JPH072750B2 - ６−Ｄ−α−（４−エチル−２，３−ジオクソ−１−ピペラジノカルボニルアミノ）−フエニルアセトアミド−ペニシラン酸の製造方法 - Google Patents

６−Ｄ−α−（４−エチル−２，３−ジオクソ−１−ピペラジノカルボニルアミノ）−フエニルアセトアミド−ペニシラン酸の製造方法

Info

Publication number: JPH072750B2
Authority: JP; Japan
Prior art keywords: ethyl; water; dioxo; temperature; piperazinocarbonylamino
Prior art date: 1985-08-16
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 - Lifetime

Application number

JP19073986A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62103089A (ja

Inventor

ブラギナ・クレステバ・バシレバールカノバ

スタニスラフ・パブロフ・デイマノフ

リュボミル・ステファノフ・チャンゴフ

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.)

DARUYABUNO SUTOPANSUKO OBEDEINENIE FUAAMAHIMU

Original Assignee

DARUYABUNO SUTOPANSUKO OBEDEINENIE FUAAMAHIMU

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.)

1985-08-16

Filing date

1986-08-15

Publication date

1995-01-18

1986-08-15 Application filed by DARUYABUNO SUTOPANSUKO OBEDEINENIE FUAAMAHIMU filed Critical DARUYABUNO SUTOPANSUKO OBEDEINENIE FUAAMAHIMU

1987-05-13 Publication of JPS62103089A publication Critical patent/JPS62103089A/ja

1995-01-18 Publication of JPH072750B2 publication Critical patent/JPH072750B2/ja

2010-01-18 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
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 14
239000003960 organic solvent Substances 0.000 claims description 14
229960000723 ampicillin Drugs 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
230000010933 acylation Effects 0.000 claims description 9
238000005917 acylation reaction Methods 0.000 claims description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 3
SXVBQOZRZIUHKU-UHFFFAOYSA-N 4-ethyl-2,3-dioxopiperazine-1-carbonyl chloride Chemical compound CCN1CCN(C(Cl)=O)C(=O)C1=O SXVBQOZRZIUHKU-UHFFFAOYSA-N 0.000 claims description 3
230000020477 pH reduction Effects 0.000 claims description 3
239000003929 acidic solution Substances 0.000 claims description 2
238000001816 cooling Methods 0.000 claims description 2
238000004062 sedimentation Methods 0.000 claims description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 claims 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 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
229960002292 piperacillin Drugs 0.000 description 12
WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
239000010410 layer Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 9
239000000243 solution Substances 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
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 5
238000006243 chemical reaction Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
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 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229960003311 ampicillin trihydrate Drugs 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000000151 deposition Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JTXMVXSTHSMVQF-UHFFFAOYSA-N 2-acetyloxyethyl acetate Chemical compound CC(=O)OCCOC(C)=O JTXMVXSTHSMVQF-UHFFFAOYSA-N 0.000 description 2
-1 4-ethyl-2,3-dioxopiperazinocarbonylamino Chemical group 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000005416 organic matter Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
238000006884 silylation reaction Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000005406 washing 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
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
ZBEKOEYCWKIMGU-UHFFFAOYSA-N 1-ethylpiperazine-2,3-dione Chemical compound CCN1CCNC(=O)C1=O ZBEKOEYCWKIMGU-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
241000305071 Enterobacterales Species 0.000 description 1
201000009906 Meningitis Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
241000588767 Proteus vulgaris Species 0.000 description 1
241000589517 Pseudomonas aeruginosa Species 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
241000607720 Serratia Species 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical compound O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229940007042 proteus vulgaris Drugs 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 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)

JP19073986A 1985-08-16 1986-08-15 ６−Ｄ−α−（４−エチル−２，３−ジオクソ−１−ピペラジノカルボニルアミノ）−フエニルアセトアミド−ペニシラン酸の製造方法 Expired - Lifetime JPH072750B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
BG71470		1985-08-16
BG7147085A BG46664A1 (en)	1985-08-16	1985-08-16	Method for preparing of 6- /d (-)- alpha- (4- ethyl- 2, 3- dioxo- 1- piperazine carbonylamino)- phenylacetamido/- penicillanic acid

Publications (2)

Publication Number	Publication Date
JPS62103089A JPS62103089A (ja)	1987-05-13
JPH072750B2 true JPH072750B2 (ja)	1995-01-18

Family

ID=3916056

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP19073986A Expired - Lifetime JPH072750B2 (ja)	1985-08-16	1986-08-15	６−Ｄ−α−（４−エチル−２，３−ジオクソ−１−ピペラジノカルボニルアミノ）−フエニルアセトアミド−ペニシラン酸の製造方法

Country Status (5)

Country	Link
JP (1)	JPH072750B2 (de)
AT (1)	AT392278B (de)
BG (1)	BG46664A1 (de)
DE (1)	DE3627581A1 (de)
GB (1)	GB2179348B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1283530B1 (it) *	1996-07-26	1998-04-21	Ribbon Srl	Procedimento per la preparazione di penicilline
US6207661B1 (en) *	1999-02-22	2001-03-27	Baxter International Inc.	Premixed formulation of piperacillin sodium and tazobactam sodium injection
ITMI20011718A1 (it)	2001-08-03	2003-02-03	Istituto Biochimico Italiano	Processo per la preparazione del sale sodico dell'acido-6(d-(-)-alpha-(4-etil-2,3-diosso-1-piperazinocarbonilammino)fenilacetammido)penicill
JP2007246514A (ja) *	2006-02-14	2007-09-27	Toyama Chem Co Ltd	ピペラシリンナトリウムの新規な結晶
JP4947284B2 (ja) *	2006-10-20	2012-06-06	株式会社ユニオン	建物用扉の把手
JP2008155592A (ja) *	2006-12-26	2008-07-10	Oike Tec Co Ltd	蓄光性積層体及び蓄光糸
MX2009008124A (es) *	2007-01-31	2009-10-08	Toyama Chemical Co Ltd	Cristal nuevo de piperacilina sodica.
EP4722220A1 (de) *	2023-05-31	2026-04-08	FUJIFILM Toyama Chemical Co., Ltd.	Verfahren zur herstellung einer beta-lactam-verbindung

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4379152A (en) *	1974-05-09	1983-04-05	Toyama Chemical Co., Ltd.	Cephalosporins
IL47168A (en) *	1974-05-09	1979-07-25	Toyama Chemical Co Ltd	Mono or dioxo piperazino(thio)carbonylamino derivatives ofpenicillins and cephalosporins and process for producing the same
CA1200239A (en) *	1981-03-30	1986-02-04	Donald C. Boop	Process for preparing 6-¬d-(-)-alpha-(4-c1-c4 alkyl- 2,3-dioxo-1-piperazinocarbonyl-amino)- phenylacetamido\|penicillanic acid
YU43570B (en) *	1984-05-30	1989-08-31	Krka	Process for preparation of derivatives of d()alpha-amino-benzile-penicilyns
PL145700B3 (en) *	1984-08-29	1988-10-31	Tarchominskie Zaklad Farma	Method of obtaining 6-/d/-/alpha-/4-ethyl-2,3-dioxy-1-piperazinylocarbonyloamino/-phenylacetamido/-penicillate sodium salt

1985
- 1985-08-16 BG BG7147085A patent/BG46664A1/xx unknown
1986
- 1986-08-12 AT AT217886A patent/AT392278B/de not_active IP Right Cessation
- 1986-08-14 DE DE19863627581 patent/DE3627581A1/de not_active Ceased
- 1986-08-14 GB GB8619818A patent/GB2179348B/en not_active Expired
- 1986-08-15 JP JP19073986A patent/JPH072750B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
GB2179348B (en)	1989-08-02
JPS62103089A (ja)	1987-05-13
GB8619818D0 (en)	1986-09-24
GB2179348A (en)	1987-03-04
DE3627581A1 (de)	1987-02-19
AT392278B (de)	1991-02-25
BG46664A1 (en)	1990-02-15
ATA217886A (de)	1990-08-15

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CA1049432A (en)	1979-02-27	Process for the preparation of antibacterial agents
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JP2920556B2 (ja)	1999-07-19	２―シアノ―２―置換ヒドロキシイミノアセトアミジンの製造法
KR850000611B1 (ko)	1985-05-01	6-[d(-)-알파-(4-c₁~c₄)알킬-2,3-디옥소-1-피페라지노 카르보닐아미노)페닐아세트아미도] 페니실란산 제조방법
JPH0665254A (ja)	1994-03-08	セフォラニド誘導体
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