IL22772A - B-phenyl history with drug activity - Google Patents
B-phenyl history with drug activityInfo
- Publication number
- IL22772A IL22772A IL22772A IL2277265A IL22772A IL 22772 A IL22772 A IL 22772A IL 22772 A IL22772 A IL 22772A IL 2277265 A IL2277265 A IL 2277265A IL 22772 A IL22772 A IL 22772A
- Authority
- IL
- Israel
- Prior art keywords
- acid
- mixture
- give
- water
- distilled
- Prior art date
Links
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229910052731 fluorine Chemical group 0.000 claims 1
- 239000011737 fluorine Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 89
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
- 239000000203 mixture Substances 0.000 description 77
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000000243 solution Substances 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 19
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 18
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 235000019260 propionic acid Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- -1 diethylammonium 2' -fluoro- -biphenylylacetate Chemical compound 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000005864 Sulphur Substances 0.000 description 9
- 235000011054 acetic acid Nutrition 0.000 description 9
- 229960000192 felbinac Drugs 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 229960001138 acetylsalicylic acid Drugs 0.000 description 7
- 239000001117 sulphuric acid Substances 0.000 description 7
- 235000011149 sulphuric acid Nutrition 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 241000700159 Rattus Species 0.000 description 3
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- AYMZGPJUPSMXIN-UHFFFAOYSA-N 1-(3-methyl-4-phenylphenyl)ethanone Chemical group CC1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 AYMZGPJUPSMXIN-UHFFFAOYSA-N 0.000 description 2
- PASUFCLLJYIBHP-UHFFFAOYSA-N 1-[4-(2-fluorophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1F PASUFCLLJYIBHP-UHFFFAOYSA-N 0.000 description 2
- BRTDOUVNXYDWDL-UHFFFAOYSA-N 1-[4-(3-nitrophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC([N+]([O-])=O)=C1 BRTDOUVNXYDWDL-UHFFFAOYSA-N 0.000 description 2
- FYRPEHRWMVMHQM-UHFFFAOYSA-N 1-nitro-3-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC(C=2C=CC=CC=2)=C1 FYRPEHRWMVMHQM-UHFFFAOYSA-N 0.000 description 2
- KLMVVTUITIYVTC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)phenyl]-3-ethoxy-3-oxopropanoic acid Chemical compound CCOC(=O)C(C1=CC=C(C=C1)C2=CC=C(C=C2)Cl)C(=O)O KLMVVTUITIYVTC-UHFFFAOYSA-N 0.000 description 2
- HNMVDGFMLKHLPJ-UHFFFAOYSA-N 3-methyl-4-phenylbenzonitrile Chemical group CC1=CC(C#N)=CC=C1C1=CC=CC=C1 HNMVDGFMLKHLPJ-UHFFFAOYSA-N 0.000 description 2
- DJPSGVHDXUACIA-UHFFFAOYSA-N 4-chloro-2-methyl-1-phenylbenzene Chemical group CC1=CC(Cl)=CC=C1C1=CC=CC=C1 DJPSGVHDXUACIA-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- 206010053155 Epigastric discomfort Diseases 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- AZIXCCZIYUFQOY-UHFFFAOYSA-N (1-nitrocyclohexa-2,4-dien-1-yl)benzene Chemical group C=1C=CC=CC=1C1([N+](=O)[O-])CC=CC=C1 AZIXCCZIYUFQOY-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- RFHQDKCYTRLWBB-UHFFFAOYSA-N 1-(3-amino-4-phenylphenyl)ethanone Chemical group NC1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 RFHQDKCYTRLWBB-UHFFFAOYSA-N 0.000 description 1
- KQNNNDZVEYLTHF-UHFFFAOYSA-N 1-[4-(2-chlorophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1Cl KQNNNDZVEYLTHF-UHFFFAOYSA-N 0.000 description 1
- QPWPWLUCJKNVKY-UHFFFAOYSA-N 1-[4-(3-aminophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC(N)=C1 QPWPWLUCJKNVKY-UHFFFAOYSA-N 0.000 description 1
- DUFBYEORCCIAEY-UHFFFAOYSA-N 1-[4-(3-chlorophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC(Cl)=C1 DUFBYEORCCIAEY-UHFFFAOYSA-N 0.000 description 1
- CBMCNPAMKBMCBO-UHFFFAOYSA-N 1-[4-(3-fluorophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC(F)=C1 CBMCNPAMKBMCBO-UHFFFAOYSA-N 0.000 description 1
- NPGUSEJJJVVVME-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)phenyl]ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=C(Cl)C=C1 NPGUSEJJJVVVME-UHFFFAOYSA-N 0.000 description 1
- KLECYOQFQXJYBC-UHFFFAOYSA-N 1-fluoro-2-phenylbenzene Chemical group FC1=CC=CC=C1C1=CC=CC=C1 KLECYOQFQXJYBC-UHFFFAOYSA-N 0.000 description 1
- MRCAAFFMZODJBP-UHFFFAOYSA-N 1-fluoro-3-phenylbenzene Chemical group FC1=CC=CC(C=2C=CC=CC=2)=C1 MRCAAFFMZODJBP-UHFFFAOYSA-N 0.000 description 1
- YOJKKXRJMXIKSR-UHFFFAOYSA-N 1-nitro-2-phenylbenzene Chemical group [O-][N+](=O)C1=CC=CC=C1C1=CC=CC=C1 YOJKKXRJMXIKSR-UHFFFAOYSA-N 0.000 description 1
- QOHBDSNZJFUVAS-UHFFFAOYSA-N 2-(2-aminophenyl)-6-bromoaniline Chemical group Nc1ccccc1-c1cccc(Br)c1N QOHBDSNZJFUVAS-UHFFFAOYSA-N 0.000 description 1
- AAMWFJUMCNIECU-UHFFFAOYSA-N 2-(2-chloro-4-phenylphenyl)acetic acid Chemical compound C1=C(Cl)C(CC(=O)O)=CC=C1C1=CC=CC=C1 AAMWFJUMCNIECU-UHFFFAOYSA-N 0.000 description 1
- MZSNDIIUILXNMA-UHFFFAOYSA-N 2-(2-fluoro-4-phenylphenyl)acetic acid Chemical compound C1=C(F)C(CC(=O)O)=CC=C1C1=CC=CC=C1 MZSNDIIUILXNMA-UHFFFAOYSA-N 0.000 description 1
- RXBBBPKHEJKXHR-UHFFFAOYSA-N 2-(2-methoxy-3-phenylphenyl)acetic acid Chemical compound COC1=C(CC(O)=O)C=CC=C1C1=CC=CC=C1 RXBBBPKHEJKXHR-UHFFFAOYSA-N 0.000 description 1
- RLBGWKIRJJAWPC-UHFFFAOYSA-N 2-(2-methoxy-4-phenylphenyl)acetic acid Chemical compound C1=C(CC(O)=O)C(OC)=CC(C=2C=CC=CC=2)=C1 RLBGWKIRJJAWPC-UHFFFAOYSA-N 0.000 description 1
- RZZQPDWRAYBGCE-UHFFFAOYSA-N 2-(2-methyl-3-phenylphenyl)acetic acid Chemical compound CC1=C(CC(O)=O)C=CC=C1C1=CC=CC=C1 RZZQPDWRAYBGCE-UHFFFAOYSA-N 0.000 description 1
- WVYPDPJNPRIPPW-UHFFFAOYSA-N 2-(2-phenylphenyl)acetonitrile Chemical compound N#CCC1=CC=CC=C1C1=CC=CC=C1 WVYPDPJNPRIPPW-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- VMLQUQQCJJEKQK-UHFFFAOYSA-N 2-(3-cyano-4-phenylphenyl)acetic acid Chemical compound C(#N)C1=C(C=CC(=C1)CC(=O)O)C1=CC=CC=C1 VMLQUQQCJJEKQK-UHFFFAOYSA-N 0.000 description 1
- UTCSBBDZYOJADB-UHFFFAOYSA-N 2-(3-ethyl-4-phenylphenyl)acetic acid Chemical compound CCC1=CC(CC(O)=O)=CC=C1C1=CC=CC=C1 UTCSBBDZYOJADB-UHFFFAOYSA-N 0.000 description 1
- ZLLZRKQQNGBXRD-UHFFFAOYSA-N 2-(3-fluoro-4-phenylphenyl)acetic acid Chemical compound FC1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1 ZLLZRKQQNGBXRD-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- QSORQSLEAOIDLH-UHFFFAOYSA-N 2-(3-methoxy-4-phenylphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1C1=CC=CC=C1 QSORQSLEAOIDLH-UHFFFAOYSA-N 0.000 description 1
- FECKFPONVUPYSQ-UHFFFAOYSA-N 2-(3-nitro-4-phenylphenyl)acetic acid Chemical compound [O-][N+](=O)C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1 FECKFPONVUPYSQ-UHFFFAOYSA-N 0.000 description 1
- GJLGGECBUUNDNQ-UHFFFAOYSA-N 2-(4-phenylphenyl)prop-2-enoic acid Chemical compound C1=CC(C(=C)C(=O)O)=CC=C1C1=CC=CC=C1 GJLGGECBUUNDNQ-UHFFFAOYSA-N 0.000 description 1
- WTGWHMMQWMLFMZ-UHFFFAOYSA-N 2-(4-phenylphenyl)propanedioic acid Chemical compound C1=CC(C(C(O)=O)C(=O)O)=CC=C1C1=CC=CC=C1 WTGWHMMQWMLFMZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CLLYNFVIUFPDEM-UHFFFAOYSA-N 2-[2-(2-hydroxyphenyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C1=CC=CC=C1O CLLYNFVIUFPDEM-UHFFFAOYSA-N 0.000 description 1
- BFGLWNMRGCKEOE-UHFFFAOYSA-N 2-[2-(3-fluorophenyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C1=CC=CC(F)=C1 BFGLWNMRGCKEOE-UHFFFAOYSA-N 0.000 description 1
- UQDARKFHSLZZIE-UHFFFAOYSA-N 2-[3-fluoro-4-(2-fluorophenyl)phenyl]acetic acid Chemical compound FC1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1F UQDARKFHSLZZIE-UHFFFAOYSA-N 0.000 description 1
- LVPVQWLQXQTXCJ-UHFFFAOYSA-N 2-[4-(2-chlorophenyl)phenyl]-3-ethoxy-3-oxopropanoic acid Chemical compound CCOC(C(C(O)=O)C(C=C1)=CC=C1C(C=CC=C1)=C1Cl)=O LVPVQWLQXQTXCJ-UHFFFAOYSA-N 0.000 description 1
- QCNVQJYOSMHROS-UHFFFAOYSA-N 2-[4-(2-chlorophenyl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1Cl QCNVQJYOSMHROS-UHFFFAOYSA-N 0.000 description 1
- HSOKOZJRZALFLQ-UHFFFAOYSA-N 2-[4-(2-fluorophenyl)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=C1F HSOKOZJRZALFLQ-UHFFFAOYSA-N 0.000 description 1
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- SRIBJRZQDFBVQC-UHFFFAOYSA-N methyl 2-(4-phenylphenyl)acetate Chemical compound C1=CC(CC(=O)OC)=CC=C1C1=CC=CC=C1 SRIBJRZQDFBVQC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
- C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
- C07C205/12—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings the six-membered aromatic ring or a condensed ring system containing that ring being substituted by halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
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- C07—ORGANIC CHEMISTRY
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- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C07C33/48—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts with unsaturation outside the aromatic rings
- C07C33/486—Polycyclic
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3223/64A GB1091403A (en) | 1964-01-24 | 1964-01-24 | Therapeutically active phenylalkane derivatives |
US42562465A | 1965-01-14 | 1965-01-14 | |
US84503369A | 1969-07-25 | 1969-07-25 | |
US00885280A US3821293A (en) | 1964-01-24 | 1969-12-15 | 2-(4'-chloro-4-biphenylyl)propionic acid |
US30855872A | 1972-11-12 | 1972-11-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
IL22772A true IL22772A (en) | 1969-02-27 |
Family
ID=27515717
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL22772A IL22772A (en) | 1964-01-24 | 1965-01-12 | B-phenyl history with drug activity |
Country Status (12)
Country | Link |
---|---|
US (3) | US3755427A (en, 2012) |
BE (1) | BE658723A (en, 2012) |
CH (1) | CH454822A (en, 2012) |
CS (2) | CS163156B2 (en, 2012) |
DE (1) | DE1518528B2 (en, 2012) |
DK (2) | DK127251B (en, 2012) |
FI (1) | FI42712C (en, 2012) |
FR (3) | FR5737M (en, 2012) |
GB (1) | GB1091403A (en, 2012) |
IL (1) | IL22772A (en, 2012) |
NL (1) | NL152540B (en, 2012) |
SE (2) | SE324759B (en, 2012) |
Families Citing this family (79)
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US4053639A (en) * | 1964-01-24 | 1977-10-11 | The Boots Company Limited | Therapeutically active phenylalkane derivatives |
FR2043467A1 (en, 2012) * | 1969-05-12 | 1971-02-19 | Clin Byla Ets | |
US3671580A (en) * | 1969-12-22 | 1972-06-20 | Merck & Co Inc | Substituted biphenyl acetic acids and ester derivatives thereof |
GB1312642A (en) * | 1970-07-13 | 1973-04-04 | Science Union & Cie | Pyrazole compounds and process for their manufacture |
GB1359987A (en) * | 1970-10-12 | 1974-07-17 | Boots Co Ltd | 2-substituted biphenylyl propionic acids |
FR2115026B1 (en, 2012) * | 1970-11-24 | 1974-03-22 | Logeais Labor Jacques | |
US4052514A (en) * | 1971-03-26 | 1977-10-04 | The Boots Company Limited | Trihalosubstituted biphenylyl propionic acids |
DE2205732A1 (de) * | 1972-02-08 | 1973-08-16 | Thomae Gmbh Dr K | Neue 4-(4-biphenylyl)-butensaeurederivate |
US4048332A (en) * | 1972-06-15 | 1977-09-13 | The Boots Company Limited | Phenylalkanoic acids |
GB1396726A (en) * | 1972-06-15 | 1975-06-04 | Boots Co Ltd | Phenylalkanoic acids |
ATA785173A (de) * | 1972-08-17 | 1975-01-15 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen 4-(4-biphenylyl)-4-hydroxy-buttersaeureamiden |
US3987197A (en) * | 1972-08-17 | 1976-10-19 | Boehringer Ingelheim Gmbh | 3-(2'-fluoro-4-biphenylyl)-butyric acid and salts thereof |
US3957861A (en) * | 1973-11-07 | 1976-05-18 | The Upjohn Company | Biphenylylpropionic acids and esters |
ES446581A1 (es) * | 1975-04-04 | 1977-06-16 | Boots Co Ltd | Un procedimiento para preparar acidos 2-arilpropionicos. |
US4371473A (en) * | 1979-06-28 | 1983-02-01 | Ethyl Corporation | Preparation of 2-(2-fluoro-4-biphenylyl)propionic acid and corresponding nitride |
US4278516A (en) * | 1979-06-28 | 1981-07-14 | Ethyl Corporation | Method for the preparation of 2-fluoro-4-monobromomethylbiphenyl |
EP0089426B1 (en) * | 1979-07-12 | 1986-06-11 | A.H. Robins Company, Incorporated | 2-amino-6-biphenylacetic acids |
US4230724A (en) * | 1979-07-16 | 1980-10-28 | Allergan Pharmaceuticals, Inc. | Method of treating vascularization of the eye with Flurbiprofen |
US4324904A (en) * | 1979-12-19 | 1982-04-13 | The Upjohn Company | Processes for the preparation of hydratropic acids and esters |
NL8006488A (nl) * | 1979-12-19 | 1981-07-16 | Upjohn Co | Werkwijze voor het bereiden van arylpropionzuren. |
GB2075837B (en) * | 1980-05-14 | 1984-03-14 | Hisamitsu Pharmaceutical Co | Topical pharmaceutical gel containing anti-inflammatory analgesic agents |
DE3026402A1 (de) * | 1980-07-11 | 1982-02-04 | Syntex Corp., Palo Alto, Calif. | Die verwendung analgetischer und nicht-hormonaler, entzuendungshemmender mittel bei der behandlung von mikrovaskulaeren erkrankungen |
US4422979A (en) * | 1980-09-22 | 1983-12-27 | Ethyl Corporation | Fluoro-substituted biphenylyl compounds and processes |
US4443476A (en) * | 1981-07-20 | 1984-04-17 | The Upjohn Company | Treatment of adult respiratory distress syndrome |
FR2514355A1 (fr) * | 1981-10-14 | 1983-04-15 | Fabre Sa Pierre | Derives de biphenyl alcoyl carboxylates, leur procede de preparation et leur utilisation comme medicaments |
US4502995A (en) * | 1981-11-02 | 1985-03-05 | Ethyl Corporation | Nucleophilic substitution process |
US4370278A (en) * | 1981-11-02 | 1983-01-25 | Ethyl Corporation | Nucleophilic substitution process |
ZA828453B (en) * | 1981-12-08 | 1983-12-28 | Boots Co Plc | Therapeutic agents |
DE3209178A1 (de) * | 1982-03-13 | 1983-09-15 | Merck Patent Gmbh, 6100 Darmstadt | Polyhalogenaromaten |
FR2524463A1 (fr) * | 1982-04-05 | 1983-10-07 | Fabre Sa Pierre | Obtention du metbufene par synthese malonique |
US4404211A (en) * | 1982-06-30 | 1983-09-13 | E. I. Du Pont De Nemours And Company | Analgesic mixture of nalbuphine and flurbiprofen |
CA1201127A (en) * | 1982-09-10 | 1986-02-25 | Katsuhiro Uchida | Biphenylylpropionic acid derivative, process for preparing the same and pharmaceutical composition containing the same |
JPS59152348A (ja) * | 1983-02-19 | 1984-08-31 | Kaken Pharmaceut Co Ltd | ビフエニリルプロピオン酸エステル誘導体およびその製造法 |
US5196567A (en) * | 1983-02-19 | 1993-03-23 | Kaken Pharmaceutical Co., Ltd. | Biphenylylpropionic acid derivative, process for preparing the same and pharmaceutical composition containing the same |
US4540795A (en) * | 1983-02-25 | 1985-09-10 | Ethyl Corporation | Fluoronitroaralkyloxazolines, derivatives thereof, and nucleophilic substitution processes for preparing them |
IT1194209B (it) * | 1983-04-21 | 1988-09-14 | Medea Res Srl | Composti fluorurati ad attivita' analgesica e antiinfiammatoria |
IT1212821B (it) * | 1983-06-03 | 1989-11-30 | Scharper Spa | Derivati dell'acido fenil-etil-acetico ad attivita'antiinfiammatoria. |
JPS601122A (ja) * | 1983-06-20 | 1985-01-07 | Green Cross Corp:The | ビフエニリルプロピオン酸誘導体脂肪乳剤 |
FR2564459B1 (fr) * | 1984-05-16 | 1986-10-31 | Delalande Sa | Procede de preparation d'acides hydratropiques et de leurs esters, a partir de propiophenones |
US5286751A (en) * | 1987-12-24 | 1994-02-15 | Analgesic Associates | Sustained/enhanced antipyretic response |
US4927854A (en) * | 1987-12-24 | 1990-05-22 | Analgesic Associates | Sustained/enhanced analgesia |
AU659106B2 (en) * | 1990-11-06 | 1995-05-11 | Fgn, Inc. | Method for treating colonic polyps by the use of esters and amides of substituted phenyl and pyridyl amino carboxylates |
US6160018A (en) * | 1995-03-13 | 2000-12-12 | Loma Linda University Medical Center | Prophylactic composition and method for alzheimer's Disease |
US5955504A (en) * | 1995-03-13 | 1999-09-21 | Loma Linda University Medical Center | Colorectal chemoprotective composition and method of preventing colorectal cancer |
US5981592A (en) * | 1995-03-13 | 1999-11-09 | Loma Linda University Medical Center | Method and composition for treating cystic fibrosis |
GB9523833D0 (en) * | 1995-11-22 | 1996-01-24 | Boots Co Plc | Medical treatment |
US6348216B1 (en) * | 1996-06-10 | 2002-02-19 | Knoll Pharmaceutical Company | Ibuprofen and narcotic analgesic compositions |
US6361794B1 (en) | 1996-06-12 | 2002-03-26 | Basf Corporation | Method of making ibuprofen and narcotic analgesic composition |
US5792886A (en) * | 1997-01-08 | 1998-08-11 | Albemarle Corporation | Production of racemic 2-(6-methoxy-2-naphthyl) propionic acid of precursors thereof |
US6080888A (en) * | 1997-01-08 | 2000-06-27 | Albemarle Corporation | Preparation of olefinic compounds and carboxylic derivatives thereof |
US6096920A (en) * | 1997-01-08 | 2000-08-01 | Albemarle Corporation | Preparation of carboxylic compounds and their derivatives |
US5994379A (en) * | 1998-02-13 | 1999-11-30 | Merck Frosst Canada, Inc. | Bisaryl COX-2 inhibiting compounds, compositions and methods of use |
DE19808261A1 (de) * | 1998-02-27 | 1999-10-28 | Bayer Ag | Arylphenylsubstituierte cyclische Ketoenole |
US6268526B1 (en) | 1998-12-16 | 2001-07-31 | Albemarle Corporation | Palladium catalyzed carbonylation process utilizing aromatic substituted alcohols and/or aromatic substituted alkyl halides |
IT1308633B1 (it) | 1999-03-02 | 2002-01-09 | Nicox Sa | Nitrossiderivati. |
EP1284729A4 (en) * | 2000-04-13 | 2007-12-19 | Mayo Foundation | REDUCTION AGENTS OF A (BETA) 42 |
FR2811664B1 (fr) * | 2000-07-17 | 2002-09-13 | Rhodia Chimie Sa | Procede de preparation d'un compose polyaromatique |
IT1318674B1 (it) * | 2000-08-08 | 2003-08-27 | Nicox Sa | Faramaci per l'incontinenza. |
IT1318673B1 (it) * | 2000-08-08 | 2003-08-27 | Nicox Sa | Farmaci per le disfunzioni sessuali. |
US6646003B2 (en) | 2001-04-02 | 2003-11-11 | Alcon, Inc. | Method of treating ocular inflammatory and angiogenesis-related disorders of the posterior segment of the eye using an amide derivative of flurbiprofen or ketorolac |
US20030027867A1 (en) * | 2001-06-29 | 2003-02-06 | Myriad Genetics, Incorporated | Use of R-NSAID compounds for anti-HIV treatment |
TW200413009A (en) * | 2002-10-04 | 2004-08-01 | Univ Pennsylvania | Biphenyls and fluorenes as imaging agents in alzheimer's disease |
JP2006335639A (ja) * | 2003-01-23 | 2006-12-14 | Nagase & Co Ltd | 光学活性なフルルビプロフェンの製造方法 |
WO2004071431A2 (en) * | 2003-02-05 | 2004-08-26 | Myriad Genetics, Inc. | Method and composition for treating neurodegenerative disorders |
JP2007528857A (ja) * | 2003-07-11 | 2007-10-18 | ミリアド ジェネティクス, インコーポレイテッド | アルツハイマー病の処置のための薬学的方法、投与レジメンおよび投薬形態 |
US20050171207A1 (en) * | 2003-09-26 | 2005-08-04 | Myriad Genetics, Incorporated | Method and composition for combination treatment of neurodegenerative disorders |
WO2006001877A2 (en) * | 2004-04-13 | 2006-01-05 | Myriad Genetics, Inc. | Combination treatment for neurodegenerative disorders comprising r-flurbiprofen |
CN1946906A (zh) * | 2004-04-29 | 2007-04-11 | 吉斯通护岸系统股份有限公司 | 用于墙、护墙和类似物的饰面 |
WO2006020853A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
WO2006020852A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
WO2006020850A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
WO2006021441A1 (en) * | 2004-08-25 | 2006-03-02 | Cellzome Ag | Biphenyl-carboxylic acids and derivatives thereof and their use in therapy |
US20070015832A1 (en) * | 2005-07-14 | 2007-01-18 | Myriad Genetics, Incorporated | Methods of treating overactive bladder and urinary incontinence |
US20080033045A1 (en) * | 2006-07-07 | 2008-02-07 | Myriad Genetics, Incorporated | Treatment of psychiatric disorders |
EP2117302A1 (en) * | 2007-02-01 | 2009-11-18 | Myriad Genetics, Inc. | Drug substance preparations, pharmaceutical compositions and dosage forms |
EA201491238A1 (ru) | 2012-01-31 | 2014-12-30 | Сановел Илач Санайи Ве Тиджарет Аноним Ширкети | Новая фармацевтическая композиция флурбипрофена и глюкозамина |
US20150359814A1 (en) | 2013-01-28 | 2015-12-17 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Pharmaceutical Combinations of Flurbiprofen, Glucosamin and Capsaicin |
CN109553533A (zh) * | 2017-09-27 | 2019-04-02 | 江苏瑞科医药科技有限公司 | 氟比洛芬中间体及其制备方法 |
CN116875296A (zh) * | 2023-09-08 | 2023-10-13 | 东营玺诺石油科技有限公司 | 一种储层改造用固态酸前体 |
-
1964
- 1964-01-24 GB GB3223/64A patent/GB1091403A/en not_active Expired
-
1965
- 1965-01-12 IL IL22772A patent/IL22772A/en unknown
- 1965-01-19 DE DE1518528A patent/DE1518528B2/de active Granted
- 1965-01-22 NL NL656500865A patent/NL152540B/xx not_active IP Right Cessation
- 1965-01-22 FI FI650151A patent/FI42712C/fi active
- 1965-01-22 CH CH92065A patent/CH454822A/fr unknown
- 1965-01-22 SE SE855/65A patent/SE324759B/xx unknown
- 1965-01-22 BE BE658723D patent/BE658723A/xx unknown
- 1965-01-22 FR FR2895A patent/FR5737M/fr not_active Expired
- 1965-01-22 FR FR2899A patent/FR1430359A/fr not_active Expired
- 1965-01-23 DK DK38265AA patent/DK127251B/da unknown
- 1965-01-25 CS CS508A patent/CS163156B2/cs unknown
- 1965-01-25 CS CS173A patent/CS163157B2/cs unknown
-
1966
- 1966-04-14 DK DK191466AA patent/DK116794B/da unknown
- 1966-06-28 FR FR67159A patent/FR5738M/fr not_active Expired
-
1967
- 1967-06-30 SE SE10115/67A patent/SE329843B/xx unknown
-
1969
- 1969-07-25 US US00845033A patent/US3755427A/en not_active Expired - Lifetime
- 1969-12-15 US US00885280A patent/US3821293A/en not_active Expired - Lifetime
-
1972
- 1972-11-21 US US00308558A patent/US3793457A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
DK116794B (da) | 1970-02-16 |
GB1091403A (en) | 1967-11-15 |
FR5738M (en, 2012) | 1968-01-29 |
DE1518528A1 (de) | 1969-02-27 |
NL6500865A (en, 2012) | 1965-07-26 |
DK127251B (da) | 1973-10-08 |
DE1518528B2 (de) | 1974-04-18 |
US3793457A (en) | 1974-02-19 |
CS163157B2 (en, 2012) | 1975-08-29 |
FI42712C (fi) | 1970-10-12 |
CS163156B2 (en, 2012) | 1975-08-29 |
US3821293A (en) | 1974-06-28 |
FR1430359A (fr) | 1966-03-04 |
BE658723A (en, 2012) | 1965-07-22 |
NL152540B (nl) | 1977-03-15 |
SE324759B (en, 2012) | 1970-06-15 |
SE329843B (en, 2012) | 1970-10-26 |
DE1518528C3 (en, 2012) | 1974-12-05 |
US3755427A (en) | 1973-08-28 |
FR5737M (en, 2012) | 1968-03-04 |
CH454822A (fr) | 1968-04-30 |
FI42712B (en, 2012) | 1970-06-30 |
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