SU1138030A3 - Способ получени аддитивной соли бензолсульфокислоты сультамициллина - Google Patents

Способ получени аддитивной соли бензолсульфокислоты сультамициллина Download PDF

Info

Publication number: SU1138030A3
Authority: SU; USSR - Soviet Union
Prior art keywords: formula; acid; compound; aqueous; salt
Prior art date: 1982-04-23

Application number

SU833578255A

Other languages

English (en)

Russian (ru)

Inventor

Эрнест Барт Вейн

Джон Джэсис Витаутас

Original Assignee

Пфайзер Инк.(Фирма)

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1982-04-23

Filing date

1983-04-19

Publication date

1985-01-30

1983-04-19 Application filed by Пфайзер Инк.(Фирма) filed Critical Пфайзер Инк.(Фирма)

1985-01-30 Application granted granted Critical

1985-01-30 Publication of SU1138030A3 publication Critical patent/SU1138030A3/ru

Links

238000000034 method Methods 0.000 title claims abstract description 13
239000000654 additive Substances 0.000 title claims abstract description 5
230000000996 additive effect Effects 0.000 title claims abstract description 5
239000002253 acid Substances 0.000 title claims description 3
150000003839 salts Chemical class 0.000 title description 18
150000001875 compounds Chemical class 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
229910052801 chlorine Chemical group 0.000 claims abstract 2
125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
239000001257 hydrogen Substances 0.000 claims abstract 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 12
229940092714 benzenesulfonic acid Drugs 0.000 claims description 12
OPYGFNJSCUDTBT-PMLPCWDUSA-N sultamicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(=O)OCOC(=O)[C@H]2C(S(=O)(=O)[C@H]3N2C(C3)=O)(C)C)(C)C)=CC=CC=C1 OPYGFNJSCUDTBT-PMLPCWDUSA-N 0.000 claims description 10
229960001326 sultamicillin Drugs 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
239000002609 medium Substances 0.000 claims description 3
159000000011 group IA salts Chemical class 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 17
-1 methylenedioxy groups Chemical group 0.000 description 15
239000000243 solution Substances 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000000725 suspension Substances 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 9
229960000723 ampicillin Drugs 0.000 description 9
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 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000003814 drug Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 5
229940079593 drug Drugs 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
229960005256 sulbactam Drugs 0.000 description 5
239000003826 tablet Substances 0.000 description 5
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 4
239000002775 capsule Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000002552 dosage form 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
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
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
108090000204 Dipeptidase 1 Proteins 0.000 description 3
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
239000008272 agar Substances 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
QWICHYWTBZTTRD-UHFFFAOYSA-N benzenesulfonic acid;dihydrate Chemical compound O.O.OS(=O)(=O)C1=CC=CC=C1 QWICHYWTBZTTRD-UHFFFAOYSA-N 0.000 description 3
102000006635 beta-lactamase Human genes 0.000 description 3
150000004683 dihydrates Chemical class 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012458 free base Substances 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
238000000634 powder X-ray diffraction Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
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
241000191938 Micrococcus luteus Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
241000606860 Pasteurella Species 0.000 description 2
229930182555 Penicillin Natural products 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
229940088710 antibiotic agent Drugs 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
230000003115 biocidal effect Effects 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
210000004051 gastric juice Anatomy 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000010410 layer 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
229940049954 penicillin Drugs 0.000 description 2
229940111202 pepsin Drugs 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
210000002966 serum Anatomy 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
238000003756 stirring Methods 0.000 description 2
229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 2
KIYRSYYOVDHSPG-UHFFFAOYSA-N 2-amino-2-phenylacetamide Chemical compound NC(=O)C(N)C1=CC=CC=C1 KIYRSYYOVDHSPG-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
OQUFOZNPBIIJTN-UHFFFAOYSA-N 2-hydroxypropane-1,2,3-tricarboxylic acid;sodium Chemical compound [Na].OC(=O)CC(O)(C(O)=O)CC(O)=O OQUFOZNPBIIJTN-UHFFFAOYSA-N 0.000 description 1
IMWJRMLLFGRBIN-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid;dihydrate Chemical compound O.O.OS(=O)(=O)C1=CC=C(Cl)C=C1 IMWJRMLLFGRBIN-UHFFFAOYSA-N 0.000 description 1
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
241000272814 Anser sp. Species 0.000 description 1
241000894006 Bacteria 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
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
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 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
230000009471 action Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000007605 air drying Methods 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002152 aqueous-organic 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
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
238000009640 blood culture Methods 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application 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
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000001804 emulsifying effect Effects 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
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
238000009472 formulation Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000004615 ingredient 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
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002483 medication Methods 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012044 organic layer Substances 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
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
238000001144 powder X-ray diffraction data Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
230000004044 response Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 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
241000894007 species Species 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
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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

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)
Cephalosporin Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

SU833578255A 1982-04-23 1983-04-19 Способ получени аддитивной соли бензолсульфокислоты сультамициллина SU1138030A3 (ru)

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
SU1138030A3 true SU1138030A3 (ru)	1985-01-30

Family

ID=23462725

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU833578255A SU1138030A3 (ru)	1982-04-23	1983-04-19	Способ получени аддитивной соли бензолсульфокислоты сультамициллина

Country Status (27)

Country	Link
US (1)	US4432987A (2)
EP (1)	EP0092968B1 (2)
JP (1)	JPS58201792A (2)
KR (1)	KR860001279B1 (2)
AU (1)	AU536854B2 (2)
CA (1)	CA1187484A (2)
CS (1)	CS235320B2 (2)
DD (1)	DD209632A5 (2)
DE (1)	DE3362502D1 (2)
DK (1)	DK162168C (2)
EG (1)	EG16412A (2)
ES (1)	ES521728A0 (2)
FI (1)	FI76092C (2)
GR (1)	GR78582B (2)
HK (1)	HK20588A (2)
HU (1)	HU187068B (2)
IE (1)	IE54628B1 (2)
IL (1)	IL68453A (2)
NO (1)	NO156202C (2)
NZ (1)	NZ203988A (2)
PH (1)	PH18035A (2)
PL (1)	PL134978B1 (2)
PT (1)	PT76587B (2)
SG (1)	SG104087G (2)
SU (1)	SU1138030A3 (2)
YU (1)	YU43170B (2)
ZA (1)	ZA832845B (2)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
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)
WO1987002893A1 (en) *	1985-11-18	1987-05-21	Board Of Regents, The University Of Texas System	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
EP0758651B1 (en) *	1994-05-02	2002-09-11	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
UA78104C2 (en)	2002-08-29	2007-02-15	Taisho Pharmaceutical Co Ltd	Benzenesulfonate salts of 4-fluoro-2-cyanopyrrolidine derivatives
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
WO2005041925A2 (en) *	2003-10-31	2005-05-12	Alza Corporation	Compositions and dosage forms for enhanced absorption
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
CN101835750B (zh)	2007-08-22	2013-07-17	阿斯利康(瑞典)有限公司	环丙基酰胺衍生物
EP2220050A2 (en)	2007-10-26	2010-08-25	The Regents Of The University Of California	Diarylhydantoin compounds as androgen receptor modulators
CA2750565C (en) *	2009-01-30	2015-10-20	Glaxosmithkline Llc	Crystalline n-{(1s)-2-amino-1-[(3-fluorophenyl)methyl]ethyl}-5-chloro-4-(4-chloro-1-methyl-1h-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride
TW201039825A (en)	2009-02-20	2010-11-16	Astrazeneca Ab	Cyclopropyl amide derivatives 983
KR20120079054A (ko) *	2009-07-10	2012-07-11	에볼바 아게	디인 조성물
JP5746718B2 (ja) *	2010-02-18	2015-07-08	アストラゼネカ・アクチエボラーグＡｓｔｒａｚｅｎｅｃａＡｋｔｉｅｂｏｌａｇ	シクロプロピルアミド誘導体からなる固体形態
US20110201623A1 (en)	2010-02-18	2011-08-18	Uczynski Michael A	Crystalline Form Of A Cyclopropyl Benzamide 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
CN108484469A (zh) *	2013-09-05	2018-09-04	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
KR102331856B1 (ko)	2014-10-21	2021-11-29	다케다 야쿠힌 고교 가부시키가이샤	결정 형태의 5-클로로-n4-[2-(디메틸포스포릴)페닐]-n2-｛2-메톡시-4-[4-(4-메틸피페라진-1-일)피페리딘-1-일]피리미딘-2,4-디아민
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
WO2017125557A1 (en) *	2016-01-22	2017-07-27	Sandoz Ag	Crystalline eravacycline bis-hydrochloride
BR112019000293A2 (pt) *	2016-07-07	2019-04-16	Ironwood Pharmaceuticals, Inc.	formas sólidas de um estimulador de sgc
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
USD998740S1 (en)	2019-02-13	2023-09-12	Hs Produkt D.O.O.	Firearm
USD994821S1 (en)	2019-02-13	2023-08-08	Hs Produkt D.O.O.	Pistol
USD1126349S1 (en)	2019-02-13	2026-05-12	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
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
EP4301749A1 (en) *	2021-03-01	2024-01-10	Orion Corporation	Solid forms of a 4h-pyran-4-one structured cyp11a1 inhibitor
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
TW202311254A (zh) *	2021-05-14	2023-03-16	美商全球血液治療公司	血紅素之調節劑之固態形式
JP2024523518A (ja) *	2021-06-24	2024-06-28	サンド・アクチエンゲゼルシヤフト	ソトラシブの結晶形態
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
WO2023225678A2 (en) *	2022-05-20	2023-11-23	Caamtech, Inc.	Tryptamine derivatives
USD1057882S1 (en)	2022-08-29	2025-01-14	Springfield, Inc.	Combined serrations for a firearm slide
USD1072997S1 (en)	2022-08-29	2025-04-29	Springfield, Inc.	Firearm
USD1061781S1 (en)	2022-11-30	2025-02-11	Hs Produkt D.O.O.	Pistol
ZAA202301173S (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)

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

Also Published As

Publication number	Publication date
FI76092C (fi)	1988-09-09
IL68453A0 (en)	1983-07-31
ZA832845B (en)	1984-11-28
KR860001279B1 (ko)	1986-09-05
IL68453A (en)	1986-08-31
CS235320B2 (en)	1985-05-15
ES8406075A1 (es)	1984-07-01
KR840004437A (ko)	1984-10-15
IE830926L (en)	1983-10-23
FI76092B (fi)	1988-05-31
US4432987A (en)	1984-02-21
DE3362502D1 (en)	1986-04-17
YU90483A (en)	1986-04-30
CA1187484A (en)	1985-05-21
EG16412A (en)	1989-03-30
ES521728A0 (es)	1984-07-01
SG104087G (en)	1988-07-15
EP0092968A1 (en)	1983-11-02
DK162168B (da)	1991-09-23
JPS58201792A (ja)	1983-11-24
IE54628B1 (en)	1989-12-20
YU43170B (en)	1989-04-30
NO831430L (no)	1983-10-24
NZ203988A (en)	1986-01-24
HU187068B (en)	1985-11-28
JPH0119395B2 (2)	1989-04-11
DK101783A (da)	1983-10-24
FI831392A0 (fi)	1983-04-22
PT76587A (en)	1983-05-01
FI831392L (fi)	1983-10-24
AU536854B2 (en)	1984-05-24
GR78582B (2)	1984-09-27
DK101783D0 (da)	1983-02-28
DD209632A5 (de)	1984-05-16
PL241553A1 (en)	1983-11-21
NO156202C (no)	1987-08-19
HK20588A (en)	1988-03-25
DK162168C (da)	1992-03-02
PT76587B (en)	1986-02-27
EP0092968B1 (en)	1986-03-12
NO156202B (no)	1987-05-04
AU1387183A (en)	1983-11-17
PH18035A (en)	1985-03-06
PL134978B1 (en)	1985-09-30

Publication	Publication Date	Title
CA1187484A (en)	1985-05-21	Crystalline benzenesulfonate salts of sultamicillin
SU1122228A3 (ru)	1984-10-30	Способ получени бис-эфиров метандиола с пенициллином и 1,1-диоксидом пенициллановой кислоты
SU1122229A3 (ru)	1984-10-30	Способ получени сложного бис-эфира метандиола с производным пенициллановой кислоты и 1,1-диоксидом пенициллановой кислоты
SU1122230A3 (ru)	1984-10-30	Способ получени производных пенициллановой кислоты или их аддитивных солей с кислотами
RU2161619C2 (ru)	2001-01-10	Кристаллические соли присоединения кислот цефема, способ их получения, содержащее их лекарственное средство
EP0787494B1 (en)	2004-06-09	Use of rifamycin derivatives for the manufacture of a medicament for the treatment of diseases caused by infections of helicobacter pylori
US3822256A (en)	1974-07-02	Crystalline monohydrates of sodium and potassium cephalexin
SU1015830A3 (ru)	1983-04-30	Способ получени сложных эфиров 6-амидинопенициллановых кислот или их аддитивных солей с кислотами и его вариант
US3997527A (en)	1976-12-14	Aminomethylarylmethylpenicillin derivatives
IE53857B1 (en)	1989-03-29	Antibacterial esters of beta-lactams, and processes and intermediates for their preparation
JPS6126548B2 (2)	1986-06-20
KR850000474B1 (ko)	1985-04-08	6β-[2-(2'-메틸페녹시카르보닐)-2-티엔-3'-일아세트아미도]페니실란산의 제조방법
US3966710A (en)	1976-06-29	Aminomethylarylmethylpenicillin derivatives
US3835115A (en)	1974-09-10	Alpha-(substituted sulfonamido)arylmethylpenicillins
US3980793A (en)	1976-09-14	Carbonate esters of penicillins and compositions and methods for treatment of bacterial infections
JP7759380B2 (ja)	2025-10-23	スルホニル尿素環置換化合物の塩形および結晶形
CA2019432A1 (en)	1990-12-20	1,1-dioxopenicil-lanoyloxymethyl d-6-[ -(methyleneamino)phenylacetamido] penicillanate and a process for the preparation thereof
US4009160A (en)	1977-02-22	Aminomethylarylmethylpenicillin derivatives
JPS5852291A (ja)	1983-03-28	ペニシリン系抗生物質誘導体とその医薬剤
KR910003957B1 (ko)	1991-06-17	세펨 유도체와 그의 제조방법
US4321196A (en)	1982-03-23	Bis-esters of methanediol with acetonides of ampicillin or amoxicillin and penicillanic acid 1,1-dioxide
KR830000330B1 (ko)	1983-03-04	피리미딜 우레이도 치환 페니실린 유도체의 제조방법
HU184992B (en)	1984-11-28	Process for producing bis-esters of methandiol
EP0053308A1 (en)	1982-06-09	Amino-penicillin derivative, the process for its preparation, and therapeutic compounds which contain it as their active principle
EP0310909A2 (de)	1989-04-12	Heteroanellierte Phenylglycin-beta-Lactam-Antibiotika, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel