SE8001424L - ANTI-BACTERIAL AGENTS AND BETA LACTAM INHIBITORS AND PROCEDURES FOR THEIR PRODUCTION - Google Patents
ANTI-BACTERIAL AGENTS AND BETA LACTAM INHIBITORS AND PROCEDURES FOR THEIR PRODUCTIONInfo
- Publication number
- SE8001424L SE8001424L SE8001424A SE8001424A SE8001424L SE 8001424 L SE8001424 L SE 8001424L SE 8001424 A SE8001424 A SE 8001424A SE 8001424 A SE8001424 A SE 8001424A SE 8001424 L SE8001424 L SE 8001424L
- Authority
- SE
- Sweden
- Prior art keywords
- lower alkyl
- procedures
- production
- bacterial agents
- beta lactam
- Prior art date
Links
- 239000003242 anti bacterial agent Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title 1
- 150000003952 β-lactams Chemical class 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
- 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
- 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
There are provided penem- carboxylic acids and esters of the general formula <IMAGE> In the formula, n=0 or 1; R''=H, lower alkyl, CCl3CH2-, p.nitrobenzyl, p.methoxybenzyl, phenyl, p.nitrophenyl or benzhydryl or a residue known to undergo metabolic activation in vivo and having favourable pharmacokinetic properties; Z=H, halogen, OH, NH2, NH2COO, SH or pyridinium or OR1, OCOR1, NHCOR1 or SR1 wherein R1=lower alkyl, aryl or a heterocyclic ring, each of which may be substituted or unsubstituted; R'=H, lower alkyl, lower alkoxy cycloalkyl or hydroxyalkyl (the hydroxy group of which is free or protected). Pharmaceutically acceptable salts of these compounds, which are antibacterial agents and beta -lactamase inhibitors, are included in the invention, as is a process for their preparation from penicillanic acid S-oxide esters.
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 |
|---|---|
| SE8001424L true SE8001424L (en) | 1980-08-25 |
| SE449489B SE449489B (en) | 1987-05-04 |
Family
ID=26270697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8001424A SE449489B (en) | 1979-02-24 | 1980-02-22 | BETA-LAKTAM ASSOCIATES WITH ANTIBACTERIAL AND BETA-LACTAM INHIBITIVE ACTIVITY |
Country Status (24)
| Country | Link |
|---|---|
| AT (1) | AT368506B (en) |
| AU (1) | AU535080B2 (en) |
| CA (2) | CA1154010A (en) |
| CH (2) | CH654831A5 (en) |
| CS (1) | CS226010B2 (en) |
| DE (1) | DE3006273A1 (en) |
| DK (1) | DK159448C (en) |
| ES (2) | ES8200685A1 (en) |
| FI (1) | FI75163C (en) |
| FR (1) | FR2449690B1 (en) |
| GB (1) | GB2043639B (en) |
| GR (1) | GR73623B (en) |
| HK (1) | HK74487A (en) |
| HU (1) | HU182664B (en) |
| IE (1) | IE49407B1 (en) |
| IT (1) | IT1193922B (en) |
| LU (1) | LU82192A1 (en) |
| NL (1) | NL192265C (en) |
| NO (1) | NO161000C (en) |
| NZ (1) | NZ192949A (en) |
| PT (1) | PT70849A (en) |
| SE (1) | SE449489B (en) |
| UA (1) | UA6041A1 (en) |
| YU (1) | YU42964B (en) |
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 (en) * | 1980-07-04 | 1982-06-16 | Farmitalia Carlo Erba S.p.A., 20159 Milano | 6-Alkyl-2-subst. penems and process for their preparation |
| JPS588084A (en) * | 1981-07-08 | 1983-01-18 | Takeda Chem Ind Ltd | (6r)-substituted-(5r)-penem-3-carboxylic acid derivative and its preparation |
| EP0070204B1 (en) * | 1981-07-15 | 1987-11-19 | Sumitomo Pharmaceuticals Company, Limited | Carboxylic beta-lactam compounds and the preparation thereof |
| US4508649A (en) * | 1981-12-11 | 1985-04-02 | Farmitalia Carlo Erba | Process for preparing optically active penems |
| NO831160L (en) * | 1982-04-08 | 1983-10-10 | Erba Farmitalia | PREPARATION OF SUBSTITUTED PENEM DERIVATIVES |
| 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 (en) * | 1983-02-10 | 1984-08-31 | Shionogi & Co Ltd | Novel penem compound |
| 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 (en) * | 1987-02-11 | 1993-09-09 | Ciba Geigy Ag | BICYCLIC BETA LACTAM CARBON ACIDS. |
| 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 (en) * | 1996-02-27 | 1998-07-15 | Menarini Farma Ind | PROCESS FOR THE PREPARATION OF 2-HALOGENOMETHYL-PENEMS AND THEIR USE FOR THE PREPARATION OF ANTIBACTERIAL PENEMS |
| DE69805975T2 (en) | 1997-12-29 | 2002-12-19 | Res Corp Technologies Inc | 2-BETA-SUBSTITUTED-6-ALKYLIDENPENICILIC ACID DERIVATIVES AS BETA 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 |
| CA2454413A1 (en) | 2001-07-24 | 2003-03-13 | Alamx, L.L.C. | 7-alkylidene-3-substituted-3-cephem-4-carboxylates as beta-lactamase inhibitors |
| JP2005525399A (en) | 2002-04-04 | 2005-08-25 | アラムクス エルエルシー | Inhibitors of serine and metallo-β-lactamases |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU77306A1 (en) * | 1977-05-09 | 1979-01-18 | ||
| EP0000636A1 (en) * | 1977-07-13 | 1979-02-07 | Glaxo Group Limited | Penem compounds, processes for their preparation, their use in pharmaceutical compositions and azetidinones used in their 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 |
| JPS54117459A (en) * | 1978-01-20 | 1979-09-12 | Glaxo Group Ltd | Novel lactam compound |
| EP0003960B1 (en) * | 1978-02-02 | 1983-06-29 | Ciba-Geigy Ag | 6-substituted thia-aza-compounds, their preparation and pharmaceutical compositions containing them |
| JPS5559193A (en) * | 1978-09-20 | 1980-05-02 | Glaxo Group Ltd | Bblactam compound |
| 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 NL NL8001012A patent/NL192265C/en not_active IP Right Cessation
- 1980-02-19 FI FI800493A patent/FI75163C/en 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/en active
- 1980-02-19 GR GR61228A patent/GR73623B/el unknown
- 1980-02-19 AT AT0091980A patent/AT368506B/en not_active IP Right Cessation
- 1980-02-20 PT PT70849A patent/PT70849A/en not_active IP Right Cessation
- 1980-02-20 DE DE19803006273 patent/DE3006273A1/en active Granted
- 1980-02-20 IE IE338/80A patent/IE49407B1/en not_active IP Right Cessation
- 1980-02-20 YU YU461/80A patent/YU42964B/en unknown
- 1980-02-20 CA CA000346011A patent/CA1154010A/en not_active Expired
- 1980-02-21 CH CH2794/84A patent/CH654831A5/en not_active IP Right Cessation
- 1980-02-21 CH CH1400/80A patent/CH651570A5/en not_active IP Right Cessation
- 1980-02-22 HU HU80420A patent/HU182664B/en not_active IP Right Cessation
- 1980-02-22 SE SE8001424A patent/SE449489B/en not_active IP Right Cessation
- 1980-02-22 LU LU82192A patent/LU82192A1/en unknown
- 1980-02-22 UA UA2886007A patent/UA6041A1/en unknown
- 1980-02-22 FR FR8003938A patent/FR2449690B1/en not_active Expired
- 1980-02-22 NZ NZ192949A patent/NZ192949A/en unknown
- 1980-02-22 DK DK077580A patent/DK159448C/en not_active IP Right Cessation
- 1980-02-22 CS CS801241A patent/CS226010B2/en unknown
- 1980-02-22 NO NO800501A patent/NO161000C/en unknown
- 1980-02-23 ES ES488886A patent/ES8200685A1/en not_active Expired
- 1980-10-16 ES ES495977A patent/ES495977A0/en active Granted
-
1986
- 1986-01-14 CA CA000499579A patent/CA1212665B/en not_active Expired
-
1987
- 1987-10-15 HK HK744/87A patent/HK74487A/en not_active IP Right Cessation
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