ES338433A2 - Penicillins - Google Patents
PenicillinsInfo
- Publication number
- ES338433A2 ES338433A2 ES338433A ES338433A ES338433A2 ES 338433 A2 ES338433 A2 ES 338433A2 ES 338433 A ES338433 A ES 338433A ES 338433 A ES338433 A ES 338433A ES 338433 A2 ES338433 A2 ES 338433A2
- Authority
- ES
- Spain
- Prior art keywords
- alpha
- acid
- carbamido
- phenylacetamido
- carboxy
- 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 abstract 3
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 4
- -1 oyclobutane Chemical compound 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 abstract 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical group C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 abstract 2
- SYLAFCZSYRXBJF-UHFFFAOYSA-N furan-3,4-dicarboxylic acid Chemical compound OC(=O)C1=COC=C1C(O)=O SYLAFCZSYRXBJF-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 abstract 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 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 penicillins of formula and non-toxic salts thereof, where R is phenyl, substituted phenyl or thienyl and X is a divalent radical derived from a cyclopropane, oyclobutane, cyclopentane, cyclohexane, cyclohexene or cyclohexadiene ring system or from a 5- or 6-membered saturated or unsaturated heterocyclic ring containing a single hetero atom which is O or S. The X rings may be substituted with one or more substituents, e.g. halogen, C 1-5 alkyl, oxo or carboxyl. The cyclohexane, cyclohexene and cyclohexadiene rings may be bridged by means of -O- -O-CO-, -CH 2 - or -CH=CH-. The compounds may be prepared by reacting an [alpha]-amino penicillin of formula with a reactive derivative of the dicarboxylic acid HOOC-X-COOH, wherein X and R have the above values. The reactive derivative may be a cyclic anhydride or a bis-acid chloride. Typical compounds are 6 [D - [alpha] - (cis - 2 - carboxy cyclohexane - 1 - carbamido) phenylacetamido] penicillanic acid, 6 - [D - [alpha] - (cis - 2 - carboxy cyolohex - 4 - ene - 1 - carbamido) phenylacetamido] penicillanic acid and 6 - [D - [alpha] - (1 - carboxy cyclobutane - 1 - carbamido) phenylacetamido] penicillanic acid. The salts may be sodium, potassium, calcium, ammonium, aluminium or amine salts. The dimeric anhydride of furan-3,4-dicarboxylic acid is prepared by treating furan-3,4- dicarboxylic acid with thionyl chloride in benzene.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1322466A GB1125339A (en) | 1966-03-25 | 1966-03-25 | Penicillins |
| GB5520966 | 1966-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES338433A2 true ES338433A2 (en) | 1968-04-01 |
Family
ID=26249637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES338433A Expired ES338433A2 (en) | 1966-03-25 | 1967-03-23 | Penicillins |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT271724B (en) |
| BE (1) | BE696116A (en) |
| CH (1) | CH503762A (en) |
| DK (1) | DK132225C (en) |
| ES (1) | ES338433A2 (en) |
| GB (1) | GB1125339A (en) |
| NL (1) | NL155551B (en) |
| SE (1) | SE368407B (en) |
-
1966
- 1966-03-25 GB GB1322466A patent/GB1125339A/en not_active Expired
-
1967
- 1967-03-21 NL NL6704207A patent/NL155551B/en unknown
- 1967-03-21 SE SE396767A patent/SE368407B/xx unknown
- 1967-03-22 CH CH413667A patent/CH503762A/en not_active IP Right Cessation
- 1967-03-22 DK DK155767A patent/DK132225C/en active
- 1967-03-23 ES ES338433A patent/ES338433A2/en not_active Expired
- 1967-03-24 BE BE696116D patent/BE696116A/xx unknown
- 1967-03-24 AT AT288567A patent/AT271724B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NL155551B (en) | 1978-01-16 |
| DK132225B (en) | 1975-11-10 |
| DK132225C (en) | 1976-04-12 |
| GB1125339A (en) | 1968-08-28 |
| AT271724B (en) | 1969-06-10 |
| NL6704207A (en) | 1967-09-26 |
| SE368407B (en) | 1974-07-01 |
| BE696116A (en) | 1967-09-25 |
| CH503762A (en) | 1971-02-28 |
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