NO752936L - - Google Patents

Info

Publication number: NO752936L
Authority: NO; Norway
Prior art keywords: compound; stated; dithiaaz; sulfoxide; isopropenyl acetate
Prior art date: 1974-08-30

Application number

NO752936A

Other languages

English (en)

Norwegian (no)

Inventor

R G Micetich

C G Chin

R B Morin

Original Assignee

Connlab Holdings Ltd

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.)

1974-08-30

Filing date

1975-08-27

Publication date

1976-03-02

1975-08-27 Application filed by Connlab Holdings Ltd filed Critical Connlab Holdings Ltd

1975-09-12 Priority to NO753127A priority Critical patent/NO753127L/no

1976-03-02 Publication of NO752936L publication Critical patent/NO752936L/no

Links

150000001875 compounds Chemical class 0.000 claims description 33
-1 e.g. -CH2 OCH3 Chemical class 0.000 claims description 28
150000003462 sulfoxides Chemical class 0.000 claims description 26
238000000034 method Methods 0.000 claims description 15
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 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 5
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 2
GYXZGJUHAUJMRW-UHFFFAOYSA-N 4-(methylsulfanylmethyl)azetidin-2-one Chemical group CSCC1CC(=O)N1 GYXZGJUHAUJMRW-UHFFFAOYSA-N 0.000 claims description 2
VWFAQEFMKBVHSH-UHFFFAOYSA-N 4-anilino-1-trimethylsilylazetidin-2-one Chemical group C[Si](C)(C)N1C(CC1NC1=CC=CC=C1)=O VWFAQEFMKBVHSH-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
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
239000007858 starting material Substances 0.000 claims 3
ZGZUKKMFYTUYHA-HNNXBMFYSA-N (2s)-2-amino-3-(4-phenylmethoxyphenyl)propane-1-thiol Chemical compound C1=CC(C[C@@H](CS)N)=CC=C1OCC1=CC=CC=C1 ZGZUKKMFYTUYHA-HNNXBMFYSA-N 0.000 claims 1
UUVXNIKLDPROFH-UHFFFAOYSA-N 1-(methoxymethyl)-4-phenoxyazetidin-2-one Chemical group COCN1C(CC1OC1=CC=CC=C1)=O UUVXNIKLDPROFH-UHFFFAOYSA-N 0.000 claims 1
JTFLUJJESVAQGM-UHFFFAOYSA-N 1-aminoazetidin-2-one Chemical compound NN1CCC1=O JTFLUJJESVAQGM-UHFFFAOYSA-N 0.000 claims 1
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 18
229940124587 cephalosporin Drugs 0.000 description 15
229930186147 Cephalosporin Chemical class 0.000 description 14
150000001780 cephalosporins Chemical class 0.000 description 14
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 13
238000004519 manufacturing process Methods 0.000 description 13
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000006260 foam Substances 0.000 description 10
238000002329 infrared spectrum Methods 0.000 description 10
239000010410 layer Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 9
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 8
229930182555 Penicillin Natural products 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229940056360 penicillin g Drugs 0.000 description 5
150000002960 penicillins Chemical class 0.000 description 5
DNPOVSLJNLLGMA-SJUANORRSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)COC1=CC=CC=C1 DNPOVSLJNLLGMA-SJUANORRSA-N 0.000 description 4
NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
238000001149 thermolysis Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
229930195708 Penicillin V Natural products 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
229940106164 cephalexin Drugs 0.000 description 3
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
229940061627 chloromethyl methyl ether Drugs 0.000 description 3
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000013067 intermediate product Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
229940056367 penicillin v Drugs 0.000 description 3
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000010183 spectrum analysis Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
SQQJXTVBRWSCQH-UHFFFAOYSA-N 4-(phenoxymethyl)azetidin-2-one Chemical compound O=C1CC(COC2=CC=CC=C2)N1 SQQJXTVBRWSCQH-UHFFFAOYSA-N 0.000 description 2
CQOXWATVSJPLQB-UHFFFAOYSA-N 4-phenoxyazetidin-2-one Chemical compound N1C(=O)CC1OC1=CC=CC=C1 CQOXWATVSJPLQB-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 2
MIFYHUACUWQUKT-UHFFFAOYSA-N Isopenicillin N Natural products OC(=O)C1C(C)(C)SC2C(NC(=O)CCCC(N)C(O)=O)C(=O)N21 MIFYHUACUWQUKT-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229950008644 adicillin Drugs 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
229960001139 cefazolin Drugs 0.000 description 2
MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 2
HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
NNQIJOYQWYKBOW-UHFFFAOYSA-N desacetoxycephalosphorin G Natural products S1CC(C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 NNQIJOYQWYKBOW-UHFFFAOYSA-N 0.000 description 2
238000010586 diagram Methods 0.000 description 2
WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
MIFYHUACUWQUKT-GPUHXXMPSA-N penicillin N Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@H](NC(=O)CCC[C@@H](N)C(O)=O)C(=O)N21 MIFYHUACUWQUKT-GPUHXXMPSA-N 0.000 description 2
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 2
238000005636 thioacylation reaction Methods 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 2
LVFXAQURPCNCRL-UHFFFAOYSA-N 1-methyl-4-(methylamino)azetidin-2-one Chemical compound CN1C(CC1NC)=O LVFXAQURPCNCRL-UHFFFAOYSA-N 0.000 description 1
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 1
CYXQCKQUCDEMCV-UHFFFAOYSA-N 4-(methoxymethylsulfanylmethyl)azetidin-2-one Chemical compound COCSCC1CC(N1)=O CYXQCKQUCDEMCV-UHFFFAOYSA-N 0.000 description 1
FNTXXNUMASJJFN-UHFFFAOYSA-N 4-(methylamino)azetidin-2-one Chemical compound CNC1CC(N1)=O FNTXXNUMASJJFN-UHFFFAOYSA-N 0.000 description 1
CORGJRDCISMIAH-UHFFFAOYSA-N 4-(phenoxymethyl)-1-trimethylsilylazetidin-2-one Chemical compound C[Si](C)(C)N1C(CC1COC1=CC=CC=C1)=O CORGJRDCISMIAH-UHFFFAOYSA-N 0.000 description 1
LXVFDEAHOFQMGO-UHFFFAOYSA-N 4-(trimethylsilylsulfanylmethyl)azetidin-2-one Chemical compound C[Si](SCC1CC(N1)=O)(C)C LXVFDEAHOFQMGO-UHFFFAOYSA-N 0.000 description 1
LDWLCBWKIVZGOO-UHFFFAOYSA-N 4-anilino-1-methylazetidin-2-one Chemical compound C1C(=O)N(C)C1NC1=CC=CC=C1 LDWLCBWKIVZGOO-UHFFFAOYSA-N 0.000 description 1
NVIAYEIXYQCDAN-UHFFFAOYSA-N 7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)C12 NVIAYEIXYQCDAN-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
ZOTVPMREKCDNPT-UHFFFAOYSA-N C1(=CC=CC=C1)NC1CC(N1)=O Chemical compound C1(=CC=CC=C1)NC1CC(N1)=O ZOTVPMREKCDNPT-UHFFFAOYSA-N 0.000 description 1
BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical class CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
UQLLWWBDSUHNEB-CZUORRHYSA-N Cefaprin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CSC1=CC=NC=C1 UQLLWWBDSUHNEB-CZUORRHYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
102220347004 c.89G>A Human genes 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 1
229950004030 cefaloglycin Drugs 0.000 description 1
CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
229960003866 cefaloridine Drugs 0.000 description 1
229960000603 cefalotin Drugs 0.000 description 1
229960004350 cefapirin 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
238000001311 chemical methods and process Methods 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
QZULOCFNEVXFJA-UHFFFAOYSA-N n-phenoxycarbamothioyl chloride Chemical compound ClC(=S)NOC1=CC=CC=C1 QZULOCFNEVXFJA-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
KOSYAAIZOGNATQ-UHFFFAOYSA-N o-phenyl chloromethanethioate Chemical compound ClC(=S)OC1=CC=CC=C1 KOSYAAIZOGNATQ-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052760 oxygen Chemical group 0.000 description 1
239000001301 oxygen Chemical group 0.000 description 1
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
229940117953 phenylisothiocyanate Drugs 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
IKUJAIDSWVXUGG-UHFFFAOYSA-N prop-1-enyl acetate Chemical compound CC=COC(C)=O IKUJAIDSWVXUGG-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO752936A 1974-08-30 1975-08-27 NO752936L (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO753127A NO753127L (fr)	1974-08-30	1975-09-12

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA208,248A CA1029373A (fr)	1974-08-30	1974-08-30	1,2,4-dithiaaz-3-enes

Publications (1)

Publication Number	Publication Date
NO752936L true NO752936L (fr)	1976-03-02

Family

ID=4101026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO752936A NO752936L (fr)	1974-08-30	1975-08-27

Country Status (14)

Country	Link
US (1)	US4006139A (fr)
JP (1)	JPS5141387A (fr)
AT (1)	AT338423B (fr)
BE (1)	BE832172A (fr)
CA (1)	CA1029373A (fr)
CH (1)	CH612438A5 (fr)
DE (1)	DE2534521A1 (fr)
DK (1)	DK141407B (fr)
FI (1)	FI752337A7 (fr)
FR (1)	FR2283143A1 (fr)
GB (1)	GB1500399A (fr)
NL (1)	NL7510180A (fr)
NO (1)	NO752936L (fr)
SE (1)	SE7509568L (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0343834U (fr) *	1989-09-07	1991-04-24

1974
- 1974-08-30 CA CA208,248A patent/CA1029373A/fr not_active Expired
1975
- 1975-04-24 US US05/571,427 patent/US4006139A/en not_active Expired - Lifetime
- 1975-07-15 GB GB29698/75A patent/GB1500399A/en not_active Expired
- 1975-08-01 DE DE19752534521 patent/DE2534521A1/de not_active Withdrawn
- 1975-08-06 BE BE158979A patent/BE832172A/fr unknown
- 1975-08-12 CH CH1047375A patent/CH612438A5/xx not_active IP Right Cessation
- 1975-08-12 JP JP50097247A patent/JPS5141387A/ja active Pending
- 1975-08-12 DK DK365475AA patent/DK141407B/da unknown
- 1975-08-18 FI FI752337A patent/FI752337A7/fi not_active Application Discontinuation
- 1975-08-19 AT AT640475A patent/AT338423B/de not_active IP Right Cessation
- 1975-08-27 NO NO752936A patent/NO752936L/no unknown
- 1975-08-28 NL NL7510180A patent/NL7510180A/xx not_active Application Discontinuation
- 1975-08-28 FR FR7526527A patent/FR2283143A1/fr active Granted
- 1975-08-28 SE SE7509568A patent/SE7509568L/xx unknown

Also Published As

Publication number	Publication date
NL7510180A (nl)	1976-03-02
CH612438A5 (fr)	1979-07-31
ATA640475A (de)	1976-12-15
FR2283143A1 (fr)	1976-03-26
DK141407B (da)	1980-03-10
GB1500399A (en)	1978-02-08
AT338423B (de)	1977-08-25
JPS5141387A (en)	1976-04-07
CA1029373A (fr)	1978-04-11
US4006139A (en)	1977-02-01
FI752337A7 (fr)	1976-03-02
DE2534521A1 (de)	1976-03-11
DK141407C (fr)	1980-09-01
SE7509568L (sv)	1976-03-01
FR2283143B1 (fr)	1979-05-25
BE832172A (fr)	1975-12-01
DK365475A (fr)	1976-03-01

Publication	Publication Date	Title
FI70714B (fi)	1986-06-26	Foerfarande foer framstaellning av 6-/d-alfa-amino-(p-hydroxifenyl)-acetamido/-penicillansyra
NO140931B (no)	1979-09-03	Analogifremgangsmaate til fremstilling av terapeutisk virksomme estere av alfa-aminobenzylpenicilliner
EP0503453B1 (fr)	2001-05-09	Procédé pour la préparation de céphalosporines, ainsi qu'intermédiaires dans ce procédé
CA1144155A (fr)	1983-04-05	Methode pour retirer un groupe allylique dans des esters, carbonates et carbamates allyliques
FI56841C (fi)	1980-04-10	Foerfarande foer framstaellning av 7-acylaminocefalosporansyraderivat och 6-acylaminopenicillansyraderivat
NO148375B (no)	1983-06-20	Analogifremgangsmaate til fremstilling av terapeutisk virksomme 3-klor-7-alfa-amino-acylcefalosporinforbindelser
JPS6124396B2 (fr)	1986-06-10
NO752936L (fr)	1976-03-02
US4008229A (en)	1977-02-15	Halo substituted β-lactam antibiotics
FI75165B (fi)	1988-01-29	Foerbaettrat foerfarande foer framstaellning av penicillansyraklormetylestrar.
NO753127L (fr)	1976-03-02
US4035354A (en)	1977-07-12	Thioamides of beta-lactam antibiotics
NO148376B (no)	1983-06-20	Analogifremgangsmaate til fremstilling av terapeutisk virksomme 7-acylamino-3-halogen-cefalosporinforbindelser
NO153646B (no)	1986-01-20	Fremgangsmaate til fremstilling av en mantel for en behandlingsmaskin med flere skruer, samt mantel for slik behandlingsmaskin.
NO761352L (fr)	1976-10-25
EP0022326A1 (fr)	1981-01-14	Procédé pour la séparation chimique de la chaîne latérale acyle des céphalosporines et pénicillines
CA1071213A (fr)	1980-02-05	Thiazoleneazetidinones derives de penicillinsul foxydes
EP0117872A1 (fr)	1984-09-12	Procede de preparation de composes de cephalosporine
US4304909A (en)	1981-12-08	Process for producing 7-(D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl)acetamido)-3-(5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl)-.DELTA.3 -cephem-4-carboxylic acid and a pharmaceutically acceptable salt thereof
CA1067892A (fr)	1979-12-11	Composes iodes
CA1063610A (fr)	1979-10-02	Thiazoleneazetidinones derives de dithiazeneazetidinones
CA1056816A (fr)	1979-06-19	Procede pour la conversion de l'acide 6-aminopenicillanique (6-apa) en acide 7-aminodesacetoxycephalosporanique (7-adca)
US5079146A (en)	1992-01-07	Method of protection of the carboxy groups in the chemistry of β-lactam compounds
US3682896A (en)	1972-08-08	Preparation of 6-acylaminopenicillanic acids
CA1115692A (fr)	1982-01-05	Analogues oxygenes de la cephalosporine