ES419313A1 - Process for producing 7-amino and 7-acylamino-7-alkoxycephalo sporins - Google Patents
Process for producing 7-amino and 7-acylamino-7-alkoxycephalo sporinsInfo
- Publication number
- ES419313A1 ES419313A1 ES419313A ES419313A ES419313A1 ES 419313 A1 ES419313 A1 ES 419313A1 ES 419313 A ES419313 A ES 419313A ES 419313 A ES419313 A ES 419313A ES 419313 A1 ES419313 A1 ES 419313A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- formula
- see formula
- alkanoyl
- defined above
- 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 3
- -1 methyl-d3 group Chemical group 0.000 abstract 15
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 125000001589 carboacyl group Chemical group 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000001894 2,4,6-trinitrophenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1[N+]([O-])=O)[N+]([O-])=O)[N+]([O-])=O 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 150000001649 bromium compounds Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000020176 deacylation Effects 0.000 abstract 1
- 238000005947 deacylation reaction Methods 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000005179 haloacetyl group Chemical group 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
- 238000011065 in-situ storage Methods 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 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
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)
Abstract
A procedure for the preparation of 7-acylamido-7-alkoxycephalosporins of formula: **(See formula)** where Ro represents a C1-C4 primary lower alkyl or methyl-d3 group; R1 represents acetoxy, carbamoyloxy, α-methoxy-p-hydroxycinmoyloxy, propionyloxy, benzoyloxy, methoxy, methylthio, 1-ethyl-1,2,3,4-tetrazol-5-ylthio or 5-methyl-1,3,4- thiadiazol-2-ylthio; R2A represents hydrogen or R2; and R2 represents C1-C6-alkyl, 2,2,2-trichlorethyl, 2-iodoethyl, C5-C7-tert-alkenyl, C5-C7-tert-alkynyl, benzyl, ar-nitrobenzyl, tetrahydropyranyl, succinimidormethyl, phthalimidomethyl, ar-methoxybenzyl, ar, ar-dimethoxybenzyl, cyanomethyl, nitrophenyl, dinitrophenyl, 2,4,6-trinitrophenyl, bi- (p-methoxyphenyl) -methyl, triphenylmethyl, diphenylamethyl, benzyloxymethyl, alkanoyl (lower) oxymethyl C3-C6 or phenacyl; and R5 represents C1-C8 alkanoyl, axidoacetyl, cyanoacetyl, haloacetyl, (see formula) where Ar means phenyl, thienyl, furipyrrolyl or phenyl substituted with 1 to 3 substituents selected from the group consisting of fluorine, chlorine, bromine, iodine, trifluoromethyl, protected amino, protected hydroxy, C1-C3 alkyl, C1- alkoxy C3, cyano and nitro; (see formula) where Ar'represents phenyl, pyridyl or substituted phenyl as defined above and Y is oxygen or sulfur; (see formula) where Ar is the one defined above and B is a protected amino group, hydroxy protected, carboxy protected, -CN or -N3; 2- (3-sidnon) acetyl or 2- (1H-tetrazol-1-yl) acetyl, by deacylation of an iminohalide of a 7-acylamidocephalosporin by reaction with an alcohol whose process is characterized by reacting an iminohalide compound of formula: **(See formula)** where X represents bromide or chloride; R1 is the one defined above; R2B represents R2 as defined above, C2-C4 lower alkanoyl or a radical of formula: **(See formula)** wherein each R3 group independently represents C1-C4 lower alkyl or halogen selected from the group consisting of bromine, chlorine, fluorine and iodine, with the limitation that at least one R3 group represents lower alkyl; and R4 represents an acylamido group where the acyl is C1-C4 alkanoyl, benzoyl, naphthoyl, C2-C5 alkoxycarbonyl, C6-C7 cycloalkoxycarbonyl, benzyloxycarbonyl, naphthyloxycarbonyl, one of the above groups substituted with one to three groups, each of them selected from the group consisting of halogen, nitro, C1-C4 lower alkoxy, cyano and, in the case of benzoyl, naphthoyl, benzyloxy and naphthyloxy, by lower alkyl C1-C4 or phthaloyl; with an alcohol of the formula Ro-OH, under essentially non-aqueous conditions; and reacting the product therefrom in situ with a compound of one of the formulas X-R5 and O - (- R5) 2 where X represents bromine or chlorine and R5 has the meaning given above. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29816572A | 1972-10-16 | 1972-10-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES419313A1 true ES419313A1 (en) | 1976-06-16 |
Family
ID=23149341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES419313A Expired ES419313A1 (en) | 1972-10-16 | 1973-10-03 | Process for producing 7-amino and 7-acylamino-7-alkoxycephalo sporins |
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 |
|---|---|---|---|---|
| GB1348985A (en) * | 1970-06-16 | 1974-03-27 | Merck & Co Inc | Esters of cephalosporin compounds |
| 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 GB GB4609373A patent/GB1445743A/en not_active Expired
- 1973-10-03 ES ES419313A patent/ES419313A1/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 SE SE7313930A patent/SE408424B/en unknown
- 1973-10-12 DE DE2351375A patent/DE2351375C2/en not_active Expired
- 1973-10-13 PL PL1973165827A patent/PL91578B1/pl unknown
- 1973-10-15 BE BE1005431A patent/BE806068A/en not_active IP Right Cessation
- 1973-10-15 FR FR7336757A patent/FR2202895B1/fr not_active Expired
- 1973-10-15 DD DD174064A patent/DD111210A5/xx unknown
- 1973-10-15 DK DK557473A patent/DK153153C/en not_active IP Right Cessation
- 1973-10-15 SU SU731964431A patent/SU686621A3/en active
- 1973-10-15 AT AT876073A patent/AT328080B/en active
- 1973-10-16 JP JP11674873A patent/JPS5541238B2/ja not_active Expired
- 1973-10-16 CH CH1465173A patent/CH599221A5/xx not_active IP Right Cessation
- 1973-10-16 NL NL7314260A patent/NL7314260A/xx active Search and Examination
- 1973-10-16 BG BG024765A patent/BG25802A3/en unknown
- 1973-10-16 CS CS737127A patent/CS188905B2/en unknown
- 1973-10-16 HU HUEI500A patent/HU166991B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2351375A1 (en) | 1974-04-25 |
| AU6002873A (en) | 1975-03-06 |
| BG25802A3 (en) | 1978-12-12 |
| JPS4972289A (en) | 1974-07-12 |
| NL7314260A (en) | 1974-04-18 |
| IE38194B1 (en) | 1978-01-18 |
| FR2202895B1 (en) | 1978-11-10 |
| FR2202895A1 (en) | 1974-05-10 |
| YU265473A (en) | 1982-06-18 |
| SU686621A3 (en) | 1979-09-15 |
| CH599221A5 (en) | 1978-05-12 |
| AR206204A1 (en) | 1976-07-07 |
| BE806068A (en) | 1974-04-16 |
| IE38194L (en) | 1974-04-16 |
| RO63007A (en) | 1978-06-15 |
| JPS5541238B2 (en) | 1980-10-22 |
| PL91578B1 (en) | 1977-03-31 |
| DE2351375C2 (en) | 1985-07-11 |
| ATA876073A (en) | 1975-05-15 |
| DK153153B (en) | 1988-06-20 |
| HU166991B (en) | 1975-07-28 |
| YU36972B (en) | 1984-08-31 |
| ZA736077B (en) | 1975-04-30 |
| AT328080B (en) | 1976-03-10 |
| SE408424B (en) | 1979-06-11 |
| DD111210A5 (en) | 1975-02-05 |
| IL43170A (en) | 1976-08-31 |
| GB1445743A (en) | 1976-08-11 |
| IL43170A0 (en) | 1973-11-28 |
| CA1042421A (en) | 1978-11-14 |
| DK153153C (en) | 1988-12-05 |
| CS188905B2 (en) | 1979-03-30 |
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