DE19633966A1 - Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament - Google Patents
Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes MedikamentInfo
- Publication number
- DE19633966A1 DE19633966A1 DE19633966A DE19633966A DE19633966A1 DE 19633966 A1 DE19633966 A1 DE 19633966A1 DE 19633966 A DE19633966 A DE 19633966A DE 19633966 A DE19633966 A DE 19633966A DE 19633966 A1 DE19633966 A1 DE 19633966A1
- Authority
- DE
- Germany
- Prior art keywords
- zero
- alkyl
- methyl
- compound
- substituted
- 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.)
- Withdrawn
Links
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- 239000002253 acid Substances 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title claims description 11
- 230000008569 process Effects 0.000 title claims description 4
- 150000002357 guanidines Chemical class 0.000 title description 2
- 239000000032 diagnostic agent Substances 0.000 title 1
- 229940039227 diagnostic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- XILYOLONIFWGMT-UHFFFAOYSA-N benzene;dihydrochloride Chemical compound Cl.Cl.C1=CC=CC=C1 XILYOLONIFWGMT-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- 210000000056 organ Anatomy 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical class [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- BVSRWCMAJISCTD-UHFFFAOYSA-N ethyl 2-diethoxyphosphorylpropanoate Chemical compound CCOC(=O)C(C)P(=O)(OCC)OCC BVSRWCMAJISCTD-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
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- 238000010561 standard procedure Methods 0.000 description 4
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- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
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- 230000002253 anti-ischaemic effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 150000001502 aryl halides Chemical class 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 239000002775 capsule Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
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- 230000001413 cellular effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
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- 235000012000 cholesterol Nutrition 0.000 description 1
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- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- SYZWSSNHPZXGML-UHFFFAOYSA-N dichloromethane;oxolane Chemical compound ClCCl.C1CCOC1 SYZWSSNHPZXGML-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008694 endothelial dysfunction Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- FHTHZBDITYYYQY-UHFFFAOYSA-N guanidine methanol Chemical compound CO.NC(=N)N.CO FHTHZBDITYYYQY-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005534 hematocrit Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000002727 hyperosmolar Effects 0.000 description 1
- 150000007928 imidazolide derivatives Chemical class 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000002530 ischemic preconditioning effect Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
- XARNMUQDYQFLNA-UHFFFAOYSA-N n-(diaminomethylidene)-3-methylsulfonyl-4-piperidin-1-ylbenzamide;hydrochloride Chemical compound Cl.CS(=O)(=O)C1=CC(C(=O)N=C(N)N)=CC=C1N1CCCCC1 XARNMUQDYQFLNA-UHFFFAOYSA-N 0.000 description 1
- ZIPLKLQPLOWLTM-UHFFFAOYSA-N naphthalene-2,3-dicarbaldehyde Chemical compound C1=CC=C2C=C(C=O)C(C=O)=CC2=C1 ZIPLKLQPLOWLTM-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000003286 potassium sparing diuretic agent Substances 0.000 description 1
- 229940097241 potassium-sparing diuretic Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 201000004240 prostatic hypertrophy Diseases 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 230000000054 salidiuretic effect Effects 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- 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
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Surgery (AREA)
- Reproductive Health (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19633966A DE19633966A1 (de) | 1996-08-22 | 1996-08-22 | Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| ES97114244T ES2158413T3 (es) | 1996-08-22 | 1997-08-18 | Alquenoilguanididas sustituidas con fenilo, procedimiento para su preparacion, su uso como farmacos o en agentes de diagnostico y medicamentos que las contienen. |
| EP97114244A EP0825178B1 (de) | 1996-08-22 | 1997-08-18 | Phenylsubstituierte Alkenylcarbonsäure-guanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE59703851T DE59703851D1 (de) | 1996-08-22 | 1997-08-18 | Phenylsubstituierte Alkenylcarbonsäure-guanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| SI9730153T SI0825178T1 (en) | 1996-08-22 | 1997-08-18 | Phenyl-substituted alkenoylguanidides, process for their preparation, their use as drugs or in diagnostic agents and drugs containing them |
| AT97114244T ATE202338T1 (de) | 1996-08-22 | 1997-08-18 | Phenylsubstituierte alkenylcarbonsäure-guanidide, verfahren zu ihrer herstellung, ihre verwendung als medikament oder diagnostikum sowie sie enthaltendes medikament |
| DK97114244T DK0825178T3 (da) | 1996-08-22 | 1997-08-18 | Phenylsubstituerede alkenylcarboxylsyreguanidider, fremgangsmåde til deres fremstilling, deres anvendelse som lægemiddel eller diagnostikum samt lægemiddel med indhold deraf |
| PT97114244T PT825178E (pt) | 1996-08-22 | 1997-08-18 | Guanidinas alquenilcarboxilicas substituidas no grupo fenilo processo para a sua preparacao sua utilizacao como medicamento ou diagnostico bem como medicamento que as contem |
| HU9701416A HUP9701416A3 (en) | 1996-08-22 | 1997-08-19 | Phenyl-substituted guanidides of alkenyl-carboxylic acids, process for producing them, and pharmaceutical compositions containing them |
| NZ328639A NZ328639A (en) | 1996-08-22 | 1997-08-20 | Phenyl-substituted alkenylcarboxylic acid guanidines; preparation and medicaments |
| CN97117484A CN1065861C (zh) | 1996-08-22 | 1997-08-20 | 苯基取代的链烯基羧酸胍、其制备方法、其作为药物或诊断剂的应用以及含有它的药 |
| US08/915,329 US6005010A (en) | 1996-08-22 | 1997-08-20 | Phenyl-substituted alkenylcarboxylic acid guanidides, process for their preparation, their use as a medicament or diagnostic, and medicament containing them |
| ARP970103787A AR008305A1 (es) | 1996-08-22 | 1997-08-20 | Guanidinas de acidos alquenil-carboxilicos sustituidos con fenilo, procedimientos para su preparacion, su utilizacion como medicamento o agente dediagnostico, asi como un medicamento que las contiene |
| TR97/00827A TR199700827A2 (xx) | 1996-08-22 | 1997-08-20 | Fenil'le s�bstit�e edilmi� alkenil karbonik asitguanidin'leri. |
| SK1138-97A SK282632B6 (sk) | 1996-08-22 | 1997-08-20 | Guanididy fenylsubstituovanej alkenylkarboxylovej kyseliny, spôsob ich prípravy, ich použitie ako liečiva alebo diagnostického činidla a liečivo, ktoré ich obsahuje |
| CZ972659A CZ265997A3 (cs) | 1996-08-22 | 1997-08-20 | Guanididy fenylsubstituované alkenylkarboxylové kyseliny, způsob jejich přípravy, jejich použití jako léčiva nebo diagnostického činidla a léčivo, které je obsahuje |
| NO973850A NO309468B1 (no) | 1996-08-22 | 1997-08-21 | Fenylsubstituerte alkenylkarboksylsyreguanidider, en fremgangsmåte for deres fremstilling, deres anvendelse såvel som legemidler inneholdende dem |
| IL12159097A IL121590A (en) | 1996-08-22 | 1997-08-21 | Phenyl-substituted alkenylcarboxylic acid guanidines, process for their preparation, and pharmaceutical compositions containing them |
| IDP972923A ID18066A (id) | 1996-08-22 | 1997-08-21 | Fenil yang tersubstitusi guanidida guanidida asam alkenilkarboksilat proses pembuatannya dan penggunaannya sebagai obat atau diagnosa |
| ZA9707494A ZA977494B (en) | 1996-08-22 | 1997-08-21 | Phenyl-substituted alkenylcarboxylic acid guanidines, process for their preparation, their use as a medicament or diagnostic, and medicament containing them. |
| MX9706380A MX9706380A (es) | 1996-08-22 | 1997-08-21 | Guanidinas de acidos alquenil-carboxilicos sustituidos con fenilo, procedimientos para su preparacion, su utilizacion como medicamento o agente de diagnostico, asi como un medicamento que las contiene. |
| AU35192/97A AU713664B2 (en) | 1996-08-22 | 1997-08-21 | Phenyl-substituted alkenylcarboxylic acid guanidides, process for their preparation, their use as a medicament or diagnostic, and medicament containing them |
| RU97114306/04A RU2193026C2 (ru) | 1996-08-22 | 1997-08-21 | Фенилзамещенные гуанидиды алкенилкарбоновой кислоты и лекарственное средство на их основе |
| JP22461397A JP4081159B2 (ja) | 1996-08-22 | 1997-08-21 | フェニル−置換されたアルケニルカルボン酸グアニジド、それらの製法、医薬または診断剤としてのそれらの使用およびそれらを含有する医薬 |
| HR970450A HRP970450B1 (en) | 1996-08-22 | 1997-08-21 | Phenyl-substituted alkenoylguanidides, process for their preparation, their use as drugs or diagnostic agents and drugs containing them |
| CA002213714A CA2213714C (en) | 1996-08-22 | 1997-08-22 | Phenyl-substituted alkenylcarboxylic acid guanidides, process for their preparation, their use as a medicament or diagnostic, and medicament containing them |
| BR9704483A BR9704483A (pt) | 1996-08-22 | 1997-08-22 | Guanididas de ácido alquenilcarboxílico fenil-substituídas processo para sua preparação sua utilização como medicamento ou meio de diagnóstico e medicamento que as contêm |
| KR1019970040115A KR19980018898A (ko) | 1996-08-22 | 1997-08-22 | 페닐 치환된 알케닐카복실산 구아니디드, 이의 제조방법, 약제 또는 진단제로서의 이의 용도 및 이를 함유하는 약제(Phenyl-substituted alkenylcarboxylic acid guanidides, process for their preparation, their use as a medicament or diagnostic, and medicament containing them) |
| PL97321748A PL321748A1 (en) | 1996-08-22 | 1997-08-22 | Novel substituted derivatives of benzene, method of obtaining them, their application in production of pharmaceutic agents and pharmaceutic agent as such |
| GR20010400976T GR3036123T3 (en) | 1996-08-22 | 2001-06-27 | Phenyl-substituted alkenoylguanidides, process for their preparation, their use as drugs or in diagnostic agents and drugs containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19633966A DE19633966A1 (de) | 1996-08-22 | 1996-08-22 | Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19633966A1 true DE19633966A1 (de) | 1998-02-26 |
Family
ID=7803413
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19633966A Withdrawn DE19633966A1 (de) | 1996-08-22 | 1996-08-22 | Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE59703851T Expired - Lifetime DE59703851D1 (de) | 1996-08-22 | 1997-08-18 | Phenylsubstituierte Alkenylcarbonsäure-guanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59703851T Expired - Lifetime DE59703851D1 (de) | 1996-08-22 | 1997-08-18 | Phenylsubstituierte Alkenylcarbonsäure-guanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6005010A (https=) |
| EP (1) | EP0825178B1 (https=) |
| JP (1) | JP4081159B2 (https=) |
| KR (1) | KR19980018898A (https=) |
| CN (1) | CN1065861C (https=) |
| AR (1) | AR008305A1 (https=) |
| AT (1) | ATE202338T1 (https=) |
| AU (1) | AU713664B2 (https=) |
| BR (1) | BR9704483A (https=) |
| CA (1) | CA2213714C (https=) |
| CZ (1) | CZ265997A3 (https=) |
| DE (2) | DE19633966A1 (https=) |
| DK (1) | DK0825178T3 (https=) |
| ES (1) | ES2158413T3 (https=) |
| GR (1) | GR3036123T3 (https=) |
| HR (1) | HRP970450B1 (https=) |
| HU (1) | HUP9701416A3 (https=) |
| ID (1) | ID18066A (https=) |
| IL (1) | IL121590A (https=) |
| MX (1) | MX9706380A (https=) |
| NO (1) | NO309468B1 (https=) |
| NZ (1) | NZ328639A (https=) |
| PL (1) | PL321748A1 (https=) |
| PT (1) | PT825178E (https=) |
| RU (1) | RU2193026C2 (https=) |
| SI (1) | SI0825178T1 (https=) |
| SK (1) | SK282632B6 (https=) |
| TR (1) | TR199700827A2 (https=) |
| ZA (1) | ZA977494B (https=) |
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| RU2193026C2 (ru) * | 1996-08-22 | 2002-11-20 | Хехст АГ | Фенилзамещенные гуанидиды алкенилкарбоновой кислоты и лекарственное средство на их основе |
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| DE19849722A1 (de) * | 1998-10-28 | 2000-05-04 | Aventis Pharma Gmbh | Substituierte Phenyl-alkenoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| WO2000067756A1 (en) * | 1999-05-07 | 2000-11-16 | The Trustees Of The Universtiy Of Pennsylvania | Methods for controlling intraocular pressure |
| DE19960204A1 (de) * | 1999-12-14 | 2001-06-28 | Aventis Pharma Gmbh | Substituierte Norlbornylamino-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE10015248A1 (de) * | 2000-03-28 | 2001-10-04 | Merck Patent Gmbh | Bisamidino-Verbindungen als NHE-3 Inhibitoren |
| DE10046993A1 (de) * | 2000-09-22 | 2002-04-11 | Aventis Pharma Gmbh | Substituierte Zimtsäureguanidide, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltendes Medikament |
| DE10063294A1 (de) | 2000-12-19 | 2002-07-04 | Aventis Pharma Gmbh | Substituierte Heterocyclo-Norbornylamino-Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE10161767A1 (de) * | 2001-12-15 | 2003-06-26 | Merck Patent Gmbh | 2-Guanidino-4-heterocyclyl-chinazoline |
| DE10163239A1 (de) * | 2001-12-21 | 2003-07-10 | Aventis Pharma Gmbh | Substituierte Imidazolidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie enthaltendes Medikament |
| US20030187045A1 (en) * | 2001-12-21 | 2003-10-02 | Uwe Heinelt | Substituted imidazolidines, process for their preparation, and their use as a medicament or diagnostic |
| US7049333B2 (en) | 2002-06-04 | 2006-05-23 | Sanofi-Aventis Deutschland Gmbh | Substituted thiophenes: compositions, processes of making, and uses in disease treatment and diagnosis |
| US20050054705A1 (en) * | 2003-02-04 | 2005-03-10 | Aventis Pharma Deutschland Gmbh | N-substituted (benzoimidazol-2-yl) phenylamines, process for their preparation, their use as medicament or diagnostic aid, and medicament comprising them |
| DE10304374A1 (de) * | 2003-02-04 | 2004-08-05 | Aventis Pharma Deutschland Gmbh | Neue substituierte 2-Aminoimidazole, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE10341240A1 (de) | 2003-09-08 | 2005-04-07 | Aventis Pharma Deutschland Gmbh | Substituierte Thienoimidazole, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE102005001411A1 (de) | 2005-01-12 | 2006-07-27 | Sanofi-Aventis Deutschland Gmbh | Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament |
| ATE479679T1 (de) * | 2007-06-28 | 2010-09-15 | Sanofi Aventis Us Llc | Verfahren zur herstellung von n-(2-chlor-4-methyl-3-thienyl)-1h-benzimidazol- 2-amin hydrochlorid und zwischenprodukte dafür |
| KR101169862B1 (ko) * | 2007-10-26 | 2012-07-31 | 제이에스알 가부시끼가이샤 | 액정 배향제, 액정 배향막의 형성 방법 및 액정 표시 소자 |
| BRPI0918502A2 (pt) | 2008-09-02 | 2015-12-01 | Sanofi Aventis | aminoindanos substituídos e análogos dos mesmos, e o uso farmacêutico dos mesmos |
| 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 |
| 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 |
| US20120088737A2 (en) * | 2009-10-02 | 2012-04-12 | Ajinomoto Co., Inc | Novel acyl guanidine derivatives |
| MX366293B (es) | 2012-08-21 | 2019-07-04 | Ardelyx Inc | Compuestos y metodos para inhibir al antipuerto mediado por nhe en el tratamiento de trastornos asociados con la retencion de fluidos o la sobrecarga de sal y trastornos del tracto gastrointestinal. |
| US10376481B2 (en) | 2012-08-21 | 2019-08-13 | 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 |
| 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 |
| CN118440135A (zh) | 2017-08-04 | 2024-08-06 | 阿德利克斯股份有限公司 | 用于治疗高钾血症的甘草次酸衍生物 |
| KR20260004570A (ko) | 2019-02-07 | 2026-01-08 | 알데릭스, 인코포레이티드 | 고칼륨혈증 치료에 사용하기 위한 글리시레틴산 유도체 |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4544670A (en) * | 1982-08-24 | 1985-10-01 | William H. Rorer, Inc. | Method of treating coccidiosis with acyl guanidines |
| DE4328352A1 (de) * | 1993-08-24 | 1995-03-02 | Hoechst Ag | Substituierte N,N'-Di-benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4421536A1 (de) * | 1994-06-20 | 1995-12-21 | Hoechst Ag | Perfluoralkylgruppen tragende phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| 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 |
-
1996
- 1996-08-22 DE DE19633966A patent/DE19633966A1/de not_active Withdrawn
-
1997
- 1997-08-18 DE DE59703851T patent/DE59703851D1/de not_active Expired - Lifetime
- 1997-08-18 SI SI9730153T patent/SI0825178T1/xx unknown
- 1997-08-18 PT PT97114244T patent/PT825178E/pt unknown
- 1997-08-18 AT AT97114244T patent/ATE202338T1/de not_active IP Right Cessation
- 1997-08-18 DK DK97114244T patent/DK0825178T3/da active
- 1997-08-18 ES ES97114244T patent/ES2158413T3/es not_active Expired - Lifetime
- 1997-08-18 EP EP97114244A patent/EP0825178B1/de not_active Expired - Lifetime
- 1997-08-19 HU HU9701416A patent/HUP9701416A3/hu unknown
- 1997-08-20 CN CN97117484A patent/CN1065861C/zh not_active Expired - Fee Related
- 1997-08-20 NZ NZ328639A patent/NZ328639A/xx unknown
- 1997-08-20 TR TR97/00827A patent/TR199700827A2/xx unknown
- 1997-08-20 AR ARP970103787A patent/AR008305A1/es unknown
- 1997-08-20 SK SK1138-97A patent/SK282632B6/sk unknown
- 1997-08-20 US US08/915,329 patent/US6005010A/en not_active Expired - Lifetime
- 1997-08-20 CZ CZ972659A patent/CZ265997A3/cs unknown
- 1997-08-21 ZA ZA9707494A patent/ZA977494B/xx unknown
- 1997-08-21 HR HR970450A patent/HRP970450B1/xx not_active IP Right Cessation
- 1997-08-21 NO NO973850A patent/NO309468B1/no not_active IP Right Cessation
- 1997-08-21 ID IDP972923A patent/ID18066A/id unknown
- 1997-08-21 RU RU97114306/04A patent/RU2193026C2/ru not_active IP Right Cessation
- 1997-08-21 AU AU35192/97A patent/AU713664B2/en not_active Ceased
- 1997-08-21 JP JP22461397A patent/JP4081159B2/ja not_active Expired - Fee Related
- 1997-08-21 IL IL12159097A patent/IL121590A/en not_active IP Right Cessation
- 1997-08-21 MX MX9706380A patent/MX9706380A/es not_active IP Right Cessation
- 1997-08-22 KR KR1019970040115A patent/KR19980018898A/ko not_active Ceased
- 1997-08-22 BR BR9704483A patent/BR9704483A/pt active Search and Examination
- 1997-08-22 CA CA002213714A patent/CA2213714C/en not_active Expired - Fee Related
- 1997-08-22 PL PL97321748A patent/PL321748A1/xx unknown
-
2001
- 2001-06-27 GR GR20010400976T patent/GR3036123T3/el not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2193026C2 (ru) * | 1996-08-22 | 2002-11-20 | Хехст АГ | Фенилзамещенные гуанидиды алкенилкарбоновой кислоты и лекарственное средство на их основе |
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