GB1086494A - New penicillins - Google Patents
New penicillinsInfo
- Publication number
- GB1086494A GB1086494A GB4035764A GB4035764A GB1086494A GB 1086494 A GB1086494 A GB 1086494A GB 4035764 A GB4035764 A GB 4035764A GB 4035764 A GB4035764 A GB 4035764A GB 1086494 A GB1086494 A GB 1086494A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hal
- radical
- atom
- general formula
- same
- 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
- 229930182555 Penicillin Natural products 0.000 title 1
- 150000002960 penicillins Chemical class 0.000 title 1
- 150000003254 radicals Chemical class 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 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 2
- 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 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- -1 heterocyclic radical Chemical class 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to compounds of the general formula <FORM:1086494/C2/1> and their salts with non-toxic inorganic and organic bases. In the general formula, R1 and R2, which may be the same or different, are selected from (a), (b) and (c) and R3 and R4, which may also be the same or different, are selected from (a) and (d) wherein: (a) is a hydrogen atom or an alkyl, substituted alkyl, cycloalkyl (the ring of which may be interrupted by heteroatoms), aralkyl, aryl or heterocyclic radical; (b) is a F, Cl or Br atom or a radical of the general formula -OR, -O-CO-R, -O-CS-R, -O-CO-N(R)2, -SR, -S-CO-R, -S-CS-R, -S-CO-N(R2)2, -SO-R, -S-CS-N(R)2, -SO2-R, or -SO2-N(R)2, R having the same meaning as (a); (c) is a radical of the general formula -CO-R, -C(R)=N-R, -COOR, -COSR, -CSSR, -CO-N(R)2, -CS-N(R)2, -CN, <FORM:1086494/C2/2> <FORM:1086494/C2/3> -C (Halogen)3, -N(R)-CO-R, -N(CO-R), N(R)-COOR, -N(R)-CSOR, -N(R)-CSSR, -PO(X)Y or -C(OR)3, X and Y which may be the same or different being halogen atoms or radicals of the general formula -OR, -NH-R, -N(R2) or -SR, R having the same meaning as (a) except it must not be a H atom; and (d) is a radical of general formula -CH2-Hal, -CH(Hal)2, -C(Hal)3, -C(R11)2-Hal, CH (R11)-Hal or -C(R11)(Hal)2, Hal being a F, Cl or Br atom or a radical of group (c) wherein, when one C atom has more than one halogen atom attached to it, these can be the same or different, R11 is an alkyl, aralkyl or aryl radical containing up to 10 C atoms and when two R11 are attached to one C atom, they can be joined up to form a cycloaliphatic or heterocyclic ring. The compounds are prepared by reaction of 6 amino penicillanic acid with a b -lactone in the presence of a basic material. The reaction may be carried out in a diluent, e.g. water or aqueous organic or anhydrous organic solvents. The 6-amino penicillanic acid may be used in the form of a salt, or the carboxyl and/or amino group is first silylated and after the reaction the silyl radical is split off.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0040893 | 1963-10-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1086494A true GB1086494A (en) | 1967-10-11 |
Family
ID=7098423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4035764A Expired GB1086494A (en) | 1963-10-02 | 1964-10-02 | New penicillins |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE653862A (en) |
| GB (1) | GB1086494A (en) |
-
1964
- 1964-10-02 GB GB4035764A patent/GB1086494A/en not_active Expired
- 1964-10-02 BE BE653862D patent/BE653862A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE653862A (en) | 1965-04-02 |
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