ZA200007039B - Biphenyl derivatives. - Google Patents
Biphenyl derivatives. Download PDFInfo
- Publication number
- ZA200007039B ZA200007039B ZA200007039A ZA200007039A ZA200007039B ZA 200007039 B ZA200007039 B ZA 200007039B ZA 200007039 A ZA200007039 A ZA 200007039A ZA 200007039 A ZA200007039 A ZA 200007039A ZA 200007039 B ZA200007039 B ZA 200007039B
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- ZA
- South Africa
- Prior art keywords
- formula
- compounds
- physiologically acceptable
- acceptable salts
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 5
- -1 4-amidinophenoxymethyl Chemical group 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 108010074860 Factor Xa Proteins 0.000 claims description 9
- 208000007536 Thrombosis Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 206010002383 Angina Pectoris Diseases 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 6
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 206010022562 Intermittent claudication Diseases 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002399 angioplasty Methods 0.000 claims description 6
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 6
- 208000010125 myocardial infarction Diseases 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 208000037803 restenosis Diseases 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000004866 oxadiazoles Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- QAIJMAFUGWSUFR-UHFFFAOYSA-N 3-[(3-carbamimidoylphenoxy)methyl]-5-(3-carbamimidoylphenyl)benzoic acid Chemical compound NC(=N)C1=CC=CC(OCC=2C=C(C=C(C=2)C(O)=O)C=2C=C(C=CC=2)C(N)=N)=C1 QAIJMAFUGWSUFR-UHFFFAOYSA-N 0.000 claims 1
- XVWGCWQAXSLVAX-UHFFFAOYSA-N 3-[3-[(3-carbamimidoylphenoxy)methyl]phenyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(OCC=2C=C(C=CC=2)C=2C=C(C=CC=2)C(N)=N)=C1 XVWGCWQAXSLVAX-UHFFFAOYSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 230000009424 thromboembolic effect Effects 0.000 description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108090000190 Thrombin Proteins 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 230000002785 anti-thrombosis Effects 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 229960004072 thrombin Drugs 0.000 description 3
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- 230000002429 anti-coagulating effect Effects 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000023555 blood coagulation Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108010094028 Prothrombin Proteins 0.000 description 1
- 102100027378 Prothrombin Human genes 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 229940039716 prothrombin Drugs 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/10—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19819548A DE19819548A1 (de) | 1998-04-30 | 1998-04-30 | Biphenylderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200007039B true ZA200007039B (en) | 2002-02-28 |
Family
ID=7866421
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200007039A ZA200007039B (en) | 1998-04-30 | 2000-11-29 | Biphenyl derivatives. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6380430B1 (de) |
| EP (1) | EP1076643A1 (de) |
| JP (1) | JP2002513780A (de) |
| KR (1) | KR20010052249A (de) |
| CN (1) | CN1299343A (de) |
| AR (1) | AR019264A1 (de) |
| AU (1) | AU750472B2 (de) |
| BR (1) | BR9910021A (de) |
| CA (1) | CA2328732A1 (de) |
| DE (1) | DE19819548A1 (de) |
| HU (1) | HUP0102220A3 (de) |
| ID (1) | ID27152A (de) |
| NO (1) | NO20005435D0 (de) |
| PL (1) | PL343598A1 (de) |
| RU (1) | RU2219166C2 (de) |
| SK (1) | SK15962000A3 (de) |
| UA (1) | UA58593C2 (de) |
| WO (1) | WO1999057096A1 (de) |
| ZA (1) | ZA200007039B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010101772A (ko) * | 1999-01-28 | 2001-11-14 | 야스이 쇼사꾸 | 방출제어제제 |
| DE19945302A1 (de) * | 1999-09-22 | 2001-03-29 | Merck Patent Gmbh | Biphenylderivate als NHE-3-Inhibitoren |
| DE10027024A1 (de) * | 2000-05-31 | 2001-12-06 | Merck Patent Gmbh | Carbaminsäureester |
| JP2004501913A (ja) * | 2000-06-23 | 2004-01-22 | ブリストル−マイヤーズ スクイブ ファーマ カンパニー | ヘテロアリール−フェニル置換Ｘａ因子阻害剤 |
| DE10037146A1 (de) * | 2000-07-29 | 2002-02-07 | Merck Patent Gmbh | Acetamidderivate |
| CN100513398C (zh) | 2002-12-03 | 2009-07-15 | Axys药物公司 | 作为因子viia抑制剂的2-(2-羟基联苯-3-基)-1h-苯并咪唑-5-甲脒衍生物 |
| US7534894B2 (en) | 2003-09-25 | 2009-05-19 | Wyeth | Biphenyloxy-acids |
| CN103012200B (zh) * | 2011-09-20 | 2014-12-17 | 北京大学 | 具有β-分泌酶抑制功能的化合物及其制备方法与应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5922697B2 (ja) | 1976-01-13 | 1984-05-28 | エーザイ株式会社 | ビス−（メタ−アミジノフエノキシ）−化合物 |
| US4086244A (en) * | 1976-12-10 | 1978-04-25 | E. R. Squibb & Sons, Inc. | Amidines |
| DE4102024A1 (de) * | 1991-01-24 | 1992-07-30 | Thomae Gmbh Dr K | Biphenylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4219158A1 (de) * | 1992-06-11 | 1993-12-16 | Thomae Gmbh Dr K | Biphenylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| PL316438A1 (en) * | 1995-11-20 | 1997-05-26 | Hoechst Ag | Novel substituted derivatives of benzoyloguanidine, method of obtaining them, their application in production of pharmaceutic and diagnostic agents and pharmaceutic agent as such |
| GB9600063D0 (en) * | 1996-01-03 | 1996-03-06 | Fujisawa Pharmaceutical Co | Guaridine derivatives |
-
1998
- 1998-04-30 DE DE19819548A patent/DE19819548A1/de not_active Withdrawn
-
1999
- 1999-04-12 ID IDW20002341A patent/ID27152A/id unknown
- 1999-04-12 AU AU38154/99A patent/AU750472B2/en not_active Ceased
- 1999-04-12 HU HU0102220A patent/HUP0102220A3/hu unknown
- 1999-04-12 WO PCT/EP1999/002457 patent/WO1999057096A1/de not_active Application Discontinuation
- 1999-04-12 CN CN99805661A patent/CN1299343A/zh active Pending
- 1999-04-12 RU RU2000129159/04A patent/RU2219166C2/ru not_active IP Right Cessation
- 1999-04-12 BR BR9910021-5A patent/BR9910021A/pt not_active IP Right Cessation
- 1999-04-12 CA CA002328732A patent/CA2328732A1/en not_active Abandoned
- 1999-04-12 PL PL99343598A patent/PL343598A1/xx unknown
- 1999-04-12 US US09/674,267 patent/US6380430B1/en not_active Expired - Fee Related
- 1999-04-12 JP JP2000547066A patent/JP2002513780A/ja active Pending
- 1999-04-12 KR KR1020007011315A patent/KR20010052249A/ko not_active Application Discontinuation
- 1999-04-12 EP EP99920646A patent/EP1076643A1/de not_active Withdrawn
- 1999-04-12 SK SK1596-2000A patent/SK15962000A3/sk unknown
- 1999-04-30 AR ARP990102014A patent/AR019264A1/es not_active Application Discontinuation
- 1999-12-04 UA UA2000116686A patent/UA58593C2/uk unknown
-
2000
- 2000-10-27 NO NO20005435A patent/NO20005435D0/no not_active Application Discontinuation
- 2000-11-29 ZA ZA200007039A patent/ZA200007039B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL343598A1 (en) | 2001-08-27 |
| ID27152A (id) | 2001-03-08 |
| EP1076643A1 (de) | 2001-02-21 |
| WO1999057096A1 (de) | 1999-11-11 |
| AR019264A1 (es) | 2002-02-13 |
| DE19819548A1 (de) | 1999-11-04 |
| US6380430B1 (en) | 2002-04-30 |
| HUP0102220A2 (hu) | 2001-10-28 |
| AU3815499A (en) | 1999-11-23 |
| NO20005435L (no) | 2000-10-27 |
| JP2002513780A (ja) | 2002-05-14 |
| CA2328732A1 (en) | 1999-11-11 |
| NO20005435D0 (no) | 2000-10-27 |
| AU750472B2 (en) | 2002-07-18 |
| KR20010052249A (ko) | 2001-06-25 |
| HUP0102220A3 (en) | 2002-11-28 |
| UA58593C2 (uk) | 2003-08-15 |
| CN1299343A (zh) | 2001-06-13 |
| BR9910021A (pt) | 2000-12-26 |
| SK15962000A3 (sk) | 2001-05-10 |
| RU2219166C2 (ru) | 2003-12-20 |
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