— 3 -
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`Amendments to the Claims
`
`This listing of claims will replace all prior versions, and listings of claims in the
`
`application.
`
`1.
`
`(Currently Amended)
`
`A method of inhibiting a taste modulating protein,
`
`the method comprising contacting the taste modulating protein with a compound of
`
`Formula 1:
`
`Ar1
`
`Ar2
`
`l
`
`R1
`N/
`/>——Ar3
`N
`
`1
`
`or a pharmaceutically acceptable salt thereof; wherein:
`
`R1 is hydrogen, unsubstituted alkyl, or unsubstituted arylalkyl;
`
`Ar1 and Ar2 are independently phenyl or heteroaryl, either of which is optionally
`
`substituted; and
`
`Ar3 is an optionally substituted: phenyl or [[a]] heteroarylreither—ef—whieh—is
`
`'III'L
`
`2.
`
`(Currently Amended)
`
`The method of claim 1, wherein Ar1 and Ar2 are
`
`independently selected from the group consisting of optionally substituted: phenyl;
`pyridyl, pyrimidinyl, pyridazinyl, pyrimidinyl, pyrazinyl, and triazinyl, any—9f
`
`whieh—i-s—eptienal-l—y—subst—ituted and N-oxides thereof.
`
`3.
`
`(Currently Amended)
`
`The method of claim 1, wherein Ar1 and A12 are
`
`independently selected from the group consisting of; unsubstituted phenyl,
`
`methylphenyl, methoxyphenyl,
`aminophenyl, and hydroxyphenyl.
`
`halophenyl,
`
`cyanophenyl,
`
`carboxyphenyl,
`
`I
`
`Atty. Dkt. No. 2305.0330001/TJS/A-L
`
`
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`Amendments to the Claims
`
`This listing of claims will replace all prior versions, and listings of claims in the
`
`application.
`
`1.
`
`(Currently Amended)
`
`A method of inhibiting a taste modulating protein,
`
`the method comprising contacting the taste modulating protein with a compound of
`
`Formula 1:
`
`Ar1
`
`Ar2
`
`l
`
`R1
`N/
`/>——Ar3
`N
`
`1
`
`or a pharmaceutically acceptable salt thereof; wherein:
`
`R1 is hydrogen, unsubstituted alkyl, or unsubstituted arylalkyl;
`
`Ar1 and Ar2 are independently phenyl or heteroaryl, either of which is optionally
`
`substituted; and
`
`Ar3 is an optionally substituted: phenyl or [[a]] heteroarylreither—ef—whieh—is
`
`'III'L
`
`2.
`
`(Currently Amended)
`
`The method of claim 1, wherein Ar1 and Ar2 are
`
`independently selected from the group consisting of optionally substituted: phenyl;
`pyridyl, pyrimidinyl, pyridazinyl, pyrimidinyl, pyrazinyl, and triazinyl, any—9f
`
`whieh—i-s—eptienal-l—y—subst—ituted and N-oxides thereof.
`
`3.
`
`(Currently Amended)
`
`The method of claim 1, wherein Ar1 and A12 are
`
`independently selected from the group consisting of; unsubstituted phenyl,
`
`methylphenyl, methoxyphenyl,
`aminophenyl, and hydroxyphenyl.
`
`halophenyl,
`
`cyanophenyl,
`
`carboxyphenyl,
`
`I
`
`Atty. Dkt. No. 2305.0330001/TJS/A-L
`
`
`
`— 4 -
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`(Canceled).
`
`(Canceled).
`
`(Currently Amended)
`
`The method of claim 1, wherein Ar3 is selected from
`
`the group consisting of optionally substituted phenyl, and optionally substituted:
`
`pyridyl, pyrimidinyl, pyridazinyl, pyrimidinyl, pyrazinyl, and triazinyl, anyhef
`
`Mneh—is-eptienally—wbstituted and N—oxides thereof.
`
`(Canceled).
`
`(Canceled).
`
`(Currently Amended)
`
`The method of claim 1, wherein Ar3 is selected from
`
`the group consisting of; phenyl, C-attached pyridyl, C-attached pyrimidyl, and
`
`C—attached pyridazinyl[[,]]; any of which is optionally substituted with one or
`
`more; nitro, halo, cyano, carboxyl, amino, hydroxyl, alkyl, and cyanoalkyl
`
`substituents in any one or more of the ortho-, meta-, and para-positions.
`
`10.
`
`(Currently Amended)
`
`V The method of claim 1, wherein
`
`R1 is hydrogen, unsubstituted C14 alkyl, or unsubstituted ary1(C1.4)alkyl;
`
`AI1 and Ar2 are both unsubstituted phenyl;fll
`
`AI3 is phenyl, optionally substituted by one to three substituents independently
`
`selected from the group consisting of carboxy, alkoxycarbonyl, hydroxy,
`
`hydroxyalkyl, amino, alkoxycarbonylamino, cyano, alkylsulfonylaminoalkyl, and
`
`nitro.
`
`ll.
`
`(Original)
`
`The method of claim 10, wherein Ar3 is phenyl, substituted in the
`
`para-position by one carboxy, alkoxycarbonyl, hydroxyalkyl, hydroxy, amino,
`
`alkoxycarbonylamino, cyano, alkylsulfonylaminoalkyl, or nitro.
`
`Atty. Dkt. No. 2305.0330001/TJS/A—L
`
`
`
`— 5 -
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`12.
`
`(Original)
`
`The method of claim 1, wherein the compound of Formula I is one
`
`of:
`
`methyl4-(4,5—diphenyl-IH-imidazol-Z-yl)benzoate;
`
`[4-(4,5—diphenyl-1H—imidazol-2-yl)phenyl]methanol;
`
`4—(4,5—dipheny1-IH-imidazol—Z—y1)aniline;
`
`4-(4,5-diphenyl—1H—imidazol-2-yl)phenol;
`
`methyl4-(4,5-diphenyl—1H-imidazol—Z-yl)pheny1carbamate;
`
`N-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl]acetamide;
`
`4—(4,5-dipheny1-1H—imidazol-Z-yl)benzonitrile;
`
`N-[4-(4,5-dipheny1-1H-imidazol-2-yl)benzy1]methanesulfonamide;
`
`4-(4,5-diphenyl-IH—imidazol—Z-yl)benzoic acid; and
`
`2—(4—nitro—phenyl)-4,5 —diphenyl— 1 H—imidazole;
`
`or a pharmaceutically acceptable salt thereof.
`
`13.
`
`14.
`
`15.
`
`16.
`
`17.
`
`(Original)
`
`The method of claim 1, wherein the taste modulating protein is a
`
`non-human TRPMS protein.
`
`(Canceled).
`
`(Original)
`
`The method of claim 1, wherein the taste modulating protein is a
`
`human TRPMS protein.
`
`(Canceled).
`
`(Currently Amended)
`
`The method of claim 1, wherein the compound of
`
`Formula I is administered as a pharmaceutical, veterinfl, food, cosmetic, or
`
`dental hygeinic composition.
`
`Atty. Dkt. No. 2305.0330001/TJS/A-L
`
`
`
`— 6 —
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`18.
`
`(Currently Amended)
`
`The method of claim 17, wherein the compound of
`
`Formula I is administered in a concentration of about 0.01% to about 50%, by
`
`weight, of the phanaiaeeut-iea-l-composition.
`
`19-26. (Canceled).
`
`27.
`
`(Original)
`
`The method of claim 1, wherein the compound of Formula I is
`
`administered in an amount of about 0.01 mg to about 100 mg.
`
`28.
`
`(Original)
`
`The method of claim 1, wherein the compound of Formula I is
`
`administered in an amount sufficient to inhibit the taste-modulating protein by
`
`about 10% to about 95%.
`
`29-53. (Canceled).
`
`54.
`
`(Currently Amended)
`
`A method of inhibiting the depolarization of a taste
`
`receptor cell, comprising contacting the taste receptor cell with one or more
`
`compounds of Formula I:
`
`1
`
`Ar
`
`R1
`/
`N
`
`| %AP
`
`Ar2
`
`N
`
`1
`
`or a pharmaceutically acceptable salt thereof; wherein:
`
`R1 is hydrogen, unsubstituted alkyl, or unsubstituted arylalkyl;
`
`Ar1 and Ar2 are independently phenyl or heteroaryl, either of which is optionally
`
`substituted; and
`
`Ar3 is an optionally substituted: phenyl or [[a]] heteroarylreither—eiLWhieh—is
`
`Atty. Dkt. No. 2305.0330001/TJS/A-L
`
`
`
`- 7 —
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`55.
`
`(Currently Amended)
`
`The method of claim 54, wherein Ar1 and Ar2 are
`
`independently selected from the group consisting of optionally substituted phenyl,
`
`and optionally substituted pyridyl, pyrimidinyl, pyridazinyl,
`
`pyrimidinyl,
`
`pyrazinyl, and triazinyl, thieh—is—epaeriall-yLsubsatuted and N-oxides
`
`thereof.
`
`56.
`
`(Currently Amended)
`
`The method of claim 54, wherein Ar1 and Ar2 are
`
`independently selected from the group consisting of; unsubstituted phenyl,
`
`methylphenyl, methoxyphenyl,
`
`halophenyl,
`
`cyanophenyl,
`
`carboxyphenyl,
`
`aminophenyl, and hydroxyphenyl.
`
`57.
`
`58.
`
`59.
`
`60.
`
`61.
`
`62.
`
`(Canceled).
`
`(Canceled).
`
`(Currently Amended)
`
`The method of claim 54, wherein Ar3 is selected
`
`from the group consisting of an optionally substituted: phenyl, pyridyl,
`
`pyrimidinyl, pyridazinyl, pyrimidinyl, pyrazinyl, and niazinylranyLef—whieh—is
`
`.
`
`ll
`
`1
`
`.
`
`i.
`
`(Canceled).
`
`(Canceled).
`
`(Original)
`
`The method of claim 54, wherein Ar3 is selected from the group
`
`consisting of phenyl, C-attached pyridyl, C—attached pyrimidyl, and C-attached
`
`pyridazinyl, any of which is optionally substituted with one or more nitro, halo,
`
`cyano, carboxyl, amino, hydroxyl, alkyl, and cyanoalkyl substituents in any one or
`
`more of the ortho-, meta-, and para-positions.
`
`63.
`
`(Currently Amended)
`
`The method of claim 54, wherein:
`
`Atty. Dkt. No. 2305 .033000 l/TJS/A-L
`
`
`
`— 8 —
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`R1 is hydrogen, unsubstituted C14 alkyl, or unsubstituted aryl(C1_4)alky1;
`
`Ar1 and Ar2 are both unsubstituted phenyl;fl:l
`
`Ar3 is phenyl, substituted by one to three substituents independently selected from
`
`the group consisting of carboxy, alkoxycarbonyl, hydroxy, hydroxyalkyl, amino,
`
`alkoxycarbonylamino, cyano, alkylsulfonylaminoalkyl, and nitro.
`
`64.
`
`(Original)
`
`The method of claim 63, wherein AI3 is phenyl, substituted in the
`
`para-position by one carboxy, alkoxycarbonyl, hydroxyalkyl, hydroxy, amino,
`
`alkoxycarbonylamino, cyano, alkylsulfonylaminoalkyl, or nitro.
`
`65.
`
`(Original)
`
`The method of claim 54, wherein the compound of Formula I is one
`
`of:
`
`methyl4-(4,5—dipheny1-1H-imidazol-Z-yl)benzoate;
`
`[4-(4,5-diphenyl—1H-imidazo1-2-yl)phenyl]methanol;
`
`4-(4,5-diphenyl—IH-imidazol—Z—yl)aniline;
`
`4—(4,5—diphenyl-1H—imidazol-2-y1)phenol;
`
`methyl4-(4,5-diphenyl-1H-imidazol-Z-yl)phenylcarbamate;
`
`N—[4-(4,5-dipheny1-1H—imidazol—2-yl)phenyl] acetamide;
`
`4-(4,5—dipheny1—IH-imidazo1—2—yl)benzonitri1e;
`
`N—[4-(4,5—diphenyl-1H—imidazol-2—yl)benzyl]methanesulfonamide;
`
`4-(4,5-diphenyl-IH-imidazol-Z-yl)benzoic acid; and
`
`2-(4-nitro-phenyl)-4,5—diphenyl-lH—imidazole;
`
`or a pharmaceutically acceptable salt thereof.
`
`66.
`
`67.
`
`(Original)
`
`The method of claim 54, wherein the taste receptor cell is human.
`
`(Original)
`
`The method of claim 54, wherein the compound of Formula I is
`
`administered as a pharmaceutical, veterinary, food, cosmetic, or dental hygienic
`
`composition.
`
`Atty. Dkt. No. 2305.0330001/TJS/A-L
`
`
`
`- 9 -
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`68.
`
`69.
`
`70.
`
`71.
`
`72.
`
`(Currently Amended)
`
`The method of claim 67, wherein the compound of
`
`Formula I is administered in a concentration of about 0.01% to about 50%, by
`
`
`
`weight, of the :-
`
`composition.
`
`(On'ginal)
`
`The method of claim 54, wherein the compound of Formula I is
`
`administered in an amount of about 0.01 mg to about 100 mg.
`
`(Original)
`
`The method of claim 54, wherein the compound of Formula I is
`
`administered in an amount sufficient to inhibit the depolarization of the taste-
`
`receptor cell by about 10% to about 95%.
`
`(Original)
`
`The method of claim 54, wherein the taste receptor cell can sense a
`
`taste produced by a biologically active agent.
`
`(Original)
`
`The method of claim 71, wherein the taste receptor cell can sense a
`
`taste produced by a biologically active agent selected from the group consisting of
`
`analgesics,
`
`anesthetics,
`
`anorexiants,
`
`appetite
`
`depressants,
`
`antacidics,
`
`antiasthmatics,
`
`antidiuretics,
`
`antipyretics,
`
`antihistamines,
`
`anticholinergics,
`
`antidiarrheals,
`
`antitussives,
`
`antinauseants,
`
`antiarrhythmics,
`
`antimicrobials,
`
`antibacterials, antifiingals, antivirals, anti-inflammatory agents, agents active
`
`against flatulence, antimigraine agents, beta—receptor blockers, bronchodilators,
`
`psychopharmacological
`
`agents,
`
`spasmolytics,
`
`sedatives,
`
`antihyperkinetics,
`
`tranquilizers,
`
`decongestants,
`
`demulcents,
`
`agents
`
`for
`
`alcohol withdrawal,
`
`antitussives,
`
`fluorine supplements,
`
`laxatives,
`
`local antibiotics, corticosteroid
`
`supplements, agents against goiter
`
`formation, antiepileptics, agents against
`
`dehydration,
`
`antiseptics, NSAle, Hz-receptor
`
`antagonists,
`
`nutritional
`
`supplements, gastrointestinal active agents, alkaloids,
`
`supplements for
`
`trace
`
`elements,
`
`ion-exchange resins,
`
`\cholesterol—depressant
`
`agents,
`
`lipid-lowering
`
`agents, expectorants, and combinations thereof.
`
`Atty. Dkt. No. 2305.0330001/TJS/A—L
`
`
`
`73. .
`
`(Original)
`
`The method of claim 54, wherein the taste receptor cell can sense a
`
`- 10 -
`
`ATWAL et al.
`
`Appl. No. 11/797,082
`
`bitter taste.
`
`74-213.
`
`(Canceled).
`
`214.
`
`(New)
`
`The method of claim 54, wherein the compound of Formula I is
`
`administered in an amount sufficient to inhibit the depolarization of the taste-
`
`receptor cell by about 25% to about 80%.
`
`Atty. Dkt. No. 2305.033000l/TJS/A-L
`
`
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