NO761051L - - Google Patents
Info
- Publication number
- NO761051L NO761051L NO761051A NO761051A NO761051L NO 761051 L NO761051 L NO 761051L NO 761051 A NO761051 A NO 761051A NO 761051 A NO761051 A NO 761051A NO 761051 L NO761051 L NO 761051L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- group
- och2
- alkyl
- Prior art date
Links
- -1 Heterocyclic thiols Chemical class 0.000 claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000007363 ring formation reaction Methods 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 150000003385 sodium Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000007787 solid Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000003573 thiols Chemical class 0.000 description 11
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- IMFQYAJJXFXVMM-UHFFFAOYSA-N 1-(isothiocyanatomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CN=C=S)C=C1 IMFQYAJJXFXVMM-UHFFFAOYSA-N 0.000 description 4
- 229930186147 Cephalosporin Natural products 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229940124587 cephalosporin Drugs 0.000 description 4
- 150000001780 cephalosporins Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- CWTLXFGKFOFEEM-UHFFFAOYSA-N ethyl 2-(2-hydrazinyl-2-oxoethoxy)acetate Chemical compound CCOC(=O)COCC(=O)NN CWTLXFGKFOFEEM-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZOKDAUVPWRRYTO-UHFFFAOYSA-N 5-sulfanylidene-1,2-dihydro-1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C1=NNC(S)=N1 ZOKDAUVPWRRYTO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 3
- JOXPXAYLOMSYOM-UHFFFAOYSA-N ethyl 2-[[4-[(4-methoxyphenyl)methyl]-5-sulfanylidene-1h-1,2,4-triazol-3-yl]methoxy]acetate Chemical compound CCOC(=O)COCC1=NN=C(S)N1CC1=CC=C(OC)C=C1 JOXPXAYLOMSYOM-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical class C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 2
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 2
- RYIZLYKSXIYIGD-UHFFFAOYSA-N 2-[(2-sulfanylidene-3h-1,3,4-oxadiazol-5-yl)methoxy]acetic acid Chemical compound OC(=O)COCC1=NN=C(S)O1 RYIZLYKSXIYIGD-UHFFFAOYSA-N 0.000 description 2
- IZLCVUQGSAOQKB-UHFFFAOYSA-N 2-[(4-methyl-5-sulfanylidene-1h-1,2,4-triazol-3-yl)methoxy]acetic acid Chemical compound CN1C(S)=NN=C1COCC(O)=O IZLCVUQGSAOQKB-UHFFFAOYSA-N 0.000 description 2
- SWOHBHAPPVSCRE-UHFFFAOYSA-N 2-[2-[(4-methoxyphenyl)methylcarbamothioyl]hydrazinyl]-2-oxoacetamide Chemical compound COC1=CC=C(CNC(=S)NNC(=O)C(N)=O)C=C1 SWOHBHAPPVSCRE-UHFFFAOYSA-N 0.000 description 2
- MNSOWCHYOCRELZ-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-5-sulfanylidene-1h-1,2,4-triazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1C(C(N)=O)=NN=C1S MNSOWCHYOCRELZ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- ZRWPZNCDOWPLSD-UHFFFAOYSA-N ethyl 2-[(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)methoxy]acetate Chemical compound CCOC(=O)COCC1=NN=C(S)S1 ZRWPZNCDOWPLSD-UHFFFAOYSA-N 0.000 description 2
- ZRBZFXXOOHPYNW-UHFFFAOYSA-N ethyl 4-[(4-methoxyphenyl)methyl]-5-sulfanylidene-1h-1,2,4-triazole-3-carboxylate Chemical compound CCOC(=O)C1=NN=C(S)N1CC1=CC=C(OC)C=C1 ZRBZFXXOOHPYNW-UHFFFAOYSA-N 0.000 description 2
- OQRHQFHWICEARB-UHFFFAOYSA-N ethyl 5-sulfanylidene-1,2-dihydro-1,2,4-triazole-3-carboxylate Chemical compound CCOC(=O)C1=NNC(S)=N1 OQRHQFHWICEARB-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000523 sample Substances 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
- 238000001665 trituration Methods 0.000 description 2
- RJYHJXVBSQAYNL-UHFFFAOYSA-N 1-amino-3-[(4-methoxyphenyl)methyl]thiourea Chemical compound COC1=CC=C(CNC(=S)NN)C=C1 RJYHJXVBSQAYNL-UHFFFAOYSA-N 0.000 description 1
- AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical class SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 1
- SKGOLFLNFZLJCM-UHFFFAOYSA-N 2-[(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)methoxy]acetamide Chemical compound NC(=O)COCC1=NN=C(S)S1 SKGOLFLNFZLJCM-UHFFFAOYSA-N 0.000 description 1
- MPYFQXKBNRPRAO-UHFFFAOYSA-N 2-[(2-sulfanylidene-3h-1,3,4-thiadiazol-5-yl)methoxy]acetic acid Chemical compound OC(=O)COCC1=NN=C(S)S1 MPYFQXKBNRPRAO-UHFFFAOYSA-N 0.000 description 1
- RQPDRHMSZDFXKS-UHFFFAOYSA-N 2-[(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)methoxy]acetamide Chemical compound NC(=O)COCC1=NNC(S)=N1 RQPDRHMSZDFXKS-UHFFFAOYSA-N 0.000 description 1
- YSKVPZRTMMEEAV-UHFFFAOYSA-N 2-[(5-sulfanylidene-1,2-dihydro-1,2,4-triazol-3-yl)methoxy]acetic acid Chemical compound OC(=O)COCC1=NNC(S)=N1 YSKVPZRTMMEEAV-UHFFFAOYSA-N 0.000 description 1
- UXWAJSLYHVAVKJ-UHFFFAOYSA-N 2-hydrazinyl-2-oxoacetic acid Chemical compound NNC(=O)C(O)=O UXWAJSLYHVAVKJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- MDKCFLQDBWCQCV-UHFFFAOYSA-N Benzyl isothiocyanate Natural products S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- UMENZHCJCJSEBL-UHFFFAOYSA-N ethyl 2-[(2-sulfanylidene-3h-1,3,4-oxadiazol-5-yl)methoxy]acetate Chemical compound CCOC(=O)COCC1=NN=C(S)O1 UMENZHCJCJSEBL-UHFFFAOYSA-N 0.000 description 1
- RZMZBHSKPLVQCP-UHFFFAOYSA-N ethyl 2-amino-2-oxoacetate Chemical compound CCOC(=O)C(N)=O RZMZBHSKPLVQCP-UHFFFAOYSA-N 0.000 description 1
- NEKIIXYWGLWRFP-UHFFFAOYSA-N ethyl 2-sulfanylidene-3h-1,3,4-oxadiazole-5-carboxylate Chemical compound CCOC(=O)C1=NN=C(S)O1 NEKIIXYWGLWRFP-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- MCHNEPJTAILKTN-UHFFFAOYSA-N n-methyl-2-sulfanylidene-3h-1,3,4-thiadiazole-5-carboxamide Chemical compound CNC(=O)C1=NN=C(S)S1 MCHNEPJTAILKTN-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- ARRCHHPJGIKARH-UHFFFAOYSA-M potassium;n-[[2-(2-ethoxy-2-oxoethoxy)acetyl]amino]carbamodithioate Chemical compound [K+].CCOC(=O)COCC(=O)NNC([S-])=S ARRCHHPJGIKARH-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/36—Methylene radicals, substituted by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7512813A GB1542397A (en) | 1975-03-27 | 1975-03-27 | Cephem compounds |
| GB4044775 | 1975-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO761051L true NO761051L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-28 |
Family
ID=26249283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO761051A NO761051L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-03-27 | 1976-03-25 |
Country Status (12)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2853196A1 (de) * | 1978-12-07 | 1980-06-26 | Schering Ag | 1,3,4-thiadiazol-2-carbonsaeure-derivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende fungizide und nematizide mittel |
| US4230715A (en) * | 1979-09-04 | 1980-10-28 | Richardson-Merrell Inc. | 1,2,4-Triazole-3-thiols as antisecretory agents |
-
1976
- 1976-03-11 IL IL49200A patent/IL49200A0/xx unknown
- 1976-03-25 DE DE19762612761 patent/DE2612761A1/de active Pending
- 1976-03-25 LU LU74644A patent/LU74644A1/xx unknown
- 1976-03-25 DK DK132776A patent/DK132776A/da unknown
- 1976-03-25 PT PT64946A patent/PT64946B/pt unknown
- 1976-03-25 NO NO761051A patent/NO761051L/no unknown
- 1976-03-25 FI FI760794A patent/FI760794A7/fi not_active Application Discontinuation
- 1976-03-26 SE SE7603700A patent/SE7603700L/xx unknown
- 1976-03-26 FR FR7608976A patent/FR2305435A1/fr active Granted
- 1976-03-26 DD DD192070A patent/DD124732A5/xx unknown
- 1976-03-26 JP JP51033473A patent/JPS51146467A/ja active Pending
- 1976-03-29 AU AU12443/76A patent/AU1244376A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD124732A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-03-09 |
| FR2305435A1 (fr) | 1976-10-22 |
| DK132776A (da) | 1976-09-28 |
| PT64946A (en) | 1976-04-01 |
| SE7603700L (sv) | 1976-09-28 |
| JPS51146467A (en) | 1976-12-16 |
| LU74644A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-10-10 |
| AU1244376A (en) | 1977-10-06 |
| PT64946B (en) | 1977-08-25 |
| DE2612761A1 (de) | 1976-10-07 |
| IL49200A0 (en) | 1976-05-31 |
| FR2305435B3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-12-22 |
| FI760794A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-28 |
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