IL43170A - Process for producing 7-acylamino-7-alkoxycephalosporins - Google Patents
Process for producing 7-acylamino-7-alkoxycephalosporinsInfo
- Publication number
- IL43170A IL43170A IL43170A IL4317073A IL43170A IL 43170 A IL43170 A IL 43170A IL 43170 A IL43170 A IL 43170A IL 4317073 A IL4317073 A IL 4317073A IL 43170 A IL43170 A IL 43170A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- loweralkyl
- methyl
- compounds
- acetoxy
- Prior art date
Links
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
- C07D501/18—7-Aminocephalosporanic or substituted 7-aminocephalosporanic acids
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (11)
1. A process for preparing compounds of the wherein R° represents primary loweralkyl of C1~C4 or methyl-d^; represents acetoxy, carbamoyloxy , a-methoxy-p_-hydroxy-cinnamoyloxy, propionyloxy , benzoyloxy, methoxy, methylthio, l-methyl-l,2,3,4-tetrazol-5-ylthio, or 5-methyl-l,3,4- 2A 2 2 thiadiazol-2-ylthio; R represents hydrogen or R ; and R represents alkyl of C^-C^, 2 ,2 , 2-trichloroethyl , 2-iodoethyl, tert-alkenyl of C..-C.-,, tert-alkynyl of benzyl, ar-nitrobenzyl , tetrahydropyranyl , succinimidomethyl , phthalimidomethyl , ar-methoxybenzyl , ar_, ar-dimethoxybenzyl , cyanomethyl, nitrophenyl, dinitrophenyl , 2,4,6-trinitrophenyl, bis (p_-methoxyphenyl) methyl, triphenylmethyl, diphenylmethyl, benzyloxymethyl, loweralkanoyloxymethyl of C^-Cg, or phenacyl; which process comprises reacting an imino halide compound of the formula: wherein X represents bromide or chloride; R is as 2B 2 defined above; R represents R as defined above, lower alkanoyl of C„-C- or radical of the formula: wherein each independently represents loweralkyl of C^-C^ or halo selected from the group consisting of bromo, chloro, fluoro, and iodo subject to the limitation that at 3 4 least one R represents loweralkyl as defined; and R represents an acylamido group wherein the acyl is alkanoyl of C^-C^ / 10 benzoyl, naphthoyl , alkoxycarbonyl of <^2~(~5' cycloalkoxycarbonyl of C^-C^, benzyloxycarbonyl , naphthyloxycarbonyl , one of the above groups substituted with from one to three groups, each selected from the group consisting of halo, nitro, loweralkoxy of C1~C4' cyano' an^ tne instance of benzoyl, 20 naphthoyl, benzyloxy, and naphthyloxy, by loweralkyl of C-^-C^, or phthaloyl ; with an alcohol of the formula R°-0H under essentially non-aqueous conditions.
2. The process of Claim 1 wherein R^ is acetoxy.
3. The process of Claim 1 wherein R^" is carbamoyloxy.
4. The process of Claim 1 wherein the product is subsequently reacted in situ with a compound of one of the wherein X represent alkanoyl; azidoacetyl ; cyanoacetyl ; haloacetyl ; Ar-CH2-?- where Ar denotes phenyl, thienyl, furyl, pyrrolyl, or phenyl substituted with from one to three substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, trifluoromethyl, hydroxy , C^-C^ alkyl, C^-C^ alkoxy, cyano, and nitro; Ar'-Y-CI^-?- where Ar' represents phenyl, pyridyl, or substituted phenyl as defined above, and Y is oxygen or sulfur; Ar-^H-§- where Ar is as defined above, and B is protected amino, protected hydroxy, protected carboxy, -CN or -N^ 2- (3-sydnone) acetyl ; or 2- (lH-tetrazol-l-yl) acetyl.
5. The process of Claim 4 wherein R^ represents acetoxy. 1
6. The process of Claim 4 wherein R represents carbamoyloxy .
7. Compounds of the formula 43170/2 1 2A 1 ' 2 wherein R represents acetoxy; R represents hydrogen or R ; 2 . and R represents ilkyl of C^-C^y ' diphenylmethyl . 22L
8. The compound of claim 7 wherein R represents, hydrogen.
9. Compounds of formula wherein R°, R and R are as defined in claim 1, when prepared by the process of claim 1.
10. -1-3-r- A process for preparing compounds of the formula wherein R°, R , and R are as defined in Claim 1 substantially as hereinbefore described with particular reference to the Examples . 10
11. . -Ί-3-. Compounds of the formula H wherein R and R are as defined in Claim 7 substantially as hereinbefore described with particular reference to Examples 6 and 7. S. HOROWITZ & CO. AGENTS FOR APPLICANTS
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29816572A | 1972-10-16 | 1972-10-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43170A0 IL43170A0 (en) | 1973-11-28 |
| IL43170A true IL43170A (en) | 1976-08-31 |
Family
ID=23149341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43170A IL43170A (en) | 1972-10-16 | 1973-09-06 | Process for producing 7-acylamino-7-alkoxycephalosporins |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5541238B2 (en) |
| AR (1) | AR206204A1 (en) |
| AT (1) | AT328080B (en) |
| BE (1) | BE806068A (en) |
| BG (1) | BG25802A3 (en) |
| CA (1) | CA1042421A (en) |
| CH (1) | CH599221A5 (en) |
| CS (1) | CS188905B2 (en) |
| DD (1) | DD111210A5 (en) |
| DE (1) | DE2351375C2 (en) |
| DK (1) | DK153153C (en) |
| ES (1) | ES419313A1 (en) |
| FR (1) | FR2202895B1 (en) |
| GB (1) | GB1445743A (en) |
| HU (1) | HU166991B (en) |
| IE (1) | IE38194B1 (en) |
| IL (1) | IL43170A (en) |
| NL (1) | NL7314260A (en) |
| PL (1) | PL91578B1 (en) |
| RO (1) | RO63007A (en) |
| SE (1) | SE408424B (en) |
| SU (1) | SU686621A3 (en) |
| YU (1) | YU36972B (en) |
| ZA (1) | ZA736077B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5811955B2 (en) * | 1977-08-08 | 1983-03-05 | 山之内製薬株式会社 | Novel synthesis method for 7a-methoxycephalosporanic acid derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1348984A (en) * | 1970-06-16 | 1974-03-27 | Merck & Co Inc | Antibiotics and processes for their production |
| DE2161659A1 (en) * | 1970-12-14 | 1972-08-03 | Yamanouchi Pharmaceutical Co. Ltd., Tokio | Process for the production of semi-synthetic penicillins |
-
1973
- 1973-01-01 AR AR250560A patent/AR206204A1/en active
- 1973-08-30 CA CA180,012A patent/CA1042421A/en not_active Expired
- 1973-09-03 IE IE1559/73A patent/IE38194B1/en unknown
- 1973-09-04 ZA ZA00736077A patent/ZA736077B/en unknown
- 1973-09-06 IL IL43170A patent/IL43170A/en unknown
- 1973-10-03 ES ES419313A patent/ES419313A1/en not_active Expired
- 1973-10-03 GB GB4609373A patent/GB1445743A/en not_active Expired
- 1973-10-08 RO RO7300076274A patent/RO63007A/en unknown
- 1973-10-10 YU YU2654/73A patent/YU36972B/en unknown
- 1973-10-12 DE DE2351375A patent/DE2351375C2/en not_active Expired
- 1973-10-12 SE SE7313930A patent/SE408424B/en unknown
- 1973-10-13 PL PL1973165827A patent/PL91578B1/pl unknown
- 1973-10-15 DK DK557473A patent/DK153153C/en not_active IP Right Cessation
- 1973-10-15 AT AT876073A patent/AT328080B/en active
- 1973-10-15 FR FR7336757A patent/FR2202895B1/fr not_active Expired
- 1973-10-15 DD DD174064A patent/DD111210A5/xx unknown
- 1973-10-15 BE BE1005431A patent/BE806068A/en not_active IP Right Cessation
- 1973-10-15 SU SU731964431A patent/SU686621A3/en active
- 1973-10-16 NL NL7314260A patent/NL7314260A/xx active Search and Examination
- 1973-10-16 JP JP11674873A patent/JPS5541238B2/ja not_active Expired
- 1973-10-16 HU HUEI500A patent/HU166991B/hu not_active IP Right Cessation
- 1973-10-16 CS CS737127A patent/CS188905B2/en unknown
- 1973-10-16 BG BG024765A patent/BG25802A3/en unknown
- 1973-10-16 CH CH1465173A patent/CH599221A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7314260A (en) | 1974-04-18 |
| IE38194L (en) | 1974-04-16 |
| BG25802A3 (en) | 1978-12-12 |
| SE408424B (en) | 1979-06-11 |
| DE2351375C2 (en) | 1985-07-11 |
| IE38194B1 (en) | 1978-01-18 |
| PL91578B1 (en) | 1977-03-31 |
| YU265473A (en) | 1982-06-18 |
| IL43170A0 (en) | 1973-11-28 |
| AT328080B (en) | 1976-03-10 |
| BE806068A (en) | 1974-04-16 |
| HU166991B (en) | 1975-07-28 |
| CS188905B2 (en) | 1979-03-30 |
| RO63007A (en) | 1978-06-15 |
| SU686621A3 (en) | 1979-09-15 |
| FR2202895A1 (en) | 1974-05-10 |
| ZA736077B (en) | 1975-04-30 |
| ATA876073A (en) | 1975-05-15 |
| FR2202895B1 (en) | 1978-11-10 |
| JPS4972289A (en) | 1974-07-12 |
| AU6002873A (en) | 1975-03-06 |
| DE2351375A1 (en) | 1974-04-25 |
| DK153153B (en) | 1988-06-20 |
| ES419313A1 (en) | 1976-06-16 |
| DD111210A5 (en) | 1975-02-05 |
| GB1445743A (en) | 1976-08-11 |
| CA1042421A (en) | 1978-11-14 |
| CH599221A5 (en) | 1978-05-12 |
| YU36972B (en) | 1984-08-31 |
| AR206204A1 (en) | 1976-07-07 |
| DK153153C (en) | 1988-12-05 |
| JPS5541238B2 (en) | 1980-10-22 |
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