SE7512818L - PROCEDURE FOR PREPARING DELTA? 723-CEPHALOSPORIN ASSOCIATIONS - Google Patents
PROCEDURE FOR PREPARING DELTA? 723-CEPHALOSPORIN ASSOCIATIONSInfo
- Publication number
- SE7512818L SE7512818L SE7512818A SE7512818A SE7512818L SE 7512818 L SE7512818 L SE 7512818L SE 7512818 A SE7512818 A SE 7512818A SE 7512818 A SE7512818 A SE 7512818A SE 7512818 L SE7512818 L SE 7512818L
- Authority
- SE
- Sweden
- Prior art keywords
- alkyl
- formula
- alkanoyl
- cephalosporin
- hydrogen
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title abstract 10
- 238000000034 method Methods 0.000 title abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000001589 carboacyl group Chemical group 0.000 abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- -1 amino, protected amino, hydroxy Chemical group 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- 229930186147 Cephalosporin Natural products 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
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 239000012190 activator Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 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
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Chemical group 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- 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
-
- 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
-
- 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1,265,333. Preparing #<SP>3</SP>-cephalosporins from #<SP>2</SP>-cephalosporins. ELI LILLEY & CO. 7 Feb., 1969 [7 Feb., 1968; 13 Jan., 1969 (2)], No. 33268/70. Heading C2A. #<SP>3</SP>-Cephalosporin compounds are prepared by treating a corresponding #<SP>2</SP>-cephalosporin with an oxidizing agent to convert it to the #<SP>3</SP>- cephalosporin-1-sulphoxide and then reducing the sulphoxide. The #<SP>3</SP>-cephalosporins produced have the Formula I wherein R is hydrogen, a group of formula where X is amino, protected amino, hydroxy, C 1 to C 3 alkoxy, carboxyl or C 1 to C 3 alkanoyloxy; or R is a group of formula where X is oxygen, sulphur or a chemical bond, y is 0-2 and z is 1-3; or R is a group of formula and Q in each of the aforesaid groups is hydrogen, CN, NO 2 , OH, Cl, Br, F, CF 3 , C 1 to C 3 alkyl, C 1 to C 3 alkoxy, α-amino-C 1 to C 3 alkyl, carboxymethyl or carboxamidomethyl; or R is a group of formula where Y is sulphur or oxygen and each Z is hydrogen or Z and Z together with the carbons to which they are bonded complete a benzoring; or R is a group of formula where each of R<SP>1</SP> and R<SP>2</SP> is hydrogen, methyl, 2-sydnone-3-C 1 to C 3 alkanoyl, C 1 to C 10 alkanoyl, C 3 to C 10 alkenoyl, C 3 to C 7 alkyl-X-C 1 to C 3 alkanoyl where X is O or S, C 3 to C 7 alkenyl-XC 1 to C 3 alkanoyl where X is O or S, C 2 to C 10 haloalkanoyl where halo is Cl, Br or F, or C 2 to C 10 cyanoalkanoyl; and R<SP>1</SP> is cyano or -OY where Y is C 1 to C 10 alkyl, C 3 to C 10 alkenyl, C 3 to C 10 alkynyl, C 6 to C 7 cycloalkyl, C 5 to C 7 cycloalkyl-C 1 to C 3 alkyl, C 2 to C 10 haloalkyl, C 3 to C 10 haloalkenyl or C 3 to C 10 haloalkynyl, C 1 to C 3 alkyl-X-C 2 to C 6 alkyl where X is O or S, C 2 to C 4 alkanoyloxy-C 2 to C 6 alkyl, C 2 to C 4 alkanoyl-C 2 to C 6 alkyl, furyl-C 1 to C 3 alkyl, thienyl-C 1 to C 3 alkyl, 31-tetrahydrofuryl, tetrahydrofuryl-C 1 to C 3 alkyl, or phenyl, benzyl or phenethyl optionally substituted on ring carbons with C 1 to C 3 alkyl, C 1 to C 3 alkoxy, C 1 to C 3 alkoxycarbonyl, F, Cl, Br, NO 2 , CN or CF 3 ; and R<SP>11</SP> is hydrogen, a zwitterionic charge, a cation, C 4 to C 6 tert. alkyl, C 5 to C 7 tert. alkenyl, C 5 -C 7 tert. alkynyl, benzyl, methoxybenzyl, nitrobenzyl, benzhydryl, phthalimidomethyl, succinimidomethyl, trimethylsilyl or a phenacyl ester group. The corresponding #<SP>2</SP>-cephalosporin starting materials may be prepared by the process of Specification 1,265,332. The present process preferably employs oxidation with a per-acid, e.g. m-chloroperbenzoic acid, followed by reduction with sodium bisulphite or dithionite in the presence of an activator, e.g. acetyl chloride. Examples also are given for an alternative process wherein the #<SP>2</SP>-cephalosporin is partially isomerized with a base, e.g. pyridine, to give a mixture of #<SP>2</SP>- and #<SP>2</SP>-cephalosporins. Among the compounds prepared according to the invention are novel cephalosporins having the Formula I (as above), wherein R is 2-sydnone- 3-C 1 to C 3 alkanoyl, R<SP>1</SP> is -OY where Y is C 1 to C 10 alkyl, and R<SP>11</SP> is hydrogen.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70352368A | 1968-02-07 | 1968-02-07 | |
| US79084269A | 1969-01-13 | 1969-01-13 | |
| US79088669A | 1969-01-13 | 1969-01-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7512818L true SE7512818L (en) | 1975-11-14 |
| SE418616B SE418616B (en) | 1981-06-15 |
Family
ID=27418758
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE6901500A SE384511B (en) | 1968-02-07 | 1969-02-05 | 7-PROTECTED AMINO-DELTA? 722? 71-CEPHALOSPORANIC ACID, FOR USE AS INTERMEDIATE IN THE MANUFACTURE OF DELTA? 723? 71-CEPHALOSPORINE ANTIBIOTICS |
| SE7200411A SE407064B (en) | 1968-02-07 | 1972-01-14 | IN 7-FRAME PROTECTED 3-BROMOMETHYL-DELTAŸ2-CEPHALOSPORANIC ACID RESIDUES FOR USE AS AN INTERMEDIATE IN THE PRESENTATION OF ANTIBIOTIC ACTIVE DELTAŸ3-CEPHALOSPORANIC ACID DERIVATIVES |
| SE7512818A SE418616B (en) | 1968-02-07 | 1975-11-14 | PROCEDURE FOR PREPARATION OF DELTA? 723-CEPHALOSPORINE COMPOUNDS FROM 7-PROTECTED AMINO-DELTA? 722-CEPHALOSPORINE ESTERS |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE6901500A SE384511B (en) | 1968-02-07 | 1969-02-05 | 7-PROTECTED AMINO-DELTA? 722? 71-CEPHALOSPORANIC ACID, FOR USE AS INTERMEDIATE IN THE MANUFACTURE OF DELTA? 723? 71-CEPHALOSPORINE ANTIBIOTICS |
| SE7200411A SE407064B (en) | 1968-02-07 | 1972-01-14 | IN 7-FRAME PROTECTED 3-BROMOMETHYL-DELTAŸ2-CEPHALOSPORANIC ACID RESIDUES FOR USE AS AN INTERMEDIATE IN THE PRESENTATION OF ANTIBIOTIC ACTIVE DELTAŸ3-CEPHALOSPORANIC ACID DERIVATIVES |
Country Status (11)
| Country | Link |
|---|---|
| JP (3) | JPS524558B1 (en) |
| BE (1) | BE728053A (en) |
| CH (1) | CH534694A (en) |
| DK (1) | DK140726B (en) |
| FI (1) | FI56535C (en) |
| FR (3) | FR2001491B1 (en) |
| GB (2) | GB1265333A (en) |
| IL (2) | IL41553A (en) |
| LU (1) | LU57932A1 (en) |
| NL (1) | NL173407C (en) |
| SE (3) | SE384511B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2132883A1 (en) * | 1970-07-08 | 1972-01-13 | Ciba Geigy Ag | Cephem compounds |
| JPS53164082U (en) * | 1977-05-31 | 1978-12-22 | ||
| JPS5899787U (en) * | 1981-12-28 | 1983-07-07 | 奥野電器株式会社 | lamp socket |
| EP0300546B1 (en) * | 1987-07-10 | 1995-08-09 | Gist-Brocades N.V. | Process for the preparation of cephem compounds and cephalosporin derivatives |
-
1969
- 1969-02-04 FI FI326/69A patent/FI56535C/en active
- 1969-02-05 SE SE6901500A patent/SE384511B/en unknown
- 1969-02-06 IL IL41553A patent/IL41553A/en unknown
- 1969-02-06 LU LU57932D patent/LU57932A1/xx unknown
- 1969-02-06 IL IL40447A patent/IL40447A/en unknown
- 1969-02-06 DK DK63069AA patent/DK140726B/en not_active IP Right Cessation
- 1969-02-07 BE BE728053D patent/BE728053A/xx not_active IP Right Cessation
- 1969-02-07 NL NLAANVRAGE6902013,A patent/NL173407C/en not_active IP Right Cessation
- 1969-02-07 GB GB1265333D patent/GB1265333A/en not_active Expired
- 1969-02-07 JP JP44009211A patent/JPS524558B1/ja active Pending
- 1969-02-07 FR FR696902897A patent/FR2001491B1/fr not_active Expired
- 1969-02-07 GB GB1265332D patent/GB1265332A/en not_active Expired
- 1969-02-07 CH CH190469A patent/CH534694A/en not_active IP Right Cessation
-
1971
- 1971-03-03 FR FR7107344A patent/FR2095486A5/fr not_active Expired
- 1971-03-03 FR FR7107345A patent/FR2085656B1/fr not_active Expired
- 1971-08-13 JP JP46061594A patent/JPS4924076B1/ja active Pending
- 1971-08-13 JP JP46061595A patent/JPS524559B1/ja active Pending
-
1972
- 1972-01-14 SE SE7200411A patent/SE407064B/en unknown
-
1975
- 1975-11-14 SE SE7512818A patent/SE418616B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI56535B (en) | 1979-10-31 |
| GB1265332A (en) | 1972-03-01 |
| FR2001491B1 (en) | 1973-07-13 |
| SE407064B (en) | 1979-03-12 |
| NL6902013A (en) | 1969-08-11 |
| GB1265333A (en) | 1972-03-01 |
| FR2085656B1 (en) | 1974-08-23 |
| SE384511B (en) | 1976-05-10 |
| JPS524558B1 (en) | 1977-02-04 |
| SE418616B (en) | 1981-06-15 |
| DK140726C (en) | 1980-03-31 |
| DK140726B (en) | 1979-11-05 |
| JPS4924076B1 (en) | 1974-06-20 |
| CH534694A (en) | 1973-03-15 |
| IL40447A (en) | 1976-02-29 |
| NL173407C (en) | 1984-01-16 |
| JPS524559B1 (en) | 1977-02-04 |
| FR2085656A1 (en) | 1971-12-31 |
| FR2001491A1 (en) | 1969-09-26 |
| IL41553A (en) | 1976-02-29 |
| FR2095486A5 (en) | 1972-02-11 |
| FI56535C (en) | 1980-02-11 |
| BE728053A (en) | 1969-08-07 |
| LU57932A1 (en) | 1969-09-17 |
| NL173407B (en) | 1983-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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