IE34699L - Cephalosporin compounds - Google Patents
Cephalosporin compoundsInfo
- Publication number
- IE34699L IE34699L IE701411A IE141170A IE34699L IE 34699 L IE34699 L IE 34699L IE 701411 A IE701411 A IE 701411A IE 141170 A IE141170 A IE 141170A IE 34699 L IE34699 L IE 34699L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- integer
- group
- hydroxy
- blocked
- Prior art date
Links
- -1 Cephalosporin compounds Chemical class 0.000 title abstract 6
- 229930186147 Cephalosporin Natural products 0.000 title abstract 5
- 229940124587 cephalosporin Drugs 0.000 title abstract 5
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- 150000001780 cephalosporins Chemical class 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 230000000903 blocking effect Effects 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000003776 cleavage reaction Methods 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
- 125000003396 thiol group Chemical group [H]S* 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1302015 Cephalosporins ELI LILLY & CO 5 Nov 1970 [13 Nov 1969] 52755/70 Heading C2A A method for the cleavage of the 7-carboxamido group of a cephalosporin of Formula I wherein R is aminoadipoyl, C 2 -C 8 alkanoyl, a group of Formula II, III or IV X is C 2 -C 6 alkanoyloxy, C 2 -C 6 thioalkanoyloxy, C 6 -C 12 thioaroyloxy, hydroxy, mercapto, hydrogen, C 1 -C 6 alkoxy or C 1 -C 6 alkylthio, Y is O, S or a carbon-to-carbon bond; n is an integer of 0-3 and is at least 1 when Y is O or S; m is an integer of 1 to 3 and Q is amino or hydroxy; comprises blocking the carboxyl, amino, hydroxy and mercapto groups in the molecule, treating the blocked cephalosporin with a halogenating agent to convert the 7 -carboxamido group to an imino halide, treating the imino halide with an alkanol or benzyl alcohol to form an imino ether, and hydrolysing the imino ether to form a 7-amino group and blocking the carboxyl groups by converting them to a mixed anhydride derived from an acid having the formula R<SP>1</SP>-COOH, wherein R<SP>1</SP> is C 1 -C 8 alkyl, alkenyl or alkynyl or a group of Formula V or VI wherein Y is O, S or a carbon-to-carbon bond, n is an integer of 0 to 3 and is at least 1 when Y is O or S ; Z is O, S or and m is an integer of 1 to 3. The invention also comprises blocked cephalosporins of general formula VII whose carboxyl groups are blocked by converting them to a mixed anhydride derived from an acid which has the general formula R<SP>1</SP> being defined as above.
[GB1302015A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87659769A | 1969-11-13 | 1969-11-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34699L true IE34699L (en) | 1971-05-13 |
| IE34699B1 IE34699B1 (en) | 1975-07-23 |
Family
ID=25368102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1411/70A IE34699B1 (en) | 1969-11-13 | 1970-11-05 | Method of cleaving the 7-carboxamido group of a cephalosporin compound |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS4940479B1 (en) |
| AT (1) | AT301027B (en) |
| BE (1) | BE758800A (en) |
| BR (1) | BR6915070D0 (en) |
| CA (1) | CA977747A (en) |
| CH (1) | CH550200A (en) |
| CS (1) | CS167298B2 (en) |
| CY (1) | CY798A (en) |
| DE (1) | DE2056491A1 (en) |
| ES (1) | ES385395A1 (en) |
| FR (1) | FR2067278B1 (en) |
| GB (1) | GB1302015A (en) |
| HK (1) | HK17576A (en) |
| IE (1) | IE34699B1 (en) |
| IL (1) | IL35522A (en) |
| MY (1) | MY7500099A (en) |
| NL (1) | NL171899C (en) |
| NO (1) | NO143318C (en) |
| PL (1) | PL88926B1 (en) |
| RO (1) | RO58347A (en) |
| SE (1) | SE380808B (en) |
| SU (1) | SU501676A3 (en) |
| YU (1) | YU36183B (en) |
| ZA (1) | ZA707137B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248993B1 (en) * | 1971-07-29 | 1977-12-14 | ||
| US4008231A (en) * | 1975-09-15 | 1977-02-15 | Eli Lilly And Company | Preparation of 3-methoxymethylcephalosporins |
| GR70261B (en) * | 1977-12-12 | 1982-09-02 | Takeda Chemical Industries Ltd |
-
0
- BE BE758800D patent/BE758800A/en not_active IP Right Cessation
-
1969
- 1969-12-12 BR BR215070/69A patent/BR6915070D0/en unknown
-
1970
- 1970-10-20 ZA ZA707137A patent/ZA707137B/en unknown
- 1970-10-25 IL IL35522A patent/IL35522A/en unknown
- 1970-11-05 CY CY798A patent/CY798A/en unknown
- 1970-11-05 IE IE1411/70A patent/IE34699B1/en unknown
- 1970-11-05 GB GB5275570A patent/GB1302015A/en not_active Expired
- 1970-11-05 NL NLAANVRAGE7016199,A patent/NL171899C/en not_active IP Right Cessation
- 1970-11-06 CA CA097,580A patent/CA977747A/en not_active Expired
- 1970-11-09 SU SU1490795A patent/SU501676A3/en active
- 1970-11-10 ES ES385395A patent/ES385395A1/en not_active Expired
- 1970-11-10 CS CS7557A patent/CS167298B2/cs unknown
- 1970-11-10 SE SE7015136A patent/SE380808B/en unknown
- 1970-11-11 NO NO4303/70A patent/NO143318C/en unknown
- 1970-11-11 YU YU2762/70A patent/YU36183B/en unknown
- 1970-11-11 JP JP45099376A patent/JPS4940479B1/ja active Pending
- 1970-11-12 PL PL1970144387A patent/PL88926B1/pl unknown
- 1970-11-12 DE DE19702056491 patent/DE2056491A1/en active Pending
- 1970-11-12 CH CH1675670A patent/CH550200A/en not_active IP Right Cessation
- 1970-11-13 FR FR707040881A patent/FR2067278B1/fr not_active Expired
- 1970-11-13 RO RO64970A patent/RO58347A/ro unknown
- 1970-11-13 AT AT1025670A patent/AT301027B/en not_active IP Right Cessation
-
1975
- 1975-12-30 MY MY99/75A patent/MY7500099A/en unknown
-
1976
- 1976-03-25 HK HK175/76*UA patent/HK17576A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA977747A (en) | 1975-11-11 |
| NO143318B (en) | 1980-10-06 |
| MY7500099A (en) | 1975-12-31 |
| NL7016199A (en) | 1971-05-17 |
| NO143318C (en) | 1981-01-14 |
| IL35522A0 (en) | 1970-12-24 |
| BR6915070D0 (en) | 1973-07-17 |
| SU501676A3 (en) | 1976-01-30 |
| IL35522A (en) | 1974-09-10 |
| ES385395A1 (en) | 1973-04-16 |
| RO58347A (en) | 1975-09-15 |
| AT301027B (en) | 1972-08-25 |
| JPS4940479B1 (en) | 1974-11-02 |
| CH550200A (en) | 1974-06-14 |
| SE380808B (en) | 1975-11-17 |
| NL171899B (en) | 1983-01-03 |
| DE2056491A1 (en) | 1971-08-26 |
| YU36183B (en) | 1982-02-25 |
| PL88926B1 (en) | 1976-10-30 |
| CS167298B2 (en) | 1976-04-29 |
| CY798A (en) | 1976-12-01 |
| GB1302015A (en) | 1973-01-04 |
| HK17576A (en) | 1976-04-02 |
| IE34699B1 (en) | 1975-07-23 |
| NL171899C (en) | 1983-06-01 |
| BE758800A (en) | 1971-05-12 |
| YU276270A (en) | 1981-06-30 |
| FR2067278A1 (en) | 1971-08-20 |
| FR2067278B1 (en) | 1973-02-02 |
| ZA707137B (en) | 1972-05-31 |
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