GB1442435A - Organic compounds - Google Patents
Organic compoundsInfo
- Publication number
- GB1442435A GB1442435A GB4109073A GB4109073A GB1442435A GB 1442435 A GB1442435 A GB 1442435A GB 4109073 A GB4109073 A GB 4109073A GB 4109073 A GB4109073 A GB 4109073A GB 1442435 A GB1442435 A GB 1442435A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- pentachlorophenyl
- formula
- tritylsulphenyl
- phenyl
- 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
- 150000002894 organic compounds Chemical class 0.000 title 1
- -1 Pentachlorophenyl esters Chemical class 0.000 abstract 15
- 229930186147 Cephalosporin Natural products 0.000 abstract 4
- 229930182555 Penicillin Natural products 0.000 abstract 4
- 229940124587 cephalosporin Drugs 0.000 abstract 4
- 150000001780 cephalosporins Chemical class 0.000 abstract 4
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 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 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 229940049954 penicillin Drugs 0.000 abstract 2
- 150000002960 penicillins Chemical class 0.000 abstract 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 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 2
- QXINCCWRQRSVHB-RUZDIDTESA-N (2R)-2-phenyl-2-(tritylsulfanylamino)acetic acid Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)SN[C@@H](C(=O)O)C1=CC=CC=C1 QXINCCWRQRSVHB-RUZDIDTESA-N 0.000 abstract 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- BCKIETRUJUFJJX-UHFFFAOYSA-N OS(C(C(Cl)=C(C(Cl)=C1Cl)Cl)=C1Cl)(O)=O Chemical compound OS(C(C(Cl)=C(C(Cl)=C1Cl)Cl)=C1Cl)(O)=O BCKIETRUJUFJJX-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- GDGKQKGUJGXLRX-UHFFFAOYSA-N bis(2,3,4,5,6-pentachlorophenyl) sulfite Chemical compound ClC1=C(Cl)C(Cl)=C(OS(=O)OC2=C(Cl)C(Cl)=C(Cl)C(Cl)=C2Cl)C(Cl)=C1Cl GDGKQKGUJGXLRX-UHFFFAOYSA-N 0.000 abstract 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- DZBAXVAUOBBMNC-AREMUKBSSA-N methyl (2R)-2-phenyl-2-(tritylsulfanylamino)acetate Chemical compound COC([C@H](NSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)=O DZBAXVAUOBBMNC-AREMUKBSSA-N 0.000 abstract 1
- DTHMTBUWTGVEFG-DDWIOCJRSA-N methyl (2r)-2-amino-2-phenylacetate;hydrochloride Chemical compound Cl.COC(=O)[C@H](N)C1=CC=CC=C1 DTHMTBUWTGVEFG-DDWIOCJRSA-N 0.000 abstract 1
- 125000004492 methyl ester group Chemical group 0.000 abstract 1
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 238000006049 ring expansion reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
- C07K1/062—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for alpha- or omega-carboxy functions
-
- 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
-
- 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)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT762972A AT329744B (de) | 1972-09-05 | 1972-09-05 | Verfahren zum vorubergehenden schutz von carboxylgruppen in penicillinen, penicillinsulfoxiden oder cephalosporinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1442435A true GB1442435A (en) | 1976-07-14 |
Family
ID=3597972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4109073A Expired GB1442435A (en) | 1972-09-05 | 1973-08-31 | Organic compounds |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4985091A (enExample) |
| AT (1) | AT329744B (enExample) |
| DE (1) | DE2344274A1 (enExample) |
| FR (1) | FR2334668A1 (enExample) |
| GB (1) | GB1442435A (enExample) |
| NL (1) | NL7312108A (enExample) |
| YU (1) | YU235273A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU168914B (enExample) * | 1974-07-30 | 1976-08-28 |
-
1972
- 1972-09-05 AT AT762972A patent/AT329744B/de not_active IP Right Cessation
-
1973
- 1973-08-31 GB GB4109073A patent/GB1442435A/en not_active Expired
- 1973-09-01 DE DE19732344274 patent/DE2344274A1/de active Pending
- 1973-09-03 FR FR7331685A patent/FR2334668A1/fr active Granted
- 1973-09-03 NL NL7312108A patent/NL7312108A/xx unknown
- 1973-09-04 YU YU02352/73A patent/YU235273A/xx unknown
- 1973-09-05 JP JP48100082A patent/JPS4985091A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2334668B1 (enExample) | 1978-05-12 |
| JPS4985091A (enExample) | 1974-08-15 |
| NL7312108A (enExample) | 1974-03-07 |
| FR2334668A1 (fr) | 1977-07-08 |
| YU235273A (en) | 1982-02-28 |
| ATA762972A (de) | 1975-08-15 |
| AT329744B (de) | 1976-05-25 |
| DE2344274A1 (de) | 1974-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |