GB1144191A - Esters of 6-aminopenicillanic acid - Google Patents
Esters of 6-aminopenicillanic acidInfo
- Publication number
- GB1144191A GB1144191A GB1694/66A GB169466A GB1144191A GB 1144191 A GB1144191 A GB 1144191A GB 1694/66 A GB1694/66 A GB 1694/66A GB 169466 A GB169466 A GB 169466A GB 1144191 A GB1144191 A GB 1144191A
- Authority
- GB
- United Kingdom
- Prior art keywords
- esters
- aminopenicillanate
- tri
- aminopenicillanic acid
- sno
- 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
- 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 title abstract 5
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 title abstract 4
- 150000002148 esters Chemical class 0.000 title abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 229930182555 Penicillin Natural products 0.000 abstract 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 239000011591 potassium Substances 0.000 abstract 2
- -1 tri-phenylstannyl 6-aminopenicillanate Chemical compound 0.000 abstract 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2224—Compounds having one or more tin-oxygen linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,144,191. Stannyl esters of 6-aminopenicillanic acid. ASTRA A.B. 12 Jan., 1967 [13 Jan., 1966], No. 1694/66. Heading C2A. The invention comprises esters of 6-amino penicillanic acid of formula wherein each of the groups R, which may be the same or different, represent a monovalent hydrocarbon group, e.g. alkyl, aryl or aralkyl and especially n-propyl, n-butyl or phenyl. The compounds are prepared by reacting 6-aminopenicillanic acid with a compound of formula XSnR 3 , wherein R is as defined above and X is C 1-6 alkoxy, C 1-6 thioalkyl, di-C 1-6 alkylamino or hydroxy or R 3 SnO-, wherein R is as defined above. Where X is OH or R 3 SnO-, the reaction is carried out in an organic solvent, e.g. benzene, and the water produced is removed by distillation as it is formed. Where X is alkoxy &c., the reaction is in an organic solvent, such as ethyl acetate, at 60-130‹ C. Typical esters are the tri-n-butylatannyl 6- aminopenicillanate, tri-phenylstannyl 6-aminopenicillanate and tri-n-propylstannyl 6-aminopenicillanate. Penicillins are produced by acylation and removal of the ester grouping, e.g. with potassium thiophenylate in dimethyl formamide, to produce the potassium penicillin.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1694/66A GB1144191A (en) | 1966-01-13 | 1966-01-13 | Esters of 6-aminopenicillanic acid |
| DE1966A0054374 DE1645949C3 (en) | 1966-01-13 | 1966-12-15 | 6-AMINOPENICILLANIC ACID ESTERS AND PROCESS FOR THE PREPARATION |
| CH1798966A CH498869A (en) | 1966-01-13 | 1966-12-16 | 6-amino-penicillanic acid esters |
| AT1176466A AT268524B (en) | 1966-01-13 | 1966-12-22 | Process for the production of new 6 aminopenicillanic acid esters |
| SE00208/67A SE336793B (en) | 1966-01-13 | 1967-01-04 | |
| FI670028A FI48097C (en) | 1966-01-13 | 1967-01-05 | Trialkyltin or triphenyltin esters of 6-aminopenicillanic acid, usable as intermediates in the preparation of penicillins |
| NO166271A NO134056C (en) | 1966-01-13 | 1967-01-05 | |
| DK15367*#A DK131501C (en) | 1966-01-13 | 1967-01-11 | ESTERS OF 6-AMINOPENICILLANIC ACID FOR USE AS AN INTERMEDIATE PREPARATION OF PENICILLINES |
| FR90932A FR1507866A (en) | 1966-01-13 | 1967-01-12 | New class of esters of 6-aminopenicillanic acid and process for their preparation |
| NL6700598A NL149500C (en) | 1966-01-13 | 1967-01-13 | PROCEDURE FOR PREPARING A 6-AMINOPENICILLAN ACID ESTER. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1694/66A GB1144191A (en) | 1966-01-13 | 1966-01-13 | Esters of 6-aminopenicillanic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1144191A true GB1144191A (en) | 1969-03-05 |
Family
ID=9726388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1694/66A Expired GB1144191A (en) | 1966-01-13 | 1966-01-13 | Esters of 6-aminopenicillanic acid |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT268524B (en) |
| CH (1) | CH498869A (en) |
| DE (1) | DE1645949C3 (en) |
| DK (1) | DK131501C (en) |
| FI (1) | FI48097C (en) |
| FR (1) | FR1507866A (en) |
| GB (1) | GB1144191A (en) |
| NL (1) | NL149500C (en) |
| NO (1) | NO134056C (en) |
| SE (1) | SE336793B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5017477B1 (en) * | 1970-02-21 | 1975-06-20 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1317566A (en) * | 1963-05-08 | |||
| AT229489B (en) * | 1961-03-22 | 1963-09-25 | Gruenenthal Chemie | Process for the preparation of new derivatives of 6-aminopenicillanic acid |
| GB1122306A (en) * | 1965-07-08 | 1968-08-07 | Beecham Group Ltd | Improvements in or relating to penicillin derivatives |
| DE1645972A1 (en) * | 1966-06-03 | 1970-10-01 | Astra Ab | Process for making antimicrobial compounds |
-
1966
- 1966-01-13 GB GB1694/66A patent/GB1144191A/en not_active Expired
- 1966-12-15 DE DE1966A0054374 patent/DE1645949C3/en not_active Expired
- 1966-12-16 CH CH1798966A patent/CH498869A/en not_active IP Right Cessation
- 1966-12-22 AT AT1176466A patent/AT268524B/en active
-
1967
- 1967-01-04 SE SE00208/67A patent/SE336793B/xx unknown
- 1967-01-05 NO NO166271A patent/NO134056C/no unknown
- 1967-01-05 FI FI670028A patent/FI48097C/en active
- 1967-01-11 DK DK15367*#A patent/DK131501C/en active
- 1967-01-12 FR FR90932A patent/FR1507866A/en not_active Expired
- 1967-01-13 NL NL6700598A patent/NL149500C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NL149500C (en) | 1976-10-15 |
| DK131501B (en) | 1975-07-28 |
| NL149500B (en) | 1976-05-17 |
| DE1645949A1 (en) | 1970-07-16 |
| FI48097B (en) | 1974-02-28 |
| DE1645949B2 (en) | 1977-02-10 |
| DK131501C (en) | 1976-01-12 |
| CH498869A (en) | 1970-11-15 |
| AT268524B (en) | 1969-02-10 |
| NL6700598A (en) | 1967-07-14 |
| SE336793B (en) | 1971-07-19 |
| FI48097C (en) | 1974-06-10 |
| FR1507866A (en) | 1967-12-29 |
| NO134056C (en) | 1976-08-11 |
| NO134056B (en) | 1976-05-03 |
| DE1645949C3 (en) | 1977-09-22 |
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