US4732998A
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Bisphosphonic acids and esters
Assignee: Leo Pharma AS
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Filing: 1985-07-25
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Granted: 1988-03-22
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Expires: 2005-07-25
Abstract
Abstract PCT No. PCT/DK85/00071 Sec. 371 Date Mar. 31, 1986 Sec. 102(e) Date Mar. 31, 1986 PCT Filed Jul. 25, 1985 PCT Pub. No. WO86/00902 PCT Pub. Date Feb. 13, 1986.The present invention relates to hitherto unknown compounds of the formula I <IMAGE> (I) in which R1 is a straight or branched, saturated or unsaturated aliphatic or alicyclic C1-C10 hydrocarbon radical, an aryl or an aryl-C1-C4-alkyl radical, R1 if desired being unsubstituted or substituted with straight or branched C1-C4-alkyl, amino, C1-C4-alkamino, di-(C1-C4-alkyl)-amino, carboxy, C1-C4-alkoxycarbonyl, hydroxy, C1-C4-alkoxy, phenoxy, mercapto, C1-C4-alkylthio, phenylthio, halogen, trifluoromethyl; R2 stands for hydrogen, C1-C8-alkyl, aryl-C1-C4-alkyl or halogen; X is O or S, and n is an integer from 0 to 2; with the proviso that R2 cannot be hydrogen or methyl if n=O and R1 is methyl. The compounds of the invention are valuable in the human and veterinary practice.
Inventors
- 👤 Ernst T. Binderup
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 00:53
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3839; C07F9/386; A; A61; A61P; A61P3/00; A61P3/02; A61P3/12; A61P3/14; A61P43/00
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
169 words
A compound of formula I ##STR5## in which R 1 is a straight or branched, saturated or unsaturated aliphatic or alicyclic C 1 -C 10 hydrocarbon radical, an aryl or an aryl-C 1 -C 4 -alkyl radical, R 1 if desired being unsubstituted or substituted with straight or branched C 1 -C 4 -alkyl, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)-amino, carboxy, C 1 -C 4 -alkoxycarbonyl, hydroxy, C 1 -C 4 -alkoxy, phenoxy, mercapto, C 1 -C 4 -alkylthio, phenylthio, halogen, trifluoromethyl; R 2 stands for hydrogen, C 1 -C 8 -alkyl, aryl-C 1 -C 4 -alkyl or halogen; X is O or S, and n is an integer from 0 to 2; with the provisos that R 2 cannot be hydrogen or methyl if n=O and R 1 is methyl and that R 2 cannot be hydrogen or methyl if n=O and R 1 is unsubstituted n-butyl, n-pentyl or n-hexyl; and pharmaceutically acceptable, non-toxic salts and in the body easily hydrolyzable esters thereof.
Claim 2
Dependent Claim
169 words
A compound of formula I ##STR5## in which R 1 is a straight or branched, saturated or unsaturated aliphatic or alicyclic C 1 -C 10 hydrocarbon radical, an aryl or an aryl-C 1 -C 4 -alkyl radical, R 1 if desired being unsubstituted or substituted with straight or branched C 1 -C 4 -alkyl, amino, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)-amino, carboxy, C 1 -C 4 -alkoxycarbonyl, hydroxy, C 1 -C 4 -alkoxy, phenoxy, mercapto, C 1 -C 4 -alkylthio, phenylthio, halogen, trifluoromethyl; R 2 stands for hydrogen, C 1 -C 8 -alkyl, aryl-C 1 -C 4 -alkyl or halogen; X is O or S, and n is an integer from 0 to 2; with the provisos that R 2 cannot be hydrogen or methyl if n=O and R 1 is methyl and that R 2 cannot be hydrogen or methyl if n=O and R 1 is unsubstituted n-butyl, n-pentyl or n-hexyl; and pharmaceutically acceptable, non-toxic salts and in the body easily hydrolyzable esters thereof.
Claim 3
Dependent Claim
68 words
A compound according to claim 1, in which R 1 stands for straight or branched C 3 -C 6 -alkyl, phenyl or benzyl optionally substituted with amino, hydroxy, methyl or halogen, and R 2 for hydrogen, straight or branched C 1 -C 4 alkyl, benzyl or halogen; preferably R 1 being propyl, butyl, aminopropyl, aminobutyl, 2,2,2-trifluoroethyl, phenyl, or tolyl, and R 2 being hydrogen, methyl, ethyl or chlorine.
Claim 4
Dependent Claim
46 words
A mono-, di-, tri- or tetrabasic salt of a compound of formula I of claim 1, which is a salt selected from the group consisting of alkali metal salts, alkaline earth metal salts, salts with ammonia, lower alkylamines, lower alkanolamines, procaine, cycloalkylamines, benzylamines, and heterocyclic amines.
Claim 5
Dependent Claim
91 words
A mono-, di-, tri- or tetra ester of a compound of formula I of claim 1, which is an in vivo easily hydrolyzable ester, the ester forming residue being selected from the group consisting of alkanoyloxymethyl of three to six carbon atoms, 1-(alkanoyloxy)ethyl of four to seven carbon atoms, 1-methyl-1-(alkanoyloxy)ethyl of five to eight carbon atoms, alkoxycarbonyloxymethyl of three to six carbon atoms, 1-(alkoxycarbonyloxy)ethyl of four to seven carbon atoms, 1-methyl-1-(alkoxycarbonyloxy)ethyl of five to eight carbon atoms, 3-phthalidyl, 4-crotonolactonyl, γ-butyrolacton-4-yl, (2-oxo-1,3-dioxolen-4-yl)methyl, (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl, and (5-phenyl-2-oxo-1,3-dioxolen-4-yl)methyl as well as dialkylaminoalkyl, acetonyl, and methoxymethyl.
Claim 6
Dependent Claim
21 words
An ester according to claim 4, which is an alkanoyloxyalkyl or alkoxycarbonyloxy alkyl ester, in particular a pivaloyloxymethyl or ethoxycarbonyloxyethyl ester.
Claim 7
Dependent Claim
7 words
(Phenoxymethylene)-bisphosphonic acid and its salts and esters.
Claim 8
Dependent Claim
7 words
(Phenoxymethylene)-bisphosphonic acid and its salts and esters.
Claim 9
Dependent Claim
7 words
(2,2,2-Trifluoroethoxymethylene)-bisphosphonic acid and its salts and esters.
Claim 10
Dependent Claim
7 words
(2,2,2-Trifluoroethoxymethylene)-bisphosphonic acid and its salts and esters.
Claim 11
Dependent Claim
7 words
(4-Tolyloxymethylene)-bisphosphonic acid and its salts and esters.
Claim 12
Dependent Claim
7 words
(4-Tolyloxymethylene)-bisphosphonic acid and its salts and esters.
Claim 13
Dependent Claim
7 words
(n-Propoxymethylene)-bisphosphonic acid and its salts and esters.
Claim 14
Dependent Claim
7 words
(n-Propoxymethylene)-bisphosphonic acid and its salts and esters.
Claim 15
Dependent Claim
7 words
(4-Hydroxyphenoxymethylene)-bisphosphonic acid and its salts and esters.
Claim 16
Dependent Claim
7 words
(4-Hydroxyphenoxymethylene)-bisphosphonic acid and its salts and esters.
References Cited (Backward Citations)
SU772152A1
Cited
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