FI97545B - Förfarande för framställning av ett cefalosporinantibiotikum samt en mellanprodukt, som är användbar i detta förfarande - Google Patents

Förfarande för framställning av ett cefalosporinantibiotikum samt en mellanprodukt, som är användbar i detta förfarande Download PDF

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Publication number
FI97545B
FI97545B FI905699A FI905699A FI97545B FI 97545 B FI97545 B FI 97545B FI 905699 A FI905699 A FI 905699A FI 905699 A FI905699 A FI 905699A FI 97545 B FI97545 B FI 97545B
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FI
Finland
Prior art keywords
formula
compound
amino
palladium
cephem
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FI905699A
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English (en)
Finnish (fi)
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FI905699A0 (sv
FI97545C (sv
FI905699A (sv
Inventor
Stephen Richard Baker
Jr Chester Sapino
Gregory Paul Roth
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Squibb Bristol Myers Co
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Application filed by Squibb Bristol Myers Co filed Critical Squibb Bristol Myers Co
Publication of FI905699A0 publication Critical patent/FI905699A0/sv
Publication of FI905699A publication Critical patent/FI905699A/sv
Application granted granted Critical
Publication of FI97545B publication Critical patent/FI97545B/sv
Publication of FI97545C publication Critical patent/FI97545C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D505/00—Heterocyclic compounds containing 5-oxa-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • 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
    • C07D501/59—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3 with hetero atoms directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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
    • C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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 with hetero atoms directly attached in position 7
    • C07D463/16—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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
    • C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with 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 with hetero atoms directly attached in position 7
    • C07D463/16—Nitrogen atoms
    • C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
    • C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D463/22—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen further substituted by nitrogen atoms
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (9)

1. Förening, kännetecknad av, att den har formeln 5 Q-HH^2 (I) C02P 10 i vilken Z är svavel eller metylen; Q är fenoxiacetyl, fenylacetyl, 2-amino-2-fenyl-acetyl, 2-amino-2-(4-hydroxifenyl)acetyl eller bensyloxi-15 karbonyl; och P är t-butyl, difenylmetyl eller 4-metoxikarbonyl.
2. Förening enligt patentkrav 1, kännetecknad av, att Z är svavel.
3. Förening enligt patentkrav 1, k ä n n e - 20 tecknad av, att Z är metylen.
4. t-butyl-7-[(bensyloxikarbonyl)amino]-3-[(fluor-sulfonyl)oxi]-l-karba(l-detia)-3-cefem-4-karboxylat.
5. Förfarande för framställning av ett cefalospo-rinantibiotikum med formeln ::: (III) co2p : 30 • # · i vilken Z är svavel eller metylen; Q är fenoxiacetyl, fenylacetyl, 2-amino-2-fenylace-tyl, 2-amino-2-(4-hydroxifenyl)acetyl eller bensyloxikar-35 bonyl; 97545 P är t-butyl, difenylmetyl eller 4-metoxikarbonyl; och R1 är C2_6-alkenyl, kännetecknat av, att en förening med formeln 5 «-»{'N
10 C02P i vilken Q, Z och P är ovan definierade och L är fluor-sulfonyloxi, 4-nitrobensensulfonyloxi eller 4-bromfenyl-sulfonyloxi, bringas att reagera med en organotennförening 15 med formeln R1-Sn-R23, i vilken R1 är ovan definierad och R2 är en C1.6-alkyl, utan tillsats av fosfinligand och me-tallhalogenid i ett inert, aprotiskt lösningsmedel i när-varo av 1 - 10-molprocentisk mängd av en Pd(II)- eller Pd(0)-katalyt. 20
6. Förfarande enligt patentkrav 5, känne tecknat av, att Pd(II)-katalyten är palladium( II)- acetat.
7. Förfarande enligt patentkrav 5, kännetecknat av, att organotennföreningen är vinyltri-25 butyltenn, Z-l-propenyltributyltenn, 2-metyl-l-propenyl- * · · ’·· · tenn eller 1-propenyltributyltenn.
• « *·.'* 8. Förfarande enligt patentkrav 5, k ä n n e - • · · V ' t e c k n a t av, att det aprotiska lösningsmedlet är 1- metyl-2-pyrrolidinon, metylenklorid eller acetonitril. : : : 30
9. Förfarande enligt patentkrav 5, k ä n n e - t e c k n a t av, att Pd( II )-katalyten är tris(dibensy-lidenaceton )dipalladium.
FI905699A 1989-11-21 1990-11-19 Förfarande för framställning av ett cefalosporinantibiotikum samt en mellanprodukt, som är användbar i detta förfarande FI97545C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US43976789A 1989-11-21 1989-11-21
US43976789 1989-11-21
US07/603,872 US5245027A (en) 1989-11-21 1990-10-31 3-fluorosulfonyloxyceph-3-em compounds
US60387290 1990-10-31

Publications (4)

Publication Number Publication Date
FI905699A0 FI905699A0 (sv) 1990-11-19
FI905699A FI905699A (sv) 1991-05-22
FI97545B true FI97545B (sv) 1996-09-30
FI97545C FI97545C (sv) 1997-01-10

Family

ID=27032165

Family Applications (1)

Application Number Title Priority Date Filing Date
FI905699A FI97545C (sv) 1989-11-21 1990-11-19 Förfarande för framställning av ett cefalosporinantibiotikum samt en mellanprodukt, som är användbar i detta förfarande

Country Status (14)

Country Link
US (2) US5245027A (sv)
EP (1) EP0431794A3 (sv)
JP (1) JP2964423B2 (sv)
KR (1) KR0148488B1 (sv)
AU (1) AU637650B2 (sv)
CA (1) CA2030361C (sv)
FI (1) FI97545C (sv)
HU (2) HU213400B (sv)
IE (1) IE904191A1 (sv)
IL (1) IL96417A (sv)
NO (1) NO177348C (sv)
NZ (1) NZ236183A (sv)
OA (1) OA09329A (sv)
RU (2) RU2044738C1 (sv)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3224279B2 (ja) * 1992-07-27 2001-10-29 大塚化学株式会社 セフエム化合物の製造法
JP4510957B2 (ja) * 1999-09-01 2010-07-28 大塚化学株式会社 セフェム化合物の製造方法
KR100459387B1 (ko) * 2001-10-29 2004-12-03 한동기 인스탄트 돈가스 소스용 조성물 및 레토르트파우치 제품제조방법
JP5443118B2 (ja) 2009-03-31 2014-03-19 三菱マテリアル株式会社 ビス（フルオロスルホニル）イミド塩の製造方法、ビス（フルオロスルホニル）イミド塩及びフルオロ硫酸塩の製造方法、並びにビス（フルオロスルホニル）イミド・オニウム塩の製造方法
CN102718714B (zh) * 2012-06-26 2014-09-17 天津师范大学 蒽桥联的四齿咪唑盐及其制备方法与应用
AU2015269198B2 (en) * 2014-06-06 2020-12-10 The Scripps Research Institute Sulfur(VI) fluoride compounds and methods for the preparation thereof
JP2017531650A (ja) * 2014-10-08 2017-10-26 ダウ グローバル テクノロジーズ エルエルシー 第１の化合物を第２の化合物にカップリングさせるための方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR207327A1 (es) * 1974-02-06 1976-09-30 Lilly Co Eli Un procedimiento para preparar acidos 3-cefem 3-sulfonatos y sus esteres
US4520022A (en) * 1983-01-28 1985-05-28 Bristol-Myers Company Substituted vinyl cephalosporins
AU575854B2 (en) * 1983-10-04 1988-08-11 Shionogi & Co., Ltd. 7beta-(carboxyalkenamido) cephalosporins
AU580855B2 (en) * 1985-03-29 1989-02-02 Shionogi & Co., Ltd. Alkeneamidocephalosporin esters
US4820816A (en) * 1985-08-02 1989-04-11 President And Fellows Of Harvard College 3-trifuoromethylsulfonyloxy-substituted 1-carbacephalosporins as intermediates for antibiotics
US4870168A (en) * 1987-02-26 1989-09-26 Bristol-Myers Company 3-Unsaturated alkyl cephems from 3-triflyl cephems
US4855418A (en) * 1988-03-23 1989-08-08 Eli Lilly And Company Process for production of ceophalosporins
US4820832A (en) * 1988-03-23 1989-04-11 Eli Lilly And Company Process for preparing 3-unsubstituted cephalosporins and 1-carba(dethia)cephalosporins

Also Published As

Publication number Publication date
FI905699A0 (sv) 1990-11-19
FI97545C (sv) 1997-01-10
OA09329A (fr) 1992-09-15
EP0431794A2 (en) 1991-06-12
RU2044738C1 (ru) 1995-09-27
NZ236183A (en) 1992-03-26
AU6677090A (en) 1991-05-30
NO905012L (no) 1991-05-22
HU209309B (en) 1994-04-28
FI905699A (sv) 1991-05-22
US5245027A (en) 1993-09-14
AU637650B2 (en) 1993-06-03
JP2964423B2 (ja) 1999-10-18
HU213400B (en) 1997-06-30
US5420269A (en) 1995-05-30
NO177348C (no) 1995-08-30
HU9303608D0 (en) 1994-04-28
IL96417A (en) 1995-03-15
CA2030361A1 (en) 1991-05-22
KR0148488B1 (ko) 1998-11-02
IL96417A0 (en) 1991-08-16
NO177348B (no) 1995-05-22
CA2030361C (en) 2001-01-30
EP0431794A3 (en) 1992-03-25
HU907221D0 (en) 1991-05-28
KR910009713A (ko) 1991-06-28
HUT66487A (en) 1994-11-28
RU2070200C1 (ru) 1996-12-10
NO905012D0 (no) 1990-11-20
IE904191A1 (en) 1991-05-22
JPH03220195A (ja) 1991-09-27

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BB Publication of examined application
FG Patent granted

Owner name: BRISTOL-MYERS SQUIBB COMPANY

MA Patent expired