CS235320B2 - Method of sultamiciline's addition salt preparation - Google Patents

Method of sultamiciline's addition salt preparation Download PDF

Info

Publication number: CS235320B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; compound; salt; salts; aqueous
Prior art date: 1982-04-23

Application number

CS832817A

Other languages

Czech (cs)

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

1983-04-20

Publication date

1985-05-15

1983-04-20 Application filed by Pfizer filed Critical Pfizer

1985-05-15 Publication of CS235320B2 publication Critical patent/CS235320B2/cs

Links

150000003839 salts Chemical class 0.000 title claims abstract description 39
238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 8
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims abstract description 8
229940092714 benzenesulfonic acid Drugs 0.000 claims abstract description 8
-1 dihydrate salts Chemical class 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 4
125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
229940077388 benzenesulfonate Drugs 0.000 claims description 5
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 3
239000003513 alkali Substances 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
101150108015 STR6 gene Proteins 0.000 claims 1
239000003125 aqueous solvent Substances 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
OPYGFNJSCUDTBT-PMLPCWDUSA-N sultamicillin Chemical class 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 abstract description 14
229960001326 sultamicillin Drugs 0.000 abstract description 12
239000003814 drug Substances 0.000 abstract description 10
239000002552 dosage form Substances 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000000203 mixture Substances 0.000 description 16
239000000243 solution Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
229960000723 ampicillin Drugs 0.000 description 9
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 9
150000004683 dihydrates Chemical class 0.000 description 7
239000000047 product Substances 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
239000007900 aqueous suspension Substances 0.000 description 5
QWICHYWTBZTTRD-UHFFFAOYSA-N benzenesulfonic acid;dihydrate Chemical compound O.O.OS(=O)(=O)C1=CC=CC=C1 QWICHYWTBZTTRD-UHFFFAOYSA-N 0.000 description 5
239000003085 diluting agent Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000012458 free base Substances 0.000 description 4
150000004677 hydrates Chemical class 0.000 description 4
239000012071 phase Substances 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
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 4
239000003826 tablet Substances 0.000 description 4
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 3
RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 description 3
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 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000008272 agar Substances 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
239000007787 solid Substances 0.000 description 3
229960005256 sulbactam Drugs 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
108090000204 Dipeptidase 1 Proteins 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
241000191938 Micrococcus luteus Species 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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
102000006635 beta-lactamase Human genes 0.000 description 2
238000004166 bioassay Methods 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 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
238000001035 drying Methods 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
239000003112 inhibitor Substances 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
229940111202 pepsin Drugs 0.000 description 2
239000002243 precursor Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
239000000376 reactant Substances 0.000 description 2
229940077386 sodium benzenesulfonate Drugs 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
159000000000 sodium salts Chemical class 0.000 description 2
MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 2
238000005160 1H NMR spectroscopy Methods 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
208000035143 Bacterial infection Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
241001465754 Metazoa Species 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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-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
238000002679 ablation Methods 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001342 alkaline earth metals Chemical class 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
150000001413 amino acids Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
150000008107 benzenesulfonic acids Chemical class 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000005352 clarification Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002081 enamines Chemical group 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940079360 enema for constipation Drugs 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
238000001914 filtration Methods 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
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229920001903 high density polyethylene Polymers 0.000 description 1
239000004700 high-density polyethylene Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
239000013067 intermediate product 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
239000011777 magnesium 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
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 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
238000001556 precipitation Methods 0.000 description 1
NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical compound CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 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
238000013112 stability test 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
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000004094 surface-active agent 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
230000002195 synergetic effect Effects 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
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
235000013522 vodka 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
- 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)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (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)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS832817A 1982-04-23 1983-04-20 Method of sultamiciline's addition salt preparation CS235320B2 (en)

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
CS235320B2 true CS235320B2 (en)	1985-05-15

Family

ID=23462725

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS832817A CS235320B2 (en)	1982-04-23	1983-04-20	Method of sultamiciline's addition salt preparation

Country Status (27)

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

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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 CS CS832817A patent/CS235320B2/cs unknown
- 1983-04-20 EG EG249/83A patent/EG16412A/xx active
- 1983-04-20 DE DE8383302238T patent/DE3362502D1/de not_active Expired
- 1983-04-20 EP EP83302238A patent/EP0092968B1/en not_active Expired
- 1983-04-21 ES ES521728A patent/ES521728A0/es active Granted
- 1983-04-21 CA CA000426451A patent/CA1187484A/en not_active Expired
- 1983-04-21 YU YU904/83A patent/YU43170B/xx unknown
- 1983-04-21 GR GR71155A patent/GR78582B/el unknown
- 1983-04-21 IL IL68453A patent/IL68453A/xx not_active IP Right Cessation
- 1983-04-21 PH PH28804A patent/PH18035A/en unknown
- 1983-04-21 DD DD83250080A patent/DD209632A5/de not_active IP Right Cessation
- 1983-04-22 AU AU13871/83A patent/AU536854B2/en not_active Expired
- 1983-04-22 KR KR1019830001708A patent/KR860001279B1/ko not_active Expired
- 1983-04-22 JP JP58071315A patent/JPS58201792A/ja active Granted
- 1983-04-22 IE IE926/83A patent/IE54628B1/en not_active IP Right Cessation
- 1983-04-22 FI FI831392A patent/FI76092C/fi not_active IP Right Cessation
- 1983-04-22 NZ NZ203988A patent/NZ203988A/en unknown
- 1983-04-22 PT PT76587A patent/PT76587B/pt unknown
- 1983-04-22 ZA ZA832845A patent/ZA832845B/xx unknown
- 1983-04-22 NO NO831430A patent/NO156202C/no not_active IP Right Cessation
- 1983-04-22 HU HU831409A patent/HU187068B/hu unknown
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
ZA832845B (en)	1984-11-28
EP0092968B1 (en)	1986-03-12
NO831430L (no)	1983-10-24
NZ203988A (en)	1986-01-24
FI831392L (fi)	1983-10-24
AU1387183A (en)	1983-11-17
PH18035A (en)	1985-03-06
PT76587B (en)	1986-02-27
DD209632A5 (de)	1984-05-16
DK162168B (da)	1991-09-23
KR860001279B1 (ko)	1986-09-05
DK162168C (da)	1992-03-02
FI831392A0 (fi)	1983-04-22
EP0092968A1 (en)	1983-11-02
DK101783D0 (da)	1983-02-28
YU43170B (en)	1989-04-30
SG104087G (en)	1988-07-15
EG16412A (en)	1989-03-30
IL68453A (en)	1986-08-31
HU187068B (en)	1985-11-28
IL68453A0 (en)	1983-07-31
ES8406075A1 (es)	1984-07-01
PL241553A1 (en)	1983-11-21
US4432987A (en)	1984-02-21
DK101783A (da)	1983-10-24
PT76587A (en)	1983-05-01
JPS58201792A (ja)	1983-11-24
CA1187484A (en)	1985-05-21
GR78582B (mo)	1984-09-27
HK20588A (en)	1988-03-25
FI76092C (fi)	1988-09-09
NO156202C (no)	1987-08-19
SU1138030A3 (ru)	1985-01-30
JPH0119395B2 (mo)	1989-04-11
YU90483A (en)	1986-04-30
FI76092B (fi)	1988-05-31
KR840004437A (ko)	1984-10-15
PL134978B1 (en)	1985-09-30
IE54628B1 (en)	1989-12-20
AU536854B2 (en)	1984-05-24
NO156202B (no)	1987-05-04
ES521728A0 (es)	1984-07-01
IE830926L (en)	1983-10-23
DE3362502D1 (en)	1986-04-17

Publication	Publication Date	Title
CS235320B2 (en)	1985-05-15	Method of sultamiciline's addition salt preparation
CA1180696A (en)	1985-01-08	Method for producing chemical compounds
JPH0314811B2 (mo)	1991-02-27
NZ192762A (en)	1984-10-19	Penicillin derivatives and pharmaceutical and veterinary compositions
CS235502B2 (en)	1985-05-15	Method of 1-ethyl or vinyl-6-halogen-1-4-dihydro-4-oxo-7- (1-piperazinyl)-1,8-naphtyridin-3-carboxyl acid production
KR830001903B1 (ko)	1983-09-19	페니실란산유도체의 제조방법
FI68237B (fi)	1985-04-30	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 3-(4-hydroxi-5-pyrimidyl)ureido-bensylpenicilliner
KR19990014669A (ko)	1999-02-25	항균성 세팔로스포린
KR0178956B1 (ko)	1999-03-20	항균성 페넴 에스테르 유도체
EP0314363A2 (en)	1989-05-03	Anti-anxiety agents
JPS60126284A (ja)	1985-07-05	ピリドンカルボン酸誘導体およびその塩
KR0178957B1 (ko)	1999-03-20	페넴 화합물
JPH0516437B2 (mo)	1993-03-04
SU1015830A3 (ru)	1983-04-30	Способ получени сложных эфиров 6-амидинопенициллановых кислот или их аддитивных солей с кислотами и его вариант
JPH05508170A (ja)	1993-11-18	新規なジフルオロキノロンと、その合成方法と、それを含む医薬
KR840002214B1 (ko)	1984-12-03	2β-클로로메틸-2α-메틸페남-3α-카르복실산 술폰, 염 또는 그의 에스테르의 제조방법
KR850001066B1 (ko)	1985-07-25	2β-클로로메틸-2α-메틸페남-3α-카르복실산술폰, 2염 또는 그의 에스테르의 제조방법
EP0105912B1 (en)	1986-06-11	Improved melaminylthioarsenites
US4477449A (en)	1984-10-16	Certain 1,8-naphthyridine compounds useful as antibacterial agents
US5021597A (en)	1991-06-04	Novel acrylic acid salts, a process for their preparation, pharmaceutical compositions containing them and their use in the medicine
IE47929B1 (en)	1984-07-25	Substituted imidazolidinyl-3-chloro-3-cephem-4-carboxylic acids
CA2328965A1 (en)	1999-11-18	Novel cephalosporin compounds, processes for preparation thereof and antimicrobial compositions containing the same
KR830001902B1 (ko)	1983-09-19	폐니실란산유도체의 제조방법
JPH05117280A (ja)	1993-05-14	アミノ酸置換チアゼトキノリン−３−カルボン酸誘導体
JP3274856B2 (ja)	2002-04-15	ペネム化合物