DD209632A5 - Verfahren zur herstellung neuer additionssalze von sultamicillin - Google Patents

Verfahren zur herstellung neuer additionssalze von sultamicillin Download PDF

Info

Publication number: DD209632A5
Authority: DD; German Democratic Republic
Prior art keywords: sultamicillin; formula; salts; salt; crystalline
Prior art date: 1982-04-23

Application number

DD83250080A

Other languages

German (de)

English (en)

Inventor

Wayne E Barth

Vytautas J Jasys

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.)

1982-04-23

Filing date

1983-04-21

Publication date

1984-05-16

1983-04-21 Application filed by Pfizer filed Critical Pfizer

1984-05-16 Publication of DD209632A5 publication Critical patent/DD209632A5/de

Links

150000003839 salts Chemical class 0.000 title claims abstract description 37
OPYGFNJSCUDTBT-PMLPCWDUSA-N sultamicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OCOC(=O)[C@H]2C(S(=O)(=O)[C@H]3N2C(C3)=O)(C)C)(C)C)=CC=CC=C1 OPYGFNJSCUDTBT-PMLPCWDUSA-N 0.000 title claims abstract description 23
229960001326 sultamicillin Drugs 0.000 title claims abstract description 21
238000004519 manufacturing process Methods 0.000 title description 3
-1 DIHYDRATE SALTS Chemical class 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 15
239000000460 chlorine Chemical group 0.000 claims abstract description 9
229910052801 chlorine Chemical group 0.000 claims abstract description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
150000004683 dihydrates Chemical class 0.000 claims description 10
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 9
229940092714 benzenesulfonic acid Drugs 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 3
229910052783 alkali metal Inorganic materials 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 claims 1
239000002552 dosage form Substances 0.000 abstract description 5
239000003814 drug Substances 0.000 abstract description 5
239000013078 crystal Substances 0.000 abstract description 3
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
150000001875 compounds Chemical class 0.000 description 18
239000000203 mixture Substances 0.000 description 17
239000000243 solution Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound 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 description 10
229960000723 ampicillin Drugs 0.000 description 10
FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 7
229960005256 sulbactam Drugs 0.000 description 7
KMEGBUCIGMEPME-LQYKFRDPSA-N (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;(1r,4s)-3,3-dimethyl-2,2,6-trioxo-2$l^{6}-thiabicyclo[3.2.0]heptane-4-carboxylic acid Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)C2C(=O)C[C@H]21.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 KMEGBUCIGMEPME-LQYKFRDPSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000003242 anti bacterial agent Substances 0.000 description 6
239000007900 aqueous suspension Substances 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
239000000843 powder Substances 0.000 description 4
238000000634 powder X-ray diffraction Methods 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
108090000204 Dipeptidase 1 Proteins 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
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 3
241000700159 Rattus Species 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
239000002585 base Substances 0.000 description 3
229940077388 benzenesulfonate Drugs 0.000 description 3
QWICHYWTBZTTRD-UHFFFAOYSA-N benzenesulfonic acid;dihydrate Chemical compound O.O.OS(=O)(=O)C1=CC=CC=C1 QWICHYWTBZTTRD-UHFFFAOYSA-N 0.000 description 3
102000006635 beta-lactamase Human genes 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229940035423 ethyl ether Drugs 0.000 description 3
238000001914 filtration Methods 0.000 description 3
210000004051 gastric juice Anatomy 0.000 description 3
239000010410 layer Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000002002 slurry Substances 0.000 description 3
229940077386 sodium benzenesulfonate Drugs 0.000 description 3
MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
208000035143 Bacterial infection Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000191938 Micrococcus luteus Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000606860 Pasteurella Species 0.000 description 2
102000057297 Pepsin A Human genes 0.000 description 2
108090000284 Pepsin A Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000008272 agar Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
208000022362 bacterial infectious disease Diseases 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
239000003781 beta lactamase inhibitor Substances 0.000 description 2
229940126813 beta-lactamase inhibitor Drugs 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
150000004682 monohydrates Chemical class 0.000 description 2
210000002445 nipple Anatomy 0.000 description 2
229940111202 pepsin Drugs 0.000 description 2
239000012071 phase Substances 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000001509 sodium citrate Substances 0.000 description 2
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
239000000126 substance Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 2
238000005160 1H NMR spectroscopy Methods 0.000 description 1
JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 description 1
IMWJRMLLFGRBIN-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid;dihydrate Chemical compound O.O.OS(=O)(=O)C1=CC=C(Cl)C=C1 IMWJRMLLFGRBIN-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
JLBADLWTHWGGNE-CGAOXQFVSA-N [(2s,5r)-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrochloride Chemical compound Cl.C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OCOC(=O)[C@H]2C(S(=O)(=O)[C@H]3N2C(C3)=O)(C)C)(C)C)=CC=CC=C1 JLBADLWTHWGGNE-CGAOXQFVSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000007605 air drying Methods 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
229940009868 aluminum magnesium silicate Drugs 0.000 description 1
WMGSQTMJHBYJMQ-UHFFFAOYSA-N aluminum;magnesium;silicate Chemical compound [Mg+2].[Al+3].[O-][Si]([O-])([O-])[O-] WMGSQTMJHBYJMQ-UHFFFAOYSA-N 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000003255 drug test Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
150000002081 enamines Chemical group 0.000 description 1
238000010931 ester hydrolysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
CRAWBPGXIICWMH-UHFFFAOYSA-M potassium;4-chlorobenzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=C(Cl)C=C1 CRAWBPGXIICWMH-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
XLKHCFJHGIAKFX-UHFFFAOYSA-M sodium;4-chlorobenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=C(Cl)C=C1 XLKHCFJHGIAKFX-UHFFFAOYSA-M 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/28—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with modified 2-carboxyl group
- C07D499/32—Esters
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cephalosporin Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

DD83250080A 1982-04-23 1983-04-21 Verfahren zur herstellung neuer additionssalze von sultamicillin DD209632A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/371,156 US4432987A (en)	1982-04-23	1982-04-23	Crystalline benzenesulfonate salts of sultamicillin

Publications (1)

Publication Number	Publication Date
DD209632A5 true DD209632A5 (de)	1984-05-16

Family

ID=23462725

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83250080A DD209632A5 (de)	1982-04-23	1983-04-21	Verfahren zur herstellung neuer additionssalze von sultamicillin

Country Status (27)

Country	Link
US (1)	US4432987A (cs)
EP (1)	EP0092968B1 (cs)
JP (1)	JPS58201792A (cs)
KR (1)	KR860001279B1 (cs)
AU (1)	AU536854B2 (cs)
CA (1)	CA1187484A (cs)
CS (1)	CS235320B2 (cs)
DD (1)	DD209632A5 (cs)
DE (1)	DE3362502D1 (cs)
DK (1)	DK162168C (cs)
EG (1)	EG16412A (cs)
ES (1)	ES521728A0 (cs)
FI (1)	FI76092C (cs)
GR (1)	GR78582B (cs)
HK (1)	HK20588A (cs)
HU (1)	HU187068B (cs)
IE (1)	IE54628B1 (cs)
IL (1)	IL68453A (cs)
NO (1)	NO156202C (cs)
NZ (1)	NZ203988A (cs)
PH (1)	PH18035A (cs)
PL (1)	PL134978B1 (cs)
PT (1)	PT76587B (cs)
SG (1)	SG104087G (cs)
SU (1)	SU1138030A3 (cs)
YU (1)	YU43170B (cs)
ZA (1)	ZA832845B (cs)

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1982
- 1982-04-23 US US06/371,156 patent/US4432987A/en not_active Expired - Lifetime
1983
- 1983-02-28 DK DK101783A patent/DK162168C/da not_active IP Right Cessation
- 1983-04-19 PL PL1983241553A patent/PL134978B1/pl unknown
- 1983-04-19 SU SU833578255A patent/SU1138030A3/ru active
- 1983-04-20 DE DE8383302238T patent/DE3362502D1/de not_active Expired
- 1983-04-20 CS CS832817A patent/CS235320B2/cs unknown
- 1983-04-20 EG EG249/83A patent/EG16412A/xx active
- 1983-04-20 EP EP83302238A patent/EP0092968B1/en not_active Expired
- 1983-04-21 GR GR71155A patent/GR78582B/el unknown
- 1983-04-21 PH PH28804A patent/PH18035A/en unknown
- 1983-04-21 CA CA000426451A patent/CA1187484A/en not_active Expired
- 1983-04-21 ES ES521728A patent/ES521728A0/es active Granted
- 1983-04-21 DD DD83250080A patent/DD209632A5/de not_active IP Right Cessation
- 1983-04-21 IL IL68453A patent/IL68453A/xx not_active IP Right Cessation
- 1983-04-21 YU YU904/83A patent/YU43170B/xx unknown
- 1983-04-22 JP JP58071315A patent/JPS58201792A/ja active Granted
- 1983-04-22 PT PT76587A patent/PT76587B/pt unknown
- 1983-04-22 NZ NZ203988A patent/NZ203988A/en unknown
- 1983-04-22 HU HU831409A patent/HU187068B/hu unknown
- 1983-04-22 IE IE926/83A patent/IE54628B1/en not_active IP Right Cessation
- 1983-04-22 AU AU13871/83A patent/AU536854B2/en not_active Expired
- 1983-04-22 FI FI831392A patent/FI76092C/fi not_active IP Right Cessation
- 1983-04-22 ZA ZA832845A patent/ZA832845B/xx unknown
- 1983-04-22 KR KR1019830001708A patent/KR860001279B1/ko not_active Expired
- 1983-04-22 NO NO831430A patent/NO156202C/no not_active IP Right Cessation
1987
- 1987-11-25 SG SG1040/87A patent/SG104087G/en unknown
1988
- 1988-03-17 HK HK205/88A patent/HK20588A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI76092C (fi)	1988-09-09
IL68453A0 (en)	1983-07-31
ZA832845B (en)	1984-11-28
KR860001279B1 (ko)	1986-09-05
IL68453A (en)	1986-08-31
CS235320B2 (en)	1985-05-15
ES8406075A1 (es)	1984-07-01
KR840004437A (ko)	1984-10-15
IE830926L (en)	1983-10-23
FI76092B (fi)	1988-05-31
US4432987A (en)	1984-02-21
DE3362502D1 (en)	1986-04-17
YU90483A (en)	1986-04-30
CA1187484A (en)	1985-05-21
EG16412A (en)	1989-03-30
ES521728A0 (es)	1984-07-01
SG104087G (en)	1988-07-15
EP0092968A1 (en)	1983-11-02
DK162168B (da)	1991-09-23
JPS58201792A (ja)	1983-11-24
IE54628B1 (en)	1989-12-20
YU43170B (en)	1989-04-30
NO831430L (no)	1983-10-24
NZ203988A (en)	1986-01-24
HU187068B (en)	1985-11-28
JPH0119395B2 (cs)	1989-04-11
SU1138030A3 (ru)	1985-01-30
DK101783A (da)	1983-10-24
FI831392A0 (fi)	1983-04-22
PT76587A (en)	1983-05-01
FI831392L (fi)	1983-10-24
AU536854B2 (en)	1984-05-24
GR78582B (cs)	1984-09-27
DK101783D0 (da)	1983-02-28
PL241553A1 (en)	1983-11-21
NO156202C (no)	1987-08-19
HK20588A (en)	1988-03-25
DK162168C (da)	1992-03-02
PT76587B (en)	1986-02-27
EP0092968B1 (en)	1986-03-12
NO156202B (no)	1987-05-04
AU1387183A (en)	1983-11-17
PH18035A (en)	1985-03-06
PL134978B1 (en)	1985-09-30

Legal Events

Date	Code	Title	Description
1992-05-07	NAC	Public notice for inspection of provisional exclusive patent accord. to par 18/2 dd-patg.
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
SU1138030A3 (ru)	1985-01-30	Способ получени аддитивной соли бензолсульфокислоты сультамициллина
DE1942693C2 (de)	1984-03-08	Verfahren zur Herstellung von (-)-&alpha;-Amino-p-hydroxybenzylpenicillintrihydrat
DE2332878C2 (de)	1983-07-28	Salze von Cephalosporinen mit Arginin und Lysin, ihre Herstellung und injizierbare pharmazeutische Zubereitungen
DE3037102C2 (de)	1986-04-10	(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-pyridiniummethyl)-ceph-3-em-4-carboxylat-pentahydrat
DE3018590A1 (de)	1980-11-20	Bisester von methandiol mit penicillinen und penicillansaeure-1,1-dioxid
DE2448966A1 (de)	1975-04-30	Penicillinderivate
CH647527A5 (de)	1985-01-31	Salz von 1,1-dioxopenicillanoyloxymethyl-6-(d-alpha-amino-alpha-phenylacetamido)-penicillanat, verfahren zu dessen herstellung sowie dieses salz enthaltende pharmazeutische praeparate.
CH646436A5 (de)	1984-11-30	Beta-lactamverbindungen, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende pharmazeutische zubereitungen.
CH638680A5 (de)	1983-10-14	Verfahren zur herstellung einer injizierbaren waessrigen loesung eines cephalosporinantibiotikums.
DE2524321A1 (de)	1975-12-18	Antibakterielle verbindungen,verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2056983B2 (de)	1979-11-15	S-Heterocyclylthiomethyl-Cephalosporine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE3008257A1 (de)	1980-09-11	Verfahren zur herstellung von penicillansaeure-1,1-dioxid und dessen estern sowie zwischenstufen zur durchfuehrung des verfahrens
DE2706548A1 (de)	1977-08-25	Amide der pseudomonsaeure, verfahren zu ihrer herstellung und ihre verwendung
DE2311346A1 (de)	1973-10-25	Penicilline und verfahren zu deren herstellung
DE2600842C2 (cs)	1987-12-23
DE2522998A1 (de)	1975-12-11	Neues cephalosporinderivat, verfahren zu seiner herstellung und arzneimittel
DE2716172C2 (de)	1985-09-05	Bis(6-[(hexahydro-1H-azepin-1-yl)-methylenamino]-penicillanoyloxy)-methan, seine Herstellung und dieses enthaltendes Arzneimittel
CH646176A5 (de)	1984-11-15	Beta-lactam-antibiotika mit beta-lactamase-hemmwirkung.
DE2801849A1 (de)	1978-07-20	Amino-spiro eckige klammer auf oxa- (oder thia-)-cycloalkan-penam eckige klammer zu -carbonsaeuren, verfahren zu ihrer herstellung und ihre verwendung
DE2655717A1 (de)	1977-06-30	Thiadiazolylderivate von 7-acylamido-3-cephem-4-carbonsaeure, verfahren zu deren herstellung und dieselben enthaltende pharmazeutische und veterinaermedizinische mittel
DE2244915A1 (de)	1973-03-22	Antibiotika und verfahren zu deren herstellung
DE2442302C2 (de)	1982-11-18	Cephalosporine, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Mittel
EP0016374B1 (de)	1982-03-03	Neue Penicilline, ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE1938052C3 (de)	1974-11-14	Antibiotische Siomycin A-Derivate und ihre Herstellung
DE3623900A1 (de)	1987-01-29	Ceph-3-em-4-carbonsaeure-derivat