DD247678A5 - Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymethylpenicillansaeure und deren derivaten - Google Patents
Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymethylpenicillansaeure und deren derivaten Download PDFInfo
- Publication number
- DD247678A5 DD247678A5 DD85286333A DD28633385A DD247678A5 DD 247678 A5 DD247678 A5 DD 247678A5 DD 85286333 A DD85286333 A DD 85286333A DD 28633385 A DD28633385 A DD 28633385A DD 247678 A5 DD247678 A5 DD 247678A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- nmr
- ppm
- mixture
- allyl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 15
- -1 carboxylate salt Chemical class 0.000 claims abstract description 150
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 238000000034 method Methods 0.000 claims abstract description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 48
- 239000002253 acid Substances 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 238000001727 in vivo Methods 0.000 claims abstract description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 125000004185 ester group Chemical group 0.000 claims abstract description 8
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 84
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
- 239000002904 solvent Substances 0.000 claims description 71
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 64
- 238000006243 chemical reaction Methods 0.000 claims description 56
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 42
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 41
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
- 239000011734 sodium Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052700 potassium Inorganic materials 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- 239000007858 starting material Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000004678 hydrides Chemical class 0.000 claims description 13
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 13
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 13
- 229910052708 sodium Inorganic materials 0.000 claims description 11
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 10
- 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 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 claims description 7
- 230000003197 catalytic effect Effects 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 4
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 150000001262 acyl bromides Chemical class 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims 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 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 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 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
- 125000000972 4,5-dimethylthiazol-2-yl group Chemical group [H]C([H])([H])C1=C(N=C(*)S1)C([H])([H])[H] 0.000 claims 1
- FYMYQYLZCXHPCY-UHFFFAOYSA-N 4-(3-piperidin-1-yl-3-pyrrolidin-1-ylthiomorpholin-4-yl)morpholine Chemical compound N1(CCCC1)C1(N(CCSC1)N1CCOCC1)N1CCCCC1 FYMYQYLZCXHPCY-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 11
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 246
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 174
- 239000000203 mixture Substances 0.000 description 166
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 143
- 238000005160 1H NMR spectroscopy Methods 0.000 description 123
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- 229940093499 ethyl acetate Drugs 0.000 description 82
- 235000019439 ethyl acetate Nutrition 0.000 description 82
- 239000000243 solution Substances 0.000 description 76
- 239000000047 product Substances 0.000 description 71
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 239000003921 oil Substances 0.000 description 38
- 235000019198 oils Nutrition 0.000 description 38
- 239000007787 solid Substances 0.000 description 38
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 36
- 230000000875 corresponding effect Effects 0.000 description 36
- 239000002132 β-lactam antibiotic Substances 0.000 description 36
- 229940124586 β-lactam antibiotics Drugs 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
- 150000002148 esters Chemical class 0.000 description 32
- 239000000741 silica gel Substances 0.000 description 32
- 229910002027 silica gel Inorganic materials 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000002329 infrared spectrum Methods 0.000 description 25
- 239000000284 extract Substances 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 239000010410 layer Substances 0.000 description 21
- 239000012044 organic layer Substances 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 18
- 238000010898 silica gel chromatography Methods 0.000 description 18
- JMSRBKPMLUGHCR-UHFFFAOYSA-N bromohydrin Chemical compound BrC[C]1CO1 JMSRBKPMLUGHCR-UHFFFAOYSA-N 0.000 description 17
- 230000008020 evaporation Effects 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 16
- 239000011591 potassium Substances 0.000 description 16
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- 229930186147 Cephalosporin Natural products 0.000 description 12
- 229930182555 Penicillin Natural products 0.000 description 12
- 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 12
- 102000006635 beta-lactamase Human genes 0.000 description 12
- 229940124587 cephalosporin Drugs 0.000 description 12
- 150000003462 sulfoxides Chemical class 0.000 description 12
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 150000001780 cephalosporins Chemical class 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 150000003457 sulfones Chemical class 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 10
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 108090000204 Dipeptidase 1 Proteins 0.000 description 9
- 239000003781 beta lactamase inhibitor Substances 0.000 description 9
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000006260 foam Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 230000000844 anti-bacterial effect Effects 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000007800 oxidant agent Substances 0.000 description 7
- 229940049954 penicillin Drugs 0.000 description 7
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- 208000035143 Bacterial infection Diseases 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 208000022362 bacterial infectious disease Diseases 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000003115 biocidal effect Effects 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000002960 penicillins Chemical class 0.000 description 5
- 159000000001 potassium salts Chemical class 0.000 description 5
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 150000003952 β-lactams Chemical group 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- ZGTFNNUASMWGTM-UHFFFAOYSA-N 1,3-thiazole-2-carbaldehyde Chemical compound O=CC1=NC=CS1 ZGTFNNUASMWGTM-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 4
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57535484A | 1984-01-30 | 1984-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD247678A5 true DD247678A5 (de) | 1987-07-15 |
Family
ID=24299979
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85286333A DD247678A5 (de) | 1984-01-30 | 1985-01-28 | Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymethylpenicillansaeure und deren derivaten |
| DD85286332A DD247677A5 (de) | 1984-01-30 | 1985-01-28 | Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymehtylpenicillansaeure und deren derivaten |
| DD272804A DD234015A5 (de) | 1984-01-30 | 1985-01-28 | Verfahren zur herstellung von 6-(subst.)-methylen-penicillan-und 6-(subst.)-hydroxymethyl-penicillansaeure und deren derivaten |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85286332A DD247677A5 (de) | 1984-01-30 | 1985-01-28 | Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymehtylpenicillansaeure und deren derivaten |
| DD272804A DD234015A5 (de) | 1984-01-30 | 1985-01-28 | Verfahren zur herstellung von 6-(subst.)-methylen-penicillan-und 6-(subst.)-hydroxymethyl-penicillansaeure und deren derivaten |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS61109791A (cs) |
| KR (1) | KR880001029B1 (cs) |
| CS (5) | CS248749B2 (cs) |
| DD (3) | DD247678A5 (cs) |
| EG (1) | EG16904A (cs) |
| ES (5) | ES8604972A1 (cs) |
| FI (1) | FI85376C (cs) |
| HU (2) | HU194891B (cs) |
| IL (1) | IL74190A (cs) |
| NO (1) | NO165594C (cs) |
| PL (5) | PL149797B1 (cs) |
| PT (1) | PT79893B (cs) |
| SU (4) | SU1395144A3 (cs) |
| YU (5) | YU44770B (cs) |
| ZA (1) | ZA85682B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0276942B1 (en) * | 1987-01-27 | 1992-04-01 | Pfizer Inc. | 6-beta(substituted)-(s)-hydroxymethylpenicillanic acids and derivatives thereof |
| ATE219085T1 (de) | 1997-12-29 | 2002-06-15 | Res Corp Technologies Inc | 2-beta-substituierte-6-alkylidenpenizillansäure derivate als beta-laktamase inhibitoren |
| US6407091B1 (en) | 1999-04-15 | 2002-06-18 | Research Corporation Technologies, Inc. | β-lactamase inhibiting compounds |
| ATE339424T1 (de) | 2001-07-24 | 2006-10-15 | Univ Southern Methodist | 3-substituierte 7-alkylidene-3-cephem-4- carbonsäuren als beta-lactamase inhibitoren |
| AU2003224874A1 (en) | 2002-04-04 | 2003-10-27 | Alamx, L.L.C. | INHIBITORS OF SERINE AND METALLO-ss-LACTAMASES |
| GB0711776D0 (en) * | 2007-06-18 | 2007-07-25 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
| JP6183053B2 (ja) * | 2012-08-22 | 2017-08-23 | 宇部興産株式会社 | テトラヒドロピラニルピリミジン化合物の製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4272439A (en) * | 1978-06-02 | 1981-06-09 | Schering Corporation | 6-(Substituted-hydroxymethylene penams) |
| DE2927004A1 (de) * | 1979-07-04 | 1981-05-27 | Bayer Ag, 5090 Leverkusen | Penicillansaeure-1,1-dioxide, ihre herstellung und ihre verwendung als arzneimittel als arzneimittel |
| US4287181A (en) * | 1979-10-22 | 1981-09-01 | Pfizer Inc. | Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors |
-
1985
- 1985-01-28 DD DD85286333A patent/DD247678A5/de unknown
- 1985-01-28 PT PT79893A patent/PT79893B/pt not_active IP Right Cessation
- 1985-01-28 SU SU853844124A patent/SU1395144A3/ru active
- 1985-01-28 ES ES539890A patent/ES8604972A1/es not_active Expired
- 1985-01-28 DD DD85286332A patent/DD247677A5/de unknown
- 1985-01-28 DD DD272804A patent/DD234015A5/de unknown
- 1985-01-29 PL PL1985256016A patent/PL149797B1/pl unknown
- 1985-01-29 PL PL1985256014A patent/PL145990B1/pl unknown
- 1985-01-29 CS CS856935A patent/CS248749B2/cs unknown
- 1985-01-29 HU HU85759A patent/HU194891B/hu not_active IP Right Cessation
- 1985-01-29 IL IL74190A patent/IL74190A/xx unknown
- 1985-01-29 PL PL1985251750A patent/PL145130B1/pl unknown
- 1985-01-29 NO NO850350A patent/NO165594C/no unknown
- 1985-01-29 PL PL1985256015A patent/PL147514B1/pl unknown
- 1985-01-29 CS CS856933A patent/CS248747B2/cs unknown
- 1985-01-29 PL PL1985256013A patent/PL149242B1/pl unknown
- 1985-01-29 CS CS856934A patent/CS248748B2/cs unknown
- 1985-01-29 EG EG54/85A patent/EG16904A/xx active
- 1985-01-29 HU HU85322A patent/HU194567B/hu not_active IP Right Cessation
- 1985-01-29 CS CS856932A patent/CS248746B2/cs unknown
- 1985-01-29 ZA ZA85682A patent/ZA85682B/xx unknown
- 1985-01-29 KR KR1019850000547A patent/KR880001029B1/ko not_active Expired
- 1985-01-29 FI FI850375A patent/FI85376C/fi not_active IP Right Cessation
- 1985-01-29 CS CS85619A patent/CS248733B2/cs unknown
- 1985-01-30 YU YU140/85A patent/YU44770B/xx unknown
- 1985-01-30 JP JP60016368A patent/JPS61109791A/ja active Pending
- 1985-10-31 ES ES548427A patent/ES8705451A1/es not_active Expired
- 1985-10-31 ES ES548429A patent/ES8704952A1/es not_active Expired
- 1985-10-31 ES ES548426A patent/ES8700860A1/es not_active Expired
- 1985-10-31 ES ES548428A patent/ES8702916A1/es not_active Expired
-
1986
- 1986-03-17 SU SU864027136A patent/SU1503683A3/ru active
- 1986-03-17 SU SU864027223A patent/SU1396969A3/ru active
- 1986-03-17 SU SU864027101A patent/SU1508961A3/ru active
-
1987
- 1987-06-25 YU YU1195/87A patent/YU44635B/xx unknown
- 1987-06-25 YU YU1197/87A patent/YU44636B/xx unknown
- 1987-06-25 YU YU1194/87A patent/YU44634B/xx unknown
- 1987-06-25 YU YU1196/87A patent/YU44805B/xx unknown
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NPV | Change in the person, the name or the address of the representative (addendum to changes before extension act) |