ES2485492T3 - Derivados de di(hetero)arilciclohexano, su preparación, su uso y composiciones farmacéuticas que los comprenden - Google Patents
Derivados de di(hetero)arilciclohexano, su preparación, su uso y composiciones farmacéuticas que los comprenden Download PDFInfo
- Publication number
- ES2485492T3 ES2485492T3 ES08758710.1T ES08758710T ES2485492T3 ES 2485492 T3 ES2485492 T3 ES 2485492T3 ES 08758710 T ES08758710 T ES 08758710T ES 2485492 T3 ES2485492 T3 ES 2485492T3
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- Prior art keywords
- esi
- alkyl
- optionally substituted
- fluorophenyl
- methyl
- Prior art date
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- 125000005842 heteroatom Chemical group 0.000 title abstract description 8
- 238000002360 preparation method Methods 0.000 title description 15
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 [1,2,4] triazolyl Chemical group 0.000 abstract description 226
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 25
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 18
- 125000001153 fluoro group Chemical group F* 0.000 abstract 8
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 5
- 150000002367 halogens Chemical class 0.000 abstract 5
- 125000004076 pyridyl group Chemical group 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 28
- 102100031787 Myosin regulatory light polypeptide 9 Human genes 0.000 description 20
- 101710107065 Myosin regulatory light polypeptide 9 Proteins 0.000 description 20
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
- 240000007313 Tilia cordata Species 0.000 description 19
- 102100031829 Myosin light polypeptide 6 Human genes 0.000 description 12
- 101710101143 Myosin light polypeptide 6 Proteins 0.000 description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 8
- 125000005415 substituted alkoxy group Chemical group 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 125000004462 3,4-difluorophenylmethyl group Chemical group FC=1C=C(C=CC1F)C* 0.000 description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 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
- GKXOABVSZWCJJK-UHFFFAOYSA-N 4-oxo-1-phenylcyclohexane-1-carbonitrile Chemical compound C1CC(=O)CCC1(C#N)C1=CC=CC=C1 GKXOABVSZWCJJK-UHFFFAOYSA-N 0.000 description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- ZQWPRMPSCMSAJU-UHFFFAOYSA-N methyl cyclohexanecarboxylate Chemical compound COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 2
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- CTOZSTUVBWSICB-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-(3-methylsulfanylphenyl)-1,2,4-triazole Chemical compound CSC1=CC=CC(C2=NN(CC3CC3)C=N2)=C1 CTOZSTUVBWSICB-UHFFFAOYSA-N 0.000 description 1
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- JPRNOVPCJUSIBE-UHFFFAOYSA-N 1-bromo-4-fluoro-2-methylsulfanylbenzene Chemical compound CSC1=CC(F)=CC=C1Br JPRNOVPCJUSIBE-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- QXXHHHWXFHPNOS-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxylic acid Chemical class C=1C=CC=CC=1C1(C(=O)O)CCCCC1 QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- TZNJHEHAYZJBHR-UHFFFAOYSA-N 2-bromo-1,1,1-trifluoroethane Chemical compound FC(F)(F)CBr TZNJHEHAYZJBHR-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- XIQGUOVQGKCPOX-UHFFFAOYSA-N 4-(3-bromophenyl)-4-hydroxy-1-phenylcyclohexane-1-carbonitrile Chemical compound C1CC(O)(C=2C=C(Br)C=CC=2)CCC1(C#N)C1=CC=CC=C1 XIQGUOVQGKCPOX-UHFFFAOYSA-N 0.000 description 1
- JYLDEJZLFBVYIX-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-hydroxy-1-phenylcyclohexane-1-carbonitrile Chemical compound C1CC(O)(C=2C=CC(F)=CC=2)CCC1(C#N)C1=CC=CC=C1 JYLDEJZLFBVYIX-UHFFFAOYSA-N 0.000 description 1
- MLOXMWAYJQPDIY-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-methoxy-1-phenylcyclohexane-1-carbonitrile Chemical compound C1CC(OC)(C=2C=CC(F)=CC=2)CCC1(C#N)C1=CC=CC=C1 MLOXMWAYJQPDIY-UHFFFAOYSA-N 0.000 description 1
- RTACWKNYPURKAD-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-methoxy-1-phenylcyclohexane-1-carboxylic acid Chemical compound C1CC(OC)(C=2C=CC(F)=CC=2)CCC1(C(O)=O)C1=CC=CC=C1 RTACWKNYPURKAD-UHFFFAOYSA-N 0.000 description 1
- JHHKWTRDVYDYEV-UHFFFAOYSA-N 4-[4-bromo-1-(cyclopropylmethyl)-5-methylimidazol-2-yl]-4-(cyclopropylmethoxy)-1-(4-fluorophenyl)cyclohexane-1-carboxylic acid Chemical compound CC1=C(Br)N=C(C2(CCC(CC2)(C(O)=O)C=2C=CC(F)=CC=2)OCC2CC2)N1CC1CC1 JHHKWTRDVYDYEV-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- QJHGJSHNFXKDQH-UHFFFAOYSA-N 4-chloro-5-methyl-1h-imidazole Chemical compound CC=1NC=NC=1Cl QJHGJSHNFXKDQH-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QARVLSVVCXYDNA-IDEBNGHGSA-N bromobenzene Chemical group Br[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 QARVLSVVCXYDNA-IDEBNGHGSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- 150000005378 cyclohexanecarboxylic acids Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07290698 | 2007-06-05 | ||
| EP07290698 | 2007-06-05 | ||
| PCT/EP2008/004112 WO2008148468A1 (en) | 2007-06-05 | 2008-05-23 | Di(hetero)arylcyclohexane derivatives, their preparation, their use and pharmaceutical compositions comprising them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2485492T3 true ES2485492T3 (es) | 2014-08-13 |
Family
ID=38704822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08758710.1T Active ES2485492T3 (es) | 2007-06-05 | 2008-05-23 | Derivados de di(hetero)arilciclohexano, su preparación, su uso y composiciones farmacéuticas que los comprenden |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8076324B2 (enExample) |
| EP (1) | EP2164825B1 (enExample) |
| JP (1) | JP5384485B2 (enExample) |
| KR (1) | KR101608702B1 (enExample) |
| CN (1) | CN101679191B (enExample) |
| AR (1) | AR066833A1 (enExample) |
| AU (1) | AU2008258871B2 (enExample) |
| BR (1) | BRPI0812590A2 (enExample) |
| CA (1) | CA2689985C (enExample) |
| CL (1) | CL2008001615A1 (enExample) |
| DK (1) | DK2164825T3 (enExample) |
| ES (1) | ES2485492T3 (enExample) |
| IL (1) | IL202470A (enExample) |
| MX (1) | MX2009012644A (enExample) |
| MY (1) | MY148903A (enExample) |
| PT (1) | PT2164825E (enExample) |
| TW (1) | TWI445526B (enExample) |
| UY (1) | UY31118A1 (enExample) |
| WO (1) | WO2008148468A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2014015265A (es) | 2012-06-14 | 2015-08-12 | Basf Se | Metodos plaguicidas que utilizan compuestos de 3-piridiltiazol sustituido y derivados para combatir plagas de animales. |
| MX2021006804A (es) | 2015-12-17 | 2023-01-13 | Merck Patent Gmbh | Antagonistas policiclicos del receptor 7/8 tipo toll (tlr7/8) y uso de los mismos en el tratamiento de trastornos inmunitarios. |
| RU2758686C2 (ru) * | 2016-08-08 | 2021-11-01 | Мерк Патент Гмбх | Антагонисты tlr7/8 и их применение |
| CN110483402B (zh) * | 2019-08-12 | 2021-07-23 | 上海毕得医药科技股份有限公司 | 一种3-溴-5-苯基-1h-吡唑的合成方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3927930A1 (de) * | 1989-08-24 | 1991-02-28 | Bayer Ag | Cyclisch substituierte (chinolin-2-yl-methoxy)phenyl-essig-saeure-derivate |
| WO1993019749A1 (en) | 1992-04-02 | 1993-10-14 | Smithkline Beecham Corporation | Compounds useful for treating allergic and inflammatory diseases |
| DK0612724T3 (da) * | 1993-02-23 | 1997-06-16 | Hoechst Ag | Substituerede benzensulfonylurinstoffer og -thiourinstoffer, fremgangsmåde til deres fremstilling og deres anvendelse som farmaceutika |
| DE4341655A1 (de) * | 1993-12-07 | 1995-06-08 | Hoechst Ag | Aminosubstituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika |
| DE19505397A1 (de) * | 1995-02-17 | 1996-08-22 | Hoechst Ag | Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| JP2000507558A (ja) * | 1996-03-25 | 2000-06-20 | スミスクライン・ビーチャム・コーポレイション | Cns損傷についての新規な治療 |
| JP2002500187A (ja) | 1998-01-07 | 2002-01-08 | スミスクライン・ビーチャム・コーポレイション | 多発性硬化症の治療方法 |
| UY25338A1 (es) * | 1998-01-07 | 2001-08-27 | Smithkline Beecham Corp | Método para tratar copd |
| DE19832009A1 (de) * | 1998-07-16 | 2000-01-20 | Hoechst Marion Roussel De Gmbh | 2,5-Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharamazeutische Präparate |
| DE69923464T2 (de) * | 1998-09-10 | 2006-05-11 | Sanofi-Aventis Deutschland Gmbh | Benzenesulfonamide derivate in kombination mit beta-blockern zur behandlung von störungen des autonomen nervensystems |
| US6887870B1 (en) * | 1999-10-12 | 2005-05-03 | Bristol-Myers Squibb Company | Heterocyclic sodium/proton exchange inhibitors and method |
| CA2401489A1 (en) * | 2000-03-02 | 2001-09-07 | Ichiro Miki | Oxygen-containing heterocyclic compounds |
| GB0012214D0 (en) | 2000-05-19 | 2000-07-12 | Merck Sharp & Dohme | Therapeutic agents |
| DE10135636A1 (de) * | 2001-07-17 | 2003-02-06 | Gruenenthal Gmbh | Substituierte 4-Aminocyclohexanole |
| TW200424183A (en) * | 2002-08-09 | 2004-11-16 | Nps Pharma Inc | New compounds |
| EP1679069A4 (en) | 2003-10-21 | 2009-05-13 | Dainippon Sumitomo Pharma Co | NEW PIPERIDINE DERIVATIVE |
| US20080096922A1 (en) * | 2004-04-06 | 2008-04-24 | Dainippon Sumitomo Pharma Co., Ltd. | Novel Sulfonamide derivative |
-
2008
- 2008-05-23 PT PT87587101T patent/PT2164825E/pt unknown
- 2008-05-23 CA CA2689985A patent/CA2689985C/en not_active Expired - Fee Related
- 2008-05-23 MY MYPI20094889A patent/MY148903A/en unknown
- 2008-05-23 MX MX2009012644A patent/MX2009012644A/es active IP Right Grant
- 2008-05-23 EP EP08758710.1A patent/EP2164825B1/en not_active Not-in-force
- 2008-05-23 KR KR1020097025449A patent/KR101608702B1/ko not_active Expired - Fee Related
- 2008-05-23 CN CN200880017289.0A patent/CN101679191B/zh not_active Expired - Fee Related
- 2008-05-23 WO PCT/EP2008/004112 patent/WO2008148468A1/en not_active Ceased
- 2008-05-23 ES ES08758710.1T patent/ES2485492T3/es active Active
- 2008-05-23 AU AU2008258871A patent/AU2008258871B2/en not_active Ceased
- 2008-05-23 DK DK08758710.1T patent/DK2164825T3/da active
- 2008-05-23 BR BRPI0812590-2A2A patent/BRPI0812590A2/pt not_active IP Right Cessation
- 2008-05-23 JP JP2010510664A patent/JP5384485B2/ja not_active Expired - Fee Related
- 2008-06-03 TW TW097120531A patent/TWI445526B/zh not_active IP Right Cessation
- 2008-06-03 CL CL200801615A patent/CL2008001615A1/es unknown
- 2008-06-03 AR ARP080102340A patent/AR066833A1/es unknown
- 2008-06-03 UY UY31118A patent/UY31118A1/es not_active Application Discontinuation
-
2009
- 2009-12-02 IL IL202470A patent/IL202470A/en not_active IP Right Cessation
- 2009-12-03 US US12/630,537 patent/US8076324B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR101608702B1 (ko) | 2016-04-04 |
| KR20100017659A (ko) | 2010-02-16 |
| IL202470A (en) | 2013-08-29 |
| US8076324B2 (en) | 2011-12-13 |
| UY31118A1 (es) | 2009-01-30 |
| JP2010529052A (ja) | 2010-08-26 |
| TWI445526B (zh) | 2014-07-21 |
| EP2164825B1 (en) | 2014-04-30 |
| MX2009012644A (es) | 2009-12-10 |
| JP5384485B2 (ja) | 2014-01-08 |
| TW200911228A (en) | 2009-03-16 |
| CA2689985C (en) | 2015-07-14 |
| AR066833A1 (es) | 2009-09-16 |
| AU2008258871A1 (en) | 2008-12-11 |
| AU2008258871B2 (en) | 2013-08-15 |
| MY148903A (en) | 2013-06-14 |
| IL202470A0 (en) | 2010-06-30 |
| DK2164825T3 (da) | 2014-07-14 |
| US20100204206A1 (en) | 2010-08-12 |
| CA2689985A1 (en) | 2008-12-11 |
| EP2164825A1 (en) | 2010-03-24 |
| WO2008148468A1 (en) | 2008-12-11 |
| CN101679191B (zh) | 2014-03-12 |
| BRPI0812590A2 (pt) | 2015-02-18 |
| PT2164825E (pt) | 2014-06-24 |
| CN101679191A (zh) | 2010-03-24 |
| CL2008001615A1 (es) | 2008-10-10 |
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