ZA200109676B - Indolylpiperidine derivatives as antihistaminic and anti-allergic agents. - Google Patents
Indolylpiperidine derivatives as antihistaminic and anti-allergic agents. Download PDFInfo
- Publication number
- ZA200109676B ZA200109676B ZA200109676A ZA200109676A ZA200109676B ZA 200109676 B ZA200109676 B ZA 200109676B ZA 200109676 A ZA200109676 A ZA 200109676A ZA 200109676 A ZA200109676 A ZA 200109676A ZA 200109676 B ZA200109676 B ZA 200109676B
- Authority
- ZA
- South Africa
- Prior art keywords
- ethoxy
- piperidin
- indol
- ethyl
- benzoic acid
- Prior art date
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- 239000000739 antihistaminic agent Substances 0.000 title claims description 7
- 230000001387 anti-histamine Effects 0.000 title claims description 5
- HNQZRUDJRPSFAU-UHFFFAOYSA-N 2-piperidin-1-yl-1h-indole Chemical class C1CCCCN1C1=CC2=CC=CC=C2N1 HNQZRUDJRPSFAU-UHFFFAOYSA-N 0.000 title description 11
- 239000000043 antiallergic agent Substances 0.000 title description 5
- -1 alkylenethio Chemical group 0.000 claims description 80
- 239000005711 Benzoic acid Substances 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 206010010741 Conjunctivitis Diseases 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 208000024780 Urticaria Diseases 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002560 nitrile group Chemical group 0.000 claims description 4
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- 206010048768 Dermatosis Diseases 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000003266 anti-allergic effect Effects 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 3
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 206010039083 rhinitis Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 210000000748 cardiovascular system Anatomy 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 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 claims 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 claims 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 claims 1
- WBMYDORIDCSVSO-UHFFFAOYSA-N 2-[2-[4-(1-pentylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O WBMYDORIDCSVSO-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 1
- GGZYFZOALZISQV-UHFFFAOYSA-N 2-[2-[4-[1-(2-propan-2-yloxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOC(C)C)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O GGZYFZOALZISQV-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 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 claims 1
- XADGZRXEEIMQPN-UHFFFAOYSA-N 2-[2-[4-[5-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC(Br)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O XADGZRXEEIMQPN-UHFFFAOYSA-N 0.000 claims 1
- BLKUTSXBXNFUNN-UHFFFAOYSA-N 2-[2-[4-[5-chloro-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC(Cl)=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O BLKUTSXBXNFUNN-UHFFFAOYSA-N 0.000 claims 1
- QWQRGXJHFQEOOM-UHFFFAOYSA-N 2-[2-[4-[7-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC(Br)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O QWQRGXJHFQEOOM-UHFFFAOYSA-N 0.000 claims 1
- HIKYNJRMLYWZMO-UHFFFAOYSA-N 2-[3-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]propoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCCOC1=CC=CC=C1C(O)=O HIKYNJRMLYWZMO-UHFFFAOYSA-N 0.000 claims 1
- PBVWEHJOAGLFKQ-UHFFFAOYSA-N 2-[4-[1-hydroxy-4-[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]butyl]phenyl]-2-methylpropanoic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C(CC1)CCN1CCCC(O)C1=CC=C(C(C)(C)C(O)=O)C=C1 PBVWEHJOAGLFKQ-UHFFFAOYSA-N 0.000 claims 1
- DXTGTULLPMCNRT-UHFFFAOYSA-N 2-[4-[3-[4-[1-(cyclopropylmethyl)indol-3-yl]piperidin-1-yl]propoxy]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCCCN1CCC(C=2C3=CC=CC=C3N(CC3CC3)C=2)CC1 DXTGTULLPMCNRT-UHFFFAOYSA-N 0.000 claims 1
- MBKSDCJSGRTHKE-UHFFFAOYSA-N 2-[4-[4-[4-[1-(cyclopropylmethyl)indol-3-yl]piperidin-1-yl]butanoyl]phenyl]-2-methylpropanoic acid Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(=O)CCCN1CCC(C=2C3=CC=CC=C3N(CC3CC3)C=2)CC1 MBKSDCJSGRTHKE-UHFFFAOYSA-N 0.000 claims 1
- VPOOFOBSBKIDGC-UHFFFAOYSA-N 3,5-dibromo-2-[2-[4-[7-bromo-1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC(Br)=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=C(Br)C=C(Br)C=C1C(O)=O VPOOFOBSBKIDGC-UHFFFAOYSA-N 0.000 claims 1
- MPAATGOJVRZGQG-UHFFFAOYSA-N 3-[2-[4-(1-pentylindol-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCCCC)C=C1C(CC1)CCN1CCOC1=CC=CC(C(O)=O)=C1 MPAATGOJVRZGQG-UHFFFAOYSA-N 0.000 claims 1
- JVNUOKPJEVOUFJ-UHFFFAOYSA-N 3-[3-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]propoxy]benzoic acid 3-[3-[4-(1-pentylindol-3-yl)piperidin-1-yl]propoxy]benzoic acid Chemical compound CCCCCn1cc(C2CCN(CCCOc3cccc(c3)C(O)=O)CC2)c2ccccc12.CCOCCn1cc(C2CCN(CCCOc3cccc(c3)C(O)=O)CC2)c2ccccc12 JVNUOKPJEVOUFJ-UHFFFAOYSA-N 0.000 claims 1
- QWEBBOUXWRCKQN-UHFFFAOYSA-N 3-[3-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]propoxy]propanoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C1CCN(CCCOCCC(O)=O)CC1 QWEBBOUXWRCKQN-UHFFFAOYSA-N 0.000 claims 1
- SKMBWBBUAOZVEG-UHFFFAOYSA-N 3-[4-(1-pentylindol-3-yl)piperidin-1-yl]propanoic acid Chemical compound C12=CC=CC=C2N(CCCCC)C=C1C1CCN(CCC(O)=O)CC1 SKMBWBBUAOZVEG-UHFFFAOYSA-N 0.000 claims 1
- ZJDCJZOQZJFGQK-UHFFFAOYSA-N 3-[4-[2-[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]ethyl]phenyl]propanoic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CCC1=CC=C(CCC(O)=O)C=C1 ZJDCJZOQZJFGQK-UHFFFAOYSA-N 0.000 claims 1
- OTCPYGJWSZHDTB-UHFFFAOYSA-N 3-[[4-[1-(cyclopropylmethyl)indol-3-yl]piperidin-1-yl]methyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CN2CCC(CC2)C=2C3=CC=CC=C3N(CC3CC3)C=2)=C1 OTCPYGJWSZHDTB-UHFFFAOYSA-N 0.000 claims 1
- GZMZUFPMBUYDFX-UHFFFAOYSA-N 4-[3-[4-[1-[2-(2-methoxyethoxy)ethyl]indol-3-yl]piperidin-1-yl]propoxy]benzoic acid Chemical compound C12=CC=CC=C2N(CCOCCOC)C=C1C(CC1)CCN1CCCOC1=CC=C(C(O)=O)C=C1 GZMZUFPMBUYDFX-UHFFFAOYSA-N 0.000 claims 1
- UZLXEGUTODDCEO-UHFFFAOYSA-N 5-[[4-[1-(2-ethoxyethyl)indol-3-yl]piperidin-1-yl]methyl]furan-2-carboxylic acid;5-[[4-[1-[(4-fluorophenyl)methyl]indol-3-yl]piperidin-1-yl]methyl]furan-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CCOCC)C=C1C(CC1)CCN1CC1=CC=C(C(O)=O)O1.O1C(C(=O)O)=CC=C1CN1CCC(C=2C3=CC=CC=C3N(CC=3C=CC(F)=CC=3)C=2)CC1 UZLXEGUTODDCEO-UHFFFAOYSA-N 0.000 claims 1
- RMGIQZFPNOUUJC-UHFFFAOYSA-N C(CC)OCCN1C=C(C2=CC=CC=C12)C1CCN(CC1)CCOC1=C(C(=O)O)C=CC=C1.C(C#C)OCCN1C=C(C2=CC=CC=C12)C1CCN(CC1)CCOC1=C(C(=O)O)C=CC=C1 Chemical compound C(CC)OCCN1C=C(C2=CC=CC=C12)C1CCN(CC1)CCOC1=C(C(=O)O)C=CC=C1.C(C#C)OCCN1C=C(C2=CC=CC=C12)C1CCN(CC1)CCOC1=C(C(=O)O)C=CC=C1 RMGIQZFPNOUUJC-UHFFFAOYSA-N 0.000 claims 1
- RISXHQOWLNWCBC-UHFFFAOYSA-N C(CCCC)N1C=C(C2=CC=CC=C12)C1CCN(CC1)CC=1C=C(C(=O)O)C=CC1.C1(CC1)CN1C=C(C2=CC=CC=C12)C1CCN(CC1)CCOC=1C=C(C=CC1)CC(=O)O Chemical compound C(CCCC)N1C=C(C2=CC=CC=C12)C1CCN(CC1)CC=1C=C(C(=O)O)C=CC1.C1(CC1)CN1C=C(C2=CC=CC=C12)C1CCN(CC1)CCOC=1C=C(C=CC1)CC(=O)O RISXHQOWLNWCBC-UHFFFAOYSA-N 0.000 claims 1
- QVIMNOYGANHNFY-UHFFFAOYSA-N C(CCCC)N1C=C(C2=CC=CC=C12)C1CCN(CC1)CCCC(=O)O.FC1=CC=C(CN2C=C(C3=CC=CC=C23)C2CCN(CC2)CCCC(=O)O)C=C1 Chemical compound C(CCCC)N1C=C(C2=CC=CC=C12)C1CCN(CC1)CCCC(=O)O.FC1=CC=C(CN2C=C(C3=CC=CC=C23)C2CCN(CC2)CCCC(=O)O)C=C1 QVIMNOYGANHNFY-UHFFFAOYSA-N 0.000 claims 1
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
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- 206010033557 Palpitations Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- 206010039897 Sedation Diseases 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
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- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
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- 210000004556 brain Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229940039748 oxalate Drugs 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
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- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Otolaryngology (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009901232A ES2165274B1 (es) | 1999-06-04 | 1999-06-04 | Nuevos derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
Publications (1)
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|---|---|
| ZA200109676B true ZA200109676B (en) | 2003-02-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200109676A ZA200109676B (en) | 1999-06-04 | 2001-11-23 | Indolylpiperidine derivatives as antihistaminic and anti-allergic agents. |
Country Status (35)
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| EP (1) | EP1183251B1 (https=) |
| JP (1) | JP2003501424A (https=) |
| KR (1) | KR100683454B1 (https=) |
| CN (1) | CN1191246C (https=) |
| AR (1) | AR029640A1 (https=) |
| AT (1) | ATE259362T1 (https=) |
| AU (1) | AU773164B2 (https=) |
| BG (1) | BG106168A (https=) |
| BR (1) | BR0011340A (https=) |
| CA (1) | CA2375985A1 (https=) |
| CO (1) | CO5180556A1 (https=) |
| CZ (1) | CZ20014334A3 (https=) |
| DE (1) | DE60008239T2 (https=) |
| DK (1) | DK1183251T3 (https=) |
| EE (1) | EE04717B1 (https=) |
| ES (2) | ES2165274B1 (https=) |
| HK (1) | HK1040990A1 (https=) |
| HU (1) | HUP0203320A3 (https=) |
| IL (1) | IL146629A0 (https=) |
| MX (1) | MXPA01012425A (https=) |
| MY (1) | MY127033A (https=) |
| NO (1) | NO20015897L (https=) |
| NZ (1) | NZ515649A (https=) |
| PE (1) | PE20010208A1 (https=) |
| PL (1) | PL196774B1 (https=) |
| PT (1) | PT1183251E (https=) |
| RU (1) | RU2246493C2 (https=) |
| SI (1) | SI1183251T1 (https=) |
| SK (1) | SK17042001A3 (https=) |
| TR (1) | TR200103490T2 (https=) |
| TW (1) | TWI226889B (https=) |
| UA (1) | UA72517C2 (https=) |
| WO (1) | WO2000075130A1 (https=) |
| ZA (1) | ZA200109676B (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
1999
- 1999-06-04 ES ES009901232A patent/ES2165274B1/es not_active Expired - Fee Related
-
2000
- 2000-05-31 AT AT00940296T patent/ATE259362T1/de not_active IP Right Cessation
- 2000-05-31 EE EEP200100653A patent/EE04717B1/xx not_active IP Right Cessation
- 2000-05-31 IL IL14662900A patent/IL146629A0/xx unknown
- 2000-05-31 MY MYPI20002439A patent/MY127033A/en unknown
- 2000-05-31 SI SI200030323T patent/SI1183251T1/xx unknown
- 2000-05-31 KR KR1020017015570A patent/KR100683454B1/ko not_active Expired - Fee Related
- 2000-05-31 ES ES00940296T patent/ES2211559T3/es not_active Expired - Lifetime
- 2000-05-31 WO PCT/EP2000/005010 patent/WO2000075130A1/en not_active Ceased
- 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
- 2000-05-31 SK SK1704-2001A patent/SK17042001A3/sk unknown
- 2000-05-31 MX MXPA01012425A patent/MXPA01012425A/es unknown
- 2000-05-31 UA UA2001118222A patent/UA72517C2/uk unknown
- 2000-05-31 JP JP2001502413A patent/JP2003501424A/ja not_active Ceased
- 2000-05-31 PL PL353164A patent/PL196774B1/pl not_active IP Right Cessation
- 2000-05-31 RU RU2002100073/04A patent/RU2246493C2/ru not_active IP Right Cessation
- 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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