DE2726394C2 - - Google Patents
Info
- Publication number
- DE2726394C2 DE2726394C2 DE2726394A DE2726394A DE2726394C2 DE 2726394 C2 DE2726394 C2 DE 2726394C2 DE 2726394 A DE2726394 A DE 2726394A DE 2726394 A DE2726394 A DE 2726394A DE 2726394 C2 DE2726394 C2 DE 2726394C2
- Authority
- DE
- Germany
- Prior art keywords
- mixture
- liters
- chloride
- reaction
- methyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- -1 4-nitrobenzyloxy Chemical group 0.000 claims description 58
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 35
- 239000000292 calcium oxide Substances 0.000 claims description 35
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 239000004593 Epoxy Substances 0.000 claims description 18
- 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 15
- 230000008569 process Effects 0.000 claims description 15
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 112
- 239000000203 mixture Substances 0.000 description 68
- 239000011541 reaction mixture Substances 0.000 description 42
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 22
- WDRFYIPWHMGQPN-UHFFFAOYSA-N 2-chloroisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Cl)C(=O)C2=C1 WDRFYIPWHMGQPN-UHFFFAOYSA-N 0.000 description 21
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000012320 chlorinating reagent Substances 0.000 description 16
- 238000007363 ring formation reaction Methods 0.000 description 16
- 239000000463 material Substances 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 14
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 13
- 239000003054 catalyst Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 229930182555 Penicillin Natural products 0.000 description 9
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound 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 9
- 239000000047 product Substances 0.000 description 9
- WNMFNGGUHIIQJE-BEZSAJEZSA-N (4-nitrophenyl)methyl (5r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(C(S2=O)(C)C)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)COC1=CC=CC=C1 WNMFNGGUHIIQJE-BEZSAJEZSA-N 0.000 description 8
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 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 7
- 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 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 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 7
- 239000000376 reactant Substances 0.000 description 7
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- 239000000460 chlorine Substances 0.000 description 6
- 229940049954 penicillin Drugs 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 150000001781 cephams Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 3
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002960 penicillins Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HBKWKOGDTHDLLR-IUAJRMLHSA-N (4-nitrophenyl)methyl (6r)-3-methylidene-5,8-dioxo-7-[(2-phenoxyacetyl)amino]-5$l^{4}-thia-1-azabicyclo[4.2.0]octane-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1C(=C)CS(=O)[C@H]2N1C(=O)C2NC(=O)COC1=CC=CC=C1 HBKWKOGDTHDLLR-IUAJRMLHSA-N 0.000 description 2
- 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 2
- KDXFMMHNGFNJFA-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinyl chloride Chemical compound ClS(=O)C1CC(=O)N1 KDXFMMHNGFNJFA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OGEBVIRSYGXOGZ-GELUPKEKSA-N O=S1C(C)(C)C(C(O)=O)N2C(=O)C[C@H]21 Chemical compound O=S1C(C)(C)C(C(O)=O)N2C(=O)C[C@H]21 OGEBVIRSYGXOGZ-GELUPKEKSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229930195708 Penicillin V Natural products 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- ZRRLCCCOCSDAKF-UHFFFAOYSA-N azetidin-2-one thionyl dichloride Chemical compound ClS(Cl)=O.O=C1CCN1 ZRRLCCCOCSDAKF-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000002274 desiccant Substances 0.000 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 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229940056360 penicillin g Drugs 0.000 description 2
- 229940056367 penicillin v Drugs 0.000 description 2
- 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 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DYQFFOLIFFHFFN-RWUBOQFLSA-N (5R)-3,3-dimethyl-2-[(4-nitrophenyl)methyl]-4,7-dioxo-6-[(2-phenylacetyl)amino]-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound CC1(C(N2[C@H](S1=O)C(C2=O)NC(=O)CC3=CC=CC=C3)(CC4=CC=C(C=C4)[N+](=O)[O-])C(=O)O)C DYQFFOLIFFHFFN-RWUBOQFLSA-N 0.000 description 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- WEBVTPPSMMFBQU-UHFFFAOYSA-N 1,1-dibromo-2-chloroethane Chemical compound ClCC(Br)Br WEBVTPPSMMFBQU-UHFFFAOYSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- SCEKDQTVGHRSNS-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrobenzene Chemical group CC1=CC(C)=C([N+]([O-])=O)C(C)=C1 SCEKDQTVGHRSNS-UHFFFAOYSA-N 0.000 description 1
- ADFIFDHDLIZVFW-UHFFFAOYSA-N 1-chloropiperidine-2,6-dione Chemical compound ClN1C(=O)CCCC1=O ADFIFDHDLIZVFW-UHFFFAOYSA-N 0.000 description 1
- PVFYLJVDDZPUMC-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-(3-acetamido-2-chlorosulfinyl-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound CC(=O)NC1C(S(Cl)=O)N(C(C(C)=C)C(=O)OCC(Cl)(Cl)Cl)C1=O PVFYLJVDDZPUMC-UHFFFAOYSA-N 0.000 description 1
- ZZGYTZZZKCQAHC-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound O=C1N(C(C(=C)C)C(=O)OCC(Cl)(Cl)Cl)C(S(Cl)=O)C1NC(=O)COC1=CC=CC=C1 ZZGYTZZZKCQAHC-UHFFFAOYSA-N 0.000 description 1
- RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
- AYKSPIBLOMDDGD-UHFFFAOYSA-N 2-(chlorocarbamoyl)benzenesulfonic acid Chemical compound ClN=C(O)C1=CC=CC=C1S(O)(=O)=O AYKSPIBLOMDDGD-UHFFFAOYSA-N 0.000 description 1
- SOWHKYPBHNVZKE-UHFFFAOYSA-N 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-2-[(4-methoxyphenyl)methyl]-3-methylbut-3-enoic acid Chemical compound CC(=C)C(CC1=CC=C(C=C1)OC)(C(=O)O)N2C(C(C2=O)NC(=O)CC3=CC=CC=C3)S(=O)Cl SOWHKYPBHNVZKE-UHFFFAOYSA-N 0.000 description 1
- RJNMTVYDAVCKEH-UHFFFAOYSA-N 2-[3-[(2-chloroacetyl)amino]-2-chlorosulfinyl-4-oxoazetidin-1-yl]-2-[(4-methoxyphenyl)methyl]-3-methylbut-3-enoic acid Chemical compound CC(=C)C(CC1=CC=C(C=C1)OC)(C(=O)O)N2C(C(C2=O)NC(=O)CCl)S(=O)Cl RJNMTVYDAVCKEH-UHFFFAOYSA-N 0.000 description 1
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- HEWUUUAOFGCFHK-UHFFFAOYSA-N 2-oxoazetidine-1-sulfinyl chloride Chemical compound ClS(=O)N1CCC1=O HEWUUUAOFGCFHK-UHFFFAOYSA-N 0.000 description 1
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
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- SXQMDKCJBNDLEP-UHFFFAOYSA-N 4-sulfinylazetidin-2-one Chemical class S(=O)=C1NC(C1)=O SXQMDKCJBNDLEP-UHFFFAOYSA-N 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
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- 229930186147 Cephalosporin Natural products 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical group ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
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- 229950005228 bromoform Drugs 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
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- 230000003197 catalytic effect Effects 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
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- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
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- 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
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- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
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- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- APZTZCAKUURTTG-UHFFFAOYSA-N n,3-dichloro-n-methylbenzenesulfonamide Chemical compound CN(Cl)S(=O)(=O)C1=CC=CC(Cl)=C1 APZTZCAKUURTTG-UHFFFAOYSA-N 0.000 description 1
- KZYWTQNZACMDPS-UHFFFAOYSA-N n,4-dichlorobenzamide Chemical compound ClNC(=O)C1=CC=C(Cl)C=C1 KZYWTQNZACMDPS-UHFFFAOYSA-N 0.000 description 1
- DHHIKEVWSRQXQP-UHFFFAOYSA-N n-chloro-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NCl)C=C1 DHHIKEVWSRQXQP-UHFFFAOYSA-N 0.000 description 1
- DTMXHYUPALBXFG-UHFFFAOYSA-N n-chloro-n,4-dimethylbenzenesulfonamide Chemical compound CN(Cl)S(=O)(=O)C1=CC=C(C)C=C1 DTMXHYUPALBXFG-UHFFFAOYSA-N 0.000 description 1
- PMXQDTBJZLOVSV-UHFFFAOYSA-N n-chloro-n-cyclohexylacetamide Chemical compound CC(=O)N(Cl)C1CCCCC1 PMXQDTBJZLOVSV-UHFFFAOYSA-N 0.000 description 1
- RWVOAAWFMJRINI-UHFFFAOYSA-N n-chloro-n-cyclohexylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(Cl)C1CCCCC1 RWVOAAWFMJRINI-UHFFFAOYSA-N 0.000 description 1
- YTYAPSXIGOPIOH-UHFFFAOYSA-N n-chloro-n-cyclohexylcyclohexanesulfonamide Chemical compound C1CCCCC1S(=O)(=O)N(Cl)C1CCCCC1 YTYAPSXIGOPIOH-UHFFFAOYSA-N 0.000 description 1
- YEXVRBUZIOSARW-UHFFFAOYSA-N n-chloro-n-cyclohexylethanesulfonamide Chemical compound CCS(=O)(=O)N(Cl)C1CCCCC1 YEXVRBUZIOSARW-UHFFFAOYSA-N 0.000 description 1
- FGJCTKGHKMARPX-UHFFFAOYSA-N n-chloro-n-ethyl-3-nitrobenzenesulfonamide Chemical compound CCN(Cl)S(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 FGJCTKGHKMARPX-UHFFFAOYSA-N 0.000 description 1
- XPTJWKPOBFHDHX-UHFFFAOYSA-N n-chloro-n-ethylbenzamide Chemical compound CCN(Cl)C(=O)C1=CC=CC=C1 XPTJWKPOBFHDHX-UHFFFAOYSA-N 0.000 description 1
- DQJKBIDVOSQVEV-UHFFFAOYSA-N n-chloro-n-methylacetamide Chemical compound CN(Cl)C(C)=O DQJKBIDVOSQVEV-UHFFFAOYSA-N 0.000 description 1
- WQJHFILPJKSLJW-UHFFFAOYSA-N n-chloro-n-phenylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(Cl)C1=CC=CC=C1 WQJHFILPJKSLJW-UHFFFAOYSA-N 0.000 description 1
- RKLUHJIBJTXOQU-UHFFFAOYSA-N n-chloro-n-phenylpropanamide Chemical compound CCC(=O)N(Cl)C1=CC=CC=C1 RKLUHJIBJTXOQU-UHFFFAOYSA-N 0.000 description 1
- UFICRBPXWFJZFC-UHFFFAOYSA-N n-chloro-n-propylbenzenesulfonamide Chemical compound CCCN(Cl)S(=O)(=O)C1=CC=CC=C1 UFICRBPXWFJZFC-UHFFFAOYSA-N 0.000 description 1
- HSPSCWZIJWKZKD-UHFFFAOYSA-N n-chloroacetamide Chemical compound CC(=O)NCl HSPSCWZIJWKZKD-UHFFFAOYSA-N 0.000 description 1
- CHVZPRDGLWBEMJ-UHFFFAOYSA-N n-chlorobenzenesulfonamide Chemical compound ClNS(=O)(=O)C1=CC=CC=C1 CHVZPRDGLWBEMJ-UHFFFAOYSA-N 0.000 description 1
- QQZCYGRKEOWFAG-UHFFFAOYSA-N n-chlorocyclohexanecarboxamide Chemical compound ClNC(=O)C1CCCCC1 QQZCYGRKEOWFAG-UHFFFAOYSA-N 0.000 description 1
- KFKMOYYBYVVHQQ-UHFFFAOYSA-N n-chloromethanesulfonamide Chemical compound CS(=O)(=O)NCl KFKMOYYBYVVHQQ-UHFFFAOYSA-N 0.000 description 1
- UPSNOKIUEULXHF-UHFFFAOYSA-N n-chloropropanamide Chemical compound CCC(=O)NCl UPSNOKIUEULXHF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000005949 ozonolysis reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
- CLZWAWBPWVRRGI-UHFFFAOYSA-N tert-butyl 2-[2-[2-[2-[bis[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]-5-bromophenoxy]ethoxy]-4-methyl-n-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]anilino]acetate Chemical compound CC1=CC=C(N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)C(OCCOC=2C(=CC=C(Br)C=2)N(CC(=O)OC(C)(C)C)CC(=O)OC(C)(C)C)=C1 CLZWAWBPWVRRGI-UHFFFAOYSA-N 0.000 description 1
- MSMMJZIQVFTCPP-UHFFFAOYSA-N tert-butyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound O=C1N(C(C(=C)C)C(=O)OC(C)(C)C)C(S(Cl)=O)C1NC(=O)COC1=CC=CC=C1 MSMMJZIQVFTCPP-UHFFFAOYSA-N 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
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/696,674 US4075203A (en) | 1976-06-16 | 1976-06-16 | Process for preparing a 3-exomethylenecepham sulfoxide from penicillin sulfoxides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2726394A1 DE2726394A1 (de) | 1977-12-29 |
| DE2726394C2 true DE2726394C2 (en, 2012) | 1990-03-15 |
Family
ID=24798089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772726394 Granted DE2726394A1 (de) | 1976-06-16 | 1977-06-10 | Verfahren zur herstellung von 2-chlorsulfinylazetidin-4-onen |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4075203A (en, 2012) |
| JP (1) | JPS6043339B2 (en, 2012) |
| AR (1) | AR219926A1 (en, 2012) |
| AT (1) | AT352138B (en, 2012) |
| AU (1) | AU508748B2 (en, 2012) |
| BE (1) | BE855694A (en, 2012) |
| CA (1) | CA1083579A (en, 2012) |
| CH (1) | CH627161A5 (en, 2012) |
| CS (1) | CS198246B2 (en, 2012) |
| DD (1) | DD131018A5 (en, 2012) |
| DE (1) | DE2726394A1 (en, 2012) |
| DK (1) | DK264577A (en, 2012) |
| ES (1) | ES459838A1 (en, 2012) |
| FR (1) | FR2355005A1 (en, 2012) |
| GB (1) | GB1584105A (en, 2012) |
| HU (1) | HU179966B (en, 2012) |
| IE (1) | IE45195B1 (en, 2012) |
| IL (1) | IL52117A (en, 2012) |
| NL (1) | NL189609C (en, 2012) |
| NZ (1) | NZ184136A (en, 2012) |
| PH (1) | PH13001A (en, 2012) |
| PL (1) | PL103103B1 (en, 2012) |
| PT (1) | PT66642B (en, 2012) |
| RO (1) | RO71066A (en, 2012) |
| SE (1) | SE438329B (en, 2012) |
| YU (1) | YU143177A (en, 2012) |
| ZA (1) | ZA772907B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138553A (en) * | 1976-11-11 | 1979-02-06 | Teijin Limited | 3-Methylene cephalosporanic acid derivatives and process for preparation thereof |
| US4159272A (en) * | 1977-09-01 | 1979-06-26 | Eli Lilly And Company | Process for 2-chlorosulfinylazetidin-4-ones |
| US4289695A (en) * | 1978-11-13 | 1981-09-15 | Eli Lilly And Company | Process for preparing 2-chlorosulfinylazetidinones |
| US5126446A (en) * | 1991-01-04 | 1992-06-30 | Eli Lilly And Company | Process for 3-exomethylenecepham sulfoxide esters |
| US5350845A (en) * | 1992-04-08 | 1994-09-27 | Eli Lilly And Company | Process for preparing 7-substituted-amino-3-hydroxy-3-cephem-4-protected carboxy-sulfoxide esters |
| US5347000A (en) * | 1992-11-05 | 1994-09-13 | Ranbaxy Laboratories Ltd. | Process for the preparation of 2-chlorosulfinylazetidinone |
| US5604222A (en) * | 1993-12-27 | 1997-02-18 | Lupin Laboratories, Ltd. | Method for the preparation of 2-chloro sulfinyl azetidinones |
| US5578721A (en) * | 1994-07-11 | 1996-11-26 | Lupin Laboratories Limited | Process for preparation of 3-exomethylene cepham sulfoxide esters |
| US6116362A (en) * | 1998-07-09 | 2000-09-12 | Case Corporation | Articulated vehicle |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS551272B2 (en, 2012) * | 1972-04-14 | 1980-01-12 | ||
| US3843682A (en) * | 1972-05-15 | 1974-10-22 | Lilly Co Eli | 2-chlorosulfinyl-3-imido-azetedin-4-ones |
| GB1442785A (en) * | 1972-12-09 | 1976-07-14 | Nikken Chemicals Co Ltd | Desacetoxy ceaphalosporanic acids |
| NL7411505A (nl) * | 1973-09-06 | 1975-03-10 | Rhone Poulenc Sa | Werkwijze voor de bereiding en toepassing van nieuwe 7-trichlooraceetamido-3-desacetoxy-cefa- losporanzuurpreparaten. |
| CA1069126A (en) * | 1974-12-24 | 1980-01-01 | Eli Lilly And Company | Sulfinyl halides and their preparation from penicillin sulfoxides |
-
1976
- 1976-06-16 US US05/696,674 patent/US4075203A/en not_active Expired - Lifetime
-
1977
- 1977-05-13 CA CA278,389A patent/CA1083579A/en not_active Expired
- 1977-05-16 ZA ZA00772907A patent/ZA772907B/xx unknown
- 1977-05-16 IE IE996/77A patent/IE45195B1/en not_active IP Right Cessation
- 1977-05-18 IL IL52117A patent/IL52117A/xx unknown
- 1977-05-18 NZ NZ184136A patent/NZ184136A/xx unknown
- 1977-05-24 AU AU25427/77A patent/AU508748B2/en not_active Expired
- 1977-06-06 PT PT66642A patent/PT66642B/pt unknown
- 1977-06-09 YU YU01431/77A patent/YU143177A/xx unknown
- 1977-06-09 GB GB24262/77A patent/GB1584105A/en not_active Expired
- 1977-06-10 PH PH19871A patent/PH13001A/en unknown
- 1977-06-10 DE DE19772726394 patent/DE2726394A1/de active Granted
- 1977-06-15 BE BE1008193A patent/BE855694A/xx not_active IP Right Cessation
- 1977-06-15 HU HU77EI747A patent/HU179966B/hu unknown
- 1977-06-15 SE SE7706948A patent/SE438329B/xx not_active IP Right Cessation
- 1977-06-15 AR AR268068A patent/AR219926A1/es active
- 1977-06-15 PL PL1977198878A patent/PL103103B1/pl unknown
- 1977-06-15 DK DK264577A patent/DK264577A/da not_active Application Discontinuation
- 1977-06-15 CS CS773959A patent/CS198246B2/cs unknown
- 1977-06-15 JP JP52071548A patent/JPS6043339B2/ja not_active Expired
- 1977-06-15 CH CH737877A patent/CH627161A5/de not_active IP Right Cessation
- 1977-06-15 RO RO7790694A patent/RO71066A/ro unknown
- 1977-06-15 AT AT423777A patent/AT352138B/de not_active IP Right Cessation
- 1977-06-15 NL NLAANVRAGE7706604,A patent/NL189609C/xx not_active IP Right Cessation
- 1977-06-16 DD DD7700199521A patent/DD131018A5/xx unknown
- 1977-06-16 FR FR7718551A patent/FR2355005A1/fr active Granted
- 1977-06-16 ES ES459838A patent/ES459838A1/es not_active Expired
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