IE43314B1 - 2-acylamino oxazoles - Google Patents
2-acylamino oxazolesInfo
- Publication number
- IE43314B1 IE43314B1 IE1181/76A IE118176A IE43314B1 IE 43314 B1 IE43314 B1 IE 43314B1 IE 1181/76 A IE1181/76 A IE 1181/76A IE 118176 A IE118176 A IE 118176A IE 43314 B1 IE43314 B1 IE 43314B1
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- formula
- methyloxazole
- optionally substituted
- butyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- -1 2-oxazolyl Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 150000003951 lactams Chemical group 0.000 claims description 5
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 abstract description 2
- 238000006073 displacement reaction Methods 0.000 abstract description 2
- 230000000269 nucleophilic effect Effects 0.000 abstract description 2
- 208000001718 Immediate Hypersensitivity Diseases 0.000 abstract 1
- 206010045240 Type I hypersensitivity Diseases 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 208000010216 atopic IgE responsiveness Diseases 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical compound CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 239000004533 oil dispersion Substances 0.000 description 4
- 150000002916 oxazoles Chemical class 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- PUMREIFKTMLCAF-UHFFFAOYSA-N 4-methyl-1,3-oxazole Chemical compound CC1=COC=N1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QCYFOZWGXKXDJA-UHFFFAOYSA-N 1-butoxyhexane Chemical compound CCCCCCOCCCC QCYFOZWGXKXDJA-UHFFFAOYSA-N 0.000 description 2
- XVLXLLHKDRNMGK-UHFFFAOYSA-N 2-methylsulfanyl-1,3-oxazole Chemical compound CSC1=NC=CO1 XVLXLLHKDRNMGK-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- YVORRVFKHZLJGZ-UHFFFAOYSA-N 4,5-Dimethyloxazole Chemical compound CC=1N=COC=1C YVORRVFKHZLJGZ-UHFFFAOYSA-N 0.000 description 2
- ONKNTGBPBLBZFN-UHFFFAOYSA-N 4-methyl-2-methylsulfinyl-1,3-oxazole Chemical compound CC1=COC(S(C)=O)=N1 ONKNTGBPBLBZFN-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-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
- 239000002253 acid Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229940047889 isobutyramide Drugs 0.000 description 2
- GZAROOOHRGKEPC-UHFFFAOYSA-N n-butyl-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)C GZAROOOHRGKEPC-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SONZQXSTWXOYSD-UHFFFAOYSA-N 1-n,2-n-di(propan-2-yl)benzene-1,2-diamine Chemical compound CC(C)NC1=CC=CC=C1NC(C)C SONZQXSTWXOYSD-UHFFFAOYSA-N 0.000 description 1
- XNTVPAJXSZUQQW-UHFFFAOYSA-N 2-benzylsulfonyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(S(=O)(=O)CC=2C=CC=CC=2)=N1 XNTVPAJXSZUQQW-UHFFFAOYSA-N 0.000 description 1
- FIVZZSQNOFRFCO-UHFFFAOYSA-N 2-butylsulfanyl-4-methyl-1,3-oxazole Chemical compound CCCCSC1=NC(C)=CO1 FIVZZSQNOFRFCO-UHFFFAOYSA-N 0.000 description 1
- ZFAIQINIVNSNQE-UHFFFAOYSA-N 2-butylsulfinyl-4-methyl-1,3-oxazole Chemical compound CCCCS(=O)C1=NC(C)=CO1 ZFAIQINIVNSNQE-UHFFFAOYSA-N 0.000 description 1
- DQWFXAYJAOLPDI-UHFFFAOYSA-N 2-cyclohexylsulfinyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(S(=O)C2CCCCC2)=N1 DQWFXAYJAOLPDI-UHFFFAOYSA-N 0.000 description 1
- ZOBZPIGODYBZND-UHFFFAOYSA-N 2-cyclohexylsulfonyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(S(=O)(=O)C2CCCCC2)=N1 ZOBZPIGODYBZND-UHFFFAOYSA-N 0.000 description 1
- WAXRUMDVEFKCBB-UHFFFAOYSA-N 2-ethylsulfinyl-1,3-oxazole Chemical compound CCS(=O)C1=NC=CO1 WAXRUMDVEFKCBB-UHFFFAOYSA-N 0.000 description 1
- RPSNFLPCBRIQKF-UHFFFAOYSA-N 2-ethylsulfonyl-1,3-oxazole Chemical compound CCS(=O)(=O)C1=NC=CO1 RPSNFLPCBRIQKF-UHFFFAOYSA-N 0.000 description 1
- KCOVPCFVNYUBAL-UHFFFAOYSA-N 2-hexylsulfanyl-4-methyl-1,3-oxazole Chemical compound CCCCCCSC1=NC(C)=CO1 KCOVPCFVNYUBAL-UHFFFAOYSA-N 0.000 description 1
- XXFPIXBUCQHCQM-UHFFFAOYSA-N 2-hexylsulfonyl-4-methyl-1,3-oxazole Chemical compound CCCCCCS(=O)(=O)C1=NC(C)=CO1 XXFPIXBUCQHCQM-UHFFFAOYSA-N 0.000 description 1
- WBPNQQLVXYWYLO-UHFFFAOYSA-N 2-iodo-4,5-diphenyl-1,3-oxazole Chemical compound O1C(I)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WBPNQQLVXYWYLO-UHFFFAOYSA-N 0.000 description 1
- LAXDZLSWPAFVGM-UHFFFAOYSA-N 2-methyl-n-(2-methylbutyl)-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCC(C)CN(C(=O)C(C)C)C1=NC(C)=CO1 LAXDZLSWPAFVGM-UHFFFAOYSA-N 0.000 description 1
- MJVLFUAWHYHWOG-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-(3-phenylprop-2-enyl)propanamide Chemical compound N=1C(C)=COC=1N(C(=O)C(C)C)CC=CC1=CC=CC=C1 MJVLFUAWHYHWOG-UHFFFAOYSA-N 0.000 description 1
- YWFJFRRBVSGOPP-UHFFFAOYSA-N 2-methylsulfanyl-4-phenyl-1,3-oxazole Chemical compound O1C(SC)=NC(C=2C=CC=CC=2)=C1 YWFJFRRBVSGOPP-UHFFFAOYSA-N 0.000 description 1
- RNOKFJMXGUXDFP-UHFFFAOYSA-N 2-methylsulfinyl-4-phenyl-1,3-oxazole Chemical compound O1C(S(=O)C)=NC(C=2C=CC=CC=2)=C1 RNOKFJMXGUXDFP-UHFFFAOYSA-N 0.000 description 1
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
- XYLFVYPPRKQXKJ-UHFFFAOYSA-N 4,5-dimethyl-2-methylsulfanyl-1,3-oxazole Chemical compound CSC1=NC(C)=C(C)O1 XYLFVYPPRKQXKJ-UHFFFAOYSA-N 0.000 description 1
- TWAYCFHPZZAERR-UHFFFAOYSA-N 4,5-dimethyl-2-methylsulfonyl-1,3-oxazole Chemical compound CC=1N=C(S(C)(=O)=O)OC=1C TWAYCFHPZZAERR-UHFFFAOYSA-N 0.000 description 1
- XEJIHKUDPINBCS-UHFFFAOYSA-N 4,5-dimethyl-3h-1,3-oxazole-2-thione Chemical compound CC=1N=C(S)OC=1C XEJIHKUDPINBCS-UHFFFAOYSA-N 0.000 description 1
- DQWSTIDSZQGOTD-UHFFFAOYSA-N 4-[(4-methyl-1,3-oxazol-2-yl)-octanoylamino]butanoic acid Chemical compound CCCCCCCC(=O)N(CCCC(O)=O)C1=NC(C)=CO1 DQWSTIDSZQGOTD-UHFFFAOYSA-N 0.000 description 1
- HYZWOWASRQVYMA-UHFFFAOYSA-N 4-ethyl-2-methylsulfanyl-1,3-oxazole Chemical compound CCC1=COC(SC)=N1 HYZWOWASRQVYMA-UHFFFAOYSA-N 0.000 description 1
- UAMJHUYZQHNWRG-UHFFFAOYSA-N 4-ethyl-2-methylsulfonyl-1,3-oxazole Chemical compound CCC1=COC(S(C)(=O)=O)=N1 UAMJHUYZQHNWRG-UHFFFAOYSA-N 0.000 description 1
- FKWZXMKIWPHHMD-UHFFFAOYSA-N 4-methyl-2-methylsulfanyl-1,3-oxazole Chemical compound CSC1=NC(C)=CO1 FKWZXMKIWPHHMD-UHFFFAOYSA-N 0.000 description 1
- YPYPBEGIASEWKA-UHFFFAOYSA-N 5-phenyl-1,3-oxazole Chemical compound O1C=NC=C1C1=CC=CC=C1 YPYPBEGIASEWKA-UHFFFAOYSA-N 0.000 description 1
- 101150059484 CycT gene Proteins 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 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 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000005279 Status Asthmaticus Diseases 0.000 description 1
- 241001061127 Thione Species 0.000 description 1
- ULMUIXVDPKANFT-UHFFFAOYSA-N [2-[acetyl(butyl)amino]-1,3-oxazol-5-yl]methyl acetate Chemical compound CCCCN(C(C)=O)C1=NC=C(COC(C)=O)O1 ULMUIXVDPKANFT-UHFFFAOYSA-N 0.000 description 1
- JBYQQOMWUWAWKG-UHFFFAOYSA-N [2-[butyl(2-methylpropanoyl)amino]-1,3-oxazol-5-yl]methyl 2-methylpropanoate Chemical compound CCCCN(C(=O)C(C)C)C1=NC=C(COC(=O)C(C)C)O1 JBYQQOMWUWAWKG-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000009610 hypersensitivity Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- ICRWBBQXMVAKAK-UHFFFAOYSA-N n,2-dimethyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CC(C)C(=O)N(C)C1=NC(C)=CO1 ICRWBBQXMVAKAK-UHFFFAOYSA-N 0.000 description 1
- YEUHIFQNPUTWQD-UHFFFAOYSA-N n-(4,5-dimethyl-1,3-oxazol-2-yl)-n-ethylpropanamide Chemical compound CCC(=O)N(CC)C1=NC(C)=C(C)O1 YEUHIFQNPUTWQD-UHFFFAOYSA-N 0.000 description 1
- AXRGJUCRANQNHP-UHFFFAOYSA-N n-(4-methyl-1,3-oxazol-2-yl)-n-pentan-3-ylbutanamide Chemical compound CCCC(=O)N(C(CC)CC)C1=NC(C)=CO1 AXRGJUCRANQNHP-UHFFFAOYSA-N 0.000 description 1
- QVSVLFPUYNHTDD-UHFFFAOYSA-N n-(4-methyl-1,3-oxazol-2-yl)-n-pentylbutanamide Chemical compound CCCCCN(C(=O)CCC)C1=NC(C)=CO1 QVSVLFPUYNHTDD-UHFFFAOYSA-N 0.000 description 1
- HWPNQXJPVVSOIU-UHFFFAOYSA-N n-(4-methyl-1,3-oxazol-2-yl)-n-propan-2-ylbutanamide Chemical compound CCCC(=O)N(C(C)C)C1=NC(C)=CO1 HWPNQXJPVVSOIU-UHFFFAOYSA-N 0.000 description 1
- ZAPBGHWMYAZFQE-UHFFFAOYSA-N n-(4-methyl-1,3-oxazol-2-yl)-n-propan-2-ylpropanamide Chemical compound CCC(=O)N(C(C)C)C1=NC(C)=CO1 ZAPBGHWMYAZFQE-UHFFFAOYSA-N 0.000 description 1
- IKZVUXRFRKFFNR-UHFFFAOYSA-N n-benzyl-n-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound CC1=COC(N(CC=2C=CC=CC=2)C(=O)C=2C=CC=CC=2)=N1 IKZVUXRFRKFFNR-UHFFFAOYSA-N 0.000 description 1
- ADJQHEUUNCJTLP-UHFFFAOYSA-N n-benzyl-n-(4-methyl-1,3-oxazol-2-yl)hexanamide Chemical compound N=1C(C)=COC=1N(C(=O)CCCCC)CC1=CC=CC=C1 ADJQHEUUNCJTLP-UHFFFAOYSA-N 0.000 description 1
- GYXSQMOZYFUKNC-UHFFFAOYSA-N n-benzyl-n-(4-methyl-1,3-oxazol-2-yl)pentanamide Chemical compound N=1C(C)=COC=1N(C(=O)CCCC)CC1=CC=CC=C1 GYXSQMOZYFUKNC-UHFFFAOYSA-N 0.000 description 1
- LASKOYXOOOTXQS-UHFFFAOYSA-N n-butan-2-yl-2-methyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCC(C)N(C(=O)C(C)C)C1=NC(C)=CO1 LASKOYXOOOTXQS-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- ODFWZEWZEGZEQA-UHFFFAOYSA-N n-butyl-2-chloro-n-(4-methyl-1,3-oxazol-2-yl)acetamide Chemical compound CCCCN(C(=O)CCl)C1=NC(C)=CO1 ODFWZEWZEGZEQA-UHFFFAOYSA-N 0.000 description 1
- ZRMXRAKRLMCKDG-UHFFFAOYSA-N n-butyl-2-chloro-n-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=CC=C1Cl ZRMXRAKRLMCKDG-UHFFFAOYSA-N 0.000 description 1
- BVHDTEMUMTVCEH-UHFFFAOYSA-N n-butyl-2-cyclopentyl-n-(4-methyl-1,3-oxazol-2-yl)acetamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)CC1CCCC1 BVHDTEMUMTVCEH-UHFFFAOYSA-N 0.000 description 1
- OYSBQIYYPMWEGL-UHFFFAOYSA-N n-butyl-2-methyl-n-(5-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCCCN(C(=O)C(C)C)C1=NC=C(C)O1 OYSBQIYYPMWEGL-UHFFFAOYSA-N 0.000 description 1
- FAJCBZWSTOYELA-UHFFFAOYSA-N n-butyl-3-chloro-n-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=CC(Cl)=C1 FAJCBZWSTOYELA-UHFFFAOYSA-N 0.000 description 1
- SSANQODGNDQNPI-UHFFFAOYSA-N n-butyl-4-fluoro-n-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=C(F)C=C1 SSANQODGNDQNPI-UHFFFAOYSA-N 0.000 description 1
- UQZRONWHHSCCBV-UHFFFAOYSA-N n-butyl-4-methoxy-n-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=C(OC)C=C1 UQZRONWHHSCCBV-UHFFFAOYSA-N 0.000 description 1
- HFMVLLSXUNYXLP-UHFFFAOYSA-N n-butyl-4-methyl-n-(4-methyl-1,3-oxazol-2-yl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=C(C)C=C1 HFMVLLSXUNYXLP-UHFFFAOYSA-N 0.000 description 1
- YBBCMBBSVKFLHN-UHFFFAOYSA-N n-butyl-n-(4,5-dimethyl-1,3-oxazol-2-yl)butanamide Chemical compound CCCCN(C(=O)CCC)C1=NC(C)=C(C)O1 YBBCMBBSVKFLHN-UHFFFAOYSA-N 0.000 description 1
- OTLZJWTWDQVEFG-UHFFFAOYSA-N n-butyl-n-(4,5-dimethyl-1,3-oxazol-2-yl)cyclobutanecarboxamide Chemical compound N=1C(C)=C(C)OC=1N(CCCC)C(=O)C1CCC1 OTLZJWTWDQVEFG-UHFFFAOYSA-N 0.000 description 1
- FTCQJTYMXBTFJS-UHFFFAOYSA-N n-butyl-n-(4-butyl-1,3-oxazol-2-yl)-2-methylpropanamide Chemical compound CCCCN(C(=O)C(C)C)C1=NC(CCCC)=CO1 FTCQJTYMXBTFJS-UHFFFAOYSA-N 0.000 description 1
- KWPMZNUVHZKWIT-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)-3-(trifluoromethyl)benzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=CC(C(F)(F)F)=C1 KWPMZNUVHZKWIT-UHFFFAOYSA-N 0.000 description 1
- GKAWQZKJBLWFEX-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)-3-nitrobenzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=CC([N+]([O-])=O)=C1 GKAWQZKJBLWFEX-UHFFFAOYSA-N 0.000 description 1
- LVUQKRDHEROLMQ-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)adamantane-1-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)N(CCCC)C1=NC(C)=CO1 LVUQKRDHEROLMQ-UHFFFAOYSA-N 0.000 description 1
- SHPIALGSGCJLNJ-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)cyclohexanecarboxamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1CCCCC1 SHPIALGSGCJLNJ-UHFFFAOYSA-N 0.000 description 1
- YSKPHODLBKBYJO-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)cyclopropanecarboxamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1CC1 YSKPHODLBKBYJO-UHFFFAOYSA-N 0.000 description 1
- VMNYHFDYZGOTKR-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)heptanamide Chemical compound CCCCCCC(=O)N(CCCC)C1=NC(C)=CO1 VMNYHFDYZGOTKR-UHFFFAOYSA-N 0.000 description 1
- LYZQNEJEVBPKLU-UHFFFAOYSA-N n-butyl-n-(5-ethyl-1,3-oxazol-2-yl)-2-methylpropanamide Chemical compound CCCCN(C(=O)C(C)C)C1=NC=C(CC)O1 LYZQNEJEVBPKLU-UHFFFAOYSA-N 0.000 description 1
- JCHYFFPHDIJKJX-UHFFFAOYSA-N n-cyclohexyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound N=1C(C)=COC=1N(C(=O)CC)C1CCCCC1 JCHYFFPHDIJKJX-UHFFFAOYSA-N 0.000 description 1
- IYQUXKBPGFQMMX-UHFFFAOYSA-N n-cyclopentyl-n-(4-methyl-1,3-oxazol-2-yl)pentanamide Chemical compound N=1C(C)=COC=1N(C(=O)CCCC)C1CCCC1 IYQUXKBPGFQMMX-UHFFFAOYSA-N 0.000 description 1
- QUHWUFXRYOHUJC-UHFFFAOYSA-N n-ethyl-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCCC(=O)N(CC)C1=NC(C)=CO1 QUHWUFXRYOHUJC-UHFFFAOYSA-N 0.000 description 1
- ANMQRLDTUMSFNB-UHFFFAOYSA-N n-ethyl-n-(4-methyl-1,3-oxazol-2-yl)hexanamide Chemical compound CCCCCC(=O)N(CC)C1=NC(C)=CO1 ANMQRLDTUMSFNB-UHFFFAOYSA-N 0.000 description 1
- GJBHVIXTTFEYRY-UHFFFAOYSA-N n-hexyl-2-methyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCCCCCN(C(=O)C(C)C)C1=NC(C)=CO1 GJBHVIXTTFEYRY-UHFFFAOYSA-N 0.000 description 1
- PTUHRKSMPCEBBS-UHFFFAOYSA-N n-hexyl-n-(4-methyl-1,3-oxazol-2-yl)acetamide Chemical compound CCCCCCN(C(C)=O)C1=NC(C)=CO1 PTUHRKSMPCEBBS-UHFFFAOYSA-N 0.000 description 1
- YEMKVBRHRNHHGE-UHFFFAOYSA-N n-methyl-1-(1-methylpyrrol-2-yl)methanamine Chemical compound CNCC1=CC=CN1C YEMKVBRHRNHHGE-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 1
- 230000008659 phytopathology Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003169 respiratory stimulant agent Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/46—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24552/75A GB1552125A (en) | 1975-06-07 | 1975-06-07 | 2-acylamino oxazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43314L IE43314L (en) | 1976-12-07 |
| IE43314B1 true IE43314B1 (en) | 1981-01-28 |
Family
ID=10213418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1181/76A IE43314B1 (en) | 1975-06-07 | 1976-06-02 | 2-acylamino oxazoles |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS51146462A (en:Method) |
| AR (1) | AR219281A1 (en:Method) |
| AT (1) | AT345278B (en:Method) |
| AU (1) | AU502416B2 (en:Method) |
| BE (1) | BE842580A (en:Method) |
| BG (1) | BG25516A3 (en:Method) |
| CA (1) | CA1080707A (en:Method) |
| CH (1) | CH598236A5 (en:Method) |
| CS (1) | CS190536B2 (en:Method) |
| DD (1) | DD125347A6 (en:Method) |
| DE (1) | DE2625229A1 (en:Method) |
| DK (1) | DK243376A (en:Method) |
| ES (1) | ES448591A1 (en:Method) |
| FR (1) | FR2313372A1 (en:Method) |
| GB (1) | GB1552125A (en:Method) |
| GR (1) | GR60337B (en:Method) |
| HU (1) | HU174777B (en:Method) |
| IE (1) | IE43314B1 (en:Method) |
| IL (1) | IL49710A (en:Method) |
| MX (1) | MX3140E (en:Method) |
| NL (1) | NL7606177A (en:Method) |
| NZ (1) | NZ181026A (en:Method) |
| PH (1) | PH14307A (en:Method) |
| PL (1) | PL100004B1 (en:Method) |
| PT (1) | PT65183B (en:Method) |
| RO (1) | RO69114A (en:Method) |
| SE (1) | SE7606227L (en:Method) |
| SU (1) | SU610490A3 (en:Method) |
| YU (1) | YU136976A (en:Method) |
| ZA (1) | ZA763336B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH655312A5 (de) * | 1982-02-09 | 1986-04-15 | Sandoz Ag | Chloracetamide. |
| PL372332A1 (pl) | 2005-01-19 | 2006-07-24 | ADAMED Sp.z o.o. | Nowe związki, pochodne kwasu 3-fenylopropionowego |
| EP2112149A1 (de) | 2008-04-22 | 2009-10-28 | Bayer CropScience Aktiengesellschaft | 2-[(1h-Pyrazol-4-ylmethyl)-sulfonyl]-Oxazol-Derivate, 2-[(1H-Pyrazol-4-ylmethyl)-sulfanyl]-Oxazol-Derivate und chirale 2-[(1H-Pyrazol-4-ylmethyl)-sulfinyl]-Oxazol-Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| EP2112143A1 (de) | 2008-04-22 | 2009-10-28 | Bayer CropScience AG | 2-(Benzylsulfonyl)-Oxazol-Derivate, chirale 2-(Benzylsulfinyl)-Oxazol-Derivate 2-(Benzylsulfanyl-Oxazol Derivate, Verfahren zu deren Herstellung sowie deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1497536A (en) * | 1973-12-17 | 1978-01-12 | Lilly Industries Ltd | 2-acylaminooxazoles methods for their preparation and their use |
| US3888870A (en) * | 1974-03-08 | 1975-06-10 | Sandoz Ag | 2-sulfinyl-thiazoles and oxazoles |
-
1975
- 1975-06-07 GB GB24552/75A patent/GB1552125A/en not_active Expired
-
1976
- 1976-06-01 GR GR50869A patent/GR60337B/el unknown
- 1976-06-01 CA CA253,867A patent/CA1080707A/en not_active Expired
- 1976-06-01 NZ NZ181026A patent/NZ181026A/xx unknown
- 1976-06-02 SE SE7606227A patent/SE7606227L/xx not_active Application Discontinuation
- 1976-06-02 AR AR263482A patent/AR219281A1/es active
- 1976-06-02 IE IE1181/76A patent/IE43314B1/en unknown
- 1976-06-02 DK DK243376A patent/DK243376A/da not_active Application Discontinuation
- 1976-06-03 IL IL49710A patent/IL49710A/xx unknown
- 1976-06-03 BE BE6045540A patent/BE842580A/xx not_active IP Right Cessation
- 1976-06-03 HU HU76LI295A patent/HU174777B/hu unknown
- 1976-06-03 YU YU01369/76A patent/YU136976A/xx unknown
- 1976-06-03 AU AU14616/76A patent/AU502416B2/en not_active Expired
- 1976-06-03 PT PT65183A patent/PT65183B/pt unknown
- 1976-06-04 DD DD193193A patent/DD125347A6/xx unknown
- 1976-06-04 ZA ZA763336A patent/ZA763336B/xx unknown
- 1976-06-04 AT AT412576A patent/AT345278B/de not_active IP Right Cessation
- 1976-06-04 DE DE19762625229 patent/DE2625229A1/de not_active Withdrawn
- 1976-06-04 PH PH18534A patent/PH14307A/en unknown
- 1976-06-04 JP JP51066028A patent/JPS51146462A/ja active Pending
- 1976-06-04 PL PL1976190128A patent/PL100004B1/pl unknown
- 1976-06-04 ES ES448591A patent/ES448591A1/es not_active Expired
- 1976-06-04 CH CH710576A patent/CH598236A5/xx not_active IP Right Cessation
- 1976-06-04 FR FR7616975A patent/FR2313372A1/fr active Granted
- 1976-06-05 RO RO7686351A patent/RO69114A/ro unknown
- 1976-06-07 CS CS763747A patent/CS190536B2/cs unknown
- 1976-06-07 MX MX000274U patent/MX3140E/es unknown
- 1976-06-07 SU SU762367752A patent/SU610490A3/ru active
- 1976-06-07 BG BG033393A patent/BG25516A3/xx unknown
- 1976-06-08 NL NL7606177A patent/NL7606177A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HU174777B (hu) | 1980-03-28 |
| IE43314L (en) | 1976-12-07 |
| CS190536B2 (en) | 1979-05-31 |
| JPS51146462A (en) | 1976-12-16 |
| BG25516A3 (en) | 1978-10-10 |
| IL49710A0 (en) | 1976-08-31 |
| DD125347A6 (de) | 1977-04-13 |
| CH598236A5 (en:Method) | 1978-04-28 |
| ZA763336B (en) | 1977-05-25 |
| SE7606227L (sv) | 1976-11-08 |
| AU502416B2 (en) | 1979-07-26 |
| PT65183B (en) | 1978-11-06 |
| ATA412576A (de) | 1978-01-15 |
| ES448591A1 (es) | 1977-07-16 |
| YU136976A (en) | 1983-02-28 |
| FR2313372A1 (fr) | 1976-12-31 |
| AU1461676A (en) | 1977-12-08 |
| SU610490A3 (ru) | 1978-06-05 |
| CA1080707A (en) | 1980-07-01 |
| MX3140E (es) | 1980-05-06 |
| AR219281A1 (es) | 1980-08-15 |
| PH14307A (en) | 1981-05-19 |
| FR2313372B1 (en:Method) | 1980-02-15 |
| DK243376A (da) | 1976-12-08 |
| PT65183A (en) | 1976-07-01 |
| PL100004B1 (pl) | 1978-08-31 |
| GR60337B (en) | 1978-05-15 |
| NL7606177A (nl) | 1976-12-09 |
| AT345278B (de) | 1978-09-11 |
| DE2625229A1 (de) | 1976-12-23 |
| RO69114A (ro) | 1980-08-15 |
| BE842580A (fr) | 1976-12-03 |
| NZ181026A (en) | 1978-06-20 |
| GB1552125A (en) | 1979-09-05 |
| IL49710A (en) | 1979-03-12 |
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