CA1187484A - Crystalline benzenesulfonate salts of sultamicillin - Google Patents
Crystalline benzenesulfonate salts of sultamicillinInfo
- Publication number
- CA1187484A CA1187484A CA000426451A CA426451A CA1187484A CA 1187484 A CA1187484 A CA 1187484A CA 000426451 A CA000426451 A CA 000426451A CA 426451 A CA426451 A CA 426451A CA 1187484 A CA1187484 A CA 1187484A
- Authority
- CA
- Canada
- Prior art keywords
- sultamicillin
- formula
- benzenesulfonic acid
- acid addition
- salt
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 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 title claims abstract description 25
- 229960001326 sultamicillin Drugs 0.000 title claims abstract description 24
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 19
- 229940092714 benzenesulfonic acid Drugs 0.000 claims abstract description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 6
- QWICHYWTBZTTRD-UHFFFAOYSA-N benzenesulfonic acid;dihydrate Chemical compound O.O.OS(=O)(=O)C1=CC=CC=C1 QWICHYWTBZTTRD-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 1
- -1 dihydrate salts Chemical class 0.000 abstract description 14
- 239000003814 drug Substances 0.000 abstract description 8
- 239000002552 dosage form Substances 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 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 11
- 229960000723 ampicillin Drugs 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000004683 dihydrates Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 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 7
- 229960005256 sulbactam Drugs 0.000 description 7
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 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 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 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 3
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-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
- 108090000204 Dipeptidase 1 Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 229940077388 benzenesulfonate Drugs 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
- 102000006635 beta-lactamase Human genes 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 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
- RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 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
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 239000003781 beta lactamase inhibitor Substances 0.000 description 2
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 2
- 238000004166 bioassay Methods 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
- 239000000796 flavoring agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 150000002500 ions Chemical class 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 210000002966 serum Anatomy 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
- 238000003860 storage Methods 0.000 description 2
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
- 101150041968 CDC13 gene Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000191938 Micrococcus luteus Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 102000057297 Pepsin A Human genes 0.000 description 1
- 108090000284 Pepsin A Proteins 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
- 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
- 238000013019 agitation Methods 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
- 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
- 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
- 238000001514 detection method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007884 disintegrant Substances 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 class 0.000 description 1
- 230000002708 enhancing effect Effects 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
- 239000000706 filtrate Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- 238000002329 infrared spectrum Methods 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
- 239000007788 liquid Substances 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
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000005649 metathesis reaction Methods 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
- 210000000056 organ Anatomy 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229940111202 pepsin Drugs 0.000 description 1
- 239000012071 phase Substances 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
- 238000001556 precipitation Methods 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-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
- 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
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US371,156 | 1982-04-23 | ||
| US06/371,156 US4432987A (en) | 1982-04-23 | 1982-04-23 | Crystalline benzenesulfonate salts of sultamicillin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1187484A true CA1187484A (en) | 1985-05-21 |
Family
ID=23462725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000426451A Expired CA1187484A (en) | 1982-04-23 | 1983-04-21 | Crystalline benzenesulfonate salts of sultamicillin |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4432987A (enExample) |
| EP (1) | EP0092968B1 (enExample) |
| JP (1) | JPS58201792A (enExample) |
| KR (1) | KR860001279B1 (enExample) |
| AU (1) | AU536854B2 (enExample) |
| CA (1) | CA1187484A (enExample) |
| CS (1) | CS235320B2 (enExample) |
| DD (1) | DD209632A5 (enExample) |
| DE (1) | DE3362502D1 (enExample) |
| DK (1) | DK162168C (enExample) |
| EG (1) | EG16412A (enExample) |
| ES (1) | ES521728A0 (enExample) |
| FI (1) | FI76092C (enExample) |
| GR (1) | GR78582B (enExample) |
| HK (1) | HK20588A (enExample) |
| HU (1) | HU187068B (enExample) |
| IE (1) | IE54628B1 (enExample) |
| IL (1) | IL68453A (enExample) |
| NO (1) | NO156202C (enExample) |
| NZ (1) | NZ203988A (enExample) |
| PH (1) | PH18035A (enExample) |
| PL (1) | PL134978B1 (enExample) |
| PT (1) | PT76587B (enExample) |
| SG (1) | SG104087G (enExample) |
| SU (1) | SU1138030A3 (enExample) |
| YU (1) | YU43170B (enExample) |
| ZA (1) | ZA832845B (enExample) |
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|---|---|---|---|---|
| EP0247156B1 (en) * | 1985-11-18 | 1993-06-23 | Access Pharmaceuticals Inc. | Polychelating agents for image and spectral enhancement (and spectral shift) |
| US5336762A (en) * | 1985-11-18 | 1994-08-09 | Access Pharmaceuticals, Inc. | Polychelating agents for image and spectral enhancement (and spectral shift) |
| KR910009271B1 (ko) * | 1989-06-20 | 1991-11-08 | 김영설 | 1,1-디옥소페닐실라노일 옥시메틸 D-6-[α-(메틸렌아미노)페닐-아세트아미도]-페니실라네이트와 그의 파라-톨루엔술폰산염 |
| CN1048248C (zh) * | 1994-05-02 | 2000-01-12 | 盐野义制药株式会社 | 吡咯烷基硫基碳代青霉烯衍生物的结晶、含该结晶的冷冻干燥制剂及其制造方法 |
| JP3382159B2 (ja) * | 1998-08-05 | 2003-03-04 | 株式会社東芝 | 情報記録媒体とその再生方法及び記録方法 |
| PL374664A1 (en) | 2002-08-29 | 2005-10-31 | Taisho Pharmaceutical Co, Ltd. | Benzenesulfonate of 4-fluoro-2-cyanopyrrolidine derivative |
| JP5230934B2 (ja) * | 2003-03-27 | 2013-07-10 | バジリア ファルマスーチカ アーゲー | 結晶形態のセファロスポリン |
| CA2543945A1 (en) * | 2003-10-31 | 2005-05-12 | Alza Corporation | Compositions and dosage forms for enhanced absorption of 3-amino-n-butyl-phosphinic acid |
| FR2877696B1 (fr) | 2004-11-09 | 2009-09-18 | Renault Sas | Dispositif et procede d'estimation en temps reel de l'angle de debut de combustion d'un moteur a combustion interne |
| WO2009024823A2 (en) | 2007-08-22 | 2009-02-26 | Astrazeneca Ab | Oxadiazole derivatives as dgat inhibitors |
| AR069039A1 (es) | 2007-10-26 | 2009-12-23 | Univ California | Compuestos de diarilhidantoina, composicion farmaceutica, proceso de obtencion del compuesto, utiles para desordenes hiperproliferativos |
| CN102405047B (zh) * | 2009-01-30 | 2014-07-09 | 葛兰素史密斯克莱有限责任公司 | 结晶型的n-{(1s)-2-氨基-1-[(3-氟苯基)甲基]乙基}-5-氯-4-(4-氯-1-甲基-1h-吡唑-5-基)-2-噻吩甲酰胺盐酸盐 |
| TW201039825A (en) | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| WO2011006061A1 (en) * | 2009-07-10 | 2011-01-13 | Evolva Sa | Diyne compositions |
| MX2012009473A (es) * | 2010-02-18 | 2012-09-12 | Astrazeneca Ab | Procesos para preparar derivados de ciclopropilamidas e intermedios asociados con estas. |
| MX2012009537A (es) * | 2010-02-18 | 2012-08-31 | Astrazeneca Ab | Formas solidas que comprenden un derivado de ciclopropilamida. |
| CN104903289B (zh) * | 2012-12-03 | 2017-06-09 | 株式会社钟化 | 还元型辅酶q10衍生物及其制造方法 |
| US9643920B2 (en) * | 2013-09-05 | 2017-05-09 | Mitsubishi Tanabe Pharma Corporation | Crystalline 4-(3S-(1R-(1-napthyl)ethylamino)pyrrolidin-1-yl)phenylacetic acid |
| PT3209647T (pt) | 2014-10-21 | 2020-09-10 | Ariad Pharma Inc | Formas cristalinas de 5-cloro-n4-[2-(dimetilfosforil)fenil]-n2-{2-metoxi-4-[4-(4-metilpiperazin-1-il)piperidin-1-il]pirimidino-2,4-diamina |
| CN104958318A (zh) * | 2015-08-04 | 2015-10-07 | 青岛蓝盛洋医药生物科技有限责任公司 | 一种治疗感染性疾病的药物舒巴坦钠组合物 |
| EP3778567A1 (en) * | 2016-01-22 | 2021-02-17 | Sandoz Ag | Crystalline eravacycline bis-hydrochloride |
| EA039753B1 (ru) * | 2016-07-07 | 2022-03-10 | Сайклерион Терапьютикс, Инк. | ТВЕРДЫЕ ФОРМЫ СТИМУЛЯТОРА sGC |
| WO2019089540A1 (en) * | 2017-10-30 | 2019-05-09 | Theracaine Llc | Hydrophobic arenesulfonate salts |
| US11186556B1 (en) * | 2018-10-16 | 2021-11-30 | Celgene Corporation | Salts of a thiazolidinone compound, solid forms, compositions and methods of use thereof |
| UA119735C2 (uk) | 2018-12-20 | 2019-07-25 | Анатолій Семенович Редер | Фармацевтична сполука, спосіб її отримання та застосування як лікарського засобу |
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| USD998740S1 (en) | 2019-02-13 | 2023-09-12 | Hs Produkt D.O.O. | Firearm |
| USD994822S1 (en) | 2019-02-13 | 2023-08-08 | Hs Produkt D.O.O. | Pistol |
| USD1071069S1 (en) | 2019-02-13 | 2025-04-15 | Hs Produkt D.O.O. | Stippled textured body for a firearm or the like |
| USD1057880S1 (en) | 2019-08-09 | 2025-01-14 | Hs Produkt D.O.O. | Pistol |
| CA3207282A1 (en) * | 2021-02-15 | 2022-08-18 | Matthew J. Sharp | Abiraterone prodrugs |
| USD1049292S1 (en) * | 2021-04-06 | 2024-10-29 | Springfield, Inc. | Pistol |
| WO2022237808A1 (zh) * | 2021-05-12 | 2022-11-17 | 浙江龙传生物医药科技有限公司 | 吡咯并嘧啶类化合物的晶型及其制备方法 |
| BR112023021606A2 (pt) * | 2021-05-14 | 2023-12-19 | Global Blood Therapeutics Inc | Formas sólidas de modulador de hemoglobina |
| USD1069964S1 (en) | 2021-11-03 | 2025-04-08 | Hs Produkt D.O.O. | Pistol slide |
| US12410155B2 (en) * | 2021-12-28 | 2025-09-09 | Zhejiang Yangli Pharmaceutical Technology Co., Ltd. | Salt form and crystal form of tetrahydrocyclohepta indazole compound |
| CA3253725A1 (en) * | 2022-05-20 | 2023-11-23 | Caamtech, Inc. | TRYPTAMINE DERIVATIVES |
| USD1072997S1 (en) | 2022-08-29 | 2025-04-29 | Springfield, Inc. | Firearm |
| USD1057882S1 (en) | 2022-08-29 | 2025-01-14 | Springfield, Inc. | Combined serrations for a firearm slide |
| USD1061781S1 (en) | 2022-11-30 | 2025-02-11 | Hs Produkt D.O.O. | Pistol |
| ZAA202301170S (en) | 2023-04-28 | 2024-06-26 | Hs Produkt D O O | Firearm |
| WO2025016385A1 (en) * | 2023-07-17 | 2025-01-23 | Kura Oncology, Inc. | Pharmaceutical compositions comprising a menin inhibitor |
| AU2024292586A1 (en) * | 2023-07-17 | 2026-01-29 | Kura Oncology, Inc. | Crystalline forms of a menin inhibitor |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4234579A (en) * | 1977-06-07 | 1980-11-18 | Pfizer Inc. | Penicillanic acid 1,1-dioxides as β-lactamase inhibitors |
| IE49880B1 (en) * | 1979-02-13 | 1986-01-08 | Leo Pharm Prod Ltd | Penicillin derivatives |
| ZA80796B (en) * | 1979-02-13 | 1981-02-25 | Leo Pharm Prod Ltd | Chemical compounds |
| US4244951A (en) * | 1979-05-16 | 1981-01-13 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
| IE51516B1 (en) * | 1980-10-06 | 1987-01-07 | Leo Pharm Prod Ltd | 1,1-dioxapenicillanoyloxymethyl 6-(d-alpha-amino-alpha-phenylacetamido)penicillanate napsylate |
| GB2084572B (en) * | 1980-10-06 | 1984-07-11 | Leo Pharm Prod Ltd | 1,1-dioxopenicillanoyloxymethyl 6-(d-aphenylacetamido)penicillanate napsylate |
| IL64009A (en) * | 1980-10-31 | 1984-09-30 | Rech Applications Therap | Crystalline 1,1-dioxopenicillanoyloxymethyl 6-(d-alpha-amino-alpha-phenylacetamido)penicillanate tosylate hydrates,their production and pharmaceutical compositions containing them |
-
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 DE DE8383302238T patent/DE3362502D1/de not_active Expired
- 1983-04-20 EG EG249/83A patent/EG16412A/xx active
- 1983-04-20 EP EP83302238A patent/EP0092968B1/en not_active Expired
- 1983-04-21 IL IL68453A patent/IL68453A/xx not_active IP Right Cessation
- 1983-04-21 ES ES521728A patent/ES521728A0/es active Granted
- 1983-04-21 GR GR71155A patent/GR78582B/el unknown
- 1983-04-21 PH PH28804A patent/PH18035A/en unknown
- 1983-04-21 DD DD83250080A patent/DD209632A5/de not_active IP Right Cessation
- 1983-04-21 CA CA000426451A patent/CA1187484A/en not_active Expired
- 1983-04-21 YU YU904/83A patent/YU43170B/xx unknown
- 1983-04-22 AU AU13871/83A patent/AU536854B2/en not_active Expired
- 1983-04-22 JP JP58071315A patent/JPS58201792A/ja active Granted
- 1983-04-22 KR KR1019830001708A patent/KR860001279B1/ko not_active Expired
- 1983-04-22 HU HU831409A patent/HU187068B/hu unknown
- 1983-04-22 FI FI831392A patent/FI76092C/fi not_active IP Right Cessation
- 1983-04-22 IE IE926/83A patent/IE54628B1/en not_active IP Right Cessation
- 1983-04-22 PT PT76587A patent/PT76587B/pt unknown
- 1983-04-22 NO NO831430A patent/NO156202C/no not_active IP Right Cessation
- 1983-04-22 ZA ZA832845A patent/ZA832845B/xx unknown
- 1983-04-22 NZ NZ203988A patent/NZ203988A/en 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
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| MKEX | Expiry |