Claims
- 1. A member selected from the group consisting of mono- and diethers of Papulacandin A of the formula ##STR11## and mono- and diethers of Papulacandin B of the formula ##STR12## wherein each of R.sub.1 and R.sub.2 represents hydrogen or an unsubstituted or substituted hydrocarbon radical of the formula
- (IV) --CH.sub.2 --K having not more than 24 C atoms
- wherein K represents a member selected from the group consisting of
- (1) an unsubstituted unsaturated aliphatic hydrocarbon radical having 1-7 C atoms,
- (2) a member selected from the group consisting of phenyl, cycloalkyl of 3-8 ring C atoms, cycloalkenyl of 3-8 ring C atoms, cycloalkadienyl of 3-8 ring C atoms, and derivatives of these 4 groups substituted by alkyl groups having 1-4 C atoms
- or
- (3) a monocyclic heterocyclic radical selected from the group consisting of a 6-membered mono-aza-cyclic radical, a 5-membered mono-thia-cyclic radical and a 5-membered mono-oxa-cyclic radical, and derivatives of any of these heterocyclic radicals substituted at the ring by alkyl groups having 1-4 C atoms
- or
- (4) a saturated or unsaturated aliphatic hydrocarbon radical of 1-7 C atoms substituted by a member selected from the group consisting of phenyl, cycloalkyl of 3-8 ring C atoms, cycloalkenyl of 3-8 ring C atoms, cycloalkadienyl of 3-8 ring C atoms, a 6-membered mono-aza-cyclic radical, a 5-membered mono-thia-cyclic radical and a 5-membered mono-oxa-cyclic radical, and a derivative of any of these cyclic groups substituted at the ring by alkyl groups having 1-4 C atoms, or a saturated or unsaturated aliphatic hydrocarbon radical of 1-7 C atoms interrupted in the --C--C-chain by a divalent radical corresponding to any of the cyclic substituents mentioned, or
- K represents any radical as defined under items (1) to (4) which are furthermore substituted by one or more functional groups selected from the group consisting of free, etherified and esterified hydroxyl groups, mercapto, alkylthio and phenylthio groups, halogen atoms, cyano, azido, oxo and nitro groups, primary and secondary amino groups and corresponding acylamino groups, sulphamino groups, free carboxyl groups or esterified carboxyl groups, carbamoyl, ureidocarbonyl, guanidinocarbonyl or groups derived therefrom by substitution of the hydrogens of the NH.sub.2 group by lower alkyl, hydroxyalkyl or alkoxyalkyl groups, and sulpho groups, the acyl groups of esterified hydroxyl groups being derived from a carboxylic or sulphonic acid having not more than 18 C-atoms, and the ether groups or esterified carboxylic acid groups being derived from lower aliphatic alcohols, benzyl alcohol or benzhydrol or nitro or amino derivatives thereof, 2-tetrahydrofuranol or 2-tetrahydropyranol, tri-lower-alkylsilyl alcohol and phenyl-di-lower alkylsilyl-alcohol, with the proviso that at least one of the symbols R.sub.1 and R.sub.2 represents the hydrocarbon of the formula (IV),
- and therapeutically useful metal salts of the acidic ethers as defined and therapeutically useful acid addition salts or quaternary ammonium salts of the basic ethers as defined.
- 2. A compound according to claim 1, wherein R.sub.1 or R.sub.2 in formula (III) are hydrogen or a radical of one of the partial formulae
- --CH.sub.2 --A.sub.1
- --CH.sub.2 --Kw.sub.1 --A.sub.1
- --CH.sub.2 --Kw.sub.2 --A.sub.2 --Kw.sub.3
- in which Kw.sub.1 represents a saturated or unsaturated linear or branched aliphatic hydrocarbon radical containing 1 to 7 carbon atoms, and each of Kw.sub.2 and Kw.sub.3 also represents such a radical, with the proviso that Kw.sub.2 and Kw.sub.3 together do not contain more than 7 C atoms, and A.sub.1 represents a monocyclic hydrocarbon radical or a monocyclic heterocyclic radical and A.sub.2 represents a monocyclic hydrocarbon radical or a monocyclic heterocyclic radical, with the proviso that at least one of R.sub.1 and R.sub.2 is one of the said radicals.
- 3. A 10 mono-ether of Papulacandin B according to claim 1, wherein K in formula (IV) is a member selected from the group consisting of
- (a) a free carboxyl group, an esterified carboxyl group, a carbamide group which is N-unsubstituted or N-substituted by one or two lower alkyl radicals of 1 to 7 carbon atoms, a cyano group
- (b) a lower alkyl radical of 1 to 7 carbon atoms which is substituted by any of the groups mentioned in (a), any ester group being derived from a lower mono- or polyhydric alcohol of 1 to 7 carbon atoms, and lower alkyl radicals substituting the amide N being optionally substituted by hydroxy or amino.
- 4. A 12-monoether of Papulacandin A or Papulacandin B according to claim 1.
- 5. A 10,12-diether of Papulacandin A or Papulacandin B according to claim 1.
- 6. A 10-monoether of Papulacandin A or Papulacandin B according to claim 1.
- 7. A compound according to claim 1 wherein the ether groups contain functional groups which are capable of salt formation, and the water-soluble salts thereof.
- 8. Acid addition salts of a compound according to claim 1 which contain basic groups which are derived from therapeutically useful acids.
- 9. Quaternary ammonium salts of a compound according to claim 1 which are derived from therapeutically useful acids.
- 10. A diether of Papulacandin A and B according to claim 1 wherein the ether radical in the 12-position is p-nitrobenzyl or p-aminobenzyl.
- 11. A compound as claimed in claim 1 which is a member selected from the group consisting of Papulacandin B-10,12-diallyl ether and Papulacandin B-12-monoallyl ether, Papulacandin B-10,12-di-(3-iodopropyl) ether and Papulacandin 12-mono-(3-iodopropyl) ether, Papulacandin B-10,12-di-(2-oxo-propyl) ether and Papulacandin B-12-mono-(2-oxo-propyl) ether, Papulacandin B-10,12-di-(methoxycarbonylmethyl) ether and Papulacandin B-12-mono-(methoxycarbonylmethyl) ether, Papulacandin B-10,12-dibenzylether and Papulacandin B-12-mono-benzyl ether, Papulacandin B-di-(p-nitrobenzyloxycarbonylmethyl) ether and Papulacandin B-12-mono-(p-nitrobenzyloxycarbonylmethyl ether, Papulacandin B-12-mono-(carboxymethyl) ether and Papulacandin B-10,12-di-(carboxymethyl) ether, and Papulacandin B-12-mono-p-nitrobenzylether and Papulacandin-B-10,12-di-p-nitrobenzyl ether.
- 12. A claim as claimed in claim 1 which is a member selected from the group consisting of Papulacandin B-10-carboxylmethyl ether, Papulacandin B-10-(methoxycarbonylmethyl) ether, Papulacandin B-10-(ethoxycarbonyl-methyl) ether, Papulacandin 10-(2-hydroxyethoxycarbonylmethyl) ether, Papulacandin B-10-(2,3-dihydroxypropyloxycarbonylmethyl) ether, Papulacandin B-10-(carbamoylmethyl) ether, Papulacandin B-10-(N-mono- or dialkylcarbamoylmethyl) ether, wherein alkyl is methyl or ethyl, Papulacandin B-10-(N-hydroxyethylcarbamoylmethyl) ether, Papulacandin B-10-(2-oxopropyl) ether, Papulacandin B-10(2-thienylcarbonylmethyl) ether, Papulacandin A-10,12-di-(p-nitrobenzyl) ether and Papulacandin A-12-Mono-p-nitrobenzyl ether, and Papulacandin A-10-carboxymethyl ether.
- 13. A pharmaceutical preparation which contains a compound as claimed in claim 1 together with a suitable pharmaceutical carrier.
Priority Claims (1)
Number |
Date |
Country |
Kind |
75760 |
Sep 1976 |
LUX |
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Parent Case Info
This is a continuation of application Ser. No. 830,503 filed on Sept. 6, 1977, now abandoned.
US Referenced Citations (8)
Continuations (1)
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Number |
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Parent |
830503 |
Sep 1977 |
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