JP2003501424A5 - - Google Patents
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- Publication number
- JP2003501424A5 JP2003501424A5 JP2001502413A JP2001502413A JP2003501424A5 JP 2003501424 A5 JP2003501424 A5 JP 2003501424A5 JP 2001502413 A JP2001502413 A JP 2001502413A JP 2001502413 A JP2001502413 A JP 2001502413A JP 2003501424 A5 JP2003501424 A5 JP 2003501424A5
- Authority
- JP
- Japan
- Prior art keywords
- ethoxy
- piperidin
- indol
- ethyl
- benzoic acid
- 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.)
- Ceased
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- -1 alkylenethio Chemical group 0.000 description 41
- 239000005711 Benzoic acid Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000005529 alkyleneoxy group Chemical group 0.000 description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- QIRDLEIUOYJRGZ-UHFFFAOYSA-N 2-methyl-2-[4-[4-[4-[1-(3-methylbutyl)indol-3-yl]piperidin-1-yl]butanoyl]phenyl]propanoic acid Chemical compound C12=CC=CC=C2N(CCC(C)C)C=C1C(CC1)CCN1CCCC(=O)C1=CC=C(C(C)(C)C(O)=O)C=C1 QIRDLEIUOYJRGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- YGMUXTWULKXKAO-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-[1-[3-[2-(2h-tetrazol-5-yl)phenoxy]propyl]piperidin-4-yl]indole Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCCOC1=CC=CC=C1C=1N=NNN=1 YGMUXTWULKXKAO-UHFFFAOYSA-N 0.000 description 1
- DUCZGLRXKNHEME-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-[1-[3-[4-(2h-tetrazol-5-yl)phenoxy]propyl]piperidin-4-yl]indole Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCCOC(C=C1)=CC=C1C=1N=NNN=1 DUCZGLRXKNHEME-UHFFFAOYSA-N 0.000 description 1
- QCFSNBWEJWOEPW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-piperidin-4-ylindole Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C1CCNCC1 QCFSNBWEJWOEPW-UHFFFAOYSA-N 0.000 description 1
- ISRNSOPKRJFRMR-UHFFFAOYSA-N 1-(3-methylbutyl)-3-[1-[3-[2-(2h-tetrazol-5-yl)phenoxy]propyl]piperidin-4-yl]indole Chemical compound C12=CC=CC=C2N(CCC(C)C)C=C1C(CC1)CCN1CCCOC1=CC=CC=C1C=1N=NNN=1 ISRNSOPKRJFRMR-UHFFFAOYSA-N 0.000 description 1
- ZDRUIODKMKJGOJ-UHFFFAOYSA-N 1-(3-methylbutyl)-3-[1-[3-[4-(2h-tetrazol-5-yl)phenoxy]propyl]piperidin-4-yl]indole Chemical compound C12=CC=CC=C2N(CCC(C)C)C=C1C(CC1)CCN1CCCOC(C=C1)=CC=C1C=1N=NNN=1 ZDRUIODKMKJGOJ-UHFFFAOYSA-N 0.000 description 1
- NKNYSGLYIJGMTP-UHFFFAOYSA-N 2-[2-[4-(1-butylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O NKNYSGLYIJGMTP-UHFFFAOYSA-N 0.000 description 1
- ZSHYMGAUWNATNK-UHFFFAOYSA-N 2-[2-[4-(1-heptylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCCCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O ZSHYMGAUWNATNK-UHFFFAOYSA-N 0.000 description 1
- VMEWUJUJGKNDJZ-UHFFFAOYSA-N 2-[2-[4-(1-hexylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O VMEWUJUJGKNDJZ-UHFFFAOYSA-N 0.000 description 1
- MRFSVLXYLQZTHT-UHFFFAOYSA-N 2-[2-[4-(1-pentylindol-3-yl)piperidin-1-yl]ethoxy]acetic acid Chemical compound C12=CC=CC=C2N(CCCCC)C=C1C1CCN(CCOCC(O)=O)CC1 MRFSVLXYLQZTHT-UHFFFAOYSA-N 0.000 description 1
- KTEZZEXASTZNJG-UHFFFAOYSA-N 2-[2-[4-(1-prop-2-enylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC=C)C=2)CC1 KTEZZEXASTZNJG-UHFFFAOYSA-N 0.000 description 1
- OJZFCJFQRDSGQX-UHFFFAOYSA-N 2-[2-[4-(1-prop-2-ynylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC#C)C=2)CC1 OJZFCJFQRDSGQX-UHFFFAOYSA-N 0.000 description 1
- MLJHIRXKQLQHRL-UHFFFAOYSA-N 2-[2-[4-(1-propylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O MLJHIRXKQLQHRL-UHFFFAOYSA-N 0.000 description 1
- QLHLGBNHXMZIQT-UHFFFAOYSA-N 2-[2-[4-(1h-indol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3NC=2)CC1 QLHLGBNHXMZIQT-UHFFFAOYSA-N 0.000 description 1
- HHITYXUJELSBPS-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-4-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O HHITYXUJELSBPS-UHFFFAOYSA-N 0.000 description 1
- SPOKTOSVUQLTOH-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-4-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O SPOKTOSVUQLTOH-UHFFFAOYSA-N 0.000 description 1
- QAZVGNJWLJEDFV-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-4-fluoroindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O QAZVGNJWLJEDFV-UHFFFAOYSA-N 0.000 description 1
- QMFNTTFIGWXQNY-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O QMFNTTFIGWXQNY-UHFFFAOYSA-N 0.000 description 1
- NDRPQPJPFUMFQZ-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O NDRPQPJPFUMFQZ-UHFFFAOYSA-N 0.000 description 1
- INVVRCPLVVQOGS-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O INVVRCPLVVQOGS-UHFFFAOYSA-N 0.000 description 1
- DGVYELQBTIBCMU-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-fluoroindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC(F)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O DGVYELQBTIBCMU-UHFFFAOYSA-N 0.000 description 1
- HOLMXWXLIIOTTC-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-methoxyindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC(OC)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O HOLMXWXLIIOTTC-UHFFFAOYSA-N 0.000 description 1
- AARSYHRXVGSQHM-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-methoxyindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC(OC)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O AARSYHRXVGSQHM-UHFFFAOYSA-N 0.000 description 1
- WYMUGVSTXZEYIJ-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-methoxyindol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC(OC)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O WYMUGVSTXZEYIJ-UHFFFAOYSA-N 0.000 description 1
- ZEARTZKNFQZDKX-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-5-methoxyindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC(OC)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O ZEARTZKNFQZDKX-UHFFFAOYSA-N 0.000 description 1
- WYMKMMPHJBIHRY-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O WYMKMMPHJBIHRY-UHFFFAOYSA-N 0.000 description 1
- KGKISXJBNCHPAU-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O KGKISXJBNCHPAU-UHFFFAOYSA-N 0.000 description 1
- XUQURAFGTLVXHN-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O XUQURAFGTLVXHN-UHFFFAOYSA-N 0.000 description 1
- BVRIYQUZSCWOSG-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=C(F)C=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O BVRIYQUZSCWOSG-UHFFFAOYSA-N 0.000 description 1
- WUAPZVZDCHYLGI-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-7-methylindol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC=CC(C)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O WUAPZVZDCHYLGI-UHFFFAOYSA-N 0.000 description 1
- WIQGPOWORKUTND-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)-7-methylindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC(C)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O WIQGPOWORKUTND-UHFFFAOYSA-N 0.000 description 1
- XUYOZHRTHKAKTL-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O XUYOZHRTHKAKTL-UHFFFAOYSA-N 0.000 description 1
- FGOSLGBBJZIYHE-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-6-fluorobenzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(F)=C1C(O)=O FGOSLGBBJZIYHE-UHFFFAOYSA-N 0.000 description 1
- JESNEQBROSADIH-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]acetic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C1CCN(CCOCC(O)=O)CC1 JESNEQBROSADIH-UHFFFAOYSA-N 0.000 description 1
- QSOACFIAXDGTQW-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O QSOACFIAXDGTQW-UHFFFAOYSA-N 0.000 description 1
- OBUAFUJPNYUMEW-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethylsulfanyl]acetic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C1CCN(CCSCC(O)=O)CC1 OBUAFUJPNYUMEW-UHFFFAOYSA-N 0.000 description 1
- LVAJRQDSXRFOTR-UHFFFAOYSA-N 2-[2-[4-[1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O LVAJRQDSXRFOTR-UHFFFAOYSA-N 0.000 description 1
- OSFBNDLQBDNFRN-UHFFFAOYSA-N 2-[2-[4-[1-(2-methylpropyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CC(C)C)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O OSFBNDLQBDNFRN-UHFFFAOYSA-N 0.000 description 1
- XEQHNEYQMZPAAB-UHFFFAOYSA-N 2-[2-[4-[1-(2-prop-2-ynoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CCOCC#C)C=2)CC1 XEQHNEYQMZPAAB-UHFFFAOYSA-N 0.000 description 1
- ILRDUQNXVKDHAM-UHFFFAOYSA-N 2-[2-[4-[1-(2-propoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O ILRDUQNXVKDHAM-UHFFFAOYSA-N 0.000 description 1
- VPOAVKKIGBXDMV-UHFFFAOYSA-N 2-[2-[4-[1-(3-methoxypropyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCOC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O VPOAVKKIGBXDMV-UHFFFAOYSA-N 0.000 description 1
- NYQGYEGBQNANJM-UHFFFAOYSA-N 2-[2-[4-[1-(3-methylbutyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCC(C)C)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O NYQGYEGBQNANJM-UHFFFAOYSA-N 0.000 description 1
- YTJIIMFPVVISHG-UHFFFAOYSA-N 2-[2-[4-[1-(cyclohexylmethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC3CCCCC3)C=2)CC1 YTJIIMFPVVISHG-UHFFFAOYSA-N 0.000 description 1
- PKDGHGYNWFKPAF-UHFFFAOYSA-N 2-[2-[4-[1-(cyclopropylmethyl)-6-fluoroindol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=C(F)C=C3N(CC3CC3)C=2)CC1 PKDGHGYNWFKPAF-UHFFFAOYSA-N 0.000 description 1
- VBXUDFDAMGGOQA-UHFFFAOYSA-N 2-[2-[4-[1-(cyclopropylmethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC3CC3)C=2)CC1 VBXUDFDAMGGOQA-UHFFFAOYSA-N 0.000 description 1
- MIPYJZXZGANVJL-UHFFFAOYSA-N 2-[2-[4-[1-[(4-fluorophenyl)methyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC=3C=CC(F)=CC=3)C=2)CC1 MIPYJZXZGANVJL-UHFFFAOYSA-N 0.000 description 1
- VJYYJODZGYTFFM-UHFFFAOYSA-N 2-[2-[4-[1-[(4-methoxyphenyl)methyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=CC=C2C(C2CCN(CCOC=3C(=CC=CC=3)C(O)=O)CC2)=C1 VJYYJODZGYTFFM-UHFFFAOYSA-N 0.000 description 1
- NMUSDIXZEJLCTH-UHFFFAOYSA-N 2-[2-[4-[1-[(4-phenylmethoxyphenyl)methyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CC=C3N(CC=3C=CC(OCC=4C=CC=CC=4)=CC=3)C=2)CC1 NMUSDIXZEJLCTH-UHFFFAOYSA-N 0.000 description 1
- VGRHRQOHLGEVIC-UHFFFAOYSA-N 2-[2-[4-[1-[(4-tert-butylphenyl)methyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1CN1C2=CC=CC=C2C(C2CCN(CCOC=3C(=CC=CC=3)C(O)=O)CC2)=C1 VGRHRQOHLGEVIC-UHFFFAOYSA-N 0.000 description 1
- XRPDEOQYHIZYNY-UHFFFAOYSA-N 2-[2-[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]ethoxy]acetic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C1CCN(CCOCC(O)=O)CC1 XRPDEOQYHIZYNY-UHFFFAOYSA-N 0.000 description 1
- DTEVHRPFQBKFKZ-UHFFFAOYSA-N 2-[2-[4-[1-[2-(4-methoxyphenyl)ethyl]indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C1=CC(OC)=CC=C1CCN1C2=CC=CC=C2C(C2CCN(CCOC=3C(=CC=CC=3)C(O)=O)CC2)=C1 DTEVHRPFQBKFKZ-UHFFFAOYSA-N 0.000 description 1
- KMVMABDALRFKCM-UHFFFAOYSA-N 2-[2-[4-[4-fluoro-1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O KMVMABDALRFKCM-UHFFFAOYSA-N 0.000 description 1
- PLUCWLKTQPYMOJ-UHFFFAOYSA-N 2-[2-[4-[4-fluoro-1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-5-methylbenzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC=C(C)C=C1C(O)=O PLUCWLKTQPYMOJ-UHFFFAOYSA-N 0.000 description 1
- DGEZDVIEJXDCQA-UHFFFAOYSA-N 2-[2-[4-[4-fluoro-1-(2-methoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=C(F)C=CC=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O DGEZDVIEJXDCQA-UHFFFAOYSA-N 0.000 description 1
- MWHMBIYNCCYPQI-UHFFFAOYSA-N 2-[2-[4-[5-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC(Br)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O MWHMBIYNCCYPQI-UHFFFAOYSA-N 0.000 description 1
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| ES9901232 | 1999-06-04 | ||
| PCT/EP2000/005010 WO2000075130A1 (en) | 1999-06-04 | 2000-05-31 | Indolylpiperidine derivatives as antihistaminic and antiallergic agents |
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| JP2003501424A JP2003501424A (ja) | 2003-01-14 |
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| EP (1) | EP1183251B1 (https=) |
| JP (1) | JP2003501424A (https=) |
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| BR (1) | BR0011340A (https=) |
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| US6864219B2 (en) | 2000-01-17 | 2005-03-08 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| ES2172436B1 (es) * | 2000-10-31 | 2004-01-16 | Almirall Prodesfarma Sa | Derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| AU2002243394A1 (en) * | 2000-11-16 | 2002-06-24 | Wyeth | Aryloxy piperidinyl derivatives for the treatment of depression |
| ES2201899B1 (es) * | 2002-04-01 | 2005-06-01 | Almirall Prodesfarma, S.A. | Derivados de la azaindolilpiperidina como agentes antihistaminicos y antialergicos. |
| ES2201907B1 (es) * | 2002-05-29 | 2005-06-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de indolilpiperidina como potentes agentes antihistaminicos y antialergicos. |
| RU2382037C2 (ru) * | 2003-11-17 | 2010-02-20 | Бёрингер Ингельхайм Интернациональ Гмбх | Новые пиперидинзамещенные индолы или их гетеропроизводные |
| US20050245540A1 (en) * | 2003-12-09 | 2005-11-03 | Fujisawa Pharmaceutical Co., Ltd. | New methods |
| EA015517B1 (ru) * | 2004-04-13 | 2011-08-30 | Инсайт Корпорейшн | Производные пиперазинилпиперидина в качестве антагонистов хемокинового рецептора |
| WO2006002350A1 (en) * | 2004-06-24 | 2006-01-05 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| US8071624B2 (en) | 2004-06-24 | 2011-12-06 | Incyte Corporation | N-substituted piperidines and their use as pharmaceuticals |
| AU2006239302B2 (en) * | 2005-04-26 | 2011-07-07 | Hypnion, Inc. | Benzisoxazole piperazine compounds and methods of use thereof |
| ATE531706T1 (de) | 2005-04-30 | 2011-11-15 | Boehringer Ingelheim Int | Neue piperidin-substituierte indole und ihre verwendung als ccr-3-modulatoren |
| US20060275516A1 (en) * | 2005-06-02 | 2006-12-07 | Ram A N S | Compositions and methods for the treatment of allergic rhinitis |
| WO2008030853A2 (en) * | 2006-09-06 | 2008-03-13 | Incyte Corporation | Combination therapy for human immunodeficiency virus infection |
| EP2079725B1 (en) * | 2006-10-27 | 2011-12-14 | Boehringer Ingelheim International GmbH | Piperidyl-propane-thiol ccr3 modulators |
| CA2681162C (en) | 2007-03-15 | 2015-11-24 | Novartis Ag | Benzyl and pyridine derivatives as modulators of hedgehog pathway |
| US20100041663A1 (en) | 2008-07-18 | 2010-02-18 | Novartis Ag | Organic Compounds as Smo Inhibitors |
| CN101560179B (zh) * | 2009-05-25 | 2012-04-18 | 浙江大学 | 具有h3受体亲和能力的含氮吲哚衍生物和用途 |
| CN101747321B (zh) * | 2009-12-22 | 2013-01-02 | 浙江大学 | 吲哚-3-苄胺衍生物及制备方法和用途 |
| EP3040334A1 (en) * | 2014-12-29 | 2016-07-06 | Faes Farma, S.A. | New benzimidazole derivatives as antihistamine agents |
| PE20241304A1 (es) * | 2021-07-30 | 2024-06-24 | Confo Therapeutics N V | Compuestos para el tratamiento del dolor, en particular el dolor neuropatico, y/u otras enfermedades o trastornos que se asocian con at2r y/o senalizacion mediada por at2r |
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| US4742057A (en) * | 1985-12-05 | 1988-05-03 | Fujisawa Pharmaceutical Co., Ltd. | Antiallergic thiazole compounds |
| JPS63301881A (ja) * | 1987-06-01 | 1988-12-08 | Fujisawa Pharmaceut Co Ltd | インドリルピペリジン誘導体 |
| DK733788A (da) * | 1988-01-14 | 1989-07-15 | Fujisawa Pharmaceutical Co | Indolylpiperidinderivater og fremgangsmaade til fremstilling deraf |
| GB8800795D0 (en) * | 1988-01-14 | 1988-02-17 | Fujisawa Pharmaceutical Co | New indolylpiperidine compounds processes for preparations thereof & pharmaceutical composition comprising same |
| GB8900382D0 (en) * | 1989-01-09 | 1989-03-08 | Janssen Pharmaceutica Nv | 2-aminopyrimidinone derivatives |
| PH30434A (en) * | 1989-04-07 | 1997-05-09 | Janssen Pharmaceutica Nv | Hydroxyalkylfuranyl derivatives |
| NZ249286A (en) * | 1992-02-13 | 1996-02-27 | Merrell Dow Pharma | Piperidine-4-ylmethyl thiophene and thiazole derivatives and pharmaceutical compositions |
| IT1271417B (it) * | 1993-10-15 | 1997-05-28 | Erregierre Ind Chim | Composti ad attivita' antiistaminica procedimento per la loro preperazione e composizioni farmaceutiche che li contengono. |
| DE19500689A1 (de) | 1995-01-12 | 1996-07-18 | Merck Patent Gmbh | Indolpiperidin-Derivate |
| DE19707628A1 (de) | 1997-02-26 | 1998-08-27 | Merck Patent Gmbh | Oxazolidinone |
| AR013669A1 (es) * | 1997-10-07 | 2001-01-10 | Smithkline Beecham Corp | Compuestos y metodos |
| AR028685A1 (es) * | 2000-06-14 | 2003-05-21 | Lundbeck & Co As H | Derivados de indol |
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1999
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2000
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- 2000-05-31 ES ES00940296T patent/ES2211559T3/es not_active Expired - Lifetime
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- 2000-05-31 BR BR0011340-9A patent/BR0011340A/pt not_active Application Discontinuation
- 2000-05-31 DK DK00940296T patent/DK1183251T3/da active
- 2000-05-31 HK HK02102119.0A patent/HK1040990A1/zh unknown
- 2000-05-31 HU HU0203320A patent/HUP0203320A3/hu unknown
- 2000-05-31 TR TR2001/03490T patent/TR200103490T2/xx unknown
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- 2000-05-31 UA UA2001118222A patent/UA72517C2/uk unknown
- 2000-05-31 JP JP2001502413A patent/JP2003501424A/ja not_active Ceased
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- 2000-05-31 CA CA002375985A patent/CA2375985A1/en not_active Abandoned
- 2000-05-31 CZ CZ20014334A patent/CZ20014334A3/cs unknown
- 2000-05-31 PE PE2000000524A patent/PE20010208A1/es not_active Application Discontinuation
- 2000-05-31 EP EP00940296A patent/EP1183251B1/en not_active Expired - Lifetime
- 2000-05-31 DE DE2000608239 patent/DE60008239T2/de not_active Expired - Lifetime
- 2000-05-31 PT PT00940296T patent/PT1183251E/pt unknown
- 2000-05-31 NZ NZ515649A patent/NZ515649A/en unknown
- 2000-05-31 AU AU55276/00A patent/AU773164B2/en not_active Ceased
- 2000-05-31 CN CNB008112819A patent/CN1191246C/zh not_active Expired - Fee Related
- 2000-06-02 TW TW089110816A patent/TWI226889B/zh not_active IP Right Cessation
- 2000-06-02 AR ARP000102755A patent/AR029640A1/es not_active Application Discontinuation
- 2000-06-02 CO CO00041546A patent/CO5180556A1/es not_active Application Discontinuation
-
2001
- 2001-11-23 ZA ZA200109676A patent/ZA200109676B/en unknown
- 2001-12-03 BG BG106168A patent/BG106168A/bg unknown
- 2001-12-03 NO NO20015897A patent/NO20015897L/no not_active Application Discontinuation
- 2001-12-04 US US10/006,416 patent/US6683096B2/en not_active Expired - Fee Related
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