DD234015A5 - Verfahren zur herstellung von 6-(subst.)-methylen-penicillan-und 6-(subst.)-hydroxymethyl-penicillansaeure und deren derivaten - Google Patents

Verfahren zur herstellung von 6-(subst.)-methylen-penicillan-und 6-(subst.)-hydroxymethyl-penicillansaeure und deren derivaten Download PDF

Info

Publication number: DD234015A5
Authority: DD; German Democratic Republic
Prior art keywords: nmr; formula; ppm; mixture; compound
Prior art date: 1984-01-30

Application number

DD272804A

Other languages

German (de)

English (en)

Inventor

Chen

Original Assignee

Pfizer

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.)

1984-01-30

Filing date

1985-01-28

Publication date

1986-03-19

1985-01-28 Application filed by Pfizer filed Critical Pfizer

1986-03-19 Publication of DD234015A5 publication Critical patent/DD234015A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 14
-1 carboxylate salt Chemical class 0.000 claims abstract description 151
150000001875 compounds Chemical class 0.000 claims abstract description 127
238000000034 method Methods 0.000 claims abstract description 88
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
239000002253 acid Substances 0.000 claims abstract description 42
150000003839 salts Chemical class 0.000 claims abstract description 25
238000002360 preparation method Methods 0.000 claims abstract description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
238000001727 in vivo Methods 0.000 claims abstract description 13
125000004185 ester group Chemical group 0.000 claims abstract description 8
230000008569 process Effects 0.000 claims abstract description 7
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 5
229920002554 vinyl polymer Polymers 0.000 claims abstract description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 82
238000006243 chemical reaction Methods 0.000 claims description 55
239000001257 hydrogen Substances 0.000 claims description 41
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 41
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 39
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 39
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 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
229910052757 nitrogen Inorganic materials 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
229910052700 potassium Inorganic materials 0.000 claims description 19
239000007858 starting material Substances 0.000 claims description 19
239000003153 chemical reaction reagent Substances 0.000 claims description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 12
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 12
229910052708 sodium Inorganic materials 0.000 claims description 12
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 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
230000003647 oxidation Effects 0.000 claims description 9
238000007254 oxidation reaction Methods 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 8
229910052763 palladium Inorganic materials 0.000 claims description 7
230000003197 catalytic effect Effects 0.000 claims description 6
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
125000005336 allyloxy 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000001624 naphthyl group Chemical group 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
239000003495 polar organic solvent Substances 0.000 claims description 2
239000012286 potassium permanganate Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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 12
239000000543 intermediate Substances 0.000 abstract description 11
150000003254 radicals Chemical class 0.000 abstract description 7
230000002401 inhibitory effect Effects 0.000 abstract description 5
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
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
125000002252 acyl 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
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 238
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 174
239000000203 mixture Substances 0.000 description 165
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 129
238000005160 1H NMR spectroscopy Methods 0.000 description 122
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 97
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 76
239000000047 product Substances 0.000 description 72
239000002904 solvent Substances 0.000 description 69
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 62
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
239000003921 oil Substances 0.000 description 37
235000019198 oils Nutrition 0.000 description 37
239000007787 solid Substances 0.000 description 37
239000003782 beta lactam antibiotic agent Substances 0.000 description 34
239000002132 β-lactam antibiotic Substances 0.000 description 34
229940124586 β-lactam antibiotics Drugs 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
150000002148 esters Chemical class 0.000 description 33
239000000741 silica gel Substances 0.000 description 32
229910002027 silica gel Inorganic materials 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
238000005481 NMR spectroscopy Methods 0.000 description 24
238000002329 infrared spectrum Methods 0.000 description 24
239000000284 extract Substances 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
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 17
230000008020 evaporation Effects 0.000 description 17
239000011591 potassium Substances 0.000 description 17
238000010992 reflux Methods 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
JMSRBKPMLUGHCR-UHFFFAOYSA-N bromohydrin Chemical compound BrC[C]1CO1 JMSRBKPMLUGHCR-UHFFFAOYSA-N 0.000 description 16
239000003054 catalyst Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
150000001299 aldehydes Chemical class 0.000 description 14
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
239000012043 crude product Substances 0.000 description 13
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
150000004678 hydrides Chemical class 0.000 description 12
238000007327 hydrogenolysis reaction Methods 0.000 description 12
229930186147 Cephalosporin Natural products 0.000 description 11
229940124587 cephalosporin Drugs 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
235000017557 sodium bicarbonate Nutrition 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
150000003457 sulfones Chemical class 0.000 description 11
150000003462 sulfoxides 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
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
239000003480 eluent Substances 0.000 description 9
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
239000000126 substance Substances 0.000 description 9
125000001424 substituent group Chemical group 0.000 description 9
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
239000006260 foam Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
229940086542 triethylamine Drugs 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
239000007800 oxidant agent Substances 0.000 description 7
229940049954 penicillin Drugs 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
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
241000699670 Mus sp. Species 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 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
230000003115 biocidal effect Effects 0.000 description 6
239000002775 capsule Substances 0.000 description 6
244000005700 microbiome Species 0.000 description 6
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 6
239000000843 powder Substances 0.000 description 6
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 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
238000001228 spectrum Methods 0.000 description 6
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000003638 chemical reducing agent Substances 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
239000011521 glass Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 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
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
238000003820 Medium-pressure liquid chromatography Methods 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
239000003795 chemical substances by application Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000000605 extraction Methods 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 4
150000004967 organic peroxy acids Chemical class 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 4
238000000746 purification Methods 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
150000003568 thioethers Chemical class 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
108020004256 Beta-lactamase Proteins 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
239000007818 Grignard reagent Substances 0.000 description 3
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BWWVAEOLVKTZFQ-ISVUSNJMSA-N chembl530 Chemical compound N(/[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)=C\N1CCCCCC1 BWWVAEOLVKTZFQ-ISVUSNJMSA-N 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
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ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
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239000013256 coordination polymer Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
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HGBLNBBNRORJKI-WCABBAIRSA-N cyclacillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C1(N)CCCCC1 HGBLNBBNRORJKI-WCABBAIRSA-N 0.000 description 1
229960004244 cyclacillin Drugs 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical class [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
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239000003814 drug Substances 0.000 description 1
RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 description 1
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OYQVQWIASIXXRT-UHFFFAOYSA-N ethyl 2,4-dioxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)=O OYQVQWIASIXXRT-UHFFFAOYSA-N 0.000 description 1
OCCIGHIQVMLYBZ-UHFFFAOYSA-N ethyl 5-methyl-1,2-oxazole-3-carboxylate Chemical compound CCOC(=O)C=1C=C(C)ON=1 OCCIGHIQVMLYBZ-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
DXVUYOAEDJXBPY-NFFDBFGFSA-N hetacillin Chemical compound C1([C@@H]2C(=O)N(C(N2)(C)C)[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 DXVUYOAEDJXBPY-NFFDBFGFSA-N 0.000 description 1
229960003884 hetacillin Drugs 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
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238000000338 in vitro Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
ZKUKMWMSYCIYRD-ZXFNITATSA-N lenampicillin Chemical compound O1C(=O)OC(COC(=O)[C@H]2C(S[C@H]3N2C([C@H]3NC(=O)[C@H](N)C=2C=CC=CC=2)=O)(C)C)=C1C ZKUKMWMSYCIYRD-ZXFNITATSA-N 0.000 description 1
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230000001665 lethal effect Effects 0.000 description 1
YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
QTQPGZVDUCMVLK-ZXFNITATSA-N methoxymethyl (2s,5r,6r)-6-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound C1([C@@H]2C(=O)N(C(N2)(C)C)[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC)=CC=CC=C1 QTQPGZVDUCMVLK-ZXFNITATSA-N 0.000 description 1
HQOQSFITXGQQDM-SSDOTTSWSA-N methyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound COC(=O)C1=CCS[C@@H]2CC(=O)N12 HQOQSFITXGQQDM-SSDOTTSWSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
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AZFQCTBZOPUVOW-UHFFFAOYSA-N methyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 AZFQCTBZOPUVOW-UHFFFAOYSA-N 0.000 description 1
CREBIKHUZHBYJU-UHFFFAOYSA-M methylsulfanylmethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CSC)C1=CC=CC=C1 CREBIKHUZHBYJU-UHFFFAOYSA-M 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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YPBATNHYBCGSSN-VWPFQQQWSA-N mezlocillin Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC=CC=1)C(=O)N1CCN(S(C)(=O)=O)C1=O YPBATNHYBCGSSN-VWPFQQQWSA-N 0.000 description 1
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235000010446 mineral oil Nutrition 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
NONJJLVGHLVQQM-JHXYUMNGSA-N phenethicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C)OC1=CC=CC=C1 NONJJLVGHLVQQM-JHXYUMNGSA-N 0.000 description 1
229960004894 pheneticillin Drugs 0.000 description 1
JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
229960002292 piperacillin Drugs 0.000 description 1
WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 1
229950004791 pirbenicillin Drugs 0.000 description 1
ZEMIJUDPLILVNQ-ZXFNITATSA-N pivampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC(=O)C(C)(C)C)=CC=CC=C1 ZEMIJUDPLILVNQ-ZXFNITATSA-N 0.000 description 1
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229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940072033 potash Drugs 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
DXBWJLDFSICTIH-UHFFFAOYSA-N pyrazine-2-carbaldehyde Chemical compound O=CC1=CN=CC=N1 DXBWJLDFSICTIH-UHFFFAOYSA-N 0.000 description 1
TXJKATOSKLUITR-UHFFFAOYSA-N pyrazine-2-carbonyl chloride Chemical compound ClC(=O)C1=CN=CC=N1 TXJKATOSKLUITR-UHFFFAOYSA-N 0.000 description 1
NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
OKULHRWWYCFJAB-UHFFFAOYSA-N pyrimidine-4-carbaldehyde Chemical compound O=CC1=CC=NC=N1 OKULHRWWYCFJAB-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000003362 replicative effect Effects 0.000 description 1
238000012958 reprocessing Methods 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
XMNFWSAYWSUJMH-ZXFNITATSA-N sarmoxicillin Chemical compound C1([C@@H]2C(=O)N(C(N2)(C)C)[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC)=CC=C(O)C=C1 XMNFWSAYWSUJMH-ZXFNITATSA-N 0.000 description 1
229950004779 sarmoxicillin Drugs 0.000 description 1
229950002532 sarpicillin Drugs 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000008259 solid foam Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical class [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
229950007949 suncillin Drugs 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
SOROUYSPFADXSN-SUWVAFIASA-N talampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OC2C3=CC=CC=C3C(=O)O2)(C)C)=CC=CC=C1 SOROUYSPFADXSN-SUWVAFIASA-N 0.000 description 1
229960002780 talampicillin Drugs 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
229960004659 ticarcillin Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
KAYCSCULGYYNFT-UHFFFAOYSA-N triphenyl(pyridin-2-ylmethyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=N1 KAYCSCULGYYNFT-UHFFFAOYSA-N 0.000 description 1
IUNXOGIHFLDANL-UHFFFAOYSA-M triphenyl(pyridin-2-ylmethyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=N1 IUNXOGIHFLDANL-UHFFFAOYSA-M 0.000 description 1
NFHRNKANAAGQOH-UHFFFAOYSA-N triphenylstannane Chemical compound C1=CC=CC=C1[SnH](C=1C=CC=CC=1)C1=CC=CC=C1 NFHRNKANAAGQOH-UHFFFAOYSA-N 0.000 description 1
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)

DD272804A 1984-01-30 1985-01-28 Verfahren zur herstellung von 6-(subst.)-methylen-penicillan-und 6-(subst.)-hydroxymethyl-penicillansaeure und deren derivaten DD234015A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US57535484A	1984-01-30	1984-01-30

Publications (1)

Publication Number	Publication Date
DD234015A5 true DD234015A5 (de)	1986-03-19

Family

ID=24299979

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
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
DD85286332A DD247677A5 (de)	1984-01-30	1985-01-28	Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymehtylpenicillansaeure und deren derivaten
DD85286333A DD247678A5 (de)	1984-01-30	1985-01-28	Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymethylpenicillansaeure 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
DD85286333A DD247678A5 (de)	1984-01-30	1985-01-28	Verfahren zur herstellung von 6-(subst.)-methylenpenicillan- und 6-(subst.)-hydroxymethylpenicillansaeure und deren derivaten

Country Status (15)

Country	Link
JP (1)	JPS61109791A (pl)
KR (1)	KR880001029B1 (pl)
CS (5)	CS248749B2 (pl)
DD (3)	DD234015A5 (pl)
EG (1)	EG16904A (pl)
ES (5)	ES8604972A1 (pl)
FI (1)	FI85376C (pl)
HU (2)	HU194567B (pl)
IL (1)	IL74190A (pl)
NO (1)	NO165594C (pl)
PL (5)	PL149797B1 (pl)
PT (1)	PT79893B (pl)
SU (4)	SU1395144A3 (pl)
YU (5)	YU44770B (pl)
ZA (1)	ZA85682B (pl)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3869630D1 (de) *	1987-01-27	1992-05-07	Pfizer	6-beta(substituierte)-(s)-hydroxymethylpenicillansaeure und deren derivate.
WO1999033838A1 (en)	1997-12-29	1999-07-08	Research Corporation Technologies, Inc.	2-β-SUBSTITUTED-6-ALKYLIDENE PENICILLANIC ACID DERIVATIVES AS β-LACTAMASE INHIBITORS
US6407091B1 (en)	1999-04-15	2002-06-18	Research Corporation Technologies, Inc.	β-lactamase inhibiting compounds
WO2003020732A2 (en)	2001-07-24	2003-03-13	Alamx, L.L.C.	7-alkylidene-3-substituted-3-cephem-4-carboxylates as beta-lactamase inhibitors.
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)

* Cited by examiner, † Cited by third party
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 DD272804A patent/DD234015A5/de unknown
- 1985-01-28 ES ES539890A patent/ES8604972A1/es not_active Expired
- 1985-01-28 PT PT79893A patent/PT79893B/pt not_active IP Right Cessation
- 1985-01-28 DD DD85286332A patent/DD247677A5/de unknown
- 1985-01-28 DD DD85286333A patent/DD247678A5/de unknown
- 1985-01-28 SU SU853844124A patent/SU1395144A3/ru active
- 1985-01-29 PL PL1985256016A patent/PL149797B1/pl unknown
- 1985-01-29 IL IL74190A patent/IL74190A/xx unknown
- 1985-01-29 FI FI850375A patent/FI85376C/fi not_active IP Right Cessation
- 1985-01-29 PL PL1985256014A patent/PL145990B1/pl unknown
- 1985-01-29 CS CS856935A patent/CS248749B2/cs unknown
- 1985-01-29 ZA ZA85682A patent/ZA85682B/xx 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 CS CS85619A patent/CS248733B2/cs unknown
- 1985-01-29 HU HU85759A patent/HU194891B/hu not_active IP Right Cessation
- 1985-01-29 PL PL1985256013A patent/PL149242B1/pl unknown
- 1985-01-29 KR KR1019850000547A patent/KR880001029B1/ko not_active Expired
- 1985-01-29 CS CS856933A patent/CS248747B2/cs unknown
- 1985-01-29 PL PL1985256015A patent/PL147514B1/pl unknown
- 1985-01-29 PL PL1985251750A patent/PL145130B1/pl unknown
- 1985-01-29 NO NO850350A patent/NO165594C/no unknown
- 1985-01-29 CS CS856934A patent/CS248748B2/cs unknown
- 1985-01-30 JP JP60016368A patent/JPS61109791A/ja active Pending
- 1985-01-30 YU YU140/85A patent/YU44770B/xx unknown
- 1985-10-31 ES ES548429A patent/ES8704952A1/es not_active Expired
- 1985-10-31 ES ES548428A patent/ES8702916A1/es not_active Expired
- 1985-10-31 ES ES548427A patent/ES8705451A1/es not_active Expired
- 1985-10-31 ES ES548426A patent/ES8700860A1/es not_active Expired
1986
- 1986-03-17 SU SU864027136A patent/SU1503683A3/ru active
- 1986-03-17 SU SU864027101A patent/SU1508961A3/ru active
- 1986-03-17 SU SU864027223A patent/SU1396969A3/ru active
1987
- 1987-06-25 YU YU1195/87A patent/YU44635B/xx unknown
- 1987-06-25 YU YU1196/87A patent/YU44805B/xx unknown
- 1987-06-25 YU YU1194/87A patent/YU44634B/xx unknown
- 1987-06-25 YU YU1197/87A patent/YU44636B/xx unknown

Also Published As

Publication number	Publication date
PL256013A1 (en)	1986-10-21
ES8604972A1 (es)	1986-02-16
FI850375A0 (fi)	1985-01-29
IL74190A (en)	1989-09-28
ES8704952A1 (es)	1987-04-16
ES548427A0 (es)	1987-05-01
KR850005445A (ko)	1985-08-26
ES8705451A1 (es)	1987-05-01
PL149242B1 (en)	1990-01-31
ES548429A0 (es)	1987-04-16
CS248746B2 (en)	1987-02-12
ES8702916A1 (es)	1987-01-16
ES8700860A1 (es)	1986-11-16
NO165594C (no)	1991-03-06
PL256014A1 (en)	1986-12-02
YU44805B (en)	1991-02-28
HU194891B (en)	1988-03-28
PL251750A1 (en)	1985-12-17
YU44634B (en)	1990-10-31
PT79893B (en)	1987-02-03
HU194567B (en)	1988-02-29
YU44770B (en)	1991-02-28
NO850350L (no)	1985-07-31
ES548426A0 (es)	1986-11-16
YU44635B (en)	1990-10-31
SU1395144A3 (ru)	1988-05-07
YU119487A (en)	1988-02-29
YU119587A (en)	1988-02-29
DD247678A5 (de)	1987-07-15
CS248747B2 (en)	1987-02-12
HUT40443A (en)	1986-12-28
ES548428A0 (es)	1987-01-16
NO165594B (no)	1990-11-26
ZA85682B (en)	1986-09-24
FI850375L (fi)	1985-07-31
CS248733B2 (en)	1987-02-12
PL145990B1 (en)	1988-12-31
ES539890A0 (es)	1986-02-16
SU1503683A3 (ru)	1989-08-23
DD247677A5 (de)	1987-07-15
PL149797B1 (en)	1990-03-31
PL145130B1 (en)	1988-08-31
PT79893A (en)	1985-02-01
PL256015A1 (en)	1986-11-18
HUT37799A (en)	1986-02-28
IL74190A0 (en)	1985-04-30
CS248749B2 (en)	1987-02-12
JPS61109791A (ja)	1986-05-28
FI85376B (fi)	1991-12-31
YU119787A (en)	1988-04-30
YU44636B (en)	1990-10-31
SU1396969A3 (ru)	1988-05-15
PL256016A1 (en)	1986-12-02
YU14085A (en)	1987-12-31
KR880001029B1 (ko)	1988-06-15
EG16904A (en)	1992-06-30
PL147514B1 (en)	1989-06-30
CS248748B2 (en)	1987-02-12
SU1508961A3 (ru)	1989-09-15
FI85376C (fi)	1992-04-10
YU119687A (en)	1988-04-30

Legal Events

Date	Code	Title	Description
1994-04-14	NPV	Change in the person, the name or the address of the representative (addendum to changes before extension act)

Publication	Publication Date	Title
US4287181A (en)	1981-09-01	Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors
DE3404615C2 (pl)	1989-06-15
US4217453A (en)	1980-08-12	6-Amido-3-substituted-amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acid
DE2824535B2 (de)	1980-05-14	Penkillansäure-l.l-dioxide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2356388A1 (de)	1974-05-22	Cephalosporine und verfahren zu ihrer herstellung
US4826833A (en)	1989-05-02	6-(Substituted)methylene-penicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
DE3008316C2 (de)	1982-12-16	6-&beta;-Jodpenicillansäure-Derivate, Verfahren zu ihrer Herstellung und solche Derivate enthaltende Arzneimittel
DD234015A5 (de)	1986-03-19	Verfahren zur herstellung von 6-(subst.)-methylen-penicillan-und 6-(subst.)-hydroxymethyl-penicillansaeure und deren derivaten
EP0150984B1 (en)	1991-09-11	6-(substituted) methylenepenicillanic and 6-(substituted) hydroxymethylpenicillanic acids and derivatives thereof
AT395590B (de)	1993-01-25	2-methoxymethylpenemverbindungen, verfahren zu deren herstellung und sie enthaltende pharmazeutische zusammensetzungen
US4298741A (en)	1981-11-03	6-Amido-3-substituted-1-azabicyclo[3.2.0]-hept-2-en-7-one-2-carboxylic acid
DE3201957A1 (de)	1982-09-09	Derivate der 7-oxo-1-azabicyclo-(3.2.0)-hept-2-en-2-carbonsaeure
DE3317742C2 (pl)	1991-08-29
DE4019960C2 (de)	2001-06-07	Neue Penamderivate und deren Salze, Verfahren zu ihrer Herstellung und antibakterielles Mittel mit einem Gehalt derselben
US5015473A (en)	1991-05-14	6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof
US4521533A (en)	1985-06-04	Salts of 6-alpha-(aminomethyl)penicillanic acid 1,1-dioxide esters and beta-lactam antibiotics
US4656263A (en)	1987-04-07	6-β-substituted penicillanic acid compound free of the 6-α-epimer
DE3231596A1 (de)	1983-03-10	Penem-3-carbonsaeurederivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen
US4762921A (en)	1988-08-09	6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives
DD218365A5 (de)	1985-02-06	Verfahren zur herstellung von 6-aminomethylpenicillansaeure-1,1-dioxid-derivaten als beta-lactamase-inhibitoren
US4675186A (en)	1987-06-23	6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives
US4431654A (en)	1984-02-14	6-(Hydroxyethyl)-2-[(heterocyclyl or aryl)thioalkylthio]-penem-3-carboxylates
DE69130363T2 (de)	1999-04-22	Antibakterielle penemverbindungen
US4518530A (en)	1985-05-21	6-β-Substituted penicillanic acids as β-lactamase inhibitors
US4427678A (en)	1984-01-24	6-Aminomethylpenicillanic acid 1,1-dioxide derivatives as beta-lactamase inhibitors