Salts of physiologically active and psychoactive alkaloids and amines simultaneously exhibiting bioavailability and abuse resistance
First Claim
Patent Images
1. A drug substance comprising a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound useful for the treatment of an ailment by therapeutic administration and exhibiting anti-abuse properties when employed in non-therapeutic administration.
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Abstract
Drug substances comprising a pharmaceutically acceptable organic acid addition salt 6f amine containing pharmaceutically active compounds useful for the treatment of a therapeutic ailment administration and exhibiting prophylactic properties when employed in non-therapeutic administration.
28 Citations
515 Claims
- 1. A drug substance comprising a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound useful for the treatment of an ailment by therapeutic administration and exhibiting anti-abuse properties when employed in non-therapeutic administration.
- 29. A drug substance as a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound exhibiting at least two dissolution profiles one of which provides for drug efficacy when administered in a formulated oral dosage and one which does not provide drug efficacy when administered as a non-oral dosage.
- 52. A drug substance comprising an organic acid addition salt of an amine containing pharmaceutically active compound used to treat a combination of two or more therapeutic ailments, at least one of which is drug abuse.
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75-288. -288. (canceled)
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289. An organic acid addition salt of amine-containing pharmaceutically active compounds wherein the organic acid comprises a compound of Formula A:
wherein R1-R4 are independently selected from H, alkyl of 1-6 carbons, adjacent groups may be taken together to form a cyclic alkyl, cyclic alkyl-aryl or cyclic aryl moiety; R5 is selected from H, or an alkali earth cation; R6 is selected from H, alkyl of 1-6 carbons, an alkali earth cation, and aryl of 6 to 12 carbons, in a number sufficient to complete the valence bonding of X, and wherein X is selected from nitrogen, oxygen or sulfur.
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290-309. -309. (canceled)
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310. Organic acid addition salts of amine containing pharmaceutically active compounds selected for their targeted release characteristic in the gastro intestinal tract and bio-unavailability in mucosal membranes, and formulated into a drug product wherein said amine containing pharmaceutically active compounds can not be directly isolated.
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311-336. -336. (canceled)
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337. A tamper resistant oral dosage drug product comprising an organic acid salt of an amine-containing pharmaceutically active compound formulated wherein said organic acid and said amine-containing pharmaceutically active compound can not be directly isolated.
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338-381. -381. (canceled)
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382. A pharmaceutically active compound comprising the organic acid addition salt of an amine-containing pharmaceutically active material wherein said compound is essentially bio-unavailable when exposed to mucosal membranes and exhibits recovery from aqueous solution at pH 4.5 of at least 85 weight percent.
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383-403. -403. (canceled)
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404. A pharmaceutically active compound comprising the organic acid addition salt of an amine-containing pharmaceutically active material wherein said compound is essentially bio-unavailable when exposed to human mucosal membranes and exhibits recovery from aqueous solution at pH 7.0 of at least 85 weight percent.
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405-427. -427. (canceled)
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428. A pharmaceutically active compound comprising an organic acid addition salt of an amine-containing pharmaceutically active compound wherein said compound is essentially bio-unavailable when exposed to mucosal membranes unless processed by the steps of:
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a) dissolution in an aqueous solution of pH greater than 8; b) extraction of the active pharmaceutical ingredient into a water immiscible solvent; c) separation of the aqueous layer from the solvent; d) washing of the solvent layer with an aqueous solution of pH greater than 8; and e) drying the solvent layer to remove traces of water.
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429-455. -455. (canceled)
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456. A pharmaceutically active compound comprising an organic acid addition salt of an amine-containing pharmaceutically active compound wherein said compound is essentially bio-unavailable when exposed to mucosal membranes unless processed by the steps of:
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a. dissolution in an aqueous solution of pH greater than about 1; b. filtration of the precipitated organic acid; c. adjustment of the filtrate to a pH of about 8; d. addition of a water immiscible solvent in which the pharmaceutically active compound is soluble; e. separation of the aqueous layer from the solvent; f. washing of the solvent layer with an aqueous solution of pH greater than 8; and g. drying the solvent layer to remove traces of water.
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457-507. -507. (canceled)
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508. A drug substance comprising a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound useful for the treatment of a therapeutic ailment administration and exhibiting anti-abuse properties when employed in non-therapeutic administration wherein said pharmaceutically active compound comprises a material selected from acetaminophen, caffeine, acetorphine, acetylmethadol, allylprodine, alphacetylmethadol, bufotenine, dextromoramide, diethyltryptamine, etorphine, heroin, ibogaine, ketobemidone, lysergic acid diethylamide, mescaline, methaqualone, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, N-ethyl-1-phenylcyclohexylamine, peyote, 1-(1-phenylcyclohexyl)pyrrolidine, psilocybin, psilocin, 1 -{1-(2-thienyl)-cyclohexyl}-piperidine, alphaprodine, anileridine, cocaine, dextropropoxyphene, diphenoxylate, ethylmorphine, glutethimide, hydrocodone, hydromorphone, levo-alphaacetylmethadol, levorphanol, meperidine, methadone, morphine, opium, oxycodone, oxymorphone, poppy straw, thebaine, amphetamine, methamphetamine, methylphenidate, phencyclidine, codeine, benzphetamine, ketamine, alprazolam, chlorodiazepoxide, clorazepate, diethylpropion, fenfluramine, flurazepam, halazepam, lorazepam, mazindol, mebutamate, midazolam, oxazepam, pemoline, pentazocine, phentermine, prazepam, quazepam, temazepam, triazolam, zolpidem, and buprenorphine and wherein said organic acid addition salt comprises a material selected from the group consisting of pamoic acid, disodium pamoate, di-ammonium pamoate, di-potassium pamoate, lower molecular weight di-alkyl amine pamoate, lower molecular weight di-aryl amine pamoate, lower molecular weight di-alkyl esters of pamoic acid, lower molecular weight di-aryl esters of pamoic acid, lower molecular weight di-alkylacyl O-esters of pamoic acid and lower molecular weight di-arylacyl O-esters of pamoic acid.
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510. A drug substance comprising a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound useful for the treatment of an ailment by therapeutic administration and exhibiting anti-abuse properties when employed in non-therapeutic administration;
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wherein said non-therapeutic administration is selected from mucosal membrane bio-unavailability, non-permeability in mucosal membranes, essentially no dissolution in the mucosal membranes, non-efficacy for mucosal membranes and non-release properties when delivered to mucosal membranes; wherein said pharmaceutically active compound comprises a material selected from acetaminophen, caffeine, acetorphine, acetylmethadol, allylprodine, alphacetylmethadol, bufotenine, dextromoramide, diethyltryptamine, etorphine, heroin, ibogaine, ketobemidone, lysergic acid diethylamide, mescaline, methaqualone, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, N-ethyl-1-phenylcyclohexylamine, peyote, 1-(1-phenylcyclohexyl)pyrrolidine, psilocybin, psilocin, 1-{1-(2-thienyl)-cyclohexyl}-piperidine, alphaprodine, anileridine, cocaine, dextropropoxyphene, diphenoxylate, ethylmorphine, glutethimide, hydrocodone, hydromorphone, levo-alphaacetylmethadol, levorphanol, meperidine, methadone, morphine, opium, oxycodone, oxymorphone, poppy straw, thebaine, amphetamine, methamphetamine, methylphenidate, phencyclidine, codeine, benzphetamine, ketamine, alprazolam, chlorodiazepoxide, clorazepate, diethylpropion, fenfluramine, flurazepam, halazepam, lorazepam, mazindol, mebutamate, midazolam, oxazepam, pemoline, pentazocine, phentermine, prazepam, quazepam, temazepam, triazolam, zolpidem, imipramine and buprenorphine; and wherein said organic acid comprises a material selected from the group consisting of pamoic acid, disodium pamoate, di-ammonium pamoate, di-potassium pamoate, lower molecular weight di-alkyl amine pamoate, lower molecular weight di-aryl amine pamoate, lower molecular weight di-alkyl esters of pamoic acid, lower molecular weight di-aryl esters of pamoic acid, lower molecular weight di-alkylacyl O-esters of pamoic acid and lower molecular weight di-arylacyl O-esters of pamoic acid. - View Dependent Claims (511, 512)
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513. A drug substance comprising a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound useful for the treatment of an ailment by therapeutic administration and exhibiting anti-abuse properties when employed in non-therapeutic administration;
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wherein said non-therapeutic administration is selected from mucosal membrane bio-unavailability, non-permeability in mucosal membranes, essentially no dissolution in the mucosal membranes, non-efficacy for mucosal membranes and non-release properties when delivered to mucosal membranes; wherein said pharmaceutically active compound comprises a material selected from acetaminophen, caffeine, acetorphine, acetylmethadol, allylprodine, alphacetylmethadol, bufotenine, dextromoramide, diethyltryptamine, etorphine, heroin, ibogaine, ketobemidone, lysergic acid diethylamide, mescaline, methaqualone, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, N-ethyl-1-phenylcyclohexylamine, peyote, 1-(1-phenylcyclohexyl)pyrrolidine, psilocybin, psilocin, 1-{1-(2-thienyl)-cyclohexyl}-piperidine, alphaprodine, anileridine, cocaine, dextropropoxyphene, diphenoxylate, ethylmorphine, glutethimide, hydrocodone, hydromorphone, levo-alphaacetylmethadol, levorphanol, meperidine, methadone, morphine, opium, oxymorphone, poppy straw, thebaine, amphetamine, methamphetamine, methylphenidate, phencyclidine, codeine, benzphetamine, ketamine, alprazolam, chlorodiazepoxide, clorazepate, diethylpropion, fenfluramine, flurazepam, halazepam, lorazepam, mazindol, mebutamate, midazolam, oxazepam, pemoline, pentazocine, phentermine, prazepam, quazepam, temazepam, triazolam, zolpidem, imipramine and buprenorphine; and wherein said organic acid comprises a material selected from the group consisting of pamoic acid, disodium pamoate, di-ammonium pamoate, di-potassium pamoate, lower molecular weight di-alkyl amine pamoate, lower molecular weight di-aryl amine pamoate, lower molecular weight di-alkyl esters of pamoic acid, lower molecular weight di-aryl esters of pamoic acid, lower molecular weight di-alkylacyl O-esters of pamoic acid and lower molecular weight di-arylacyl O-esters of pamoic acid.
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514. A drug substance comprising a pharmaceutically acceptable organic acid addition salt of an amine containing pharmaceutically active compound useful for the treatment of an ailment by therapeutic administration and exhibiting anti-abuse properties when employed in non-therapeutic administration;
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wherein said non-therapeutic administration is selected from mucosal membrane bio-unavailability, non-permeability in mucosal membranes, essentially no dissolution in the mucosal membranes, non-efficacy for mucosal membranes and non-release properties when delivered to mucosal membranes; wherein said pharmaceutically active compound comprises a material selected from acetaminophen, caffeine, acetorphine, acetylmethadol, allylprodine, alphacetylmethadol, bufotenine, dextromoramide, diethyltryptamine, etorphine, heroin, ibogaine, ketobemidone, lysergic acid diethylamide, mescaline, methaqualone, 3,4-methylenedioxyamphetamine, 3,4-methylenedioxymethamphetamine, N-ethyl-1-phenylcyclohexylamine, peyote, 1-(1-phenylcyclohexyl)pyrrolidine, psilocybin, psilocin, 1-{1-(2-thienyl)-cyclohexyl}-piperidine, alphaprodine, anileridine, cocaine, dextropropoxyphene, diphenoxylate, ethylmorphine, glutethimide, hydrocodone, hydromorphone, levo-alphaacetylmethadol, levorphanol, meperidine, methadone, morphine, opium, oxycodone, oxymorphone, poppy straw, thebaine, amphetamine, methamphetamine, methylphenidate, phencyclidine, codeine, benzphetamine, ketamine, alprazolam, chlorodiazepoxide, clorazepate, diethylpropion, fenfluramine, flurazepam, halazepam, lorazepam, mazindol, mebutamate, midazolam, oxazepam, pemoline, pentazocine, phentermine, prazepam, quazepam, temazepam, triazolam, zolpidem, imipramine and buprenorphine; and wherein said organic acid comprises a material selected from the group consisting of disodium pamoate, di-ammonium pamoate, di-potassium pamoate, lower molecular weight di-alkyl amine pamoate, lower molecular weight di-aryl amine pamoate, lower molecular weight di-alkyl esters of pamoic acid, lower molecular weight di-aryl esters of pamoic acid, lower molecular weight di-alkylacyl O-esters of pamoic acid and lower molecular weight di-arylacyl O-esters of pamoic acid.
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Specification