NO791996L - Fremgangsmaate for fremstilling av antibakterielt aktive iminotioazolyl-ureido-cefalosporiner - Google Patents

Fremgangsmaate for fremstilling av antibakterielt aktive iminotioazolyl-ureido-cefalosporiner

Info

Publication number: NO791996L
Authority: NO; Norway
Prior art keywords: amino; methyl; imino; dihydro; oct
Prior art date: 1978-06-16

Application number

NO791996A

Other languages

English (en)

Norwegian (no)

Inventor

Hermann Breuer

Uwe D Treuner

Theodor Denzel

Original Assignee

Squibb & Sons Inc

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.)

1978-06-16

Filing date

1979-06-15

Publication date

1979-12-18

1979-06-15 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1979-12-18 Publication of NO791996L publication Critical patent/NO791996L/no

Links

238000000034 method Methods 0.000 title claims description 32
230000000844 anti-bacterial effect Effects 0.000 title claims 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 60
150000001875 compounds Chemical class 0.000 claims description 45
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 36
-1 p-methoxybenzyl Chemical group 0.000 claims description 34
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
229940124587 cephalosporin Drugs 0.000 claims description 13
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 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
229910052700 potassium Inorganic materials 0.000 claims description 11
239000011591 potassium Substances 0.000 claims description 11
229910052708 sodium Inorganic materials 0.000 claims description 11
239000011734 sodium Substances 0.000 claims description 11
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 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 9
159000000000 sodium salts Chemical class 0.000 claims description 9
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 2
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 36
239000000203 mixture Substances 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 30
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
239000002253 acid Substances 0.000 description 14
DSIJXEVOJMBKAM-UHFFFAOYSA-M sodium;2-methyloct-2-enoate Chemical compound [Na+].CCCCCC=C(C)C([O-])=O DSIJXEVOJMBKAM-UHFFFAOYSA-M 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 9
229930186147 Cephalosporin Natural products 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
150000001780 cephalosporins Chemical class 0.000 description 8
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
125000001841 imino group Chemical group [H]N=* 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
230000010933 acylation Effects 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
KDBQZXYVWWRTAJ-UHFFFAOYSA-N 2-methyloct-2-enoic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCCCCC=C(C)C(O)=O KDBQZXYVWWRTAJ-UHFFFAOYSA-N 0.000 description 4
WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229920001429 chelating resin Polymers 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 3
239000003456 ion exchange resin Substances 0.000 description 3
229920003303 ion-exchange polymer Polymers 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
238000002953 preparative HPLC Methods 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
NQBRFIXRZDTIRQ-UHFFFAOYSA-N (4-methoxyphenyl)methyl n-diazocarbamate Chemical compound COC1=CC=C(COC(=O)N=[N+]=[N-])C=C1 NQBRFIXRZDTIRQ-UHFFFAOYSA-N 0.000 description 2
IYGXEANJFKGLEH-UHFFFAOYSA-N 2-(2-amino-1,3-thiazol-4-yl)-2-[(4-methoxyphenyl)methoxycarbonylamino]acetic acid Chemical compound C1=CC(OC)=CC=C1COC(=O)NC(C(O)=O)C1=CSC(N)=N1 IYGXEANJFKGLEH-UHFFFAOYSA-N 0.000 description 2
WCHTUBIWOSZGBP-UHFFFAOYSA-N 2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-[(4-methoxyphenyl)methoxycarbonylamino]acetic acid Chemical compound C1=CC(OC)=CC=C1COC(=O)NC(C(O)=O)C1=CSC(NC(=O)CCl)=N1 WCHTUBIWOSZGBP-UHFFFAOYSA-N 0.000 description 2
SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
241000607142 Salmonella Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OCAIDFZKQFECSE-UHFFFAOYSA-N 2-amino-2-(2-amino-1,3-thiazol-4-yl)acetic acid Chemical compound OC(=O)C(N)C1=CSC(N)=N1 OCAIDFZKQFECSE-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
IKWLIQXIPRUIDU-UHFFFAOYSA-N 8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCSC2CC(=O)N12 IKWLIQXIPRUIDU-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
241000588919 Citrobacter freundii Species 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
241000588697 Enterobacter cloacae Species 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
241000588770 Proteus mirabilis Species 0.000 description 1
241000588777 Providencia rettgeri Species 0.000 description 1
241000607715 Serratia marcescens Species 0.000 description 1
241000607760 Shigella sonnei Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
241000534944 Thia Species 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000004849 alkoxymethyl group Chemical group 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000002798 polar solvent Substances 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
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229940115939 shigella sonnei Drugs 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000005406 washing Methods 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (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)

NO791996A 1978-06-16 1979-06-15 Fremgangsmaate for fremstilling av antibakterielt aktive iminotioazolyl-ureido-cefalosporiner NO791996L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US91638078A	1978-06-16	1978-06-16

Publications (1)

Publication Number	Publication Date
NO791996L true NO791996L (no)	1979-12-18

Family

ID=25437172

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO791996A NO791996L (no)	1978-06-16	1979-06-15	Fremgangsmaate for fremstilling av antibakterielt aktive iminotioazolyl-ureido-cefalosporiner

Country Status (13)

Country	Link
JP (1)	JPS552681A (fr)
AU (1)	AU4789879A (fr)
BE (1)	BE877021A (fr)
DE (1)	DE2924296A1 (fr)
DK (1)	DK251979A (fr)
FR (1)	FR2428647A1 (fr)
GB (1)	GB2023142A (fr)
IT (1)	IT7949403A0 (fr)
LU (1)	LU81378A1 (fr)
NL (1)	NL7904694A (fr)
NO (1)	NO791996L (fr)
SE (1)	SE7905306L (fr)
ZA (1)	ZA792724B (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS54117494A (en) *	1978-03-03	1979-09-12	Takeda Chem Ind Ltd	Cephalosporin compound and its preparation
US4275062A (en) *	1979-09-19	1981-06-23	E. R. Squibb & Sons, Inc.	Aminothiazolyl ureido sulfoxide cephalosporins
DE3007685A1 (de)	1980-02-29	1981-10-01	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue cephylosporine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
JPS57164154A (en) *	1981-04-02	1982-10-08	Matsushita Electric Ind Co Ltd	Dielectric composition
JPS5854643U (ja) *	1981-10-09	1983-04-13	株式会社東芝	接触帯電器

1979
- 1979-06-01 ZA ZA792724A patent/ZA792724B/xx unknown
- 1979-06-08 AU AU47898/79A patent/AU4789879A/en not_active Abandoned
- 1979-06-13 IT IT7949403A patent/IT7949403A0/it unknown
- 1979-06-14 GB GB7920692A patent/GB2023142A/en not_active Withdrawn
- 1979-06-14 FR FR7915277A patent/FR2428647A1/fr not_active Withdrawn
- 1979-06-14 LU LU81378A patent/LU81378A1/de unknown
- 1979-06-15 NL NL7904694A patent/NL7904694A/xx not_active Application Discontinuation
- 1979-06-15 NO NO791996A patent/NO791996L/no unknown
- 1979-06-15 DE DE19792924296 patent/DE2924296A1/de not_active Withdrawn
- 1979-06-15 DK DK251979A patent/DK251979A/da not_active Application Discontinuation
- 1979-06-15 SE SE7905306A patent/SE7905306L/xx unknown
- 1979-06-15 BE BE0/195775A patent/BE877021A/fr unknown
- 1979-06-16 JP JP7623579A patent/JPS552681A/ja active Pending

Also Published As

Publication number	Publication date
IT7949403A0 (it)	1979-06-13
FR2428647A1 (fr)	1980-01-11
SE7905306L (sv)	1979-12-17
DK251979A (da)	1979-12-17
LU81378A1 (de)	1979-09-12
AU4789879A (en)	1979-12-20
JPS552681A (en)	1980-01-10
NL7904694A (nl)	1979-12-18
DE2924296A1 (de)	1979-12-20
GB2023142A (en)	1979-12-28
ZA792724B (en)	1980-08-27
BE877021A (fr)	1979-12-17

Publication	Publication Date	Title
CA1272713A (fr)	1990-08-14	Carboxyalkenamidocephalosporines
Lattrell et al.	1988	Synthesis and structure-activity relationships in the cefpirome series I. 7-[2-(2-Aminothiazol-4-yl)-2-(Z)-oxyiminoacetamido]-3-[(substituted-1-pyridinio) methyl]-ceph-3-em-4-carboxylates
NL8400229A (nl)	1984-08-16	Gesubstitueerde vinyl-cefalosporinen; werkwijze voor het bereiden daarvan; farmaceutische preparaten.
US4142046A (en)	1979-02-27	Intermediates for the preparation of 7-acyl-3-(substituted triazolylthiomethyl)cephalosporins
NO159797B (no)	1988-10-31	Analogifremgangsmaate ved fremstilling av nye terapeutisk aktive cefalosporinsalter.
JPS6153359B2 (fr)	1986-11-17
GB2031425A (en)	1980-04-23	3-unsubstituted-3-cephem compounds
CA1154434A (fr)	1983-09-27	Derives de l'acide hydroxamique et de 7-[(2-amino-4-thiazolyl oximino] cephalosporines
NO166860B (no)	1991-06-03	Analogifremgangsmaate for fremstilling av terapeutisk aktive monosulfaktamer.
NO161068B (no)	1989-03-20	Analogifremgangsmaate for fremstilling av terapeutisk aktive 7beta-((z)-2-2-aminothiazol-4-yl)-2-oxyimino-ace-tamido)-3-cefem-4-carboxylsyreforbindelser.
US4971962A (en)	1990-11-20	Cephalosporin compounds
US4399132A (en)	1983-08-16	7-Beta-[alpha-syn-methoxyimino-alpha-(2-aminothiazol-4-yl)-acetamido]-3-[(1,2,3-thiadiazol-5-ylthio)methyl]-3-cephem-4-carboxylic acid and C1 -C6 alkyl derivatives thereof
NO791996L (no)	1979-12-18	Fremgangsmaate for fremstilling av antibakterielt aktive iminotioazolyl-ureido-cefalosporiner
US4061748A (en)	1977-12-06	7-(α-(4-Hydroxy-1,5-naphthyridine-3-carbonamido)-α-phenylacetamido) cephalosporin derivatives
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
KR870002181B1 (ko)	1987-12-28	세팔로스포린의 제조방법
US4460582A (en)	1984-07-17	3-Carboxybenzyl cephems
US4018921A (en)	1977-04-19	Substituted phenylglycylcephalosporins
NO162470B (no)	1989-09-25	Analogifremgangsm te for fremstilling av terapeutisk aktiv ester av 7beta-(2-(2-amino-tiazol-4-yl)acetamido)-3-(((1-(2-dimetylamino-etyl)-1h-tetrazol-5-yl)tio)metyl)-cef-3-em-4-karboksylsyre.
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
FR2465738A1 (fr)	1981-03-27	Sulfoxydes d'aminothiazolyl ureido cephalosporines a action antibacterienne, et procede et intermediaires permettant de les preparer
US4501743A (en)	1985-02-26	Iminothiazolyl ureido cephalosporins
US4229573A (en)	1980-10-21	7α-Methoxycephalosporin derivatives
US4461767A (en)	1984-07-24	Iminothiazolyl ureido cephalosporins
JPS6026800B2 (ja)	1985-06-25	新規な７α−メトキシセフアロスポリン類およびその製造法