CA2168443A1 - Derives de la piperazine, antagonistes du recepteur .alpha.1a-adrenergique - Google Patents
Derives de la piperazine, antagonistes du recepteur .alpha.1a-adrenergiqueInfo
- Publication number
- CA2168443A1 CA2168443A1 CA002168443A CA2168443A CA2168443A1 CA 2168443 A1 CA2168443 A1 CA 2168443A1 CA 002168443 A CA002168443 A CA 002168443A CA 2168443 A CA2168443 A CA 2168443A CA 2168443 A1 CA2168443 A1 CA 2168443A1
- Authority
- CA
- Canada
- Prior art keywords
- methoxyphenyl
- piperazinyl
- propyl
- group
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000004885 piperazines Chemical class 0.000 title claims description 6
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title description 3
- 239000000674 adrenergic antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 239000000651 prodrug Substances 0.000 claims abstract description 10
- 229940002612 prodrug Drugs 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 43
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- -1 cyano, hydroxy Chemical group 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000000010 aprotic solvent Substances 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 claims description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 3
- 239000007822 coupling agent Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- BGZXIIUXZDCEMW-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl 2-phenylacetate Chemical compound COC1=CC=CC=C1N1CCN(CCOC(=O)CC=2C=CC=CC=2)CC1 BGZXIIUXZDCEMW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- TUCDBHDYVQWWGA-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-(2-phenylmethoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)CC=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 TUCDBHDYVQWWGA-UHFFFAOYSA-N 0.000 claims description 2
- LPCJDMQYUFHQDQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-[(4-nitrophenyl)methoxy]benzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OCC=2C=CC(=CC=2)[N+]([O-])=O)CC1 LPCJDMQYUFHQDQ-UHFFFAOYSA-N 0.000 claims description 2
- SKTSTUNBRPVCHA-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenylbenzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)CC1 SKTSTUNBRPVCHA-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- KURLOUQKLBHJMC-UHFFFAOYSA-N 2-[(4-benzoylphenyl)methoxy]-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-propanoylbenzamide Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C=CC=1COC=1C(C(=O)CC)=CC=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC KURLOUQKLBHJMC-UHFFFAOYSA-N 0.000 claims 1
- CORAXKNCTKVOKH-UHFFFAOYSA-N 2-[(4-benzoylphenyl)methoxy]-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]benzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OCC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)CC1 CORAXKNCTKVOKH-UHFFFAOYSA-N 0.000 claims 1
- GRBLDFRQINXRCN-UHFFFAOYSA-N 2-benzyl-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]benzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)CC=2C=CC=CC=2)CC1 GRBLDFRQINXRCN-UHFFFAOYSA-N 0.000 claims 1
- USELWWSAEGIMTQ-UHFFFAOYSA-N 2-hydroxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-propanoylbenzamide Chemical compound CCC(=O)C1=CC=CC(C(=O)NCCCN2CCN(CC2)C=2C(=CC=CC=2)OC)=C1O USELWWSAEGIMTQ-UHFFFAOYSA-N 0.000 claims 1
- QNZKWFVUTMHNRV-UHFFFAOYSA-N 2-methoxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-propanoylbenzamide Chemical compound CCC(=O)C1=CC=CC(C(=O)NCCCN2CCN(CC2)C=2C(=CC=CC=2)OC)=C1OC QNZKWFVUTMHNRV-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- HPGJBQNOFRPUHD-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-(cyclohexylmethoxy)benzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OCC2CCCCC2)CC1 HPGJBQNOFRPUHD-UHFFFAOYSA-N 0.000 claims 1
- QBPOXBFSYKRSCG-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-(naphthalen-2-ylmethoxy)benzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OCC=2C=C3C=CC=CC3=CC=2)CC1 QBPOXBFSYKRSCG-UHFFFAOYSA-N 0.000 claims 1
- OTOWMQMSNYAYKD-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(2,3-dimethoxyphenyl)methoxy]benzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OCC=2C(=C(OC)C=CC=2)OC)CC1 OTOWMQMSNYAYKD-UHFFFAOYSA-N 0.000 claims 1
- HRIGVVGEQBVIPZ-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(2-methoxyphenyl)methoxy]benzoate Chemical compound COC1=CC=CC=C1COC1=CC=CC=C1C(=O)OCCCN1CCN(C=2C(=CC=CC=2)OC)CC1 HRIGVVGEQBVIPZ-UHFFFAOYSA-N 0.000 claims 1
- JDVVAACDIZFFLP-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(3,4,5-trimethoxyphenyl)methoxy]benzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OCC=2C=C(OC)C(OC)=C(OC)C=2)CC1 JDVVAACDIZFFLP-UHFFFAOYSA-N 0.000 claims 1
- UOCTYYHETAKRBT-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(3,4-dimethoxyphenyl)methoxy]benzoate Chemical compound C1=C(OC)C(OC)=CC=C1COC1=CC=CC=C1C(=O)OCCCN1CCN(C=2C(=CC=CC=2)OC)CC1 UOCTYYHETAKRBT-UHFFFAOYSA-N 0.000 claims 1
- FDEYQKYHHUMCND-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(3-chlorophenyl)methoxy]benzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OCC=2C=C(Cl)C=CC=2)CC1 FDEYQKYHHUMCND-UHFFFAOYSA-N 0.000 claims 1
- HKZAQCOVJAHOGH-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(3-methoxyphenyl)methoxy]benzoate Chemical compound COC1=CC=CC(COC=2C(=CC=CC=2)C(=O)OCCCN2CCN(CC2)C=2C(=CC=CC=2)OC)=C1 HKZAQCOVJAHOGH-UHFFFAOYSA-N 0.000 claims 1
- NAURURJGHZIEGQ-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(4-chlorophenyl)methoxy]benzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OCC=2C=CC(Cl)=CC=2)CC1 NAURURJGHZIEGQ-UHFFFAOYSA-N 0.000 claims 1
- JGLDZESBTTXNQF-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(4-methoxyphenyl)methoxy]benzoate Chemical compound C1=CC(OC)=CC=C1COC1=CC=CC=C1C(=O)OCCCN1CCN(C=2C(=CC=CC=2)OC)CC1 JGLDZESBTTXNQF-UHFFFAOYSA-N 0.000 claims 1
- GFMTXZOBUKZIIJ-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-butoxybenzoate Chemical compound CCCCOC1=CC=CC=C1C(=O)OCCCN1CCN(C=2C(=CC=CC=2)OC)CC1 GFMTXZOBUKZIIJ-UHFFFAOYSA-N 0.000 claims 1
- LOWTVEZMWVZRDQ-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-hydroxybenzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)O)CC1 LOWTVEZMWVZRDQ-UHFFFAOYSA-N 0.000 claims 1
- BEZVHAFJMJRFEC-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-methoxy-3-propanoylbenzoate Chemical compound CCC(=O)C1=CC=CC(C(=O)OCCCN2CCN(CC2)C=2C(=CC=CC=2)OC)=C1OC BEZVHAFJMJRFEC-UHFFFAOYSA-N 0.000 claims 1
- KGPYDHAVECSIMS-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-methoxybenzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OC)CC1 KGPYDHAVECSIMS-UHFFFAOYSA-N 0.000 claims 1
- PIOAXUOGQPHLCE-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-octoxybenzoate Chemical compound CCCCCCCCOC1=CC=CC=C1C(=O)OCCCN1CCN(C=2C(=CC=CC=2)OC)CC1 PIOAXUOGQPHLCE-UHFFFAOYSA-N 0.000 claims 1
- CGZIHCWLQOSBNH-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-phenylmethoxy-3-propanoylbenzoate Chemical compound C=1C=CC=CC=1COC=1C(C(=O)CC)=CC=CC=1C(=O)OCCCN(CC1)CCN1C1=CC=CC=C1OC CGZIHCWLQOSBNH-UHFFFAOYSA-N 0.000 claims 1
- BOGDRDZUUKKNJD-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-phenylmethoxybenzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 BOGDRDZUUKKNJD-UHFFFAOYSA-N 0.000 claims 1
- UNRLZNFQGWRATL-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 3-phenylmethoxybenzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)CC1 UNRLZNFQGWRATL-UHFFFAOYSA-N 0.000 claims 1
- GLINTHNVHWWUBO-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 4-phenylmethoxybenzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC1 GLINTHNVHWWUBO-UHFFFAOYSA-N 0.000 claims 1
- QDOIMDKYVCVMAX-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl benzoate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C=CC=CC=2)CC1 QDOIMDKYVCVMAX-UHFFFAOYSA-N 0.000 claims 1
- DQPNOWIKCRZNGO-UHFFFAOYSA-N 3-acetyl-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenylmethoxybenzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=C(C(C)=O)C=CC=2)OCC=2C=CC=CC=2)CC1 DQPNOWIKCRZNGO-UHFFFAOYSA-N 0.000 claims 1
- HBTYNDOEAGLDKJ-UHFFFAOYSA-N ClC1=C(COC2=C(C(=O)OCCCN3CCN(CC3)C3=C(C=CC=C3)OC)C=CC=C2)C=CC=C1 Chemical compound ClC1=C(COC2=C(C(=O)OCCCN3CCN(CC3)C3=C(C=CC=C3)OC)C=CC=C2)C=CC=C1 HBTYNDOEAGLDKJ-UHFFFAOYSA-N 0.000 claims 1
- WPAQPNKUTGYZBL-UHFFFAOYSA-N [3-[4-(2-methoxyphenyl)piperazin-1-yl]-2,2-dimethylpropyl] 2-phenylmethoxybenzoate Chemical compound COC1=CC=CC=C1N1CCN(CC(C)(C)COC(=O)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 WPAQPNKUTGYZBL-UHFFFAOYSA-N 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- VQWYGPPXZYNTKC-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-(2-phenylethoxy)benzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OCCC=2C=CC=CC=2)CC1 VQWYGPPXZYNTKC-UHFFFAOYSA-N 0.000 claims 1
- ARCGZUMDHDLHTL-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-(2-phenylethyl)benzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)CCC=2C=CC=CC=2)CC1 ARCGZUMDHDLHTL-UHFFFAOYSA-N 0.000 claims 1
- TYSAUAUFBMPWKS-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-(3-phenylpropoxy)benzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OCCCC=2C=CC=CC=2)CC1 TYSAUAUFBMPWKS-UHFFFAOYSA-N 0.000 claims 1
- JRABLBKMLKLZHP-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-[(4-nitrophenyl)methoxy]-3-propanoylbenzamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC=1C(C(=O)CC)=CC=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC JRABLBKMLKLZHP-UHFFFAOYSA-N 0.000 claims 1
- HLSOMCBPSZEATN-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenoxybenzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OC=2C=CC=CC=2)CC1 HLSOMCBPSZEATN-UHFFFAOYSA-N 0.000 claims 1
- MTDYTLCAVMBOSO-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenylbenzenecarbothioamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=S)C=2C(=CC=CC=2)C=2C=CC=CC=2)CC1 MTDYTLCAVMBOSO-UHFFFAOYSA-N 0.000 claims 1
- OBWXSXTXAWCNEU-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenylmethoxy-3-propanoylbenzamide Chemical compound C=1C=CC=CC=1COC=1C(C(=O)CC)=CC=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC OBWXSXTXAWCNEU-UHFFFAOYSA-N 0.000 claims 1
- XXIZRVSZUPYQCB-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenylmethoxybenzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 XXIZRVSZUPYQCB-UHFFFAOYSA-N 0.000 claims 1
- BKHCLRYCKTWFPK-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-n-methyl-2-phenylmethoxybenzamide Chemical compound COC1=CC=CC=C1N1CCN(CCCN(C)C(=O)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 BKHCLRYCKTWFPK-UHFFFAOYSA-N 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 210000003708 urethra Anatomy 0.000 abstract description 11
- 230000036772 blood pressure Effects 0.000 abstract description 10
- 210000001635 urinary tract Anatomy 0.000 abstract description 8
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- IGNHXJKBXWDXCN-UHFFFAOYSA-N ethyl 2-[(4-benzoylphenyl)methoxy]-3-propanoylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CC)=C1OCC1=CC=C(C(=O)C=2C=CC=CC=2)C=C1 IGNHXJKBXWDXCN-UHFFFAOYSA-N 0.000 description 1
- ZEKWJUWSOPCHAX-UHFFFAOYSA-N ethyl 2-[(4-nitrophenyl)methoxy]-3-propanoylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CC)=C1OCC1=CC=C([N+]([O-])=O)C=C1 ZEKWJUWSOPCHAX-UHFFFAOYSA-N 0.000 description 1
- ZOXKFIKXBUYTAT-UHFFFAOYSA-N ethyl 2-phenylmethoxy-3-propanoylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CC)=C1OCC1=CC=CC=C1 ZOXKFIKXBUYTAT-UHFFFAOYSA-N 0.000 description 1
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- ZGWQDMTYAQEMHA-UHFFFAOYSA-N hydron;1-(2-methoxyphenyl)piperazine;dichloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCNCC1 ZGWQDMTYAQEMHA-UHFFFAOYSA-N 0.000 description 1
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- 150000002513 isocyanates Chemical class 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 238000002350 laparotomy Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- AXDHBRGCYBYEIQ-UHFFFAOYSA-N methanesulfonic acid 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-(cyclohexylmethoxy)benzoate Chemical compound CS(O)(=O)=O.COc1ccccc1N1CCN(CCCOC(=O)c2ccccc2OCC2CCCCC2)CC1 AXDHBRGCYBYEIQ-UHFFFAOYSA-N 0.000 description 1
- CBDMMHDXQGVKTD-UHFFFAOYSA-N methanesulfonic acid 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-[(3-chlorophenyl)methoxy]benzoate Chemical compound CS(O)(=O)=O.COc1ccccc1N1CCN(CCCOC(=O)c2ccccc2OCc2cccc(Cl)c2)CC1 CBDMMHDXQGVKTD-UHFFFAOYSA-N 0.000 description 1
- KXXBQIZJYIRMAQ-UHFFFAOYSA-N methanesulfonic acid;3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-butoxybenzoate;hydrate Chemical compound O.CS(O)(=O)=O.CCCCOC1=CC=CC=C1C(=O)OCCCN1CCN(C=2C(=CC=CC=2)OC)CC1 KXXBQIZJYIRMAQ-UHFFFAOYSA-N 0.000 description 1
- FSSBUGDTWFPMHJ-UHFFFAOYSA-N methanesulfonic acid;3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 2-octoxybenzoate;hydrate Chemical compound O.CS(O)(=O)=O.CCCCCCCCOC1=CC=CC=C1C(=O)OCCCN1CCN(C=2C(=CC=CC=2)OC)CC1 FSSBUGDTWFPMHJ-UHFFFAOYSA-N 0.000 description 1
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 1
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- NHBCLFAZPVRVEI-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-phenylmethoxybenzamide Chemical compound OCCCNC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 NHBCLFAZPVRVEI-UHFFFAOYSA-N 0.000 description 1
- AWQZXFXPFDVNHN-UHFFFAOYSA-N n-[3-[4-(2-hydroxyphenyl)piperazin-1-yl]propyl]-2-phenylmethoxybenzamide;hydrochloride Chemical compound Cl.OC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 AWQZXFXPFDVNHN-UHFFFAOYSA-N 0.000 description 1
- HTCGAFKPCOYMND-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-(2-phenylethyl)benzamide;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)CCC=2C=CC=CC=2)CC1 HTCGAFKPCOYMND-UHFFFAOYSA-N 0.000 description 1
- TWHKSTXYHUSXHT-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-[(4-nitrophenyl)methoxy]-3-propanoylbenzamide;hydrate;dihydrochloride Chemical compound O.Cl.Cl.C=1C=C([N+]([O-])=O)C=CC=1COC=1C(C(=O)CC)=CC=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC TWHKSTXYHUSXHT-UHFFFAOYSA-N 0.000 description 1
- DBYRYRXLZINFPE-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C(=CC=CC=2)OC=2C=CC=CC=2)CC1 DBYRYRXLZINFPE-UHFFFAOYSA-N 0.000 description 1
- SWLJWYLEUBJKKX-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenylbenzenecarbothioamide;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCCNC(=S)C=2C(=CC=CC=2)C=2C=CC=CC=2)CC1 SWLJWYLEUBJKKX-UHFFFAOYSA-N 0.000 description 1
- OFKOWPYVTCPFTG-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-phenylmethoxy-3-propanoylbenzamide;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1COC=1C(C(=O)CC)=CC=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC OFKOWPYVTCPFTG-UHFFFAOYSA-N 0.000 description 1
- MNEPOBSTKGSSDU-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-n-methyl-2-phenylmethoxybenzamide;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCCN(C)C(=O)C=2C(=CC=CC=2)OCC=2C=CC=CC=2)CC1 MNEPOBSTKGSSDU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
- 229960001999 phentolamine Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650952—Six-membered rings having the nitrogen atoms in the positions 1 and 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Composés répondant à la formule générale (I), dans laquelle Y représente un groupe de liaison, choisi dans une large gamme, mais comprenant -COO-, -CH2COO-, -CONH-, -CON(CH3)-, -CH2CONH-, SO2NH-, -SO2N(CH3)- et -PO(OC2H5)NH-; W représente une chaîne alkylène; A représente un groupe phénylique substitué ou un groupe benzofurane ou benzodioxane; et R et R1 peuvent avoir plusieurs valeurs, mais R est de préférence un groupe volumineux. Ces composés et leurs promédicaments, énantiomères, diastéréoisomères, N-oxydes et leurs sels pharmaceutiquement acceptables bloquent les récepteurs alpha 1a-adrénergiques et sont de ce fait utilisables dans la prophylaxie des contractions de la prostate, de l'urètre et de la partie inférieure du tractus urinaire, et ce sans intervenir sur la tension artérielle.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT93MI001717A IT1266582B1 (it) | 1993-07-30 | 1993-07-30 | Derivati (di)azacicloesanici e diazacicloeptanici |
ITMI93A001717 | 1993-07-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2168443A1 true CA2168443A1 (fr) | 1995-02-09 |
Family
ID=11366733
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002168443A Abandoned CA2168443A1 (fr) | 1993-07-30 | 1994-07-22 | Derives de la piperazine, antagonistes du recepteur .alpha.1a-adrenergique |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0711288A1 (fr) |
JP (1) | JPH09500883A (fr) |
KR (1) | KR960703884A (fr) |
CN (1) | CN1132508A (fr) |
AU (1) | AU680037B2 (fr) |
CA (1) | CA2168443A1 (fr) |
IL (1) | IL110348A0 (fr) |
IT (1) | IT1266582B1 (fr) |
MX (1) | MXPA94005805A (fr) |
NO (1) | NO960371L (fr) |
NZ (1) | NZ271634A (fr) |
SG (1) | SG46281A1 (fr) |
WO (1) | WO1995004049A1 (fr) |
ZA (1) | ZA945625B (fr) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5620993A (en) * | 1995-06-07 | 1997-04-15 | Merck & Co., Inc. | Alpha-1a adrenergic receptor antagonists |
US5661163A (en) * | 1995-06-07 | 1997-08-26 | Merck & Co., Inc. | Alpha-1a adrenergic receptor antagonists |
US5659033A (en) * | 1995-09-13 | 1997-08-19 | Neurogen Corporation | N-aminoalkylfluorenecarboxamides; a new class of dopamine receptor subtype specific ligands |
US5807856A (en) * | 1995-11-15 | 1998-09-15 | Merck & Co., Inc. | Alpha 1a adrenergic receptor antagonist |
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US2997472A (en) * | 1961-08-22 | Certificate of correction | ||
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-
1993
- 1993-07-30 IT IT93MI001717A patent/IT1266582B1/it active IP Right Grant
-
1994
- 1994-07-18 IL IL11034894A patent/IL110348A0/xx unknown
- 1994-07-22 KR KR1019960700460A patent/KR960703884A/ko not_active Application Discontinuation
- 1994-07-22 JP JP7505546A patent/JPH09500883A/ja active Pending
- 1994-07-22 WO PCT/EP1994/002437 patent/WO1995004049A1/fr not_active Application Discontinuation
- 1994-07-22 SG SG1996002067A patent/SG46281A1/en unknown
- 1994-07-22 AU AU75323/94A patent/AU680037B2/en not_active Ceased
- 1994-07-22 CN CN94193622A patent/CN1132508A/zh active Pending
- 1994-07-22 CA CA002168443A patent/CA2168443A1/fr not_active Abandoned
- 1994-07-22 EP EP94925382A patent/EP0711288A1/fr not_active Withdrawn
- 1994-07-22 NZ NZ271634A patent/NZ271634A/en unknown
- 1994-07-29 ZA ZA945625A patent/ZA945625B/xx unknown
- 1994-07-29 MX MXPA94005805A patent/MXPA94005805A/es unknown
-
1996
- 1996-01-29 NO NO960371A patent/NO960371L/no unknown
Also Published As
Publication number | Publication date |
---|---|
ITMI931717A0 (it) | 1993-07-30 |
AU7532394A (en) | 1995-02-28 |
EP0711288A1 (fr) | 1996-05-15 |
JPH09500883A (ja) | 1997-01-28 |
IT1266582B1 (it) | 1997-01-09 |
NO960371L (no) | 1996-03-29 |
NZ271634A (en) | 1996-09-25 |
NO960371D0 (no) | 1996-01-29 |
CN1132508A (zh) | 1996-10-02 |
ITMI931717A1 (it) | 1995-01-30 |
WO1995004049A1 (fr) | 1995-02-09 |
AU680037B2 (en) | 1997-07-17 |
SG46281A1 (en) | 1998-02-20 |
KR960703884A (ko) | 1996-08-31 |
MXPA94005805A (es) | 2004-08-20 |
ZA945625B (en) | 1995-03-07 |
IL110348A0 (en) | 1994-10-21 |
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