JPH0240677B2 - - Google Patents
Info
- Publication number
- JPH0240677B2 JPH0240677B2 JP54172547A JP17254779A JPH0240677B2 JP H0240677 B2 JPH0240677 B2 JP H0240677B2 JP 54172547 A JP54172547 A JP 54172547A JP 17254779 A JP17254779 A JP 17254779A JP H0240677 B2 JPH0240677 B2 JP H0240677B2
- Authority
- JP
- Japan
- Prior art keywords
- amino
- lower alkyl
- nujiyor
- carboxylic acid
- acetamide
- 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 - Lifetime
Links
- -1 cyano, carboxy Chemical group 0.000 claims description 241
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 103
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005333 aroyloxy group Chemical group 0.000 claims 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000004193 piperazinyl group Chemical class 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001166 thiolanyl group Chemical group 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 781
- 238000000354 decomposition reaction Methods 0.000 description 463
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 255
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 196
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 175
- 239000000243 solution Substances 0.000 description 175
- 239000000203 mixture Substances 0.000 description 156
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 137
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 125
- 239000002253 acid Substances 0.000 description 119
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 107
- 238000004519 manufacturing process Methods 0.000 description 89
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 64
- 229960000583 acetic acid Drugs 0.000 description 63
- 239000000843 powder Substances 0.000 description 61
- 238000003756 stirring Methods 0.000 description 56
- 239000010410 layer Substances 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 238000000034 method Methods 0.000 description 47
- 239000007788 liquid Substances 0.000 description 46
- 239000011541 reaction mixture Substances 0.000 description 46
- 239000002244 precipitate Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 37
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 239000007864 aqueous solution Substances 0.000 description 35
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
- 235000019341 magnesium sulphate Nutrition 0.000 description 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 34
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 33
- 239000000284 extract Substances 0.000 description 33
- JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 33
- 235000017557 sodium bicarbonate Nutrition 0.000 description 32
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
- 238000005406 washing Methods 0.000 description 29
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 27
- 239000005973 Carvone Substances 0.000 description 26
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 25
- 239000012141 concentrate Substances 0.000 description 25
- 150000002148 esters Chemical group 0.000 description 25
- 230000002829 reductive effect Effects 0.000 description 24
- 238000001035 drying Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 229940001158 ximino Drugs 0.000 description 20
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 18
- 241001024304 Mino Species 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 18
- FZDRVLJSDYQRPO-HWZXHQHMSA-N (6r)-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CC(C)S[C@@H]2CC(=O)N21 FZDRVLJSDYQRPO-HWZXHQHMSA-N 0.000 description 17
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 description 17
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 17
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 16
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 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 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 11
- 229940047583 cetamide Drugs 0.000 description 11
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 10
- 239000006187 pill Substances 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 239000012043 crude product Substances 0.000 description 7
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- DSHWMBCJDOGPTB-UHFFFAOYSA-N ethyl 2-ethoxy-2-iminoacetate Chemical compound CCOC(=N)C(=O)OCC DSHWMBCJDOGPTB-UHFFFAOYSA-N 0.000 description 5
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 4
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 4
- 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 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 229910052776 Thorium Inorganic materials 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- YEEYUHHXFJYOLG-XCGJVMPOSA-N (6R)-8-oxo-4-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1C(=NN=C1)SCC1S[C@H]2N(C(=C1)C(=O)O)C(C2)=O YEEYUHHXFJYOLG-XCGJVMPOSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- MGOALIGCJKNQBC-UHFFFAOYSA-N 1,3,4-thiadiazol-2-ylmethanamine Chemical compound NCC1=NN=CS1 MGOALIGCJKNQBC-UHFFFAOYSA-N 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 3
- NHENVHGVMLDVPP-UHFFFAOYSA-N 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-cyclopentyloxyiminoacetic acid Chemical compound S1C(N)=NC(C(=NOC2CCCC2)C(O)=O)=N1 NHENVHGVMLDVPP-UHFFFAOYSA-N 0.000 description 3
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 3
- KXEAZJHCOWBLLF-UHFFFAOYSA-N 3-methyl-3-(3-methylpentan-3-yloxy)pentane Chemical compound CCC(C)(CC)OC(C)(CC)CC KXEAZJHCOWBLLF-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- LYAVXWPXKIFHBU-UHFFFAOYSA-N N-{2-[(1,2-diphenylhydrazinyl)carbonyl]-2-hydroxyhexanoyl}-6-aminohexanoic acid Chemical group C=1C=CC=CC=1N(C(=O)C(O)(C(=O)NCCCCCC(O)=O)CCCC)NC1=CC=CC=C1 LYAVXWPXKIFHBU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 244000000010 microbial pathogen Species 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- FMJIREFIIGRAAJ-UHFFFAOYSA-N o-(1-phenylethyl)hydroxylamine Chemical compound NOC(C)C1=CC=CC=C1 FMJIREFIIGRAAJ-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 229940116357 potassium thiocyanate Drugs 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000013076 target substance Substances 0.000 description 3
- SUNJKJWWNNMWSL-UHFFFAOYSA-N tert-butyl 2-aminooxy-3-methylbutanoate Chemical compound CC(C)C(ON)C(=O)OC(C)(C)C SUNJKJWWNNMWSL-UHFFFAOYSA-N 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 description 2
- AYTOSMACNLSHJY-UHFFFAOYSA-N 2-(2-oxooxolan-3-yl)oxyisoindole-1,3-dione Chemical compound O=C1OCCC1ON1C(=O)C2=CC=CC=C2C1=O AYTOSMACNLSHJY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- OPZZNSQTJKVPBZ-UHFFFAOYSA-N 2-cycloheptyloxyisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1OC1CCCCCC1 OPZZNSQTJKVPBZ-UHFFFAOYSA-N 0.000 description 2
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- 229940050176 methyl chloride Drugs 0.000 description 1
- ZLTVQCSUKXAWII-UHFFFAOYSA-N methyl n-propylcarbamodithioate Chemical compound CCCNC(=S)SC ZLTVQCSUKXAWII-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GLMUAFMGXXHGLU-VQAITOIOSA-N minocycline hydrochloride Chemical group [H+].[Cl-].C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O GLMUAFMGXXHGLU-VQAITOIOSA-N 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- YFZBPSXRYCOKCW-UHFFFAOYSA-N n-(3-aminopropyl)acetamide Chemical compound CC(=O)NCCCN YFZBPSXRYCOKCW-UHFFFAOYSA-N 0.000 description 1
- MWUHDYZUBFAXJN-UHFFFAOYSA-N n-[3-(5-sulfanylidene-2h-tetrazol-1-yl)propyl]acetamide Chemical compound CC(=O)NCCCN1N=NN=C1S MWUHDYZUBFAXJN-UHFFFAOYSA-N 0.000 description 1
- RPXRJKHNFVWZDU-UHFFFAOYSA-N n-[6-(5-sulfanylidene-2h-tetrazol-1-yl)hexyl]acetamide Chemical compound CC(=O)NCCCCCCN1N=NN=C1S RPXRJKHNFVWZDU-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- PXSBDHZKKYFWAO-UHFFFAOYSA-N o-(3-aminopropyl)hydroxylamine;dihydrochloride Chemical compound Cl.Cl.NCCCON PXSBDHZKKYFWAO-UHFFFAOYSA-N 0.000 description 1
- PXRMSCGNMHFTDO-UHFFFAOYSA-N o-cyclopent-2-en-1-ylhydroxylamine Chemical compound NOC1CCC=C1 PXRMSCGNMHFTDO-UHFFFAOYSA-N 0.000 description 1
- HWWCBAWGNJYHPP-UHFFFAOYSA-N o-cyclopentylhydroxylamine Chemical compound NOC1CCCC1 HWWCBAWGNJYHPP-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- GWQWBFBJCRDINE-UHFFFAOYSA-M sodium;carbamodithioate Chemical compound [Na+].NC([S-])=S GWQWBFBJCRDINE-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- MITYJMQACATQLP-UHFFFAOYSA-N tert-butyl 2-(1,3-dioxoisoindol-2-yl)oxy-2-methylpropanoate Chemical compound C1=CC=C2C(=O)N(OC(C)(C)C(=O)OC(C)(C)C)C(=O)C2=C1 MITYJMQACATQLP-UHFFFAOYSA-N 0.000 description 1
- JSUWPTFAHGCIFF-UHFFFAOYSA-N tert-butyl 2-(1,3-dioxoisoindol-2-yl)oxy-3-methylbutanoate Chemical compound C1=CC=C2C(=O)N(OC(C(C)C)C(=O)OC(C)(C)C)C(=O)C2=C1 JSUWPTFAHGCIFF-UHFFFAOYSA-N 0.000 description 1
- QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- QYSKPGZETKQLOT-UHFFFAOYSA-N tert-butyl n-[2-(5-sulfanylidene-2h-tetrazol-1-yl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCN1N=NN=C1S QYSKPGZETKQLOT-UHFFFAOYSA-N 0.000 description 1
- NDEXIGADWLWQQT-UHFFFAOYSA-N tert-butyl n-[3-(5-sulfanylidene-2h-tetrazol-1-yl)propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCN1N=NN=C1S NDEXIGADWLWQQT-UHFFFAOYSA-N 0.000 description 1
- NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7850334 | 1978-12-29 | ||
| AU23283/84A AU2328384A (en) | 1978-12-29 | 1984-01-13 | 1,2,4-thiadiazole derivatives |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2005450A Division JPH02223572A (ja) | 1978-12-19 | 1990-01-12 | チアジアゾール酢酸誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55105689A JPS55105689A (en) | 1980-08-13 |
| JPH0240677B2 true JPH0240677B2 (fr) | 1990-09-12 |
Family
ID=32962948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17254779A Granted JPS55105689A (en) | 1978-12-29 | 1979-12-28 | Novel cephem and cepham compounds, their preparation and preventive and remedy for microbism |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS55105689A (fr) |
| HU (1) | HU183006B (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016052439A1 (fr) * | 2014-10-02 | 2016-04-07 | 富士フイルム株式会社 | Procédé de production de 1,2,4-thiadiazole à substitution 5-amino -3 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA813787B (en) * | 1980-06-18 | 1982-07-28 | Fujisawa Pharmaceutical Co | New cephem compounds and processes for preparation thereof |
| US4416879A (en) * | 1980-09-08 | 1983-11-22 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| ZA816321B (en) * | 1980-09-12 | 1982-09-29 | Ciba Geigy | Ammoniomethyl compounds,processes for their manufacture,pharmaceutical preparations that contain these compounds,and the use of these compounds |
| GB2094794B (en) * | 1981-03-06 | 1985-02-20 | Fujisawa Pharmaceutical Co | Processes for preparing 2-substituted hydroxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetic acid or its salt and intermediates thereof |
| JPS584789A (ja) * | 1981-04-03 | 1983-01-11 | Fujisawa Pharmaceut Co Ltd | 新規セフエム化合物およびその製造法 |
| DE3279470D1 (en) * | 1981-04-03 | 1989-04-06 | Fujisawa Pharmaceutical Co | New cephem compounds, processes for their preparation, pharmaceutical compositions containing them and their starting compounds |
| ZA823722B (en) * | 1981-06-22 | 1983-03-30 | Fujisawa Pharmaceutical Co | New cephem compounds and processes for preparation thereof |
| JPS5841887A (ja) * | 1981-08-19 | 1983-03-11 | Fujisawa Pharmaceut Co Ltd | 新規セフエム化合物およびその製造法、並びに細菌感染症予防・治療剤 |
| JPS5859992A (ja) * | 1981-09-14 | 1983-04-09 | Fujisawa Pharmaceut Co Ltd | 新規セフエム化合物およびその製造法、並びに細菌感染症予防・治療剤 |
| US4521413A (en) * | 1981-09-14 | 1985-06-04 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| JPS5888386A (ja) * | 1981-10-22 | 1983-05-26 | Fujisawa Pharmaceut Co Ltd | セフエム化合物およびその製造法 |
| JPS58126877A (ja) * | 1982-01-05 | 1983-07-28 | Fujisawa Pharmaceut Co Ltd | 酢酸誘導体 |
| US4499088A (en) * | 1983-01-04 | 1985-02-12 | Fujisawa Pharmaceutical Co., Ltd. | Cephem compounds |
| DE3300593A1 (de) * | 1983-01-11 | 1984-07-12 | Bayer Ag, 5090 Leverkusen | Neue cephalosporine und verfahren zu ihrer herstellung |
| GB8509087D0 (en) * | 1985-04-09 | 1985-05-15 | Fujisawa Pharmaceutical Co | Cephem compounds |
| JPS62286991A (ja) * | 1986-06-05 | 1987-12-12 | Fujisawa Pharmaceut Co Ltd | セフアロスポラン酸誘導体もしくは医薬として許容されるその塩 |
| JPH085897B2 (ja) * | 1986-11-06 | 1996-01-24 | エーザイ株式会社 | ３−プロペニルセフェム誘導体 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4727991U (fr) * | 1971-04-15 | 1972-11-29 | ||
| JPS484487U (fr) * | 1971-06-15 | 1973-01-19 | ||
| JPS5353691A (en) * | 1976-10-08 | 1978-05-16 | Fujisawa Pharmaceut Co Ltd | 3,7-di-substituted-3-cephem-4 carboxylic acid derivatives, their salts andtheir preparation |
-
1979
- 1979-12-28 JP JP17254779A patent/JPS55105689A/ja active Granted
- 1979-12-28 HU HU79FU382A patent/HU183006B/hu unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4727991U (fr) * | 1971-04-15 | 1972-11-29 | ||
| JPS484487U (fr) * | 1971-06-15 | 1973-01-19 | ||
| JPS5353691A (en) * | 1976-10-08 | 1978-05-16 | Fujisawa Pharmaceut Co Ltd | 3,7-di-substituted-3-cephem-4 carboxylic acid derivatives, their salts andtheir preparation |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016052439A1 (fr) * | 2014-10-02 | 2016-04-07 | 富士フイルム株式会社 | Procédé de production de 1,2,4-thiadiazole à substitution 5-amino -3 |
| JPWO2016052439A1 (ja) * | 2014-10-02 | 2017-06-15 | 富士フイルム株式会社 | ５−アミノ−３置換−１，２，４−チアジアゾールの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55105689A (en) | 1980-08-13 |
| HU183006B (en) | 1984-04-28 |
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