CA2030361A1 - Procede de deplacement pour le 3-fluorosulfonyloxyceph-3-em - Google Patents
Procede de deplacement pour le 3-fluorosulfonyloxyceph-3-emInfo
- Publication number
- CA2030361A1 CA2030361A1 CA2030361A CA2030361A CA2030361A1 CA 2030361 A1 CA2030361 A1 CA 2030361A1 CA 2030361 A CA2030361 A CA 2030361A CA 2030361 A CA2030361 A CA 2030361A CA 2030361 A1 CA2030361 A1 CA 2030361A1
- Authority
- CA
- Canada
- Prior art keywords
- fluorosulfonyloxyceph
- displacement process
- carbon
- organostannanes
- ems
- Prior art date
- 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.)
- Granted
Links
- RGBQNBXVKHBOJY-ZCFIWIBFSA-N (6r)-3-fluorosulfonyloxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene Chemical compound S1CC(OS(=O)(=O)F)=CN2C(=O)C[C@H]21 RGBQNBXVKHBOJY-ZCFIWIBFSA-N 0.000 title 1
- 238000006073 displacement reaction Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- WDLWHQDACQUCJR-ZAMMOSSLSA-N (6r,7r)-7-[[(2r)-2-azaniumyl-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(e)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)/C=C/C)C(O)=O)=CC=C(O)C=C1 WDLWHQDACQUCJR-ZAMMOSSLSA-N 0.000 abstract 1
- 238000010485 C−C bond formation reaction Methods 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 229960002580 cefprozil Drugs 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
Classifications
-
- 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
Landscapes
- 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002147460A CA2147460A1 (fr) | 1989-11-21 | 1990-11-20 | Methode de deplacement du 3-fluorosulfonyloxyceph-3-eme |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43976789A | 1989-11-21 | 1989-11-21 | |
| US439,767 | 1989-11-21 | ||
| US07/603,872 US5245027A (en) | 1989-11-21 | 1990-10-31 | 3-fluorosulfonyloxyceph-3-em compounds |
| US603,872 | 1990-10-31 |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002147461A Division CA2147461A1 (fr) | 1992-10-21 | 1990-11-20 | Analogues de la prostaglandine e1 |
| CA002147460A Division CA2147460A1 (fr) | 1989-11-21 | 1990-11-20 | Methode de deplacement du 3-fluorosulfonyloxyceph-3-eme |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2030361A1 true CA2030361A1 (fr) | 1991-05-22 |
| CA2030361C CA2030361C (fr) | 2001-01-30 |
Family
ID=27032165
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002030361A Expired - Fee Related CA2030361C (fr) | 1989-11-21 | 1990-11-20 | Procede de deplacement pour le 3-fluorosulfonyloxyceph-3-em |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5245027A (fr) |
| EP (1) | EP0431794A3 (fr) |
| JP (1) | JP2964423B2 (fr) |
| KR (1) | KR0148488B1 (fr) |
| AU (1) | AU637650B2 (fr) |
| CA (1) | CA2030361C (fr) |
| FI (1) | FI97545C (fr) |
| HU (2) | HU209309B (fr) |
| IE (1) | IE904191A1 (fr) |
| IL (1) | IL96417A (fr) |
| NO (1) | NO177348C (fr) |
| NZ (1) | NZ236183A (fr) |
| OA (1) | OA09329A (fr) |
| RU (2) | RU2044738C1 (fr) |
Families Citing this family (7)
| 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 |
| CN106659700B (zh) * | 2014-06-06 | 2020-07-10 | 斯克里普斯研究所 | 氟化硫(vi)化合物及其制备方法 |
| KR20170070042A (ko) * | 2014-10-08 | 2017-06-21 | 다우 글로벌 테크놀로지스 엘엘씨 | 제1 화합물을 제2 화합물에 커플링시키는 방법 |
Family Cites Families (8)
| 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 |
| US4847373A (en) * | 1987-02-26 | 1989-07-11 | Bristol-Myers Company | Production of 3-allyl- and 3-butenyl-3-cephems |
| US4820832A (en) * | 1988-03-23 | 1989-04-11 | Eli Lilly And Company | Process for preparing 3-unsubstituted cephalosporins and 1-carba(dethia)cephalosporins |
| US4855418A (en) * | 1988-03-23 | 1989-08-08 | Eli Lilly And Company | Process for production of ceophalosporins |
-
1990
- 1990-10-31 US US07/603,872 patent/US5245027A/en not_active Expired - Lifetime
- 1990-11-19 FI FI905699A patent/FI97545C/fi not_active IP Right Cessation
- 1990-11-20 IL IL9641790A patent/IL96417A/en unknown
- 1990-11-20 NO NO905012A patent/NO177348C/no unknown
- 1990-11-20 CA CA002030361A patent/CA2030361C/fr not_active Expired - Fee Related
- 1990-11-20 EP EP19900312623 patent/EP0431794A3/en not_active Ceased
- 1990-11-20 KR KR1019900018826A patent/KR0148488B1/ko not_active IP Right Cessation
- 1990-11-20 OA OA59898A patent/OA09329A/fr unknown
- 1990-11-20 AU AU66770/90A patent/AU637650B2/en not_active Ceased
- 1990-11-20 IE IE419190A patent/IE904191A1/en unknown
- 1990-11-21 NZ NZ236183A patent/NZ236183A/en unknown
- 1990-11-21 HU HU907221A patent/HU209309B/hu not_active IP Right Cessation
- 1990-11-21 JP JP2314479A patent/JP2964423B2/ja not_active Expired - Fee Related
- 1990-11-21 RU SU904831927A patent/RU2044738C1/ru active
- 1990-11-21 HU HU9303608A patent/HU213400B/hu not_active IP Right Cessation
-
1992
- 1992-09-09 RU SU925052625A patent/RU2070200C1/ru not_active IP Right Cessation
-
1993
- 1993-06-15 US US08/077,825 patent/US5420269A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2030361C (fr) | 2001-01-30 |
| RU2070200C1 (ru) | 1996-12-10 |
| EP0431794A2 (fr) | 1991-06-12 |
| US5245027A (en) | 1993-09-14 |
| RU2044738C1 (ru) | 1995-09-27 |
| FI97545C (fi) | 1997-01-10 |
| KR0148488B1 (ko) | 1998-11-02 |
| OA09329A (fr) | 1992-09-15 |
| FI905699A0 (fi) | 1990-11-19 |
| NO905012L (no) | 1991-05-22 |
| HUT66487A (en) | 1994-11-28 |
| JP2964423B2 (ja) | 1999-10-18 |
| IL96417A (en) | 1995-03-15 |
| NZ236183A (en) | 1992-03-26 |
| AU637650B2 (en) | 1993-06-03 |
| EP0431794A3 (en) | 1992-03-25 |
| FI97545B (fi) | 1996-09-30 |
| HU907221D0 (en) | 1991-05-28 |
| IE904191A1 (en) | 1991-05-22 |
| NO905012D0 (no) | 1990-11-20 |
| KR910009713A (ko) | 1991-06-28 |
| US5420269A (en) | 1995-05-30 |
| AU6677090A (en) | 1991-05-30 |
| HU209309B (en) | 1994-04-28 |
| NO177348C (no) | 1995-08-30 |
| IL96417A0 (en) | 1991-08-16 |
| NO177348B (no) | 1995-05-22 |
| JPH03220195A (ja) | 1991-09-27 |
| FI905699A (fi) | 1991-05-22 |
| HU213400B (en) | 1997-06-30 |
| HU9303608D0 (en) | 1994-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |