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Details for Patent: 7,273,868

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Details for Patent: 7,273,868

Title:Pyrazine derivatives
Abstract: 1. A cyclic compound of the formula (I) or a pharmacologically acceptable salt thereof, ##STR00001## wherein X is .dbd.CH-- or .dbd.N--, Y is --NH--, --NR.sup.4--, --S--, --O--, --CH.dbd.N--, --N.dbd.CH--, --N.dbd.N--, --CH.dbd.CH--, etc., R.sup.1 is a lower alkoxy group, an amino group, a heterocyclic ring containing N atom(s), or a hydroxy group substituted by a heterocyclic ring containing N atom(s) (each of which is optionally substituted), R.sup.2 is a lower alkylamino group which is optionally substituted by an aryl group, a lower alkoxy group which is optionally substituted by an aryl group, a lower alkoxy group substituted by an aromatic heterocyclic ring containing N atom(s), R.sup.3 is an aryl group, a heterocyclic ring containing N atom(s), a lower alkyl group, a lower alkoxy group, a cyclo lower alkoxy group, a hydroxy group substituted by a heterocyclic ring containing N atom(s), or an amino group (each of which is optionally substituted), and R.sup.3 and a substituent in Y may be combined to form a lactone ring. The compound of the present invention has excellent selective PDE V inhibitory activity and therefore, is useful as a therapeutic or prophylactic drug for treating various diseases due to functional disorders on cGMP-signaling.
Inventor(s): Yamada; Koichiro (Saitama-ken, JP), Matsuki; Kenji (Saitama-ken, JP), Omori; Kenji (Saitama-ken, JP), Kikkawa; Kohei (Kawaguchi, JP)
Assignee: Tanabe Seiyaku Co., Ltd. (Osaka, JP)
Filing Date:Nov 04, 2003
Application Number:10/699,804
Claims:1. A cyclic compound of the formula (I) or a pharmacologically acceptable salt thereof, ##STR00734## wherein X is .dbd.N--, Y is --CH.dbd.N--, or ##STR00735## R.sup.1 is a lower alkoxy group which is optionally substituted, an amino group which is optionally substituted, a heterocyclic ring containing N atom(s) which is optionally substituted, a hydroxy group which is optionally substituted by a heterocyclic ring containing N atom(s) which is optionally substituted, or a cyano group, R.sup.2 is a lower alkylamino group which is optionally substituted by an aryl group which is optionally substituted, a lower alkoxy group which is optionally substituted by an aryl group which is optionally substituted, a lower alkoxy group substituted by an aromatic heterocyclic ring containing N atom(s) which is optionally substituted, a lower alkylamino group substituted by a heterocyclic ring which is optionally substituted, or an amino group substituted by an aryl group which is optionally substituted, R.sup.3 is an aryl group which is optionally substituted, a heterocyclic ring containing N atom(s) which is optionally substituted, a lower alkyl group which is optionally substituted, a lower alkoxy group which is substituted, a cyclo lower alkoxy group which is optionally substituted, a hydroxy group substituted by a heterocyclic ring containing N atom(s) which is optionally substituted, or an amino group which is substituted by one or two, same or different, substituents selected from the group consisting of (i) a lower alkoxy group which is optionally substituted by a lower alkoxy group, (ii) a lower alkyl group which is substituted by one to three, same or different, substituents selected from the group consisting of cyano group, hydroxy group, a lower alkoxy group, a phenyl group which is optionally substituted by a lower alkoxy group and/or a halogen atom, carbamoyl group, a lower alkylamino group, a pyridyl group, a lower alkyl pyridyl group, a lower alkoxy pyridyl group, a pyrimidinyl group, a lower alkoxy pyrimidinyl group, a morpholinyl group, a lower alkyl morpholinyl group, a hydroxy-substituted lower alkyl morpholinyl group, a cyano-substituted lower alkylmorpholinyl group, a hydroxy-substituted piperidyl group, an oxo-substituted piperazinyl group, a lower alkyl piperazinyl group, a lower alkylsulfonylpiperazinyl group, a pyrrolidinyl group, a lower alkylpyrrolidinyl group, a lower alkylpyrazinyl group, a tetrahydrofuranyl group, a lower alkoxypyridylamino group, and a pyrimidinylamino group, (iii) a phenyl group which is optionally substituted by hydroxy group or a lower alkoxy group, (iv) a pyridyl group which is optionally substituted by a lower alkyl group, (v) a pyrazolyl group which is optionally substituted by a lower alkyl group, (vi) an isoxazolyl group which is optionally substituted by a lower alkyl group, (vii) a morpholinyl group, (viii) a piperidyl group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a lower alkyl group, a cyano-substituted lower alkyl group, a hydroxy-substituted lower alkanoyl group, formyl group, a lower alkoxy-substituted lower alkanoyl group, and a lower alkylamino-substituted lower alkanoyl group, (ix) a cyclo lower alkyl group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of a hydroxy group which is optionally protected, a lower alkoxy group, and a pyrimidinyl-substituted oxy group, and (x) a pyrimidinylamino group which is optionally substituted by a lower alkyl group or a lower alkoxycarbonyl group, and R.sup.5 is an aryl group which is optionally substituted, a heterocyclic ring containing N atom(s) which is optionally substituted, a lower alkoxy group which is optionally substituted, or an amino group which is optionally substituted, or R.sup.5 may combine with R.sup.3 to form a lactone ring represented by the following formula ##STR00736## wherein, when Y is CH.dbd.N--, R.sup.2 is an amino group mono-substituted by a methyl group substituted by an aryl which is optionally substituted, and R.sup.3 is a lower alkyl which is optionally substituted, an amino group mono-substituted by a lower alkyl group substituted by a heterocyclic ring containing N atom(s) which is optionally substituted, an amino group mono-substituted by a heterocyclic ring containing N atom(s) which is optionally substituted or an amino group mono-substituted by a cyclo lower alkyl group which is optionally substituted, R.sup.1 is a lower alkoxy group which is optionally substituted, an amino group which is optionally substituted, a hydroxy group which is optionally substituted by a heterocyclic ring containing N atom(s) which is optionally substituted, or a cyano group.

2. The compound claimed in claim 1, wherein ##STR00737##

3. The compound claimed in claim 1, wherein Y is --CH.dbd.N--.

4. The compound claimed in any of claims 1, 2, or 3, wherein R.sup.1 is (1) a lower alkoxy group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of a cyclo lower alkyl group, hydroxy group, a lower alkylamino group which is optionally protected, a lower alkoxy group, a hydroxy-substituted lower alkyl group, phenyl group, a lower alkoxyphenyl group, a hydroxy-substituted lower alkylphenyl group, a furyl group, a pyridyl group, a lower alkoxypyridyl group, a hydroxy-substituted lower alkylpyridyl group, a lower alkylpyridyl group, a pyrimidinyl group, a lower alkoxypyrimidinyl group, and a morpholinyl group, (2) a lower alkylamino group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of hydroxy group, a lower alkoxy group, a lower alkyl group, a pyridyl group, a lower alkylamino group, cyano group, a phenyl group which is optionally substituted by a lower alkoxy group and/or a halogen atom, and a hydroxy-substituted lower alkyl group, (3) an indanylamino group, (4) a heterocyclic ring containing N atom(s) which is optionally substituted by one to four, same or different, substituents selected from the group consisting of hydroxyl group, a lower alkyl group, a lower alkoxy group, a hydroxy-substituted lower alkyl group, oxo group, a pyridyl group which is optionally substituted by a hydroxy-substituted lower alkyl group, a pyrimidinyl group which is optionally substituted by a lower alkylamino group, formyl group, mesyl group, a lower alkanoyl group substituted by a hydroxy group which is optionally protected, and carbamoyl group, (5) a hydroxy group which is optionally substituted by a pyridyl group, or (6) a cyano group, R.sup.2 is (1) a lower alkylamino group substituted by an aryl group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxy group, a halogen atom, an amino group, a lower alkanoylamino group, a formylamino group, hydroxy group, a lower alkoxypyridyl group, a lower alkylamino group, nitro group, a halogeno-substituted lower alkyl group, a lower alkylenedioxy group, cyano group, a lower alkyl group substituted by a hydroxy group which is optionally protected, a lower alkylsulfonyl group, and a lower alkylsulfinyl group, (2) a lower alkoxy group substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxy group and a halogen atom, (3) a lower alkoxy group substituted by a pyridyl group, (4) a lower alkylamino group substituted by an indolyl group, a pyrimidinyl group, a benzofuranyl group, a dihydrobenzofuranyl group, a lower alkylpyrimidinyl group, a dihydrobenzoxazolyl or a dihydrobenzimidazolyl group, or (5) an indanylamino group, R.sup.3 is (1) an aryl group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxy group and an lower alkylamino group, or an aryl group which is optionally substituted by one or two lower alkylenedioxy groups, (2) a heterocyclic ring containing N atom(s) which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkyl group, hydroxy group, an amino group, chlorosulfinyloxy group and a piperidinyloxysulfinyloxy group, (3) a lower alkyl group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of a morpholinyl group and a di-lower alkoxyphosphoryl group, (4) a lower alkoxy group which is substituted by one to three, same or different, substituents selected from the group consisting of a pyridyl group, a lower alkoxypyridyl group, a pyrimidinyl group, a lower alkylamino group, a pyrazinyl group, a lower alkoxy group which is optionally substituted by phenyl group, a pyrimidinyl-substituted oxy group, a pyridyl-substituted oxy group, a pyrimidinyl-substituted lower alkoxy group, a morpholinyl group, a lower alkylmorpholinyl group, a N-lower alkyl-N-pyrimidinylamino group, a lower alkyldioxolanyl group, a lower alkoxy-substituted lower alkoxy group, a pyrldylcarbonylamlno group, hydroxy group, and a lower alkylplperldyl group, (5) a cyclo lower alkoxy group which is optionally substituted by hydroxy group, (6) a plpeddyl-substltuted hydroxy group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a pyilmidinyl group, a lower alkyl group and a cyano-substituted lower alkyl group, or (7) an amino group which is substituted by one or two, same or different, substituents selected from the group consisting of (i) a lower aikoxy group which is optionally substituted by a lower alkoxy group, (ii) a lower alkyl group which is substituted by one to three, same or different, substituents selected from the group consisting of cyano group, hydroxy group, a lower alkoxy group, a phenyl group which is optionally substituted by a lower alkoxy group and/or a halogen atom, carbamoyl group, a lower aikylamino group, a pyridyl group, a lower alkyl pyridyl group, a lower alkoxy pyridyl group, a pydmidinyl group, a lower alkoxy pyrimidinyl group, a morphoilnyl group, a lower alkyl morphoilnyl group, a hydroxy-substituted lower alkyl morpholinyl group, a cyano-substituted lower alkylmorphoilnyl group, a hydroxy-substituted piperidyl group, an oxo-substituted piperazinyl group, a lower alkyl piperazinyl group, a lower alkylsulfonylpiperazinyl group, a pyrroildinyl group, a lower alkylpyrrolidinyl group, a lower alkylpyrazinyl group, a tetrahydrofuranyl group, a lower alkoxypyridylamino group, and a pydmidinylamino group, (iii) a phenyl group which is optionally substituted by hydroxy group or a lower alkoxy group, (iv) a pyridyl group which is optionally substituted by a lower alkyl group, (v) a pyrazolyl group which is optionally substituted by a lower alkyl group, (vi) an isoxazolyl group which is optionally substituted by a lower alkyl group, (vii) a morpholinyl group, (viii) a piperidyl group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a lower alkyl group, a cyano-substituted lower alkyl group, a hydroxy-substituted lower alkanoyl group, formyl group, a lower alkoxy-substituted lower alkanoyl group, and a lower alkylamino-substituted lower alkanoyl group, (ix) a cyclo lower alkyl group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of a hydroxy group which is optionally protected, a lower alkoxy group, and a pyrimidinyl-substituted oxy group, and (x) a pyrimidinylamino group which is optionally substituted by a lower alkyl group or a lower alkoxycarbonyl group, and R.sup.5 is (1) a phenyl group which is optionally substituted by a lower alkoxy group, (2) a heterocyclic ring containing N atom(s) which is optionally substituted by hydroxy group, a lower alkyl group or a hydroxy-substituted lower alkyl group, (3) a lower alkoxy group, or (4) an amino group which is optionally substituted by a lower alkyl group substituted by a heterocyclic ring containing N atom(s), a hydroxy-substituted cyclo lower alkyl group, or a lower alkyl group, or (5) R.sup.5 optionally combines with R.sup.3 to form a lactone ring as shown in the following formula; ##STR00738##

5. The compound claimed in claim 2, wherein R.sup.1 is (1) a lower alkoxy group which is optionally substituted by a lower alkylamino group or a pyridyl group, (2) an amino group which is optionally substituted by hydroxy group or a lower alkoxy group, (3) a heterocyclic ring containing N atom(s) which is optionally substituted by hydroxy group, a lower alkoxy group, a lower alkyl group, a hydroxy-substituted lower alkyl group, oxo group, a pyridyl group which is optionally substituted by a hydroxy-substituted lower alkyl group, or a pyrimidinyl group which is optionally substituted by a lower alkylamino group, or (4) a hydroxy group which is optionally substituted by a pyridyl group, R.sup.2 is a lower alkylamino group which is optionally substituted by a phenyl group which is optionally substituted by a lower alkoxy group and/or a halogen atom, R.sup.3 is (1) a lower alkoxy group which is substituted by a phenyl-substituted lower alkoxy group, or (2) an amino group which is substituted by (i) a lower alkyl group which is substituted by the same or different subsituents selected from a group of consisting of a lower alkoxy group, a pyridyl group, a lower alkylpyridyl group, a pyrimidinyl group, a lower alkoxypyrimidinyl group, a morpholinyl group, and a lower alkylpyrazinyl group, (ii) a pyridyl group which is optionally substituted by a lower alkyl group, or (iii) a cyclo lower alkyl group which is optionally substituted by hydroxy group, and R.sup.5 is (1) a phenyl group which is optionally substituted by a lower alkoxy group, (2) a heterocyclic ring containing N atom(s) which is optionally substituted by a hydroxy group, a lower alkyl group or a hydroxy-substituted lower alkyl group, (3) a lower alkoxy group, or (4) an amino group which is optionally substituted by a lower alkyl group substituted by a heterocyclic ring containing N atom(s), a hydroxy-substituted cyclo lower alkyl group, or a lower alkyl group, or (5) R.sup.5 optionally combines with R.sup.3 to form a lactone ring as shown in the following formula, ##STR00739##

6. The compound claimed in claim 3, wherein R.sup.1 is (1) a lower alkoxy group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of a cyclo lower alkyl group, hydroxy group, a lower alkylamino group which is optionally protected, a lower alkylamino group, a lower alkoxy group, a hydroxy-substituted lower alkyl group, phenyl group, a lower alkoxyphenyl group, a hydroxy-substituted lower alkylphenyl group, a furyl group, a pyridyl group, a lower alkoxypyridyl group, a hydroxy-substituted lower alkylpyridyl group, a lower alkylpyridyl group, a pyrimidinyl group, a lower alkoxypyrimidinyl group, and a morpholinyl group, (2) a lower alkylamino group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of hydroxy group, a lower alkoxy group, a lower alkyl group, a pyridyl group, a lower alkylamino group, cyano group, a phenyl group which is optionally substituted by a lower alkoxy group and/or a halogen atom, and a hydroxy-substituted lower alkyl group, (3) an indanylamino group, (4) a heterocyclic ring containing N atom(s) which is optionally substituted by one to four, same or different, substituents selected from the group consisting of hydroxy group, a lower alkyl group, a lower alkoxy group, a hydroxy-substituted lower alkyl group, oxo group, a pyridyl group which is optionally substituted by a hydroxy-substituted lower alkyl group, a pyrimidinyl group which is optionally substituted by a lower alkylamino group, formyl group, mesyl group, a lower alkanoyl group substituted by a hydroxy group which is optionally protected, and carbamoyl group, (5) a cyano group, or (6) a hydroxyl group which is optionally substituted by a pyridyl group, R.sup.2 is (1) a lower alkylamino group substituted by an aryl group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxy group, a halogen atom, an amino group, a lower alkanoylamino group, a formylamino group, hydroxy group, a lower alkoxy pyridyl group, a lower alkylamino group, nitro group, a halogen-substituted lower alkyl group, a lower alkylenedioxy group, cyano group, a lower alkyl group substituted by a hydroxyl group which is optionally protected, a lower alkylsulfonyl group, and a lower alkylsulfinyl group, (2) a lower alkylamino group substituted by an indolyl group, a pyrimidinyl group, a benzofuranyl group, a dihydrobenzofuranyl group, a lower alkylpyrimidinyl group, a dihydrobenzoxazolyl group or a dihydrobenzimidazolyl group, (3) an indanylamino group, (4) a lower alkoxy group substituted by an aryl group which is optionally substituted by one to four, same or different, substituents selected from a lower alkoxy group and a halogen atom, or (5) a lower alkoxy group substituted by a pyridyl group, R.sup.3 is (1) an aryl group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxy group and a lower alkylamino group, or an aryl group which is optionally substituted by one or two lower alkylenedioxy groups, (2) a heterocyclic ring containing N atom(s) which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkyl group, hydroxy group, an amino group, chlorosulfinyloxy group and a piperidyloxysulfinyloxy group, (3) a lower alkyl group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of a morpholinyl group and a di-lower alkoxyphosphoryl group, (4) a lower alkoxy group which is substituted by one to three, same or different, substituents selected from the group consisting of a pyridyl group, a lower alkoxypyridyl group, a pyrimidinyl group, a lower alkylamino group, a pyrazinyl group, a lower alkoxy group which is optionally substituted by phenyl group, a pyrimidinyl-substituted oxy group, a pyridyl-substituted oxy group, a pyrimidinyl-substituted lower alkoxy group, a morpholinyl group, a lower alkylmorpholinyl group, a N-lower alkyl-N-pyrimidinylamino group, a lower alkyl dioxolanyl group, a lower alkoxy-substituted lower alkoxy group, a pyridylcarbonylamino group, hydroxy group, and a lower alkylpiperidyl group, (5) a cyclo lower alkoxy group which is optionally substituted by hydroxyl group, (6) a piperidyl-substituted hydroxy group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a pyrimidinyl group, a lower alkyl group and a cyano-substituted lower alkyl group, or (7) an amino group which is substituted by one or two, same or different, substituents selected from the group consisting of (i) a lower alkoxy group which is optionally substituted by a lower alkoxy group, (ii) a lower alkyl group which is substituted by one to three, same or different, substituents selected from the group consisting of cyano group, hydroxy group, a lower alkoxy group, a phenyl group which is optionally substituted by a lower alkoxy group and/or a halogen atom, carbamoyl group, a lower alkylamino group, a pyridyl group, a lower alkylpyridyl group, a lower alkoxypyridyl group, pyrimidinyl group, a lower alkoxypyrimidinyl group, a morpholinyl group, a lower alkyl morpholinyl group, a hydroxy-substituted lower alkyl morpholinyl group, a cyano-substituted lower alkyl morpholinyl group, a hyd roxy-substituted piperidyl group, an oxo-substituted piperazinyl group, a lower alkyl piperazinyl group, a lower alkylsulfonylpiperazinyl group, a pyrrolidinyl group, a lower alkyl pyrrolidinyl group, a lower alkyl pyrazinyl group, a tetrahydrofuranyl group, a lower alkoxy pyridylamino group, and a pyrimidinylamino group, (iii) a phenyl group which is optionally substituted by hydroxy group or a lower alkoxy group, (iv) a pyridyl group which is optionally substituted by a lower alkyl group, (v) a pyrazolyl group which is optionally substituted by a lower alkyl group, (vi) an isoxazolyl group which is optionally substituted by a lower alkyl group, (vii) a morpholinyl group, (viii) a piperidyl group which is optionally substituted by one to four, same or different, substituents selected from the group consisting of a lower alkoxycarbonyl group, a lower alkylsulfonyl group, a lower alkyl group, a cyano-substituted lower alkyl group, a hydroxy-substituted lower alkanoyl group, formyl group, a lower alkoxy-substituted lower alkanoyl group, and a lower alkylamino-substituted lower alkanoyl group, (ix) a cyclo lower alkyl group which is optionally substituted by one to three, same or different, substituents selected from the group consisting of a hydroxy group which is optionally protected, a lower alkoxy group, and a pyrimidinyl-substituted oxy group, and (x) a pyrimidinylamino group which is optionally substituted by a lower alkyl group or a lower alkoxycarbonyl group.

7. The compound claimed in claim 1, wherein an aryl group on R.sup.1, R.sup.2, R.sup.3, or R.sup.5 is a monocyclic, bicyclic or tricyclic 6-14 membered aryl group which may be partially saturated, or a heterocyclic ring containing N atom(s) on R.sup.1, R.sup.3, or R.sup.5 is a monocyclic or bicyclic 5 to 14 membered heterocyclic containing N atom(s).

8. The compound claimed in claim 7, wherein the monocyclic, bicyclic or tricyclic 6-14 membered aryl group which may be partially saturated on R.sup.1, R.sup.2, R.sup.3, or R.sup.5 is phenyl, naphthyl, indenyl or indanyl.

9. The compound claimed in claim 7, wherein the monocyclic or bicyclic 5 to 14 membered heterocyclic ring containing N atom(s) on R.sup.1, R.sup.3, or R.sup.5 is pyridyl, pyrimidinyl, imidazolyl, piperidyl, pyrazolyl, morpholinyl, piperazinyl, pyrrolidinyl, dihydroisoindolyl, tetrahydroimidazo[1,2-a]pyrazyl, tetrahydroisoquinolyl, dihydro-5H-pyrrolo[3,4-b]pyridyl, naphthylid inyl, pyrazo[3,4-d]pyridyl, tetrahydropyridyl, oxazolo[4,5-c]pyridyl, octahydropyrido[3,4-d]pyrimidinyl, thiazolo[4,5-d]pyridyl, imidazo[4,5-d]pyridyl, perhydrodiazepinyl, perhydropiperadino[3,4-c]piperadinyl, tetrahydroisoxazolo[4,5-c]pyridyl, hexahydropyrazolo[4,3-c]pyridyl, dihydropyridyl, tetrahydroxazolo[5,4-c]pyridyl, hexahydropyrido[3,4-d]pyrimidinyl, octahydropyrido[4,3-d]pyrimidinyl, tetrahydrothiazolo[5,4-c]pyridyl, imidazo[4,5-b]pyridyl, homopiperazinyl, perhydropyrazino[1,2-a]pyrazinyl, tetrahydropyrido[4,3-d]pyrimidinyl, tetrahydrothieno[3,2-c]pyridyl, or tetrahydronaphthylidinyl.

10. A pharmaceutical composition containing a compound claimed in claim 1 or a pharmacologically acceptable salt thereof as an active ingredient.

11. A method for treating erectile dysfunction, comprising administering to a patient in need thereof an effective amount of a compound claimed in claim 1 or a pharmacologically acceptable salt thereof.

12. A method for treating pulmonary hypertension, comprising administering to a patient in need thereof an effective amount of a compound claimed in claim 1 or a pharmacologically acceptable salt thereof.

13. A method for treating diabetic gastroparesis comprising administering to a patient in need thereof an effective amount of a compound claimed in claim 1 or a pharmacologically acceptable salt thereof.
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