NO772257L - Fremgangsm}te for fremstilling av 2-lavere-alkyl-7-substituert-2- eller -3-cefem-4-karboksylsyrer - Google Patents

Fremgangsm}te for fremstilling av 2-lavere-alkyl-7-substituert-2- eller -3-cefem-4-karboksylsyrer

Info

Publication number: NO772257L
Authority: NO; Norway
Prior art keywords: denotes; compound; methyl; salt; cephem
Prior art date: 1976-06-28

Application number

NO772257A

Other languages

English (en)

Norwegian (no)

Inventor

Takashi Kamiya

Takao Takaya

Tsutomu Teraji

Masashi Hashimoto

Osamu Nakaguti

Teruo Oku

Original Assignee

Fujisawa Pharmaceutical Co

Priority date (The priority date 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 date listed.)

1976-06-28

Filing date

1977-06-27

Publication date

1977-12-29

1976-06-28 Priority claimed from GB26740/76A external-priority patent/GB1580189A/en

1977-06-27 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

1977-12-29 Publication of NO772257L publication Critical patent/NO772257L/no

Links

238000000034 method Methods 0.000 title claims description 62
238000002360 preparation method Methods 0.000 title claims description 8
150000001875 compounds Chemical class 0.000 claims description 139
-1 hydroxymethylene Chemical group 0.000 claims description 87
150000003839 salts Chemical class 0.000 claims description 70
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 54
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 29
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
125000002947 alkylene group Chemical group 0.000 claims description 19
230000002829 reductive effect Effects 0.000 claims description 17
125000003277 amino group Chemical group 0.000 claims description 13
125000006239 protecting group Chemical group 0.000 claims description 13
SFVLFFLHZNRXDS-OULFWDGXSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1S[C@H]2N(C(=C1)C(=O)O)C(C2NC(C(C=1N=C(SC=1)NC=O)=NOC)=O)=O SFVLFFLHZNRXDS-OULFWDGXSA-N 0.000 claims description 10
150000002148 esters Chemical group 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
HBHCUMJUPMFEAN-ANXXIGAQSA-N (6R)-7-[[2-(2-formamido-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1S[C@H]2N(C(=C1)C(=O)O)C(C2NC(C(=O)C=1N=C(SC=1)NC=O)=O)=O HBHCUMJUPMFEAN-ANXXIGAQSA-N 0.000 claims description 7
150000003863 ammonium salts Chemical class 0.000 claims description 6
DNABQAMBZKRDSY-YUMZFPBZSA-N 2,2,2-trichloroethyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC1S[C@H]2N(C(=C1)C(=O)OCC(Cl)(Cl)Cl)C(C2NC(C(C=1NC(SC=1)=N)=NO)=O)=O DNABQAMBZKRDSY-YUMZFPBZSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 4
229940100198 alkylating agent Drugs 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
DPALEWBPIFGMHG-AYMRZMBXSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1S[C@H]2N(C(=C1)C(=O)O)C(C2NC(C(=O)C=1N=C(SC=1)N)=O)=O DPALEWBPIFGMHG-AYMRZMBXSA-N 0.000 claims description 2
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 2
125000000676 alkoxyimino group Chemical group 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 6
125000004442 acylamino group Chemical group 0.000 claims 2
125000005236 alkanoylamino group Chemical group 0.000 claims 2
LZDRVALXJRAHRD-QSHJTWMYSA-N (6r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)C(O)C1=CSC(N)=N1 LZDRVALXJRAHRD-QSHJTWMYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
239000000203 mixture Substances 0.000 description 86
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
238000006243 chemical reaction Methods 0.000 description 64
239000000243 solution Substances 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
238000001816 cooling Methods 0.000 description 38
238000003756 stirring Methods 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
238000002329 infrared spectrum Methods 0.000 description 32
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 32
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
229960001760 dimethyl sulfoxide Drugs 0.000 description 28
238000001914 filtration Methods 0.000 description 26
239000008346 aqueous phase Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 22
239000007858 starting material Substances 0.000 description 22
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
239000000843 powder Substances 0.000 description 17
239000012071 phase Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
238000000354 decomposition reaction Methods 0.000 description 15
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 15
TVKBQHZKABNZCD-YUMZFPBZSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1S[C@H]2N(C(=C1)C(=O)O)C(C2NC(C(C=1NC(SC=1)=N)=NOC)=O)=O TVKBQHZKABNZCD-YUMZFPBZSA-N 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
239000013078 crystal Substances 0.000 description 14
230000009467 reduction Effects 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 12
239000000126 substance Substances 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
238000003379 elimination reaction Methods 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
235000011054 acetic acid Nutrition 0.000 description 10
229910052943 magnesium sulfate Inorganic materials 0.000 description 10
235000019341 magnesium sulphate Nutrition 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000002411 adverse Effects 0.000 description 9
230000007062 hydrolysis Effects 0.000 description 9
238000006460 hydrolysis reaction Methods 0.000 description 9
JPJMIBGVCGNFQD-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CSC(NC=O)=N1 JPJMIBGVCGNFQD-UHFFFAOYSA-N 0.000 description 8
229910052783 alkali metal Inorganic materials 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
RBZWPXDFSWPVNK-XHSFTJEDSA-N (6r)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrochloride Chemical compound Cl.C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)C(O)C1=CSC(N)=N1 RBZWPXDFSWPVNK-XHSFTJEDSA-N 0.000 description 7
125000002252 acyl group Chemical group 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
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 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
BZYSFBJQXKYQOP-OULFWDGXSA-N 2,2,2-trichloroethyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC1S[C@H]2N(C(=C1)C(=O)OCC(Cl)(Cl)Cl)C(C2NC(C(C=1NC(SC=1)=N)=NOC)=O)=O BZYSFBJQXKYQOP-OULFWDGXSA-N 0.000 description 6
MYFSEUCALJPTRN-SISHCKSZSA-N 2,2-dimethylpropanoyloxymethyl (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC1S[C@H]2N(C(=C1)C(=O)OCOC(C(C)(C)C)=O)C(C2NC(C(C=1NC(SC=1)=N)=NOC)=O)=O MYFSEUCALJPTRN-SISHCKSZSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
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 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
230000008030 elimination Effects 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
ILYFQIRZHAPFLB-MBOVBSECSA-N (6r)-7-amino-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2C(N)C(=O)N21 ILYFQIRZHAPFLB-MBOVBSECSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
150000007529 inorganic bases Chemical class 0.000 description 5
LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
HVLMUHVRZBOCAP-KAFAXRABSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1S[C@H]2N(C(=C1)C(=O)O)C(C2NC(C(C=1NC(SC=1)=N)=NO)=O)=O HVLMUHVRZBOCAP-KAFAXRABSA-N 0.000 description 4
NRRJNSWNWIDHOX-UHFFFAOYSA-N 2-(2-formamido-1,3-thiazol-4-yl)-2-methoxyiminoacetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC=O)=N1 NRRJNSWNWIDHOX-UHFFFAOYSA-N 0.000 description 4
MDEKEOFWAHRGNU-UHFFFAOYSA-N 2-methoxyimino-2-[2-[(2,2,2-trifluoroacetyl)amino]-1,3-thiazol-4-yl]acetic acid Chemical compound CON=C(C(O)=O)C1=CSC(NC(=O)C(F)(F)F)=N1 MDEKEOFWAHRGNU-UHFFFAOYSA-N 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
239000011575 calcium Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
POBMBNPEUPDXRS-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOC(=O)C(=NOC)C1=CSC(N)=N1 POBMBNPEUPDXRS-UHFFFAOYSA-N 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
239000011591 potassium Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
OZEATQVFYUCGJC-INTKNLDSSA-N (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-oxoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrochloride Chemical compound Cl.CC1S[C@@H]2C(NC(=O)C(=O)c3csc(N)n3)C(=O)N2C(=C1)C(O)=O OZEATQVFYUCGJC-INTKNLDSSA-N 0.000 description 3
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 3
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 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
230000014509 gene expression Effects 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
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239000005711 Benzoic acid Substances 0.000 description 1
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HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 description 1
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ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
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241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
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AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
235000013832 Valeriana officinalis Nutrition 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008052 alkyl sulfonates Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229960003116 amyl nitrite Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
235000009697 arginine Nutrition 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
239000003245 coal Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
239000012531 culture fluid Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 description 1
WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-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
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
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150000002081 enamines Chemical class 0.000 description 1
239000012374 esterification agent Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
HVJCFGLFQGEABA-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate;hydrobromide Chemical compound Br.CCOC(=O)C(=NOC)C1=CSC(N)=N1 HVJCFGLFQGEABA-UHFFFAOYSA-N 0.000 description 1
LULLGGWIEBUSRX-UHFFFAOYSA-N ethyl 4-bromo-2-methoxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=NOC)C(=O)CBr LULLGGWIEBUSRX-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
239000002038 ethyl acetate fraction Substances 0.000 description 1
WMYNMYVRWWCRPS-UHFFFAOYSA-N ethynoxyethane Chemical group CCOC#C WMYNMYVRWWCRPS-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000005935 hexyloxycarbonyl group Chemical group 0.000 description 1
235000011167 hydrochloric acid Nutrition 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical class [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
150000002540 isothiocyanates Chemical class 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229940071125 manganese acetate Drugs 0.000 description 1
229940082328 manganese acetate tetrahydrate Drugs 0.000 description 1
150000002697 manganese compounds Chemical class 0.000 description 1
UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
CESXSDZNZGSWSP-UHFFFAOYSA-L manganese(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Mn+2].CC([O-])=O.CC([O-])=O CESXSDZNZGSWSP-UHFFFAOYSA-L 0.000 description 1
239000000463 material Substances 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
229940045681 other alkylating agent in atc Drugs 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000007790 scraping Methods 0.000 description 1
RCRNIMXJPPYDOB-BTSNMKAISA-M sodium (6R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC1S[C@H]2N(C(=C1)C(=O)[O-])C(C2NC(C(C=1NC(SC=1)=N)=NOC)=O)=O.[Na+] RCRNIMXJPPYDOB-BTSNMKAISA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
229940087562 sodium acetate trihydrate Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
DXMISFVOLRPPNP-UHFFFAOYSA-M sodium;nitrite;hydrate Chemical compound O.[Na+].[O-]N=O DXMISFVOLRPPNP-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
108010050327 trypticase-soy broth Proteins 0.000 description 1
239000012000 urushibara nickel Substances 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)

NO772257A 1976-06-28 1977-06-27 Fremgangsm}te for fremstilling av 2-lavere-alkyl-7-substituert-2- eller -3-cefem-4-karboksylsyrer NO772257L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB26740/76A GB1580189A (en)	1976-06-28	1976-06-28	Cephalosporin derivatives and the preparation thereof
GB26277		1977-01-05

Publications (1)

Publication Number	Publication Date
NO772257L true NO772257L (no)	1977-12-29

Family

ID=26235798

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO772257A NO772257L (no)	1976-06-28	1977-06-27	Fremgangsm}te for fremstilling av 2-lavere-alkyl-7-substituert-2- eller -3-cefem-4-karboksylsyrer

Country Status (23)

Country	Link
US (1)	US4225707A (es)
JP (1)	JPS5932475B2 (es)
AR (2)	AR218254A1 (es)
AT (1)	AT353963B (es)
AU (1)	AU512804B2 (es)
CA (2)	CA1102307A (es)
CH (3)	CH634074A5 (es)
CS (1)	CS196371B2 (es)
DE (1)	DE2728766A1 (es)
DK (1)	DK284977A (es)
ES (5)	ES460083A1 (es)
FI (1)	FI771866A (es)
FR (1)	FR2356654A1 (es)
GR (1)	GR68939B (es)
HU (1)	HU179181B (es)
IE (1)	IE45222B1 (es)
NL (1)	NL7707150A (es)
NO (1)	NO772257L (es)
NZ (1)	NZ184493A (es)
OA (1)	OA05688A (es)
PT (1)	PT66728B (es)
SE (1)	SE438337B (es)
SU (1)	SU856387A3 (es)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5498795A (en) *	1978-01-13	1979-08-03	Takeda Chem Ind Ltd	Cephalosporin derivative and its preparation
MA18686A1 (fr) *	1978-07-07	1980-10-01	Ciba Geigy Ag	Composes aminothiazoliques
US4305937A (en) *	1978-08-17	1981-12-15	Fujisawa Pharmaceutical Co., Ltd.	2-Lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds and antibacterial pharmaceutical compositions containing them
DE2967053D1 (en) *	1978-09-12	1984-07-19	Fujisawa Pharmaceutical Co	Starting compounds for preparing cephem compounds and processes for their preparation
DE3064106D1 (en) *	1979-06-07	1983-08-18	Yamanouchi Pharma Co Ltd	7-(thiazolylpropionamido) cephalosporins, their preparation, and pharmaceutical compositions containing them
US4443374A (en) *	1982-02-01	1984-04-17	E. R. Squibb & Sons, Inc.	Process for preparing (3S)-3-[[(2-amino-4-thiazolyl)[(1-carboxy-1-methylethoxy)imino]-acetyl]amino]-2-oxo-1-azetidinesulfonic acid, and 4-substituted derivatives
JPS5946287A (ja) *	1982-07-23	1984-03-15	Meiji Seika Kaisha Ltd	新規１−オキサ−１−デチア−セフアロスポリン誘導体
JPS63107977A (ja) *	1986-05-21	1988-05-12	Takeda Chem Ind Ltd	イソオキサゾロン誘導体
JPH09110877A (ja) *	1995-10-17	1997-04-28	Katayama Seiyakushiyo:Kk	セフェム化合物、その製造法及びそれを含有する抗菌剤

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH527215A (de) *	1967-04-15	1972-08-31	Fujisawa Pharmaceutical Co	Verfahren zur Herstellung von 3,7-disubstituierten Cephalosporinderivaten
GB1241656A (en) *	1967-08-21	1971-08-04	Glaxo Lab Ltd	Improvements in or relating to cephalosporin compounds
GB1279402A (en) *	1968-06-14	1972-06-28	Glaxo Lab Ltd	Improvements in or relating to cephalosporin derivatives
US3719672A (en) *	1968-12-11	1973-03-06	Ciba Geigy Corp	4-substituted methylene-7-amino-8-oxo-5-thia-1-aza-bicyclo(4,2,0 oct-2-ene-2-carboxylic acids
GB1445979A (en) *	1972-10-25	1976-08-11	Glaxo Lab Ltd	Cephalosporin derivatives
GB1453049A (en) *	1973-08-21	1976-10-20	Glaxo Lab Ltd	Cephalosporing antibiotics
AR207341A1 (es) *	1973-03-15	1976-09-30	Fujisawa Pharmaceutical Co	Un procedimiento para la preparacion de derivados de acido 2-alquil-2 o 3-cefem-4-carboxilico
JPS5932472B2 (ja) *	1973-03-15	1984-08-09	藤沢薬品工業株式会社	２−アルキル−７−アシルアミノ−２（または３）−セフエム−４−カルボン酸類の製造法
NZ176206A (en) *	1973-12-25	1978-03-06	Takeda Chemical Industries Ltd	Cephalosporins
JPS50111093A (es) *	1974-02-20	1975-09-01
JPS5652908B2 (es) *	1974-07-17	1981-12-15
JPS5512913B2 (es) *	1974-11-13	1980-04-04
JPS5932473B2 (ja) *	1974-02-20	1984-08-09	藤沢薬品工業株式会社	７−アシルアミノ−２（または３）−セフエム−４−カルボン酸類の製造法
US3928333A (en) *	1974-05-20	1975-12-23	Lilly Co Eli	Process for the preparation of 3 cephalosporin esters
GB1480027A (en) *	1974-05-24	1977-07-20	Bristol Myers Co	Cephalosporin derivatives
FR2286138A1 (fr) *	1974-09-27	1976-04-23	Rhone Poulenc Ind	Nouveaux acides oxathiino- et dithiino-aminoacetiques et leur preparation
DK154939C (da) *	1974-12-19	1989-06-12	Takeda Chemical Industries Ltd	Analogifremgangsmaade til fremstilling af thiazolylacetamido-cephemforbindelser eller farmaceutisk acceptable salte eller estere deraf
GB1536281A (en) *	1975-06-09	1978-12-20	Takeda Chemical Industries Ltd	Cephem compounds
JPS5246093A (en) *	1975-10-03	1977-04-12	Fujisawa Pharmaceut Co Ltd	2-alkyl-7-substituted-2, or 3-cephem-4-carboxylic compounds, their sal ts, and preparation thereof

1977
- 1977-06-14 FI FI771866A patent/FI771866A/fi not_active Application Discontinuation
- 1977-06-16 IE IE1234/77A patent/IE45222B1/en unknown
- 1977-06-23 CA CA281,291A patent/CA1102307A/en not_active Expired
- 1977-06-23 AR AR268171A patent/AR218254A1/es active
- 1977-06-23 ES ES460083A patent/ES460083A1/es not_active Expired
- 1977-06-23 CA CA000281290A patent/CA1117104A/en not_active Expired
- 1977-06-24 FR FR7719407A patent/FR2356654A1/fr active Granted
- 1977-06-24 AT AT449177A patent/AT353963B/de not_active IP Right Cessation
- 1977-06-24 OA OA56200A patent/OA05688A/xx unknown
- 1977-06-25 DE DE19772728766 patent/DE2728766A1/de not_active Ceased
- 1977-06-27 SU SU772499562A patent/SU856387A3/ru active
- 1977-06-27 CS CS774218A patent/CS196371B2/cs unknown
- 1977-06-27 DK DK284977A patent/DK284977A/da not_active Application Discontinuation
- 1977-06-27 NZ NZ184493A patent/NZ184493A/xx unknown
- 1977-06-27 PT PT66728A patent/PT66728B/pt unknown
- 1977-06-27 GR GR53813A patent/GR68939B/el unknown
- 1977-06-27 SE SE7707407A patent/SE438337B/xx unknown
- 1977-06-27 NO NO772257A patent/NO772257L/no unknown
- 1977-06-27 CH CH785877A patent/CH634074A5/de not_active IP Right Cessation
- 1977-06-27 JP JP52076817A patent/JPS5932475B2/ja not_active Expired
- 1977-06-28 AU AU26519/77A patent/AU512804B2/en not_active Expired
- 1977-06-28 HU HU77FU355A patent/HU179181B/hu unknown
- 1977-06-28 NL NL7707150A patent/NL7707150A/xx not_active Application Discontinuation
1978
- 1978-06-13 ES ES470756A patent/ES470756A1/es not_active Expired
- 1978-06-13 ES ES470757A patent/ES470757A1/es not_active Expired
- 1978-06-13 ES ES470754A patent/ES470754A1/es not_active Expired
- 1978-06-13 ES ES470755A patent/ES470755A1/es not_active Expired
- 1978-09-25 AR AR273833A patent/AR221601A1/es active
1979
- 1979-02-26 US US06/014,886 patent/US4225707A/en not_active Expired - Lifetime
1983
- 1983-01-13 CH CH18483A patent/CH640538A5/de not_active IP Right Cessation
- 1983-01-13 CH CH18583A patent/CH640539A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
GR68939B (es)	1982-03-29
ES470756A1 (es)	1979-09-01
ES460083A1 (es)	1978-10-01
SE438337B (sv)	1985-04-15
US4225707A (en)	1980-09-30
HU179181B (en)	1982-09-28
NL7707150A (nl)	1977-12-30
PT66728B (en)	1978-11-22
NZ184493A (en)	1980-03-05
FR2356654B1 (es)	1981-06-19
FR2356654A1 (fr)	1978-01-27
AT353963B (de)	1979-12-10
ES470757A1 (es)	1979-02-16
SE7707407L (sv)	1977-12-29
AR221601A1 (es)	1981-02-27
CH640539A5 (de)	1984-01-13
DK284977A (da)	1977-12-29
CH640538A5 (de)	1984-01-13
CA1117104A (en)	1982-01-26
AU2651977A (en)	1979-01-04
JPS5932475B2 (ja)	1984-08-09
AR218254A1 (es)	1980-05-30
IE45222B1 (en)	1982-07-14
CH634074A5 (de)	1983-01-14
IE45222L (en)	1977-12-28
OA05688A (fr)	1981-05-31
PT66728A (en)	1977-07-01
JPS535193A (en)	1978-01-18
CS196371B2 (en)	1980-03-31
ATA449177A (de)	1979-05-15
CA1102307A (en)	1981-06-02
ES470755A1 (es)	1979-09-01
DE2728766A1 (de)	1978-01-05
ES470754A1 (es)	1979-09-01
FI771866A (es)	1977-12-29
SU856387A3 (ru)	1981-08-15
AU512804B2 (en)	1980-10-30

Publication	Publication Date	Title
US4263291A (en)	1981-04-21	3,7-Disubstituted-3-cephem-4-carboxylic acid compounds and processes for the preparation thereof
EP0175610B1 (en)	1990-08-29	New cephalosporin compounds and the production thereof
DE2707565C2 (es)	1988-06-30
JPS6141516B2 (es)	1986-09-16
JPH03135973A (ja)	1991-06-10	アミノチアゾリル酢酸類
EP0001125B1 (en)	1981-11-11	Cephalosporin derivatives, processes for their preparation and pharmaceutical compositions containing them
IE53177B1 (en)	1988-08-17	Cephalosporin derivatives,their preparation and compositions containing them
NO820292L (no)	1982-08-03	Fremgangsmaate for fremstilling av antimikrobielle cefem-derivater
JPS633867B2 (es)	1988-01-26
FR2514004A1 (fr)	1983-04-08	Antibiotiques de dioximino-cephalosporines
EP0008442B1 (en)	1983-02-23	2-lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds, processes for their preparation and pharmaceutical compositions containing them
EP0055466B1 (en)	1987-05-06	Cephem compounds, processes for their preparation, pharmaceutical compositions containing them and their starting compounds
NO772257L (no)	1977-12-29	Fremgangsm}te for fremstilling av 2-lavere-alkyl-7-substituert-2- eller -3-cefem-4-karboksylsyrer
JPH0327552B2 (es)	1991-04-16
US4299829A (en)	1981-11-10	2-Lower alkyl-7-substituted-2 or 3-cephem 4-carboxylic acid compounds
JPS6321677B2 (es)	1988-05-09
JPH01193271A (ja)	1989-08-03	新規セフェム化合物
US4152433A (en)	1979-05-01	2-Lower alkyl-7-substituted-2 or 3-cephem-4-carboxylic acid compounds and pharmaceutical compositions
JPH0144715B2 (es)	1989-09-29
JPH0121154B2 (es)	1989-04-19
HU184805B (en)	1984-10-29	Process for preparing new substituted alkyl-oximes derived from 7-/2-amino-4-thazolyl/-acetamido-cephalosporanic acid
US4191762A (en)	1980-03-04	2-Lower alkyl-7-substituted amino-2 or 3-cephem-4-carboxylic acid compounds
US4371531A (en)	1983-02-01	Cephalosporin compounds
JPH04273877A (ja)	1992-09-30	新規なイミダゾール誘導体
NO760358L (es)	1976-08-05