CH621783A5 - Process for the preparation of novel thiazolines - Google Patents
Process for the preparation of novel thiazolines Download PDFInfo
- Publication number
- CH621783A5 CH621783A5 CH1587975A CH1587975A CH621783A5 CH 621783 A5 CH621783 A5 CH 621783A5 CH 1587975 A CH1587975 A CH 1587975A CH 1587975 A CH1587975 A CH 1587975A CH 621783 A5 CH621783 A5 CH 621783A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- thiazolin
- acid
- ylidenamino
- propionic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000003549 thiazolines Chemical class 0.000 title claims description 9
- -1 alkenyl halide Chemical class 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000005956 quaternization reaction Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 81
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 235000019260 propionic acid Nutrition 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 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 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000000460 chlorine Substances 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000000047 product Substances 0.000 description 19
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229910001868 water Inorganic materials 0.000 description 13
- 239000011575 calcium Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 5
- 241000700157 Rattus norvegicus Species 0.000 description 5
- 230000001754 anti-pyretic effect Effects 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- 101150046236 CNR1 gene Proteins 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229960005069 calcium Drugs 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 159000000007 calcium salts Chemical class 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 150000002148 esters Chemical group 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000003356 anti-rheumatic effect Effects 0.000 description 3
- 239000003435 antirheumatic agent Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006114 decarboxylation reaction Methods 0.000 description 3
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VSAMEASAFWDALV-UHFFFAOYSA-N 2-[2-chloro-4-[(3-methyl-1,3-thiazol-2-ylidene)amino]phenyl]propanoic acid Chemical compound C1=C(Cl)C(C(C(O)=O)C)=CC=C1N=C1N(C)C=CS1 VSAMEASAFWDALV-UHFFFAOYSA-N 0.000 description 2
- JOSHLQDNYLKFLI-UHFFFAOYSA-N 2-[3,5-dichloro-4-[(3-methyl-1,3-thiazol-2-ylidene)amino]phenyl]propanoic acid Chemical compound ClC1=CC(C(C(O)=O)C)=CC(Cl)=C1N=C1N(C)C=CS1 JOSHLQDNYLKFLI-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- BXMWERGPZXWTRC-UHFFFAOYSA-N 3-methyl-N-phenyl-1,3-thiazol-2-imine Chemical compound CN1C(SC=C1)=NC1=CC=CC=C1 BXMWERGPZXWTRC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 230000003501 anti-edematous effect Effects 0.000 description 2
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 2
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229960000905 indomethacin Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 2
- 229960003464 mefenamic acid Drugs 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000036407 pain Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- QTFLUVRZOBQTBW-UHFFFAOYSA-N 1,3-thiazol-3-ium;iodide Chemical compound [I-].C1=CSC=[NH+]1 QTFLUVRZOBQTBW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FGIWHTCTNZVPQF-UHFFFAOYSA-N 2-(2-phenylimino-3-prop-2-enyl-1,3-thiazol-5-yl)propanoic acid Chemical compound S1C(C(C(O)=O)C)=CN(CC=C)C1=NC1=CC=CC=C1 FGIWHTCTNZVPQF-UHFFFAOYSA-N 0.000 description 1
- HRSNKNPBIYJDNS-UHFFFAOYSA-N 2-(2-phenylimino-3-propyl-1,3-thiazol-5-yl)propanoic acid Chemical compound CCCN1C=C(C(C)C(O)=O)SC1=NC1=CC=CC=C1 HRSNKNPBIYJDNS-UHFFFAOYSA-N 0.000 description 1
- ZYXSFDALQHXLMA-UHFFFAOYSA-N 2-(3,4-dimethyl-2-phenylimino-1,3-thiazol-5-yl)acetic acid Chemical compound CN1C(C)=C(CC(O)=O)SC1=NC1=CC=CC=C1 ZYXSFDALQHXLMA-UHFFFAOYSA-N 0.000 description 1
- MUTMTEHCFFZEQI-UHFFFAOYSA-N 2-(3-ethyl-4-methyl-2-phenylimino-1,3-thiazol-5-yl)propanoic acid Chemical compound CCN1C(C)=C(C(C)C(O)=O)SC1=NC1=CC=CC=C1 MUTMTEHCFFZEQI-UHFFFAOYSA-N 0.000 description 1
- KTTIMYFUBPWMQM-UHFFFAOYSA-N 2-(3-methyl-2-phenylimino-1,3-thiazol-5-yl)butanoic acid Chemical compound S1C(C(C(O)=O)CC)=CN(C)C1=NC1=CC=CC=C1 KTTIMYFUBPWMQM-UHFFFAOYSA-N 0.000 description 1
- NSRJCEKTVSQAKN-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)imino-3,4-dimethyl-1,3-thiazol-5-yl]propanoic acid Chemical compound CN1C(C)=C(C(C(O)=O)C)SC1=NC1=CC=CC=C1F NSRJCEKTVSQAKN-UHFFFAOYSA-N 0.000 description 1
- TUHLAJYQLQCXSR-UHFFFAOYSA-N 2-[2-(2-fluorophenyl)imino-3-prop-2-enyl-1,3-thiazol-4-yl]propanoic acid Chemical compound C=CCN1C(C(C(O)=O)C)=CSC1=NC1=CC=CC=C1F TUHLAJYQLQCXSR-UHFFFAOYSA-N 0.000 description 1
- XMIRJZAREAWJII-UHFFFAOYSA-N 2-[2-(3,5-dichlorophenyl)imino-3,4-dimethyl-1,3-thiazol-5-yl]propanoic acid Chemical compound CN1C(C)=C(C(C(O)=O)C)SC1=NC1=CC(Cl)=CC(Cl)=C1 XMIRJZAREAWJII-UHFFFAOYSA-N 0.000 description 1
- SIFXXUPQFVBALR-UHFFFAOYSA-N 2-[2-(3,5-dichlorophenyl)imino-3,5-dimethyl-1,3-thiazol-4-yl]acetic acid Chemical compound CN1C(CC(O)=O)=C(C)SC1=NC1=CC(Cl)=CC(Cl)=C1 SIFXXUPQFVBALR-UHFFFAOYSA-N 0.000 description 1
- HFILEJHAFSRKPC-UHFFFAOYSA-N 2-[2-(3,5-dichlorophenyl)imino-3-methyl-1,3-thiazol-5-yl]acetic acid Chemical compound CN1C=C(CC(O)=O)SC1=NC1=CC(Cl)=CC(Cl)=C1 HFILEJHAFSRKPC-UHFFFAOYSA-N 0.000 description 1
- NTVUJQIFIWPONH-UHFFFAOYSA-N 2-[2-(3,5-dimethylphenyl)imino-3-ethyl-1,3-thiazol-5-yl]propanoic acid Chemical compound CCN1C=C(C(C)C(O)=O)SC1=NC1=CC(C)=CC(C)=C1 NTVUJQIFIWPONH-UHFFFAOYSA-N 0.000 description 1
- UIBINQAFYPTFDA-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)imino-3,4-dimethyl-1,3-thiazol-5-yl]acetic acid Chemical compound ClC1=CC=C(C=C1)N=C1SC(=C(N1C)C)CC(=O)O UIBINQAFYPTFDA-UHFFFAOYSA-N 0.000 description 1
- GUHLJAGPZVVHHJ-UHFFFAOYSA-N 2-[2-fluoro-4-[(3-methyl-1,3-thiazol-2-ylidene)amino]phenyl]butanoic acid Chemical compound C1=C(F)C(C(C(O)=O)CC)=CC=C1N=C1N(C)C=CS1 GUHLJAGPZVVHHJ-UHFFFAOYSA-N 0.000 description 1
- HZGKMMSOHGLKTO-UHFFFAOYSA-N 2-[2-fluoro-4-[(3-methyl-1,3-thiazol-2-ylidene)amino]phenyl]propanoic acid Chemical compound C1=C(F)C(C(C(O)=O)C)=CC=C1N=C1N(C)C=CS1 HZGKMMSOHGLKTO-UHFFFAOYSA-N 0.000 description 1
- KYKVWHAMFWOHEH-UHFFFAOYSA-N 2-[2-fluoro-5-[(3-methyl-1,3-thiazol-2-ylidene)amino]phenyl]butanoic acid Chemical compound C1=C(F)C(C(C(O)=O)CC)=CC(N=C2N(C=CS2)C)=C1 KYKVWHAMFWOHEH-UHFFFAOYSA-N 0.000 description 1
- OQXNJGUGCIWSDX-UHFFFAOYSA-N 2-[2-methoxy-4-[(3-methyl-1,3-thiazol-2-ylidene)amino]phenyl]acetic acid Chemical compound C1=C(CC(O)=O)C(OC)=CC(N=C2N(C=CS2)C)=C1 OQXNJGUGCIWSDX-UHFFFAOYSA-N 0.000 description 1
- SNQHXNNETWCXBQ-UHFFFAOYSA-N 2-[2-methyl-4-[(3-methyl-1,3-thiazol-2-ylidene)amino]phenyl]propanoic acid Chemical compound C1=C(C)C(C(C(O)=O)C)=CC=C1N=C1N(C)C=CS1 SNQHXNNETWCXBQ-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
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- 238000000921 elemental analysis Methods 0.000 description 1
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- MHUFFBFRRKVBJM-UHFFFAOYSA-N ethyl 2-(2-anilino-1,3-thiazol-4-yl)propanoate Chemical compound CCOC(=O)C(C)C1=CSC(NC=2C=CC=CC=2)=N1 MHUFFBFRRKVBJM-UHFFFAOYSA-N 0.000 description 1
- SRBWPGFQLZTHDW-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[(3-methyl-1,3-thiazol-3-ium-2-yl)amino]phenyl]acetate;iodide Chemical compound [I-].ClC1=CC(CC(=O)OCC)=CC=C1NC1=[N+](C)C=CS1 SRBWPGFQLZTHDW-UHFFFAOYSA-N 0.000 description 1
- TTZIIWWXEFZOIM-UHFFFAOYSA-N ethyl 2-[4-[(3-methyl-1,3-thiazol-3-ium-2-yl)amino]phenyl]propanoate;iodide Chemical compound [I-].C1=CC(C(C)C(=O)OCC)=CC=C1NC1=[N+](C)C=CS1 TTZIIWWXEFZOIM-UHFFFAOYSA-N 0.000 description 1
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- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 206010033675 panniculitis Diseases 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 210000004304 subcutaneous tissue Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49140776A JPS5175065A (enrdf_load_stackoverflow) | 1974-12-06 | 1974-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621783A5 true CH621783A5 (en) | 1981-02-27 |
Family
ID=15276473
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1587975A CH621783A5 (en) | 1974-12-06 | 1975-12-05 | Process for the preparation of novel thiazolines |
| CH677280A CH624109A5 (en) | 1974-12-06 | 1980-09-09 | Process for the preparation of novel thiazolines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH677280A CH624109A5 (en) | 1974-12-06 | 1980-09-09 | Process for the preparation of novel thiazolines |
Country Status (10)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6339868A (ja) * | 1986-08-04 | 1988-02-20 | Otsuka Pharmaceut Factory Inc | ジ低級アルキルフエノ−ル誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1262292A (en) * | 1968-04-09 | 1972-02-02 | Wyeth John & Brother Ltd | Novel thiazoline derivatives, the preparation thereof and compositions containing the same |
-
1974
- 1974-12-06 JP JP49140776A patent/JPS5175065A/ja active Pending
-
1975
- 1975-11-27 CA CA240,770A patent/CA1060024A/en not_active Expired
- 1975-11-28 GB GB4909475A patent/GB1476594A/en not_active Expired
- 1975-12-02 SE SE7513574A patent/SE430064B/xx not_active IP Right Cessation
- 1975-12-04 AU AU87275/75A patent/AU502387B2/en not_active Expired
- 1975-12-05 CH CH1587975A patent/CH621783A5/de not_active IP Right Cessation
- 1975-12-05 DK DK551275A patent/DK144473C/da not_active IP Right Cessation
- 1975-12-05 DE DE2554863A patent/DE2554863C2/de not_active Expired
- 1975-12-05 FR FR7537369A patent/FR2293200A1/fr active Granted
- 1975-12-08 NL NL7514284A patent/NL7514284A/xx not_active Application Discontinuation
-
1980
- 1980-09-09 CH CH677280A patent/CH624109A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2554863A1 (de) | 1976-06-16 |
| FR2293200B1 (enrdf_load_stackoverflow) | 1978-07-28 |
| DK144473C (da) | 1982-08-30 |
| FR2293200A1 (fr) | 1976-07-02 |
| SE7513574L (sv) | 1976-06-08 |
| JPS5175065A (enrdf_load_stackoverflow) | 1976-06-29 |
| NL7514284A (nl) | 1976-06-09 |
| DK551275A (da) | 1976-06-07 |
| DK144473B (da) | 1982-03-15 |
| DE2554863C2 (de) | 1984-08-23 |
| AU8727575A (en) | 1977-06-09 |
| CA1060024A (en) | 1979-08-07 |
| CH624109A5 (en) | 1981-07-15 |
| SE430064B (sv) | 1983-10-17 |
| GB1476594A (en) | 1977-06-16 |
| AU502387B2 (en) | 1979-07-26 |
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