SA05260362B1 - مشتقات حمض فينوكسي أسيتيك مفيدة في علاج الامراض النفسية - Google Patents

Info

Publication number

SA05260362B1

SA05260362B1 SA05260362A SA05260362A SA05260362B1 SA 05260362 B1 SA05260362 B1 SA 05260362B1 SA 05260362 A SA05260362 A SA 05260362A SA 05260362 A SA05260362 A SA 05260362A SA 05260362 B1 SA05260362 B1 SA 05260362B1

Authority

SA

Saudi Arabia

Prior art keywords

methyl

chloro

phenoxy

acetic acid

piperazinyl

Prior art date

2004-11-23

Links

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• Global Dossier
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• LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title claims abstract description 18
• 241000045500 Diseae Species 0.000 title 1
• 230000000241 respiratory effect Effects 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 322
• 238000002360 preparation method Methods 0.000 claims abstract description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 436
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 281
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 155
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 106
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 98
• -1 alkyl halogen Chemical class 0.000 claims description 79
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 125000004193 piperazinyl group Chemical group 0.000 claims description 50
• 229910052736 halogen Inorganic materials 0.000 claims description 49
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
• 239000002253 acid Substances 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 25
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 22
• 238000006467 substitution reaction Methods 0.000 claims description 19
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 235000019260 propionic acid Nutrition 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 14
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 13
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 9
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 9
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 108090000623 proteins and genes Proteins 0.000 claims description 5
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 claims description 3
• ORSWDXYDKIPVGD-UHFFFAOYSA-N 2-[2-[(4-benzoyl-3-methylpiperazin-1-yl)methyl]-4-chlorophenoxy]acetic acid Chemical compound C1CN(C(=O)C=2C=CC=CC=2)C(C)CN1CC1=CC(Cl)=CC=C1OCC(O)=O ORSWDXYDKIPVGD-UHFFFAOYSA-N 0.000 claims description 3
• YFYBEPKDKMHPHF-UHFFFAOYSA-N 2-[2-[1-[4-(benzenesulfonyl)piperazin-1-yl]ethyl]-4-chlorophenoxy]acetic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C(Cl)=CC=C(OCC(O)=O)C=1C(C)N(CC1)CCN1S(=O)(=O)C1=CC=CC=C1 YFYBEPKDKMHPHF-UHFFFAOYSA-N 0.000 claims description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• SXJOQQNGWCJIHX-UHFFFAOYSA-N 2-[2-(4-benzylsulfonylpiperazin-1-yl)-4-chlorophenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1N1CCN(S(=O)(=O)CC=2C=CC=CC=2)CC1 SXJOQQNGWCJIHX-UHFFFAOYSA-N 0.000 claims description 2
• HMIPQKCYIJRCFK-UHFFFAOYSA-N 2-[2-[1-(4-benzoylpiperazin-1-yl)ethyl]-4-chlorophenoxy]acetic acid Chemical compound C=1C(Cl)=CC=C(OCC(O)=O)C=1C(C)N(CC1)CCN1C(=O)C1=CC=CC=C1 HMIPQKCYIJRCFK-UHFFFAOYSA-N 0.000 claims description 2
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 150000001412 amines Chemical class 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims description 2
• CWVWNDSQBGNNDK-UHFFFAOYSA-N 2-[4-chloro-2-[[4-[3-(difluoromethoxy)phenyl]sulfonylpiperazin-1-yl]methyl]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C=C1CN1CCN(S(=O)(=O)C=2C=C(OC(F)F)C=CC=2)CC1 CWVWNDSQBGNNDK-UHFFFAOYSA-N 0.000 claims 1
• 102100033668 Cartilage matrix protein Human genes 0.000 claims 1
• 101001018382 Homo sapiens Cartilage matrix protein Proteins 0.000 claims 1
• 150000007513 acids Chemical class 0.000 claims 1
• 239000013521 mastic Substances 0.000 claims 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 133
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
• 208000023504 respiratory system disease Diseases 0.000 abstract description 4
• 230000008569 process Effects 0.000 abstract description 3
• 239000000047 product Substances 0.000 description 201
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 180
• 238000001819 mass spectrum Methods 0.000 description 160
• 229960000583 acetic acid Drugs 0.000 description 159
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
• 235000011054 acetic acid Nutrition 0.000 description 75
• 239000000460 chlorine Substances 0.000 description 69
• 239000011541 reaction mixture Substances 0.000 description 66
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 65
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 63
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
• 239000000203 mixture Substances 0.000 description 55
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
• 239000000243 solution Substances 0.000 description 50
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 46
• 235000019439 ethyl acetate Nutrition 0.000 description 46
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 40
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 201000010099 disease Diseases 0.000 description 33
• 239000012298 atmosphere Substances 0.000 description 30
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 30
• 239000012267 brine Substances 0.000 description 29
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• 239000000377 silicon dioxide Substances 0.000 description 27
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 26
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 26
• 229940093499 ethyl acetate Drugs 0.000 description 25
• 239000003112 inhibitor Substances 0.000 description 25
• 239000007787 solid Substances 0.000 description 25
• CJJURHKDGQSBLE-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C(Cl)=C1 CJJURHKDGQSBLE-UHFFFAOYSA-N 0.000 description 24
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
• 238000004587 chromatography analysis Methods 0.000 description 23
• 239000003480 eluent Substances 0.000 description 23
• ILWHHIJCWNFDJY-UHFFFAOYSA-N 2-[2-fluoro-4-(trifluoromethyl)phenyl]acetyl chloride Chemical compound FC1=CC(C(F)(F)F)=CC=C1CC(Cl)=O ILWHHIJCWNFDJY-UHFFFAOYSA-N 0.000 description 22
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• 238000003756 stirring Methods 0.000 description 21
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
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• 239000011734 sodium Substances 0.000 description 11
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• 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
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