CA1050970A - PROCEDE POUR LA PRODUCTION D'ACIDE 7-(D-(.alpha.-AMINO)-PHENYLACETAMIDO)-3-DESACETOXY-CEPHALOSPORANIQUE - Google Patents

PROCEDE POUR LA PRODUCTION D'ACIDE 7-(D-(.alpha.-AMINO)-PHENYLACETAMIDO)-3-DESACETOXY-CEPHALOSPORANIQUE

Info

Publication number: CA1050970A
Authority: CA; Canada
Prior art keywords: product; urea; acid; solution; acetonitrile
Prior art date: 1975-05-27
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

CA239,168A

Other languages

English (en)

Other versions

CA239168S (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.)

1975-05-27

Filing date

1975-11-07

Publication date

1979-03-20

1975-11-07 Application filed by Proter SpA filed Critical Proter SpA

1979-03-20 Application granted granted Critical

1979-03-20 Publication of CA1050970A publication Critical patent/CA1050970A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 17
238000004519 manufacturing process Methods 0.000 title claims description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 54
239000000047 product Substances 0.000 claims abstract description 27
239000002253 acid Substances 0.000 claims abstract description 23
239000004202 carbamide Substances 0.000 claims abstract description 19
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 14
239000003795 chemical substances by application Substances 0.000 claims abstract description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
239000007859 condensation product Substances 0.000 claims abstract description 6
GVVFCAFBYHYGEE-OGFXRTJISA-N (2r)-2-amino-2-phenylacetyl chloride;hydron;chloride Chemical compound Cl.ClC(=O)[C@H](N)C1=CC=CC=C1 GVVFCAFBYHYGEE-OGFXRTJISA-N 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
238000006884 silylation reaction Methods 0.000 claims abstract description 4
230000007062 hydrolysis Effects 0.000 claims abstract description 3
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 3
238000000926 separation method Methods 0.000 claims abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
238000001556 precipitation Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical group C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 claims 2
MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical group C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 claims 1
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 claims 1
229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
NVIAYEIXYQCDAN-HWZXHQHMSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 abstract 3
230000003115 biocidal effect Effects 0.000 description 6
239000003242 anti bacterial agent Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
125000006519 CCH3 Chemical group 0.000 description 2
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 2
COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 2
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000004448 titration Methods 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
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
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
101100481176 Bacillus subtilis (strain 168) thiE gene Proteins 0.000 description 1
241000518994 Conta Species 0.000 description 1
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
101100494344 Desulfobacterium autotrophicum (strain ATCC 43914 / DSM 3382 / HRM2) bzaF gene Proteins 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
229940022682 acetone Drugs 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
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 1
229940106164 cephalexin Drugs 0.000 description 1
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 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
101150029215 thiC gene Proteins 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Cephalosporin Compounds (AREA)

CA239,168A 1975-05-27 1975-11-07 PROCEDE POUR LA PRODUCTION D'ACIDE 7-(D-(.alpha.-AMINO)-PHENYLACETAMIDO)-3-DESACETOXY-CEPHALOSPORANIQUE Expired CA1050970A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB2314575A GB1459807A (en)	1975-05-27	1975-05-27	Process for the production of 7-d-a-amino-phenyl-acetamido-3- desacetoxy-cephalosporanic acid

Publications (1)

Publication Number	Publication Date
CA1050970A true CA1050970A (fr)	1979-03-20

Family

ID=10190894

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA239,168A Expired CA1050970A (fr)	1975-05-27	1975-11-07	PROCEDE POUR LA PRODUCTION D'ACIDE 7-(D-(.alpha.-AMINO)-PHENYLACETAMIDO)-3-DESACETOXY-CEPHALOSPORANIQUE

Country Status (3)

Country	Link
CA (1)	CA1050970A (fr)
ES (1)	ES438780A1 (fr)
GB (1)	GB1459807A (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1053312B (it) *	1976-01-15	1981-08-31	Ankerfarm Spa	Procedimento per la produzione di antibiotici di penicillina semisintetici
US4278600A (en)	1979-03-19	1981-07-14	Bristol-Myers Company	Production of penicillins
US4248780A (en) *	1979-08-21	1981-02-03	Canada Packers Limited	Process for preparing ampicillin
YU44832B (en) *	1981-08-03	1991-04-30	Pliva Pharm & Chem Works	Process for preparing semisynthetic cephalosporins
IT1180207B (it) *	1984-07-30	1987-09-23	Istituto Biochimico Italiano	Procedimento per la preparazione, con resa e purezza elevate, di antibiotici beta-lattamici
HU221200B1 (en) *	1990-01-22	2002-08-28	Biochemie Gmbh	Process for producing beta-lactames
GB9115203D0 (en) *	1991-07-15	1991-08-28	Biochemie Gmbh	Improvements in or relating to beta lactam production
GB9423459D0 (en) *	1994-11-21	1995-01-11	Biochemie Gmbh	Silylation process
EP0953569A1 (fr) *	1998-04-29	1999-11-03	Gist-Brocades B.V.	Préparation d'antibiotiques béta-lactamiques en présence d'urée ou d'amide

1975
- 1975-05-27 GB GB2314575A patent/GB1459807A/en not_active Expired
- 1975-06-21 ES ES438780A patent/ES438780A1/es not_active Expired
- 1975-11-07 CA CA239,168A patent/CA1050970A/fr not_active Expired

Also Published As

Publication number	Publication date
GB1459807A (en)	1976-12-31
ES438780A1 (es)	1977-03-16

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US20050119244A1 (en)	2005-06-02	Process for preparing cephalosporins with salified intermediate
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US20070244315A1 (en)	2007-10-18	Process for the preparation of cefdinir
US3957773A (en)	1976-05-18	Process for preparing cephalosporin compounds from 7-adca
JPH069647A (ja)	1994-01-18	新規なセファロスポリン中間体
EP0547646A2 (fr)	1993-06-23	Forme cristalline d'une céphalosporine antibiotique
JP3658000B2 (ja)	2005-06-08	７−アミノセファロスポラン酸（７−ａｃａ）の改良された沈殿方法
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PL167897B1 (pl)	1995-12-30	Sposób wytwarzania czystej oksytetracykliny PL PL PL
US4035361A (en)	1977-07-12	Bis-trimethylsilyl cefamandole and process therefor
JP2008520596A (ja)	2008-06-19	純粋なセフジニルの調製のための中間体としてのセフジニルアンモニウム塩の結晶性の形態
JPS58126891A (ja)	1983-07-28	セフアロスポリン化合物
CA1161429A (fr)	1984-01-31	Acides 2-(2-aminothiazol-4-y1)-n-(imidazolidin-2- on-1-yl)-2-imino-acetylaminocephalosporaniques sous forme d'isomere syn; methode pour les preparer, et acide syn utilise dans cette methode
JP2723591B2 (ja)	1998-03-09	７―／Ｄ（―）アルフア―アミノ―アルフア―（ｐ―ヒドロキシフエニル）アセトアミド／―３―メチル―３―セフエム―４―カルボン酸―水化物の製造方法
US4304909A (en)	1981-12-08	Process for producing 7-(D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(4-hydroxyphenyl)acetamido)-3-(5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl)-.DELTA.3 -cephem-4-carboxylic acid and a pharmaceutically acceptable salt thereof
KR870002003B1 (ko)	1987-11-30	7-(d-2-포밀옥시-2-페닐아세트아미도)-3-(1-메틸-1h-테트라졸-5-일티오메틸)-3-세펨-4-카복실산 유도체의 신규 제조방법
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KR860000345B1 (ko)	1986-04-12	세팔로스포린 유도체의 제조방법