CA1261847A - Obtention de produits intermediaires pour la preparation d'acides 4-(isoxazolyl)-thiazole-2- oxamiques et de leurs derives - Google Patents
Obtention de produits intermediaires pour la preparation d'acides 4-(isoxazolyl)-thiazole-2- oxamiques et de leurs derivesInfo
- Publication number
- CA1261847A CA1261847A CA000576255A CA576255A CA1261847A CA 1261847 A CA1261847 A CA 1261847A CA 000576255 A CA000576255 A CA 000576255A CA 576255 A CA576255 A CA 576255A CA 1261847 A CA1261847 A CA 1261847A
- Authority
- CA
- Canada
- Prior art keywords
- thiazole
- isoxazolyl
- delta
- yield
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title description 8
- 239000000543 intermediate Substances 0.000 title description 3
- 150000007513 acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- -1 oxalyloxy Chemical group 0.000 claims abstract description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims abstract 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 238000009795 derivation Methods 0.000 abstract description 2
- SMBKODDGONSFPJ-UHFFFAOYSA-N 3-(1,3-thiazol-4-yl)-1,2-oxazole Chemical compound O1C=CC(C=2N=CSC=2)=N1 SMBKODDGONSFPJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000002804 anti-anaphylactic effect Effects 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 38
- 239000000203 mixture Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 235000019441 ethanol Nutrition 0.000 description 17
- 238000001914 filtration Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 239000004472 Lysine Substances 0.000 description 5
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 235000019766 L-Lysine Nutrition 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 230000000172 allergic effect Effects 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229960000265 cromoglicic acid Drugs 0.000 description 3
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- HWSFCNIVSUSBTQ-UHFFFAOYSA-N 1-(3-chloro-1,2-oxazol-5-yl)ethanone Chemical compound CC(=O)C1=CC(Cl)=NO1 HWSFCNIVSUSBTQ-UHFFFAOYSA-N 0.000 description 2
- MULBTORUXNWBGZ-UHFFFAOYSA-N 1-(3-methoxy-1,2-oxazol-5-yl)ethanone Chemical compound COC=1C=C(C(C)=O)ON=1 MULBTORUXNWBGZ-UHFFFAOYSA-N 0.000 description 2
- MOBMLOWIGFJSCP-UHFFFAOYSA-N 1-(3-methyl-1,2-oxazol-5-yl)ethanone Chemical compound CC(=O)C1=CC(C)=NO1 MOBMLOWIGFJSCP-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- ZIEZUMAWBZSIDK-UHFFFAOYSA-N 2-bromo-1-(3-bromo-1,2-oxazol-5-yl)ethanone Chemical compound BrCC(=O)C1=CC(Br)=NO1 ZIEZUMAWBZSIDK-UHFFFAOYSA-N 0.000 description 2
- YUJSYDOTUCAIFB-UHFFFAOYSA-N 2-bromo-1-(3-chloro-1,2-oxazol-5-yl)ethanone Chemical compound ClC=1C=C(C(=O)CBr)ON=1 YUJSYDOTUCAIFB-UHFFFAOYSA-N 0.000 description 2
- RYEZAVAVYVDROG-UHFFFAOYSA-N 2-bromo-1-(3-methoxy-1,2-oxazol-5-yl)ethanone Chemical compound COC=1C=C(C(=O)CBr)ON=1 RYEZAVAVYVDROG-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- RMKJKEZPEMVMFV-UHFFFAOYSA-N 4-(3-bromo-1,2-oxazol-5-yl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2ON=C(Br)C=2)=C1 RMKJKEZPEMVMFV-UHFFFAOYSA-N 0.000 description 2
- 206010002198 Anaphylactic reaction Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000013566 allergen Substances 0.000 description 2
- 230000036783 anaphylactic response Effects 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000007885 bronchoconstriction Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- NMCSUHDGEHKCQH-UHFFFAOYSA-N 1-(3-bromo-1,2-oxazol-5-yl)ethanone Chemical compound CC(=O)C1=CC(Br)=NO1 NMCSUHDGEHKCQH-UHFFFAOYSA-N 0.000 description 1
- DGXOIXOLVKJYQB-UHFFFAOYSA-N 1-(3-phenylmethoxy-1,2-oxazol-5-yl)ethanone Chemical compound O1C(C(=O)C)=CC(OCC=2C=CC=CC=2)=N1 DGXOIXOLVKJYQB-UHFFFAOYSA-N 0.000 description 1
- ZTLILTJZQBBRJE-UHFFFAOYSA-N 1-[3-(2-chloro-6-fluorophenyl)-1,2-oxazol-5-yl]ethanone Chemical compound O1C(C(=O)C)=CC(C=2C(=CC=CC=2F)Cl)=N1 ZTLILTJZQBBRJE-UHFFFAOYSA-N 0.000 description 1
- QKYGUBNPFHSCNK-UHFFFAOYSA-N 1-[3-(methoxymethyl)-1,2-oxazol-5-yl]ethanol Chemical compound COCC=1C=C(C(C)O)ON=1 QKYGUBNPFHSCNK-UHFFFAOYSA-N 0.000 description 1
- UDPSTGVIDOPGKG-UHFFFAOYSA-N 1-[5-(2-hydroxyethyl)-1,2-oxazol-3-yl]ethanone Chemical compound CC(=O)C=1C=C(CCO)ON=1 UDPSTGVIDOPGKG-UHFFFAOYSA-N 0.000 description 1
- TYSIOSQTKJIFMJ-UHFFFAOYSA-N 1-[5-(hydroxymethyl)-1,2-oxazol-3-yl]ethanone Chemical compound CC(=O)C=1C=C(CO)ON=1 TYSIOSQTKJIFMJ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PQJZHMCWDKOPQG-UHFFFAOYSA-N 2-anilino-2-oxoacetic acid Chemical class OC(=O)C(=O)NC1=CC=CC=C1 PQJZHMCWDKOPQG-UHFFFAOYSA-N 0.000 description 1
- HRRCOIFSSWCOEA-UHFFFAOYSA-N 2-bromo-1-(3-methyl-1,2-oxazol-5-yl)ethanone Chemical compound CC=1C=C(C(=O)CBr)ON=1 HRRCOIFSSWCOEA-UHFFFAOYSA-N 0.000 description 1
- FRFSVXHASPPWPV-UHFFFAOYSA-N 2-bromo-1-(3-phenylmethoxy-1,2-oxazol-5-yl)ethanone Chemical compound O1C(C(=O)CBr)=CC(OCC=2C=CC=CC=2)=N1 FRFSVXHASPPWPV-UHFFFAOYSA-N 0.000 description 1
- PPXHABJTQBEQOV-UHFFFAOYSA-N 2-bromo-1-(5-phenyl-1,2-oxazol-3-yl)ethanone Chemical compound O1N=C(C(=O)CBr)C=C1C1=CC=CC=C1 PPXHABJTQBEQOV-UHFFFAOYSA-N 0.000 description 1
- BXEFOMZQAQWDQR-UHFFFAOYSA-N 2-bromo-1-[3-(2-chloro-6-fluorophenyl)-1,2-oxazol-5-yl]ethanone Chemical compound FC1=CC=CC(Cl)=C1C1=NOC(C(=O)CBr)=C1 BXEFOMZQAQWDQR-UHFFFAOYSA-N 0.000 description 1
- BVRAYSIQWNEOGH-UHFFFAOYSA-N 2-bromo-1-[5-(hydroxymethyl)-1,2-oxazol-3-yl]ethanone Chemical compound OCC1=CC(C(=O)CBr)=NO1 BVRAYSIQWNEOGH-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- TVTWIISHURQUPN-UHFFFAOYSA-N 4-(3-bromo-1,2-oxazol-5-yl)-5-ethyl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2ON=C(Br)C=2)=C1CC TVTWIISHURQUPN-UHFFFAOYSA-N 0.000 description 1
- CJNXYJCFLFFBIG-UHFFFAOYSA-N 4-(3-methoxy-1,2-oxazol-5-yl)-1,3-thiazol-2-amine Chemical compound O1N=C(OC)C=C1C1=CSC(N)=N1 CJNXYJCFLFFBIG-UHFFFAOYSA-N 0.000 description 1
- FQDDGRPOSWOGTD-UHFFFAOYSA-N 4-(3-phenyl-1,2-oxazol-5-yl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2ON=C(C=2)C=2C=CC=CC=2)=C1 FQDDGRPOSWOGTD-UHFFFAOYSA-N 0.000 description 1
- VOWXAMZJYPLGFZ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC=N1 VOWXAMZJYPLGFZ-UHFFFAOYSA-N 0.000 description 1
- KXCQDIWJQBSUJF-UHFFFAOYSA-N 4-phenyl-1,3-thiazole Chemical compound S1C=NC(C=2C=CC=CC=2)=C1 KXCQDIWJQBSUJF-UHFFFAOYSA-N 0.000 description 1
- KMVIBNZRPYTOIZ-UHFFFAOYSA-N 5-(2-amino-1,3-thiazol-4-yl)-1,2-oxazol-3-one;hydrobromide Chemical compound Br.S1C(N)=NC(C=2ON=C(O)C=2)=C1 KMVIBNZRPYTOIZ-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
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- 101800004538 Bradykinin Proteins 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241001239379 Calophysus macropterus Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000576255A CA1261847A (fr) | 1984-07-31 | 1988-08-31 | Obtention de produits intermediaires pour la preparation d'acides 4-(isoxazolyl)-thiazole-2- oxamiques et de leurs derives |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22150A/84 | 1984-07-31 | ||
| IT22150/84A IT1183061B (it) | 1984-07-31 | 1984-07-31 | Composti dotati di attivita'antiallergica |
| CA000487853A CA1246583A (fr) | 1984-07-31 | 1985-07-31 | Acides 4-isoxazolyl)-thiazole-2-oxamiques et leurs derives |
| CA000576255A CA1261847A (fr) | 1984-07-31 | 1988-08-31 | Obtention de produits intermediaires pour la preparation d'acides 4-(isoxazolyl)-thiazole-2- oxamiques et de leurs derives |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000487853A Division CA1246583A (fr) | 1984-07-31 | 1985-07-31 | Acides 4-isoxazolyl)-thiazole-2-oxamiques et leurs derives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1261847A true CA1261847A (fr) | 1989-09-26 |
Family
ID=25670758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000576255A Expired CA1261847A (fr) | 1984-07-31 | 1988-08-31 | Obtention de produits intermediaires pour la preparation d'acides 4-(isoxazolyl)-thiazole-2- oxamiques et de leurs derives |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1261847A (fr) |
-
1988
- 1988-08-31 CA CA000576255A patent/CA1261847A/fr not_active Expired
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