JPS5910588A - カルバペネム抗生物質 - Google Patents

カルバペネム抗生物質

Info

Publication number: JPS5910588A
Authority: JP; Japan
Prior art keywords: alkyl; carbon atoms; hydrogen; group; moiety
Prior art date: 1982-06-18
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP58108020A

Other languages

English (en)

Japanese (ja)

Inventor

チヤング　アン　キム

ピ−タ−　フランシス　ミスコ　ジユニア

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bristol Myers Co

Original Assignee

Bristol Myers 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.)

1982-06-18

Filing date

1983-06-17

Publication date

1984-01-20

1983-06-17 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1984-01-20 Publication of JPS5910588A publication Critical patent/JPS5910588A/ja

Status Pending legal-status Critical Current

Links

YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title description 30
230000003115 biocidal effect Effects 0.000 title description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 244
125000000217 alkyl group Chemical group 0.000 claims description 217
150000001875 compounds Chemical class 0.000 claims description 216
229910052739 hydrogen Inorganic materials 0.000 claims description 184
239000001257 hydrogen Substances 0.000 claims description 184
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 162
125000000623 heterocyclic group Chemical group 0.000 claims description 133
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 112
125000000753 cycloalkyl group Chemical group 0.000 claims description 105
229910052757 nitrogen Inorganic materials 0.000 claims description 94
150000002431 hydrogen Chemical class 0.000 claims description 70
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 65
-1 chloro, carboxyl Chemical group 0.000 claims description 64
125000003118 aryl group Chemical group 0.000 claims description 62
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
125000005842 heteroatom Chemical group 0.000 claims description 59
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
125000003342 alkenyl group Chemical group 0.000 claims description 56
229910052760 oxygen Inorganic materials 0.000 claims description 56
125000006239 protecting group Chemical group 0.000 claims description 54
125000000304 alkynyl group Chemical group 0.000 claims description 53
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 53
239000001301 oxygen Substances 0.000 claims description 53
125000001153 fluoro group Chemical group F* 0.000 claims description 52
125000001072 heteroaryl group Chemical group 0.000 claims description 51
125000004475 heteroaralkyl group Chemical group 0.000 claims description 47
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 46
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
239000000543 intermediate Substances 0.000 claims description 44
125000001931 aliphatic group Chemical group 0.000 claims description 43
125000004434 sulfur atom Chemical group 0.000 claims description 42
125000001309 chloro group Chemical group Cl* 0.000 claims description 40
150000002500 ions Chemical class 0.000 claims description 38
125000002947 alkylene group Chemical group 0.000 claims description 34
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 34
125000004429 atom Chemical group 0.000 claims description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
229910001868 water Inorganic materials 0.000 claims description 33
125000001246 bromo group Chemical group Br* 0.000 claims description 32
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 30
125000003710 aryl alkyl group Chemical group 0.000 claims description 27
238000006467 substitution reaction Methods 0.000 claims description 27
125000001424 substituent group Chemical group 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 25
230000002441 reversible effect Effects 0.000 claims description 23
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
150000001412 amines Chemical class 0.000 claims description 21
125000004956 cyclohexylene group Chemical group 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
238000000034 method Methods 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 17
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
125000001118 alkylidene group Chemical group 0.000 claims description 15
239000003960 organic solvent Substances 0.000 claims description 14
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000003367 polycyclic group Chemical group 0.000 claims description 12
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
150000001450 anions Chemical group 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
125000004979 cyclopentylene group Chemical group 0.000 claims description 10
125000004404 heteroalkyl group Chemical group 0.000 claims description 10
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
229920006395 saturated elastomer Polymers 0.000 claims description 8
239000011593 sulfur Substances 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 5
125000002346 iodo group Chemical group I* 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000000129 anionic group Chemical group 0.000 claims description 4
125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
239000012359 Methanesulfonyl chloride Substances 0.000 claims 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 claims description 3
229940079593 drug Drugs 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims description 3
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
229940006461 iodide ion Drugs 0.000 claims description 2
125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 2
229910052709 silver Inorganic materials 0.000 claims description 2
239000004332 silver Substances 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 16
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 6
239000003990 capacitor Substances 0.000 claims 3
SBUKLPSBNFWJCU-UHFFFAOYSA-N ClIBr Chemical compound ClIBr SBUKLPSBNFWJCU-UHFFFAOYSA-N 0.000 claims 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 2
241000162682 Heterogen Species 0.000 claims 2
239000004855 amber Chemical group 0.000 claims 2
150000001735 carboxylic acids Chemical class 0.000 claims 2
239000003610 charcoal Substances 0.000 claims 2
235000014113 dietary fatty acids Nutrition 0.000 claims 2
229930195729 fatty acid Natural products 0.000 claims 2
239000000194 fatty acid Substances 0.000 claims 2
150000004665 fatty acids Chemical class 0.000 claims 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
239000004215 Carbon black (E152) Substances 0.000 claims 1
241000238557 Decapoda Species 0.000 claims 1
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 1
241000219289 Silene Species 0.000 claims 1
125000005103 alkyl silyl group Chemical group 0.000 claims 1
230000002547 anomalous effect Effects 0.000 claims 1
125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 1
CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims 1
229910052918 calcium silicate Inorganic materials 0.000 claims 1
125000000837 carbohydrate group Chemical group 0.000 claims 1
150000001793 charged compounds Chemical class 0.000 claims 1
125000004965 chloroalkyl group Chemical group 0.000 claims 1
239000013078 crystal Substances 0.000 claims 1
239000009937 cyclo 3 Substances 0.000 claims 1
235000013601 eggs Nutrition 0.000 claims 1
230000002550 fecal effect Effects 0.000 claims 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
229910052737 gold Inorganic materials 0.000 claims 1
239000010931 gold Substances 0.000 claims 1
150000004678 hydrides Chemical class 0.000 claims 1
125000001145 hydrido group Chemical group *[H] 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
230000014759 maintenance of location Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
PLGIIOKXCKDKEU-VXLYETTFSA-N n-[4-chloro-3-[(e)-(2-methylpropan-2-yl)oxyiminomethyl]phenyl]-2-methylfuran-3-carbothioamide Chemical compound O1C=CC(C(=S)NC=2C=C(\C=N\OC(C)(C)C)C(Cl)=CC=2)=C1C PLGIIOKXCKDKEU-VXLYETTFSA-N 0.000 claims 1
238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
235000019989 pulque Nutrition 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
210000002784 stomach Anatomy 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 32
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 23
239000002253 acid Substances 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
239000007787 solid Substances 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
241000699670 Mus sp. Species 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
239000012071 phase Substances 0.000 description 12
125000002252 acyl group Chemical group 0.000 description 10
239000000843 powder Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
241000894006 Bacteria Species 0.000 description 9
239000002585 base Substances 0.000 description 9
150000003952 β-lactams Chemical class 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
229940041011 carbapenems Drugs 0.000 description 6
230000000694 effects Effects 0.000 description 6
238000004108 freeze drying Methods 0.000 description 6
238000007918 intramuscular administration Methods 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
238000011282 treatment Methods 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000000872 buffer Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
125000006413 ring segment Chemical group 0.000 description 5
238000003756 stirring Methods 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
239000007853 buffer solution Substances 0.000 description 4
125000000392 cycloalkenyl group Chemical group 0.000 description 4
125000004185 ester group Chemical group 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
125000002950 monocyclic group Chemical group 0.000 description 4
229930014626 natural product Natural products 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000011084 recovery Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
239000011575 calcium Substances 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000003054 catalyst Substances 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
238000001816 cooling Methods 0.000 description 3
238000006073 displacement reaction Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
239000011707 mineral Substances 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
125000000714 pyrimidinyl group Chemical group 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
125000003831 tetrazolyl group Chemical group 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
230000002485 urinary effect Effects 0.000 description 3
239000003643 water by type Substances 0.000 description 3
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-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
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
241000282414 Homo sapiens Species 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000002723 alicyclic group Chemical group 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
230000000844 anti-bacterial effect Effects 0.000 description 2
239000004599 antimicrobial Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
125000002993 cycloalkylene group Chemical group 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
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235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
150000007970 thio esters Chemical class 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
238000006257 total synthesis reaction Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (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)

JP58108020A 1982-06-18 1983-06-17 カルバペネム抗生物質 Pending JPS5910588A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US38965282A	1982-06-18	1982-06-18
US389652		1982-06-18
US499690		1983-06-07

Publications (1)

Publication Number	Publication Date
JPS5910588A true JPS5910588A (ja)	1984-01-20

Family

ID=23539144

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58108020A Pending JPS5910588A (ja)	1982-06-18	1983-06-17	カルバペネム抗生物質

Country Status (3)

Country	Link
JP (1)	JPS5910588A (fr)
BE (1)	BE897086A (fr)
ZA (1)	ZA834472B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1272719A (fr)	1986-03-06	1990-08-14	Pierre Dextraze	Antibiotiques a base de carbapenemes

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5277085A (en) *	1975-11-21	1977-06-29	Merck & Co Inc	Nnalkyl derivative of thienamycine
JPS53137992A (en) *	1977-05-05	1978-12-01	Merck & Co Inc	Nnalkyllnnacyl derivative of thienamycine
JPS565478A (en) *	1979-04-19	1981-01-20	Merck & Co Inc	22substitutedd66substituteddcarbadethiapenee 22emm33carboxylic acid

1983
- 1983-06-17 BE BE0/211032A patent/BE897086A/fr not_active IP Right Cessation
- 1983-06-17 ZA ZA834472A patent/ZA834472B/xx unknown
- 1983-06-17 JP JP58108020A patent/JPS5910588A/ja active Pending

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5277085A (en) *	1975-11-21	1977-06-29	Merck & Co Inc	Nnalkyl derivative of thienamycine
JPS53137992A (en) *	1977-05-05	1978-12-01	Merck & Co Inc	Nnalkyllnnacyl derivative of thienamycine
JPS565478A (en) *	1979-04-19	1981-01-20	Merck & Co Inc	22substitutedd66substituteddcarbadethiapenee 22emm33carboxylic acid

Also Published As

Publication number	Publication date
BE897086A (fr)	1983-12-19
ZA834472B (en)	1984-03-28

Publication	Publication Date	Title
DE3785163T2 (de)	1993-07-29	3-pyrrolidinylthio-1-azabicyclo(3.2.0)hept-2-en-2-carbonsaeurederivate und verfahren zu deren herstellung.
DE69129175T2 (de)	1998-09-03	1-Methylcarbapenemderivate und Verfahren zu ihrer Herstellung
GB2122196A (en)	1984-01-11	Carbapenem antibiotics
EP0050334A1 (fr)	1982-04-28	Acides 2-carbamimidoyl-6-substitués-1-carbadethiapen-2-ème-3-carboxyliques, procédé de préparation et une composition antibiotique les contenant
US4150145A (en)	1979-04-17	N-alkylated derivatives of thienamycin sulfoxide and sulfone
KR880001069B1 (ko)	1988-06-20	카르바페넴 유도체및 그의 제조방법
KR890002228B1 (ko)	1989-06-24	카르바페넴 유도체 및 그의 제조방법
US4424230A (en)	1984-01-03	6-(1'-Hydroxyethyl)-3-substituted amino-1-azabicyclo- 3.2.0!hept-2-en-7-one-2-carboxylic acid
US4310538A (en)	1982-01-12	3-Halo-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acid
JPH05255250A (ja)	1993-10-05	新規第四級アミンチオール化合物
DE69807722T2 (de)	2003-04-30	Carbapenemderivate
US4076826A (en)	1978-02-28	3-(.beta.-Hydroxyethylidene)-6-(α-Hydroxyethyl)-7-oxo-4-oxaazabicyclo[3.2.0]heptene-2-carboxylic acid and derivatives thereof
KR100530478B1 (ko)	2005-11-23	카르바페넴 화합물, 이의 용도 및 이의 중간체 화합물
DE69523058T2 (de)	2002-02-07	Carbapenem-derivate
FI83323B (fi)	1991-03-15	Foerfarande foer framstaellning av terapeutiskt aktiva karbapenemderivat som substituerats i 2-staellningen med en heterotioalkyltiogrupp.
KR880001055B1 (ko)	1988-06-18	카르바페넴 유도체의 제조방법
JPS62265287A (ja)	1987-11-18	カルバペネム抗生物質
JPS5989683A (ja)	1984-05-23	カルバペネム抗生物質
JPS6187682A (ja)	1986-05-06	カルバペネム抗生物質
KR100246950B1 (ko)	2000-05-01	신규 카바페넴계 항생제 및 그의 제조방법
JPH0432830B2 (fr)	1992-06-01
KR100246953B1 (ko)	2000-05-01	신규 카바페넴계 항생제
WO1994005667A1 (fr)	1994-03-17	Derives de carbapenem et procedes pour leur preparation
KR870001743B1 (ko)	1987-09-26	카바펜엠 항생제의 제조방법
KR100246949B1 (ko)	2000-05-01	신규 카바페넴계 항생제