DD146457A5 - Verfahren zur herstellung von 3-exomethylencephamsulfoxiden - Google Patents

Verfahren zur herstellung von 3-exomethylencephamsulfoxiden Download PDF

Info

Publication number: DD146457A5
Authority: DD; German Democratic Republic
Prior art keywords: oxo; complex; compound; carbon atoms; methyl
Prior art date: 1978-11-13

Application number

DD79216204A

Other languages

German (de)

English (en)

Inventor

Ta-Sen Chou

Original Assignee

Lilly Co Eli

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-11-13

Filing date

1979-10-12

Publication date

1981-02-11

1979-10-12 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1981-02-11 Publication of DD146457A5 publication Critical patent/DD146457A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 47
230000008569 process Effects 0.000 title claims abstract description 40
238000002360 preparation method Methods 0.000 title claims abstract description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 57
150000001875 compounds Chemical class 0.000 claims abstract description 26
-1 oxo compound Chemical class 0.000 claims description 50
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 16
229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 16
239000001119 stannous chloride Substances 0.000 claims description 16
235000011150 stannous chloride Nutrition 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
KDXFMMHNGFNJFA-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinyl chloride Chemical compound ClS(=O)C1CC(=O)N1 KDXFMMHNGFNJFA-UHFFFAOYSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 2
229910052736 halogen Chemical group 0.000 claims description 2
229920000075 poly(4-vinylpyridine) Polymers 0.000 abstract description 10
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 abstract description 8
HUEZUDXJCGHIHG-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1.C=CC1=CC=CC=C1C=C HUEZUDXJCGHIHG-UHFFFAOYSA-N 0.000 abstract description 7
239000000543 intermediate Substances 0.000 abstract description 5
229930186147 Cephalosporin Natural products 0.000 abstract description 2
229940124587 cephalosporin Drugs 0.000 abstract description 2
150000001780 cephalosporins Chemical class 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000000725 suspension Substances 0.000 description 25
239000000047 product Substances 0.000 description 21
238000007363 ring formation reaction Methods 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
238000003756 stirring Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000003446 ligand Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000007858 starting material Substances 0.000 description 8
229920001577 copolymer Polymers 0.000 description 7
238000004132 cross linking Methods 0.000 description 7
229910052718 tin Inorganic materials 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
150000003952 β-lactams Chemical class 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000007787 solid Substances 0.000 description 5
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 5
IZYJOLMJKGBANZ-UHFFFAOYSA-N 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoic acid Chemical compound O=C1N(C(C(=C)C)C(O)=O)C(S(Cl)=O)C1NC(=O)COC1=CC=CC=C1 IZYJOLMJKGBANZ-UHFFFAOYSA-N 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000007788 liquid Substances 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical class N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000005727 Friedel-Crafts reaction Methods 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000005215 alkyl ethers Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
WNMFNGGUHIIQJE-BEZSAJEZSA-N (4-nitrophenyl)methyl (5r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4$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 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
PVEOYINWKBTPIZ-UHFFFAOYSA-M but-3-enoate Chemical compound [O-]C(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-M 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
150000003004 phosphinoxides Chemical class 0.000 description 2
229920002717 polyvinylpyridine Polymers 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
MMKTVJMEPOTLJS-UHFFFAOYSA-N (4-methoxyphenyl)methyl 2-[2-chlorosulfinyl-3-[(2-cyanoacetyl)amino]-4-oxoazetidin-1-yl]-3-methylbut-3-enoate Chemical compound C1=CC(OC)=CC=C1COC(=O)C(C(C)=C)N1C(=O)C(NC(=O)CC#N)C1S(Cl)=O MMKTVJMEPOTLJS-UHFFFAOYSA-N 0.000 description 1
CLUKTSIUGTWYPH-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-(2-chlorosulfinyl-3-formamido-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N1C(S(Cl)=O)C(NC=O)C1=O CLUKTSIUGTWYPH-UHFFFAOYSA-N 0.000 description 1
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
OAZLXJCFUYYYGO-ZCFIWIBFSA-N (6r)-3-chloro-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC(Cl)=CN2C(=O)C[C@H]21 OAZLXJCFUYYYGO-ZCFIWIBFSA-N 0.000 description 1
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QVKXFHZXOLIUKV-UHFFFAOYSA-N 1-bis(4-bromophenyl)phosphoryl-4-bromobenzene Chemical compound C1=CC(Br)=CC=C1P(=O)(C=1C=CC(Br)=CC=1)C1=CC=C(Br)C=C1 QVKXFHZXOLIUKV-UHFFFAOYSA-N 0.000 description 1
GJBIMMKVOGMMLP-UHFFFAOYSA-N 1-bis(4-chlorophenyl)phosphoryl-4-chlorobenzene Chemical compound C1=CC(Cl)=CC=C1P(=O)(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 GJBIMMKVOGMMLP-UHFFFAOYSA-N 0.000 description 1
SPKBYIYIZQARNX-UHFFFAOYSA-N 1-bis(4-methylphenyl)phosphoryl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1P(=O)(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 SPKBYIYIZQARNX-UHFFFAOYSA-N 0.000 description 1
MNZAKDODWSQONA-UHFFFAOYSA-N 1-dibutylphosphorylbutane Chemical compound CCCCP(=O)(CCCC)CCCC MNZAKDODWSQONA-UHFFFAOYSA-N 0.000 description 1
ZSSWXNPRLJLCDU-UHFFFAOYSA-N 1-diethylphosphorylethane Chemical compound CCP(=O)(CC)CC ZSSWXNPRLJLCDU-UHFFFAOYSA-N 0.000 description 1
SNZSAFILJOCMFM-UHFFFAOYSA-N 1-dipropylphosphorylpropane Chemical compound CCCP(=O)(CCC)CCC SNZSAFILJOCMFM-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
HTDVVRGHONTQMQ-UHFFFAOYSA-N 2,2,2-trichloroethyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenylacetyl)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)CC1=CC=CC=C1 HTDVVRGHONTQMQ-UHFFFAOYSA-N 0.000 description 1
ZVJBCWPFMGPOJP-UHFFFAOYSA-N 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methyl-2-[(4-nitrophenyl)methyl]but-3-enoic acid Chemical compound CC(=C)C(CC1=CC=C(C=C1)[N+](=O)[O-])(C(=O)O)N2C(C(C2=O)NC(=O)CC3=CC=CC=C3)S(=O)Cl ZVJBCWPFMGPOJP-UHFFFAOYSA-N 0.000 description 1
RSOHEDAICGZUEG-UHFFFAOYSA-N 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenylacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoic acid Chemical compound O=C1N(C(C(=C)C)C(O)=O)C(S(Cl)=O)C1NC(=O)CC1=CC=CC=C1 RSOHEDAICGZUEG-UHFFFAOYSA-N 0.000 description 1
FVNIMHIOIXPIQT-UHFFFAOYSA-N 2-methoxybutane Chemical compound CCC(C)OC FVNIMHIOIXPIQT-UHFFFAOYSA-N 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
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
XISLEOYIFRZKLT-UHFFFAOYSA-N 3,4-diethylcyclopentan-1-one Chemical compound CCC1CC(=O)CC1CC XISLEOYIFRZKLT-UHFFFAOYSA-N 0.000 description 1
MSANHHHQJYQEOK-UHFFFAOYSA-N 3,5-dimethylcyclohexan-1-one Chemical compound CC1CC(C)CC(=O)C1 MSANHHHQJYQEOK-UHFFFAOYSA-N 0.000 description 1
VZXXYILNWWRSGE-UHFFFAOYSA-N 3,5-dimethylheptan-4-one Chemical compound CCC(C)C(=O)C(C)CC VZXXYILNWWRSGE-UHFFFAOYSA-N 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 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
KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 description 1
101100472050 Caenorhabditis elegans rpl-2 gene Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
229910008433 SnCU Inorganic materials 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
BKFUENCFIROSHT-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(CC(C(=O)O)(C(=C)C)N2C(C(C2=O)NC(COC2=CC=CC=C2)=O)S(=O)Cl)C=C1.S(=O)(Cl)Cl Chemical compound [N+](=O)([O-])C1=CC=C(CC(C(=O)O)(C(=C)C)N2C(C(C2=O)NC(COC2=CC=CC=C2)=O)S(=O)Cl)C=C1.S(=O)(Cl)Cl BKFUENCFIROSHT-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
AONVTQGGKRUCBY-UHFFFAOYSA-N benzyl 2-(3-acetamido-2-chlorosulfinyl-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound O=C1C(NC(=O)C)C(S(Cl)=O)N1C(C(C)=C)C(=O)OCC1=CC=CC=C1 AONVTQGGKRUCBY-UHFFFAOYSA-N 0.000 description 1
MFWNIMMHWNHWEG-UHFFFAOYSA-N benzyl 2-(3-benzamido-2-chlorosulfinyl-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound C=1C=CC=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(Cl)=O)C1NC(=O)C1=CC=CC=C1 MFWNIMMHWNHWEG-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000004067 bulking agent Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
235000019219 chocolate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical class C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 description 1
CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical class O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000007257 deesterification reaction Methods 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
LEFPWWWXFFNJAA-UHFFFAOYSA-N dicyclohexylphosphorylcyclohexane Chemical compound C1CCCCC1P(C1CCCCC1)(=O)C1CCCCC1 LEFPWWWXFFNJAA-UHFFFAOYSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
LRMLWYXJORUTBG-UHFFFAOYSA-N dimethylphosphorylmethane Chemical compound CP(C)(C)=O LRMLWYXJORUTBG-UHFFFAOYSA-N 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
230000006872 improvement Effects 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical class O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
150000003462 sulfoxides Chemical class 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
UUEMPIARZQMASG-UHFFFAOYSA-N tert-butyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenylacetyl)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)CC1=CC=CC=C1 UUEMPIARZQMASG-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
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/02—Preparation
- C07D501/08—Preparation by forming the ring or condensed ring systems
- 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)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Cephalosporin Compounds (AREA)

DD79216204A 1978-11-13 1979-10-12 Verfahren zur herstellung von 3-exomethylencephamsulfoxiden DD146457A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/960,346 US4190724A (en)	1978-11-13	1978-11-13	Process for 3-exomethylenecepham sulfoxides

Publications (1)

Publication Number	Publication Date
DD146457A5 true DD146457A5 (de)	1981-02-11

Family

ID=25503071

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79216204A DD146457A5 (de)	1978-11-13	1979-10-12	Verfahren zur herstellung von 3-exomethylencephamsulfoxiden

Country Status (33)

Country	Link
US (1)	US4190724A (ko)
EP (1)	EP0011369B1 (ko)
JP (1)	JPS5566590A (ko)
KR (1)	KR830001591B1 (ko)
AR (1)	AR225421A1 (ko)
AT (1)	ATA663779A (ko)
AU (1)	AU5147779A (ko)
BE (1)	BE879210A (ko)
BG (1)	BG30628A3 (ko)
CA (1)	CA1150240A (ko)
CH (1)	CH640537A5 (ko)
CS (1)	CS209824B2 (ko)
DD (1)	DD146457A5 (ko)
DE (1)	DE2962353D1 (ko)
DK (1)	DK431479A (ko)
ES (1)	ES484917A0 (ko)
FI (1)	FI793094A (ko)
FR (1)	FR2440952A1 (ko)
GB (1)	GB2034702B (ko)
GR (1)	GR73094B (ko)
HU (1)	HU180745B (ko)
IE (1)	IE48964B1 (ko)
IL (1)	IL58406A (ko)
IS (1)	IS1041B6 (ko)
LU (1)	LU81769A1 (ko)
MA (1)	MA18605A1 (ko)
MW (1)	MW2979A1 (ko)
NO (1)	NO793271L (ko)
OA (1)	OA06355A (ko)
PL (1)	PL117584B1 (ko)
PT (1)	PT70263A (ko)
ZA (1)	ZA795242B (ko)
ZM (1)	ZM8379A1 (ko)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5832884A (ja) *	1981-08-20	1983-02-25	Otsuka Chem Co Ltd	３−エキソメチレンセフアム誘導体の製造方法
FI103048B (fi) *	1989-03-22	1999-04-15	Dsm Nv	Menetelmä 3-eksometyleenikefaamisulfoksidijohdannaisten valmistamiseks i
US4950753A (en) *	1989-05-17	1990-08-21	Eli Lilly And Company	Process for 3-exomethylenecepham sulfoxide esters
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
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

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3843682A (en) *	1972-05-15	1974-10-22	Lilly Co Eli	2-chlorosulfinyl-3-imido-azetedin-4-ones
US4052387A (en) *	1974-12-24	1977-10-04	Eli Lilly And Company	Method of preparation of 3-methylenecephams
CA1069126A (en) *	1974-12-24	1980-01-01	Eli Lilly And Company	Sulfinyl halides and their preparation from penicillin sulfoxides
GR59922B (en) *	1974-12-24	1978-03-20	Lilly Co Eli	Process for preparing 3-methylene cepham
US4375397A (en) *	1976-03-15	1983-03-01	E. R. Squibb & Sons, Inc.	Process for preparing 3-methylene cephalosporins

1978
- 1978-11-13 US US05/960,346 patent/US4190724A/en not_active Expired - Lifetime
1979
- 1979-10-02 ZA ZA00795242A patent/ZA795242B/xx unknown
- 1979-10-02 MA MA18805A patent/MA18605A1/fr unknown
- 1979-10-02 PT PT70263A patent/PT70263A/pt unknown
- 1979-10-04 AU AU51477/79A patent/AU5147779A/en not_active Abandoned
- 1979-10-04 FR FR7924712A patent/FR2440952A1/fr active Granted
- 1979-10-05 MW MW29/79A patent/MW2979A1/xx unknown
- 1979-10-05 BE BE1/9551A patent/BE879210A/fr not_active IP Right Cessation
- 1979-10-05 FI FI793094A patent/FI793094A/fi not_active Application Discontinuation
- 1979-10-05 IL IL58406A patent/IL58406A/xx unknown
- 1979-10-08 GR GR60217A patent/GR73094B/el unknown
- 1979-10-08 BG BG7945077A patent/BG30628A3/xx unknown
- 1979-10-09 DE DE7979302151T patent/DE2962353D1/de not_active Expired
- 1979-10-09 GB GB7935061A patent/GB2034702B/en not_active Expired
- 1979-10-09 EP EP79302151A patent/EP0011369B1/en not_active Expired
- 1979-10-09 ZM ZM83/79A patent/ZM8379A1/xx unknown
- 1979-10-10 ES ES484917A patent/ES484917A0/es active Granted
- 1979-10-10 LU LU81769A patent/LU81769A1/fr unknown
- 1979-10-10 CA CA000337271A patent/CA1150240A/en not_active Expired
- 1979-10-10 AR AR278436A patent/AR225421A1/es active
- 1979-10-11 AT AT663779A patent/ATA663779A/de not_active Application Discontinuation
- 1979-10-11 NO NO793271A patent/NO793271L/no unknown
- 1979-10-12 CH CH923979A patent/CH640537A5/fr not_active IP Right Cessation
- 1979-10-12 DK DK431479A patent/DK431479A/da unknown
- 1979-10-12 HU HU79EI883A patent/HU180745B/hu unknown
- 1979-10-12 PL PL1979218930A patent/PL117584B1/pl unknown
- 1979-10-12 JP JP13278479A patent/JPS5566590A/ja active Granted
- 1979-10-12 DD DD79216204A patent/DD146457A5/de unknown
- 1979-10-12 IE IE1941/79A patent/IE48964B1/en not_active IP Right Cessation
- 1979-10-12 CS CS796949A patent/CS209824B2/cs unknown
- 1979-10-13 KR KR1019790003526A patent/KR830001591B1/ko active
- 1979-10-13 OA OA56915A patent/OA06355A/xx unknown
- 1979-10-15 IS IS2515A patent/IS1041B6/is unknown

Also Published As

Publication number	Publication date
JPS5566590A (en)	1980-05-20
ES8101608A1 (es)	1980-12-16
IS1041B6 (is)	1980-11-25
EP0011369A1 (en)	1980-05-28
GB2034702A (en)	1980-06-11
CS209824B2 (en)	1981-12-31
FR2440952B1 (ko)	1983-02-25
CA1150240A (en)	1983-07-19
BG30628A3 (en)	1981-07-15
NO793271L (no)	1980-05-14
BE879210A (fr)	1980-04-08
JPH0127075B2 (ko)	1989-05-26
IL58406A (en)	1982-08-31
MA18605A1 (fr)	1980-07-01
PT70263A (en)	1979-11-01
KR830001292A (ko)	1983-04-30
AU5147779A (en)	1980-05-22
IE48964B1 (en)	1985-06-26
CH640537A5 (fr)	1984-01-13
PL117584B1 (en)	1981-08-31
ZM8379A1 (en)	1981-02-23
ES484917A0 (es)	1980-12-16
ATA663779A (de)	1981-04-15
GB2034702B (en)	1983-03-23
US4190724A (en)	1980-02-26
PL218930A1 (ko)	1980-06-16
IE791941L (en)	1980-05-13
FR2440952A1 (fr)	1980-06-06
LU81769A1 (fr)	1980-01-24
DK431479A (da)	1980-05-14
AR225421A1 (es)	1982-03-31
MW2979A1 (en)	1981-04-08
FI793094A (fi)	1980-05-14
OA06355A (fr)	1981-06-30
IL58406A0 (en)	1980-01-31
GR73094B (ko)	1984-02-01
EP0011369B1 (en)	1982-03-24
DE2962353D1 (en)	1982-04-29
ZA795242B (en)	1981-05-27
HU180745B (en)	1983-04-29
IS2515A7 (is)	1980-05-14
KR830001591B1 (ko)	1983-08-16

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DE2434208A1 (de)	1975-02-13	Derivat der 2-azetidinsulfensaeure und verfahren zu seiner herstellung
DE2953954C2 (ko)	1987-12-03
DE526168C (de)	1931-06-17	Verfahren zur Darstellung von Verbindungen mit hydrierten Ringsystemen
DD146457A5 (de)	1981-02-11	Verfahren zur herstellung von 3-exomethylencephamsulfoxiden
DE2519480A1 (de)	1975-11-13	Aryl-oxo-heptensaeuren
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EP0019872B1 (de)	1982-06-16	Verfahren zur Herstellung von Benzoxanthen- und Benzothioxanthenfarbstoffen
DE2557003A1 (de)	1977-06-23	Neue cyanessigsaeureanilid-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel
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DE2440745C3 (de)	1977-02-03	Verfahren zur Abtrennung von cis-Chrysanthemummonocarbonsäure
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DE10332684B3 (de)	2005-04-21	Verfahren zur Herstellung von Bifonazol
EP0026343B1 (de)	1983-06-22	Verfahren zur Herstellung von Bis-benzofuranyl-Verbindungen
LU86853A1 (de)	1987-08-12	Neue 8-beziehungsweise 1,8-substituierte ergolenderivate und verfahren zu ihrer herstellung
DE2360202A1 (de)	1974-06-06	Verfahren zur herstellung von benzothiazolen
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