PL100004B1 - Sposob wytwarzania nowych pochodnych 2-acyloamino-oksazoli - Google Patents
Sposob wytwarzania nowych pochodnych 2-acyloamino-oksazoli Download PDFInfo
- Publication number
- PL100004B1 PL100004B1 PL1976190128A PL19012876A PL100004B1 PL 100004 B1 PL100004 B1 PL 100004B1 PL 1976190128 A PL1976190128 A PL 1976190128A PL 19012876 A PL19012876 A PL 19012876A PL 100004 B1 PL100004 B1 PL 100004B1
- Authority
- PL
- Poland
- Prior art keywords
- methyloxazole
- formula
- butyl
- alkyl
- optionally substituted
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 2-oxazolyl Chemical class 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003951 lactams Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 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
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- PUMREIFKTMLCAF-UHFFFAOYSA-N 4-methyl-1,3-oxazole Chemical compound CC1=COC=N1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 description 34
- 239000000203 mixture Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- YVORRVFKHZLJGZ-UHFFFAOYSA-N 4,5-Dimethyloxazole Chemical compound CC=1N=COC=1C YVORRVFKHZLJGZ-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-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
- 239000012298 atmosphere Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000002971 oxazolyl group Chemical group 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
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QCYFOZWGXKXDJA-UHFFFAOYSA-N 1-butoxyhexane Chemical compound CCCCCCOCCCC QCYFOZWGXKXDJA-UHFFFAOYSA-N 0.000 description 2
- ZFAIQINIVNSNQE-UHFFFAOYSA-N 2-butylsulfinyl-4-methyl-1,3-oxazole Chemical compound CCCCS(=O)C1=NC(C)=CO1 ZFAIQINIVNSNQE-UHFFFAOYSA-N 0.000 description 2
- RQAIEHDXUZPMBJ-UHFFFAOYSA-N 2-chloro-5-phenyl-1,3-oxazole Chemical compound O1C(Cl)=NC=C1C1=CC=CC=C1 RQAIEHDXUZPMBJ-UHFFFAOYSA-N 0.000 description 2
- WAXRUMDVEFKCBB-UHFFFAOYSA-N 2-ethylsulfinyl-1,3-oxazole Chemical compound CCS(=O)C1=NC=CO1 WAXRUMDVEFKCBB-UHFFFAOYSA-N 0.000 description 2
- SCFCQBPUOMKUGV-UHFFFAOYSA-N 2-hexylsulfinyl-4-methyl-1,3-oxazole Chemical compound CCCCCCS(=O)C1=NC(C)=CO1 SCFCQBPUOMKUGV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 201000010099 disease Diseases 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
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000002346 iodo group Chemical group I* 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-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
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 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
- 238000004809 thin layer chromatography Methods 0.000 description 2
- MWDNZMWVENFVHT-UHFFFAOYSA-L (2-decoxy-2-oxoethyl)-[2-[2-[(2-decoxy-2-oxoethyl)-dimethylazaniumyl]ethylsulfanyl]ethyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCOC(=O)C[N+](C)(C)CCSCC[N+](C)(C)CC(=O)OCCCCCCCCCC MWDNZMWVENFVHT-UHFFFAOYSA-L 0.000 description 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 1
- PFJWWVNCWHBPJL-MDZDMXLPSA-N (e)-n-butyl-3-phenylprop-2-enamide Chemical compound CCCCNC(=O)\C=C\C1=CC=CC=C1 PFJWWVNCWHBPJL-MDZDMXLPSA-N 0.000 description 1
- BKHIXCNJVHVHAG-UHFFFAOYSA-N 1,3-oxazol-4-ylmethanol Chemical compound OCC1=COC=N1 BKHIXCNJVHVHAG-UHFFFAOYSA-N 0.000 description 1
- ONXLZGFECOWEGI-UHFFFAOYSA-N 1-(4-methyl-1,3-oxazol-2-yl)azepan-2-one Chemical compound CC1=COC(N2C(CCCCC2)=O)=N1 ONXLZGFECOWEGI-UHFFFAOYSA-N 0.000 description 1
- PSOZJOZKEVZLKZ-UHFFFAOYSA-N 2,4-dimethyloxazole Chemical compound CC1=COC(C)=N1 PSOZJOZKEVZLKZ-UHFFFAOYSA-N 0.000 description 1
- CNNNJMWLGUNYCF-UHFFFAOYSA-N 2-(benzenesulfinyl)-4,5-diphenyl-1,3-oxazole Chemical compound C=1C=CC=CC=1S(=O)C(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 CNNNJMWLGUNYCF-UHFFFAOYSA-N 0.000 description 1
- YTGDJSCRTHJOSE-UHFFFAOYSA-N 2-(benzenesulfonyl)-4,5-diphenyl-1,3-oxazole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(O1)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 YTGDJSCRTHJOSE-UHFFFAOYSA-N 0.000 description 1
- OEANAPSFXQOCFL-UHFFFAOYSA-N 2-benzylsulfinyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(S(=O)CC=2C=CC=CC=2)=N1 OEANAPSFXQOCFL-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
- SWUCSWPQVRMJJQ-UHFFFAOYSA-N 2-butylsulfonyl-4-methyl-1,3-oxazole Chemical compound CCCCS(=O)(=O)C1=NC(C)=CO1 SWUCSWPQVRMJJQ-UHFFFAOYSA-N 0.000 description 1
- SHDAQHZKUROXEE-UHFFFAOYSA-N 2-cyclohexylsulfanyl-4-methyl-1,3-oxazole Chemical compound CC1=COC(SC2CCCCC2)=N1 SHDAQHZKUROXEE-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
- SOAZJBLSEVXTCZ-UHFFFAOYSA-N 2-ethyl-n-(2-methoxyethyl)-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCC(CC)C(=O)N(CCOC)C1=NC(C)=CO1 SOAZJBLSEVXTCZ-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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- PFOHISWVBXEJLZ-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-[(3-methylphenyl)methyl]propanamide Chemical compound N=1C(C)=COC=1N(C(=O)C(C)C)CC1=CC=CC(C)=C1 PFOHISWVBXEJLZ-UHFFFAOYSA-N 0.000 description 1
- WBFPJYGEGCAWKY-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-[(4-methylphenyl)methyl]propanamide Chemical compound N=1C(C)=COC=1N(C(=O)C(C)C)CC1=CC=C(C)C=C1 WBFPJYGEGCAWKY-UHFFFAOYSA-N 0.000 description 1
- KBCICOXIBJQUHH-UHFFFAOYSA-N 2-methyl-n-(4-methyl-1,3-oxazol-2-yl)-n-propan-2-ylpropanamide Chemical compound CC(C)C(=O)N(C(C)C)C1=NC(C)=CO1 KBCICOXIBJQUHH-UHFFFAOYSA-N 0.000 description 1
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- 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
- YRJBZMWQBRBJET-UHFFFAOYSA-N 2-methylsulfonyl-4-phenyl-1,3-oxazole Chemical compound O1C(S(=O)(=O)C)=NC(C=2C=CC=CC=2)=C1 YRJBZMWQBRBJET-UHFFFAOYSA-N 0.000 description 1
- BIMZARKKKXQPQX-UHFFFAOYSA-N 4,5-dimethyl-2-methylsulfinyl-1,3-oxazole Chemical compound CC=1N=C(S(C)=O)OC=1C BIMZARKKKXQPQX-UHFFFAOYSA-N 0.000 description 1
- BVKCIMXCVGFZEN-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,3-oxazole Chemical compound C1=CC(Cl)=CC=C1C1=COC=N1 BVKCIMXCVGFZEN-UHFFFAOYSA-N 0.000 description 1
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- PFYNCRCDKHIWBA-UHFFFAOYSA-N 4-methyl-1,3-oxazol-5-ol Chemical compound CC=1N=COC=1O PFYNCRCDKHIWBA-UHFFFAOYSA-N 0.000 description 1
- ONKNTGBPBLBZFN-UHFFFAOYSA-N 4-methyl-2-methylsulfinyl-1,3-oxazole Chemical compound CC1=COC(S(C)=O)=N1 ONKNTGBPBLBZFN-UHFFFAOYSA-N 0.000 description 1
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 101150047265 COR2 gene Proteins 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 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
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- 208000026935 allergic disease Diseases 0.000 description 1
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- 230000001419 dependent effect Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 235000012489 doughnuts Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 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
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- 238000001802 infusion Methods 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 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
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- 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
- WQGUCTZWZZAMQP-UHFFFAOYSA-N n-(4,5-dimethyl-1,3-oxazol-2-yl)-n-methylacetamide Chemical compound CC(=O)N(C)C1=NC(C)=C(C)O1 WQGUCTZWZZAMQP-UHFFFAOYSA-N 0.000 description 1
- BYQDNEVWAHWCDZ-UHFFFAOYSA-N n-(4-methyl-1,3-oxazol-2-yl)-n-(2-phenylethyl)propanamide Chemical compound N=1C(C)=COC=1N(C(=O)CC)CCC1=CC=CC=C1 BYQDNEVWAHWCDZ-UHFFFAOYSA-N 0.000 description 1
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- YUTQXUCKABCPQQ-UHFFFAOYSA-N n-(4-methyl-1,3-oxazol-2-yl)-n-pentan-3-ylpentanamide Chemical compound CCCCC(=O)N(C(CC)CC)C1=NC(C)=CO1 YUTQXUCKABCPQQ-UHFFFAOYSA-N 0.000 description 1
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- DWEZJOMFVJBKEB-UHFFFAOYSA-N n-(4-methyl-1,3-oxazol-2-yl)-n-propylpentanamide Chemical compound CCCCC(=O)N(CCC)C1=NC(C)=CO1 DWEZJOMFVJBKEB-UHFFFAOYSA-N 0.000 description 1
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- JKAJCRHJPBNTGG-UHFFFAOYSA-N n-benzyl-n-(4-methyl-1,3-oxazol-2-yl)acetamide Chemical compound N=1C(C)=COC=1N(C(=O)C)CC1=CC=CC=C1 JKAJCRHJPBNTGG-UHFFFAOYSA-N 0.000 description 1
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- OJPLOCHZOYBEIG-UHFFFAOYSA-N n-butyl-2-ethyl-n-(4-methyl-1,3-oxazol-2-yl)butanamide Chemical compound CCCCN(C(=O)C(CC)CC)C1=NC(C)=CO1 OJPLOCHZOYBEIG-UHFFFAOYSA-N 0.000 description 1
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- GZAROOOHRGKEPC-UHFFFAOYSA-N n-butyl-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)C GZAROOOHRGKEPC-UHFFFAOYSA-N 0.000 description 1
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- 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
- DVJFUZCNOOPYIS-UHFFFAOYSA-N n-butyl-n-(4,5-dimethyl-1,3-oxazol-2-yl)acetamide Chemical compound CCCCN(C(C)=O)C1=NC(C)=C(C)O1 DVJFUZCNOOPYIS-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
- MOSFDRDCXCUCPR-UHFFFAOYSA-N n-butyl-n-(4-cyclohexyl-1,3-oxazol-2-yl)-2-methylpropanamide Chemical compound O1C(N(C(=O)C(C)C)CCCC)=NC(C2CCCCC2)=C1 MOSFDRDCXCUCPR-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
- BSMLJQAAMZFOMA-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)-3-phenylpropanamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)CCC1=CC=CC=C1 BSMLJQAAMZFOMA-UHFFFAOYSA-N 0.000 description 1
- WLEYNUMIDNFBGK-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)-4-nitrobenzamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1=CC=C([N+]([O-])=O)C=C1 WLEYNUMIDNFBGK-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
- DUZJWTFIQCWMSD-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)cycloheptanecarboxamide Chemical compound N=1C(C)=COC=1N(CCCC)C(=O)C1CCCCCC1 DUZJWTFIQCWMSD-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
- BJHKZNNKWMESRC-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)hexanamide Chemical compound CCCCCC(=O)N(CCCC)C1=NC(C)=CO1 BJHKZNNKWMESRC-UHFFFAOYSA-N 0.000 description 1
- VOXDEQVFCVFBEM-UHFFFAOYSA-N n-butyl-n-(4-methyl-1,3-oxazol-2-yl)pentanamide Chemical compound CCCCC(=O)N(CCCC)C1=NC(C)=CO1 VOXDEQVFCVFBEM-UHFFFAOYSA-N 0.000 description 1
- MIUPVUSAABKKQX-UHFFFAOYSA-N n-cyclohexylbutanamide Chemical compound CCCC(=O)NC1CCCCC1 MIUPVUSAABKKQX-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
- 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
- JQQVBEVWIWFPPZ-UHFFFAOYSA-N n-hexyl-n-(4-methyl-1,3-oxazol-2-yl)propanamide Chemical compound CCCCCCN(C(=O)CC)C1=NC(C)=CO1 JQQVBEVWIWFPPZ-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- OEIZGTXQZLSLFL-UHFFFAOYSA-N n-tert-butyl-2-methylpropanamide Chemical compound CC(C)C(=O)NC(C)(C)C OEIZGTXQZLSLFL-UHFFFAOYSA-N 0.000 description 1
- CABJJNMRUWQXNR-UHFFFAOYSA-N n-tert-butylbutanamide Chemical compound CCCC(=O)NC(C)(C)C CABJJNMRUWQXNR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 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
- 150000002916 oxazoles Chemical class 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
- 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
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000010183 spectrum analysis 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
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 (1)
| Publication Number | Publication Date |
|---|---|
| PL100004B1 true PL100004B1 (pl) | 1978-08-31 |
Family
ID=10213418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1976190128A PL100004B1 (pl) | 1975-06-07 | 1976-06-04 | Sposob wytwarzania nowych pochodnych 2-acyloamino-oksazoli |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS51146462A (forum.php) |
| AR (1) | AR219281A1 (forum.php) |
| AT (1) | AT345278B (forum.php) |
| AU (1) | AU502416B2 (forum.php) |
| BE (1) | BE842580A (forum.php) |
| BG (1) | BG25516A3 (forum.php) |
| CA (1) | CA1080707A (forum.php) |
| CH (1) | CH598236A5 (forum.php) |
| CS (1) | CS190536B2 (forum.php) |
| DD (1) | DD125347A6 (forum.php) |
| DE (1) | DE2625229A1 (forum.php) |
| DK (1) | DK243376A (forum.php) |
| ES (1) | ES448591A1 (forum.php) |
| FR (1) | FR2313372A1 (forum.php) |
| GB (1) | GB1552125A (forum.php) |
| GR (1) | GR60337B (forum.php) |
| HU (1) | HU174777B (forum.php) |
| IE (1) | IE43314B1 (forum.php) |
| IL (1) | IL49710A (forum.php) |
| MX (1) | MX3140E (forum.php) |
| NL (1) | NL7606177A (forum.php) |
| NZ (1) | NZ181026A (forum.php) |
| PH (1) | PH14307A (forum.php) |
| PL (1) | PL100004B1 (forum.php) |
| PT (1) | PT65183B (forum.php) |
| RO (1) | RO69114A (forum.php) |
| SE (1) | SE7606227L (forum.php) |
| SU (1) | SU610490A3 (forum.php) |
| YU (1) | YU136976A (forum.php) |
| ZA (1) | ZA763336B (forum.php) |
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 |
| IE43314B1 (en) | 1981-01-28 |
| 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 (forum.php) | 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 (forum.php) | 1980-02-15 |
| DK243376A (da) | 1976-12-08 |
| PT65183A (en) | 1976-07-01 |
| 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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