ES419927A2 - Cephalosporin derivatives - Google Patents
Cephalosporin derivativesInfo
- Publication number
- ES419927A2 ES419927A2 ES419927A ES419927A ES419927A2 ES 419927 A2 ES419927 A2 ES 419927A2 ES 419927 A ES419927 A ES 419927A ES 419927 A ES419927 A ES 419927A ES 419927 A2 ES419927 A2 ES 419927A2
- Authority
- ES
- Spain
- Prior art keywords
- acylamido
- group
- cef
- butoxyimino
- formula
- 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 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- -1 benzo [b] furan-2-yl Chemical group 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 125000002541 furyl group Chemical group 0.000 abstract 3
- 125000001544 thienyl group Chemical group 0.000 abstract 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000005605 benzo group Chemical group 0.000 abstract 2
- 230000000903 blocking effect Effects 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 238000000926 separation method Methods 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
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Improvements introduced in the object of the main patent No. 402,651 applied for on May 12, 1972 for: "Procedure for the preparation of cephalosporin derivatives" according to which when said compounds are selected from the group consisting of: (a) 7β- acids acylamido-3-acetoxymethyl cef-3-em-4-carboxylic acids, wherein the acylamido group at position 7β is 2-aryloxyimino-2-phenylacelamido; 2-aryloxyimino-2-thienylacetamido; 2-aryloxyimino-2-furylacetamido; 2-cyclopentyloxyimino-2-phenylacelamido; 2-cyclopentyloxyimino-2-thienylacetamido; 2-cyclopentyloxyimino-2-furylacetamido; 2-t-butoxyimino-2- (benzo [b] furan-2-yl) acetamia; 2-methoxyimino-2- (N-methylpyrrol-2-yl) acetamido; 2-t-butoxyimino-2- (N-methylpyrrol-2-yl) acetamido; 2-thienylmethoxyimino-2- (N-methylpyrrol-2-yl) acetamido; 2-methoxyimino-2- (N-benzyloxymethylpyrrol-2-yl) acetamido; or 2-carboxymethoxyimino-2-phenylacetamido; the aryl part of said aryloxy group comprising phenyl, thienyl, furyl or phenyl substituted by one or more of chlorine, nitro, amino, carboxy and methoxy; (b) 7β-acylamido-3- (1-methyltetrazol-5-ylthiomethyl) cef-3-em-4-carboxylic acids and 7β-acylamido-3- (1-ethyltetrazol-5-thiomethyl) cef-3-em-4 acids -carboxylics in which the acylamido group in position 7β is a group of formula RC (: NORa) .CO- where R is selected from phenyl, thienyl, and furyl and Ra is selected from methyl, ethyl, t-butyl, cyclopentyl, phenyl, furylmethyl and triphenylmethyl; (c) 7β-acylamido-3- (5-nitrobenzothiazol-2-ylthiomethyl) cef-3-em-4-carboxylic acids and 7β-acylamido-3- (6-nitrobenzothiazol-2-ylthiomethyl) cef-3-em -4-carboxylic acids where the acylamido group in the 7β position is a group of formula RC (: NORa) .CO where R is selected from phenyl, thienyl and furyl and Ra is selected from t-butyl, cyclopentyl and phenyl; (d) 7β-acylamido-3-vinyl cef-3-em-4-carboxylic acids wherein the acylamido group at the 7β position is 2-t-butoxyimino-2-thienylacetamido; 2-ethoxyimino-2-phenylacetamido; or 2-t-butoxyimino-2- (benzo [b] thien-3-yl) acetamido; (e) 7β-acylamido-3-crotonyloxymethyl cef-3-em-4-carboxylic acids where the acylamido group at position 7β is 2-t-butoxyimino-2-thienylacetamido or 2-t-butoxyimino-2- (benzo [b ] -tien-3-yl) acetamido; (f) 7β- [2-t-butoxyimino-2-thienylacetamido] -3- (2-phenyl-1,3,4, -oxadiazol-5-ylthiomethyl) cef3-em-4-carboxylic acid; (g) 3-acetylthiomethyl-7β- (2-ethoxyimino-2-phenylacetamido) -cef-3-em-4-carboxylic acid; and non-toxic derivatives of these acids, said compound existing as an isomer without or a mixture of an isomer without such and the corresponding anti-isomer, where the configuration does not predominate, and which have the general formula **(See formula)** [where Ra and P have appropriate meanings corresponding to those encompassed by (a) - (g) above] said improvements comprise either (A) condensing a compound of formula **(See formula)** (where P has the meaning before indicated and R1 represents hydrogen or a carboxyl group blocking group) with an acylating agent corresponding to the acid Rα.OR (III) (Wherein, Rα has the meaning indicated above); or (b) reacting a compound of formula **(See formula)** (where Rα and R1 have the meanings indicated above and P1 is a precursor of the desired P-substituent), with a reagent or reagents serving to introduce said group P; and (C) recovering the desired compound of formula I, if necessary after separation of isomers and/or removal of any carboxyl group blocking groups and if desired after conversion of compound (I) into a non-toxic derivative. . (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4925572A GB1445979A (en) | 1972-10-25 | 1972-10-25 | Cephalosporin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES419927A2 true ES419927A2 (en) | 1976-11-16 |
Family
ID=10451708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES419927A Expired ES419927A2 (en) | 1972-10-25 | 1973-10-24 | Cephalosporin derivatives |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4972286A (en) |
| BE (1) | BE806450R (en) |
| ES (1) | ES419927A2 (en) |
| FR (1) | FR2204403B2 (en) |
| GB (1) | GB1445979A (en) |
| LU (1) | LU68680A1 (en) |
| ZA (1) | ZA738251B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144392A (en) | 1973-12-21 | 1979-03-13 | Glaxo Laboratories Limited | Cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyimino-arylacetamido group and at position-3 the residue of a sulphur nucleophile |
| US4144393A (en) | 1973-12-21 | 1979-03-13 | Glaxo Laboratories Limited | 3-Acetoxymethyl cephalosporins having at position-7 a carboxy substituted α-etherified hydroxyiminoarylacetamido group |
| US4165430A (en) | 1976-03-19 | 1979-08-21 | Glaxo Laboratories Limited | Cephalosporins having a 7-carboxy substituted α-etherified oximinoarylacetamido) group |
| GB1576625A (en) * | 1976-04-12 | 1980-10-08 | Fujisawa Pharmaceutical Co | Syn isomer 3,7 disubstituted 3 cephem 4 carboxylic acid compounds and processes for the preparation thereof |
| FI771866A7 (en) * | 1976-06-28 | 1977-12-29 | Fujisawa Pharmaceutical Co | |
| GB1592149A (en) * | 1976-10-08 | 1981-07-01 | Fujisawa Pharmaceutical Co | 3 7-disubstituted-3-cephem-4-carboxylic acid compounds and processes for preparation thereof |
| US4409214A (en) | 1979-11-19 | 1983-10-11 | Fujisawa Pharmaceutical, Co., Ltd. | 7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof |
| JPS5818388A (en) * | 1981-07-28 | 1983-02-02 | Banyu Pharmaceut Co Ltd | Preparation of 3-substituted thiomethylcephalosporin derivative |
| US4492693A (en) * | 1983-04-12 | 1985-01-08 | Eli Lilly And Company | Benzothienylglycyl cephalosporin derivatives |
| GB8927871D0 (en) * | 1989-12-08 | 1990-02-14 | Beecham Group Plc | Novel compounds |
| RU2420525C2 (en) * | 2005-07-11 | 2011-06-10 | Мицубиси Танабе Фарма Корпорейшн | Oxime derivatives and preparation thereof |
| JP2008019241A (en) * | 2007-03-01 | 2008-01-31 | Mitsubishi Tanabe Pharma Corp | Oxime derivatives and process for producing the same |
| WO2018053587A1 (en) * | 2016-09-21 | 2018-03-29 | Vectus Biosystems Limited | Compositions for the treatment of hypertension and/or fibrosis |
| FR3135420B1 (en) | 2022-05-10 | 2024-03-29 | Psa Automobiles Sa | System for holding the end of a screw in a frame rail for a motor vehicle |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1399086A (en) * | 1971-05-14 | 1975-06-25 | Glaxo Lab Ltd | Cephalosporin compounds |
-
1972
- 1972-10-25 GB GB4925572A patent/GB1445979A/en not_active Expired
- 1972-11-14 JP JP47114203A patent/JPS4972286A/ja active Pending
-
1973
- 1973-10-24 BE BE137009A patent/BE806450R/en active
- 1973-10-24 FR FR7337851A patent/FR2204403B2/fr not_active Expired
- 1973-10-24 ES ES419927A patent/ES419927A2/en not_active Expired
- 1973-10-24 LU LU68680A patent/LU68680A1/xx unknown
- 1973-10-24 ZA ZA738251A patent/ZA738251B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA738251B (en) | 1974-10-30 |
| JPS4972286A (en) | 1974-07-12 |
| FR2204403B2 (en) | 1976-12-24 |
| LU68680A1 (en) | 1974-01-08 |
| GB1445979A (en) | 1976-08-11 |
| BE806450R (en) | 1974-04-24 |
| FR2204403A2 (en) | 1974-05-24 |
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