CA1127150A - Methode d'extraction de cephaloridine des solutions aqueuses qui l'engendrent - Google Patents

Methode d'extraction de cephaloridine des solutions aqueuses qui l'engendrent

Info

Publication number: CA1127150A
Authority: CA; Canada
Prior art keywords: cephaloridine; solution; salt; crystalline; process according
Prior art date: 1978-11-28
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

Application number

CA340,694A

Other languages

English (en)

Inventor

Leone Dall'asta

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Proter SpA

Original Assignee

Proter SpA

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.)

1978-11-28

Filing date

1979-11-27

Publication date

1982-07-06

1979-11-27 Application filed by Proter SpA filed Critical Proter SpA

1982-07-06 Application granted granted Critical

1982-07-06 Publication of CA1127150A publication Critical patent/CA1127150A/fr

Status Expired legal-status Critical Current

Links

CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 title claims abstract description 66
229960003866 cefaloridine Drugs 0.000 title claims abstract description 48
238000000034 method Methods 0.000 title claims abstract description 20
239000007864 aqueous solution Substances 0.000 title claims abstract description 18
238000011084 recovery Methods 0.000 title claims abstract description 7
239000000243 solution Substances 0.000 claims abstract description 29
238000002425 crystallisation Methods 0.000 claims abstract description 15
238000001914 filtration Methods 0.000 claims abstract description 11
238000007792 addition Methods 0.000 claims abstract description 8
238000000354 decomposition reaction Methods 0.000 claims abstract description 8
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 8
238000010899 nucleation Methods 0.000 claims abstract description 7
238000005406 washing Methods 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 6
238000001035 drying Methods 0.000 claims abstract description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
229920005989 resin Polymers 0.000 claims description 7
239000011347 resin Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
229920001429 chelating resin Polymers 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
125000000129 anionic group Chemical group 0.000 claims description 4
235000019441 ethanol Nutrition 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 3
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
150000001298 alcohols Chemical class 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
229940043265 methyl isobutyl ketone Drugs 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
150000003839 salts Chemical class 0.000 description 9
239000013078 crystal Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
239000003929 acidic solution Substances 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 3
229930186147 Cephalosporin Natural products 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
239000007857 degradation product Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
241001296096 Probles Species 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
238000010981 drying operation Methods 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA340,694A 1978-11-28 1979-11-27 Methode d'extraction de cephaloridine des solutions aqueuses qui l'engendrent Expired CA1127150A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT30274/78A IT1101437B (it)	1978-11-28	1978-11-28	Procedimento per il recupero di cefaloridina da soluzione acquosa nella quale e'stata prodotta
IT30274A/78		1978-11-28

Publications (1)

Publication Number	Publication Date
CA1127150A true CA1127150A (fr)	1982-07-06

Family

ID=11229447

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA340,694A Expired CA1127150A (fr)	1978-11-28	1979-11-27	Methode d'extraction de cephaloridine des solutions aqueuses qui l'engendrent

Country Status (3)

Country	Link
JP (1)	JPS5573691A (fr)
CA (1)	CA1127150A (fr)
IT (1)	IT1101437B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3919259A1 (de) *	1989-06-13	1990-12-20	Hoechst Ag	Kristalline cephem-saeureadditionssalze und verfahren zu ihrer herstellung

1978
- 1978-11-28 IT IT30274/78A patent/IT1101437B/it active
1979
- 1979-11-27 CA CA340,694A patent/CA1127150A/fr not_active Expired
- 1979-11-27 JP JP15347779A patent/JPS5573691A/ja active Pending

Also Published As

Publication number	Publication date
JPS5573691A (en)	1980-06-03
IT7830274A0 (it)	1978-11-28
IT1101437B (it)	1985-09-28

Legal Events

Date	Code	Title	Description
1999-07-06	MKEX	Expiry

Publication	Publication Date	Title
US4894476A (en)	1990-01-16	Gabapentin monohydrate and a process for producing the same
DE2760271C2 (fr)	1988-08-18
DE2812625C2 (fr)	1990-08-23
AT392472B (de)	1991-04-10	Verfahren zur herstellung eines stabilen kristallinen di- oder trihydrats der 7beta- ((z)-2-(2-aminothiazol-4-yl)-4-carboxybut-2- enoylamino)-3-cephem-4-carbonsaeure
EP0112550B1 (fr)	1990-02-07	Sels d'addition d'acides cristallins de céphalosporines et procédé pour leur préparation
US4960931A (en)	1990-10-02	Gabapentin mohohydrate and a process for producing the same
DE1545915B2 (de)	1977-06-23	Verfahren zur herstellung von 3- hydroxymethylcephalosporinen
KR100200242B1 (ko)	1999-06-15	클라불란산염의 제조 방법
KR870000829B1 (ko)	1987-04-23	세프타지딤 결정성염의 제조방법
EP0078532A2 (fr)	1983-05-11	Sels cristallins de céfodizim et procédé pour leur préparation
CA1127150A (fr)	1982-07-06	Methode d'extraction de cephaloridine des solutions aqueuses qui l'engendrent
US5625058A (en)	1997-04-29	Process for the preparation of cephalosporins
DE1670113B2 (de)	1976-07-22	Ester der 6-aminopenicillansaeure und verfahren zu ihrer herstellung
DE2356122C2 (de)	1983-12-22	N-Chlorbenzoyl-cephalosporin C-Derivate und Verfahren zu ihrer Herstellung
AT392643B (de)	1991-05-10	Verfahren zur herstellung von neuen derivaten der 7-(d-2-amino-2-(4-hydroxyphenyl)-acetamido)-3- ((z)-1-propenyl)ceph-3-em-4-carbonsaeure
DE3150288C2 (fr)	1990-07-05
DE2738711A1 (de)	1978-03-02	Cephalosporinderivate
DE2550121A1 (de)	1976-05-20	Synthese von racemischem 2-deutero- 3-fluoralanin und dessen salzen sowie dabei auftretende zwischenprodukte
US3947414A (en)	1976-03-30	Cefamandole derivatives
US4458070A (en)	1984-07-03	Process for the manufacture of crystalline sodium cefoperazone
DE3871542T2 (de)	1992-12-24	Verfahren zur herstellung von ceftazidime-pentahydrat.
DE2255973A1 (de)	1973-05-24	Verfahren zur gewinnung von cephalosporin c
DE69700617T2 (de)	2000-03-16	Verfahren zur Herstellung von Cephalosporinen
CA1238318A (fr)	1988-06-21	Double sel, procede de preparation et compose pharmaceutique le contenant
DE4244069A1 (de)	1994-06-30	Cephalosporinsalze und Verfahren zu deren Herstellung