SE469630B - Karbapenem-antibiotika - Google Patents

Karbapenem-antibiotika

Info

Publication number: SE469630B
Authority: SE; Sweden
Prior art keywords: formula; methyl; group; protecting group; compound
Prior art date: 1985-09-11

Application number

SE8603798A

Other languages

English (en)

Swedish (sv)

Other versions

SE8603798L (sv

SE8603798D0 (sv

Inventor

A Martel

C Bachand

Original Assignee

Bristol Myers Squibb Co

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

1985-09-11

Filing date

1986-09-10

Publication date

1993-08-09

1986-09-10 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1986-09-10 Publication of SE8603798D0 publication Critical patent/SE8603798D0/xx

1987-03-12 Publication of SE8603798L publication Critical patent/SE8603798L/xx

1993-08-09 Publication of SE469630B publication Critical patent/SE469630B/sv

Links

239000003242 anti bacterial agent Substances 0.000 title description 10
229940088710 antibiotic agent Drugs 0.000 title description 8
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 61
125000006239 protecting group Chemical group 0.000 claims description 35
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
239000003960 organic solvent Substances 0.000 claims description 16
150000002148 esters Chemical class 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 10
239000002168 alkylating agent Substances 0.000 claims description 6
229940100198 alkylating agent Drugs 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 5
239000000741 silica gel Substances 0.000 claims description 5
229910002027 silica gel Inorganic materials 0.000 claims description 5
239000012442 inert solvent Substances 0.000 claims description 4
238000005956 quaternization reaction Methods 0.000 claims description 4
239000003480 eluent Substances 0.000 claims description 3
150000003952 β-lactams Chemical class 0.000 claims description 3
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 claims description 2
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
238000004366 reverse phase liquid chromatography Methods 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
241000735552 Erythroxylum Species 0.000 claims 2
235000008957 cocaer Nutrition 0.000 claims 2
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
239000006177 biological buffer Substances 0.000 claims 1
238000002474 experimental method Methods 0.000 claims 1
238000004128 high performance liquid chromatography Methods 0.000 claims 1
150000003573 thiols Chemical class 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
-1 cycloalkenylalkyl Chemical group 0.000 description 32
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
239000000543 intermediate Substances 0.000 description 31
BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
125000004432 carbon atom Chemical group C* 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
125000003396 thiol group Chemical class [H]S* 0.000 description 14
125000000217 alkyl group Chemical group 0.000 description 13
125000003118 aryl group Chemical group 0.000 description 13
125000000623 heterocyclic group Chemical group 0.000 description 13
239000000243 solution Substances 0.000 description 12
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
230000000694 effects Effects 0.000 description 7
125000001072 heteroaryl group Chemical group 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
125000001931 aliphatic group Chemical group 0.000 description 5
125000003342 alkenyl group Chemical group 0.000 description 5
125000004475 heteroaralkyl group Chemical group 0.000 description 5
150000002431 hydrogen Chemical group 0.000 description 5
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 5
239000007858 starting material Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
XUERKRUERHBPBL-UHFFFAOYSA-N 2-chloro-7-hydroxy-10,10-dimethyl-7-phenylpyrido[1,2-a]indole-6,8-dione Chemical compound O=C1N2C3=CC=C(Cl)C=C3C(C)(C)C2=CC(=O)C1(O)C1=CC=CC=C1 XUERKRUERHBPBL-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
101150054451 Rtel1 gene Proteins 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
125000000304 alkynyl group Chemical group 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 4
125000004415 heterocyclylalkyl group Chemical group 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
125000004434 sulfur atom Chemical group 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000011282 treatment Methods 0.000 description 4
210000002700 urine Anatomy 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 3
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 3
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
239000012223 aqueous fraction Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
238000009472 formulation Methods 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 3
QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
125000005633 phthalidyl group Chemical group 0.000 description 3
230000004962 physiological condition Effects 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
AHQTYUNPLZYCOL-UHFFFAOYSA-N 1,4-dioxane;ethanol;hydrate Chemical compound O.CCO.C1COCCO1 AHQTYUNPLZYCOL-UHFFFAOYSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007621 bhi medium Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
230000036765 blood level Effects 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
229940041011 carbapenems Drugs 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
125000004956 cyclohexylene group Chemical group 0.000 description 2
125000004979 cyclopentylene group Chemical group 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000029142 excretion Effects 0.000 description 2
238000007429 general method Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000007928 intraperitoneal injection Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
239000011630 iodine Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
150000002941 palladium compounds Chemical class 0.000 description 2
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 2
238000006303 photolysis reaction Methods 0.000 description 2
230000015843 photosynthesis, light reaction Effects 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
125000003367 polycyclic group Chemical group 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
238000003797 solvolysis reaction Methods 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-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
229910052725 zinc Inorganic materials 0.000 description 2
239000011701 zinc Substances 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 description 1
KUQSHRXUEGEMBF-UHFFFAOYSA-N (4-nitrophenyl)sulfonyl 4-nitrobenzenesulfonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 KUQSHRXUEGEMBF-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
BSUKKOMNQGNSGP-UHFFFAOYSA-N 2-ethylidenehexanoic acid Chemical compound CCCCC(=CC)C(O)=O BSUKKOMNQGNSGP-UHFFFAOYSA-N 0.000 description 1
125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
KXEAZJHCOWBLLF-UHFFFAOYSA-N 3-methyl-3-(3-methylpentan-3-yloxy)pentane Chemical compound CCC(C)(CC)OC(C)(CC)CC KXEAZJHCOWBLLF-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
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CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SE8603798A 1985-09-11 1986-09-10 Karbapenem-antibiotika SE469630B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/774,628 US4665169A (en)	1985-09-11	1985-09-11	Carbapenem antibiotics

Publications (3)

Publication Number	Publication Date
SE8603798D0 SE8603798D0 (sv)	1986-09-10
SE8603798L SE8603798L (sv)	1987-03-12
SE469630B true SE469630B (sv)	1993-08-09

Family

ID=25101800

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE8603798A SE469630B (sv)	1985-09-11	1986-09-10	Karbapenem-antibiotika

Country Status (31)

Country	Link
US (1)	US4665169A (de)
JP (1)	JPS6261980A (de)
KR (1)	KR910006807B1 (de)
CN (1)	CN1015261B (de)
AR (1)	AR242577A1 (de)
AT (1)	AT396472B (de)
AU (1)	AU596990B2 (de)
BE (1)	BE905415A (de)
CH (1)	CH669381A5 (de)
CS (1)	CS259892B2 (de)
DD (1)	DD252605A1 (de)
DE (1)	DE3630857C2 (de)
DK (1)	DK433586A (de)
ES (1)	ES2002303A6 (de)
FI (1)	FI81803C (de)
FR (1)	FR2587704B1 (de)
GB (1)	GB2180238B (de)
GR (1)	GR862313B (de)
HU (1)	HU198491B (de)
IL (1)	IL79969A0 (de)
IT (1)	IT1207578B (de)
LU (1)	LU86575A1 (de)
MY (1)	MY102957A (de)
NL (1)	NL8602282A (de)
NZ (1)	NZ217519A (de)
PT (1)	PT83361B (de)
SE (1)	SE469630B (de)
SU (1)	SU1480764A3 (de)
YU (1)	YU45800B (de)
ZA (1)	ZA866638B (de)
ZW (1)	ZW16186A1 (de)

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Publication number	Priority date	Publication date	Assignee	Title
MX20084A (es) *	1989-03-28	1993-03-01	Pfizer	Derivados de 2 -carbapenem antibacterianos
US5321020A (en) *	1989-03-28	1994-06-14	Pfizer Inc.	Antibacterial 2-carbapenem derivatives
US5602118A (en) *	1993-03-16	1997-02-11	American Cyanamid Company	2-thiosubstituted carbapenems
RU2714730C1 (ru)	2019-04-11	2020-02-19	Общество с ограниченной ответственностью "КС-ТЕХНОЛОГИИ"	Конусная инерционная дробилка с опорным подшипником скольжения

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US3950357A (en) *	1974-11-25	1976-04-13	Merck & Co., Inc.	Antibiotics
US4235920A (en) *	1975-11-21	1980-11-25	Merck & Co., Inc.	N-Alkylated derivatives of thienamycin
AU4061378A (en) *	1977-10-19	1980-04-17	Merck & Co., Inc.	1-azabicyclo (3.2.0) hept-2-enes
AU531084B2 (en) *	1977-10-19	1983-08-11	Merck & Co., Inc.	Azetidine derivatives
DE2966497D1 (en) *	1978-10-24	1984-01-26	Merck & Co Inc	6-, 1- and 2-substituted-1-carbapen-2-em-3-carboxylic acids, processes for the preparation of such compounds and pharmaceutical composition comprising such compounds
US4232036A (en) *	1978-10-24	1980-11-04	Merck & Co., Inc.	6-, 1- and 2-Substituted-1-carbadethiapen-2-em-3-carboxylic acids
EP0017992A1 (de) *	1979-04-19	1980-10-29	Merck & Co. Inc.	2-Substituierte-6-substituierte-1-Carbadethiapen-2-em-3-carbonsäuren, Verfahren zu ihrer Herstellung, sie enthaltende antibiotische pharmazeutische Zusammensetzungen und Verfahren zur Herstellung von Zwischenprodukten
US4376774A (en) *	1979-05-29	1983-03-15	Merck & Co., Inc.	Antibiotic N-heterocyclyl thienamycin
IE52147B1 (en) *	1980-03-27	1987-07-08	Merck & Co Inc	4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation
US4309346A (en) *	1980-03-27	1982-01-05	Merck & Co., Inc.	Process for the preparation of 1-carbapenems and intermediates via trithioorthoacetates
DE3169321D1 (en) *	1980-03-27	1985-04-25	Merck & Co Inc	Process for the preparation of 1-carbapenems and intermediates via silyl-substituted dithioacetals
EP0038869A1 (de) *	1980-04-30	1981-11-04	Merck & Co. Inc.	Verfahren zur Herstellung von 1-Carbapenemen und Zwischenprodukte für ihre Herstellung
JPS56161393A (en) *	1980-05-16	1981-12-11	Sanraku Inc	Beta-lactam compound
CA1198440A (en) *	1982-04-08	1985-12-24	Choung U. Kim	Carbapenem antibiotics
US4552696A (en) *	1982-04-09	1985-11-12	Bristol-Myers Company	Carbapenem antibiotics
US4536335A (en) *	1982-06-18	1985-08-20	Bristol-Myers Company	Carbapenem antibiotics
FI832619A (fi) *	1982-07-26	1984-01-27	Sandoz Ag	Fluoralkylerade karbapenemderivat
NZ205626A (en) *	1982-09-28	1986-12-05	Bristol Myers Co	Carbapenem antibiotics
DK140584A (da) *	1983-03-08	1984-09-09	Bristol Myers Co	Fremgangsmaade til fremstilling af carbapenemderivater
JPS60202886A (ja) *	1984-03-27	1985-10-14	Sankyo Co Ltd	１―置換カルバペネム―３―カルボン酸誘導体

1985
- 1985-09-11 US US06/774,628 patent/US4665169A/en not_active Expired - Fee Related
1986
- 1986-08-08 ZW ZW161/86A patent/ZW16186A1/xx unknown
- 1986-08-29 AR AR86305095A patent/AR242577A1/es active
- 1986-09-02 ZA ZA866638A patent/ZA866638B/xx unknown
- 1986-09-04 AU AU62348/86A patent/AU596990B2/en not_active Ceased
- 1986-09-08 FI FI863609A patent/FI81803C/fi not_active IP Right Cessation
- 1986-09-08 FR FR868612540A patent/FR2587704B1/fr not_active Expired
- 1986-09-08 IL IL79969A patent/IL79969A0/xx not_active IP Right Cessation
- 1986-09-09 CN CN86105933A patent/CN1015261B/zh not_active Expired
- 1986-09-09 DD DD86294267A patent/DD252605A1/de not_active IP Right Cessation
- 1986-09-09 NZ NZ217519A patent/NZ217519A/xx unknown
- 1986-09-10 DE DE3630857A patent/DE3630857C2/de not_active Expired - Fee Related
- 1986-09-10 IT IT8621666A patent/IT1207578B/it active
- 1986-09-10 GB GB8621759A patent/GB2180238B/en not_active Expired
- 1986-09-10 ES ES8601760A patent/ES2002303A6/es not_active Expired
- 1986-09-10 GR GR862313A patent/GR862313B/el unknown
- 1986-09-10 BE BE0/217150A patent/BE905415A/fr not_active IP Right Cessation
- 1986-09-10 LU LU86575A patent/LU86575A1/fr unknown
- 1986-09-10 KR KR1019860007583A patent/KR910006807B1/ko not_active Expired
- 1986-09-10 DK DK433586A patent/DK433586A/da not_active Application Discontinuation
- 1986-09-10 JP JP61213707A patent/JPS6261980A/ja active Pending
- 1986-09-10 SU SU864028122A patent/SU1480764A3/ru active
- 1986-09-10 CH CH3640/86A patent/CH669381A5/de not_active IP Right Cessation
- 1986-09-10 SE SE8603798A patent/SE469630B/sv not_active IP Right Cessation
- 1986-09-10 NL NL8602282A patent/NL8602282A/nl not_active Application Discontinuation
- 1986-09-11 YU YU158586A patent/YU45800B/sh unknown
- 1986-09-11 HU HU863916A patent/HU198491B/hu not_active IP Right Cessation
- 1986-09-11 CS CS866567A patent/CS259892B2/cs unknown
- 1986-09-11 PT PT83361A patent/PT83361B/pt not_active IP Right Cessation
- 1986-09-11 AT AT0245286A patent/AT396472B/de not_active IP Right Cessation
1987
- 1987-10-01 MY MYPI87002710A patent/MY102957A/en unknown

Also Published As

Publication number	Publication date
YU45800B (sh)	1992-07-20
CN86105933A (zh)	1987-05-20
AU6234886A (en)	1987-03-12
PT83361A (en)	1986-10-01
PT83361B (pt)	1989-05-12
NL8602282A (nl)	1987-04-01
DK433586D0 (da)	1986-09-10
ES2002303A6 (es)	1988-08-01
FI81803B (fi)	1990-08-31
FR2587704A1 (fr)	1987-03-27
FI863609L (fi)	1987-03-12
FI863609A0 (fi)	1986-09-08
DK433586A (da)	1987-03-12
BE905415A (fr)	1987-03-10
KR910006807B1 (ko)	1991-09-02
GR862313B (en)	1987-01-12
DD252605A1 (de)	1987-12-23
SU1480764A3 (ru)	1989-05-15
NZ217519A (en)	1990-07-26
MY102957A (en)	1993-03-31
LU86575A1 (fr)	1987-04-02
JPS6261980A (ja)	1987-03-18
SE8603798L (sv)	1987-03-12
KR870003110A (ko)	1987-04-15
ZW16186A1 (en)	1988-03-30
HU198491B (en)	1989-10-30
CH669381A5 (de)	1989-03-15
GB8621759D0 (en)	1986-10-15
AT396472B (de)	1993-09-27
US4665169A (en)	1987-05-12
FR2587704B1 (fr)	1989-02-24
FI81803C (fi)	1990-12-10
IL79969A0 (en)	1986-12-31
CN1015261B (zh)	1992-01-01
IT1207578B (it)	1989-05-25
DE3630857A1 (de)	1987-03-19
SE8603798D0 (sv)	1986-09-10
CS656786A2 (en)	1988-03-15
YU158586A (en)	1988-02-29
ATA245286A (de)	1993-01-15
IT8621666A0 (it)	1986-09-10
DE3630857C2 (de)	1994-04-07
GB2180238A (en)	1987-03-25
HUT42487A (en)	1987-07-28
CS259892B2 (en)	1988-11-15
AU596990B2 (en)	1990-05-24
ZA866638B (en)	1987-05-27
AR242577A1 (es)	1993-04-30
GB2180238B (en)	1989-09-06

Publication	Publication Date	Title
KR890001426B1 (ko)	1989-05-03	카르바페넴 화합물의 제조방법
CZ287296A3 (en)	1997-05-14	Cephalosporin antibiotics and antibacterial preparations in which they are comprised
US6489318B1 (en)	2002-12-03	Ethylidene derivatives of tricyclic carbapenems
NO167862B (no)	1991-09-09	Analogifremgangsmaate for fremstilling av terapeutisk aktivt(1r, 5s, 6s)-2-substituert tio-6-((r)-1-hydroksyetyl)-1-metyl-carbapenem-3-karboksylsyrederivat.
KR880001069B1 (ko)	1988-06-20	카르바페넴 유도체및 그의 제조방법
US5583218A (en)	1996-12-10	Carbapenem derivatives
US4374848A (en)	1983-02-22	6-(1-Hydroxyethyl)cyclonocardicin
SE469630B (sv)	1993-08-09	Karbapenem-antibiotika
HU191066B (en)	1987-01-28	Process for preparing carbapenem derivatives
EP0235823B1 (de)	1992-05-20	Carbapenem-Antibiotika, ein Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
US4880922A (en)	1989-11-14	Carbapenems with quaternized heterothioalkylthio substitution at position 2
HU192819B (en)	1987-07-28	Process for preparing antibacterial penemic derivatives
KR910009270B1 (ko)	1991-11-08	카바펜엠 항생제의 제조방법
SE460197B (sv)	1989-09-18	Nya karbapenemderivat och foerfarande foer framstaellning daerav
CA2338776C (en)	2008-04-29	Novel c-2 s/o- and s/n formaldehyde acetal derivatives of carbapenem-3-carboxylic acids and their use as antibiotics and .beta.-lactamase inhibitors
EP0430037A2 (de)	1991-06-05	Verfahren zur Herstellung von 2-Kohlenstoffsubstituierten Carbapenemderivaten
KR20010029454A (ko)	2001-04-06	신규한 β-락탐 화합물 및 이의 제조 방법
JP2003183282A (ja)	2003-07-03	カルバペネム化合物
GB2144126A (en)	1985-02-27	Penem carboxylix acids and the preparation thereof
WO1995014692A1 (en)	1995-06-01	Cabapenem derivatives and processes for preparing the same
US4837215A (en)	1989-06-06	Penem derivatives
HU197904B (en)	1989-06-28	Process for producing carbapenem antibiotics
EP0003892A1 (de)	1979-09-05	Beta-Lactam Verbindungen,Verfahren zu ihrer Herstellung,sie enthaltende Arzneipräparate und Zwischenprodukte zur Verwendung in ihrer Herstellung

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