CS235320B2 - Method of sultamiciline's addition salt preparation - Google Patents
Method of sultamiciline's addition salt preparation Download PDFInfo
- Publication number
- CS235320B2 CS235320B2 CS832817A CS281783A CS235320B2 CS 235320 B2 CS235320 B2 CS 235320B2 CS 832817 A CS832817 A CS 832817A CS 281783 A CS281783 A CS 281783A CS 235320 B2 CS235320 B2 CS 235320B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- compound
- salt
- salts
- aqueous
- Prior art date
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- 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
Landscapes
- 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)
- 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 (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 (no) |
| EP (1) | EP0092968B1 (no) |
| JP (1) | JPS58201792A (no) |
| KR (1) | KR860001279B1 (no) |
| AU (1) | AU536854B2 (no) |
| CA (1) | CA1187484A (no) |
| CS (1) | CS235320B2 (no) |
| DD (1) | DD209632A5 (no) |
| DE (1) | DE3362502D1 (no) |
| DK (1) | DK162168C (no) |
| EG (1) | EG16412A (no) |
| ES (1) | ES521728A0 (no) |
| FI (1) | FI76092C (no) |
| GR (1) | GR78582B (no) |
| HK (1) | HK20588A (no) |
| HU (1) | HU187068B (no) |
| IE (1) | IE54628B1 (no) |
| IL (1) | IL68453A (no) |
| NO (1) | NO156202C (no) |
| NZ (1) | NZ203988A (no) |
| PH (1) | PH18035A (no) |
| PL (1) | PL134978B1 (no) |
| PT (1) | PT76587B (no) |
| SG (1) | SG104087G (no) |
| SU (1) | SU1138030A3 (no) |
| YU (1) | YU43170B (no) |
| ZA (1) | ZA832845B (no) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5336762A (en) * | 1985-11-18 | 1994-08-09 | Access Pharmaceuticals, Inc. | Polychelating agents for image and spectral enhancement (and spectral shift) |
| EP0247156B1 (en) * | 1985-11-18 | 1993-06-23 | 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 |
| ATE223916T1 (de) * | 1994-05-02 | 2002-09-15 | Shionogi & Co | Kristalline pyrrolidylthiocarbapenem derivate, lyophilisierste präparationen dieser kristalle und verfahren zu deren herstellung |
| 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 |
| CA2496623C (en) | 2002-08-29 | 2008-02-12 | Taisho Pharmaceutical Co., Ltd. | Benzenesulfonate salts of 4-fluoro-2-cyanopyrrolidine derivatives |
| PT1606293E (pt) * | 2003-03-27 | 2009-10-14 | Basilea Pharmaceutica Ag | Cefalosporina sob forma cristalina |
| JP2007509975A (ja) * | 2003-10-31 | 2007-04-19 | アルザ・コーポレーシヨン | ギャバペンチン及びプレギャバリンの増加された吸収のための組成物及び投与形態物 |
| 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 |
| BRPI0815591B8 (pt) | 2007-08-22 | 2021-05-25 | Astrazeneca Ab | composto, composição farmacêutica, e, uso de um composto. |
| EP2220050A2 (en) | 2007-10-26 | 2010-08-25 | The Regents Of The University Of California | Diarylhydantoin compounds as androgen receptor modulators |
| PE20120003A1 (es) * | 2009-01-30 | 2012-02-12 | Glaxosmithkline Llc | Hidrocloruro de n-{(1s)-2-amino-1-[(3-fluorofenil)metil)etil}-5-cloro-4-(4-cloro-1-metil-1h-pirazol-5-il)-2-tiofenocarboxamida cristalino |
| 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 |
| WO2011102793A1 (en) * | 2010-02-18 | 2011-08-25 | Astrazeneca Ab | Solid forms comprising a cyclopropyl amide derivative |
| AU2011218492B2 (en) * | 2010-02-18 | 2014-11-13 | Astrazeneca Ab | New crystalline form of a cyclopropyl benzamide derivative |
| JP6310396B2 (ja) * | 2012-12-03 | 2018-04-11 | 株式会社カネカ | 還元型補酵素ｑ１０誘導体およびその製造方法 |
| KR102460388B1 (ko) * | 2013-09-05 | 2022-10-27 | 미쓰비시 타나베 파마 코퍼레이션 | 신규한 결정성 아릴알킬아민 화합물 및 그의 제조 방법 |
| HRP20201343T1 (hr) * | 2014-10-21 | 2020-11-27 | Ariad Pharmaceuticals, Inc. | Kristalni oblici 5-kloro-n4-[-2-(dimetilfosforil)fenil]-n2-{2-metoksi-4-[4-(4-metilpiperazin-1-il)piperidin-1-il]pirimidin-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 |
| CA3011323A1 (en) * | 2016-01-22 | 2017-07-27 | Sandoz Ag | Crystalline eravacycline bis-hydrochloride |
| AU2017292818B2 (en) | 2016-07-07 | 2021-10-21 | Cyclerion Therapeutics, Inc. | Solid forms of an sGC stimulator |
| 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 |
| USD994821S1 (en) | 2019-02-13 | 2023-08-08 | Hs Produkt D.O.O. | Pistol |
| USD1077123S1 (en) | 2019-02-13 | 2025-05-27 | Hs Produkt D.O.O. | Firearm sight |
| USD1071069S1 (en) | 2019-02-13 | 2025-04-15 | Hs Produkt D.O.O. | Stippled textured body for a firearm or the like |
| USD998740S1 (en) | 2019-02-13 | 2023-09-12 | Hs Produkt D.O.O. | Firearm |
| USD1057880S1 (en) | 2019-08-09 | 2025-01-14 | Hs Produkt D.O.O. | Pistol |
| JP2024506382A (ja) * | 2021-02-15 | 2024-02-13 | プロペラ セラピューティクス インコーポレイテッド | アビラテロンプロドラッグ |
| USD1049292S1 (en) * | 2021-04-06 | 2024-10-29 | Springfield, Inc. | Pistol |
| 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 |
| WO2023125700A1 (zh) * | 2021-12-28 | 2023-07-06 | 南京明德新药研发有限公司 | 四氢环庚吲唑化合物的盐型、晶型 |
| 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 |
| ZAA202301172S (en) | 2023-04-28 | 2024-06-26 | Hs Produkt D O O | Firearm |
| WO2025019497A2 (en) * | 2023-07-17 | 2025-01-23 | 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 |
| IE49881B1 (en) * | 1979-02-13 | 1986-01-08 | Leo Pharm Prod Ltd | B-lactam intermediates |
| 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 |
| GB2084572B (en) * | 1980-10-06 | 1984-07-11 | Leo Pharm Prod Ltd | 1,1-dioxopenicillanoyloxymethyl 6-(d-aphenylacetamido)penicillanate napsylate |
| IE51516B1 (en) * | 1980-10-06 | 1987-01-07 | Leo Pharm Prod Ltd | 1,1-dioxapenicillanoyloxymethyl 6-(d-alpha-amino-alpha-phenylacetamido)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 SU SU833578255A patent/SU1138030A3/ru active
- 1983-04-19 PL PL1983241553A patent/PL134978B1/pl unknown
- 1983-04-20 DE DE8383302238T patent/DE3362502D1/de not_active Expired
- 1983-04-20 EP EP83302238A patent/EP0092968B1/en not_active Expired
- 1983-04-20 CS CS832817A patent/CS235320B2/cs unknown
- 1983-04-20 EG EG249/83A patent/EG16412A/xx active
- 1983-04-21 CA CA000426451A patent/CA1187484A/en not_active Expired
- 1983-04-21 PH PH28804A patent/PH18035A/en unknown
- 1983-04-21 IL IL68453A patent/IL68453A/xx not_active IP Right Cessation
- 1983-04-21 YU YU904/83A patent/YU43170B/xx unknown
- 1983-04-21 GR GR71155A patent/GR78582B/el unknown
- 1983-04-21 DD DD83250080A patent/DD209632A5/de not_active IP Right Cessation
- 1983-04-21 ES ES521728A patent/ES521728A0/es active Granted
- 1983-04-22 FI FI831392A patent/FI76092C/fi not_active IP Right Cessation
- 1983-04-22 AU AU13871/83A patent/AU536854B2/en not_active Expired
- 1983-04-22 PT PT76587A patent/PT76587B/pt unknown
- 1983-04-22 KR KR1019830001708A patent/KR860001279B1/ko not_active Expired
- 1983-04-22 IE IE926/83A patent/IE54628B1/en not_active IP Right Cessation
- 1983-04-22 HU HU831409A patent/HU187068B/hu 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
- 1983-04-22 JP JP58071315A patent/JPS58201792A/ja active Granted
-
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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