BE519217A - - Google Patents

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Publication number: BE519217A
Authority: BE; Belgium
Prior art keywords: crystals; penicillin; reaction; salt; water
Prior art date

Application number

Other languages

English (en)

French (fr)

Publication of BE519217A publication Critical patent/BE519217A/fr

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239000013078 crystal Substances 0.000 claims description 89
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 claims description 33
229930182555 Penicillin Natural products 0.000 claims description 25
229940049954 penicillin Drugs 0.000 claims description 25
238000000034 method Methods 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 19
230000008569 process Effects 0.000 claims description 17
239000003153 chemical reaction reagent Substances 0.000 claims description 16
239000000725 suspension Substances 0.000 claims description 16
-1 diamine salt Chemical class 0.000 claims description 15
239000012429 reaction media Substances 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
239000000376 reactant Substances 0.000 claims description 13
LPHDUZQZGZACHZ-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)piperidine;hydrochloride Chemical class Cl.C1CCCCN1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 LPHDUZQZGZACHZ-UHFFFAOYSA-N 0.000 claims description 12
239000007864 aqueous solution Substances 0.000 claims description 12
150000004985 diamines Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
125000005263 alkylenediamine group Chemical group 0.000 claims description 7
238000002347 injection Methods 0.000 claims description 7
239000007924 injection Substances 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
239000003381 stabilizer Substances 0.000 claims description 3
239000003755 preservative agent Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 43
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000007900 aqueous suspension Substances 0.000 description 15
238000003756 stirring Methods 0.000 description 12
238000002425 crystallisation Methods 0.000 description 10
230000008025 crystallization Effects 0.000 description 10
150000002960 penicillins Chemical class 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000012431 aqueous reaction media Substances 0.000 description 8
239000007788 liquid Substances 0.000 description 8
229920000136 polysorbate Polymers 0.000 description 8
MTRNNCLQPVCDLF-UHFFFAOYSA-N benzyl-[2-(benzylazaniumyl)ethyl]azanium;diacetate Chemical compound CC(O)=O.CC(O)=O.C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 MTRNNCLQPVCDLF-UHFFFAOYSA-N 0.000 description 7
239000011521 glass Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
FCPVYOBCFFNJFS-LQDWTQKMSA-M benzylpenicillin sodium Chemical compound [Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 FCPVYOBCFFNJFS-LQDWTQKMSA-M 0.000 description 6
239000012530 fluid Substances 0.000 description 6
241001631457 Cannula Species 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
KZDCMKVLEYCGQX-UDPGNSCCSA-N 2-(diethylamino)ethyl 4-aminobenzoate;(2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;hydrate Chemical compound O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 KZDCMKVLEYCGQX-UDPGNSCCSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
235000019371 penicillin G benzathine Nutrition 0.000 description 4
229940056360 penicillin g Drugs 0.000 description 4
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
229920000053 polysorbate 80 Polymers 0.000 description 4
230000036515 potency Effects 0.000 description 4
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
230000032683 aging Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000003556 assay Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000227 grinding Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000005695 Ammonium acetate 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
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 1
WHRVRSCEWKLAHX-LQDWTQKMSA-N benzylpenicillin procaine Chemical compound [H+].CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 WHRVRSCEWKLAHX-LQDWTQKMSA-N 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000004581 coalescence Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000036541 health Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
229940095783 procaine benzylpenicillin Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
150000003871 sulfonates Chemical class 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BE519217D BE519217A (id)

Publications (1)

Publication Number	Publication Date
BE519217A true BE519217A (id)

Family

ID=155516

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE519217D BE519217A (id)

Country Status (1)

Country	Link
BE (1)	BE519217A (id)

0
- BE BE519217D patent/BE519217A/fr unknown

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