GB1204394A - Process for converting a penicillin sulfoxide ester to a cephalosporin antibiotic - Google Patents
Process for converting a penicillin sulfoxide ester to a cephalosporin antibioticInfo
- Publication number
- GB1204394A GB1204394A GB21833/68A GB2183368A GB1204394A GB 1204394 A GB1204394 A GB 1204394A GB 21833/68 A GB21833/68 A GB 21833/68A GB 2183368 A GB2183368 A GB 2183368A GB 1204394 A GB1204394 A GB 1204394A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- sulphonamide
- alkyl
- ester
- tertiary
- 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
- -1 penicillin sulfoxide ester Chemical class 0.000 title abstract 5
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 230000003115 biocidal effect Effects 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 229930182555 Penicillin Natural products 0.000 abstract 4
- 229940049954 penicillin Drugs 0.000 abstract 4
- 229940124530 sulfonamide Drugs 0.000 abstract 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000000565 sulfonamide group Chemical group 0.000 abstract 3
- 125000003944 tolyl group Chemical group 0.000 abstract 3
- 125000005023 xylyl group Chemical group 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- JGSARLDLIJGVTE-ORHYLEIMSA-N (5r)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H]2SC(C(N2C1=O)C(O)=O)(C)C)NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-ORHYLEIMSA-N 0.000 abstract 1
- CIPQGGYPCPIDBB-WPZCJLIBSA-N (6r)-3-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)C)C(O)=O)NC(=O)CC1=CC=CC=C1 CIPQGGYPCPIDBB-WPZCJLIBSA-N 0.000 abstract 1
- OFHXXQISSLUHJI-UHFFFAOYSA-N 1-propylsulfonylpyrrolidine Chemical compound CCCS(=O)(=O)N1CCCC1 OFHXXQISSLUHJI-UHFFFAOYSA-N 0.000 abstract 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract 1
- GGUJLVPQFOPIJU-UHFFFAOYSA-N 2-methyl-1,2-thiazolidine 1,1-dioxide Chemical compound CN1CCCS1(=O)=O GGUJLVPQFOPIJU-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
- LRXKXDGJVHZGBH-UHFFFAOYSA-N 4-(benzenesulfonyl)morpholine Chemical compound C=1C=CC=CC=1S(=O)(=O)N1CCOCC1 LRXKXDGJVHZGBH-UHFFFAOYSA-N 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 abstract 1
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- WCFDSGHAIGTEKL-UHFFFAOYSA-N n,n-dimethylmethanesulfonamide Chemical compound CN(C)S(C)(=O)=O WCFDSGHAIGTEKL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 150000003456 sulfonamides Chemical group 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,204,394. Cephalosporins. ELI LILLY & CO. 8 May, 1968 [8 May, 1967], No. 21833/68. Heading C2A. A penicillin sulphoxide ester is converted to a desacetoxy-cephalosporin antibiotic by heating the penicillin sulphoxide ester dissolved in a tertiary sulphonamide under acid conditions at 80 to 175 C., the tertiary sulphonamide having the formula wherein (a) each of R 1 , R 2 and R 3 is C 1 to C 10 alkyl, phenyl, tolyl, or xylyl, at least one of R 1 , R 2 and R 3 is C 1 to C 10 alkyl, and R 1 , R 2 and R 3 together contain not more than 18 carbon atoms; (b) R 1 is a C 1 to C 10 alkyl, phenyl, tolyl or xylyl, and R 2 and R 3 are taken together with the N atom to which they are bonded to complete a monocyclic ring radical bonded to the S atom, which radical contains from 4 to 6 saturated carbon atoms, and which radical can contain a ring member oxygen atom gamma to the ring N, such that R 1 , R 2 and R 3 together contain up to 12 carbon atoms; (c) R 1 and R 2 are taken together with the sulphonamide grouping to which they are bonded to form a sulphur oxide and mononitrogen monocyclic ring having 3 to 5 saturated ring carbon atoms therein, and R 3 is alkyl, phenyl, tolyl or xylyl such that R 1 , R 2 and R 3 together contain up to about 12 carbon atoms, and/or (d) R 1 is -NR 4 R 5 and each R 2 , R 3 , R 4 and R 5 is alkyl such that the sulphondiamide formed thereby contains up to about 12 carbon atoms. Typical tertiary sulphonamides are N,N-dimethylmethane sulphonamide, N-(propylsulphonyl)-pyrrolidine, N-(phenylsulphonyl) -morpholine, 2 - methyl - isothiazolidine - 1,1 - dioxide and tetramethyl sulphondiamide. The penicillin sulphoxide ester is dissolved in the tertiary sulphonamide and the acid substance added thereto. Preferred acid substances are acetic anhydride and aluminium chloride. Others are disclosed in U.S.A. Specification 3,275,626. Any penicillin sulphoxide ester may be used to form the corresponding desacetoxycephalosporins, e.g. 6-(phenylacetamido)-2,2- dimethylpenam-3-carboxylic acid yields 7-(phenylacetamido) - 3 - methyl - 3 - cephem - 4 - carboxylic acid; 6-(thiophene-2-acetamido)- 2,2 - dimethylpenam - 3 - carboxylic acid yields 7 - (thiophene - 2 - acetamido) - 3 - methyl - 3 - cephem-4-carboxylic acid. 2,2,2 - Trichloroethyl 6-(phenylacetamido)- penicillanate sulphoxide is prepared by reacting potassium benzyl penicillinate with 2,2,2-trichloroethanol in a solvent in the presence of a base and condensing agent and treating the ester so formed with m-chloroperbenzoic acid in chloroform.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63662967A | 1967-05-08 | 1967-05-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1204394A true GB1204394A (en) | 1970-09-09 |
Family
ID=24552693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21833/68A Expired GB1204394A (en) | 1967-05-08 | 1968-05-08 | Process for converting a penicillin sulfoxide ester to a cephalosporin antibiotic |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS4920318B1 (en) |
| BE (1) | BE714747A (en) |
| CH (1) | CH540292A (en) |
| CY (1) | CY705A (en) |
| DE (1) | DE1770360C3 (en) |
| DK (1) | DK140101B (en) |
| FR (1) | FR1561048A (en) |
| GB (1) | GB1204394A (en) |
| IL (1) | IL29948A (en) |
| MY (1) | MY7300489A (en) |
| NL (1) | NL6806533A (en) |
| SE (1) | SE357750B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116332817A (en) * | 2022-11-16 | 2023-06-27 | 桂林理工大学 | A kind of synthetic method of N-sulfonyl sulfoximine derivative |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4767851A (en) * | 1984-07-16 | 1988-08-30 | Gema, S.A. | Process for the preparation of 7-amino and 7-substituted amino-desacetoxycephalosporins |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275626A (en) * | 1962-07-31 | 1966-09-27 | Lilly Co Eli | Penicillin conversion via sulfoxide |
-
1968
- 1968-05-07 FR FR1561048D patent/FR1561048A/fr not_active Expired
- 1968-05-07 BE BE714747D patent/BE714747A/xx not_active IP Right Cessation
- 1968-05-07 SE SE06143/68A patent/SE357750B/xx unknown
- 1968-05-07 IL IL29948A patent/IL29948A/en unknown
- 1968-05-07 DK DK210468AA patent/DK140101B/en not_active IP Right Cessation
- 1968-05-08 NL NL6806533A patent/NL6806533A/xx unknown
- 1968-05-08 JP JP43030825A patent/JPS4920318B1/ja active Pending
- 1968-05-08 DE DE1770360A patent/DE1770360C3/en not_active Expired
- 1968-05-08 CH CH683968A patent/CH540292A/en not_active IP Right Cessation
- 1968-05-08 GB GB21833/68A patent/GB1204394A/en not_active Expired
-
1973
- 1973-10-01 CY CY70573A patent/CY705A/en unknown
- 1973-12-30 MY MY489/73A patent/MY7300489A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116332817A (en) * | 2022-11-16 | 2023-06-27 | 桂林理工大学 | A kind of synthetic method of N-sulfonyl sulfoximine derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770360C3 (en) | 1975-06-12 |
| DK140101B (en) | 1979-06-18 |
| NL6806533A (en) | 1968-11-11 |
| CY705A (en) | 1973-10-01 |
| SE357750B (en) | 1973-07-09 |
| MY7300489A (en) | 1973-12-31 |
| DE1770360B2 (en) | 1974-10-24 |
| DK140101C (en) | 1979-11-12 |
| CH540292A (en) | 1973-08-15 |
| BE714747A (en) | 1968-11-07 |
| IL29948A (en) | 1971-08-25 |
| DE1770360A1 (en) | 1971-10-21 |
| FR1561048A (en) | 1969-03-21 |
| IL29948A0 (en) | 1968-07-25 |
| JPS4920318B1 (en) | 1974-05-23 |
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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 |