NO761438L - - Google Patents

Info

Publication number: NO761438L
Authority: NO; Norway
Prior art keywords: compound; formula; group; accordance; salt
Prior art date: 1975-04-30

Application number

NO761438A

Other languages

English (en)

Norwegian (no)

Inventor

H Nakao

H Yanagisawa

B Shimizu

M Kaneko

M Nagano

S Sugawara

Original Assignee

Sankyo 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.)

1975-04-30

Filing date

1976-04-27

Publication date

1976-11-02

1975-04-30 Priority claimed from JP5218075A external-priority patent/JPS51128995A/ja

1975-05-07 Priority claimed from JP5502675A external-priority patent/JPS51131889A/ja

1976-04-27 Application filed by Sankyo Co filed Critical Sankyo Co

1976-11-02 Publication of NO761438L publication Critical patent/NO761438L/no

Links

150000001875 compounds Chemical class 0.000 claims description 39
-1 2-carboxyethylthio group Chemical group 0.000 claims description 30
238000000034 method Methods 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 13
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
229910052783 alkali metal Inorganic materials 0.000 claims description 10
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical group CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 9
239000002585 base Substances 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 6
235000017557 sodium bicarbonate Nutrition 0.000 claims description 6
239000000126 substance Substances 0.000 claims description 6
XOHZHMUQBFJTNH-UHFFFAOYSA-N 1-methyl-2h-tetrazole-5-thione Chemical compound CN1N=NN=C1S XOHZHMUQBFJTNH-UHFFFAOYSA-N 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
231100000252 nontoxic Toxicity 0.000 claims description 5
230000003000 nontoxic effect Effects 0.000 claims description 5
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
239000003242 anti bacterial agent Substances 0.000 claims description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
235000015872 dietary supplement Nutrition 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims 2
150000001342 alkaline earth metals Chemical class 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
239000000203 mixture Substances 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 14
239000000243 solution Substances 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 11
239000000284 extract Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
241000894006 Bacteria Species 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001266 acyl halides Chemical class 0.000 description 3
XJMPIWFDBFZCME-UHFFFAOYSA-N benzhydryl 5-chloro-5-sulfanylidenepentanoate Chemical compound C=1C=CC=CC=1C(OC(=O)CCCC(=S)Cl)C1=CC=CC=C1 XJMPIWFDBFZCME-UHFFFAOYSA-N 0.000 description 3
150000001782 cephems Chemical class 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
229910000343 potassium bisulfate Inorganic materials 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical class C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000008055 phosphate buffer solution Substances 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
239000011736 potassium bicarbonate Substances 0.000 description 2
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 1
XUTQHTOXGKVJPN-XCGJVMPOSA-N (6r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)C(N)[C@H]2SC1 XUTQHTOXGKVJPN-XCGJVMPOSA-N 0.000 description 1
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 1
KYZZGAZEWCAIOP-UHFFFAOYSA-N 3,3,3-trifluoropropanethioyl chloride Chemical compound FC(F)(F)CC(Cl)=S KYZZGAZEWCAIOP-UHFFFAOYSA-N 0.000 description 1
DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
QOXKMDIICHDUFG-UHFFFAOYSA-N 5-benzhydryloxy-5-oxopentanethioic s-acid Chemical compound C=1C=CC=CC=1C(OC(=O)CCCC(=S)O)C1=CC=CC=C1 QOXKMDIICHDUFG-UHFFFAOYSA-N 0.000 description 1
229930184397 7-Methoxycephalosporin Natural products 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
GNWUOVJNSFPWDD-XMZRARIVSA-M Cefoxitin sodium Chemical compound [Na+].N([C@]1(OC)C(N2C(=C(COC(N)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)CC1=CC=CS1 GNWUOVJNSFPWDD-XMZRARIVSA-M 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
150000008522 N-ethylpiperidines Chemical class 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
241001354013 Salmonella enterica subsp. enterica serovar Enteritidis Species 0.000 description 1
241000147000 Shigella flexneri 2a Species 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
ICZOIXFFVKYXOM-YCLOEFEOSA-M cefamandole nafate Chemical compound [Na+].CN1N=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@H](OC=O)C=3C=CC=CC=3)[C@H]2SC1 ICZOIXFFVKYXOM-YCLOEFEOSA-M 0.000 description 1
229960002682 cefoxitin Drugs 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
VLCINIKIVYNLPT-UHFFFAOYSA-J dicalcium;hydrogen phosphate Chemical compound [Ca+2].[Ca+2].OP(O)([O-])=O.[O-]P([O-])([O-])=O VLCINIKIVYNLPT-UHFFFAOYSA-J 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical class CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
239000000659 freezing mixture Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Chemical class 0.000 description 1
239000002184 metal Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229960003975 potassium Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
244000144977 poultry Species 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000003826 tablet Substances 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
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
- 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)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO761438A 1975-04-30 1976-04-27 NO761438L (hu)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP5218075A JPS51128995A (en)	1975-04-30	1975-04-30	Process for preparing 7-methoxyceph alosporin derivatives
JP5502675A JPS51131889A (en)	1975-05-07	1975-05-07	A process for preparing 7-methoxycephalosporin derivatives

Publications (1)

Publication Number	Publication Date
NO761438L true NO761438L (hu)	1976-11-02

Family

ID=26392800

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO761438A NO761438L (hu)	1975-04-30	1976-04-27

Country Status (12)

Country	Link
US (1)	US4126745A (hu)
CH (1)	CH624120A5 (hu)
DE (1)	DE2619395A1 (hu)
DK (1)	DK192576A (hu)
FR (1)	FR2309233A1 (hu)
GB (1)	GB1508113A (hu)
HU (1)	HU172532B (hu)
IE (1)	IE43912B1 (hu)
NL (1)	NL7604658A (hu)
NO (1)	NO761438L (hu)
PH (1)	PH12666A (hu)
SE (1)	SE427558B (hu)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2727977C3 (de) *	1977-06-22	1981-11-26	Asahi Kasei Kogyo K.K., Osaka	7α -Methoxycephalosporinderivate und sie enthaltende Arzneimittel
IL58939A (en) *	1978-12-18	1983-03-31	Meiji Seika Kaisha	7 alpha-methoxycephalosporin derivatives and their production
JPS5583791A (en) *	1978-12-18	1980-06-24	Meiji Seika Kaisha Ltd	7-methoxycephalosporin derivative and its preparation

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH557381A (de) *	1967-04-15	1974-12-31	Fujisawa Pharmaceutical Co	Verfahren zur herstellung von (delta)3-cephemverbindungen.
FR2100769B1 (hu) *	1971-06-16	1974-09-27	Merck & Co Inc
US3898221A (en) *	1972-07-20	1975-08-05	Smithkline Corp	Trifluoromethylmercaptoacetamidocephalosporins
US3920639A (en) *	1973-04-23	1975-11-18	Squibb & Sons Inc	Cyanomethylthioacetyl-7-methoxycephalosporins
GB1449420A (en)	1973-11-26	1976-09-15	Sankyo Co	7alpha-methoxycephalosporing derivatives
ZA755266B (en)	1974-09-09	1976-07-28	Smithkline Corp	Novel cephamycins
US4059578A (en) *	1974-09-09	1977-11-22	Smithkline Corporation	7-Substituted mercaptoacetamido cephamycins
US3971779A (en) *	1975-02-07	1976-07-27	American Home Products Corporation	7-[2-(5-Amino-1,3,4-thiadiazol-2-ylthio)acetamido]cephalosporins

1976
- 1976-04-13 US US05/676,488 patent/US4126745A/en not_active Expired - Lifetime
- 1976-04-26 GB GB16768/76A patent/GB1508113A/en not_active Expired
- 1976-04-27 NO NO761438A patent/NO761438L/no unknown
- 1976-04-28 CH CH534576A patent/CH624120A5/de not_active IP Right Cessation
- 1976-04-28 SE SE7604879A patent/SE427558B/xx unknown
- 1976-04-29 NL NL7604658A patent/NL7604658A/xx not_active Application Discontinuation
- 1976-04-29 HU HU76SA00002918A patent/HU172532B/hu unknown
- 1976-04-29 FR FR7612767A patent/FR2309233A1/fr active Granted
- 1976-04-29 DK DK192576A patent/DK192576A/da unknown
- 1976-04-30 PH PH18385A patent/PH12666A/en unknown
- 1976-04-30 IE IE934/76A patent/IE43912B1/en unknown
- 1976-04-30 DE DE19762619395 patent/DE2619395A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
DK192576A (da)	1976-10-31
NL7604658A (nl)	1976-11-02
DE2619395A1 (de)	1976-11-11
IE43912L (en)	1976-10-30
HU172532B (hu)	1978-09-28
US4126745A (en)	1978-11-21
AU1349576A (en)	1977-11-03
SE7604879L (sv)	1976-10-31
SE427558B (sv)	1983-04-18
FR2309233B1 (hu)	1979-01-19
PH12666A (en)	1979-07-11
GB1508113A (en)	1978-04-19
IE43912B1 (en)	1981-07-01
CH624120A5 (hu)	1981-07-15
FR2309233A1 (fr)	1976-11-26

Publication	Publication Date	Title
DE2455884C3 (de)	1981-11-19	7α-Methoxycephalosporinderivate, Verfahren zu ihrer Herstellung und Arzneimittel
JPS6237037B2 (hu)	1987-08-10
NO166228B (no)	1991-03-11	Halogenerte cephalosporinderivater.
US4066762A (en)	1978-01-03	Derivatives of 7-(2-substituted-2-hydroxyiminoacetamido)-3-(1-substituted tetrazol-5-ylthiomethyl-3-cephem-4-carboxylic acid
DK147513B (da)	1984-09-10	Analogifremgangsmaade til fremstilling af cefuroximestere
DK145262B (da)	1982-10-18	Analogifremgangsmaade til fremstilling af cephalosporansyrederivater og estere og salte deraf
SU847922A3 (ru)	1981-07-15	Способ получени - - -( -окси- -метил-НиКОТиНАМидО)- -( -ОКСифЕНил)АцЕТАМидО - -( -МЕТилТЕТРАзОл- -ил)ТиОМЕТил- -цЕфЕМ- -КАРбОНОВОй КиСлОТы
US4104469A (en)	1978-08-01	7-(Syn-α-alkoxy-iminofuryl)acetamido-3-(2-methyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
NO761438L (hu)	1976-11-02
HU176287B (en)	1981-01-28	Process for producing 7-bracket-2-thienylacetamido-bracket closed-3-triasolylthiomethyl-3-cepheme-4-carboxylic acid derivative
FR2583757A1 (fr)	1986-12-26	Acides propenylaminothiazolylcephalosporaniques 3-substitues et leurs esters
FI75168C (fi)	1988-05-09	Foerfarande foer framstaellning av natriumcefuroxim eller ett solvat daerav och natriumcefuroximtetrahydrofuransolvat anvaendbart som mellanprodukt vid foerfarandet.
US4103085A (en)	1978-07-25	7-(Syn-α-alkoxy-iminofurylacetamido-3-(2-carboxyalkyl-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-on-6-ylthiomethyl)-3-cephem-4-carboxylic acids
US3991051A (en)	1976-11-09	[(Oxyalkyl)thioacetyl]cephalosporin derivatives
NO744081L (hu)	1975-06-09
BE821243A (fr)	1975-04-18	Derives de la penicilline
NL8003186A (nl)	1980-12-03	Cefalosporine-verbindingen die geschikt zijn voor orale toediening.
JPS6156238B2 (hu)	1986-12-01
GB1604740A (en)	1981-12-16	7-isothiazolylthioacetamido-7-methoxycephalosporanic acid derivatives
SE447732B (sv)	1986-12-08	Nytt forfarande for rening av 7-/d(-)-alfa-(4-etyl-2,3-dioxo-l-piperazinkarboxamido)-alfa-(4-hydroxifenyl)acetamido/-3-/5-(1-metyl-tetrazolyl)tiometyl/-delta?723-cefem-4-karboxylsyra
US4003893A (en)	1977-01-18	3-Heterothio[(thioalkyl)thioacetyl]cephalosporanic derivatives
US3943131A (en)	1976-03-09	Trifluoromethylmercaptoacetamidocephalosporins
EP0068403A2 (en)	1983-01-05	Cephalosporin compound
NO792036L (no)	1979-12-28	Fremgangsmaate for fremstilling av cefalosporiner
DK164225B (da)	1992-05-25	Cephalosporinforbindelser til anvendelse som ernaeringsmaessige tilskud i dyrefoder