NO864646L - Mellomprodukter for fremstilling av beta-laktam antibiotika. - Google Patents

Mellomprodukter for fremstilling av beta-laktam antibiotika.

Info

Publication number: NO864646L
Authority: NO; Norway
Prior art keywords: alkyl; formula; amino; group; compounds
Prior art date: 1985-11-21

Application number

NO864646A

Other languages

English (en)

Norwegian (no)

Other versions

NO864646D0 (no

Inventor

John Peter Bailey

Georges Pasquest

Original Assignee

Ici Plc

Ici Pharma

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.)

1985-11-21

Filing date

1986-11-20

Publication date

1987-05-22

1986-11-20 Application filed by Ici Plc, Ici Pharma filed Critical Ici Plc

1986-11-20 Publication of NO864646D0 publication Critical patent/NO864646D0/no

1987-05-22 Publication of NO864646L publication Critical patent/NO864646L/no

Links

238000002360 preparation method Methods 0.000 title description 7
239000000543 intermediate Substances 0.000 title description 4
239000003782 beta lactam antibiotic agent Substances 0.000 title 1
239000002132 β-lactam antibiotic Substances 0.000 title 1
229940124586 β-lactam antibiotics Drugs 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims description 88
-1 ion salts Chemical class 0.000 claims description 78
150000001875 compounds Chemical class 0.000 claims description 43
238000000034 method Methods 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229930186147 Cephalosporin Natural products 0.000 claims description 4
229940124587 cephalosporin Drugs 0.000 claims description 4
150000001780 cephalosporins Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 2
239000003242 anti bacterial agent Substances 0.000 claims 1
229940088710 antibiotic agent Drugs 0.000 claims 1
230000003115 biocidal effect Effects 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 description 20
239000001257 hydrogen Substances 0.000 description 20
125000003545 alkoxy group Chemical group 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
229910052736 halogen Inorganic materials 0.000 description 9
150000002367 halogens Chemical class 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000005115 alkyl carbamoyl group Chemical group 0.000 description 8
125000004093 cyano group Chemical group *C#N 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
125000003282 alkyl amino group Chemical group 0.000 description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
125000004356 hydroxy functional group Chemical group O* 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical group CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
239000000203 mixture Substances 0.000 description 6
125000005236 alkanoylamino group Chemical group 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
125000000753 cycloalkyl group Chemical group 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
239000001301 oxygen Chemical group 0.000 description 5
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
125000004663 dialkyl amino group Chemical group 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000007858 starting material Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000005864 Sulphur Substances 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
125000002837 carbocyclic group Chemical group 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
125000005368 heteroarylthio group Chemical group 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N benzofuran Natural products C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
125000001072 heteroaryl group Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
125000005544 phthalimido group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
SBCWTVNLZGEXFB-IOJJLOCKSA-N (6r)-7-amino-3-(ethylaminomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(CNCC)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 SBCWTVNLZGEXFB-IOJJLOCKSA-N 0.000 description 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
PYPGAMUVJIIXGC-UHFFFAOYSA-N 2,3-dihydro-1,2-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)CNOC2=C1 PYPGAMUVJIIXGC-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
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
NCTHHJRIJGFPTG-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)-4-[7-[[6,7-bis(aziridin-1-yl)-5,8-dioxoquinazolin-4-yl]amino]heptylamino]quinazoline-5,8-dione Chemical group C1CN1C=1C(=O)C2=C(NCCCCCCCNC=3C=4C(=O)C(N5CC5)=C(N5CC5)C(=O)C=4N=CN=3)N=CN=C2C(=O)C=1N1CC1 NCTHHJRIJGFPTG-UHFFFAOYSA-N 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
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical group FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000004183 alkoxy alkyl group Chemical group 0.000 description 1
125000000676 alkoxyimino group Chemical group 0.000 description 1
125000005103 alkyl silyl group Chemical group 0.000 description 1
125000005153 alkyl sulfamoyl group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
125000005122 aminoalkylamino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000005335 azido alkyl group Chemical group 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000000463 material Substances 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000002002 slurry Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
- C07D463/16—Nitrogen atoms
- 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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO864646A 1985-11-21 1986-11-20 Mellomprodukter for fremstilling av beta-laktam antibiotika. NO864646L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP85402266		1985-11-21

Publications (2)

Publication Number	Publication Date
NO864646D0 NO864646D0 (no)	1986-11-20
NO864646L true NO864646L (no)	1987-05-22

Family

ID=8194553

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO864646A NO864646L (no)	1985-11-21	1986-11-20	Mellomprodukter for fremstilling av beta-laktam antibiotika.

Country Status (10)

Country	Link
US (1)	US5053500A (de)
EP (1)	EP0224385A3 (de)
JP (1)	JPH0676416B2 (de)
AU (1)	AU592128B2 (de)
DK (1)	DK559786A (de)
FI (1)	FI864712A7 (de)
IE (1)	IE862850L (de)
NO (1)	NO864646L (de)
NZ (1)	NZ218344A (de)
ZA (1)	ZA868466B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4673737A (en) *	1985-08-02	1987-06-16	Harvard University	7-acylamino-(or 7-amino)-3-trifluoromethylsulfonyloxy-1-carba(1-dethia)-3-cephem-4-carboxylic acids and esters thereof
IE862850L (en) *	1985-11-21	1987-05-21	Inst Animal Health Ltd	Intermediates for the preparation of beta-lactam antibiotics
US5300763A (en) *	1990-11-30	1994-04-05	Olympus Optical Co., Ltd.	Information recording/reproducing apparatus

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE634644A (de) *	1963-07-10
FR1584713A (de) *	1967-01-18	1970-01-02
US3644347A (en) *	1969-02-26	1972-02-22	Lilly Co Eli	3-aminomethyl cephalosporin compounds
US3539562A (en) *	1969-05-02	1970-11-10	Squibb & Sons Inc	Alpha - amino - 2,4,6 - cycloheptatrienylmethylcephalosporins
DE2714880A1 (de) *	1977-04-02	1978-10-26	Hoechst Ag	Cephemderivate und verfahren zu ihrer herstellung
DE2818263A1 (de) *	1978-04-26	1979-11-08	Bayer Ag	Beta-lactamantibiotika
IL59395A (en) *	1979-03-06	1983-07-31	Gist Brocades Nv	Bromo-substituted deacetoxycephalosporin derivatives and their preparation
GB2103205A (en) *	1981-06-15	1983-02-16	Fujisawa Pharmaceutical Co	New cephem compounds
US4457929A (en) *	1982-03-29	1984-07-03	Bristol-Myers Company	3-Quaternary ammonium methyl)-substituted cephalosporin derivatives
JPS6064986A (ja) *	1983-09-20	1985-04-13	Toyama Chem Co Ltd	セファロスポリン類の製造法
IE862850L (en) *	1985-11-21	1987-05-21	Inst Animal Health Ltd	Intermediates for the preparation of beta-lactam antibiotics

1986
- 1986-10-29 IE IE862850A patent/IE862850L/xx unknown
- 1986-11-06 ZA ZA868466A patent/ZA868466B/xx unknown
- 1986-11-14 AU AU65149/86A patent/AU592128B2/en not_active Ceased
- 1986-11-19 FI FI864712A patent/FI864712A7/fi not_active Application Discontinuation
- 1986-11-20 NO NO864646A patent/NO864646L/no unknown
- 1986-11-20 NZ NZ218344A patent/NZ218344A/xx unknown
- 1986-11-20 EP EP86309105A patent/EP0224385A3/de not_active Withdrawn
- 1986-11-20 JP JP61275500A patent/JPH0676416B2/ja not_active Expired - Lifetime
- 1986-11-21 DK DK559786A patent/DK559786A/da not_active Application Discontinuation
1990
- 1990-07-20 US US07/555,355 patent/US5053500A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU592128B2 (en)	1990-01-04
JPH0676416B2 (ja)	1994-09-28
FI864712A0 (fi)	1986-11-19
EP0224385A2 (de)	1987-06-03
US5053500A (en)	1991-10-01
AU6514986A (en)	1987-05-28
DK559786D0 (da)	1986-11-21
NO864646D0 (no)	1986-11-20
JPS62164687A (ja)	1987-07-21
ZA868466B (en)	1988-03-30
EP0224385A3 (de)	1988-10-19
IE862850L (en)	1987-05-21
FI864712A7 (fi)	1987-05-22
DK559786A (da)	1987-05-22
NZ218344A (en)	1989-07-27

Publication	Publication Date	Title
KR940000112B1 (ko)	1994-01-05	신규의 3-치환 세펨화합물 및 그의 제조방법
EP0153709B1 (de)	1991-08-14	Cephalosporinverbindungen
AU2016363937A1 (en)	2018-06-14	Inhibitors of metallo-beta-lactamases
CA1225390A (en)	1987-08-11	3-bicyclicpyridinium-methyl cephalosporins
EP0074268A2 (de)	1983-03-16	Thieno- und furopyridiniumsubstituierte Cephalosporinderivate
JPS6133189A (ja)	1986-02-17	セファロスポリン誘導体及びその製法
DE3854684T2 (de)	1996-03-28	Cephalosporinverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate.
US5329002A (en)	1994-07-12	Antibacterial cephalosporin compounds
US5439904A (en)	1995-08-08	2-spiro(2'-spirocycloalkyl)cyclopropyl cephalosporin sulfones as antiinflammatory and antigenerative agents
NO864646L (no)	1987-05-22	Mellomprodukter for fremstilling av beta-laktam antibiotika.
US5013731A (en)	1991-05-07	Cephalosporin compounds
EP0315997B1 (de)	1994-04-20	Cephalosporinverbindungen und antibakterielle Mittel
US5028601A (en)	1991-07-02	Cephalosporin compounds and antibacterial agents
US4868173A (en)	1989-09-19	Cephalosporin derivatives
HU186999B (en)	1985-10-28	Process for the preparation of cephem-caraoxylic acid containing heterocyclic group in 3-position
GB2140807A (en)	1984-12-05	7-oxo-4-thia-1-azabicyclo(3.2.0)heptene derivatives
JP2002507616A (ja)	2002-03-12	抗生物質としての環状アミノグアニジン置換基を有するセファロスポリン
HU184680B (en)	1984-09-28	Process for producing ceph-3-eme-4-carboxylic acid derivatives containing amino-thiazolyl group in the side chain
WO1992002523A1 (fr)	1992-02-20	Nouveau compose de cephalosporine
CA1146947A (en)	1983-05-24	Cephem derivatives and processes for their preparation
JPS6013787A (ja)	1985-01-24	新規なアゼチジノン誘導体およびその塩類
PH26648A (en)	1992-09-04	Acyl derivatives
WO1986000071A1 (fr)	1986-01-03	Composes de cephem