CH407126A - Verfahren zur Herstellung von epimeren a-Amino-benzylpenicillinen - Google Patents

Verfahren zur Herstellung von epimeren a-Amino-benzylpenicillinen

Info

Publication number: CH407126A
Authority: CH; Switzerland
Prior art keywords: sep; acid; amino; solution; group
Prior art date: 1958-10-06

Application number

CH638961A

Other languages

German (de)

English (en)

Inventor

Peter Doyle Frank

Charles Nayler John Herbert

Smith Harry

Original Assignee

Beecham Group Ltd

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.)

1958-10-06

Filing date

1961-06-01

Publication date

1966-02-15

1958-10-06 Priority claimed from GB31847/58A external-priority patent/GB873049A/en

1960-08-25 Priority claimed from GB29345/60A external-priority patent/GB902703A/en

1961-06-01 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1966-02-15 Publication of CH407126A publication Critical patent/CH407126A/de

Links

238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 5
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 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
238000005984 hydrogenation reaction Methods 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
238000009958 sewing Methods 0.000 claims 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
239000000243 solution Substances 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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 10
239000000047 product Substances 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
239000000203 mixture Substances 0.000 description 9
229930182555 Penicillin Natural products 0.000 description 8
229940049954 penicillin Drugs 0.000 description 8
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 7
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 7
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
230000003115 biocidal effect Effects 0.000 description 5
239000007787 solid Substances 0.000 description 5
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000004816 paper chromatography Methods 0.000 description 4
238000005303 weighing Methods 0.000 description 4
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 3
241000607768 Shigella Species 0.000 description 3
241001467018 Typhis Species 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RLDJWBVOZVJJOS-UHFFFAOYSA-N 2-phenyl-2-(phenylmethoxycarbonylamino)acetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)OCC1=CC=CC=C1 RLDJWBVOZVJJOS-UHFFFAOYSA-N 0.000 description 1
-1 6 - [D () a - aminophenylacetamido] - penicillanic acid monohydrate Chemical class 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241000220317 Rosa Species 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000008272 agar Substances 0.000 description 1
125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000006340 racemization Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-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
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
- 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
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical

Landscapes

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

CH638961A 1958-10-06 1961-06-01 Verfahren zur Herstellung von epimeren a-Amino-benzylpenicillinen CH407126A (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB31847/58A GB873049A (en)	1958-10-06	1958-10-06	Improvements in or relating to penicillin derivatives
GB1630359		1959-05-12
GB29345/60A GB902703A (en)	1960-08-25	1960-08-25	Penicillins

Publications (1)

Publication Number	Publication Date
CH407126A true CH407126A (de)	1966-02-15

Family

ID=27257366

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH638961A CH407126A (de)	1958-10-06	1961-06-01	Verfahren zur Herstellung von epimeren a-Amino-benzylpenicillinen

Country Status (2)

Country	Link
CH (1)	CH407126A (fr)
FR (1)	FR12F (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR112023022742A2 (pt)	2021-05-07	2024-01-02	Baylor College Medicine	Tratamento da osteogênese imperfeita moderada a grave

1961
- 1961-06-01 CH CH638961A patent/CH407126A/de unknown
- 1961-06-05 FR FR863883A patent/FR12F/fr not_active Expired

Also Published As

Publication number	Publication date
FR12F (fr)	1962-04-20

Publication	Publication Date	Title
DE2927672C2 (fr)	1989-06-01
DE2228012B2 (de)	1979-05-23	-Aminophenylacetamido] -penicülansäure und Verfahren zu seiner Herstellung
DE1295558B (de)	1969-05-22	ª-Carboxybenzyl- und ª-Carboxythienylmethylpenicilline und Verfahren zu ihrer Herstellung
CH493528A (de)	1970-07-15	Verfahren zur Herstellung neuer substituierter Aminopyrimidine
DE1302847C2 (de)	1973-01-04	Verfahren zur herstellung von alphaaminobenzylpenicillin
DE1445506A1 (de)	1969-10-09	Verfahren zur Gewinnung von reinen alpha-Aminobenzylpenicillinen und neue antibakterielle Mittel
DE1143817C2 (de)	1973-03-29	Verfahren zur Herstellung von 6-Phenoxyacylamidopenicillansaeure-derivaten und von nicht giftigen Salzen derselben
DE3235372C2 (fr)	1990-09-06
CH407126A (de)	1966-02-15	Verfahren zur Herstellung von epimeren a-Amino-benzylpenicillinen
DE1156078C2 (de)	1973-10-25	Verfahren zur Herstellung von D(-)-ª‡-Aminobenzylpenicillin und von L(+)-ª‡-Aminobenzylpenicillin
CH616938A5 (en)	1980-04-30	Process for the preparation of 6beta-acylamino-1-oxadethiapenicillanic acids
CH449006A (de)	1967-12-31	Verfahren zur Herstellung von Fusidinsäure- und Dihydrofusidinsäurederivaten
AT375081B (de)	1984-06-25	Verfahren zur herstellung von 7-aminocephalosporansaeure und ihren estern
DE2413938C2 (fr)	1987-12-03
DE1294383B (de)	1969-05-08	Penicilline und deren Salze sowie Verfahren zu ihrer Herstellung
CH345016A (de)	1960-03-15	Verfahren zur Herstellung von p-Oxy-phenylamiden
DE1545838C3 (de)	1975-12-11	7-(2-Azidooctanamido)-cephalosporansäure, deren Salze und Verfahren zur Herstellung dieser Verbindungen
AT226364B (de)	1963-03-11	Verfahren zur Herstellung von neuen Penicillinderivaten
DE1045392B (de)	1958-12-04	Verfahren zur Herstellung von reinen Verbindungen des Tetracyclins
DE1617434C (de)	1972-01-05	Röntgenkontrastmittel
DE1176147B (de)	1964-08-20	Verfahren zur Herstellung von 7-Aminocephalosporansaeure
AT203153B (de)	1959-05-11	Verfahren zur Herstellung von Peptiden
AT284126B (de)	1970-09-10	Verfahren zur Herstellung neuer substituierter Aminopyrimidine und deren Salze und optisch aktiven Isomere
AT226379B (de)	1963-03-11	Verfahren zur Herstellung von neuen Hydrierungsprodukten der Lysergsäure-Reihe
AT365598B (de)	1982-01-25	Verfahren zur herstellung eines neuen formamidkomplexes von 7-beta-(d-2-phenylacetamido) -3-methylceph-3-emcarbonsaeure