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US 7,745,433 B2Granted
2-Substituted phenyl-5, 7-dihydrocarbyl-3, 7-dihydropyrrolo [2, 3-D] pyrimidin-4-one derivatives, the preparation and the pharmaceutical use thereof
AssigneesYangtze River Pharmacuetical (Group) Co., Ltd., Tianjin North Pharma Sci-Tech Co., Ltd.
InventorsYongfeng Wang, Kejun Zhao
Life of this patent
Estimating the term…
Abstract
The invention relates to the compounds of formula I, their preparation and the pharmaceutical compositions containing the compounds. The invention also relates to the use of the compounds of formula I in preparing medicines, which can treat sexual dysfunction of animals including human (male and female), especially erectile dysfunction of male and the diseases in which the function of phospholipase 5 (cGMP PDE5) is involved.
Claims5
A compound of the formula I:
- wherein R1 is C1-C4 branched or straight chain alkyl;
- R2 is H;
- R3 is H;
- C1-C6 branched or straight chain alkyl;
- C2-C4 alkenyl;
- or C2-C4 alkynyl;
- R4 is H;
- C1-C6 branched or straight chain alkyl;
- or C2-C4 alkenyl;
- R5 is SO2NR10R11;
- R8 is H;
- or C1-C6 branched or straight chain alkyl;
- R10 and R11 are each independently H;
- C1-C12 branched or straight chain alkyl;
- C1-C3 halogenated branched or straight chain alkyl;
- C2-C6 alkenyl;
- C2-C6 alkynyl or C3-C6 cycloalkyl;
- or R10 and R11 together with their attached nitrogen atom form a pyrrolinyl, pyrrolinone group, piperidyl, morpholinyl, or 4-N(R8)-piperazinyl;
- the said groups are optionally substituted with OH, CN, CO2R8, C1-C4 branched or straight chain alkyl, or C1-C3 alkoxyl;
- or their pharmaceutically acceptable salts.
17 more elements
The compound selected from the group consisting of:
- 2-[2-ethoxyl-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-methoxyl-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, and the hydrochloride thereof;
- 2-[2-n-propoxy-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, and the hydrochloride thereof;
- 2-[2-allyloxy-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, and the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-n-propoxy-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-ethyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-methylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-methylpiperazinyl-1-sulfonyl)phenyl]-5-ethyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-ethoxycarbonylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[4-(2-hydroxyethyl)piperazinyl-1-sulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(pyrrolidinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[3-(2-oxy-pyrrolidin-1-yl)-n-propylamino-N-sulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[2-(pyrrolidin-1-yl)-ethylamino-N-sulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(morpholino-4-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[3-(morpholin-4-yl)-n-propylamino-N-sulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[2-(morpholin-4-yl)-ethylamino-N-sulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(2,6-dimethylmorpholino-N-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(1-benzylpiperidyl-4-aminosulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[2-(piperidin-1-yl)ethylamino-1-sulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-benzylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-phenylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(piperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-benzo[1,3]-dioxol-5-yl-methylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[4-(3-phenyl-n-propan-1-yl)piperidyl-1-sulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(n-propylamino-1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[N,N-di(2-hydroxyethyl)aminosulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[N-(2-hydroxyethyl)-N-methylaminosulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[N-(2-hydroxyethyl)-N-ethylaminosulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-{2-ethoxyl-5-[N-(2-hydroxyethyl)-N-n-butylaminosulfonyl]phenyl}-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(p-ethoxylcarboxylphenylamino-N-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(o-benzoylphenylamino-N-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydro chloride, dihydro chloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(N2-acethydrazido-N1-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride and dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(2-dimethylaminoethylamino-N-sulfonyl)phenyl]-5-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-ethyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-morpholinomethyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- 2-[2-ethoxyl-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-(pyrimidinyl-2)-methyl-7-n-propyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof;
- and
- 2-[2-ethoxyl-5-(4-ethylpiperazinyl-1-sulfonyl)phenyl]-5-methyl-7-allyl-3,7-dihydropyrrolo[2,3-d]pyrimidin-4-one, the monohydrochloride, dihydrochloride and other possible hydrochloride thereof.
34 more elements
Dependencies are inferred from the claim text.