GB1339007A - Antibiotics and processes for their production - Google Patents
Antibiotics and processes for their productionInfo
- Publication number
- GB1339007A GB1339007A GB2915770A GB1339007DA GB1339007A GB 1339007 A GB1339007 A GB 1339007A GB 2915770 A GB2915770 A GB 2915770A GB 1339007D A GB1339007D A GB 1339007DA GB 1339007 A GB1339007 A GB 1339007A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- radical
- ester
- azido
- give
- 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
- 238000000034 method Methods 0.000 title abstract 4
- 239000003242 anti bacterial agent Substances 0.000 title 1
- 229940088710 antibiotic agent Drugs 0.000 title 1
- -1 methoxy, ethoxy, methyl Chemical group 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 6
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 5
- 150000002148 esters Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 150000002960 penicillins Chemical class 0.000 abstract 3
- 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 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000008049 diazo compounds Chemical class 0.000 abstract 2
- WYRSGXAIHNMKOL-UHFFFAOYSA-N $l^{1}-sulfanylethane Chemical compound CC[S] WYRSGXAIHNMKOL-UHFFFAOYSA-N 0.000 abstract 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 238000007098 aminolysis reaction Methods 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000006698 hydrazinolysis reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 abstract 1
- 239000012434 nucleophilic reagent Substances 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 abstract 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 abstract 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/72—Acyl halides containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/64—Acyl halides
- C07C57/76—Acyl halides containing halogen outside the carbonyl halide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1339007 6-Disubstituted penicillins MERCK & CO Inc 30 April 1971 [16 June 1970] 29157/70 Heading C2A The invention relates to novel penicillin compounds having the general Formula I and the corresponding 1-sulphoxides, in which R 1 is a hydroxy or mercapto radical, a substituted or unsubstituted methoxy, ethoxy, methyl, ethyl, methylthio or ethylthio radical, a carbamoyloxy, carbamoylthio, C 1-6 alkanoyloxy, C 1-6 alkanoylthio, cyano, carboxy or substituted carboxy (e.g. carbamoyl) radical and Q is an azido, amino or acylamino radical; or R 1 is halogen and Q is azido; and R is an esterifying radical or, when Q is acylamino, is a hydrogen atom, a cation or an esterifying radical. The compounds are prepared by either (i) diazotizing the amino group of a 6-aminopenicillanic acid (6-APA) ester to give a compound of Formula IT wherein R is an esterifying group, the 1-sulphoxides of these compounds (II) being novel and forming part of the invention, and then subjecting the compound (II) to one or more of the reactions described below; or (ii) reacting a 6-APA ester with an aromatic aldehyde having at least one o- or p-electronegative substituent (e.g. NO 2 , CN alkoxycarbonyl, carbamoyl, or methylsulphonyl) to give an imine derivative of the 6-APA ester, reacting this derivative with a compound which introduces the group R 1 (as defined above) and subjecting the product to aminolysis or hydrazinolysis to give a 6-R 1 -6- amino penicillanic acid, the procedure (ii) being illustrated by the following reaction scheme in which R 8 is an esterifying group. In procedure (i) the diazo compound II is formed by a conventional diazotizing procedure. If the 1-sulphoxide is desired, the 6-APA ester may be subjected to a preliminary S-oxidation step e.g. with m-chloroperbenzoic acid. The diazo compound may then be reacted with: (a) a halo-azide (or another azide together with a source of positive halogen such as a bromoacylimide or -amide) to give the corresponding 6-halo-6-azido penicillanic ester which may be subsequently reacted with a nucleophilic reagent capable of replacing the halogen by R 1 ; the latter compound may optionally be subjected to reduction to convert the -N 3 group to -NH 2 , and this amino group may then be acylated; (b) trimethyl- or triethylboron followed by a halo-azide to produce the 6-methyl or -ethyl-6- azido compound; (c) trifluoromethyl iodide, with irradiation and in the presence of a trialkylammonium azide to give the 6-CF 3 -6-azido penicillanic ester. The penicillin compounds (I) have antibacterial activity and may be mixed with a carrier or diluent and made up into pharmaceutical compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2915770 | 1970-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1339007A true GB1339007A (en) | 1973-11-28 |
Family
ID=10287044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2915770A Expired GB1339007A (en) | 1970-06-16 | 1971-04-30 | Antibiotics and processes for their production |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5715117B1 (en) |
| AR (1) | AR205683A1 (en) |
| AT (3) | AT311550B (en) |
| BE (1) | BE768529A (en) |
| CA (1) | CA983478A (en) |
| CH (1) | CH579572A5 (en) |
| CS (1) | CS190359B2 (en) |
| DE (2) | DE2151036C2 (en) |
| DK (1) | DK133301C (en) |
| DO (1) | DOP1972001821A (en) |
| EG (1) | EG10970A (en) |
| FI (1) | FI57418C (en) |
| FR (1) | FR2100768B1 (en) |
| GB (1) | GB1339007A (en) |
| HU (2) | HU168077B (en) |
| IE (1) | IE35370B1 (en) |
| IL (1) | IL36990A (en) |
| IT (1) | IT1057857B (en) |
| LU (1) | LU63344A1 (en) |
| NL (1) | NL178876C (en) |
| PH (1) | PH10995A (en) |
| RO (3) | RO58734A (en) |
| SE (2) | SE391525B (en) |
| SU (2) | SU460629A3 (en) |
| ZA (1) | ZA713228B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2600842A1 (en) * | 1975-01-17 | 1976-07-22 | Beecham Group Ltd | NEW PENICILLIN DERIVATIVES, THE METHOD FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| US4308259A (en) | 1979-03-01 | 1981-12-29 | Beecham Group Limited | Penicillin derivatives |
| US4501696A (en) * | 1981-07-10 | 1985-02-26 | Beecham Group P.L.C. | Process for the preparation of penam derivatives |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2199454A2 (en) * | 1972-09-15 | 1974-04-12 | Merck & Co Inc | 6-Beta-acyl amino penicillanic acids - antibiotics prepared by acylating a 6-alpha-substd -6-beta-amino penicillanic acid |
| CA1040620A (en) * | 1972-11-14 | 1978-10-17 | Frank J. Urban | 6-alkoxy-6-acylamidopenicillins 7-alkoxy-7-acylamido acetoxycephalosporins and process |
| EP0071395B1 (en) * | 1981-07-25 | 1988-08-10 | Beecham Group Plc | Beta-lactam antibacterial agents |
-
1971
- 1971-01-01 AR AR236154A patent/AR205683A1/en active
- 1971-04-30 GB GB2915770A patent/GB1339007A/en not_active Expired
- 1971-05-18 ZA ZA713228A patent/ZA713228B/en unknown
- 1971-06-07 IL IL36990A patent/IL36990A/en unknown
- 1971-06-08 CA CA115,149A patent/CA983478A/en not_active Expired
- 1971-06-08 CS CS714190A patent/CS190359B2/en unknown
- 1971-06-09 PH PH12530A patent/PH10995A/en unknown
- 1971-06-09 HU HUME1667A patent/HU168077B/hu unknown
- 1971-06-09 SE SE7107459A patent/SE391525B/en unknown
- 1971-06-14 AT AT511671A patent/AT311550B/en not_active IP Right Cessation
- 1971-06-14 AT AT279473A patent/AT320860B/en not_active IP Right Cessation
- 1971-06-14 AT AT279373*1A patent/AT322738B/en not_active IP Right Cessation
- 1971-06-15 SU SU1673668A patent/SU460629A3/en active
- 1971-06-15 EG EG258/71A patent/EG10970A/en active
- 1971-06-15 RO RO70721A patent/RO58734A/ro unknown
- 1971-06-15 DK DK291971A patent/DK133301C/en not_active IP Right Cessation
- 1971-06-15 DE DE2151036A patent/DE2151036C2/en not_active Expired
- 1971-06-15 IE IE771/71A patent/IE35370B1/en unknown
- 1971-06-15 IT IT7151041A patent/IT1057857B/en active
- 1971-06-15 FI FI1674/71A patent/FI57418C/en active
- 1971-06-15 RO RO67309A patent/RO61560A/ro unknown
- 1971-06-15 RO RO70720A patent/RO58733A/ro unknown
- 1971-06-15 BE BE768529A patent/BE768529A/xx not_active IP Right Cessation
- 1971-06-15 DE DE2129637A patent/DE2129637C2/en not_active Expired
- 1971-06-15 CH CH875271A patent/CH579572A5/xx not_active IP Right Cessation
- 1971-06-16 LU LU63344D patent/LU63344A1/xx unknown
- 1971-06-16 NL NLAANVRAGE7108283,A patent/NL178876C/en not_active IP Right Cessation
- 1971-06-16 FR FR7121921A patent/FR2100768B1/fr not_active Expired
- 1971-06-16 JP JP4323171A patent/JPS5715117B1/ja active Pending
-
1972
- 1972-08-23 DO DO1972001821A patent/DOP1972001821A/en unknown
- 1972-11-01 SU SU721843439A patent/SU584786A3/en active
-
1973
- 1973-01-04 HU HUME1377A patent/HU167333B/hu unknown
-
1974
- 1974-04-10 SE SE7404874A patent/SE7404874L/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2600842A1 (en) * | 1975-01-17 | 1976-07-22 | Beecham Group Ltd | NEW PENICILLIN DERIVATIVES, THE METHOD FOR THEIR MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| US4048320A (en) * | 1975-01-17 | 1977-09-13 | Beecham Group Limited | Penicillins |
| DK154888B (en) * | 1975-01-17 | 1989-01-02 | Beecham Group Ltd | ANALOGY PROCEDURE FOR PREPARING 6-SUBSTITUTED-6-METHOXYPENICILLANIC ACID DERIVATIVES |
| US4308259A (en) | 1979-03-01 | 1981-12-29 | Beecham Group Limited | Penicillin derivatives |
| US4501696A (en) * | 1981-07-10 | 1985-02-26 | Beecham Group P.L.C. | Process for the preparation of penam derivatives |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |