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)
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 (https=) |
| BE (1) | BE714747A (https=) |
| CH (1) | CH540292A (https=) |
| CY (1) | CY705A (https=) |
| DE (1) | DE1770360C3 (https=) |
| DK (1) | DK140101B (https=) |
| FR (1) | FR1561048A (https=) |
| GB (1) | GB1204394A (https=) |
| IL (1) | IL29948A (https=) |
| MY (1) | MY7300489A (https=) |
| NL (1) | NL6806533A (https=) |
| SE (1) | SE357750B (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116332817A (zh) * | 2022-11-16 | 2023-06-27 | 桂林理工大学 | 一种n-磺酰基亚砜亚胺衍生物的合成方法 |
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 SE SE06143/68A patent/SE357750B/xx unknown
- 1968-05-07 BE BE714747D patent/BE714747A/xx not_active IP Right Cessation
- 1968-05-07 IL IL29948A patent/IL29948A/en unknown
- 1968-05-07 DK DK210468AA patent/DK140101B/da not_active IP Right Cessation
- 1968-05-08 DE DE1770360A patent/DE1770360C3/de not_active Expired
- 1968-05-08 NL NL6806533A patent/NL6806533A/xx unknown
- 1968-05-08 GB GB21833/68A patent/GB1204394A/en not_active Expired
- 1968-05-08 JP JP43030825A patent/JPS4920318B1/ja active Pending
- 1968-05-08 CH CH683968A patent/CH540292A/de not_active IP Right Cessation
-
1973
- 1973-10-01 CY CY70573A patent/CY705A/xx unknown
- 1973-12-30 MY MY489/73A patent/MY7300489A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116332817A (zh) * | 2022-11-16 | 2023-06-27 | 桂林理工大学 | 一种n-磺酰基亚砜亚胺衍生物的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4920318B1 (https=) | 1974-05-23 |
| DK140101C (https=) | 1979-11-12 |
| DE1770360A1 (de) | 1971-10-21 |
| SE357750B (https=) | 1973-07-09 |
| MY7300489A (en) | 1973-12-31 |
| CY705A (en) | 1973-10-01 |
| NL6806533A (https=) | 1968-11-11 |
| BE714747A (https=) | 1968-11-07 |
| IL29948A0 (en) | 1968-07-25 |
| FR1561048A (https=) | 1969-03-21 |
| DE1770360B2 (de) | 1974-10-24 |
| DE1770360C3 (de) | 1975-06-12 |
| CH540292A (de) | 1973-08-15 |
| DK140101B (da) | 1979-06-18 |
| IL29948A (en) | 1971-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE8305916L (sv) | Mellanprodukter for framstellning av penicillansyra-1,1-dioxider | |
| GB1470188A (en) | Penicillins | |
| ES467601A1 (es) | Procedimiento para la preparacion de derivados de cefem. | |
| SE7611047L (sv) | Forfarande for framstellning av antibakteriella emnen | |
| ATE18403T1 (de) | Antibiotische cephalosporinverbindungen. | |
| GB1204394A (en) | Process for converting a penicillin sulfoxide ester to a cephalosporin antibiotic | |
| SE7702668L (sv) | Nya stilbenforeningar och forfarande for deras framstellning | |
| HUT37623A (en) | Process for production of derivatives of new cefem-carbonic acid and medical preparatives containing such compounds | |
| GB1497039A (en) | Penicillins and cephalosporins | |
| GB1493197A (en) | Amides of clavulanic acid | |
| GB1346744A (en) | Betalactam compounds and process for preparing same | |
| OA07495A (fr) | Nouveaux dérivés de céphalosporines, leur procédé de préparation et médicaments antibiotiques contenant lesdits dérivés | |
| GB1442993A (en) | Penicillin and cephalosporin r-sulphoxides | |
| GB1442302A (en) | Penicillin and cephalosporin derivatives | |
| GB1421280A (en) | 3-heterocyclicthiomethylcephalosporins | |
| GB894460A (en) | Improvements in or relating to penicillins | |
| DE3171431D1 (en) | Derivatives of 7-beta-(ketoximinoacylamido)-ceph-3-em-4-carboxylic acids, process for their preparation and their pharmaceutical compositions containing them | |
| GB1344707A (en) | Cephalosporins via penicillin sulphoxide conversion | |
| DE3374783D1 (en) | Beta-lactam antibiotics, process for their preparation and preparations containing them | |
| GB1395214A (en) | Thiazolinyl and thiazinyl derivatives of benzimidazoles | |
| ES423024A1 (es) | Procedimiento para la preparacion de derivados de acidos penicilanico y cefalosporanico. | |
| ATE12644T1 (de) | Verfahren zur herstellung von 7-acylamino-3-(thio substituierte)methyl-3-cephem-4-carboxylsaeure-1 oxyd-verbindungen. | |
| GB2014574A (en) | Lactam Compounds | |
| GB1355487A (en) | 7- -3,5,7-triaza-1-azonia-1-adamantyl- acetamido-cephalosporanic acid haldies and sulphonates | |
| GB960896A (en) | Production of penicillins |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |