KR860001279B1 - 설타미실린의 결정형 벤젠설포네이트 염의 제조방법 - Google Patents
설타미실린의 결정형 벤젠설포네이트 염의 제조방법 Download PDFInfo
- Publication number
- KR860001279B1 KR860001279B1 KR1019830001708A KR830001708A KR860001279B1 KR 860001279 B1 KR860001279 B1 KR 860001279B1 KR 1019830001708 A KR1019830001708 A KR 1019830001708A KR 830001708 A KR830001708 A KR 830001708A KR 860001279 B1 KR860001279 B1 KR 860001279B1
- Authority
- KR
- South Korea
- Prior art keywords
- salts
- crystalline
- salt
- formula
- sulfamicillin
- 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
- 238000000034 method Methods 0.000 title claims description 12
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 title claims description 9
- 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 1
- 229960001326 sultamicillin Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 8
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QWICHYWTBZTTRD-UHFFFAOYSA-N benzenesulfonic acid;dihydrate Chemical compound O.O.OS(=O)(=O)C1=CC=CC=C1 QWICHYWTBZTTRD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 150000008043 acidic salts Chemical class 0.000 claims 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- -1 2-amino-2-phenylacet amido Chemical group 0.000 description 21
- 239000000203 mixture Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229960000723 ampicillin Drugs 0.000 description 10
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000004683 dihydrates Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000007900 aqueous suspension Substances 0.000 description 7
- 239000000047 product Substances 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
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 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 6
- 229960005256 sulbactam Drugs 0.000 description 6
- 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 5
- 239000003814 drug Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-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
- 241000894006 Bacteria Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108090000204 Dipeptidase 1 Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 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
- 239000008272 agar Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 102000006635 beta-lactamase Human genes 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RJWBTWIBUIGANW-UHFFFAOYSA-M 4-chlorobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-M 0.000 description 2
- 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 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 102000057297 Pepsin A Human genes 0.000 description 2
- 108090000284 Pepsin A Proteins 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
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000004480 active ingredient Substances 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000006194 liquid suspension 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 229940111202 pepsin Drugs 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229940077386 sodium benzenesulfonate Drugs 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
- 238000001228 spectrum Methods 0.000 description 2
- 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
- 241000283690 Bos taurus Species 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
- 208000031220 Hemophilia Diseases 0.000 description 1
- 208000009292 Hemophilia A Diseases 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical class [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction 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
- 150000002081 enamines Chemical group 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge 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
- 238000005259 measurement Methods 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- CRAWBPGXIICWMH-UHFFFAOYSA-M potassium;4-chlorobenzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=C(Cl)C=C1 CRAWBPGXIICWMH-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 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 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- SPCSAIAKCMKSJN-UHFFFAOYSA-M sodium;2-chlorobenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1Cl SPCSAIAKCMKSJN-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
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
- 235000012222 talc Nutrition 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
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 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)
- 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 |
|---|---|---|---|
| US06/371,156 US4432987A (en) | 1982-04-23 | 1982-04-23 | Crystalline benzenesulfonate salts of sultamicillin |
| US371,156 | 1982-04-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840004437A KR840004437A (ko) | 1984-10-15 |
| KR860001279B1 true KR860001279B1 (ko) | 1986-09-05 |
Family
ID=23462725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830001708A Expired KR860001279B1 (ko) | 1982-04-23 | 1983-04-22 | 설타미실린의 결정형 벤젠설포네이트 염의 제조방법 |
Country Status (27)
| Country | Link |
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| US (1) | US4432987A (https=) |
| EP (1) | EP0092968B1 (https=) |
| JP (1) | JPS58201792A (https=) |
| KR (1) | KR860001279B1 (https=) |
| AU (1) | AU536854B2 (https=) |
| CA (1) | CA1187484A (https=) |
| CS (1) | CS235320B2 (https=) |
| DD (1) | DD209632A5 (https=) |
| DE (1) | DE3362502D1 (https=) |
| DK (1) | DK162168C (https=) |
| EG (1) | EG16412A (https=) |
| ES (1) | ES8406075A1 (https=) |
| FI (1) | FI76092C (https=) |
| GR (1) | GR78582B (https=) |
| HK (1) | HK20588A (https=) |
| HU (1) | HU187068B (https=) |
| IE (1) | IE54628B1 (https=) |
| IL (1) | IL68453A (https=) |
| NO (1) | NO156202C (https=) |
| NZ (1) | NZ203988A (https=) |
| PH (1) | PH18035A (https=) |
| PL (1) | PL134978B1 (https=) |
| PT (1) | PT76587B (https=) |
| SG (1) | SG104087G (https=) |
| SU (1) | SU1138030A3 (https=) |
| YU (1) | YU43170B (https=) |
| ZA (1) | ZA832845B (https=) |
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| AU6621586A (en) * | 1985-11-18 | 1987-06-02 | University Of Texas System, The | 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 |
| WO1995029913A1 (en) * | 1994-05-02 | 1995-11-09 | Shionogi & Co., Ltd. | Crystal of pyrrolidylthiocarbapenem derivative, lyophilized preparation containing said crystal, and process for producing the same |
| 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 |
| KR100582141B1 (ko) | 2002-08-29 | 2006-05-22 | 다이쇼 세이야꾸 가부시끼가이샤 | 4-플루오로-2-시아노피롤리딘 유도체 벤젠술폰산염 |
| ES2329244T3 (es) * | 2003-03-27 | 2009-11-24 | Basilea Pharmaceutica Ag | Cefalosporina en forma cristalina. |
| KR20060108692A (ko) * | 2003-10-31 | 2006-10-18 | 알자 코포레이션 | 메트포르민의 개선된 흡수를 위한 조성물 및 제형 |
| 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 |
| DK2195293T3 (da) | 2007-08-22 | 2014-02-03 | Astrazeneca Ab | Cyclopropylamidderivater |
| EP2620432A3 (en) | 2007-10-26 | 2013-12-18 | The Regents Of the University of California | Diarylhydantoin compounds |
| 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 |
| JP2012532886A (ja) * | 2009-07-10 | 2012-12-20 | エボルバ アクチェンゲゼルシャフト | ジイン組成物 |
| BR112012020629A2 (pt) | 2010-02-18 | 2018-06-19 | Astrazeneca Ab | forma cristalina, e, método para a terapia de um distúrbio |
| US20110201622A1 (en) * | 2010-02-18 | 2011-08-18 | Collins Craig D | Solid Forms Comprising A Cyclopropyl Amide Derivative |
| WO2014087972A1 (ja) * | 2012-12-03 | 2014-06-12 | 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 |
| CN105517992B (zh) * | 2013-09-05 | 2018-06-22 | 田边三菱制药株式会社 | 新型结晶性芳烷基胺化合物及其制造方法 |
| UA119794C2 (uk) * | 2014-10-21 | 2019-08-12 | Аріад Фармасьютикалз, Інк. | Кристалічна форма 5-хлор-n4-[2-(диметилфосфорил)феніл]-n2-{2-метокси-4-[4-(4-метилпіперазин-1-іл)піперидин-1-іл]}піримідин-2,4-діаміну |
| 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 |
| CN109563087A (zh) * | 2016-07-07 | 2019-04-02 | 铁木医药有限公司 | sGC刺激剂的固体形式 |
| EP3703686A4 (en) * | 2017-10-30 | 2021-11-17 | Theracaine LLC | HYDROPHOBIC ARENE SULFONATE 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 |
| USD994822S1 (en) | 2019-02-13 | 2023-08-08 | Hs Produkt D.O.O. | Pistol |
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| USD998740S1 (en) | 2019-02-13 | 2023-09-12 | Hs Produkt D.O.O. | Firearm |
| 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 |
| US11957696B2 (en) * | 2021-02-15 | 2024-04-16 | Propella Therapeutics, Inc. | Abiraterone prodrugs |
| USD1049292S1 (en) * | 2021-04-06 | 2024-10-29 | Springfield, Inc. | Pistol |
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| CA3219786A1 (en) * | 2021-05-14 | 2022-11-17 | Global Blood Therapeutics, Inc. | Solid forms of a modulator of hemoglobin |
| US20240287066A1 (en) * | 2021-06-24 | 2024-08-29 | Sandoz Ag | Crystalline Form of Sotorasib |
| USD1069964S1 (en) | 2021-11-03 | 2025-04-08 | Hs Produkt D.O.O. | Pistol slide |
| JP7805677B2 (ja) * | 2021-12-28 | 2026-01-26 | 浙江揚歴医薬技術有限公司 | テトラヒドロシクロヘプタインダゾール化合物の結晶 |
| EP4525860A2 (en) * | 2022-05-20 | 2025-03-26 | 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 |
| ZAA202301172S (en) | 2023-04-28 | 2024-06-26 | Hs Produkt D O O | Firearm |
| IL325861A (en) * | 2023-07-17 | 2026-03-01 | Kura Oncology Inc | Crystalline forms of menin inhibitor |
| TW202517650A (zh) * | 2023-07-17 | 2025-05-01 | 美商庫拉腫瘤技術股份有限公司 | 包含ｍｅｎｉｎ抑制劑之醫藥組合物 |
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 |
| KR830001903B1 (ko) * | 1979-02-13 | 1983-09-19 | 레오 파마슈티칼 프로덕츠 리미티드 | 페니실란산유도체의 제조방법 |
| 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 EP EP83302238A patent/EP0092968B1/en not_active Expired
- 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
- 1983-04-21 GR GR71155A patent/GR78582B/el unknown
- 1983-04-21 ES ES521728A patent/ES8406075A1/es not_active Expired
- 1983-04-21 IL IL68453A patent/IL68453A/xx not_active IP Right Cessation
- 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 PH PH28804A patent/PH18035A/en unknown
- 1983-04-21 YU YU904/83A patent/YU43170B/xx unknown
- 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 KR KR1019830001708A patent/KR860001279B1/ko not_active Expired
- 1983-04-22 FI FI831392A patent/FI76092C/fi not_active IP Right Cessation
- 1983-04-22 PT PT76587A patent/PT76587B/pt unknown
- 1983-04-22 AU AU13871/83A patent/AU536854B2/en not_active Expired
- 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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