Google Patents
Derives d'acide n-benzyloxamique, d'oxamate et d'oxamide et leur utilisation comme inhibiteurs du facteur de necrose tumorale (fnt) et de la phosphodiesterase iv (pde iv) Download PDFInfo
- Publication number
- WO1993015044A1 WO1993015044A1 PCT/US1993/000552 US9300552W WO9315044A1 WO 1993015044 A1 WO1993015044 A1 WO 1993015044A1 US 9300552 W US9300552 W US 9300552W WO 9315044 A1 WO9315044 A1 WO 9315044A1
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- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- hydrogen
- methyl
- unsubstituted
- alkyl
- Prior art date
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- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 title claims description 14
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 title claims description 6
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 4
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 title description 2
- GUZSZEGZZYGNJR-UHFFFAOYSA-N 2-(benzylamino)-2-oxoacetic acid Chemical compound OC(=O)C(=O)NCC1=CC=CC=C1 GUZSZEGZZYGNJR-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 91
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 53
- -1 4-tetrahydrothiopyranyl Chemical group 0.000 claims description 51
- 125000001153 fluoro group Chemical group F* 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 25
- 235000019000 fluorine Nutrition 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
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- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 5
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
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- 125000005843 halogen group Chemical group 0.000 claims description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- ONKTWKZNRKLOGH-UHFFFAOYSA-N n'-[(3-cyclopentyloxy-4-methoxyphenyl)methyl]oxamide Chemical compound COC1=CC=C(CNC(=O)C(N)=O)C=C1OC1CCCC1 ONKTWKZNRKLOGH-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
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- 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 claims 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RQCWACORMCNZMP-UHFFFAOYSA-N methyl 2-[[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]methylamino]-2-oxoacetate Chemical compound COC(=O)C(=O)NCC1=CC=C(OC(F)F)C(OCC2CC2)=C1 RQCWACORMCNZMP-UHFFFAOYSA-N 0.000 claims 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
Definitions
- monokine activity such as by inhibition of TNF production
- an HIV-infecte individual aids in enhancing the quality of life of HIV-infected patients by reducing the severity of monokine-mediated disease associated problems such as cachexia and muscle degeneration.
- the present invention also provides a method of preventing a TNF mediated disease state in an animal in need thereof, including humans, by prophylactically administering an effective amount of a compound of Formula (I).
- Ri is C ⁇ _2 alkyl substituted by 1 or more fluorines, CH2-cyclopropyl, CH2-cyclopentyl, cyclopentyl or cyclopentenyl;
- R2 is methyl or fluoro substituted C ⁇ _2 alkyl;
- A is 2-, 3- or 4-pyridyl, 4- morpholinyl, 2-thienyl, 2-imidazole or 4-thiazolyl, each of which may be substituted or unsubstituted by NR 5 R ⁇ g or N 5 C(O)R5;
- R20 is OR5, NR5OR5 or NHCH2A.
- Compounds of Formula (1) are prepared by reacting a compound of Formula (5) wit an appropriately activated oxamic acid derivative of a Formula (6) compound wherein X4 is activating group, well known to those skilled in the art, such as those disclosed in Bodansky 2 Peptide Synthesis, Wiley & Sons, publishers (1976) pages 99-109. More preferred X4 groups are Cl, Br, OCH2CH3, OC(O)CH 3 , OC(O)CF 3 , O-C(O)-OCH 2 CH 3 , O-C(O)- OCH2CH(CH3)2, or O-C(O)-OCH2-C6H5 in the presence of a non-nucleophilic base.
- U-937 cells a human monocyte cell line that has been shown to contain a large amount of PDE IV.
- nondifferentiated U-937 cells approximately 10 ⁇ cells/reaction tube
- PDE inhibitors were incubated with various concentrations (0.01-100 mM) of PDE inhibitors for one minute and 1 mM prostaglandin E2 for an additional four minutes.
- cells were lysed by the addition of 1M potassium carbonate and cAMP content was assessed by RIA.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Cette invention concerne de nouvelles pyrrolidinones de la formule (I) qui inhibent le PDE IV et le FNT.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82724592A | 1992-01-29 | 1992-01-29 | |
| US07/827,245 | 1992-01-29 | ||
| US96800992A | 1992-10-29 | 1992-10-29 | |
| US07/968,009 | 1992-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1993015044A1 true WO1993015044A1 (fr) | 1993-08-05 |
Family
ID=27125082
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1993/000552 WO1993015044A1 (fr) | 1992-01-29 | 1993-01-19 | Derives d'acide n-benzyloxamique, d'oxamate et d'oxamide et leur utilisation comme inhibiteurs du facteur de necrose tumorale (fnt) et de la phosphodiesterase iv (pde iv) |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU3588693A (fr) |
| WO (1) | WO1993015044A1 (fr) |
Cited By (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| US5594106A (en) * | 1993-08-23 | 1997-01-14 | Immunex Corporation | Inhibitors of TNF-α secretion |
| US5665737A (en) * | 1994-10-12 | 1997-09-09 | Euro-Celtique, S.A. | Substituted benzoxazoles |
| US5744473A (en) * | 1996-09-16 | 1998-04-28 | Euro-Celtique, S.A. | PDE IV inhibitors: "bis-compounds" |
| WO1998056756A1 (fr) * | 1997-06-12 | 1998-12-17 | Cheil Jedang Corporation | Derives acides des catecholamines et compositions pharmaceutiques les contenant |
| US5981599A (en) * | 1996-05-01 | 1999-11-09 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor active compounds |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6090816A (en) * | 1994-12-13 | 2000-07-18 | Euro-Celtique S.A. | Aryl thioxanthines |
| US6211244B1 (en) | 1994-10-21 | 2001-04-03 | Nps Pharmaceuticals, Inc. | Calcium receptor-active compounds |
| US6268373B1 (en) | 1995-06-07 | 2001-07-31 | Euro-Celtique S.A. | Trisubstituted thioxanthines |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| WO2002018321A2 (fr) * | 2000-08-29 | 2002-03-07 | Abbott Laboratories | Inhibiteurs de proteine tyrosine phosphatase d'acide amino(oxo)acetique |
| US6627767B2 (en) | 2000-08-29 | 2003-09-30 | Abbott Laboratories | Amino(oxo) acetic acid protein tyrosine phosphatase inhibitors |
| US7153824B2 (en) | 2003-04-01 | 2006-12-26 | Applied Research Systems Ars Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| EP2088154A1 (fr) | 2004-03-09 | 2009-08-12 | Ironwood Pharmaceuticals, Inc. | Procédés et compositions pour le traitement de troubles gastro-intestinaux |
| EP2193808A1 (fr) | 1999-08-21 | 2010-06-09 | Nycomed GmbH | Combinaision synergique |
| WO2011069038A2 (fr) | 2009-12-03 | 2011-06-09 | Synergy Pharmaceuticals, Inc. | Agonistes de la guanylate cyclase utiles dans le traitement de l'hypercholestérolémie, de l'athérosclérose, d'une coronaropathie, des calculs biliaires, de l'obésité et d'autres maladies cardiovasculaires |
| WO2012118972A2 (fr) | 2011-03-01 | 2012-09-07 | Synegy Pharmaceuticals Inc. | Procédé de préparation d'agonistes du guanylate cyclase c |
| WO2013138352A1 (fr) | 2012-03-15 | 2013-09-19 | Synergy Pharmaceuticals Inc. | Formulations d'agonistes de la guanylate cyclase c et procédés d'utilisation |
| WO2014131024A2 (fr) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonistes de la guanylate cyclase et applications associées |
| EP2776395A2 (fr) | 2011-11-09 | 2014-09-17 | Mylan Laboratories, Limited | Procédé pour la préparation de roflumilast |
| WO2014151206A1 (fr) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonistes de la guanylate cyclase et leurs utilisations |
| WO2014151200A2 (fr) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions utiles pour le traitement de troubles gastro-intestinaux |
| EP2810951A2 (fr) | 2008-06-04 | 2014-12-10 | Synergy Pharmaceuticals Inc. | Agonistes de guanylate cyclase utile dans le traitement de troubles gastro-intestinaux, d'une inflammation, d'un cancer et d'autres troubles |
| WO2014197720A2 (fr) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Agonistes ultra-purs de guanylate cyclase c, leur procédé de production et d'utilisation |
| WO2015021358A2 (fr) | 2013-08-09 | 2015-02-12 | Dominique Charmot | Composés et procédés d'inhibition du transport de phosphate |
| EP2998314A1 (fr) | 2007-06-04 | 2016-03-23 | Synergy Pharmaceuticals Inc. | Agonistes de guanylase cyclase utiles pour le traitement de troubles gastro-intestinaux, d'inflammation, de cancer et d'autres troubles |
| US9468598B2 (en) | 2002-02-20 | 2016-10-18 | Astrazeneca Ab | Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient |
| EP3241839A1 (fr) | 2008-07-16 | 2017-11-08 | Synergy Pharmaceuticals Inc. | Agonistes de guanylate cyclase utiles pour le traitement de troubles gastro-intestinaux, inflammatoires, cancéreux et autres |
| WO2020237096A1 (fr) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combinaison pour baisser le phosphate sérique chez un patient |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992000968A1 (fr) * | 1990-07-10 | 1992-01-23 | Smithkline Beecham Corporation | Oxamides |
-
1993
- 1993-01-19 AU AU35886/93A patent/AU3588693A/en not_active Abandoned
- 1993-01-19 WO PCT/US1993/000552 patent/WO1993015044A1/fr active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992000968A1 (fr) * | 1990-07-10 | 1992-01-23 | Smithkline Beecham Corporation | Oxamides |
Cited By (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5594106A (en) * | 1993-08-23 | 1997-01-14 | Immunex Corporation | Inhibitors of TNF-α secretion |
| US5629285A (en) * | 1993-08-23 | 1997-05-13 | Immunex Corporation | Inhibitors of TNF-α secretion |
| US5591776A (en) * | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
| US5665737A (en) * | 1994-10-12 | 1997-09-09 | Euro-Celtique, S.A. | Substituted benzoxazoles |
| US6211244B1 (en) | 1994-10-21 | 2001-04-03 | Nps Pharmaceuticals, Inc. | Calcium receptor-active compounds |
| US6090816A (en) * | 1994-12-13 | 2000-07-18 | Euro-Celtique S.A. | Aryl thioxanthines |
| US6268373B1 (en) | 1995-06-07 | 2001-07-31 | Euro-Celtique S.A. | Trisubstituted thioxanthines |
| US6342532B1 (en) | 1996-05-01 | 2002-01-29 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor active compounds |
| US6710088B2 (en) | 1996-05-01 | 2004-03-23 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| US5981599A (en) * | 1996-05-01 | 1999-11-09 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor active compounds |
| US5744473A (en) * | 1996-09-16 | 1998-04-28 | Euro-Celtique, S.A. | PDE IV inhibitors: "bis-compounds" |
| WO1998056756A1 (fr) * | 1997-06-12 | 1998-12-17 | Cheil Jedang Corporation | Derives acides des catecholamines et compositions pharmaceutiques les contenant |
| EP2193808A1 (fr) | 1999-08-21 | 2010-06-09 | Nycomed GmbH | Combinaision synergique |
| US6627767B2 (en) | 2000-08-29 | 2003-09-30 | Abbott Laboratories | Amino(oxo) acetic acid protein tyrosine phosphatase inhibitors |
| WO2002018321A3 (fr) * | 2000-08-29 | 2003-04-10 | Abbott Lab | Inhibiteurs de proteine tyrosine phosphatase d'acide amino(oxo)acetique |
| WO2002018321A2 (fr) * | 2000-08-29 | 2002-03-07 | Abbott Laboratories | Inhibiteurs de proteine tyrosine phosphatase d'acide amino(oxo)acetique |
| US9468598B2 (en) | 2002-02-20 | 2016-10-18 | Astrazeneca Ab | Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient |
| US7153824B2 (en) | 2003-04-01 | 2006-12-26 | Applied Research Systems Ars Holding N.V. | Inhibitors of phosphodiesterases in infertility |
| EP2088154A1 (fr) | 2004-03-09 | 2009-08-12 | Ironwood Pharmaceuticals, Inc. | Procédés et compositions pour le traitement de troubles gastro-intestinaux |
| EP2998314A1 (fr) | 2007-06-04 | 2016-03-23 | Synergy Pharmaceuticals Inc. | Agonistes de guanylase cyclase utiles pour le traitement de troubles gastro-intestinaux, d'inflammation, de cancer et d'autres troubles |
| EP2810951A2 (fr) | 2008-06-04 | 2014-12-10 | Synergy Pharmaceuticals Inc. | Agonistes de guanylate cyclase utile dans le traitement de troubles gastro-intestinaux, d'une inflammation, d'un cancer et d'autres troubles |
| EP3241839A1 (fr) | 2008-07-16 | 2017-11-08 | Synergy Pharmaceuticals Inc. | Agonistes de guanylate cyclase utiles pour le traitement de troubles gastro-intestinaux, inflammatoires, cancéreux et autres |
| WO2011069038A2 (fr) | 2009-12-03 | 2011-06-09 | Synergy Pharmaceuticals, Inc. | Agonistes de la guanylate cyclase utiles dans le traitement de l'hypercholestérolémie, de l'athérosclérose, d'une coronaropathie, des calculs biliaires, de l'obésité et d'autres maladies cardiovasculaires |
| EP2923706A1 (fr) | 2009-12-03 | 2015-09-30 | Synergy Pharmaceuticals Inc. | Agonistes de guanylate cyclase utiles pour le traitement de l'hypercholestérolémie |
| WO2012118972A2 (fr) | 2011-03-01 | 2012-09-07 | Synegy Pharmaceuticals Inc. | Procédé de préparation d'agonistes du guanylate cyclase c |
| EP2776395A2 (fr) | 2011-11-09 | 2014-09-17 | Mylan Laboratories, Limited | Procédé pour la préparation de roflumilast |
| EP4309673A2 (fr) | 2012-03-15 | 2024-01-24 | Bausch Health Ireland Limited | Formulations d'agonistes de guanylate cyclase c et leurs procédés d'utilisation |
| WO2013138352A1 (fr) | 2012-03-15 | 2013-09-19 | Synergy Pharmaceuticals Inc. | Formulations d'agonistes de la guanylate cyclase c et procédés d'utilisation |
| EP3708179A1 (fr) | 2012-03-15 | 2020-09-16 | Bausch Health Ireland Limited | Formulations d'agonistes de guanylate cyclase c et leurs procédés d'utilisation |
| WO2014131024A2 (fr) | 2013-02-25 | 2014-08-28 | Synergy Pharmaceuticals Inc. | Agonistes de la guanylate cyclase et applications associées |
| EP3718557A2 (fr) | 2013-02-25 | 2020-10-07 | Bausch Health Ireland Limited | Agoniste du récepteur de la guanylate cyclase sp-333 à utiliser lors du nettoyage du côlon |
| WO2014151200A2 (fr) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions utiles pour le traitement de troubles gastro-intestinaux |
| WO2014151206A1 (fr) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonistes de la guanylate cyclase et leurs utilisations |
| WO2014197720A2 (fr) | 2013-06-05 | 2014-12-11 | Synergy Pharmaceuticals, Inc. | Agonistes ultra-purs de guanylate cyclase c, leur procédé de production et d'utilisation |
| EP4424697A2 (fr) | 2013-06-05 | 2024-09-04 | Bausch Health Ireland Limited | Agonistes ultra-purs de guanylate cyclase c, leur procédé de fabrication et d'utilisation |
| WO2015021358A2 (fr) | 2013-08-09 | 2015-02-12 | Dominique Charmot | Composés et procédés d'inhibition du transport de phosphate |
| EP3884935A1 (fr) | 2013-08-09 | 2021-09-29 | Ardelyx, Inc. | Composés et procédés d'inhibition du transport de phosphate |
| EP3492106A1 (fr) | 2013-08-09 | 2019-06-05 | Ardelyx, Inc. | Composés et procédés d'inhibition du transport de phosphate |
| WO2020237096A1 (fr) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combinaison pour baisser le phosphate sérique chez un patient |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3588693A (en) | 1993-09-01 |
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