NL8303310A - Carbapenem antibiotica. - Google Patents
Carbapenem antibiotica. Download PDFInfo
- Publication number
- NL8303310A NL8303310A NL8303310A NL8303310A NL8303310A NL 8303310 A NL8303310 A NL 8303310A NL 8303310 A NL8303310 A NL 8303310A NL 8303310 A NL8303310 A NL 8303310A NL 8303310 A NL8303310 A NL 8303310A
- Authority
- NL
- Netherlands
- Prior art keywords
- alkyl
- carbon atoms
- phenyl
- hydrogen
- substituted
- Prior art date
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- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title description 32
- 239000003242 anti bacterial agent Substances 0.000 title description 9
- 229940088710 antibiotic agent Drugs 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 666
- 125000004432 carbon atom Chemical group C* 0.000 claims description 431
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 387
- 125000001424 substituent group Chemical group 0.000 claims description 386
- 125000000623 heterocyclic group Chemical group 0.000 claims description 312
- 229910052739 hydrogen Inorganic materials 0.000 claims description 290
- 239000001257 hydrogen Substances 0.000 claims description 288
- 150000001875 compounds Chemical class 0.000 claims description 278
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 259
- 229910052736 halogen Inorganic materials 0.000 claims description 201
- 150000002367 halogens Chemical group 0.000 claims description 198
- -1 chloro, carboxyl Chemical group 0.000 claims description 196
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 191
- 125000003282 alkyl amino group Chemical group 0.000 claims description 190
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 190
- 125000001072 heteroaryl group Chemical group 0.000 claims description 177
- 229910052757 nitrogen Inorganic materials 0.000 claims description 166
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 159
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 149
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 148
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 142
- 125000004429 atom Chemical group 0.000 claims description 126
- 125000005842 heteroatom Chemical group 0.000 claims description 122
- 125000003342 alkenyl group Chemical group 0.000 claims description 118
- 125000006239 protecting group Chemical group 0.000 claims description 117
- 125000003545 alkoxy group Chemical group 0.000 claims description 112
- 125000000304 alkynyl group Chemical group 0.000 claims description 110
- 229910052760 oxygen Inorganic materials 0.000 claims description 110
- 125000004434 sulfur atom Chemical group 0.000 claims description 99
- 125000003118 aryl group Chemical group 0.000 claims description 93
- 239000001301 oxygen Substances 0.000 claims description 93
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 93
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 92
- 150000003839 salts Chemical class 0.000 claims description 90
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 83
- 125000001931 aliphatic group Chemical group 0.000 claims description 78
- 125000000129 anionic group Chemical group 0.000 claims description 72
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 72
- 229910052794 bromium Chemical group 0.000 claims description 72
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 71
- 239000000460 chlorine Chemical group 0.000 claims description 71
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 67
- 229910052801 chlorine Inorganic materials 0.000 claims description 67
- 229910052717 sulfur Inorganic materials 0.000 claims description 66
- 229910052799 carbon Inorganic materials 0.000 claims description 64
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 64
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 62
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 62
- 239000011737 fluorine Chemical group 0.000 claims description 62
- 229910052731 fluorine Inorganic materials 0.000 claims description 62
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 62
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
- 125000001153 fluoro group Chemical group F* 0.000 claims description 51
- 125000002947 alkylene group Chemical group 0.000 claims description 46
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 41
- 150000001721 carbon Chemical group 0.000 claims description 39
- 125000004414 alkyl thio group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 32
- 125000001118 alkylidene group Chemical group 0.000 claims description 31
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 29
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 28
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 26
- 125000001246 bromo group Chemical group Br* 0.000 claims description 25
- 125000004423 acyloxy group Chemical group 0.000 claims description 23
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 18
- 125000003367 polycyclic group Chemical group 0.000 claims description 18
- 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 17
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 125000002837 carbocyclic group Chemical group 0.000 claims description 16
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 16
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 16
- 229910052740 iodine Inorganic materials 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 8
- 150000002500 ions Chemical class 0.000 claims description 8
- 125000004954 trialkylamino group Chemical group 0.000 claims description 8
- GWDQURJBGWHTKL-UHFFFAOYSA-N [(diaminomethylideneamino)-nitro-lambda3-chloranyl]methanimidamide Chemical compound C(N)(=N)Cl([N+](=O)[O-])NC(=N)N GWDQURJBGWHTKL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000001228 spectrum Methods 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000002168 alkylating agent Substances 0.000 claims description 6
- 229940100198 alkylating agent Drugs 0.000 claims description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 5
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical group FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 95
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 3
- 101710150115 Sensory rhodopsin-2 Proteins 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229940073020 nitrol Drugs 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-OUBTZVSYSA-N Ammonia-15N Chemical compound [15NH3] QGZKDVFQNNGYKY-OUBTZVSYSA-N 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 1
- 206010012239 Delusion Diseases 0.000 claims 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 1
- PVCJBIDYLUTNOV-UHFFFAOYSA-N NC(NCl[N+]([O-])=O)=N Chemical compound NC(NCl[N+]([O-])=O)=N PVCJBIDYLUTNOV-UHFFFAOYSA-N 0.000 claims 1
- BPZSYCZIITTYBL-YJYMSZOUSA-N R-Formoterol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-YJYMSZOUSA-N 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 230000002547 anomalous effect Effects 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 claims 1
- 125000006243 carbonyl protecting group Chemical group 0.000 claims 1
- 239000011651 chromium Substances 0.000 claims 1
- 229910052804 chromium Inorganic materials 0.000 claims 1
- 231100000868 delusion Toxicity 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 239000000428 dust Substances 0.000 claims 1
- 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 1
- 125000004474 heteroalkylene group Chemical group 0.000 claims 1
- 125000001145 hydrido group Chemical group *[H] 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 235000002020 sage Nutrition 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000011630 iodine Substances 0.000 description 14
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000002252 acyl group Chemical group 0.000 description 11
- 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 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 150000003573 thiols Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003638 chemical reducing agent 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
- 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
- 230000000694 effects Effects 0.000 description 3
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- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 3
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- 230000004962 physiological condition Effects 0.000 description 3
- 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
- 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
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
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- 125000002971 oxazolyl group Chemical group 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- CGRJOQDFNTYSGH-UHFFFAOYSA-N tritylphosphane Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(P)C1=CC=CC=C1 CGRJOQDFNTYSGH-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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- 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
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
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- 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)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42575582A | 1982-09-28 | 1982-09-28 | |
| US42575582 | 1982-09-28 | ||
| US53001183A | 1983-09-09 | 1983-09-09 | |
| US53001183 | 1983-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8303310A true NL8303310A (nl) | 1984-04-16 |
Family
ID=27026797
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8303310A NL8303310A (nl) | 1982-09-28 | 1983-09-27 | Carbapenem antibiotica. |
Country Status (29)
| Country | Link |
|---|---|
| KR (1) | KR890002228B1 (sv) |
| AR (1) | AR241785A1 (sv) |
| AT (1) | AT382621B (sv) |
| AU (1) | AU575541B2 (sv) |
| CA (1) | CA1269978A (sv) |
| CH (1) | CH656130A5 (sv) |
| CS (1) | CS247168B2 (sv) |
| DD (1) | DD212255A5 (sv) |
| DE (1) | DE3334937A1 (sv) |
| DK (1) | DK442383A (sv) |
| ES (1) | ES525983A0 (sv) |
| FI (1) | FI78094C (sv) |
| FR (1) | FR2533568B1 (sv) |
| GB (1) | GB2128187B (sv) |
| GR (1) | GR78696B (sv) |
| HU (1) | HU191066B (sv) |
| IE (1) | IE55947B1 (sv) |
| IL (1) | IL69824A (sv) |
| IT (1) | IT1163944B (sv) |
| LU (1) | LU85021A1 (sv) |
| NL (1) | NL8303310A (sv) |
| NO (1) | NO163284C (sv) |
| NZ (1) | NZ205626A (sv) |
| OA (1) | OA07548A (sv) |
| PT (1) | PT77404B (sv) |
| SE (1) | SE461734B (sv) |
| SU (1) | SU1493108A3 (sv) |
| YU (1) | YU43196B (sv) |
| ZW (1) | ZW20783A1 (sv) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4683296A (en) * | 1983-03-07 | 1987-07-28 | Bristol-Myers Company | Carbapenem intermediates |
| CA1273011A (en) * | 1984-07-02 | 1990-08-21 | Susan M. Schmitt | Carbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkylthio substituent |
| CA1273012A (en) * | 1984-07-02 | 1990-08-21 | Burton G. Christensen | 1-methylcarbapenems having an externally alkylated mono- of bicyclic 2-quarternary heteroarylalkylthio substituent |
| US4680292A (en) * | 1984-12-13 | 1987-07-14 | Merck & Co., Inc. | Carbapenems and 1-methylcarbapenems having a 2-heteroaryliumaliphatic 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 |
| 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 |
| US4665169A (en) * | 1985-09-11 | 1987-05-12 | Bristol-Myers Company | Carbapenem antibiotics |
| US4880922A (en) * | 1985-11-22 | 1989-11-14 | Bristol-Myers Company | Carbapenems with quaternized heterothioalkylthio substitution at position 2 |
| NZ219892A (en) * | 1986-04-15 | 1991-02-26 | Merck & Co Inc | N-amino quaternised heteroarylium carbapenem derivatives and pharmaceutical compositions thereof |
| DK168047B1 (da) * | 1987-12-07 | 1994-01-24 | Lederle Japan Ltd | (1r,5s,6s)-2-substitueret thio-6-oe(r)-1-hydroxyethylaa-1-methyl-carbapenem-3-carboxylsyrederivater, fremgangsmaade til remstilling deraf, midler og praeparater indeholdende den krystallinske forbindelse samt dens anvendelse. |
| WO1997025325A1 (en) * | 1996-01-12 | 1997-07-17 | Takeda Chemical Industries, Ltd. | Carbapenem compounds, their production and use |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK165280A (da) * | 1979-04-19 | 1980-10-20 | Merck & Co Inc | Fremgangsmaade til fremstilling af 2- og 6-substituerede 1-carbadethiapen-2-em-3-carboxylsyrer og mellemprodukter til brug ved udoevelse af fremgangsmaaden |
| IE52147B1 (en) * | 1980-03-27 | 1987-07-08 | Merck & Co Inc | 4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation |
| EP0038869A1 (en) * | 1980-04-30 | 1981-11-04 | Merck & Co. Inc. | Process for the preparation of 1-carbapenems, and intermediates for their preparation |
| PT73791B (en) * | 1980-10-17 | 1983-10-14 | Merck & Co Inc | Process for preparing 2-carbamimidoyl-6-substituted-1- -carbadethiapen-2-em-3-carboxylic acids |
| GB2089340B (en) * | 1980-10-25 | 1984-09-19 | Beecham Group Ltd | -lactam antibiotics their preparation and their use |
| US4552873A (en) * | 1981-08-19 | 1985-11-12 | Sankyo Company Limited | Carbapenem compounds, and compositions containing them |
| EP0074599A1 (en) * | 1981-09-09 | 1983-03-23 | Takeda Chemical Industries, Ltd. | 5,6-cis-Carbapenem derivatives, their production and use |
-
1983
- 1983-09-16 CA CA000436924A patent/CA1269978A/en not_active Expired - Lifetime
- 1983-09-16 NZ NZ205626A patent/NZ205626A/en unknown
- 1983-09-21 AU AU19342/83A patent/AU575541B2/en not_active Ceased
- 1983-09-22 YU YU1906/83A patent/YU43196B/xx unknown
- 1983-09-22 FR FR838315069A patent/FR2533568B1/fr not_active Expired - Fee Related
- 1983-09-22 GR GR72509A patent/GR78696B/el unknown
- 1983-09-23 FI FI833417A patent/FI78094C/sv not_active IP Right Cessation
- 1983-09-27 SU SU833648007A patent/SU1493108A3/ru active
- 1983-09-27 PT PT77404A patent/PT77404B/pt not_active IP Right Cessation
- 1983-09-27 CS CS837049A patent/CS247168B2/cs unknown
- 1983-09-27 NL NL8303310A patent/NL8303310A/nl not_active Application Discontinuation
- 1983-09-27 DE DE19833334937 patent/DE3334937A1/de active Granted
- 1983-09-27 GB GB08325744A patent/GB2128187B/en not_active Expired
- 1983-09-27 IL IL69824A patent/IL69824A/xx unknown
- 1983-09-27 OA OA58118A patent/OA07548A/xx unknown
- 1983-09-27 AR AR83294329A patent/AR241785A1/es active
- 1983-09-27 ES ES525983A patent/ES525983A0/es active Granted
- 1983-09-27 SE SE8305217A patent/SE461734B/sv not_active IP Right Cessation
- 1983-09-27 HU HU833351A patent/HU191066B/hu not_active IP Right Cessation
- 1983-09-27 IT IT23022/83A patent/IT1163944B/it active
- 1983-09-27 DK DK442383A patent/DK442383A/da not_active Application Discontinuation
- 1983-09-27 IE IE2266/83A patent/IE55947B1/en not_active IP Right Cessation
- 1983-09-27 NO NO833479A patent/NO163284C/no unknown
- 1983-09-28 AT AT0344983A patent/AT382621B/de not_active IP Right Cessation
- 1983-09-28 DD DD83255191A patent/DD212255A5/de not_active IP Right Cessation
- 1983-09-28 LU LU85021A patent/LU85021A1/fr unknown
- 1983-09-28 ZW ZW207/83A patent/ZW20783A1/xx unknown
- 1983-09-28 KR KR1019830004574A patent/KR890002228B1/ko not_active IP Right Cessation
- 1983-09-28 CH CH5263/83A patent/CH656130A5/de not_active IP Right Cessation
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| Date | Code | Title | Description |
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| A85 | Still pending on 85-01-01 | ||
| BA | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
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| BV | The patent application has lapsed |