GB1153421A - Cephalosporin Derivatives - Google Patents
Cephalosporin DerivativesInfo
- Publication number
- GB1153421A GB1153421A GB4718364A GB4718364A GB1153421A GB 1153421 A GB1153421 A GB 1153421A GB 4718364 A GB4718364 A GB 4718364A GB 4718364 A GB4718364 A GB 4718364A GB 1153421 A GB1153421 A GB 1153421A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkylthio
- prepared
- acid
- compound
- chloride
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 3
- 229940124587 cephalosporin Drugs 0.000 title abstract 3
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- -1 halogenophenyl Chemical group 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 2
- HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001336 alkenes Chemical group 0.000 abstract 2
- 125000004450 alkenylene group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 150000001540 azides Chemical class 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- YIOUOZKPXQCYOY-UHFFFAOYSA-N 2-[4-(tritylamino)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1NC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 YIOUOZKPXQCYOY-UHFFFAOYSA-N 0.000 abstract 1
- WMFATTFQNRPXBQ-UHFFFAOYSA-N 2-bromopentanoic acid Chemical compound CCCC(Br)C(O)=O WMFATTFQNRPXBQ-UHFFFAOYSA-N 0.000 abstract 1
- IUBCTUXJYXUSAZ-UHFFFAOYSA-N 2-methylpentanethioic s-acid Chemical compound CCCC(C)C(S)=O IUBCTUXJYXUSAZ-UHFFFAOYSA-N 0.000 abstract 1
- ZYCMCQISZLRQPK-UHFFFAOYSA-N 2-methylsulfanylpentanoyl chloride Chemical compound CSC(C(=O)Cl)CCC ZYCMCQISZLRQPK-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N alpha-mercaptoacetic acid Natural products OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005366 cycloalkylthio group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- CFNDVXUTYPXOPG-UHFFFAOYSA-N ethyl 2-(4-aminophenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(N)C=C1 CFNDVXUTYPXOPG-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229940124531 pharmaceutical excipient Drugs 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4718364A GB1153421A (en) | 1961-05-16 | 1965-05-19 | Cephalosporin Derivatives |
| FR62027A FR91256E (fr) | 1965-05-19 | 1966-05-18 | Nouveaux dérivés de la céphalosporine c et leurs procédés de préparation |
| FR62022A FR183F (fr) | 1961-05-16 | 1966-05-18 | Médicament anti-bactérien et antibiotique a base de dérivés de la céphalosporine c. |
| NL6606820A NL6606820A (enrdf_load_stackoverflow) | 1961-05-16 | 1966-05-18 | |
| BE681245D BE681245A (enrdf_load_stackoverflow) | 1961-05-16 | 1966-05-18 | |
| AT474166A AT271721B (de) | 1961-05-16 | 1966-05-18 | Verfahren zur Herstellung neuer Derivate der 7-Aminocephalosporansäure |
| DE19661695074 DE1695074A1 (de) | 1961-05-16 | 1966-05-20 | Verfahren zur Herstellung von Antibiotika |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17845/61A GB1012943A (en) | 1961-05-16 | 1961-05-16 | Improvements in or relating to antibiotics |
| GB302662 | 1962-01-26 | ||
| GB4718364A GB1153421A (en) | 1961-05-16 | 1965-05-19 | Cephalosporin Derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1153421A true GB1153421A (en) | 1969-05-29 |
Family
ID=10444053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4718364A Expired GB1153421A (en) | 1961-05-16 | 1965-05-19 | Cephalosporin Derivatives |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT271721B (enrdf_load_stackoverflow) |
| BE (1) | BE681245A (enrdf_load_stackoverflow) |
| DE (1) | DE1695074A1 (enrdf_load_stackoverflow) |
| FR (1) | FR183F (enrdf_load_stackoverflow) |
| GB (1) | GB1153421A (enrdf_load_stackoverflow) |
| NL (1) | NL6606820A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5024289A (enrdf_load_stackoverflow) * | 1973-06-29 | 1975-03-15 |
-
1965
- 1965-05-19 GB GB4718364A patent/GB1153421A/en not_active Expired
-
1966
- 1966-05-18 NL NL6606820A patent/NL6606820A/xx unknown
- 1966-05-18 AT AT474166A patent/AT271721B/de active
- 1966-05-18 FR FR62022A patent/FR183F/fr not_active Expired
- 1966-05-18 BE BE681245D patent/BE681245A/xx unknown
- 1966-05-20 DE DE19661695074 patent/DE1695074A1/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5024289A (enrdf_load_stackoverflow) * | 1973-06-29 | 1975-03-15 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE681245A (enrdf_load_stackoverflow) | 1966-11-18 |
| DE1695074A1 (de) | 1972-08-10 |
| AT271721B (de) | 1969-06-10 |
| FR183F (fr) | 1967-12-26 |
| NL6606820A (enrdf_load_stackoverflow) | 1966-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| PE | Patent expired |