CZ20011429A3 - Substituované fenyl-alkenoylguanidiny, způsob jejich přípravy, a léčivo nebo diagnostický prostředek, které je obsahují - Google Patents
Substituované fenyl-alkenoylguanidiny, způsob jejich přípravy, a léčivo nebo diagnostický prostředek, které je obsahují Download PDFInfo
- Publication number
- CZ20011429A3 CZ20011429A3 CZ20011429A CZ20011429A CZ20011429A3 CZ 20011429 A3 CZ20011429 A3 CZ 20011429A3 CZ 20011429 A CZ20011429 A CZ 20011429A CZ 20011429 A CZ20011429 A CZ 20011429A CZ 20011429 A3 CZ20011429 A3 CZ 20011429A3
- Authority
- CZ
- Czechia
- Prior art keywords
- alkyl
- group
- hydrogen
- phenyl
- fluorine
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000003814 drug Substances 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000002357 guanidines Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 208000001130 gallstones Diseases 0.000 claims abstract description 10
- 201000001883 cholelithiasis Diseases 0.000 claims abstract description 9
- 238000011321 prophylaxis Methods 0.000 claims abstract description 5
- 238000011282 treatment Methods 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 60
- 229910052731 fluorine Inorganic materials 0.000 claims description 59
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 43
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- -1 CF 3 Chemical group 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 239000011737 fluorine Substances 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 36
- 125000001153 fluoro group Chemical group F* 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 18
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 150000002500 ions Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 13
- 229910001413 alkali metal ion Inorganic materials 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000002632 lipids Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000002253 acid Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- 210000000941 bile Anatomy 0.000 description 11
- 150000004702 methyl esters Chemical class 0.000 description 11
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 235000012000 cholesterol Nutrition 0.000 description 7
- 238000011084 recovery Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- HNBDRPTVWVGKBR-UHFFFAOYSA-N methyl pentanoate Chemical compound CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 5
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
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- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
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- 238000012360 testing method Methods 0.000 description 4
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
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- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
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- 150000001502 aryl halides Chemical class 0.000 description 2
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- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
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- 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
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
- C07J41/0061—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives one of the carbon atoms being part of an amide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Gastroenterology & Hepatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19849722A DE19849722A1 (de) | 1998-10-28 | 1998-10-28 | Substituierte Phenyl-alkenoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20011429A3 true CZ20011429A3 (cs) | 2001-08-15 |
Family
ID=7885948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20011429A CZ20011429A3 (cs) | 1998-10-28 | 1999-10-15 | Substituované fenyl-alkenoylguanidiny, způsob jejich přípravy, a léčivo nebo diagnostický prostředek, které je obsahují |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6166002A (https=) |
| EP (1) | EP1124841B1 (https=) |
| JP (1) | JP4616479B2 (https=) |
| KR (1) | KR20010085973A (https=) |
| CN (1) | CN1325403A (https=) |
| AT (1) | ATE236191T1 (https=) |
| AU (1) | AU757365B2 (https=) |
| BR (1) | BR9914929A (https=) |
| CA (1) | CA2349523A1 (https=) |
| CZ (1) | CZ20011429A3 (https=) |
| DE (2) | DE19849722A1 (https=) |
| DK (1) | DK1124841T3 (https=) |
| ES (1) | ES2191466T3 (https=) |
| HK (1) | HK1041271A1 (https=) |
| HU (1) | HUP0103751A3 (https=) |
| ID (1) | ID29025A (https=) |
| PL (1) | PL348108A1 (https=) |
| PT (1) | PT1124841E (https=) |
| RU (1) | RU2232769C2 (https=) |
| TR (1) | TR200101163T2 (https=) |
| WO (1) | WO2000024761A1 (https=) |
| ZA (1) | ZA200103106B (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19941764A1 (de) | 1999-09-02 | 2001-03-15 | Aventis Pharma Gmbh | Substituierte Acylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikamente oder Diagnostika sowie sie enthaltende Medikamente |
| EP2617709B8 (en) | 2003-06-26 | 2022-12-21 | Biotron Limited | Guanidine derivatives as antiviral agents |
| DE10338554A1 (de) * | 2003-08-22 | 2005-03-31 | Aventis Pharma Deutschland Gmbh | Pentafluorosulfanylphenyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US20050171215A1 (en) * | 2004-01-30 | 2005-08-04 | Ethicon, Inc. | Germicidal compositions containing halogenated phthalaldehyes, and methods of using such compositions for disinfection or sterilization |
| US6891069B1 (en) | 2004-01-30 | 2005-05-10 | Ethicon, Inc. | Synthesis of 4-substituted phthalaldehyde |
| US7476767B2 (en) | 2004-01-30 | 2009-01-13 | Ethicon, Inc. | Alpha-hydroxy sulfonate aldehydes, germicidal compositions containing the alpha-hydroxy sulfonate aldehydes, or mixtures of alpha-hydroxy sulfonate aldehydes and phthalaldehydes, and methods of using the compounds or compositions for disinfection or sterilization |
| US7390837B2 (en) | 2004-01-30 | 2008-06-24 | Ethicon, Inc. | Germicidal compositions containing phenylmalonaldehyde-type compounds, or mixtures of phenylmalonaldehyde-type compounds and phthalaldehydes, and methods of using such compositions for disinfection or sterilization |
| US7291649B2 (en) | 2005-06-29 | 2007-11-06 | Ethicon, Inc. | Forming germicidal aromatic dialdehydes with acetals |
| CZ301037B6 (cs) * | 2007-09-06 | 2009-10-21 | Vysoká škola chemicko-technologická v Praze | Amidové konjugáty steroidních a žlucových kyselin s D-glukosaminem a zpusob jejich prípravy |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| SI2384318T1 (en) | 2008-12-31 | 2018-03-30 | Ardelyx, Inc. | MEASURES AND PROCEDURES FOR THE INHIBITION OF ANTIPORT INHIBITED BY NHE IN THE TREATMENT OF DISEASES RELATED TO STRENGTH OF FLAMMABILITY OR TRADEMARITY WITH SOLO, AND THE EMISSION OF GASTROINTESTINAL TREATMENT |
| LT2983667T (lt) | 2013-04-12 | 2019-07-10 | Ardelyx, Inc. | Nhe3 rišantys junginiai ir fosfato pernešimo slopinimo būdai |
| EA201991676A1 (ru) | 2017-01-09 | 2020-01-30 | Арделикс, Инк. | Ингибиторы nhe-опосредованного антипорта |
| CA3049678A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
| US12186329B2 (en) | 2018-08-23 | 2025-01-07 | President And Fellows Of Harvard College | Compositions and methods related to cholic acid 7-sulfate as a treatment for diabetes |
| WO2020117945A1 (en) | 2018-12-04 | 2020-06-11 | President And Fellows Of Harvard College | Synthetic derivatives of cholic acid 7-sulfate and uses thereof |
| AU2020274319B2 (en) | 2019-05-10 | 2026-02-12 | President And Fellows Of Harvard College | Small molecule modulators of gut bacterial bile acid metabolism |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW289021B (https=) * | 1993-05-08 | 1996-10-21 | Hoechst Ag | |
| US5792635A (en) * | 1995-06-07 | 1998-08-11 | Magainin Pharmaceuticals, Inc. | Method of inhibiting the sodium/proton exchanger NHE3 and method of inhibiting growth by administering squalamine |
| JPH0959162A (ja) * | 1995-08-28 | 1997-03-04 | Makoto Takahashi | 胆石溶解剤 |
| DE19633966A1 (de) * | 1996-08-22 | 1998-02-26 | Hoechst Ag | Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1998
- 1998-10-28 DE DE19849722A patent/DE19849722A1/de not_active Withdrawn
-
1999
- 1999-10-15 ID IDW00200100935A patent/ID29025A/id unknown
- 1999-10-15 BR BR9914929-0A patent/BR9914929A/pt not_active IP Right Cessation
- 1999-10-15 AT AT99949001T patent/ATE236191T1/de not_active IP Right Cessation
- 1999-10-15 HK HK02102812.0A patent/HK1041271A1/zh unknown
- 1999-10-15 WO PCT/EP1999/007828 patent/WO2000024761A1/de not_active Ceased
- 1999-10-15 DE DE59904875T patent/DE59904875D1/de not_active Expired - Lifetime
- 1999-10-15 PT PT99949001T patent/PT1124841E/pt unknown
- 1999-10-15 TR TR2001/01163T patent/TR200101163T2/xx unknown
- 1999-10-15 KR KR1020017005343A patent/KR20010085973A/ko not_active Abandoned
- 1999-10-15 AU AU62032/99A patent/AU757365B2/en not_active Ceased
- 1999-10-15 DK DK99949001T patent/DK1124841T3/da active
- 1999-10-15 PL PL99348108A patent/PL348108A1/xx unknown
- 1999-10-15 RU RU2001114207/04A patent/RU2232769C2/ru not_active IP Right Cessation
- 1999-10-15 CN CN99812751A patent/CN1325403A/zh active Pending
- 1999-10-15 EP EP99949001A patent/EP1124841B1/de not_active Expired - Lifetime
- 1999-10-15 CA CA002349523A patent/CA2349523A1/en not_active Abandoned
- 1999-10-15 JP JP2000578331A patent/JP4616479B2/ja not_active Expired - Fee Related
- 1999-10-15 CZ CZ20011429A patent/CZ20011429A3/cs unknown
- 1999-10-15 HU HU0103751A patent/HUP0103751A3/hu unknown
- 1999-10-15 ES ES99949001T patent/ES2191466T3/es not_active Expired - Lifetime
- 1999-10-20 US US09/422,146 patent/US6166002A/en not_active Expired - Lifetime
-
2001
- 2001-04-17 ZA ZA200103106A patent/ZA200103106B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002528460A (ja) | 2002-09-03 |
| CA2349523A1 (en) | 2000-05-04 |
| KR20010085973A (ko) | 2001-09-07 |
| AU6203299A (en) | 2000-05-15 |
| HUP0103751A2 (hu) | 2002-04-29 |
| EP1124841A1 (de) | 2001-08-22 |
| DK1124841T3 (da) | 2003-07-28 |
| DE59904875D1 (de) | 2003-05-08 |
| CN1325403A (zh) | 2001-12-05 |
| PL348108A1 (en) | 2002-05-06 |
| JP4616479B2 (ja) | 2011-01-19 |
| ZA200103106B (en) | 2002-08-28 |
| DE19849722A1 (de) | 2000-05-04 |
| AU757365B2 (en) | 2003-02-20 |
| TR200101163T2 (tr) | 2001-08-21 |
| ID29025A (id) | 2001-07-26 |
| EP1124841B1 (de) | 2003-04-02 |
| WO2000024761A1 (de) | 2000-05-04 |
| PT1124841E (pt) | 2003-08-29 |
| HK1041271A1 (zh) | 2002-07-05 |
| US6166002A (en) | 2000-12-26 |
| BR9914929A (pt) | 2001-07-10 |
| ATE236191T1 (de) | 2003-04-15 |
| HUP0103751A3 (en) | 2002-12-28 |
| ES2191466T3 (es) | 2003-09-01 |
| RU2232769C2 (ru) | 2004-07-20 |
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