ES8107224A1 - Un procedimiento para la preparacion de derivados acidos penem-carboxilicos - Google Patents
Un procedimiento para la preparacion de derivados acidos penem-carboxilicosInfo
- Publication number
- ES8107224A1 ES8107224A1 ES495977A ES495977A ES8107224A1 ES 8107224 A1 ES8107224 A1 ES 8107224A1 ES 495977 A ES495977 A ES 495977A ES 495977 A ES495977 A ES 495977A ES 8107224 A1 ES8107224 A1 ES 8107224A1
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- optionally substituted
- substituted methyl
- esters
- penem
- 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.)
- Expired
Links
- UOUJHHNRTZZABP-ZCFIWIBFSA-N (5r)-3-methyl-4-thia-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class S1C(C)=CN2C(=O)C[C@H]21 UOUJHHNRTZZABP-ZCFIWIBFSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- -1 p.methoxybenzyl Chemical group 0.000 abstract 2
- 230000004913 activation Effects 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003781 beta lactamase inhibitor Substances 0.000 abstract 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 238000001727 in vivo Methods 0.000 abstract 1
- 230000002503 metabolic effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
PROCEDIMIENTO DE PREPARACION DE DERIVADOS ACIDOS PENEM-CARBOXILICOS Y ESTERES DE FORMULA (I), DONDE R'''''''' ES HIDROGENO, ALQUILO INFERIOR, 2,2,2-TRICLOROETILO, ACETONILO U OTROS; Z ES HIDROGENO, HALOGENO, HIDROXILO, AMINO U OTROS, Y R'''''' ES HIDROGENO, ALQUILO INFERIOR, CICLOALQUILO O HIDROXIALQUILO. SE HACE REACCIONAR EN UN DISOLVENTE INERTE, A TEMPERATURA DE 70-140GC, EL ESTER DE S-OXIDO DE ACIDO PENICILANICO DE FORMULA (II), DONDE R ES UN GRUPO ALQUILO, CON UN DERIVADO ACETILENICO, DE FORMULA (III), DONDE Y ES HIDROGENO, ALQUILO INFERIOR, CINAO U OTROS, Y Z'' ES HALOGENO, HIDROGENO, HIDROXILO, AMINO, CARBAMOILOXILO U OTROS. EL COMPUESTO RESULTANTE SE ISOMERIZA EN CONDICIONES BASICAS. SE OZONIZA EL PRODUCTO, SE REDUCE CON TRIBROMURO DE FOSFORO O YODURO SODICO EN CLORURO DE ACETILO Y SE HIDROLIZA EN CONDICIONES BASICAS SUAVES O SOBRE GEL DE SILICE. SE USAN COMO AGENTES ANTIBACTERIANOS E INHIBIDORES DE BETALACTAMASA. *FORMULA* B
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7906634 | 1979-02-24 | ||
| GB7932591 | 1979-09-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8107224A1 true ES8107224A1 (es) | 1981-10-01 |
| ES495977A0 ES495977A0 (es) | 1981-10-01 |
Family
ID=26270697
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES488886A Granted ES488886A0 (es) | 1979-02-24 | 1980-02-23 | Un procedimiento para la preparacion de derivados acidos penemcarboxilicos. |
| ES495977A Granted ES495977A0 (es) | 1979-02-24 | 1980-10-16 | Un procedimiento para la preparacion de derivados acidos penem-carboxilicos |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES488886A Granted ES488886A0 (es) | 1979-02-24 | 1980-02-23 | Un procedimiento para la preparacion de derivados acidos penemcarboxilicos. |
Country Status (24)
| Country | Link |
|---|---|
| AT (1) | AT368506B (es) |
| AU (1) | AU535080B2 (es) |
| CA (2) | CA1154010A (es) |
| CH (2) | CH651570A5 (es) |
| CS (1) | CS226010B2 (es) |
| DE (1) | DE3006273A1 (es) |
| DK (1) | DK159448C (es) |
| ES (2) | ES488886A0 (es) |
| FI (1) | FI75163C (es) |
| FR (1) | FR2449690B1 (es) |
| GB (1) | GB2043639B (es) |
| GR (1) | GR73623B (es) |
| HK (1) | HK74487A (es) |
| HU (1) | HU182664B (es) |
| IE (1) | IE49407B1 (es) |
| IT (1) | IT1193922B (es) |
| LU (1) | LU82192A1 (es) |
| NL (1) | NL192265C (es) |
| NO (1) | NO161000C (es) |
| NZ (1) | NZ192949A (es) |
| PT (1) | PT70849A (es) |
| SE (1) | SE449489B (es) |
| UA (1) | UA6041A1 (es) |
| YU (1) | YU42964B (es) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
| DE3121510A1 (de) * | 1980-07-04 | 1982-06-16 | Farmitalia Carlo Erba S.p.A., 20159 Milano | 6-alkyl-2-subst.-peneme und verfahren zu ihrer herstellung |
| JPS588084A (ja) * | 1981-07-08 | 1983-01-18 | Takeda Chem Ind Ltd | （６ｒ）−置換−（５ｒ）−ペネム−３−カルボン酸誘導体およびその製造法 |
| EP0180252B1 (en) * | 1981-07-15 | 1989-04-26 | Sumitomo Pharmaceuticals Company, Limited | Process of preparing azetidinone compounds |
| NL8204720A (nl) * | 1981-12-11 | 1983-07-01 | Erba Farmitalia | Werkwijze voor het bereiden van optisch actieve penemverbindingen. |
| NO831160L (no) * | 1982-04-08 | 1983-10-10 | Erba Farmitalia | Fremstilling av substituerte penem-derivater |
| PH21930A (en) * | 1982-11-16 | 1988-04-08 | Ciba Geigy Ag | 6-hydroxy-lower alkylpenem compounds,pharmaceutical composition containing same and method of use thereof |
| DE3372968D1 (en) * | 1982-11-16 | 1987-09-17 | Ciba Geigy Ag | Heterocyclyl-thio compounds, process for their preparation, pharmaceutical compositions containing them and their use |
| GB8300295D0 (en) * | 1983-01-06 | 1983-02-09 | Erba Farmitalia | Penem esters |
| JPS59152387A (ja) * | 1983-02-10 | 1984-08-31 | Shionogi & Co Ltd | 新規ペネム化合物 |
| GB8321677D0 (en) * | 1983-08-11 | 1983-09-14 | Erba Farmitalia | Preparation of penems |
| US4656165A (en) * | 1983-09-02 | 1987-04-07 | Ciba-Geigy Corporation | Aminomethyl penem compounds |
| US4711886A (en) * | 1984-07-02 | 1987-12-08 | Merck & Co., Inc. | β-lactam derivatives as anti-inflammatory and antidegenerative agents |
| US4761408A (en) * | 1984-11-02 | 1988-08-02 | Ciba-Geigy Corporation | Crystalline aminomethyl compound |
| DE3882730D1 (de) * | 1987-02-11 | 1993-09-09 | Ciba Geigy Ag | Bicyclische beta-lactam-carbonsaeuren. |
| GB2206578B (en) * | 1987-07-07 | 1991-07-03 | Erba Carlo Spa | Process for the preparation of penems |
| US5364768A (en) * | 1987-07-07 | 1994-11-15 | Farmitalia Carlo Erba S.R.L. | Process for the preparation of penems |
| IT1286558B1 (it) * | 1996-02-27 | 1998-07-15 | Menarini Farma Ind | Processo per la preparazione di 2-alogenometil-penems e loro uso per la preparazione di penems antibatterici |
| US6156745A (en) | 1997-12-29 | 2000-12-05 | Research Corporation Technologies, Inc. | 2β-substituted-6-alkylidene penicillanic acid derivatives as β-lactamase inhibitors |
| US6407091B1 (en) | 1999-04-15 | 2002-06-18 | Research Corporation Technologies, Inc. | β-lactamase inhibiting compounds |
| US6720445B2 (en) * | 2000-12-21 | 2004-04-13 | Beacon Laboratories, Inc. | Acetyloxymethyl esters and methods for using the same |
| ES2272795T3 (es) | 2001-07-24 | 2007-05-01 | Southern Methodist University Foundation For Research | 7-alquildieno-3-sustituidos-3-cefem-4-carboxilatos como inhibidores de beta-lactamasa. |
| JP2005525399A (ja) | 2002-04-04 | 2005-08-25 | アラムクス エルエルシー | セリンおよびメタロ−β−ラクタマーゼの阻害剤 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU77306A1 (es) * | 1977-05-09 | 1979-01-18 | ||
| JPS5439090A (en) * | 1977-07-13 | 1979-03-24 | Glaxo Group Ltd | Betaalactam compound and its preparation |
| US4168314A (en) * | 1977-11-17 | 1979-09-18 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid |
| US4155912A (en) * | 1977-12-14 | 1979-05-22 | Bristol-Myers Company | 2-Methylpenem-3-carboxylic acid antibiotics |
| EP0003415A3 (en) * | 1978-01-20 | 1979-08-22 | Glaxo Group Limited | Beta-lactam compounds, processes for their preparation,compositions containing them and intermediates of use in their preparation |
| EP0003960B1 (de) * | 1978-02-02 | 1983-06-29 | Ciba-Geigy Ag | 6-Substituierte Thia-Azaverbindungen, ihre Herstellung und diese enthaltende pharmazeutische Präparate |
| EP0010358A1 (en) * | 1978-09-20 | 1980-04-30 | Glaxo Group Limited | Beta-lactam compounds, processes for their preparation, compositions containing them, intermediates of use in their preparation and methods for the production thereof |
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
| EP0013067A1 (en) * | 1978-12-22 | 1980-07-09 | Beecham Group Plc | Bicyclic beta-lactam antibacterial agents, their use in pharmaceutical compositions, processes for their preparation and intermediates for use in such processes |
-
1980
- 1980-02-19 GB GB8005476A patent/GB2043639B/en not_active Expired
- 1980-02-19 GR GR61228A patent/GR73623B/el unknown
- 1980-02-19 AT AT0091980A patent/AT368506B/de not_active IP Right Cessation
- 1980-02-19 FI FI800493A patent/FI75163C/fi not_active IP Right Cessation
- 1980-02-19 AU AU55670/80A patent/AU535080B2/en not_active Ceased
- 1980-02-19 IT IT20021/80A patent/IT1193922B/it active
- 1980-02-19 NL NL8001012A patent/NL192265C/nl not_active IP Right Cessation
- 1980-02-20 DE DE19803006273 patent/DE3006273A1/de active Granted
- 1980-02-20 PT PT70849A patent/PT70849A/pt not_active IP Right Cessation
- 1980-02-20 IE IE338/80A patent/IE49407B1/en not_active IP Right Cessation
- 1980-02-20 YU YU461/80A patent/YU42964B/xx unknown
- 1980-02-20 CA CA000346011A patent/CA1154010A/en not_active Expired
- 1980-02-21 CH CH1400/80A patent/CH651570A5/de not_active IP Right Cessation
- 1980-02-21 CH CH2794/84A patent/CH654831A5/de not_active IP Right Cessation
- 1980-02-22 FR FR8003938A patent/FR2449690B1/fr not_active Expired
- 1980-02-22 UA UA2886007A patent/UA6041A1/uk unknown
- 1980-02-22 NZ NZ192949A patent/NZ192949A/en unknown
- 1980-02-22 HU HU80420A patent/HU182664B/hu not_active IP Right Cessation
- 1980-02-22 LU LU82192A patent/LU82192A1/fr unknown
- 1980-02-22 SE SE8001424A patent/SE449489B/sv not_active IP Right Cessation
- 1980-02-22 NO NO800501A patent/NO161000C/no unknown
- 1980-02-22 DK DK077580A patent/DK159448C/da not_active IP Right Cessation
- 1980-02-22 CS CS801241A patent/CS226010B2/cs unknown
- 1980-02-23 ES ES488886A patent/ES488886A0/es active Granted
- 1980-10-16 ES ES495977A patent/ES495977A0/es active Granted
-
1986
- 1986-01-14 CA CA000499579A patent/CA1212665B/en not_active Expired
-
1987
- 1987-10-15 HK HK744/87A patent/HK74487A/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PC1A | Transfer granted |