ES479994A1 - Novel phthalazine derivative*its manufacture and phosphodiesterase cardiac stimulant comprising it - Google Patents
Novel phthalazine derivative*its manufacture and phosphodiesterase cardiac stimulant comprising itInfo
- Publication number
- ES479994A1 ES479994A1 ES479994A ES479994A ES479994A1 ES 479994 A1 ES479994 A1 ES 479994A1 ES 479994 A ES479994 A ES 479994A ES 479994 A ES479994 A ES 479994A ES 479994 A1 ES479994 A1 ES 479994A1
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- cardiac
- doses
- phosphodiesterase
- atoms
- 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.)
- Expired
Links
- 239000000496 cardiotonic agent Substances 0.000 title abstract 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 title 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 title 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 abstract 1
- 206010007556 Cardiac failure acute Diseases 0.000 abstract 1
- 206010019280 Heart failures Diseases 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000000747 cardiac effect Effects 0.000 abstract 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 abstract 1
- 101150113676 chr1 gene Proteins 0.000 abstract 1
- 230000008602 contraction Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000002107 myocardial effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 230000033764 rhythmic process Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
Abstract
1-Piperidino-6,7-dialkoxy-phthalazine derivs. of formula (I), their acid addition salts and bioprecursors are new as the separate isomers or their mixtures. In (I), R is lower alkyl Y is joined to the piperidino ring in position 3 or 4 and =-X-(CHR1)m-Z R1=H or lower alkyl m=1 or 2 with the condition that when m=2 then the two R1 groups may be identical or different X=O or a bond with the condition that when m=1 then X= a direct bond Z= -OOCNR4R5, -OOCR3, -N(R2)-CO-R3, -N(R2)-SO2-R3, -N(R2)-CO-NR4R5 or -N(R2)-COOR3 R2=H or lower alkyl R3=lower alkyl, phenethyl, benzyl, phenyl or 2-, 3- or 4-pyridyl and R4, R5 independently=H or an R3 group. Lower group = =6C atoms pref. =4C atoms and are opt. branched. (I) phosphodiesterase inhibitors and cardiac stimulants which selectively increase myocardial contraction force without accelerating cardiac rhythm. They are used therapeutically or prophylactically for the treatment of cardiac insufficiency, in daily oral doses of 20mg-1g as 2-4 unit doses or in the case of acute cardiac insufficiency they are administered intravenously in doses of 1-300mg.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4567077 | 1977-11-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES479994A1 true ES479994A1 (en) | 1980-08-16 |
Family
ID=10438118
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES474764A Pending ES474764A0 (en) | 1977-11-03 | 1978-11-02 | A PROCEDURE FOR THE PREPARATION OF PHTHALAZINES. |
| ES479992A Expired ES479992A1 (en) | 1977-11-03 | 1979-04-26 | Novel phthalazine derivative*its manufacture and phosphodiesterase cardiac stimulant comprising it |
| ES479993A Expired ES479993A1 (en) | 1977-11-03 | 1979-04-26 | A PROCEDURE FOR THE PREPARATION OF PHTHALAZINES. |
| ES479994A Expired ES479994A1 (en) | 1977-11-03 | 1979-04-26 | Novel phthalazine derivative*its manufacture and phosphodiesterase cardiac stimulant comprising it |
| ES479991A Expired ES479991A1 (en) | 1977-11-03 | 1979-04-26 | A PROCEDURE FOR THE PREPARATION OF PHTHALAZINES. |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES474764A Pending ES474764A0 (en) | 1977-11-03 | 1978-11-02 | A PROCEDURE FOR THE PREPARATION OF PHTHALAZINES. |
| ES479992A Expired ES479992A1 (en) | 1977-11-03 | 1979-04-26 | Novel phthalazine derivative*its manufacture and phosphodiesterase cardiac stimulant comprising it |
| ES479993A Expired ES479993A1 (en) | 1977-11-03 | 1979-04-26 | A PROCEDURE FOR THE PREPARATION OF PHTHALAZINES. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES479991A Expired ES479991A1 (en) | 1977-11-03 | 1979-04-26 | A PROCEDURE FOR THE PREPARATION OF PHTHALAZINES. |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5498783A (en) |
| AR (3) | AR219561A1 (en) |
| AT (1) | AT365184B (en) |
| AU (1) | AU507007B2 (en) |
| BE (1) | BE871770A (en) |
| CA (1) | CA1114379A (en) |
| DE (1) | DE2847621A1 (en) |
| DK (1) | DK487978A (en) |
| ES (5) | ES474764A0 (en) |
| FI (1) | FI783326A (en) |
| FR (1) | FR2407927A1 (en) |
| IE (1) | IE47481B1 (en) |
| IL (1) | IL55844A (en) |
| IT (1) | IT1101279B (en) |
| LU (1) | LU80458A1 (en) |
| NL (1) | NL7810864A (en) |
| PH (1) | PH14659A (en) |
| PT (1) | PT68734A (en) |
| SE (1) | SE7811322L (en) |
| YU (3) | YU253678A (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6215356U (en) * | 1985-07-15 | 1987-01-29 | ||
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| JP2006525273A (en) * | 2003-05-07 | 2006-11-09 | アクテリオン ファマシューティカルズ リミテッド | Novel piperazine derivatives |
| KR20080065704A (en) | 2005-11-09 | 2008-07-14 | 콤비네이토릭스, 인코포레이티드 | Medical Abnormal Treatment Methods, Compositions, and Kits |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| US7879802B2 (en) | 2007-06-04 | 2011-02-01 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2624828T3 (en) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Guanylate cyclase agonists useful for the treatment of gastrointestinal disorders, inflammation, cancer and others |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| MX357121B (en) | 2011-03-01 | 2018-06-27 | Synergy Pharmaceuticals Inc Star | Process of preparing guanylate cyclase c agonists. |
| WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| US9545446B2 (en) | 2013-02-25 | 2017-01-17 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase and their uses |
| CA2905438A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| EP3004138B1 (en) | 2013-06-05 | 2024-03-13 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| JP6694385B2 (en) | 2013-08-09 | 2020-05-13 | アーデリクス，インコーポレーテッド | Compounds and methods for inhibiting phosphate transport |
| US20200368223A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Methods for inhibiting phosphate transport |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1293565A (en) * | 1969-05-03 | 1972-10-18 | Aspro Nicholas Ltd | Aminophthalazines and pharmaceutical compositions thereof |
-
1978
- 1978-10-24 CA CA314,085A patent/CA1114379A/en not_active Expired
- 1978-10-30 PH PH21752A patent/PH14659A/en unknown
- 1978-10-31 LU LU80458A patent/LU80458A1/en unknown
- 1978-11-01 IL IL55844A patent/IL55844A/en unknown
- 1978-11-01 FI FI783326A patent/FI783326A/en unknown
- 1978-11-01 YU YU02536/78A patent/YU253678A/en unknown
- 1978-11-01 NL NL7810864A patent/NL7810864A/en not_active Application Discontinuation
- 1978-11-01 DK DK487978A patent/DK487978A/en unknown
- 1978-11-01 SE SE7811322A patent/SE7811322L/en unknown
- 1978-11-02 ES ES474764A patent/ES474764A0/en active Pending
- 1978-11-02 AT AT0783978A patent/AT365184B/en not_active IP Right Cessation
- 1978-11-02 FR FR7831063A patent/FR2407927A1/en active Granted
- 1978-11-02 JP JP13569778A patent/JPS5498783A/en active Granted
- 1978-11-02 AU AU41276/78A patent/AU507007B2/en not_active Expired
- 1978-11-02 DE DE19782847621 patent/DE2847621A1/en not_active Ceased
- 1978-11-02 PT PT68734A patent/PT68734A/en unknown
- 1978-11-02 IE IE2166/78A patent/IE47481B1/en unknown
- 1978-11-02 IT IT29369/78A patent/IT1101279B/en active
- 1978-11-03 BE BE191543A patent/BE871770A/en unknown
- 1978-11-10 AR AR274311A patent/AR219561A1/en active
-
1979
- 1979-04-26 ES ES479992A patent/ES479992A1/en not_active Expired
- 1979-04-26 ES ES479993A patent/ES479993A1/en not_active Expired
- 1979-04-26 ES ES479994A patent/ES479994A1/en not_active Expired
- 1979-04-26 ES ES479991A patent/ES479991A1/en not_active Expired
- 1979-11-02 AR AR278749A patent/AR217577A1/en active
- 1979-11-02 AR AR278750A patent/AR217578A1/en active
-
1982
- 1982-03-23 YU YU02115/82A patent/YU211582A/en unknown
- 1982-09-23 YU YU02116/82A patent/YU211682A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7811322L (en) | 1979-05-04 |
| ES479993A1 (en) | 1980-08-16 |
| ES479991A1 (en) | 1980-08-16 |
| FR2407927A1 (en) | 1979-06-01 |
| IL55844A (en) | 1982-05-31 |
| AR217577A1 (en) | 1980-03-31 |
| IE47481B1 (en) | 1984-04-04 |
| JPS5538352B2 (en) | 1980-10-03 |
| IE782166L (en) | 1979-05-03 |
| FR2407927B1 (en) | 1982-07-16 |
| DE2847621A1 (en) | 1979-05-17 |
| AR217578A1 (en) | 1980-03-31 |
| CA1114379A (en) | 1981-12-15 |
| BE871770A (en) | 1979-05-03 |
| IT1101279B (en) | 1985-09-28 |
| YU253678A (en) | 1983-02-28 |
| ES474764A0 (en) | 1980-08-16 |
| YU211682A (en) | 1983-02-28 |
| FI783326A (en) | 1979-05-04 |
| NL7810864A (en) | 1979-05-07 |
| IT7829369A0 (en) | 1978-11-02 |
| DK487978A (en) | 1979-05-04 |
| PH14659A (en) | 1981-10-20 |
| AU507007B2 (en) | 1980-01-31 |
| ATA783978A (en) | 1981-05-15 |
| AT365184B (en) | 1981-12-28 |
| PT68734A (en) | 1978-12-01 |
| AR219561A1 (en) | 1980-08-29 |
| IL55844A0 (en) | 1979-01-31 |
| ES479992A1 (en) | 1980-09-01 |
| JPS5498783A (en) | 1979-08-03 |
| YU211582A (en) | 1983-02-28 |
| LU80458A1 (en) | 1980-05-07 |
| AU4127678A (en) | 1979-05-17 |
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