Phosphonosuccinic acid derivatives, processes for their preparat

Details Phosphonosuccinic acid derivatives, processes for their preparat Phosphonosuccinic acid derivatives, processes for their preparat

1994-06-03

1996-07-23

Gupta, Yogendra N.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Phosphorus containing other than solely as part of an...

514 75, 514553, 558 87, 558141, 558169, 560 11, A61K 3166, C07C22924

Patent

active

055389570

DESCRIPTION:

BRIEF SUMMARY
The present invention concerns new phosphonosuccinic acid derivatives, processes for their operation, as well as medicaments which contain these substances.
In Phosphorus and Sulphur 13, 85 (1982) is described the synthesis of 3-dimethylamino-2-dimethylphosphonosuccinic acid dimethyl ester but a pharmacological action of this compound is not known.
It has now been found that analogous phosphonosuccinic acid derivatives display an excellent action on the calcium metabolism and thus are suitable for the broad treatment of calcium metabolism disturbances. In particular, they can be very well used there where the bone build up and breakdown is disturbed, i.e. they are suitable for the treatment of diseases of the skeletal system, such as e.g. osteoporosis, Paget's disease, Bechterev's disease and the like.
However, on the basis of these properties, they can also find use for the therapy of urolithiasis and for the prevention of heterotopic ossifications. Furthermore, due to their influencing of the calcium metabolism, they also form a basis for the treatment of rheumatoid arthritis, of osteoarthritis and of degenerative arthrosis.
The subject of the present invention are compounds of the general formula I, ##STR2## in which R signifies a possibly substituted amino group of the general formula --NR.sup.1 R.sup.2, whereby, independently of one another, R.sup.1 and R.sup.2 each signify hydrogen, lower alkyl, lower alkenyl or lower alkynyl or R represents a saturated, unsaturated or aromatic heterocyclic ring which can possibly be substituted once or twice by lower alkyl or halogen, alk signifies a valency bond, a methylene, a saturated or unsaturated, straight-chained or branched alkylene chain with 2-6 carbon atom and R.sup.3, R.sup.4, R.sup.5, in each case independently of one another, signify hydrogen, lower alkyl or benzyl, as well as their pharmacologically acceptably salts, whereby, for the case that R.sup.3 .dbd.R.sup.4 .dbd.R.sup.5 .dbd.CH.sub.3 and alk signifies a valency bond, R cannot be the dimethylamino group.
In all cases, lower alkyl is to represent a straight-chained or branched .sub.1 -C.sub.6 -alkyl group, such as e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl or hexyl radical, especially methyl, ethyl, propyl, isobutyl or pentyl.
Lower alkenyl signifies unsaturated radicals with 3-6 carbon atoms, such as e.g. allyl, but 2-enyl, hexa-2,4-dienyl, above all allyl.
Lower alkynyl is to represent unsaturated radicals with 3-6 carbon atoms, such as e.g. propargyl, but-3-ynyl, hex-5-ynyl but especially propargyl.
If the radical R signifies a saturated heterocyclic ring, it is a question of 3-8 membered rings which can also contain one or two further heteroactoms, such as the aziridine, azetidine, pyrrolidine, piperidine, azepine, morpholine or the thiomorpholine ring, especially the pyrrolidine, azepine and the morpholine ring.
If R signifies an unsaturated heterocyclic ring, as a rule it is a question of the imidazoline ring.
If R represents a hetero-aromatic ring, it is a question of a five- or six-membered ring, such as the pyridine, pyrimidine, pyrazine, imidazole, especially the pyridine and imidazole ring.
The heterocyclic rings can possibly by substituted once or twice by C.sub.1 -C.sub.6 -alkyl groups, preferably the methyl, ethyl or isopropyl group, as well as by chlorine or bromine.
In the case of the saturated or unsaturated, straight-chained or branched alkylene chains, alk represents radicals such as e.g. methylene, ethylene, propylene, butylene, 2-methylpropylene, pentylene, 1,1-dimethylpropylene, 2,3-dimethylpropylene, 2,2-dimethylpropylene, 2-methylbutylene, hexylene, 2,3-dimethylbutylene, 2-methylpentylene, 2-butenylene, 2-butynylene, especially methylene, ethylene, propylene, butylene, 2-methylpropylene, pentylene, hexylene and 2-butenylene.
Compounds of general formula I contain at least two assymmetric carbon atoms, therefore optically-active compounds of the general formula I are also the subject of the present invention.
Compounds of general formula I are prepared

REFERENCES:
patent: 3962433 (1976-06-01), Worms et al.
CA97:216314, 1982.

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