CS241091B2 - Method of 2-heterocycloalkylthiopenemderivatives production - Google Patents

Method of 2-heterocycloalkylthiopenemderivatives production Download PDF

Info

Publication number: CS241091B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; compound; imidazolyl; solution; starting materials
Prior art date: 1983-07-14

Application number

CS845489A

Other languages

Czech (cs)

English (en)

Other versions

CS548984A2 (en

Inventor

Ernest S Hamanaka

Original Assignee

Pfizer

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.)

1983-07-14

Filing date

1984-07-16

Publication date

1986-03-13

1984-07-16 Application filed by Pfizer filed Critical Pfizer

1985-06-13 Publication of CS548984A2 publication Critical patent/CS548984A2/cs

1986-03-13 Publication of CS241091B2 publication Critical patent/CS241091B2/cs

Links

238000000034 method Methods 0.000 title claims description 23
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 65
-1 4-imidazolyl Chemical group 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 34
238000002360 preparation method Methods 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 19
239000007858 starting material Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
239000000243 solution Substances 0.000 description 60
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 29
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 21
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
238000002329 infrared spectrum Methods 0.000 description 9
239000000047 product Substances 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
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 8
239000003054 catalyst Substances 0.000 description 8
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 8
239000011734 sodium Substances 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
239000007864 aqueous solution Substances 0.000 description 7
239000012442 inert solvent Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
125000000217 alkyl group Chemical group 0.000 description 6
229960001701 chloroform Drugs 0.000 description 6
239000012043 crude product Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
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 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
239000011591 potassium Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
150000003573 thiols Chemical class 0.000 description 5
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
239000005909 Kieselgur Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000007327 hydrogenolysis reaction Methods 0.000 description 4
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 4
239000003826 tablet Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000008272 agar Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000004703 alkoxides Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
159000000007 calcium salts Chemical class 0.000 description 3
150000004649 carbonic acid derivatives Chemical class 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003462 sulfoxides Chemical group 0.000 description 3
238000012360 testing method Methods 0.000 description 3
GNYODRIBSWNASQ-PYMRYRCNSA-N (5r)-3-ethylsulfinyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(S(=O)CC)=C(C(O)=O)N2C(=O)C[C@H]21 GNYODRIBSWNASQ-PYMRYRCNSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 2
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
RKNYXMGZDWMOGZ-ZCFIWIBFSA-N O-methyl (5R)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carbothioate Chemical compound COC(=S)C1=CS[C@H]2N1C(C2)=O RKNYXMGZDWMOGZ-ZCFIWIBFSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000004108 freeze drying Methods 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
229910000510 noble metal Inorganic materials 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000002217 penem group Chemical group 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
125000005207 tetraalkylammonium group Chemical group 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000004665 trialkylsilyl group Chemical group 0.000 description 2
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
HIZCIEIDIFGZSS-UHFFFAOYSA-L trithiocarbonate Chemical compound [S-]C([S-])=S HIZCIEIDIFGZSS-UHFFFAOYSA-L 0.000 description 2
239000012989 trithiocarbonate Substances 0.000 description 2
CDQDMLWGTVLQEE-UHFFFAOYSA-N (1-methylimidazol-2-yl)methanol Chemical compound CN1C=CN=C1CO CDQDMLWGTVLQEE-UHFFFAOYSA-N 0.000 description 1
PDCNOQKFXQJARG-DHJUGAMNSA-N (4-nitrophenyl)methyl (5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-(2-imidazol-1-ylethylsulfanyl)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound O([Si](C)(C)C(C)(C)C)[C@H](C)[C@@H]1[C@@H]2N(C(=C(S2)SCCN2C=NC=C2)C(=O)OCC2=CC=C(C=C2)[N+](=O)[O-])C1=O PDCNOQKFXQJARG-DHJUGAMNSA-N 0.000 description 1
JESMSJZDKNVWNX-UHFFFAOYSA-N (4-nitrophenyl)methyl 2,2-dihydroxyacetate Chemical compound OC(O)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 JESMSJZDKNVWNX-UHFFFAOYSA-N 0.000 description 1
STDMSPQVWBOVAM-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-chloro-2-oxoacetate Chemical compound [O-][N+](=O)C1=CC=C(COC(=O)C(Cl)=O)C=C1 STDMSPQVWBOVAM-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JHSNSAFVQQRHAD-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)propan-2-ol Chemical compound CC(O)CC1=NC=CN1 JHSNSAFVQQRHAD-UHFFFAOYSA-N 0.000 description 1
YDCCNBOJCWQVDF-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)propan-2-yl 4-methylbenzenesulfonate Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)OC(C)CC1=NC=CN1 YDCCNBOJCWQVDF-UHFFFAOYSA-N 0.000 description 1
125000005848 1-(alkoxycarbonyloxy)ethyl group Chemical group 0.000 description 1
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
WCDFMPVITAWTGR-UHFFFAOYSA-N 1-imidazol-1-ylpropan-2-ol Chemical compound CC(O)CN1C=CN=C1 WCDFMPVITAWTGR-UHFFFAOYSA-N 0.000 description 1
CXSDOJZNGWCOBC-UHFFFAOYSA-N 1-methoxy-4-[(4-methoxyphenyl)methylsulfanylmethyl]benzene Chemical class C1=CC(OC)=CC=C1CSCC1=CC=C(OC)C=C1 CXSDOJZNGWCOBC-UHFFFAOYSA-N 0.000 description 1
AMSDWLOANMAILF-UHFFFAOYSA-N 2-imidazol-1-ylethanol Chemical compound OCCN1C=CN=C1 AMSDWLOANMAILF-UHFFFAOYSA-N 0.000 description 1
LNMBCRKRCIMQLW-UHFFFAOYSA-N 2-tert-butylsulfanyl-2-methylpropane Chemical class CC(C)(C)SC(C)(C)C LNMBCRKRCIMQLW-UHFFFAOYSA-N 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
FASMXPUFMXBVRL-UHFFFAOYSA-N 5-(chloromethyl)-1h-imidazole;hydron;chloride Chemical compound Cl.ClCC1=CN=CN1 FASMXPUFMXBVRL-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
IJDVYIUPBFUZKT-UHFFFAOYSA-N N1C(=NC=C1)C(C(=S)O)C Chemical compound N1C(=NC=C1)C(C(=S)O)C IJDVYIUPBFUZKT-UHFFFAOYSA-N 0.000 description 1
XCUYVZZAFNNCCK-SSDOTTSWSA-N O-ethyl (5R)-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carbothioate Chemical compound C(C)OC(=S)C1=CS[C@H]2N1C(C2)=O XCUYVZZAFNNCCK-SSDOTTSWSA-N 0.000 description 1
APTGPWJUOYMUCE-UHFFFAOYSA-N S-Ethyl thioacetate Chemical compound CCSC(C)=O APTGPWJUOYMUCE-UHFFFAOYSA-N 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005206 alkoxycarbonyloxymethyl group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000009635 antibiotic susceptibility testing Methods 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000005604 azodicarboxylate group Chemical group 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
HIZCIEIDIFGZSS-UHFFFAOYSA-N carbonotrithioic acid Chemical class SC(S)=S HIZCIEIDIFGZSS-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical class CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
125000005643 gamma-butyrolacton-4-yl group Chemical group 0.000 description 1
238000002523 gelfiltration Methods 0.000 description 1
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
AZBIYMNNHQEYJS-UHFFFAOYSA-N o-(2-imidazol-1-ylethyl) ethanethioate Chemical compound CC(=S)OCCN1C=CN=C1 AZBIYMNNHQEYJS-UHFFFAOYSA-N 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
238000007747 plating Methods 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
DWTKHSHPNIZEIS-UHFFFAOYSA-N s-[1-(1h-imidazol-2-yl)propan-2-yl] ethanethioate Chemical compound CC(=O)SC(C)CC1=NC=CN1 DWTKHSHPNIZEIS-UHFFFAOYSA-N 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000017105 transposition Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
150000003952 β-lactams Chemical group 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS845489A 1983-07-14 1984-07-16 Method of 2-heterocycloalkylthiopenemderivatives production CS241091B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US51356983A	1983-07-14	1983-07-14

Publications (2)

Publication Number	Publication Date
CS548984A2 CS548984A2 (en)	1985-06-13
CS241091B2 true CS241091B2 (en)	1986-03-13

Family

ID=24043826

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS845489A CS241091B2 (en)	1983-07-14	1984-07-16	Method of 2-heterocycloalkylthiopenemderivatives production

Country Status (11)

Country	Link
JP (1)	JPS6051192A (de)
KR (1)	KR850001217A (de)
CS (1)	CS241091B2 (de)
DD (1)	DD226290A5 (de)
ES (1)	ES8602808A1 (de)
FI (1)	FI842833A7 (de)
HU (1)	HUT34490A (de)
NO (1)	NO842882L (de)
PL (1)	PL248728A1 (de)
PT (1)	PT78873B (de)
ZA (1)	ZA845421B (de)

1984
- 1984-07-10 PT PT78873A patent/PT78873B/pt unknown
- 1984-07-11 ES ES534223A patent/ES8602808A1/es not_active Expired
- 1984-07-13 KR KR1019840004122A patent/KR850001217A/ko not_active Ceased
- 1984-07-13 HU HU842752A patent/HUT34490A/hu unknown
- 1984-07-13 NO NO842882A patent/NO842882L/no unknown
- 1984-07-13 JP JP59145897A patent/JPS6051192A/ja active Pending
- 1984-07-13 DD DD84265267A patent/DD226290A5/de unknown
- 1984-07-13 ZA ZA845421A patent/ZA845421B/xx unknown
- 1984-07-13 FI FI842833A patent/FI842833A7/fi not_active Application Discontinuation
- 1984-07-13 PL PL24872884A patent/PL248728A1/xx unknown
- 1984-07-16 CS CS845489A patent/CS241091B2/cs unknown

Also Published As

Publication number	Publication date
FI842833A7 (fi)	1985-01-15
JPS6051192A (ja)	1985-03-22
ES534223A0 (es)	1985-12-01
HUT34490A (en)	1985-03-28
PT78873B (en)	1986-10-23
DD226290A5 (de)	1985-08-21
ZA845421B (en)	1986-02-26
ES8602808A1 (es)	1985-12-01
KR850001217A (ko)	1985-03-16
PL248728A1 (en)	1985-04-09
CS548984A2 (en)	1985-06-13
FI842833A0 (fi)	1984-07-13
PT78873A (en)	1984-08-01
NO842882L (no)	1985-01-15

Publication	Publication Date	Title
US4619924A (en)	1986-10-28	2-alkylthiopenem derivatives
EP0294934B1 (de)	1996-01-10	Diastereomere 5R,6S-6-(1R-hydroxyethyl)-2-(Cis-1-oxo-3-thiolanylthio)-2-Penem-3-Carbonsäuren
US5459260A (en)	1995-10-17	Tricyclic or tetracyclic carbapenem compounds, their production and use
US4155912A (en)	1979-05-22	2-Methylpenem-3-carboxylic acid antibiotics
EP0130025B1 (de)	1987-07-08	2-Alkylthiopenem-Derivate
EP0138538B1 (de)	1988-12-14	2-Dioxacycloalkylthiopenem-Derivate
US4772597A (en)	1988-09-20	2-azacycloalkylthiopenem derivatives
FI82250B (fi)	1990-10-31	Foerfarande foer framstaellning av terapeutiskt aktiva 6-(1-hydroxietyl)-2-azacykloalkyl(alkylen)tio- 2-penem-3-karboxylsyrafoereningarna.
CS241091B2 (en)	1986-03-13	Method of 2-heterocycloalkylthiopenemderivatives production
EP0132101A1 (de)	1985-01-23	2-Heterocycloalkylthiopenem-Derivate
EP0260042B1 (de)	1991-12-27	2-(1-Oxo-1-imino-1-thiacycloalkyl)-Thiopenem-Derivate
FI81584B (fi)	1990-07-31	Foerfarande foer framstaellning av antibakteriella 6-alfa-hydroxietyl-2-substituerad-2-penem-3-karboxylsyror.
KR870000524B1 (ko)	1987-03-14	2-디옥사시클로알킬티오 페넴유도체의 제조방법
KR0128513B1 (ko)	1998-04-04	신규한 항균성 페넴 유도체와 그의 제조방법
PL150254B1 (de)	1990-05-31
EP0392681A1 (de)	1990-10-17	Antibakteriell wirkende 2-Carbapenem-Derivate