IE52421B1 - Carbapenen compounds - Google Patents

Carbapenen compounds

Info

Publication number: IE52421B1
Authority: IE; Ireland
Prior art keywords: alkyl; methyl; compounds; group; oxo
Prior art date: 1981-01-30

Application number

IE197/82A

Other languages

English (en)

Other versions

IE820197L (en

Original Assignee

Hoffmann La Roche

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.)

1981-01-30

Filing date

1982-01-29

Publication date

1987-10-28

1981-01-30 Priority claimed from CH62081A external-priority patent/CH646171A5/de

1981-12-07 Priority claimed from CH7802/81A external-priority patent/CH651564A5/de

1982-01-29 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1982-07-30 Publication of IE820197L publication Critical patent/IE820197L/xx

1987-10-28 Publication of IE52421B1 publication Critical patent/IE52421B1/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 70
150000003839 salts Chemical class 0.000 claims abstract description 38
150000002148 esters Chemical class 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 27
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
238000004519 manufacturing process Methods 0.000 claims abstract description 10
150000004677 hydrates Chemical class 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
238000011282 treatment Methods 0.000 claims abstract description 6
208000035473 Communicable disease Diseases 0.000 claims abstract description 5
238000011321 prophylaxis Methods 0.000 claims abstract description 5
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 4
125000004468 heterocyclylthio group Chemical group 0.000 claims abstract description 3
125000002619 bicyclic group Chemical group 0.000 claims abstract 3
-1 N-oxido Chemical group 0.000 claims description 125
238000000034 method Methods 0.000 claims description 39
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
125000001424 substituent group Chemical group 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
229910052794 bromium Inorganic materials 0.000 claims description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
229910052731 fluorine Inorganic materials 0.000 claims description 12
239000011737 fluorine Substances 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
239000000460 chlorine Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
239000005864 Sulphur Substances 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000001246 bromo group Chemical group Br* 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
238000003776 cleavage reaction Methods 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
230000007017 scission Effects 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
150000002923 oximes Chemical class 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 2
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 3
239000000126 substance Substances 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 180
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 152
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 140
239000000243 solution Substances 0.000 description 131
239000000203 mixture Substances 0.000 description 101
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 62
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
239000003921 oil Substances 0.000 description 46
235000019198 oils Nutrition 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
229910052938 sodium sulfate Inorganic materials 0.000 description 31
235000011152 sodium sulphate Nutrition 0.000 description 31
239000012074 organic phase Substances 0.000 description 30
239000000741 silica gel Substances 0.000 description 29
229910002027 silica gel Inorganic materials 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
238000004587 chromatography analysis Methods 0.000 description 27
239000000047 product Substances 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
238000000746 purification Methods 0.000 description 20
239000007858 starting material Substances 0.000 description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
239000011734 sodium Substances 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000013078 crystal Substances 0.000 description 16
239000002904 solvent Substances 0.000 description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
239000008346 aqueous phase Substances 0.000 description 14
238000002425 crystallisation Methods 0.000 description 14
230000008025 crystallization Effects 0.000 description 14
238000010828 elution Methods 0.000 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 description 14
238000003756 stirring Methods 0.000 description 14
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 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
229910052708 sodium Inorganic materials 0.000 description 12
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 12
239000012071 phase Substances 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
101150041968 CDC13 gene Proteins 0.000 description 10
239000003480 eluent Substances 0.000 description 10
238000007363 ring formation reaction Methods 0.000 description 10
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000000463 material Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
239000012300 argon atmosphere Substances 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
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
239000008055 phosphate buffer solution Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000843 powder Substances 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
239000000284 extract Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
RLBQTMYBGOKQBU-UHFFFAOYSA-N 2-(2-methyl-1,3-dioxolan-2-yl)acetaldehyde Chemical compound O=CCC1(C)OCCO1 RLBQTMYBGOKQBU-UHFFFAOYSA-N 0.000 description 4
ITAPQTGSOLYCLH-UHFFFAOYSA-N 4-[(2-methyl-1,3-dioxolan-2-yl)methyl]azetidin-2-one Chemical compound C1OC(CC2CC(N2)=O)(C)OC1 ITAPQTGSOLYCLH-UHFFFAOYSA-N 0.000 description 4
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 4
239000002808 molecular sieve Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000012264 purified product Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000005051 trimethylchlorosilane Substances 0.000 description 4
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
VNAJIZNBAHUGRS-UHFFFAOYSA-N 4-(3-bromo-2,2-dimethoxypropyl)azetidin-2-one Chemical compound BrCC(CC1CC(N1)=O)(OC)OC VNAJIZNBAHUGRS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
101100132433 Arabidopsis thaliana VIII-1 gene Proteins 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
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 3
235000019759 Maize starch Nutrition 0.000 description 3
241000219470 Mirabilis Species 0.000 description 3
241000607715 Serratia marcescens Species 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000008272 agar Substances 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000004042 decolorization Methods 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
RPZBLMVYFMNYPC-UHFFFAOYSA-N ethyl 4-(2-methyl-1,3-dioxolan-2-yl)but-2-enoate Chemical compound CCOC(=O)C=CCC1(C)OCCO1 RPZBLMVYFMNYPC-UHFFFAOYSA-N 0.000 description 3
238000001640 fractional crystallisation Methods 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000008363 phosphate buffer Substances 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
230000000630 rising effect Effects 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
BKGLGDXGKJTHOR-YUMQZZPRSA-N (3S,4S)-4-(3-bromo-2,2-dimethoxypropyl)-3-ethylazetidin-2-one Chemical compound BrCC(C[C@H]1[C@@H](C(N1)=O)CC)(OC)OC BKGLGDXGKJTHOR-YUMQZZPRSA-N 0.000 description 2
LAVRZGWBNKLKAT-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 6-(1-hydroxyethyl)-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound OC(C)C1C2CC(=C(N2C1=O)C(=O)OCOC(C(C)(C)C)=O)CSC1=NN=NN1C LAVRZGWBNKLKAT-UHFFFAOYSA-N 0.000 description 2
JQDOSKYNGOYQNP-UHFFFAOYSA-N 3-amino-4-(2-methyl-1,3-dioxolan-2-yl)butanoic acid Chemical compound NC(CC(=O)O)CC1(C)OCCO1 JQDOSKYNGOYQNP-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000588697 Enterobacter cloacae Species 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
239000004133 Sodium thiosulphate Substances 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
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230000009885 systemic effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
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 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

IE197/82A 1981-01-30 1982-01-29 Carbapenen compounds IE52421B1 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH62081A CH646171A5 (en)	1981-01-30	1981-01-30	Bicyclic compounds
CH7802/81A CH651564A5 (en)	1981-12-07	1981-12-07	7-Oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid derivatives

Publications (2)

Publication Number	Publication Date
IE820197L IE820197L (en)	1982-07-30
IE52421B1 true IE52421B1 (en)	1987-10-28

Family

ID=25685143

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE197/82A IE52421B1 (en)	1981-01-30	1982-01-29	Carbapenen compounds

Country Status (15)

Country	Link
AT (1)	AT377762B (xx)
AU (1)	AU7979882A (xx)
CA (1)	CA1179675A (xx)
DE (1)	DE3201957A1 (xx)
DK (1)	DK32082A (xx)
FR (1)	FR2499081B1 (xx)
GB (1)	GB2092147B (xx)
IE (1)	IE52421B1 (xx)
IL (1)	IL64859A (xx)
IT (1)	IT1153416B (xx)
LU (1)	LU83906A1 (xx)
NL (1)	NL8200217A (xx)
NZ (1)	NZ199487A (xx)
PH (1)	PH19227A (xx)
SE (1)	SE8200515L (xx)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4729993A (en) *	1984-12-13	1988-03-08	Merck & Co., Inc.	Carbapenems and 1-methylcarbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkyl substituent
US4725594A (en) *	1984-12-13	1988-02-16	Merck & Co., Inc.	Carbapenems having an internally or externally alkylated mono- or bicyclic 2-quaternary heteroarylalxyl heteromethyl substituent
US4680292A (en) *	1984-12-13	1987-07-14	Merck & Co., Inc.	Carbapenems and 1-methylcarbapenems having a 2-heteroaryliumaliphatic substituent
GB8607921D0 (en) *	1986-04-01	1986-05-08	Fujisawa Pharmaceutical Co	3,4-disubstituted-2-azetidinone derivatives
ZA912279B (en) *	1990-04-09	1992-02-26	Hoffmann La Roche	Carbapenem compounds
US5068232A (en) *	1990-04-10	1991-11-26	American Cyanamid Company	Novel 2-substituted alkyl-3-carboxy carbapenems as antibiotics and a method of producing them
US5607928A (en) *	1994-08-05	1997-03-04	Zeneca Limited	Carbapenem derivatives containing a bicyclic ketone substituent and their use as anti-infectives
ES2712484T3 (es) *	2004-06-10	2019-05-13	Fob Synthesis Inc	Bactericidas de carbapenem con actividad gramnegativa y procesos para su preparación
US20110118462A1 (en) *	2009-11-18	2011-05-19	Guangzhou Baiyunshan Pharmaceutical Co., Ltd. Guangzhou Baiyunshan Pharmaceutical Factory	N-heterocyclic substituent-containing antibiotic, preparation and use thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1593524A (en) *	1976-11-19	1981-07-15	Merck & Co Inc	1-carba-2-penem-3-carboxylic acids
DE2811514A1 (de) *	1977-03-19	1978-09-21	Beecham Group Ltd	Ester der 7-oxo-1-azabicyclo eckige klammer auf 3.2.0 eckige klammer zu hept- 2-en-2-carbonsaeure und deren derivate, verfahren zur herstellung dieser verbindungen und diese verbindungen enthaltende pharmazeutische zubereitungen
GB2021656B (en) *	1978-05-11	1982-08-25	Ladd Harley G F	Pleat forming means and method
US4260627A (en) *	1978-10-24	1981-04-07	Merck & Co., Inc.	1-, 6- And 2-substituted-1-carba-2-penem-3-carboxylic acids
JPS56122379A (en) *	1980-03-03	1981-09-25	Sankyo Co Ltd	1-carba-2-penem-3-carboxylic acid derivative

1982
- 1982-01-08 CA CA000393840A patent/CA1179675A/en not_active Expired
- 1982-01-14 NZ NZ199487A patent/NZ199487A/en unknown
- 1982-01-19 IT IT19187/82A patent/IT1153416B/it active
- 1982-01-21 NL NL8200217A patent/NL8200217A/nl not_active Application Discontinuation
- 1982-01-22 PH PH26771A patent/PH19227A/en unknown
- 1982-01-22 DE DE19823201957 patent/DE3201957A1/de not_active Withdrawn
- 1982-01-25 AU AU79798/82A patent/AU7979882A/en not_active Abandoned
- 1982-01-25 IL IL64859A patent/IL64859A/xx unknown
- 1982-01-25 DK DK32082A patent/DK32082A/da not_active Application Discontinuation
- 1982-01-28 FR FR828201345A patent/FR2499081B1/fr not_active Expired
- 1982-01-28 LU LU83906A patent/LU83906A1/de unknown
- 1982-01-29 AT AT0034082A patent/AT377762B/de not_active IP Right Cessation
- 1982-01-29 IE IE197/82A patent/IE52421B1/en unknown
- 1982-01-29 SE SE8200515A patent/SE8200515L/xx not_active Application Discontinuation
- 1982-01-29 GB GB8202523A patent/GB2092147B/en not_active Expired

Also Published As

Publication number	Publication date
FR2499081A1 (fr)	1982-08-06
NL8200217A (nl)	1982-08-16
NZ199487A (en)	1986-02-21
AU7979882A (en)	1982-09-23
CA1179675A (en)	1984-12-18
SE8200515L (sv)	1982-07-31
DE3201957A1 (de)	1982-09-09
GB2092147A (en)	1982-08-11
IT8219187A0 (it)	1982-01-19
LU83906A1 (de)	1983-09-02
PH19227A (en)	1986-02-12
FR2499081B1 (fr)	1985-07-26
DK32082A (da)	1982-07-31
ATA34082A (de)	1984-09-15
IE820197L (en)	1982-07-30
AT377762B (de)	1985-04-25
IT1153416B (it)	1987-01-14
GB2092147B (en)	1984-12-05
IL64859A (en)	1985-06-30

Publication	Publication Date	Title
US4526718A (en)	1985-07-02	3,3-Di(acylthio)-2(4-allylthioazetidin-2-on-1-yl)propenoic acid ester compounds
EP0090366B1 (en)	1987-11-25	1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid derivatives, processes for the preparation thereof and pharmaceutical compositions containing them
NO164980B (no)	1990-08-27	Analogifremgangsmaate til fremstilling av terapeutisk aktive karbapenemderivater.
US4503064A (en)	1985-03-05	Oxime substituted penems
US4477662A (en)	1984-10-16	2-Substituted thio carbapenem derivatives
EP0044170A1 (en)	1982-01-20	Beta-lactam antibiotics, their preparation and use
CA2065079C (en)	2003-03-18	Polycyclic carbapenem compounds, their production and use
IE52421B1 (en)	1987-10-28	Carbapenen compounds
US4614738A (en)	1986-09-30	2-(N-heterocycloaliphaticthio)penems
AU609488B2 (en)	1991-05-02	(5r, 6s, 1r)-6-(1-hydroxyethyl)-2-(methoxymethyl)penem-3- carboxylic acid derivatives
CH651037A5 (de)	1985-08-30	Penem-3-carbonsaeurederivate und verfahren zu deren herstellung.
CA1235117A (en)	1988-04-12	2-dioxacycloalkylthiopenem derivatives
US4224336A (en)	1980-09-23	3-(2-Aminoethylthio)-6-amido-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylic acid
KR100530478B1 (ko)	2005-11-23	카르바페넴 화합물, 이의 용도 및 이의 중간체 화합물
US4559333A (en)	1985-12-17	Hydrazone substituted penems
US7163936B2 (en)	2007-01-16	β-lactam compounds and process for producing the same
US4690922A (en)	1987-09-01	2-(heterocycloalkylthio)penems
US4410533A (en)	1983-10-18	β-Lactam antibiotics, their preparation and use
EP0061231A1 (en)	1982-09-29	Process for the preparation of azabicyclo(3.2.0)-hept-2-ene derivatives
US4923856A (en)	1990-05-08	Penem compounds
JPS6118779A (ja)	1986-01-27	カルバペネム類
EP0118875B1 (en)	1987-12-16	6-(hydroxyalkyl)-2-(heteroarylalkylthio)-penems, pharmaceutical compositions containing them, and processes for their preparation
US4617300A (en)	1986-10-14	2(N-heterocyclyl) penems
US4587241A (en)	1986-05-06	Heterocyclic substituted penems
US4281002A (en)	1981-07-28	3-(2-Aminoethylthio)-6-amido-7-oxo-1-azabicyclo(3.2.0)-hept-2-ene-2-carboxylic acid