ES2371467T3 - Amidinas y derivados de las mismas y composiciones farmacéuticas que las contienen. - Google Patents
Amidinas y derivados de las mismas y composiciones farmacéuticas que las contienen. Download PDFInfo
- Publication number
- ES2371467T3 ES2371467T3 ES04787150T ES04787150T ES2371467T3 ES 2371467 T3 ES2371467 T3 ES 2371467T3 ES 04787150 T ES04787150 T ES 04787150T ES 04787150 T ES04787150 T ES 04787150T ES 2371467 T3 ES2371467 T3 ES 2371467T3
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- formula
- isobutylphenyl
- propionamidine
- amidines
- 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 - Lifetime
Links
- 150000001409 amidines Chemical class 0.000 title claims abstract description 20
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 108090001007 Interleukin-8 Proteins 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 7
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 7
- 230000010410 reperfusion Effects 0.000 claims abstract description 6
- 206010018364 Glomerulonephritis Diseases 0.000 claims abstract description 5
- 230000006378 damage Effects 0.000 claims abstract description 5
- 208000028867 ischemia Diseases 0.000 claims abstract description 5
- 201000001441 melanoma Diseases 0.000 claims abstract description 5
- 230000002265 prevention Effects 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims abstract description 4
- 206010016654 Fibrosis Diseases 0.000 claims abstract description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims abstract description 4
- 230000004761 fibrosis Effects 0.000 claims abstract description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
- -1 3-Benzoylphenyl Chemical group 0.000 claims description 32
- 102000004890 Interleukin-8 Human genes 0.000 claims description 29
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 claims description 28
- 229940096397 interleukin-8 Drugs 0.000 claims description 28
- SMEPCZFNZRVMCC-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propanimidamide;hydrochloride Chemical compound Cl.CC(C)CC1=CC=C(C(C)C(N)=N)C=C1 SMEPCZFNZRVMCC-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 16
- 230000035605 chemotaxis Effects 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 210000003622 mature neutrocyte Anatomy 0.000 claims description 9
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 229910003827 NRaRb Inorganic materials 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- DFWRZHZPJJAJMX-UHFFFAOYSA-N propanimidamide;hydrochloride Chemical compound Cl.CCC(N)=N DFWRZHZPJJAJMX-UHFFFAOYSA-N 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- KLOFSQZUEBHJTE-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]-2-[4-(2-methylpropyl)phenyl]propanimidamide Chemical compound CC(C)CC1=CC=C(C(C)C(=N)NCCCN(C)C)C=C1 KLOFSQZUEBHJTE-UHFFFAOYSA-N 0.000 claims description 5
- OAFSQIAHSDCZJL-UHFFFAOYSA-N 2-(3-benzoylphenyl)propanimidamide;hydrochloride Chemical compound Cl.NC(=N)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 OAFSQIAHSDCZJL-UHFFFAOYSA-N 0.000 claims description 4
- JOJNBBJEYLUPRP-UHFFFAOYSA-N 3-[1-[4-(2-methylpropyl)phenyl]ethyl]-5,6-dihydro-2h-1,2,4-oxadiazine Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C1=NCCON1 JOJNBBJEYLUPRP-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- FHQNFURCVCJTNY-UHFFFAOYSA-N n'-benzyl-2-[4-(2-methylpropyl)phenyl]propanimidamide Chemical compound C1=CC(CC(C)C)=CC=C1C(C)C(=N)NCC1=CC=CC=C1 FHQNFURCVCJTNY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- UQNCOOZDFCLMGG-UHFFFAOYSA-N propanimidamide;dihydrochloride Chemical compound Cl.Cl.CCC(N)=N UQNCOOZDFCLMGG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000006726 (C1-C5) alkenyl group Chemical group 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 206010034277 Pemphigoid Diseases 0.000 claims description 3
- OLAPNTTXGFTMDR-UHFFFAOYSA-N [4-(1-amino-1-iminopropan-2-yl)phenyl] trifluoromethanesulfonate;hydrochloride Chemical compound Cl.NC(=N)C(C)C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1 OLAPNTTXGFTMDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 208000000594 bullous pemphigoid Diseases 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 210000000224 granular leucocyte Anatomy 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 210000000440 neutrophil Anatomy 0.000 abstract description 11
- 230000030505 negative regulation of chemotaxis Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 24
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 102000002791 Interleukin-8B Receptors Human genes 0.000 description 11
- 108010018951 Interleukin-8B Receptors Proteins 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 230000004913 activation Effects 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 description 7
- 101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 description 7
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- 230000001225 therapeutic effect Effects 0.000 description 7
- PKQKHWNHCKNYSW-UHFFFAOYSA-N (+-)-2-(4'-isobutylphenyl)propionitrile Chemical compound CC(C)CC1=CC=C(C(C)C#N)C=C1 PKQKHWNHCKNYSW-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 6
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
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- 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
- C07C257/14—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 acyclic carbon 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/10—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biotechnology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03103557 | 2003-09-25 | ||
| EP03103557 | 2003-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2371467T3 true ES2371467T3 (es) | 2012-01-03 |
Family
ID=34354582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04787150T Expired - Lifetime ES2371467T3 (es) | 2003-09-25 | 2004-09-16 | Amidinas y derivados de las mismas y composiciones farmacéuticas que las contienen. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7674806B2 (enExample) |
| EP (1) | EP1663960B1 (enExample) |
| JP (1) | JP4795242B2 (enExample) |
| CN (1) | CN1882530A (enExample) |
| AT (1) | ATE521589T1 (enExample) |
| AU (1) | AU2004274183B8 (enExample) |
| CA (1) | CA2539842C (enExample) |
| ES (1) | ES2371467T3 (enExample) |
| NO (1) | NO336732B1 (enExample) |
| PT (1) | PT1663960E (enExample) |
| RU (1) | RU2375346C2 (enExample) |
| WO (1) | WO2005028425A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1934077B (zh) * | 2004-03-23 | 2010-09-29 | 冬姆佩制药股份公司 | 2-苯基丙酸衍生物及含有它们的药物组合物 |
| US7592362B2 (en) * | 2006-01-19 | 2009-09-22 | Pfizer Limited | Substituted imidazoles |
| EP2316820A1 (en) * | 2009-10-28 | 2011-05-04 | Dompe S.p.A. | 2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them |
| EP3156400B1 (en) | 2016-05-27 | 2019-05-15 | Valoralia I Más D, SL | Dihydrooxadiazine compounds for treating infections and cancer |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2919274A (en) * | 1957-09-17 | 1959-12-29 | Sahyun Melville | Amidines |
| FR2241300A1 (en) * | 1973-08-20 | 1975-03-21 | Wander Ag Dr A | Antidepressant N-carbamoyl-phenyl-acet- or propion-amidines - active by oral, rectal or parenteral administration |
| GB9514518D0 (en) * | 1995-07-15 | 1995-09-13 | Sod Conseils Rech Applic | Guanidine salt inhibitors of NO synthase and cyclooxygenase |
| IT1317826B1 (it) | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
| JP2001302643A (ja) * | 2000-04-21 | 2001-10-31 | Suntory Ltd | 環状アミジン化合物 |
| FR2810979B1 (fr) * | 2000-06-29 | 2002-08-23 | Adir | Nouveaux derives de diphenyluree, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
2004
- 2004-09-16 AT AT04787150T patent/ATE521589T1/de active
- 2004-09-16 ES ES04787150T patent/ES2371467T3/es not_active Expired - Lifetime
- 2004-09-16 PT PT04787150T patent/PT1663960E/pt unknown
- 2004-09-16 WO PCT/EP2004/052201 patent/WO2005028425A2/en not_active Ceased
- 2004-09-16 CN CNA2004800334914A patent/CN1882530A/zh active Pending
- 2004-09-16 RU RU2006113947/04A patent/RU2375346C2/ru not_active IP Right Cessation
- 2004-09-16 US US10/568,760 patent/US7674806B2/en not_active Expired - Fee Related
- 2004-09-16 AU AU2004274183A patent/AU2004274183B8/en not_active Ceased
- 2004-09-16 JP JP2006527406A patent/JP4795242B2/ja not_active Expired - Fee Related
- 2004-09-16 CA CA2539842A patent/CA2539842C/en not_active Expired - Fee Related
- 2004-09-16 EP EP04787150A patent/EP1663960B1/en not_active Expired - Lifetime
-
2006
- 2006-04-19 NO NO20061721A patent/NO336732B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP4795242B2 (ja) | 2011-10-19 |
| RU2006113947A (ru) | 2006-08-27 |
| EP1663960B1 (en) | 2011-08-24 |
| ATE521589T1 (de) | 2011-09-15 |
| WO2005028425A3 (en) | 2005-06-09 |
| NO20061721L (no) | 2006-04-19 |
| AU2004274183A1 (en) | 2005-03-31 |
| AU2004274183B8 (en) | 2011-04-28 |
| CN1882530A (zh) | 2006-12-20 |
| US7674806B2 (en) | 2010-03-09 |
| WO2005028425A2 (en) | 2005-03-31 |
| RU2375346C2 (ru) | 2009-12-10 |
| CA2539842A1 (en) | 2005-03-31 |
| CA2539842C (en) | 2013-02-12 |
| US20070155717A1 (en) | 2007-07-05 |
| AU2004274183B2 (en) | 2011-04-21 |
| EP1663960A2 (en) | 2006-06-07 |
| NO336732B1 (no) | 2015-10-26 |
| JP2007506706A (ja) | 2007-03-22 |
| PT1663960E (pt) | 2011-12-16 |
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