BE1010031A5 - Derives gem-difluoro de phenylacetamide et d'acide phenylacetique, leur preparation et leurs utilisations. - Google Patents
Derives gem-difluoro de phenylacetamide et d'acide phenylacetique, leur preparation et leurs utilisations. Download PDFInfo
- Publication number
- BE1010031A5 BE1010031A5 BE9600228A BE9600228A BE1010031A5 BE 1010031 A5 BE1010031 A5 BE 1010031A5 BE 9600228 A BE9600228 A BE 9600228A BE 9600228 A BE9600228 A BE 9600228A BE 1010031 A5 BE1010031 A5 BE 1010031A5
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- group
- substituted
- difluoro
- lower alkyl
- Prior art date
Links
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title abstract description 3
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical compound CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
- 125000002252 acyl group Chemical group 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 239000011734 sodium Substances 0.000 claims abstract description 10
- -1 methylenedioxy Chemical group 0.000 claims abstract description 8
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 7
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 239000011591 potassium Substances 0.000 claims abstract description 7
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 7
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000011575 calcium Substances 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 6
- 239000011777 magnesium Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 6
- 239000011701 zinc Substances 0.000 claims abstract description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000011593 sulfur Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 20
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 150000001412 amines Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 229960003424 phenylacetic acid Drugs 0.000 claims description 5
- 239000003279 phenylacetic acid Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000012434 nucleophilic reagent Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 229950005499 carbon tetrachloride Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 6
- 239000003435 antirheumatic agent Substances 0.000 abstract description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 229940049953 phenylacetate Drugs 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 7
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 5
- 229940113118 carrageenan Drugs 0.000 description 5
- 235000010418 carrageenan Nutrition 0.000 description 5
- 229920001525 carrageenan Polymers 0.000 description 5
- 239000000679 carrageenan Substances 0.000 description 5
- 210000000265 leukocyte Anatomy 0.000 description 5
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 5
- QASPDCZPPDUIIE-UHFFFAOYSA-N 2,2-difluoro-2-phenylacetamide Chemical class NC(=O)C(F)(F)C1=CC=CC=C1 QASPDCZPPDUIIE-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003682 fluorination reaction Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000001754 anti-pyretic effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229950009183 ibufenac Drugs 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- HUJVSQAQYBVMQC-UHFFFAOYSA-N 2-(1,3-benzodioxol-4-yl)acetamide Chemical compound NC(=O)CC1=CC=CC2=C1OCO2 HUJVSQAQYBVMQC-UHFFFAOYSA-N 0.000 description 2
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229960003699 evans blue Drugs 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 208000008423 pleurisy Diseases 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 210000000115 thoracic cavity Anatomy 0.000 description 2
- WKGFUAPIIGENOL-UHFFFAOYSA-N 1-acetyl-3,3-difluoroindol-2-one Chemical compound C1=CC=C2N(C(=O)C)C(=O)C(F)(F)C2=C1 WKGFUAPIIGENOL-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- NSYXNHYVSQQPSD-UHFFFAOYSA-N 2-(2-aminophenyl)-2,2-difluoroacetic acid Chemical compound NC1=CC=CC=C1C(F)(F)C(O)=O NSYXNHYVSQQPSD-UHFFFAOYSA-N 0.000 description 1
- AORVPBLZSJVLCI-UHFFFAOYSA-N 3,3-difluoro-1h-indol-2-one Chemical class C1=CC=C2C(F)(F)C(=O)NC2=C1 AORVPBLZSJVLCI-UHFFFAOYSA-N 0.000 description 1
- DVATXKKAJRNYBR-UHFFFAOYSA-N 3,3-difluoro-7-(trifluoromethyl)-1h-indol-2-one Chemical compound FC(F)(F)C1=CC=CC2=C1NC(=O)C2(F)F DVATXKKAJRNYBR-UHFFFAOYSA-N 0.000 description 1
- DRHSUYPMLOGVHE-UHFFFAOYSA-N 3,3-difluoro-7-methyl-1h-indol-2-one Chemical compound CC1=CC=CC2=C1NC(=O)C2(F)F DRHSUYPMLOGVHE-UHFFFAOYSA-N 0.000 description 1
- BGYAJVDNROGJEX-UHFFFAOYSA-N 3,4-difluoroindol-2-one Chemical compound FC1=CC=CC2=NC(=O)C(F)=C21 BGYAJVDNROGJEX-UHFFFAOYSA-N 0.000 description 1
- GJMPSRSMBJLKKB-UHFFFAOYSA-N 3-methylphenylacetic acid Chemical compound CC1=CC=CC(CC(O)=O)=C1 GJMPSRSMBJLKKB-UHFFFAOYSA-N 0.000 description 1
- PTVMNQPXBPQJJQ-UHFFFAOYSA-N 5-chloro-3,3-difluoro-1h-indol-2-one Chemical compound C1=C(Cl)C=C2C(F)(F)C(=O)NC2=C1 PTVMNQPXBPQJJQ-UHFFFAOYSA-N 0.000 description 1
- NHMBDKKYQAOKCR-UHFFFAOYSA-N 7-benzoyl-3-methylindol-2-one Chemical compound C12=NC(=O)C(C)=C2C=CC=C1C(=O)C1=CC=CC=C1 NHMBDKKYQAOKCR-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- LDOXTQYWWYXYSQ-UHFFFAOYSA-N Butyl phenylacetate Chemical compound CCCCOC(=O)CC1=CC=CC=C1 LDOXTQYWWYXYSQ-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241000819038 Chichester Species 0.000 description 1
- 206010015866 Extravasation Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- CRZQGDNQQAALAY-UHFFFAOYSA-N Me ester-Phenylacetic acid Natural products COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000012292 cell migration Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000036251 extravasation Effects 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SAVQQRYWWAGSQW-UHFFFAOYSA-N n-methyl-n-(trifluoro-$l^{4}-sulfanyl)methanamine Chemical compound CN(C)S(F)(F)F SAVQQRYWWAGSQW-UHFFFAOYSA-N 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 238000005935 nucleophilic addition reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 210000004224 pleura Anatomy 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/54—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/40—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/42—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to carbon atoms of at least one six-membered aromatic ring and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton with carboxyl groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR9600975A BR9600975A (pt) | 1996-03-11 | 1996-03-11 | Derivados do ácido gem-difluorfenilacético e de gem-difluorfenilacetamida processo de sua preparação e suas aplicações farmacêuticas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE1010031A5 true BE1010031A5 (fr) | 1997-11-04 |
Family
ID=38353109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE9600228A BE1010031A5 (fr) | 1996-03-11 | 1996-03-15 | Derives gem-difluoro de phenylacetamide et d'acide phenylacetique, leur preparation et leurs utilisations. |
Country Status (10)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9922830D0 (en) | 1999-09-27 | 1999-11-24 | Novartis Ag | Processes |
| JP5685384B2 (ja) * | 2010-03-29 | 2015-03-18 | 公益財団法人相模中央化学研究所 | ３，３−ジフルオロ−２，３−ジヒドロインドール−２−オン誘導体の製造方法 |
| CN108299137B (zh) * | 2018-04-09 | 2020-04-14 | 中南大学 | 一种靛红腙类化合物选择性氟化方法 |
| GB201916600D0 (en) * | 2019-11-14 | 2020-01-01 | Syngenta Crop Protection Ag | 81991-gb-reg-org-nat-1 |
| CN113698308B (zh) * | 2021-08-25 | 2024-06-21 | 山东辰龙药业有限公司 | 一种溴芬酸钠合成方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558690A (en) * | 1965-04-08 | 1971-01-26 | Gelgy Chemical Corp | Substituted derivatives of 2-anilinophenylacetic acids and a process of preparation |
| FR2499981A1 (fr) * | 1981-02-17 | 1982-08-20 | Robins Co Inc A H | Acides amino-2 halogenobenzoyl-3 methylphenylacetiques et leurs esters et sels utiles comme medicaments anti-inflammatoires et analgesiques |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3895063A (en) * | 1965-04-08 | 1975-07-15 | Ciba Geigy Corp | Substituted Anilino Benzyl Alcohols |
| US5220064A (en) * | 1986-11-26 | 1993-06-15 | Warner-Lambert Company | Substituted 4'-hydroxyphenylacetic acid derivatives having antiinflammatory and analgesic activity |
-
1996
- 1996-03-11 BR BR9600975A patent/BR9600975A/pt not_active IP Right Cessation
- 1996-03-14 GB GB9605407A patent/GB2311066B/en not_active Expired - Fee Related
- 1996-03-15 JP JP05892596A patent/JP3947242B2/ja not_active Expired - Fee Related
- 1996-03-15 BE BE9600228A patent/BE1010031A5/fr not_active IP Right Cessation
- 1996-03-15 DE DE19610357A patent/DE19610357C2/de not_active Expired - Fee Related
- 1996-03-15 ES ES009600651A patent/ES2130923B1/es not_active Expired - Fee Related
- 1996-03-15 IT IT96MI000505A patent/IT1283256B1/it active IP Right Grant
- 1996-03-15 FR FR9603314A patent/FR2745810B1/fr not_active Expired - Fee Related
- 1996-03-26 CH CH00782/96A patent/CH690722A5/fr not_active IP Right Cessation
- 1996-06-10 CN CN96108142A patent/CN1101806C/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3558690A (en) * | 1965-04-08 | 1971-01-26 | Gelgy Chemical Corp | Substituted derivatives of 2-anilinophenylacetic acids and a process of preparation |
| FR2499981A1 (fr) * | 1981-02-17 | 1982-08-20 | Robins Co Inc A H | Acides amino-2 halogenobenzoyl-3 methylphenylacetiques et leurs esters et sels utiles comme medicaments anti-inflammatoires et analgesiques |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9605407D0 (en) | 1996-05-15 |
| CN1159443A (zh) | 1997-09-17 |
| ES2130923A1 (es) | 1999-07-01 |
| DE19610357C2 (de) | 1998-08-13 |
| BR9600975A (pt) | 1997-12-30 |
| FR2745810A1 (fr) | 1997-09-12 |
| GB2311066A (en) | 1997-09-17 |
| ES2130923B1 (es) | 2000-01-16 |
| CH690722A5 (fr) | 2000-12-29 |
| FR2745810B1 (fr) | 1998-06-19 |
| JP3947242B2 (ja) | 2007-07-18 |
| CN1101806C (zh) | 2003-02-19 |
| ITMI960505A1 (it) | 1997-09-15 |
| JPH09323962A (ja) | 1997-12-16 |
| IT1283256B1 (it) | 1998-04-16 |
| DE19610357A1 (de) | 1997-09-18 |
| GB2311066B (en) | 1999-12-08 |
| ITMI960505A0 (enrdf_load_stackoverflow) | 1996-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Munavalli et al. | Trifluoromethylsulfenylation of masked carbonyl compounds | |
| Sugiura et al. | Syntheses and antiinflammatory and hypnotic activity of 5-alkoxy-3-(N-substituted carbamoyl)-1-phenylpyrazoles. 4 | |
| EP0506532B1 (fr) | Nouveaux dérivés de l'indole, procédé de préparation et médicaments les contenant | |
| CA2593613A1 (fr) | Nouveaux derives naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| EP0449699A2 (fr) | Dérivés de pyrazole antagonistes des récepteurs à l'angiotensine II, leurs procédés de préparation, compositions pharmaceutiques les contenant | |
| FR2487348A1 (fr) | Nouvelles oxazolidine-2,4-diones substituees en position 5 douees d'activite hypoglycemique | |
| Médebielle et al. | Nucleophilic difluoromethylation and trifluoromethylation using tetrakis (dimethylamino) ethylene (TDAE) reagent | |
| CA1212380A (fr) | Procede de preparation de nouveaux derives de thieno (2,3-b) pyrrole | |
| CH395065A (fr) | Procédé pour préparer des dérivés des acides polyènes-carboxyliques | |
| BE1010031A5 (fr) | Derives gem-difluoro de phenylacetamide et d'acide phenylacetique, leur preparation et leurs utilisations. | |
| EP0021940B1 (fr) | Nouveaux dérivés aminés du benzothiazole, leur procédé de préparation et leur application en thérapeutique | |
| EP0239436B1 (fr) | Nouveau dérivé tricyclique dénommé acide (chloro-3 méthyl-6 dioxo-5,5 dihydro-6, 11 dibenzo (c,f) thiazépine (1,2) yl-11 amino) -5 pentanoique, son procédé de préparation et les compositions pharmaceutiques qui le contiennent | |
| EP0348257A2 (fr) | Nouveaux dérivés d'(hétéro)aryl diazole, leur procédé de préparation et leur application en thérapeutique | |
| EP0606175B1 (fr) | Nouveaux dérivés 2-cyano 3-hydroxy propénamides, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant | |
| CH630606A5 (en) | Phenylamidine derivatives useful especially in therapeutics | |
| EP0017543B1 (fr) | Dérivés du benzothiazole, leur procédé de préparation et leurs applications en thérapeutique | |
| EP1047664B1 (fr) | Nouveaux composes tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| CH615414A5 (enrdf_load_stackoverflow) | ||
| US6034266A (en) | Gem-difluoro derivative of phenylacetamide and phenylacetic acid and their pharmaceutical uses | |
| BE828003A (fr) | Nouveaux derives d'acides amidocarboxyliques aromatiques | |
| CA2112982C (fr) | Procede de preparation des isomeres optiques d'un derive de l'amino-2 naphtyridine | |
| CH618977A5 (enrdf_load_stackoverflow) | ||
| CA2096293C (fr) | Derives d'acides alcenecarboxyliques leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| FR2478629A1 (fr) | Derives d'acides 2-cyano-ethyl-2-(n-benzoylamino) alcanoiques, leur procede de preparation et leur application en therapeutique | |
| EP0563219B1 (fr) | Procede de preparation de derives "syn" du propanamide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Effective date: 20100331 |