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Patent US6407105 - Compounds and methods for use thereof in the treatment of cancer or viral ... - Google PatentsSearch Images Maps Play YouTube News Gmail Drive More »Sign inPatentsBenzimidazole derivatives and salts and prodrugs thereof are disclosed, together with methods for the treatment of cancers or viral infections in warm blooded animals by administration of these compounds. Such compounds may be used in combination with a chemotherapeutic agent and/or a potentiator....http://www.google.com/patents/US6407105?utm_source=gb-gplus-sharePatent US6407105 - Compounds and methods for use thereof in the treatment of cancer or viral infectionsAdvanced Patent SearchPublication numberUS6407105 B1Publication typeGrantApplication numberUS 09/670,169Publication dateJun 18, 2002Filing dateSep 26, 2000Priority dateSep 26, 2000Fee statusLapsedPublication number09670169, 670169, US 6407105 B1, US 6407105B1, US-B1-6407105, US6407105 B1, US6407105B1InventorsJames C. Quada, Jr., Joseph K. Agyin, James Berger CamdenOriginal AssigneeThe Procter & Gamble CompanyExport CitationBiBTeX, EndNote, RefManPatent Citations (60), Non-Patent Citations (97), Referenced by (16), Classifications (14), Legal Events (8) External Links: USPTO, USPTO Assignment, EspacenetCompounds and methods for use thereof in the treatment of cancer or viral infections
US 6407105 B1Abstract
R is —COOR2; R2 is haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino. 2. A compound according to claim 1 having the following formula A-1: 3. A compound according to claim 2 wherein R2 is selected from the group consisting of substituted or unsubstituted benzyl.
R is —COOR2; R2 is haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino; and, a pharmaceutically acceptable carrier.
6. A unit dosage form comprising a compound of the following formula: wherein, R is —COOR2; R2 is haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino; and, a pharmaceutically acceptable carrier.
R is —COOR2; R2 is haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino; and, instruction for use in treating cancer or a viral infection.
R is —COOR2; R2 is haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino. 9. A prodrug of a compound of the following formula: wherein,
R is —COOR2 or —CONHR2; R2 is alkyl, haloalkyl, alkenyl, haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino. 10. A pharmaceutical composition comprising a therapeutically effective amount of a pharmaceutically acceptable salt of a compound of the following formula: wherein,
R is —COOR2 or —CONHR2; R2 is alkyl, haloalkyl, alkenyl, haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino; and, a pharmaceutically acceptable carrier.
R is —COOR2 or —CONHR2; R2 is alkyl, haloalkyl, alkenyl, haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino; and, a pharmaceutically acceptable carrier selected from the group consisting of a liposome delivery system, a soluble polymer to which said compound is coupled, and a biodegradable polymer to which said compound is coupled.
R is —COOR2 or —CONHR2; R2 is alkyl, haloalkyl, alkenyl, haloalkenyl, cycloalkyl, cycloalkalkyl, heterocycloalkyl, heterocycloalkalkyl, substituted or unsubstituted benzyl, hydroxyalkyl, alkoxyalkyl, poly(alkoxy)alkyl, hydroxyalkoxyalkyl, hydroxypoly(alkoxy)alkyl, haloalkoxyalkyl, halopoly(alkoxy)alkyl, or aminoalkyl; and each of X and Y is independently hydrogen, alkyl, alkenyl, cycloalkyl, haloalkyl, haloalkenyl, halogen, nitro, or amino; and, a pharmaceutically acceptable carrier;
The term “poly(alkoxy)alkyl” denotes 2 to 200, preferably 2 to 20, alkoxy groups covalently linked in either a linear or a branched configuration and attached to an alkyl group. Linear poly(alkoxy)alkyl moieties have a structure such as —(CH2)m—O—(CH2)m—O—(CH2)m—O—(CH2)m—. . . —O—CmH2m+1, where “m” is an integer, the same or different along the length of the chain. Branched moieties have two or more (—O—(CHt)m—) groups bound to a common third (—O—CHt)m—) group, where “t” has a value that is independently selected from 0, 1 and 2 for each (CHt)m group. Linear configurations are preferred. The number of repeating (—O—(CHt)m—) groups within a substituent may be up to 200, preferably from 2 to 20, more preferably from 2 to 7, and most preferably is 2-5. The individual alkoxy groups may be the same or different, and individual alkoxy groups preferably contain from 1 to 6 carbon atoms each, and most preferably from 1 to 3 carbon atoms each. A presently preferred poly(alkoxy)alkyl is—(CH2)y—(OCH2CH2)x—OCH3 or —(CH2)y—OCH2CH2)x—OCH2CH3, where y=1-4 and x=1-100, preferably 1-10, and more preferably, 2-5. The individual alkoxy groups may be substituted with one or more hydroxyl groups (an “hydroxypoly(alkoxy)alkyl”) or with one or more halogen atoms (a “halopoly(alkoxy)alkyl”); preferably the hydroxyl or halogen is on the terminal end of the poly(alkoxy)alkyl substituent. “Heterocyclo” designates a heterocyclic group; that is, a closed-ring structure, usually of either 5 or 6 members, in which one or more of the atoms in the ring is an element other than carbon, such as for example sulfur, nitrogen, or oxygen. A heterocyclic group may be, but is not limited to, pyridine, pyrrole, furan, thiophene, morpholine, and purine, optionally substituted with one or more nitro, carboxy, sulfonic acid, hydroxy, alkyl, alkoxy, or halide substituents.
—OOCH2CH═CH2 2.408
— In another embodiment of the invention, presently preferred benzimidazole derivatives are those where R is hydrogen, X is hydrogen, and Y is hydrogen or chloro and is in the 5(6)-position. Further preferred are those compounds where R and X are hydrogen, Y is hydrogen or chloro in the 5(6) position, and R1 is selected from those groups listed in Table 2:
— *Y = Cl, at the 5(6) position C. Screening Assays
A “potentiator,” as used herein, is a material that improves or increases the efficacy of the benzimidazole derivatives or a salt or a prodrug thereof, or that acts on the immune system as an immunomodulator. Potentiators can be used in combination with a compound of the present invention. A potentiator may be an antiviral agent. One such potentiator is triprolidine or its cis-isomer. Triprolidine is described in U.S. Pat. No. 5,114,951 (1992, the patent is incorporated by reference herein). A further potentiator is procodazole, (also named 1H-benzimidazole-2-propanoic acid, or β(2-benzimidazole) propionic acid or 2-(2-carboxyethyl)benzimidazole or propazol). Procodazole is a non-specific immunoprotective agent active against viral and bacterial infections and may be used in combination with the compounds set forth herein. Procodazole is effective with a compound of the present invention, alone in treating cancers, tumors, leukemia or viral infections, or combined with a chemotherapeutic agent.
Formulations of the present invention include the compound of the present invention, a salt thereof or a prodrug thereof and, optionally, a chemotherapeutic agent and, optionally, a potentiator, generally mixed with a pharmaceutically acceptable carrier. A “pharmaceutical carrier” is a pharmaceutically acceptable solvent, suspending agent or vehicle for delivering a compound of the present invention to the animal or human. The carrier may be liquid or solid and is selected with the planned manner of administration in mind. A “pharmaceutically acceptable” component is one that is suitable for use with humans and/or animals without undue adverse side effects (such as. toxicity, irritation, and allergic response) commensurate with a reasonable benefit/risk ratio.
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Thompson, Agricultural Chemicals Book IV, Fungicides, pp. 154, 121, 123, 1994.* Cited by examinerReferenced byCiting PatentFiling datePublication dateApplicantTitleUS6479526Mar 26, 2002Nov 12, 2002The Procter & Gamble CompanyPharmaceutical composition for inhibiting the growth of viruses and cancersUS6653335Nov 6, 2002Nov 25, 2003University Of Arizona FoundationaPharmaceutical composition for inhibiting the growth of viruses and cancersUS6720349Apr 25, 2002Apr 13, 2004Uaf Technologies And Research, LlcCompounds for use in the treatment of cancer or viral infectionsUS6906091Jul 18, 2002Jun 14, 2005Uaf Technologies And Research, LlcMethod of cancer treatmentUS6916836Aug 5, 2003Jul 12, 2005Uaf Technologies And Research, LlcCompounds and methods for use thereof in the treatment of viral infectionsUS6930121Oct 8, 2002Aug 16, 2005Uaf Technologies And Research, LlcCompounds and methods for use thereof in the treatment of viral infectionsUS6984654Jan 13, 2003Jan 10, 2006Uaf Technologies And Research, LlcCancer treatments and pharmaceutical compositions thereforUS7022712Mar 26, 2003Apr 4, 2006Arizona Board Of Regents On Behalf Of The University Of ArizonaSolubilization of weak basesUS20030032664 *Jul 18, 2002Feb 13, 2003The Procter & Gamble CompanyMethod of cancer treatmentUS20030100592 *Oct 8, 2002May 29, 2003University Of Arizona FoundationCompounds and methods for use thereof in the treatment of viral infectionsUS20030195225 *Mar 26, 2003Oct 16, 2003Yalkowsky Samuel H.Solubilization of weak basesUS20040029942 *Aug 5, 2003Feb 12, 2004University Of Arizona FoundationCompounds and methods for use thereof in the treatment of viral infectionsUS20050119236 *Jan 13, 2003Jun 2, 2005University Of Arizona FoundationCancer treatments and pharmaceutical compositions thereforUS20050192328 *Oct 21, 2004Sep 1, 2005Uaf Technologies And Research, LlcCompounds and methods for use thereof in the treatment of viral infectionsUS20050288349 *Aug 26, 2005Dec 29, 2005Uaf Technologies And Research, LlcCancer treatments and pharmaceutical compositions thereforUS20070043070 *Mar 12, 2004Feb 22, 2007Yalkowsky Samuel HWeak base salts* Cited by examinerClassifications U.S. Classification514/234.5, 544/139, 548/308.4, 514/388, 548/308.1International ClassificationC07D235/32, C07D235/30, A61K31/4184Cooperative ClassificationC07D235/32, C07D235/30, A61K31/4184European ClassificationC07D235/30, C07D235/32, A61K31/4184Legal EventsDateCodeEventDescriptionApr 22, 2002ASAssignmentOwner name: CTRC RESEARCH FOUNDATION, TEXASFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:QUADA JR., JAMES CLARENCE;AGYIN, JOSEPH KOFI;REEL/FRAME:012854/0468;SIGNING DATES FROM 20010820 TO 20010821Owner name: PROCTER & GAMBLE COMPANY, THE, OHIOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CAMDEN, JAMES BERGER;REEL/FRAME:012854/0511Effective date: 20010731Owner name: PROCTER & GAMBLE COMPANY, THE, OHIOFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:CTRC RESEARCH FOUNDATION;REEL/FRAME:012854/0566Effective date: 20010421Oct 30, 2002ASAssignmentOwner name: UNIVERSITY OF ARIZONA FOUNDATION, ARIZONAFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:PROCTER & GAMBLE COMPANY, THE;REEL/FRAME:013447/0227Effective date: 20021024Jan 6, 2003ASAssignmentOwner name: UNIVERSITY OF ARIZONA FOUNDATION, ARIZONAFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:PROCTOR & GAMBLE COMPANY, THE;REEL/FRAME:013634/0499Effective date: 20021024Oct 20, 2003ASAssignmentOwner name: UAF TECHNOLOGIES AND RESEARCH LLC, ARIZONAFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:ARIZONA FOUNDATION, UNIVERSITY OF;REEL/FRAME:014051/0993Effective date: 20031006Dec 1, 2005FPAYFee paymentYear of fee payment: 4Aug 6, 2008ASAssignmentOwner name: ARISYN THERAPEUTICS, INC., MARYLANDFree format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:UAF TECHNOLOGIES AND RESEARCH, LLC;REEL/FRAME:021339/0769Effective date: 20080804Jan 25, 2010REMIMaintenance fee reminder mailedJun 18, 2010LAPSLapse for failure to pay maintenance feesRotateOriginal ImageGoogle Home - Sitemap - USPTO Bulk Downloads - Privacy Policy - Terms of Service - About Google Patents - Send FeedbackData provided by IFI CLAIMS Patent Services