GB1438872A - 7-beta-aminoacylamino-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereof - Google Patents
7-beta-aminoacylamino-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereofInfo
- Publication number
- GB1438872A GB1438872A GB4121873A GB4121873A GB1438872A GB 1438872 A GB1438872 A GB 1438872A GB 4121873 A GB4121873 A GB 4121873A GB 4121873 A GB4121873 A GB 4121873A GB 1438872 A GB1438872 A GB 1438872A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- derivatives
- amino
- prepared
- 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
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- -1 7- amino - 3 - substituted - 3 - cephem - 4 - carboxylic acids Chemical class 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000004149 thio group Chemical group *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
- 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
- C07D501/36—Methylene radicals, substituted by sulfur atoms
-
- 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
- C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
-
- 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)
Abstract
1438872 7 - [# - Aminoacylamino] - 3 - substituted - 3 - cephem-4 - carboxylic acid derivatives FUJISAWA PHARMACEUTICAL CO Ltd 31 Aug 1973 [17 Nov 1972 14 Feb 1973] 41218/73 Heading C2C Novel cephalosporamic acid derivatives have the formula wherein R 1 is hydrogen lower alkyl, lower alkenyl, aryl or a heterocyclic group, R 2 is hydrogen or lower alkyl or R 1 and R 2 mean, taken together with the adjacent carbon atom, cycloalkyl or cycloalkenyl, R 3 is hydrogen, lower alkylthio or a heterocyclic thio group but excluding 5-methyl-1,3,4-thio diazol-2-ylthio when R 1 and R 2 taken together with the adjacent carbon atom are cyclohexyl and M is hydrogen, and M is hydrogen or a non-toxic, pharmaceutically acceptable cation. These derivatives may be prepared by acylating 7- amino - 3 - substituted - 3 - cephem - 4 - carboxylic acids of the formula with a #-amino aliphatic carboxylic acid derivative of the formula wherein X is protected amino, and if necessary removing the protective group of the amino radical. In the instance wherein R 3 is lower alkylthio or a heterocyclic-thio group, the derivatives may be prepared by reacting 7-acylated aminocephalosporacic acids with nucleophiles of formula R 3 -H and then if necessary, removing the protective groups of the amino radical. Further, when R 3 is hydrogen, the derivatives may be prepared by reducing 7-acylated amino cephalosporanic acids, and then, if necessary, removing a protective group on the amino radical. 1 - Aminocyclohexane - 1 - acetyl chloride is prepared by reacting the free acid with thionylchloride. The derivatives may be used in the form of a pharmaceutical preparation for therapeutic administration.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11598372A JPS5725557B2 (en) | 1972-11-17 | 1972-11-17 | |
| JP1863673A JPS563878B2 (en) | 1973-02-14 | 1973-02-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1438872A true GB1438872A (en) | 1976-06-09 |
Family
ID=26355341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4121873A Expired GB1438872A (en) | 1972-11-17 | 1973-08-31 | 7-beta-aminoacylamino-3-substituted-3-cephem-4-carboxylic acid derivatives and preparation thereof |
Country Status (7)
| Country | Link |
|---|---|
| CA (1) | CA1032534A (en) |
| CH (1) | CH589658A5 (en) |
| DE (1) | DE2344451C2 (en) |
| FR (1) | FR2206934B1 (en) |
| GB (1) | GB1438872A (en) |
| NL (1) | NL7312366A (en) |
| SE (1) | SE415019B (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518260A (en) * | 1965-03-08 | 1970-06-30 | Lilly Co Eli | Method for preparing aminoacyl cephalosporins |
| US3641021A (en) * | 1969-04-18 | 1972-02-08 | Lilly Co Eli | 3 7-(ring-substituted) cephalosporin compounds |
-
1973
- 1973-08-31 GB GB4121873A patent/GB1438872A/en not_active Expired
- 1973-09-03 SE SE7311986A patent/SE415019B/en unknown
- 1973-09-04 DE DE2344451A patent/DE2344451C2/en not_active Expired
- 1973-09-04 CA CA180,223A patent/CA1032534A/en not_active Expired
- 1973-09-06 CH CH1281973A patent/CH589658A5/xx not_active IP Right Cessation
- 1973-09-07 NL NL7312366A patent/NL7312366A/xx not_active Application Discontinuation
- 1973-09-18 FR FR7333385A patent/FR2206934B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH589658A5 (en) | 1977-07-15 |
| SE415019B (en) | 1980-09-01 |
| NL7312366A (en) | 1974-05-21 |
| DE2344451C2 (en) | 1983-02-03 |
| FR2206934A1 (en) | 1974-06-14 |
| CA1032534A (en) | 1978-06-06 |
| FR2206934B1 (en) | 1977-01-28 |
| DE2344451A1 (en) | 1974-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |