IE37053L - Penicillin and cephalosporin derivatives - Google Patents
Penicillin and cephalosporin derivativesInfo
- Publication number
- IE37053L IE37053L IE730002A IE273A IE37053L IE 37053 L IE37053 L IE 37053L IE 730002 A IE730002 A IE 730002A IE 273 A IE273 A IE 273A IE 37053 L IE37053 L IE 37053L
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- formula
- group
- jan
- hydroxy
- Prior art date
Links
- 229930186147 Cephalosporin Chemical class 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title abstract 2
- 150000001780 cephalosporins Chemical class 0.000 title abstract 2
- 229930182555 Penicillin Natural products 0.000 title 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 title 1
- 229940049954 penicillin Drugs 0.000 title 1
- -1 D-α-hydroxyisocaproic acid succinimide Chemical compound 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NYHNVHGFPZAZGA-RXMQYKEDSA-N (2r)-2-hydroxyhexanoic acid Chemical compound CCCC[C@@H](O)C(O)=O NYHNVHGFPZAZGA-RXMQYKEDSA-N 0.000 abstract 1
- LVRFTAZAXQPQHI-UHFFFAOYSA-N 2-hydroxy-4-methylvaleric acid Chemical compound CC(C)CC(O)C(O)=O LVRFTAZAXQPQHI-UHFFFAOYSA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 238000007920 subcutaneous administration Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
1355629 Hydroxyalkylpenicillins and cephalosporins F HOFFMANN-LA ROCHE & CO AG 2 Jan 1973 [3 Jan 1972] 202/73 Headings C2C and C2A Novel D-compounds having the general Formula I wherein R represents an n-butyl or isobutyl group and A represents a group of Formula (a) or (b) and its salts and their hydrates may be prepared by reacting an amine of general Formula II wherein A<SP>1</SP> represents a group of Formula (a<SP>1</SP>) or (b<SP>1</SP>) in which X represents a protected carboxy group, with a D-acid of Formula III where R is as defined above, or with a functional derivative thereof, cleaning off the protecting group and, if desired, converting the product into a salt. The compounds of the invention are thus D - 1 - hydroxy-3 - methylbutylpenicillin, D - 1- hydroxypentylpenicillin, D-1-hydroxy-3-methylbutylcephalosporin and D-1-hydroxypentylcephalosporin. D-α-hydroxyisocaproic acid succinimide and D-α-hydroxycaproic acid succinimide are prepared by reaction of D-α-hydroxyisocaproic acid and D-α-hydroxycaproic acid respectively with N-hydroxysuccinimide and dicyclohexylcarbodiirnide. 6-Aminopenicillanic acid and 7-aminocephalosporanic acid are reacted with triethylamine in chloroform or methylene chloride to obtain the corresponding amine salts. Pharmaceutical compositions having antibiotic, especially bactericidal, activity for parenteral, peroral or subcutaneous administration comprise a compound of Formula I together with a compatible pharmaceutical carrier optionally together with other known additives, such as preserving, stabilizing, wetting or emulsifying agents and/or with other known therapeutically valuable substances.
[GB1355629A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH572A CH565182A5 (en) | 1972-01-03 | 1972-01-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37053L true IE37053L (en) | 1973-07-03 |
| IE37053B1 IE37053B1 (en) | 1977-04-27 |
Family
ID=4177249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2/73A IE37053B1 (en) | 1972-01-03 | 1973-01-02 | Penicillin and cephalosporin derivatives |
Country Status (16)
| Country | Link |
|---|---|
| AR (1) | AR205150A1 (en) |
| AT (1) | AT320153B (en) |
| BE (1) | BE793595A (en) |
| CA (1) | CA1001155A (en) |
| CH (1) | CH565182A5 (en) |
| DE (1) | DE2262472A1 (en) |
| DK (1) | DK140553B (en) |
| FR (1) | FR2181649B1 (en) |
| GB (1) | GB1355629A (en) |
| HU (1) | HU170008B (en) |
| IE (1) | IE37053B1 (en) |
| IL (1) | IL40978A (en) |
| NL (1) | NL7217543A (en) |
| PH (1) | PH11075A (en) |
| SE (1) | SE412065B (en) |
| ZA (1) | ZA728418B (en) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB940712A (en) * | 1961-06-23 | 1963-10-30 | Beecham Res Lab | Improvements in or relating to penicillins |
| FR1393244A (en) * | 1962-05-21 | 1965-03-26 | Beecham Group Ltd | Process for the preparation of penicillins |
| FR1393245A (en) * | 1962-05-21 | 1965-03-26 | Beecham Group Ltd | Process for the preparation of penicillins |
| SE311519B (en) * | 1962-12-14 | 1969-06-16 | Astra Ab |
-
0
- BE BE793595D patent/BE793595A/en unknown
-
1972
- 1972-01-03 CH CH572A patent/CH565182A5/xx not_active IP Right Cessation
- 1972-11-27 ZA ZA728418A patent/ZA728418B/en unknown
- 1972-12-01 DK DK603572AA patent/DK140553B/en unknown
- 1972-12-01 IL IL40978A patent/IL40978A/en unknown
- 1972-12-20 DE DE2262472A patent/DE2262472A1/en not_active Withdrawn
- 1972-12-22 NL NL7217543A patent/NL7217543A/xx not_active Application Discontinuation
- 1972-12-22 PH PH14198A patent/PH11075A/en unknown
-
1973
- 1973-01-01 AR AR245959A patent/AR205150A1/en active
- 1973-01-02 CA CA160,421A patent/CA1001155A/en not_active Expired
- 1973-01-02 AT AT1373A patent/AT320153B/en not_active IP Right Cessation
- 1973-01-02 GB GB20273A patent/GB1355629A/en not_active Expired
- 1973-01-02 IE IE2/73A patent/IE37053B1/en unknown
- 1973-01-02 SE SE7300033A patent/SE412065B/en unknown
- 1973-01-03 FR FR7300110A patent/FR2181649B1/fr not_active Expired
- 1973-01-03 HU HU73HO1538A patent/HU170008B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE37053B1 (en) | 1977-04-27 |
| SE412065B (en) | 1980-02-18 |
| NL7217543A (en) | 1973-07-05 |
| FR2181649A1 (en) | 1973-12-07 |
| FR2181649B1 (en) | 1976-03-05 |
| DK140553B (en) | 1979-10-01 |
| BE793595A (en) | 1973-07-02 |
| ZA728418B (en) | 1973-08-29 |
| PH11075A (en) | 1977-10-25 |
| IL40978A0 (en) | 1973-02-28 |
| DE2262472A1 (en) | 1973-07-19 |
| AU4949272A (en) | 1974-05-30 |
| AT320153B (en) | 1975-01-27 |
| CH565182A5 (en) | 1975-08-15 |
| AR205150A1 (en) | 1976-04-12 |
| CA1001155A (en) | 1976-12-07 |
| HU170008B (en) | 1977-03-28 |
| IL40978A (en) | 1975-10-15 |
| GB1355629A (en) | 1974-06-05 |
| DK140553C (en) | 1980-02-18 |
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