CH535787A - Verfahren zur Herstellung wasserlöslicher Salze von a-Aminobenzylpenicillin - Google Patents

Verfahren zur Herstellung wasserlöslicher Salze von a-Aminobenzylpenicillin

Info

Publication number: CH535787A
Authority: CH; Switzerland
Prior art keywords: sodium; salt; solution; methylene chloride; potassium
Prior art date: 1967-08-18

Application number

CH1227468A

Other languages

German (de)

English (en)

Inventor

D Kanter Gerald

Original Assignee

Beecham Inc

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.)

1967-08-18

Filing date

1968-08-15

Publication date

1973-04-15

1968-08-15 Application filed by Beecham Inc filed Critical Beecham Inc

1973-04-15 Publication of CH535787A publication Critical patent/CH535787A/de

Links

150000003839 salts Chemical class 0.000 title claims abstract description 12
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical class C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 title claims description 26
230000000844 anti-bacterial effect Effects 0.000 title description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 107
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 36
238000000034 method Methods 0.000 claims abstract description 21
-1 amine salt Chemical class 0.000 claims abstract description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
150000001447 alkali salts Chemical class 0.000 claims abstract description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims abstract description 6
239000002904 solvent Substances 0.000 claims abstract description 6
229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 5
235000011152 sodium sulphate Nutrition 0.000 claims abstract description 5
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 claims abstract description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 15
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 15
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 13
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 12
235000019341 magnesium sulphate Nutrition 0.000 claims description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
239000002244 precipitate Substances 0.000 claims description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
239000003513 alkali Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
235000009518 sodium iodide Nutrition 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
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 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 4
150000003335 secondary amines Chemical class 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
150000003112 potassium compounds Chemical class 0.000 claims description 3
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
150000003141 primary amines Chemical class 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
235000010344 sodium nitrate Nutrition 0.000 claims description 2
239000004317 sodium nitrate Substances 0.000 claims description 2
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 3
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 2
230000001419 dependent effect Effects 0.000 claims 1
229910017053 inorganic salt Inorganic materials 0.000 claims 1
235000007715 potassium iodide Nutrition 0.000 claims 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
235000010333 potassium nitrate Nutrition 0.000 claims 1
239000004323 potassium nitrate Substances 0.000 claims 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims 1
ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000010626 work up procedure Methods 0.000 claims 1
229930182555 Penicillin Natural products 0.000 abstract description 3
150000001412 amines Chemical class 0.000 abstract description 3
239000007832 Na2SO4 Substances 0.000 abstract description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract description 2
229940049954 penicillin Drugs 0.000 abstract description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
229910052783 alkali metal Inorganic materials 0.000 abstract 1
239000003242 anti bacterial agent Substances 0.000 abstract 1
229940088710 antibiotic agent Drugs 0.000 abstract 1
239000001110 calcium chloride Substances 0.000 abstract 1
229910001628 calcium chloride Inorganic materials 0.000 abstract 1
235000011148 calcium chloride Nutrition 0.000 abstract 1
150000007942 carboxylates Chemical class 0.000 abstract 1
125000004122 cyclic group Chemical group 0.000 abstract 1
150000002960 penicillins Chemical class 0.000 abstract 1
239000000243 solution Substances 0.000 description 40
159000000000 sodium salts Chemical class 0.000 description 17
239000000706 filtrate Substances 0.000 description 13
229960000723 ampicillin Drugs 0.000 description 12
239000000047 product Substances 0.000 description 10
229960003311 ampicillin trihydrate Drugs 0.000 description 9
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
238000003756 stirring Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000002274 desiccant Substances 0.000 description 6
239000012065 filter cake Substances 0.000 description 6
239000002002 slurry Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 5
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 4
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
238000005406 washing Methods 0.000 description 4
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
229910052925 anhydrite Inorganic materials 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
QCUOBSQYDGUHHT-UHFFFAOYSA-L cadmium sulfate Chemical compound [Cd+2].[O-]S([O-])(=O)=O QCUOBSQYDGUHHT-UHFFFAOYSA-L 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
XVLKGNGMTHJRLV-UHFFFAOYSA-N dichloromethane;n-ethylethanamine Chemical compound ClCCl.CCNCC XVLKGNGMTHJRLV-UHFFFAOYSA-N 0.000 description 2
YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
SQQMAOCOWKFBNP-UHFFFAOYSA-L manganese(II) sulfate Chemical compound [Mn+2].[O-]S([O-])(=O)=O SQQMAOCOWKFBNP-UHFFFAOYSA-L 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000003791 organic solvent mixture Substances 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
229910000368 zinc sulfate Inorganic materials 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
PSJBSUHYCGQTHZ-UHFFFAOYSA-N 3-Methoxy-1,2-propanediol Chemical compound COCC(O)CO PSJBSUHYCGQTHZ-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
NRXDHTYIDMALNV-UHFFFAOYSA-N C(C)(=O)OC.ClC1=CC=CC=C1 Chemical compound C(C)(=O)OC.ClC1=CC=CC=C1 NRXDHTYIDMALNV-UHFFFAOYSA-N 0.000 description 1
WWJZTGWTGCUXDX-UHFFFAOYSA-N CC(C)=O.NCCN Chemical compound CC(C)=O.NCCN WWJZTGWTGCUXDX-UHFFFAOYSA-N 0.000 description 1
GNLLBERBQYWUPK-UHFFFAOYSA-N CN(C=O)C.C(CN)N Chemical compound CN(C=O)C.C(CN)N GNLLBERBQYWUPK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
239000005700 Putrescine Substances 0.000 description 1
206010041277 Sodium retention Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
IDVJXKFJHUNVNB-UHFFFAOYSA-N acetonitrile;n-ethylethanamine Chemical compound CC#N.CCNCC IDVJXKFJHUNVNB-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000331 cadmium sulfate Inorganic materials 0.000 description 1
229910000369 cadmium(II) sulfate Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
YALYLPKSKBQFJP-UHFFFAOYSA-N chloroform;n-ethylethanamine Chemical compound ClC(Cl)Cl.CCNCC YALYLPKSKBQFJP-UHFFFAOYSA-N 0.000 description 1
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
AKZDNULBDQAHFW-UHFFFAOYSA-N dichloromethane propan-1-amine Chemical compound ClCCl.C(CC)N AKZDNULBDQAHFW-UHFFFAOYSA-N 0.000 description 1
HKWFAZSUNAPEPD-UHFFFAOYSA-N dichloromethane;pyrrolidine Chemical compound ClCCl.C1CCNC1 HKWFAZSUNAPEPD-UHFFFAOYSA-N 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229940099596 manganese sulfate Drugs 0.000 description 1
239000011702 manganese sulphate Substances 0.000 description 1
235000007079 manganese sulphate Nutrition 0.000 description 1
229910000357 manganese(II) sulfate Inorganic materials 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229960001763 zinc sulfate Drugs 0.000 description 1
239000011686 zinc sulphate Substances 0.000 description 1
235000009529 zinc sulphate Nutrition 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cephalosporin Compounds (AREA)

CH1227468A 1967-08-18 1968-08-15 Verfahren zur Herstellung wasserlöslicher Salze von a-Aminobenzylpenicillin CH535787A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US66155367A	1967-08-18	1967-08-18

Publications (1)

Publication Number	Publication Date
CH535787A true CH535787A (de)	1973-04-15

Family

ID=24654095

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1227468A CH535787A (de)	1967-08-18	1968-08-15	Verfahren zur Herstellung wasserlöslicher Salze von a-Aminobenzylpenicillin

Country Status (11)

Country	Link
AT (1)	AT289295B (da)
BE (1)	BE719598A (da)
CH (1)	CH535787A (da)
DE (1)	DE1795129C3 (da)
DK (1)	DK132027C (da)
ES (1)	ES357308A1 (da)
FI (1)	FI51195B (da)
FR (1)	FR1590145A (da)
IE (1)	IE32238B1 (da)
NL (1)	NL6811323A (da)
SE (1)	SE375534B (da)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1286199A (en) *	1970-03-16	1972-08-23	Beecham Group Ltd	Penicillins
GB1464026A (en) *	1974-09-25	1977-02-09	Beecham Group Ltd	Preparation of beta-lactam antibiotics
DE9106950U1 (de) *	1991-06-06	1992-06-04	Hand, Martin, 8900 Augsburg	Türklinkensicherung
DE4403622C2 (de) *	1994-02-05	1997-09-18	Michael Fleischmann	Türschloß

1968
- 1968-08-02 IE IE93968A patent/IE32238B1/xx unknown
- 1968-08-08 NL NL6811323A patent/NL6811323A/xx unknown
- 1968-08-13 FR FR1590145D patent/FR1590145A/fr not_active Expired
- 1968-08-14 DE DE19681795129 patent/DE1795129C3/de not_active Expired
- 1968-08-14 SE SE1097368A patent/SE375534B/xx unknown
- 1968-08-15 DK DK395168A patent/DK132027C/da active
- 1968-08-15 CH CH1227468A patent/CH535787A/de not_active IP Right Cessation
- 1968-08-16 BE BE719598D patent/BE719598A/xx not_active IP Right Cessation
- 1968-08-16 ES ES357308A patent/ES357308A1/es not_active Expired
- 1968-08-16 FI FI232068A patent/FI51195B/fi active
- 1968-08-16 AT AT801268A patent/AT289295B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE32238L (en)	1969-02-18
BE719598A (da)	1969-02-17
SE375534B (da)	1975-04-21
FR1590145A (da)	1970-04-13
ES357308A1 (es)	1970-11-01
DE1795129A1 (de)	1972-01-05
DK132027C (da)	1976-03-01
FI51195B (da)	1976-08-02
DE1795129C3 (de)	1979-01-11
DE1795129B2 (de)	1978-05-11
AT289295B (de)	1971-04-13
IE32238B1 (en)	1973-05-30
NL6811323A (da)	1969-02-20
DK132027B (da)	1975-10-13

Legal Events

Date	Code	Title	Description
1979-05-15	PL	Patent ceased

Publication	Publication Date	Title
DE3345989C2 (da)	1992-09-24
DE819093C (de)	1951-10-29	Verfahren zur Herstellung von Thyroxin und seinen Derivaten
DE1670600A1 (de)	1970-08-06	Verfahren zur Herstellung neuer Cephalosporinverbindungen mit antibiotischer Wirksamkeit
CH535787A (de)	1973-04-15	Verfahren zur Herstellung wasserlöslicher Salze von a-Aminobenzylpenicillin
DE1670222C3 (de)	1979-04-05	a-(Benzyloxycarbonyl)-thienyunethylpenicilline und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende antibakterielle Mittel
DE1143817C2 (de)	1973-03-29	Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben
CH492737A (de)	1970-06-30	Verfahren zur Herstellung von Cephalosporin-CA-Antibiotica
DE1670163C3 (de)	1973-11-29	Cephaloglycindenvat und Verfahren zu seiner Herstellung
DE2814974A1 (de)	1978-10-19	Neue n hoch 2 -t-butyl-11a-halo-6-demethyl-6-desoxy-6-methylen-tetracycline und verfahren zu ihrer herstellung
DE1924760B2 (de)	1974-09-12	Penicillinderivate und Verfahren zu deren Herstellung sowie antibakterielles Arzneimittel
DE1545530A1 (de)	1969-07-10	Verfahren zur Herstellung antimikrobiell aktiver Verbindungen
DE1933629C3 (de)	1975-07-31	alpha-Substituierte Benzylpenicilline und Verfahren zu deren Herstellung
DE3135728C2 (de)	1994-09-22	Verfahren zur Herstellung von Apovincaminsäureestern
DE1931097C3 (de)	1975-05-07	Verfahren zur Herstellung von 6-Isocyana to- penicillansäure derivaten
AT336572B (de)	1977-05-10	Verfahren zur herstellung von neuen alkylsulfonylaminoglycinen sowie deren salzen
DE1470083C (de)	1972-08-24	Cinnamylpenicilline und Verfahren zu ihrer Herstellung
DE2449711C3 (de)	1980-08-21	Verfahren zur Herstellung von Asparagin und N-Acetyl-asparagin
DE850297C (de)	1952-09-22	Verfahren zur Herstellung von Amidinsalzen
AT232196B (de)	1964-03-10	Verfahren zur Herstellung von Penicillinen
AT337366B (de)	1977-06-27	Verfahren zur herstellung von neuen derivaten des cephalosporins und von ihren salzen
DE1795484C3 (de)	1976-04-15	Verfahren zur Herstellung von Derivaten des Cephalosporin C
DE1695071C3 (de)	1977-02-10	3-Hydroxy-2-imino-1 (2H) -pyridinsulfonsäure-monohydrat
DE953432C (de)	1956-11-29	Verfahren zur Reinigung von chlortetracyclinhaltigen Stoffen
AT368165B (de)	1982-09-27	Verfahren zur herstellung von neuen magnesiumverbindungen
DE1176147B (de)	1964-08-20	Verfahren zur Herstellung von 7-Aminocephalosporansaeure