Claims
- 1. A 17-(4-pyridazinyl)-5.beta.,14.beta.-androstane derivative of formula (I): ##STR4## wherein: the symbol means that the substituents in position 17 can have an .alpha. or .beta. configuration;
- the symbol --- represents a single or double bond;
- Y is oxygen or guanidinoimino, when --- in position 3 is a double bond;
- Y is hydroxyl, OR.sup.4 or SR.sup.4, when --- in position 3 is a single bond and can have an .alpha. or .beta. configuration;
- R is an unsubstituted or substituted 4-pyridazinyl group;
- R.sup.1 is hydrogen; methyl; ethyl or n-propyl substituted by OH or NR.sup.5 R.sup.6 ;
- R.sup.2 is hydrogen or together to R.sup.3 is a bond of an oxirane ring;
- R.sup.3 is hydrogen or together to R.sup.2 is a bond of an oxirane ring;
- R.sup.4 is hydrogen; methyl; C.sub.2 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 acyl, these alkyl, alkenyl and acyl groups being unsubstituted or substituted by a quaternary ammonium group or one or more OR.sup.7, NR.sup.8 R.sup.9, formyl, amidino, guanidinoimino or by NR.sup.8 R.sup.9 and hydroxy;
- R.sup.5, R.sup.6 are independently hydrogen; methyl; C.sub.2 -C.sub.6 alkyl unsubstituted or substituted by one NR.sup.10 R.sup.11, or NR.sup.10 R.sup.11 and hydroxy, or R.sup.5 and R.sup.6 taken together with the nitrogen atom form an unsubstituted or substituted saturated or unsaturated penta- or hexa-monoheterocyclic ring, optionally containing another heteroatom chosen from oxygen or sulfur or nitrogen;
- R.sup.7 is hydrogen, methyl or C.sub.2 -C.sub.4 alkyl, this alkyl being unsubstituted or substituted by one or more NR.sup.10 R.sup.11 or by NR.sup.10 R.sup.11 and hydroxy;
- R.sup.8, R.sup.9 are independently hydrogen; methyl; C.sub.2 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl, these alkyl and alkenyl groups being unsubstituted or substituted by one or more NR.sup.10 R.sup.11, or NR.sup.10 R.sup.11 and hydroxy, or R.sup.8 and R.sup.9 taken together with the nitrogen atom form an unsubstituted or substituted saturated or unsaturated penta- or hexa-monoheterocyclic ring, optionally containing another heteroatom chosen from oxygen or sulfur or nitrogen, or R.sup.8 is hydrogen and R.sup.9 is amidino;
- R.sup.10, R.sup.11 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, or R.sup.10 and R.sup.11, taken together with the nitrogen atom form a saturated or unsaturated penta- or hexa-monoheterocyclic ring, including all of the possible stereoisomers, in particular Z and E isomers, optical isomers and their mixtures and the metabolites and the metabolic precursors of the compounds of formula (I).
- 2. A 17-(4-pyridazinyl)-5.beta.,14.beta.-androstane derivative of formula (I): ##STR5## wherein: the symbol means that the substituents in position 17 can have an .alpha. or .beta. configuration;
- the symbol --- represents a single or double bond;
- Y is oxygen or guanidinoimino, when --- in position 3 is a double bond;
- Y is hydroxy, OR.sup.4 or SR.sup.4, when ---in position 3 is a single bond and can have an .alpha. or .beta. configuration;
- R is an unsubstituted or substituted 4-pyridazinyl group;
- R.sup.1 is hydrogen; methyl; ethyl or n-propyl substituted by OH or NR.sup.5 R.sup.6 ;
- R.sup.2 and R.sup.3 form an oxirane ring;
- R.sup.4 is hydrogen; methyl; C.sub.2 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 acyl, these alkyl, alkenyl and acyl groups being unsubstituted or substituted by a quaternary ammonium group or one or more OR.sup.7, NR.sup.8 R.sup.9, formyl, amidino, guanidinoimino or by NR.sup.8 R.sup.9 and hydroxy;
- R.sup.5, R.sup.6 are independently hydrogen; methyl; C.sub.2 -C.sub.6 alkyl unsubstituted or substituted by one NR.sup.10 R.sup.11, or NR.sup.10 R.sup.11 and hydroxy, or R.sup.5 and R.sup.6 taken together with the nitrogen atom form an unsubstituted or substituted saturated or unsaturated penta- or hexa-monoheterocyclic ring, optionally containing another heteroatom chosen from oxygen or sulfur or nitrogen;
- R.sup.7 is hydrogen, methyl or C.sub.2 -C.sub.4 alkyl, this alkyl being unsubstituted or substituted by one or more NR.sup.10 R.sup.11 or by NR.sup.10 R.sup.11 and hydroxy;
- R.sup.8, R.sup.9 are independently hydrogen; methyl; C.sub.2 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl, these alkyl and alkenyl groups being unsubstituted or substituted by one or more NR.sup.10 R.sup.11, or NR.sup.10 R.sup.11 and hydroxy, or R.sup.8 and R.sup.9 taken together with the nitrogen atom form an unsubstituted or substituted saturated or unsaturated penta- or hexa-monoheterocyclic ring, optionally containing another heteroatom chosen from oxygen or sulfur or nitrogen, or R.sup.8 is hydrogen and R.sup.9 is amidino;
- R.sup.10, R.sup.11 are independently hydrogen, C.sub.1 -C.sub.6 alkyl, or R.sup.10 and R.sup.11, taken together with the nitrogen atom form a saturated or unsaturated penta- or hexa-monoheterocyclic ring, including all of the possible stereoisomers, in particular Z and E isomers, optical isomers and their mixtures and the metabolites and the metabolic precursors of the compounds of formula (I).
- 3. The 17-(4-pyridazinyl)-5.beta.,14.beta.-androstane derivative of claim 1, in the form of it's Z and E isomers, tautomers, optical isomers or mixtures thereof, metabolites or the metabolic precursors or pharmaceutically acceptable salts thereof.
- 4. A pharmaceutical composition comprising the 17-(4-pyridazinyl)-5.beta.,14.beta.-androstane derivative of claim 1, with a pharmaceutically acceptable carrier, diluent or a mixture thereof.
- 5. The 17-(4-pyridazinyl)-5.beta.,14.beta.-androstane derivative of claim 2, in the form of it's Z and E isomers, tautomers, optical isomers or mixtures thereof, metabolites or the metabolic precursors or pharmaceutically acceptable salts thereof.
- 6. A pharmaceutical composition comprising the 17-(4-pyridazinyl)-5.beta.,14.beta.-androstane derivative of claim 2, with a pharmaceutically acceptable carrier, diluent or a mixture thereof.
- 7. A compound, which is selected from:
- .beta. -(2-Hydroxyethoxy)-17.beta.-(4-pyridazinyl)-5.beta.-androstane-14.beta.,17.alpha.-diol,
- 3.beta.-(3-Aminopropoxy)-17.beta.-(4-pyridazinyl)-5.beta.-androstane-14.beta.,17.alpha.-diol,
- 3.beta.-(2-(1-Pyrrolidinyl)ethoxy)-17.beta.-(4-pyridazinyl)-5.beta.-androstane-14.beta.,17.alpha.-diol,
- 3.beta.-(3-(1-Pyrrolidinyl)propoxy)-17.beta.-(4-pyridazinyl)-5.beta.-androstane-14.beta.,17.alpha.-diol,
- 17.beta.-(4-Pyridazinyl)-17.alpha.-(3-aminopropoxy)-5.beta.-androstane-3.beta.,14.beta.-diol,
- 3.beta.-(2-(1-Pyrrolidinyl)ethoxy)-17.beta.-(4-pyridazinyl)-17.alpha.-methoxy-5.beta.-androstan-14.beta.-ol,
- 3.beta.-(2-(1-Pyrrolidinyl)ethoxy)-17.beta.-(4-pyridazinyl)-17.alpha.-(3-aminopropoxy)-5.beta.-androstan-14.beta.-ol,
- 14.beta.,17.alpha.-Dihydroxy-17.beta.-(4-pyridazinyl)-5.beta.-androstan-3-one,
- 3-Guanidinoimino-17.beta.-(4-pyridazinyl)-5.beta.-androstane-14.beta.,17.alpha.-diol,
- 1.beta. . 15.beta.-Epoxy-17.beta.-(4-pyridazinyl)-5.beta.-androstane-3.beta.,17.alpha.-diol,
- 17.alpha.-(4-Pyridazinyl)-5.beta.-androstane-3.beta.,14.beta.,17.beta.-triol,
- 3.beta.-(2-(1-Pyrrolidinyl)ethoxy)-17.alpha.-(4-pyridazinyl)-5.beta.-androstane-14.beta.,17.beta.-diol,
- 3.beta.,17.beta.-Bis(2-(1-pyrrolidinyl)ethoxy)-17.alpha.-(4-pyridazinyl)-5.beta.-androstan-14.beta.-ol,
- and the 3.alpha. derivatives of the above identified 3.beta. derivatives and also the corresponding 3.alpha. and 3.beta. thioderivatives (Y=S).
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 42 27 616.0 |
Aug 1992 |
DEX |
|
Parent Case Info
This is a Division of application Ser. No. 08/106,893, filed on Aug. 16, 1993, pending.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
|
5432169 |
Quadri et al. |
Jul 1995 |
|
Divisions (1)
|
Number |
Date |
Country |
| Parent |
106893 |
Aug 1993 |
|
Patent Grant
5567697
