Abstract: The instant invention provides compounds of formula I wherein R1 is OH, O—C(O)—(C1-C6 alkyl), O—C(O)—O(C1-C6 alkyl), O—C(O)—Ar, or O—C(O)—O—Ar; R2 is H, OH, O(C1-C6 alkyl), O—C(O)—(C1-C6 alkyl), O—C(O)—O(C1-C6 alkyl), O—C(O)—Ar, O—C(O)—O—Ar, O—SO2—(C4-C6 alkyl), chloro, fluoro, or bromo; V is S, O, or CH2CH2; W is CHOH, C(O), or CH2; X is (CH2)n; R3 and R4 each, independently, are H, C1-C6 alkyl, C(O)—(C1-C6 alkyl), C(O)—NH—(C1-C6 alkyl), C(O)—Ar, or together with the nitrogen to which they are attached form a 5- or 6-membered imide or cyclic amide; n is 1, 2, or 3; and Ar is optionally substituted phenyl; povided that at least one of R3 and R4 contains a carbonyl functional group, and their use in the treatment of estrogen deficiency pathologies.

Abstract: The invention is a process for preparing a compound of formula Ia comprising reducing the compound of formula IIId wherein R3 is 1-piperidinyl, 1-pyrrolidinyl, dimethylamino, diethylamino or 1-hexamethyleneimino, R1a, R1b, R2a, R2b, and n are as defined in the specification, with a reducing agent in the presence of a solvent, heating to reflux.

Abstract: The present invention provides a compound of formula I wherein R1 is —H, —OH, —O(C1-C4 alkyl) , —OCOC6H5, —OCO(C1-C6 alkyl), or —OSO2 (C4-C6 alkyl); R2 is —H, —OH, —O(C1-C4 alkyl), —OCOC6H5, —OCO(C1-C6 alkyl) or —OSO2 (C4-C6 alkyl); n is 2 or 3; and R3 is 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, dimethylamino, diethylamino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof. Compounds of formula I are useful in treating osteoporosis, cardiovascular related pathological conditions, and estrogen-dependent cancer.

Abstract: The present invention provides novel compound of the formula: wherein Ra is —OH or —O—(C1-C4 alkyl); R1a is —OH or —O—(C1-C4 alkyl); n is 2 or 3; R2 and R3 are each independently: —C1-C4 alkyl, or combine to form 1-piperidinyl, 1-pyrrolidinyl, 1-pyrrolidinyl substituted with one or two methyl groups, 4-morpholino or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof.

Abstract: The present invention provides a plasticizer compound having the general formula: in which n=1 to 3, R represents a C2-C8 straight or branched aliphatic hydrocarbon chain or C6-C10 aromatic or cycloaliphatic group, and R′ and R″ are each independently a branched oxyalkylene chain represented by the chemical formula C8H16O and by the chemical structures: The present invention is also directed to a coverstock formulation comprising the above-plasticizer compound.

Abstract: The present invention provides method of treating endometriosis using novel benzothiophene compounds of formula I wherein R is —H, —OH, —O(C1-C4 alkyl), —O—CO—(C1-C6 alkyl), —O—CO—Ar in which Ar is optionally substituted phenyl, or —O—SO2—(C4-C6 alkyl); R1 is —H, —OH, —O(C1-C4 alkyl),, —O—CO—(C1-C6 alkyl), —O—CO—Ar in which Ar is optionally substituted phenyl, —O—SO2—(C4-C6 alkyl) chloro or bromo; R2 is —H or —OH; n is 2 or 3; and R3 and R4 each are independently C1-C4 alkyl, or combine to form 1-piperidinyl, 1-pyrrolidinyl, methyl-1-pyrrolidinyl, dimethyl-1-pyrrolidinyl, 4-morpholino, or 1-hexamethyleneimino; or a pharmaceutically acceptable salt thereof.

Abstract: The present invention provides a compound of formula I wherein R1 is H, OH, halo, OCO(C1-C6 alkyl), OCO(aryl), OSO2(C4-C6 alkyl), OCOO(C1-C6 alkyl), OCOO(aryl), OCONH(C1-C6 alkyl), or OCON(C1-C6 alkyl)2; R2 is aryl, C1-C6 alkyl, C3-C6 cycloalkyl, or 4-cyclohexanol; R3 is O(CH2)2 or O(CH2)3; R4 and R5 are optionally CO(CH2)3, CO(CH2)4, C1-C6 alkyl, or R4 and R5 combine to form, with the nitrogen to which they are attached, piperidine, morpholine, pyrrolidine, 3-methylpyrrolidine, 3,3-dimethylpyrrolidine, 3,4-dimethylpyrrolidine, azepine, or pipecoline; R6 is and pharmaceutically acceptable salts thereof; useful in treating estrogen deficient pathology.

Abstract: The present invention provides a compound of formula I wherein R1 is H, OH, halo, OCO(C1-C6 alkyl), OCO(aryl), OSO2(C4-C6 alkyl), OCOO(C1-C6 alkyl), OCOO(aryl), OCONH(C1-C6 alkyl), or OCON(C1-C6 alkyl)2; R2 is aryl, C1-C6 alkyl, C3-C6 cycloalkyl, or 4-cyclohexanol; R3 is O(CH2)2 or O(CH2)3; R4 and R5 are optionally CO(CH2)2CH3, CO(CH2)3CH3, C1-C6 alkyl, or R4 and R5 combine to form, with the nitrogen to which they are attached, piperidine, morpholine, pyrrolidine, 3-methylpyrrolidine, 3,3-dimethylpyrrolidine, 3,4-dimethylpyrrolidine, azepine, or pipecoline; and pharmaceutically acceptable salts thereof. The invention further provides pharmaceutical compositions containing compounds of formula I and methods of use for the compounds of formula I.

Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino; or a pharmaceutically acceptable salt thereof.

Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino; or a pharmaceutically acceptable salt thereof.

Abstract: This invention relates to the fields of pharmaceutical and organic chemistry and provides novel phosphorous-containing benzothiophene compounds which are useful for the treatment of the various medical indications associated with post-menopausal syndrome, as well as estrogen dependent diseases including cancer of the breast, uterus and cervix. The present invention further relates to intermediate compounds and processes useful for preparing the pharmaceutically active compounds of the present invention, and pharmaceutical compositions.

Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino;or a pharmaceutically acceptable salt thereof.

Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino; or a pharmaceutically acceptable salt thereof.

Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino;or a pharmaceutically acceptable salt thereof.

Abstract: A method of inhibiting ovarian dysgenesis, delayed puberty, or sexual infantilism comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.

Abstract: The present invention provides novel methods of lowering serum cholesterol and inhibiting smoother muscle cell proliferation, particularly restenosis, in humans, and inhibiting uterine fibroid disease and endometriosis in women comprising administering to a human/woman in need of treatment an effective amount of a compound of formula I ##STR1## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, halo, or trifluoromethyl;R.sup.1 and R.sup.2 each are the same or different C.sub.1 -C.sub.6 alkyl group;n is an integer from 2 to 6; andR.sup.3 and R.sup.4 each are independently C.sub.1 -C.sub.4 alkyl, or combine to form a substituent selected from the group consisting of pyrrolidino, morpholino, piperidino, piperazino, 4-(C.sub.1 -C.sub.6 alkyl)piperazino, and 4-phenyl-piperazino; or a pharmaceutically acceptable salt thereof.

Abstract: The present invention provides a novel process for preparing a compound of formula I ##STR1## wherein R.sup.1 and R.sup.2 combine to form C.sub.4 -C.sub.6 polymethylene, --CH.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.2 --, --CH.sub.2 C(CH.sub.3).sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; or a pharmaceutically acceptable salt or solvate thereof.Also provided intermediates of formulae II and IV ##STR2## wherein Z is a leaving group.

Abstract: A method of inhibiting ovarian dysgenesis, delayed puberty, or sexual infantilism comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.

Abstract: Viridin, viridiol, demethoxyviridin, demethoxyviridiol, virone, and wortmannolone, and analogs thereof, are inhibitors of phosphatidylinositol 3-kinase. The compounds are particularly useful for inhibiting phosphatidylinositol 3-kinase in vertebrates and for treating phosphatidylinositol 3-kinase-dependent conditions, especially neoplasms, restenosis and atherosclerosis, and bone disorders in vertebrates.

Abstract: A method of inhibiting ovarian dysgenesis, delayed puberty, or sexual infantilism comprising administering to a human in need thereof an effective amount of a compound having the formula ##STR1## wherein R.sup.1 and R.sup.3 are independently hydrogen, --CH.sub.3, ##STR2## wherein Ar is optionally substituted phenyl; R.sup.2 is selected from the group consisting of pyrrolidine, hexamethyleneamino, and piperidino; or a pharmaceutically acceptable salt of solvate thereof.