AT335603B - Verfahren zur herstellung von neuen penicillan- oder cephalosporansaurederivaten - Google Patents

Verfahren zur herstellung von neuen penicillan- oder cephalosporansaurederivaten

Info

Publication number: AT335603B
Authority: AT; Austria
Prior art keywords: sep; desc; mmol; added; page number
Prior art date: 1972-12-27

Application number

AT1081073A

Other languages

German (de)

English (en)

Other versions

ATA1081073A (de

Original Assignee

Novo Terapeutisk Labor As

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.)

1972-12-27

Filing date

1973-12-27

Publication date

1977-03-25

1973-12-27 Application filed by Novo Terapeutisk Labor As filed Critical Novo Terapeutisk Labor As

1975-11-14 Priority to AT871575A priority Critical patent/AT340593B/de

1976-07-15 Publication of ATA1081073A publication Critical patent/ATA1081073A/de

1977-03-25 Application granted granted Critical

1977-03-25 Publication of AT335603B publication Critical patent/AT335603B/de

Links

238000000034 method Methods 0.000 title description 5
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 title description 2
238000004519 manufacturing process Methods 0.000 title description 2
BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 128
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
238000000655 nuclear magnetic resonance spectrum Methods 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 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000005977 Ethylene Substances 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
OLSFRDLMFAOSIA-UHFFFAOYSA-N 2-chloro-1,3,2-dioxaphospholane Chemical compound ClP1OCCO1 OLSFRDLMFAOSIA-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
-1 amido compound Chemical class 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 4
229940106164 cephalexin Drugs 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 2
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 2
229930186147 Cephalosporin Natural products 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
CNNHUAAVDPMXQQ-UHFFFAOYSA-N P(O)(O)O.C(CCl)Cl Chemical compound P(O)(O)O.C(CCl)Cl CNNHUAAVDPMXQQ-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229940124587 cephalosporin Drugs 0.000 description 2
150000001780 cephalosporins Chemical class 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N isobenzofuranone Natural products C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
150000002960 penicillins Chemical class 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000005051 trimethylchlorosilane Substances 0.000 description 2
MEAZEHJUPLREOQ-SSDOTTSWSA-N (2r)-2-amino-2-phenylacetyl chloride Chemical compound ClC(=O)[C@H](N)C1=CC=CC=C1 MEAZEHJUPLREOQ-SSDOTTSWSA-N 0.000 description 1
QITDACOZCQXYQY-BAFYGKSASA-N (6r)-7-amino-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC=CN2C(=O)C(N)[C@H]21 QITDACOZCQXYQY-BAFYGKSASA-N 0.000 description 1
MEAZEHJUPLREOQ-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride Chemical compound ClC(=O)C(N)C1=CC=CC=C1 MEAZEHJUPLREOQ-UHFFFAOYSA-N 0.000 description 1
GVVFCAFBYHYGEE-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride;hydron;chloride Chemical compound Cl.ClC(=O)C(N)C1=CC=CC=C1 GVVFCAFBYHYGEE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
CSGFFYNMTALICU-ZWNOBZJWSA-N adipyl-7-aminodesacetoxycephalosporanic acid Natural products CC1=C(N2[C@H](SC1)[C@H](NC(=O)CCCCC(O)=O)C2=O)C(O)=O CSGFFYNMTALICU-ZWNOBZJWSA-N 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000003460 beta-lactamyl group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
TXHWYSOQHNMOOU-UHFFFAOYSA-N chloro(diethoxy)phosphane Chemical compound CCOP(Cl)OCC TXHWYSOQHNMOOU-UHFFFAOYSA-N 0.000 description 1
HDITUCONWLWUJR-UHFFFAOYSA-N diethylazanium;chloride Chemical compound [Cl-].CC[NH2+]CC HDITUCONWLWUJR-UHFFFAOYSA-N 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 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
239000012071 phase Substances 0.000 description 1
238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
150000003865 secondary ammonium salts Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
150000003866 tertiary ammonium salts Chemical class 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Cephalosporin Compounds (AREA)

AT1081073A 1972-12-27 1973-12-27 Verfahren zur herstellung von neuen penicillan- oder cephalosporansaurederivaten AT335603B (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
AT871575A AT340593B (de)	1972-12-27	1975-11-14	Verfahren zur herstellung von penicillinen und cephalosporinen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB5970872		1972-12-27

Publications (2)

Publication Number	Publication Date
ATA1081073A ATA1081073A (de)	1976-07-15
AT335603B true AT335603B (de)	1977-03-25

Family

ID=10484272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT1081073A AT335603B (de)	1972-12-27	1973-12-27	Verfahren zur herstellung von neuen penicillan- oder cephalosporansaurederivaten

Country Status (2)

Country	Link
AT (1)	AT335603B (fr)
BE (1)	BE809110A (fr)

1973
- 1973-12-27 AT AT1081073A patent/AT335603B/de not_active IP Right Cessation
- 1973-12-27 BE BE139271A patent/BE809110A/fr unknown

Also Published As

Publication number	Publication date
BE809110A (fr)	1974-04-16
ATA1081073A (de)	1976-07-15

Legal Events

Date	Code	Title	Description
1982-04-15	ELJ	Ceased due to non-payment of the annual fee

Publication	Publication Date	Title
DE2147023A1 (de)	1973-03-29	Verfahren zur herstellung von 1htetrazol-verbindungen
DE2805488C2 (de)	1985-06-27	Tetrahydrofuran-Solvate der Magnesiumhalogenid-Komplexe der &alpha;-Brompropionsäure, Verfahren zu deren Herstellung und deren Weiterverarbeitung zur Herstellung von 2-Arylpropionsäuren
DE2355084A1 (de)	1974-05-16	Verbindungen mit magensaeuresekretionshemmender wirkung und verfahren zu deren herstellung
DE69909165T2 (de)	2004-04-15	Verfahren zur Herstellung von N-Glycyltyrosin
DD151446A5 (de)	1981-10-21	Verfahren zur herstellung von phenylglycylchlorid-hydrochloriden
DE2938065C2 (fr)	1991-03-14
AT340593B (de)	1977-12-27	Verfahren zur herstellung von penicillinen und cephalosporinen
DE2033357B2 (de)	1979-06-07	Palmitoyl-propandiol-(13)-phosphorsäure-5-trimethylaminophenylester und Verfahren zu dessen Herstellung
CH625805A5 (fr)	1981-10-15
DE2364759A1 (de)	1974-07-04	Neue zwischenprodukte zum herstellen von penicillin oder cephalosporin und verfahren zu deren herstellung sowie verfahren zum herstellen von penicillinen oder cephalosporinen oder derivaten hiervon aus diesen zwischenprodukten
DE2546910C3 (de)	1978-09-28	PhosphinylureidopeniciUansäurederivate und ihre Verwendung
DE2033361C3 (de)	1980-02-21	Acylpropandiol-(13)-phosphorsäurecholinester und Verfahren zu deren Herstellung
EP0088252B1 (fr)	1986-04-09	Procédé de préparation de l'acide 1-(4-chlorbenzoyl)-5-méthoxy-2-méthyl-3-indolylacétoxyacétique
AT315365B (de)	1974-04-15	Verfahren zur herstellung von penicillinen
CH535787A (de)	1973-04-15	Verfahren zur Herstellung wasserlöslicher Salze von a-Aminobenzylpenicillin
DE2062296C3 (de)	1975-04-17	Verfahren zur Herstellung von 7-lsocyanato-cephalosporansäurederivaten
AT359989B (de)	1980-12-10	Verfahren zur herstellung von neuen omega- -amino-carbonsaeureamiden und von deren salzen
DE2841363C2 (fr)	1988-08-04
AT215598B (de)	1961-06-12	Verfahren zur Herstellung neuer Tetracyclinverbindungen
DE1931097C3 (de)	1975-05-07	Verfahren zur Herstellung von 6-Isocyana to- penicillansäure derivaten
DE1470083C (de)	1972-08-24	Cinnamylpenicilline und Verfahren zu ihrer Herstellung
DE1940081A1 (de)	1970-05-06	delta?-Cephem-4-carbonsaeureester
DE2449711C3 (de)	1980-08-21	Verfahren zur Herstellung von Asparagin und N-Acetyl-asparagin
AT294851B (de)	1971-12-10	Verfahren zur Herstellung eines neuen Diastereomeren eines Antipoden der (cis-1,2-Epoxypropyl)-phosphonsäure
AT340587B (de)	1977-12-27	Verfahren zur herstellung neuer cephemderivate