KR880001762B1 - 2-치환된 하이드록시이미노-2-(5-아미노-1,2,4-티아디아졸-3-일) 초산 또는 그염의 제조방법 - Google Patents
2-치환된 하이드록시이미노-2-(5-아미노-1,2,4-티아디아졸-3-일) 초산 또는 그염의 제조방법 Download PDFInfo
- Publication number
- KR880001762B1 KR880001762B1 KR8200972A KR820000972A KR880001762B1 KR 880001762 B1 KR880001762 B1 KR 880001762B1 KR 8200972 A KR8200972 A KR 8200972A KR 820000972 A KR820000972 A KR 820000972A KR 880001762 B1 KR880001762 B1 KR 880001762B1
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- thiadiazol
- compound
- salt
- nmr
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- 150000003839 salts Chemical class 0.000 title claims description 49
- 238000000034 method Methods 0.000 title claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- -1 2-substituted hydroxyimino-2- (5-amino-1,2,4-thiadiazol-3-yl) acetic acid Chemical class 0.000 description 69
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 41
- 238000000354 decomposition reaction Methods 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 230000002411 adverse Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 235000011054 acetic acid Nutrition 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- IQDSOHXLWXMDPM-UHFFFAOYSA-N 2-hydroxyiminopropanedinitrile Chemical compound ON=C(C#N)C#N IQDSOHXLWXMDPM-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 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 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- JSHSRYJYYUXPMG-UHFFFAOYSA-N 2-ethoxyiminopropanedinitrile Chemical compound CCON=C(C#N)C#N JSHSRYJYYUXPMG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004356 hydroxy functional group Chemical class O* 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 159000000001 potassium salts Chemical class 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005270 trialkylamine group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- UFTDZEXQFNFPFR-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetic acid Chemical compound CCON=C(C(O)=O)C1=NSC(N)=N1 UFTDZEXQFNFPFR-UHFFFAOYSA-N 0.000 description 2
- DIUMJILQVJWZRI-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-trityloxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C(O)=O)=N1 DIUMJILQVJWZRI-UHFFFAOYSA-N 0.000 description 2
- BHSURVSPWZRSNX-UHFFFAOYSA-N 2-(cyanomethoxyimino)propanedinitrile Chemical compound C(#N)CON=C(C#N)C#N BHSURVSPWZRSNX-UHFFFAOYSA-N 0.000 description 2
- MGOXSPSQGVEAGD-UHFFFAOYSA-N 2-amino-n-ethoxy-2-oxoethanimidoyl cyanide Chemical compound CCON=C(C#N)C(N)=O MGOXSPSQGVEAGD-UHFFFAOYSA-N 0.000 description 2
- BPAUMYWBCYAMGI-UHFFFAOYSA-N 2-methoxyiminopropanedinitrile Chemical compound CON=C(C#N)C#N BPAUMYWBCYAMGI-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- IEFUQGCCWFVCQC-UHFFFAOYSA-N 2-prop-2-ynoxyiminopropanedinitrile Chemical compound C(C#C)ON=C(C#N)C#N IEFUQGCCWFVCQC-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 2
- QUDFYUOLFVZVQB-UHFFFAOYSA-N 5-amino-n-methoxy-1,2,4-thiadiazole-3-carboximidoyl cyanide Chemical compound CON=C(C#N)C1=NSC(N)=N1 QUDFYUOLFVZVQB-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- IWLRJTZAPNDBOW-UHFFFAOYSA-N methyl 2-(dicyanomethylideneamino)oxyacetate Chemical compound COC(=O)CON=C(C#N)C#N IWLRJTZAPNDBOW-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 2
- 229940116357 potassium thiocyanate Drugs 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- VJHTZTZXOKVQRN-UHFFFAOYSA-N 1,2,4-thiadiazol-5-amine Chemical compound NC1=NC=NS1 VJHTZTZXOKVQRN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- AMOYMEBHYUTMKJ-UHFFFAOYSA-N 2-(2-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1CCOCCC1=CC=CC=C1 AMOYMEBHYUTMKJ-UHFFFAOYSA-N 0.000 description 1
- WHOOZVXHOKXKOL-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid Chemical compound NC1=NC(C(=NOCC(F)(F)F)C(O)=O)=NS1 WHOOZVXHOKXKOL-UHFFFAOYSA-N 0.000 description 1
- YFYDGODJLDUKHV-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-methoxy-2-oxoethoxy)iminoacetic acid Chemical compound COC(=O)CON=C(C(O)=O)C1=NSC(N)=N1 YFYDGODJLDUKHV-UHFFFAOYSA-N 0.000 description 1
- YBTSEQZJCNOOKT-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-methylsulfanylethoxyimino)acetic acid Chemical compound CSCCON=C(C(O)=O)C1=NSC(N)=N1 YBTSEQZJCNOOKT-UHFFFAOYSA-N 0.000 description 1
- QUCARRIIFGUXJV-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(2-phenoxyethoxyimino)acetic acid Chemical compound S1C(N)=NC(C(=NOCCOC=2C=CC=CC=2)C(O)=O)=N1 QUCARRIIFGUXJV-UHFFFAOYSA-N 0.000 description 1
- QJNZIFYUIAFUSY-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(3,4-dichlorophenoxy)iminoacetic acid Chemical compound S1C(N)=NC(C(=NOC=2C=C(Cl)C(Cl)=CC=2)C(O)=O)=N1 QJNZIFYUIAFUSY-UHFFFAOYSA-N 0.000 description 1
- XSZNJFMXRLMYIJ-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(4-chlorophenoxy)iminoacetic acid Chemical compound S1C(N)=NC(C(=NOC=2C=CC(Cl)=CC=2)C(O)=O)=N1 XSZNJFMXRLMYIJ-UHFFFAOYSA-N 0.000 description 1
- IYRMJNCXBWNYPM-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(4-fluorophenoxy)iminoacetic acid Chemical compound S1C(N)=NC(C(=NOC=2C=CC(F)=CC=2)C(O)=O)=N1 IYRMJNCXBWNYPM-UHFFFAOYSA-N 0.000 description 1
- MMWUUQAJVKBBGJ-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(carboxymethoxyimino)acetic acid Chemical compound NC1=NC(C(=NOCC(O)=O)C(O)=O)=NS1 MMWUUQAJVKBBGJ-UHFFFAOYSA-N 0.000 description 1
- NALAMTSNXHJMLJ-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methylsulfanylmethoxyimino)acetic acid Chemical compound CSCON=C(C(O)=O)C1=NSC(N)=N1 NALAMTSNXHJMLJ-UHFFFAOYSA-N 0.000 description 1
- LWLFFOQTWSVRLY-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[(4-fluorophenyl)methoxyimino]acetic acid Chemical compound C1=CC(=CC=C1CON=C(C2=NSC(=N2)N)C(=O)O)F LWLFFOQTWSVRLY-UHFFFAOYSA-N 0.000 description 1
- QEOUOAPRUNEJIM-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[2-(2-hexoxyethoxy)ethoxyimino]acetic acid Chemical compound CCCCCCOCCOCCON=C(C(O)=O)C1=NSC(N)=N1 QEOUOAPRUNEJIM-UHFFFAOYSA-N 0.000 description 1
- NGOIWWBDYVUCPX-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-[3-(trifluoromethyl)phenoxy]iminoacetic acid Chemical compound S1C(N)=NC(C(=NOC=2C=C(C=CC=2)C(F)(F)F)C(O)=O)=N1 NGOIWWBDYVUCPX-UHFFFAOYSA-N 0.000 description 1
- RJAMDMFSZYDDKB-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-cycloheptyloxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOC2CCCCCC2)C(O)=O)=N1 RJAMDMFSZYDDKB-UHFFFAOYSA-N 0.000 description 1
- KTDABQPVXDDUPL-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-cyclohex-2-en-1-yloxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOC2C=CCCC2)C(O)=O)=N1 KTDABQPVXDDUPL-UHFFFAOYSA-N 0.000 description 1
- ILMAMFYUYRGJBB-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-cyclopent-2-en-1-yloxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOC2C=CCC2)C(O)=O)=N1 ILMAMFYUYRGJBB-UHFFFAOYSA-N 0.000 description 1
- BXFBVTHMJOEAKN-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hexoxyiminoacetic acid Chemical compound C(CCCCC)ON=C(C(=O)O)C1=NSC(=N1)N BXFBVTHMJOEAKN-UHFFFAOYSA-N 0.000 description 1
- YLFZQLDHKKLIEL-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-phenoxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOC=2C=CC=CC=2)C(O)=O)=N1 YLFZQLDHKKLIEL-UHFFFAOYSA-N 0.000 description 1
- BCGRNMNSZMRBST-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-phenylmethoxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOCC=2C=CC=CC=2)C(O)=O)=N1 BCGRNMNSZMRBST-UHFFFAOYSA-N 0.000 description 1
- OWCDJFBXQPMFIH-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-prop-2-enoxyiminoacetic acid Chemical compound NC1=NC(C(=NOCC=C)C(O)=O)=NS1 OWCDJFBXQPMFIH-UHFFFAOYSA-N 0.000 description 1
- RZPVDLOPOFEDGV-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-prop-2-ynoxyiminoacetic acid Chemical compound NC1=NC(C(=NOCC#C)C(O)=O)=NS1 RZPVDLOPOFEDGV-UHFFFAOYSA-N 0.000 description 1
- VYBMJRMYMPYWGA-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-propan-2-yloxyiminoacetic acid Chemical compound CC(C)ON=C(C(O)=O)C1=NSC(N)=N1 VYBMJRMYMPYWGA-UHFFFAOYSA-N 0.000 description 1
- MTCJAAPIPQZMAM-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-propoxyiminoacetic acid Chemical compound CCCON=C(C(O)=O)C1=NSC(N)=N1 MTCJAAPIPQZMAM-UHFFFAOYSA-N 0.000 description 1
- FVJFUZSJFAXEDW-UHFFFAOYSA-N 2-[[(5-amino-1,2,4-thiadiazol-3-yl)-carboxymethylidene]amino]oxy-4-hydroxybutanoic acid Chemical compound NC1=NC(C(=NOC(CCO)C(O)=O)C(O)=O)=NS1 FVJFUZSJFAXEDW-UHFFFAOYSA-N 0.000 description 1
- GWEAQGZITSJCMK-UHFFFAOYSA-N 2-amino-2-hydroxypropanedinitrile Chemical compound N#CC(O)(N)C#N GWEAQGZITSJCMK-UHFFFAOYSA-N 0.000 description 1
- STSCCZIUHAGRRV-UHFFFAOYSA-N 2-amino-2-imino-N-prop-2-ynoxyethanimidoyl cyanide Chemical compound C(#N)C(C(=N)N)=NOCC#C STSCCZIUHAGRRV-UHFFFAOYSA-N 0.000 description 1
- QXDMLHOUCYDGFV-UHFFFAOYSA-N 2-amino-n-ethoxy-2-iminoethanimidoyl cyanide Chemical compound CCON=C(C#N)C(N)=N QXDMLHOUCYDGFV-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- CAFXGFHPOQBGJP-UHFFFAOYSA-N 2-cyano-2-hydroxyiminoacetamide Chemical compound NC(=O)C(=NO)C#N CAFXGFHPOQBGJP-UHFFFAOYSA-N 0.000 description 1
- ASUXLXLSIPJQQN-UHFFFAOYSA-N 2-methoxypropan-1-imine Chemical compound COC(C)C=N ASUXLXLSIPJQQN-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- NSGUSFGRUOCMNY-UHFFFAOYSA-N 3-[[(5-amino-1,2,4-thiadiazol-3-yl)-carboxymethylidene]amino]oxybenzoic acid Chemical compound S1C(N)=NC(C(=NOC=2C=C(C=CC=2)C(O)=O)C(O)=O)=N1 NSGUSFGRUOCMNY-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- UVHQNMBLIRQRSO-UHFFFAOYSA-N 5-amino-N-(cyanomethoxy)-1,2,4-thiadiazole-3-carboximidoyl cyanide Chemical compound C(#N)CON=C(C#N)C1=NSC(=N1)N UVHQNMBLIRQRSO-UHFFFAOYSA-N 0.000 description 1
- GOFGUFGQNQZMPC-UHFFFAOYSA-N 5-amino-N-prop-2-ynoxy-1,2,4-thiadiazole-3-carboximidoyl cyanide Chemical compound C#CCON=C(C#N)C1=NSC(=N1)N GOFGUFGQNQZMPC-UHFFFAOYSA-N 0.000 description 1
- MMIKKDRJUBPJNK-UHFFFAOYSA-N 5-amino-n-ethoxy-1,2,4-thiadiazole-3-carboximidoyl cyanide Chemical compound CCON=C(C#N)C1=NSC(N)=N1 MMIKKDRJUBPJNK-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 150000004006 C-nitroso compounds Chemical class 0.000 description 1
- 0 CC(*)=NC(C(C(O)=O)=NC)=NC Chemical compound CC(*)=NC(C(C(O)=O)=NC)=NC 0.000 description 1
- PSKUHZPRALIDIH-UHFFFAOYSA-N CC(C(=O)O)C1=NSC(=N1)N=NOC Chemical compound CC(C(=O)O)C1=NSC(=N1)N=NOC PSKUHZPRALIDIH-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 1
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- USLALLIWUFBVAF-UHFFFAOYSA-N methyl 2-(1-cyanoethylideneamino)oxyacetate Chemical compound COC(=O)CON=C(C#N)C USLALLIWUFBVAF-UHFFFAOYSA-N 0.000 description 1
- UVPJAXUZDWHIKF-UHFFFAOYSA-N methyl 2-[[(5-amino-1,2,4-thiadiazol-3-yl)-cyanomethylidene]amino]oxyacetate Chemical compound COC(=O)CON=C(C#N)C1=NSC(N)=N1 UVPJAXUZDWHIKF-UHFFFAOYSA-N 0.000 description 1
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 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
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8107134 | 1981-03-06 | ||
| GB8107134 | 1981-03-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830009067A KR830009067A (ko) | 1983-12-17 |
| KR880001762B1 true KR880001762B1 (ko) | 1988-09-12 |
Family
ID=10520204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8200972A Expired KR880001762B1 (ko) | 1981-03-06 | 1982-03-06 | 2-치환된 하이드록시이미노-2-(5-아미노-1,2,4-티아디아졸-3-일) 초산 또는 그염의 제조방법 |
Country Status (3)
| Country | Link |
|---|---|
| JP (2) | JPS57158769A (enrdf_load_stackoverflow) |
| KR (1) | KR880001762B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2094794B (enrdf_load_stackoverflow) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0717622B2 (ja) * | 1986-06-05 | 1995-03-01 | エーザイ株式会社 | チアジアゾリルアセトアミド誘導体 |
| JPH0625187B2 (ja) * | 1986-12-10 | 1994-04-06 | エーザイ株式会社 | チアジアゾール誘導体 |
| JPH0699449B2 (ja) * | 1988-03-16 | 1994-12-07 | エーザイ株式会社 | セフェム誘導体の合成中間体 |
| JPH03130273A (ja) * | 1989-07-19 | 1991-06-04 | Fujisawa Pharmaceut Co Ltd | ２―置換ヒドロキシイミノ―２―（５―アミノ―１，２，４―チアジアゾール―３―イル）酢酸またはその塩の製造法およびそれらの中間体 |
| JPH09301965A (ja) * | 1996-03-15 | 1997-11-25 | Katayama Seiyakushiyo:Kk | ５−アミノ−１，２，４−チアジアゾール酢酸誘導体の製造方法 |
| CN101962371B (zh) * | 2010-10-13 | 2013-07-24 | 浙江工业大学 | 一种头孢托罗侧链酸及其关键中间体的制备方法 |
| CN102093266B (zh) * | 2011-01-21 | 2013-07-24 | 蚌埠丰原医药科技发展有限公司 | 一种制备o-甲苯磺酰基-2-氨甲酰基-2-甲氧亚氨基乙酰胺肟的方法 |
| CN105377812B (zh) * | 2013-06-21 | 2018-09-18 | 组合化学工业株式会社 | 2-氨基-2-肟基-n-烷氧基亚氨代乙酰基氰化物的制备方法及其制备中间体 |
| CN103804321B (zh) * | 2014-02-18 | 2016-03-02 | 陕西思尔生物科技有限公司 | (Z)-5-氨基-α-(乙氧亚氨基)-1,2,4-噻二唑-3-乙酸的制备方法 |
| CN104177408B (zh) * | 2014-09-12 | 2016-09-07 | 衡水衡林生物科技有限公司 | （z）-2-(5-二氯磷酰氨基-1,2,4-噻二唑-3-基)-2-乙氧亚胺基乙酰氯的制备方法 |
| CN105330612B (zh) * | 2015-11-04 | 2018-04-03 | 上海泰坦科技股份有限公司 | 2‑(5‑氨基‑1,2,4‑噻二唑‑3‑基)‑2‑甲氧亚氨基乙酸的合成工艺 |
| WO2018053587A1 (en) * | 2016-09-21 | 2018-03-29 | Vectus Biosystems Limited | Compositions for the treatment of hypertension and/or fibrosis |
| CN114276291B (zh) | 2018-07-13 | 2023-11-21 | 沈阳中化农药化工研发有限公司 | 制备丙二腈肟醚类化合物的方法及中间体化合物 |
| CN109096224A (zh) * | 2018-09-27 | 2018-12-28 | 陕西思尔生物科技有限公司 | 一种头孢吡普侧链酸的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS576425B2 (enrdf_load_stackoverflow) * | 1972-06-19 | 1982-02-04 | ||
| JPS4924963A (enrdf_load_stackoverflow) * | 1972-06-27 | 1974-03-05 | ||
| JPS5537556B2 (enrdf_load_stackoverflow) * | 1973-12-27 | 1980-09-29 | ||
| HU183006B (en) * | 1978-12-29 | 1984-04-28 | Fujisawa Pharmaceutical Co | Process for producing 7-substituted-3-cepheme- and cephame-4-carboxylic acid derivatives |
-
1982
- 1982-03-01 GB GB8205933A patent/GB2094794B/en not_active Expired
- 1982-03-05 JP JP57035693A patent/JPS57158769A/ja active Granted
- 1982-03-06 KR KR8200972A patent/KR880001762B1/ko not_active Expired
-
1991
- 1991-10-30 JP JP3349290A patent/JPH0629272B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57158769A (en) | 1982-09-30 |
| KR830009067A (ko) | 1983-12-17 |
| JPH0629272B2 (ja) | 1994-04-20 |
| GB2094794A (en) | 1982-09-22 |
| JPH0476990B2 (enrdf_load_stackoverflow) | 1992-12-07 |
| GB2094794B (en) | 1985-02-20 |
| JPH05186447A (ja) | 1993-07-27 |
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