GB1379465A - Cephem-4-carboxylic acids their 1-sulphoxides and methods of prepa ring them - Google Patents
Cephem-4-carboxylic acids their 1-sulphoxides and methods of prepa ring themInfo
- Publication number
- GB1379465A GB1379465A GB3214172A GB3214172A GB1379465A GB 1379465 A GB1379465 A GB 1379465A GB 3214172 A GB3214172 A GB 3214172A GB 3214172 A GB3214172 A GB 3214172A GB 1379465 A GB1379465 A GB 1379465A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cephem
- amino
- compound
- thio
- prepared
- 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
- 238000000034 method Methods 0.000 title abstract 2
- -1 hydroxy, protected hydroxy, carbamoyloxy Chemical group 0.000 abstract 19
- 150000001875 compounds Chemical class 0.000 abstract 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000006239 protecting group Chemical group 0.000 abstract 5
- 125000002252 acyl group Chemical group 0.000 abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 4
- 125000004423 acyloxy group Chemical group 0.000 abstract 3
- 125000005333 aroyloxy group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 238000006317 isomerization reaction Methods 0.000 abstract 3
- 150000003512 tertiary amines Chemical class 0.000 abstract 3
- MAFIPFSQYBWLAM-BAFYGKSASA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid Chemical class OC(=O)C1C=CS[C@@H]2CC(=O)N12 MAFIPFSQYBWLAM-BAFYGKSASA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 2
- 239000003463 adsorbent Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- WZOZEZRFJCJXNZ-IURRXHLWSA-N (6r)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]12)CC(COC(N)=O)=C(C(O)=O)N1C(=O)C2(OC)NC(=O)CC1=CC=CS1 WZOZEZRFJCJXNZ-IURRXHLWSA-N 0.000 abstract 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 abstract 1
- BGXNGARHYXNGPK-UHFFFAOYSA-N 2-[1-[(4-methoxyphenyl)methylsulfanyl]cyclohexyl]acetic acid Chemical compound C1=CC(OC)=CC=C1CSC1(CC(O)=O)CCCCC1 BGXNGARHYXNGPK-UHFFFAOYSA-N 0.000 abstract 1
- AJYXPNIENRLELY-UHFFFAOYSA-N 2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)CC1=CC=CS1 AJYXPNIENRLELY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 abstract 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical class NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- QCVZVMTWFMXZEU-UHFFFAOYSA-L calcium;dicarbamate Chemical compound [Ca+2].NC([O-])=O.NC([O-])=O QCVZVMTWFMXZEU-UHFFFAOYSA-L 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001768 cations Chemical group 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 238000000855 fermentation Methods 0.000 abstract 1
- 230000004151 fermentation Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000006000 trichloroethyl group Chemical group 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
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
-
- 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
- C07D501/60—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 3 and 4
-
- 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)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US162703A US3859282A (en) | 1971-07-14 | 1971-07-14 | Process for preparing 3-substituted methyl-7-acylamido-7-methoxy-2-cephem-4-carboxylic acid and its esters |
| US17955971A | 1971-09-10 | 1971-09-10 | |
| US20121071A | 1971-11-22 | 1971-11-22 | |
| US24427072A | 1972-04-14 | 1972-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1379465A true GB1379465A (en) | 1975-01-02 |
Family
ID=27496523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3214172A Expired GB1379465A (en) | 1971-07-14 | 1972-07-10 | Cephem-4-carboxylic acids their 1-sulphoxides and methods of prepa ring them |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU464944B2 (en:Method) |
| BE (1) | BE785917A (en:Method) |
| CA (1) | CA1014949A (en:Method) |
| CH (1) | CH583739A5 (en:Method) |
| DD (2) | DD105452A5 (en:Method) |
| DE (1) | DE2234479C3 (en:Method) |
| FR (2) | FR2154425B1 (en:Method) |
| GB (1) | GB1379465A (en:Method) |
| NL (1) | NL7208855A (en:Method) |
-
0
- BE BE785917D patent/BE785917A/xx unknown
-
1972
- 1972-06-27 CA CA145,854A patent/CA1014949A/en not_active Expired
- 1972-06-27 NL NL7208855A patent/NL7208855A/xx not_active Application Discontinuation
- 1972-07-04 AU AU44207/72A patent/AU464944B2/en not_active Expired
- 1972-07-10 GB GB3214172A patent/GB1379465A/en not_active Expired
- 1972-07-12 DD DD164376A patent/DD105452A5/xx unknown
- 1972-07-12 FR FR7225251A patent/FR2154425B1/fr not_active Expired
- 1972-07-12 DD DD174534*A patent/DD108542A5/xx unknown
- 1972-07-13 DE DE2234479A patent/DE2234479C3/de not_active Expired
- 1972-07-13 CH CH1054472A patent/CH583739A5/xx not_active IP Right Cessation
- 1972-12-08 FR FR7243745A patent/FR2162237B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2234479C3 (de) | 1976-01-02 |
| AU4420772A (en) | 1974-01-10 |
| CH583739A5 (en:Method) | 1977-01-14 |
| NL7208855A (en:Method) | 1973-01-16 |
| FR2154425B1 (en:Method) | 1973-12-07 |
| DE2234479B2 (de) | 1975-05-22 |
| DE2234479A1 (de) | 1973-02-15 |
| CA1014949A (en) | 1977-08-02 |
| AU464944B2 (en) | 1975-09-11 |
| BE785917A (fr) | 1973-01-08 |
| DD105452A5 (en:Method) | 1974-04-20 |
| DD108542A5 (en:Method) | 1974-09-20 |
| FR2154425A1 (en:Method) | 1973-05-11 |
| FR2162237B1 (en:Method) | 1974-03-15 |
| FR2162237A1 (en:Method) | 1973-07-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 48S | Specification amended (sect. 8/1949) | ||
| SPA | Amended specification published | ||
| PCNP | Patent ceased through non-payment of renewal fee |