SA08290696B1 - مشتقات 1، 3- داي هيدرو -5- أيزو بنزو فيوران كربونيتريل جديدة وتركيبة صيدلانية منها لعلاج القذف المبكر - Google Patents
مشتقات 1، 3- داي هيدرو -5- أيزو بنزو فيوران كربونيتريل جديدة وتركيبة صيدلانية منها لعلاج القذف المبكر Download PDFInfo
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- SA08290696B1 SA08290696B1 SA08290696A SA08290696A SA08290696B1 SA 08290696 B1 SA08290696 B1 SA 08290696B1 SA 08290696 A SA08290696 A SA 08290696A SA 08290696 A SA08290696 A SA 08290696A SA 08290696 B1 SA08290696 B1 SA 08290696B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- dihydro
- isobenzofurancarbonitrile
- propyl
- formula
- hydrochloride
- Prior art date
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- 206010036596 premature ejaculation Diseases 0.000 title claims abstract description 33
- 238000011282 treatment Methods 0.000 title claims abstract description 18
- ZLXJXAMSNFFEFG-UHFFFAOYSA-N 1,3-dihydro-2-benzofuran-5-carbonitrile Chemical class N#CC1=CC=C2COCC2=C1 ZLXJXAMSNFFEFG-UHFFFAOYSA-N 0.000 title abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 230000002265 prevention Effects 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims description 62
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 45
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- DNEVVXBMQZYGEI-UHFFFAOYSA-N 2-benzofuran-1-carbonitrile Chemical compound C1=CC=CC2=C(C#N)OC=C21 DNEVVXBMQZYGEI-UHFFFAOYSA-N 0.000 claims description 24
- 125000002883 imidazolyl group Chemical group 0.000 claims description 22
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 17
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
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- -1 methoxyphenyl Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 8
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- STDUZIOHOYYXFQ-UHFFFAOYSA-N 1-(2-imidazol-1-ylethyl)-1-phenyl-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C(C#N)=CC=C2C=1COC2(C=1C=CC=CC=1)CCN1C=CN=C1 STDUZIOHOYYXFQ-UHFFFAOYSA-N 0.000 claims description 6
- VTKPPUCNPUZRIX-UHFFFAOYSA-N 1-(3-imidazol-1-ylpropyl)-1-thiophen-2-yl-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C(C#N)=CC=C2C=1COC2(C=1SC=CC=1)CCCN1C=CN=C1 VTKPPUCNPUZRIX-UHFFFAOYSA-N 0.000 claims description 6
- ZGXXBSJPVSIAMI-UHFFFAOYSA-N 1-(2-pyrazol-1-ylethyl)-1-thiophen-2-yl-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C(C#N)=CC=C2C=1COC2(C=1SC=CC=1)CCN1C=CC=N1 ZGXXBSJPVSIAMI-UHFFFAOYSA-N 0.000 claims description 5
- ZUQBQYCWNDENKM-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-(4-methylphenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCN(C)C)C1=CC=C(C)C=C1 ZUQBQYCWNDENKM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
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- WBNUFFFJTHQSSF-UHFFFAOYSA-N 1-(2-imidazol-1-ylethyl)-1-(4-methylphenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(C)=CC=C1C1(CCN2C=NC=C2)C2=CC=C(C#N)C=C2CO1 WBNUFFFJTHQSSF-UHFFFAOYSA-N 0.000 claims description 4
- MKDCWSYCOVWJPC-UHFFFAOYSA-N 1-(3-imidazol-1-ylpropyl)-1-phenyl-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C(C#N)=CC=C2C=1COC2(C=1C=CC=CC=1)CCCN1C=CN=C1 MKDCWSYCOVWJPC-UHFFFAOYSA-N 0.000 claims description 4
- HXMBDVREAJRXFW-UHFFFAOYSA-N 1-(3-pyrazol-1-ylpropyl)-1-thiophen-2-yl-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C(C#N)=CC=C2C=1COC2(C=1SC=CC=1)CCCN1C=CC=N1 HXMBDVREAJRXFW-UHFFFAOYSA-N 0.000 claims description 4
- RPQBHIZKVMIJRO-UHFFFAOYSA-N 1-(4-methylphenyl)-1-(3-pyrazol-1-ylpropyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(C)=CC=C1C1(CCCN2N=CC=C2)C2=CC=C(C#N)C=C2CO1 RPQBHIZKVMIJRO-UHFFFAOYSA-N 0.000 claims description 4
- UEHQUZJISJFFDE-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-phenyl-3h-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCN(C)C)C1=CC=CC=C1 UEHQUZJISJFFDE-UHFFFAOYSA-N 0.000 claims description 4
- DCABXDIJRCWHAL-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-phenyl-3h-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=CC=C1 DCABXDIJRCWHAL-UHFFFAOYSA-N 0.000 claims description 4
- MALKUTYHJOISBI-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-thiophen-2-yl-3h-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=CS1 MALKUTYHJOISBI-UHFFFAOYSA-N 0.000 claims description 4
- YNBJDBYOJQQNCF-UHFFFAOYSA-N 1-phenyl-1-(2-pyrazol-1-ylethyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C(C#N)=CC=C2C=1COC2(C=1C=CC=CC=1)CCN1C=CC=N1 YNBJDBYOJQQNCF-UHFFFAOYSA-N 0.000 claims description 4
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- HDHFSJCKDNFODQ-UHFFFAOYSA-N 1-(2-imidazol-1-ylethyl)-1-(4-methoxyphenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(OC)=CC=C1C1(CCN2C=NC=C2)C2=CC=C(C#N)C=C2CO1 HDHFSJCKDNFODQ-UHFFFAOYSA-N 0.000 claims description 3
- AXVNNIMDZYWHJD-UHFFFAOYSA-N 1-(2-imidazol-1-ylethyl)-1-(4-methoxyphenyl)-3h-2-benzofuran-5-carbonitrile;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1(CCN2C=NC=C2)C2=CC=C(C#N)C=C2CO1 AXVNNIMDZYWHJD-UHFFFAOYSA-N 0.000 claims description 3
- OLRBWKYORFTJJQ-UHFFFAOYSA-N 1-(2-imidazol-1-ylethyl)-1-thiophen-2-yl-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C(C#N)=CC=C2C=1COC2(C=1SC=CC=1)CCN1C=CN=C1 OLRBWKYORFTJJQ-UHFFFAOYSA-N 0.000 claims description 3
- ROHGAKXICXAPCR-UHFFFAOYSA-N 1-(3-imidazol-1-ylpropyl)-1-(4-methylphenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(C)=CC=C1C1(CCCN2C=NC=C2)C2=CC=C(C#N)C=C2CO1 ROHGAKXICXAPCR-UHFFFAOYSA-N 0.000 claims description 3
- MDETWWAVPHKIDU-UHFFFAOYSA-N 1-(4-methylphenyl)-1-(2-pyrazol-1-ylethyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(C)=CC=C1C1(CCN2N=CC=C2)C2=CC=C(C#N)C=C2CO1 MDETWWAVPHKIDU-UHFFFAOYSA-N 0.000 claims description 3
- CZTPZWVAYGVKQJ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-thiophen-2-yl-3h-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCN(C)C)C1=CC=CS1 CZTPZWVAYGVKQJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- MQXAQVRCUPWQEX-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-methylphenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)C)C1=CC=C(C)C=C1 MQXAQVRCUPWQEX-UHFFFAOYSA-N 0.000 claims description 2
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N phenyldimethylamine Natural products CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20070099016 | 2007-10-02 | ||
| KR1020080105439A KR101103118B1 (ko) | 2007-11-02 | 2008-10-27 | 신규한 1,3-디히드로-5-이소벤조퓨란카르보니트릴 유도체 화합물 및 이를 함유하는 조루증 치료용 약학조성물 |
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| Publication Number | Publication Date |
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| SA08290696B1 true SA08290696B1 (ar) | 2013-04-20 |
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| Application Number | Title | Priority Date | Filing Date |
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| SA08290696A SA08290696B1 (ar) | 2007-10-02 | 2008-11-01 | مشتقات 1، 3- داي هيدرو -5- أيزو بنزو فيوران كربونيتريل جديدة وتركيبة صيدلانية منها لعلاج القذف المبكر |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR100920125B1 (ko) |
| SA (1) | SA08290696B1 (ko) |
| UA (1) | UA95028C2 (ko) |
| ZA (1) | ZA201002470B (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR100353014B1 (ko) * | 1998-11-11 | 2002-09-18 | 동아제약 주식회사 | 발기부전 치료에 효과를 갖는 피라졸로피리미디논 화합물 |
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2008
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- 2008-09-24 UA UAA201004418A patent/UA95028C2/ru unknown
- 2008-11-01 SA SA08290696A patent/SA08290696B1/ar unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| ZA201002470B (en) | 2011-06-29 |
| KR20090034266A (ko) | 2009-04-07 |
| KR100920125B1 (ko) | 2009-10-01 |
| UA95028C2 (ru) | 2011-06-25 |
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