JP2005526816A5 - - Google Patents
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- Publication number
- JP2005526816A5 JP2005526816A5 JP2003580332A JP2003580332A JP2005526816A5 JP 2005526816 A5 JP2005526816 A5 JP 2005526816A5 JP 2003580332 A JP2003580332 A JP 2003580332A JP 2003580332 A JP2003580332 A JP 2003580332A JP 2005526816 A5 JP2005526816 A5 JP 2005526816A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrrolo
- ylmethyl
- piperidin
- ethoxy
- 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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- 150000001875 compounds Chemical class 0.000 claims description 33
- -1 monoalkylamino Chemical group 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000004442 acylamino group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ACFYLYPXDPMTEE-UHFFFAOYSA-N 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OCCN2CCC(CC2)C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)=C1 ACFYLYPXDPMTEE-UHFFFAOYSA-N 0.000 claims description 2
- JLKYHWIEHOTYKV-UHFFFAOYSA-N 5-[[4-(1-butylpyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C12=CC=CN=C2N(CCCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(O)=O)=C1 JLKYHWIEHOTYKV-UHFFFAOYSA-N 0.000 claims description 2
- BMUYJOWZKQXKOE-UHFFFAOYSA-N 5-[[4-[1-[(5-chlorothiophen-2-yl)methyl]pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC=NC=C3N(CC=3SC(Cl)=CC=3)C=2)CC1 BMUYJOWZKQXKOE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000002015 acyclic group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- ZEJATSKNIRCBIA-UHFFFAOYSA-N ethyl 5-[[4-[1-[(5-chlorothiophen-2-yl)methyl]pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoate Chemical compound C1=C(OC)C(C(=O)OCC)=CC(CN2CCC(CC2)C=2C3=CC=NC=C3N(CC=3SC(Cl)=CC=3)C=2)=C1 ZEJATSKNIRCBIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 102000000543 Histamine Receptors Human genes 0.000 claims 3
- 108010002059 Histamine Receptors Proteins 0.000 claims 3
- 230000008485 antagonism Effects 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000005429 oxyalkyl group Chemical group 0.000 claims 3
- ZPSWGWBXSHLFNU-UHFFFAOYSA-N 2-[2-[4-[1-[(5-chlorothiophen-2-yl)methyl]pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC=3SC(Cl)=CC=3)C=2)CC1 ZPSWGWBXSHLFNU-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 2
- 206010012434 Dermatitis allergic Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 208000024780 Urticaria Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 201000010435 allergic urticaria Diseases 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- REAVZTXTGVGRRZ-UHFFFAOYSA-N ethyl 4-(1-butylpyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate Chemical compound C12=CC=CN=C2N(CCCC)C=C1C1CCN(C(=O)OCC)CC1 REAVZTXTGVGRRZ-UHFFFAOYSA-N 0.000 claims 2
- DCHSCSDZQAECIM-UHFFFAOYSA-N ethyl 4-(1-butylpyrrolo[2,3-c]pyridin-3-yl)piperidine-1-carboxylate Chemical compound C12=CC=NC=C2N(CCCC)C=C1C1CCN(C(=O)OCC)CC1 DCHSCSDZQAECIM-UHFFFAOYSA-N 0.000 claims 2
- CGURZCDMZJZAEK-UHFFFAOYSA-N ethyl 4-[1-(2-ethoxyethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxylate Chemical compound C12=CC=NC=C2N(CCOCC)C=C1C1CCN(C(=O)OCC)CC1 CGURZCDMZJZAEK-UHFFFAOYSA-N 0.000 claims 2
- OROXHPJZXQVNDH-UHFFFAOYSA-N ethyl 4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C(C1=CC=CN=C11)=CN1CC1=COC=C1 OROXHPJZXQVNDH-UHFFFAOYSA-N 0.000 claims 2
- JYBCUJJBMSMEJV-UHFFFAOYSA-N ethyl 4-[1-(furan-3-ylmethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C(C1=CC=NC=C11)=CN1CC1=COC=C1 JYBCUJJBMSMEJV-UHFFFAOYSA-N 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- RYYJEKLQXYGNCD-UHFFFAOYSA-N tert-butyl 4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C1=CC=CN=C11)=CN1CC1=COC=C1 RYYJEKLQXYGNCD-UHFFFAOYSA-N 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004001 thioalkyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- UOUCHRBTWUJIFR-UHFFFAOYSA-N 2,4-dimethoxy-3-[[4-[1-(2-methoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]benzoic acid Chemical compound C12=CC=CN=C2N(CCOC)C=C1C(CC1)CCN1CC1=C(OC)C=CC(C(O)=O)=C1OC UOUCHRBTWUJIFR-UHFFFAOYSA-N 0.000 claims 1
- PLBZUUUHIHCRBU-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]ethoxy]-3-methoxybenzoic acid Chemical compound C12=CC=CN=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=C(OC)C=CC=C1C(O)=O PLBZUUUHIHCRBU-UHFFFAOYSA-N 0.000 claims 1
- VGUDDLHJEJFLJO-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC=CN=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O VGUDDLHJEJFLJO-UHFFFAOYSA-N 0.000 claims 1
- YAMHSQLSSFOFQM-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]ethoxy]-6-methoxybenzoic acid Chemical compound C12=CC=CN=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC=CC(OC)=C1C(O)=O YAMHSQLSSFOFQM-UHFFFAOYSA-N 0.000 claims 1
- YBIXNUQZWKBEHO-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CN=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O YBIXNUQZWKBEHO-UHFFFAOYSA-N 0.000 claims 1
- FUQUVZMTNPRBJA-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-c]pyridin-3-yl)piperidin-1-yl]ethoxy]-3-methoxybenzoic acid Chemical compound C12=CC=NC=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=C(OC)C=CC=C1C(O)=O FUQUVZMTNPRBJA-UHFFFAOYSA-N 0.000 claims 1
- GIRKPSLBNJYIFD-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-c]pyridin-3-yl)piperidin-1-yl]ethoxy]-4-chlorobenzoic acid Chemical compound C12=CC=NC=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC(Cl)=CC=C1C(O)=O GIRKPSLBNJYIFD-UHFFFAOYSA-N 0.000 claims 1
- QTCXRHSDHFQNAN-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-c]pyridin-3-yl)piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC=NC=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O QTCXRHSDHFQNAN-UHFFFAOYSA-N 0.000 claims 1
- KVZBYJJEIWTOJR-UHFFFAOYSA-N 2-[2-[4-(1-butylpyrrolo[2,3-c]pyridin-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=NC=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O KVZBYJJEIWTOJR-UHFFFAOYSA-N 0.000 claims 1
- APCAIJPRKLEXHA-UHFFFAOYSA-N 2-[2-[4-(1-propan-2-ylpyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CN=C2N(C(C)C)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O APCAIJPRKLEXHA-UHFFFAOYSA-N 0.000 claims 1
- FHIVBUZOMPSZLJ-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-3-methoxybenzoic acid Chemical compound C12=CC=CN=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=C(OC)C=CC=C1C(O)=O FHIVBUZOMPSZLJ-UHFFFAOYSA-N 0.000 claims 1
- GIBHKXNVHBMLQI-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC=CN=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O GIBHKXNVHBMLQI-UHFFFAOYSA-N 0.000 claims 1
- YQUYNCAMUDVXTO-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-6-methoxybenzoic acid Chemical compound C12=CC=CN=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC(OC)=C1C(O)=O YQUYNCAMUDVXTO-UHFFFAOYSA-N 0.000 claims 1
- SNGUQRZEUFQWHT-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CN=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O SNGUQRZEUFQWHT-UHFFFAOYSA-N 0.000 claims 1
- CUERHJXIOLWGMQ-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]-3-methoxybenzoic acid Chemical compound C12=CC=NC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=C(OC)C=CC=C1C(O)=O CUERHJXIOLWGMQ-UHFFFAOYSA-N 0.000 claims 1
- WFLVYJBACWIQNA-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound C12=CC=NC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(O)=O WFLVYJBACWIQNA-UHFFFAOYSA-N 0.000 claims 1
- WFAAFNCXCYKWBJ-UHFFFAOYSA-N 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=NC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O WFAAFNCXCYKWBJ-UHFFFAOYSA-N 0.000 claims 1
- BUUXHSMNLYXNAC-UHFFFAOYSA-N 2-[2-[4-[1-(2-methoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=CN=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O BUUXHSMNLYXNAC-UHFFFAOYSA-N 0.000 claims 1
- XGXRBEJYAVAVRH-UHFFFAOYSA-N 2-[2-[4-[1-(2-methoxyethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound C12=CC=NC=C2N(CCOC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(O)=O XGXRBEJYAVAVRH-UHFFFAOYSA-N 0.000 claims 1
- PYOLLCHDGHDHPE-UHFFFAOYSA-N 2-[2-[4-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC3CC3)C=2)CC1 PYOLLCHDGHDHPE-UHFFFAOYSA-N 0.000 claims 1
- USXYPDDJWRXISA-UHFFFAOYSA-N 2-[2-[4-[1-(furan-2-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC=3OC=CC=3)C=2)CC1 USXYPDDJWRXISA-UHFFFAOYSA-N 0.000 claims 1
- JLBWRGCWXKZRJW-UHFFFAOYSA-N 2-[2-[4-[1-(furan-2-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OCCN2CCC(CC2)C=2C3=CC=CN=C3N(CC=3OC=CC=3)C=2)=C1 JLBWRGCWXKZRJW-UHFFFAOYSA-N 0.000 claims 1
- TWYLFUNGJMMWTL-UHFFFAOYSA-N 2-[2-[4-[1-(furan-2-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC=3OC=CC=3)C=2)CC1 TWYLFUNGJMMWTL-UHFFFAOYSA-N 0.000 claims 1
- RJJPSTWRBLUFKC-UHFFFAOYSA-N 2-[2-[4-[1-(furan-2-ylmethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=NC=C3N(CC=3OC=CC=3)C=2)CC1 RJJPSTWRBLUFKC-UHFFFAOYSA-N 0.000 claims 1
- FUJWSWJBDIAYII-UHFFFAOYSA-N 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)CC1 FUJWSWJBDIAYII-UHFFFAOYSA-N 0.000 claims 1
- JOJUCYRLKAWJSW-UHFFFAOYSA-N 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-6-methoxybenzoic acid Chemical compound COC1=CC=CC(OCCN2CCC(CC2)C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)=C1C(O)=O JOJUCYRLKAWJSW-UHFFFAOYSA-N 0.000 claims 1
- QXSSAEPAJDFISP-UHFFFAOYSA-N 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)CC1 QXSSAEPAJDFISP-UHFFFAOYSA-N 0.000 claims 1
- HDQYSDCHSNUTGL-UHFFFAOYSA-N 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OCCN2CCC(CC2)C=2C3=CC=NC=C3N(CC3=COC=C3)C=2)=C1 HDQYSDCHSNUTGL-UHFFFAOYSA-N 0.000 claims 1
- ZBKYOTKMQSYKRY-UHFFFAOYSA-N 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=NC=C3N(CC3=COC=C3)C=2)CC1 ZBKYOTKMQSYKRY-UHFFFAOYSA-N 0.000 claims 1
- FOPXOLLBCGHVGR-UHFFFAOYSA-N 2-[2-[4-[1-(pyridin-2-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC=3N=CC=CC=3)C=2)CC1 FOPXOLLBCGHVGR-UHFFFAOYSA-N 0.000 claims 1
- AMELPBNZUXWNBN-UHFFFAOYSA-N 2-[2-[4-[1-(thiophen-2-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC=3SC=CC=3)C=2)CC1 AMELPBNZUXWNBN-UHFFFAOYSA-N 0.000 claims 1
- NHESMZIWTNJWKB-UHFFFAOYSA-N 2-[2-[4-[1-(thiophen-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC3=CSC=C3)C=2)CC1 NHESMZIWTNJWKB-UHFFFAOYSA-N 0.000 claims 1
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- GOKNZMQDUVZOIL-UHFFFAOYSA-N 5-[[4-[1-(cyclopropylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC=CN=C3N(CC3CC3)C=2)CC1 GOKNZMQDUVZOIL-UHFFFAOYSA-N 0.000 claims 1
- UMEKKMQTWYNMKE-UHFFFAOYSA-N 5-[[4-[1-(furan-2-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC=CN=C3N(CC=3OC=CC=3)C=2)CC1 UMEKKMQTWYNMKE-UHFFFAOYSA-N 0.000 claims 1
- UFGYGDZCCVNMJX-UHFFFAOYSA-N 5-[[4-[1-(furan-2-ylmethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC=NC=C3N(CC=3OC=CC=3)C=2)CC1 UFGYGDZCCVNMJX-UHFFFAOYSA-N 0.000 claims 1
- NZXNSHJALAITOR-UHFFFAOYSA-N 5-[[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)CC1 NZXNSHJALAITOR-UHFFFAOYSA-N 0.000 claims 1
- PJZCLLWRUOXVPI-UHFFFAOYSA-N 5-[[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC=NC=C3N(CC3=COC=C3)C=2)CC1 PJZCLLWRUOXVPI-UHFFFAOYSA-N 0.000 claims 1
- AEZGRUYZBOYVHR-UHFFFAOYSA-N 5-[[4-[1-[(5-chlorothiophen-2-yl)methyl]pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(CN2CCC(CC2)C=2C3=CC=CN=C3N(CC=3SC(Cl)=CC=3)C=2)=C1 AEZGRUYZBOYVHR-UHFFFAOYSA-N 0.000 claims 1
- ZQIWWDOOQWHJPG-UHFFFAOYSA-N 5-[[4-[1-[(5-chlorothiophen-2-yl)methyl]pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1CN1CCC(C=2C3=CC=CN=C3N(CC=3SC(Cl)=CC=3)C=2)CC1 ZQIWWDOOQWHJPG-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical group [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 1
- 229940077388 benzenesulfonate Drugs 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- INCMYIZXGSTCCN-UHFFFAOYSA-N ethyl 3-[[4-[1-(2-methoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]benzoate Chemical compound CCOC(=O)C1=CC=CC(CN2CCC(CC2)C=2C3=CC=CN=C3N(CCOC)C=2)=C1 INCMYIZXGSTCCN-UHFFFAOYSA-N 0.000 claims 1
- FLZYNRMDLUOBDQ-UHFFFAOYSA-N ethyl 4-[1-[(5-chlorothiophen-2-yl)methyl]pyrrolo[2,3-c]pyridin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C(C1=CC=NC=C11)=CN1CC1=CC=C(Cl)S1 FLZYNRMDLUOBDQ-UHFFFAOYSA-N 0.000 claims 1
- MVPNMAJUKRHQBH-UHFFFAOYSA-N ethyl 5-[[4-(1-butylpyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]methyl]-2-methoxybenzoate Chemical compound C12=CC=CN=C2N(CCCC)C=C1C(CC1)CCN1CC1=CC=C(OC)C(C(=O)OCC)=C1 MVPNMAJUKRHQBH-UHFFFAOYSA-N 0.000 claims 1
- XOMLSCJDPYLFGG-UHFFFAOYSA-N ethyl 5-[[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]-2-methoxybenzoate Chemical compound C1=C(OC)C(C(=O)OCC)=CC(CN2CCC(CC2)C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)=C1 XOMLSCJDPYLFGG-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- KAIVTQDGZJDFBC-UHFFFAOYSA-N methyl 2-[2-[4-(1-butylpyrrolo[2,3-c]pyridin-3-yl)piperidin-1-yl]ethoxy]benzoate Chemical compound C12=CC=NC=C2N(CCCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(=O)OC KAIVTQDGZJDFBC-UHFFFAOYSA-N 0.000 claims 1
- YHWXJFHOUGAOFG-UHFFFAOYSA-N methyl 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoate Chemical compound C12=CC=CN=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC(OC)=CC=C1C(=O)OC YHWXJFHOUGAOFG-UHFFFAOYSA-N 0.000 claims 1
- ZGGHCYOBUSXZEM-UHFFFAOYSA-N methyl 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoate Chemical compound C12=CC=CN=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(=O)OC ZGGHCYOBUSXZEM-UHFFFAOYSA-N 0.000 claims 1
- SNXDSXYLTKYWOR-UHFFFAOYSA-N methyl 2-[2-[4-[1-(2-ethoxyethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoate Chemical compound C12=CC=NC=C2N(CCOCC)C=C1C(CC1)CCN1CCOC1=CC=CC=C1C(=O)OC SNXDSXYLTKYWOR-UHFFFAOYSA-N 0.000 claims 1
- WZUPJQUJRYKALY-UHFFFAOYSA-N methyl 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]ethoxy]benzoate Chemical compound COC(=O)C1=CC=CC=C1OCCN1CCC(C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)CC1 WZUPJQUJRYKALY-UHFFFAOYSA-N 0.000 claims 1
- YRYJVXWCAAIRMQ-UHFFFAOYSA-N methyl 2-[2-[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-c]pyridin-3-yl]piperidin-1-yl]ethoxy]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1OCCN1CCC(C=2C3=CC=NC=C3N(CC3=COC=C3)C=2)CC1 YRYJVXWCAAIRMQ-UHFFFAOYSA-N 0.000 claims 1
- WPYKNYCMQYQCMK-UHFFFAOYSA-N methyl 3-[[4-[1-(2-ethoxyethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]benzoate Chemical compound C12=CC=CN=C2N(CCOCC)C=C1C(CC1)CCN1CC1=CC=CC(C(=O)OC)=C1 WPYKNYCMQYQCMK-UHFFFAOYSA-N 0.000 claims 1
- FTINIVPXVUZWGL-UHFFFAOYSA-N methyl 3-[[4-[1-(furan-3-ylmethyl)pyrrolo[2,3-b]pyridin-3-yl]piperidin-1-yl]methyl]benzoate Chemical compound COC(=O)C1=CC=CC(CN2CCC(CC2)C=2C3=CC=CN=C3N(CC3=COC=C3)C=2)=C1 FTINIVPXVUZWGL-UHFFFAOYSA-N 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 239000012048 reactive intermediate Substances 0.000 claims 1
- PNEIBIZNGDLQFF-UHFFFAOYSA-N tert-butyl 4-[1-[(5-chlorothiophen-2-yl)methyl]pyrrolo[2,3-b]pyridin-3-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C(C1=CC=CN=C11)=CN1CC1=CC=C(Cl)S1 PNEIBIZNGDLQFF-UHFFFAOYSA-N 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- CVYSHYLNDIHEIM-UHFFFAOYSA-N ethyl 4-(1h-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OCC)CCC(C=2C3=CC=CN=C3NC=2)=C1 CVYSHYLNDIHEIM-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 4
- OPVBOUWKBVKFDB-UHFFFAOYSA-N ethyl 4-(1h-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1C1=CNC2=NC=CC=C12 OPVBOUWKBVKFDB-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 2
- LUBGFMZTGFXIIN-UHFFFAOYSA-N ethyl 4-oxopiperidine-1-carboxylate Chemical compound CCOC(=O)N1CCC(=O)CC1 LUBGFMZTGFXIIN-UHFFFAOYSA-N 0.000 description 2
- RSRCENWRTZQQQO-UHFFFAOYSA-N 1-[(5-chlorothiophen-2-yl)methyl]-3-piperidin-4-ylpyrrolo[2,3-c]pyridine Chemical compound S1C(Cl)=CC=C1CN1C2=CN=CC=C2C(C2CCNCC2)=C1 RSRCENWRTZQQQO-UHFFFAOYSA-N 0.000 description 1
- 0 C*(C)C(C)(CC(CC1)C2=C(*)N(*)/C3=*/*=B/*C/C=C23)CN1I Chemical compound C*(C)C(C)(CC(CC1)C2=C(*)N(*)/C3=*/*=B/*C/C=C23)CN1I 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BUPHWDPLYUEXFS-UHFFFAOYSA-N ethyl 5-(bromomethyl)-2-methoxybenzoate Chemical compound CCOC(=O)C1=CC(CBr)=CC=C1OC BUPHWDPLYUEXFS-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200200753A ES2201899B1 (es) | 2002-04-01 | 2002-04-01 | Derivados de la azaindolilpiperidina como agentes antihistaminicos y antialergicos. |
| PCT/EP2003/003377 WO2003082867A1 (en) | 2002-04-01 | 2003-04-01 | Azaindolylpiperidine derivatives as antihistaminic and antiallergic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005526816A JP2005526816A (ja) | 2005-09-08 |
| JP2005526816A5 true JP2005526816A5 (https=) | 2006-04-27 |
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Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7622480B2 (https=) |
| EP (1) | EP1497292B1 (https=) |
| JP (1) | JP2005526816A (https=) |
| AT (1) | ATE329916T1 (https=) |
| AU (1) | AU2003226765A1 (https=) |
| DE (1) | DE60306138T2 (https=) |
| DK (1) | DK1497292T3 (https=) |
| ES (2) | ES2201899B1 (https=) |
| PT (1) | PT1497292E (https=) |
| WO (1) | WO2003082867A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2005049559A2 (en) * | 2003-11-17 | 2005-06-02 | Boehringer Ingelheim International Gmbh | Novel piperidine-substituted indoles- or hetero-derivatives thereof and their use as modulators of chemokine receptor (ccr-3) |
| JP5049267B2 (ja) * | 2005-04-26 | 2012-10-17 | ハイプニオン・インコーポレイテッド | ベンズイソオキサゾールピペラジン化合物およびその使用方法 |
| JP5080450B2 (ja) * | 2005-04-30 | 2012-11-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規なピペリジン置換インドール |
| AU2006306497A1 (en) * | 2005-10-24 | 2007-05-03 | Janssen Pharmaceutica, N.V. | 3-piperidin-4-yl-indole ORL-1 receptor modulators |
| EP2079731B1 (en) * | 2006-10-27 | 2011-09-14 | Boehringer Ingelheim International GmbH | Novel substituted piperidyl-propane-thiols |
| WO2008049874A1 (en) * | 2006-10-27 | 2008-05-02 | Boehringer Ingelheim International Gmbh | Piperidyl-propane-thiol ccr3 modulators |
| EP2714688B1 (en) * | 2011-05-26 | 2016-02-24 | Daiichi Sankyo Company, Limited | Heterocyclic compounds as protein kinase inhibitors |
| MA40759A (fr) | 2014-09-26 | 2017-08-01 | Pfizer | Modulateurs de rorc2 de type pyrrolopyridine substitué par un méthyle et trifluorométhyle et leurs procédés d'utilisation |
| CA2969974C (en) | 2014-12-15 | 2020-08-04 | The Regents Of The University Of Michigan | Small molecule inhibitors of egfr and pi3k |
| KR101660863B1 (ko) * | 2015-04-03 | 2016-09-28 | 주식회사 녹십자 | IKKε 및 TBK1 억제제로서의 7-아자인돌 또는 4,7-다이아자인돌 유도체 및 이를 포함하는 약학적 조성물 |
| WO2022140456A1 (en) | 2020-12-22 | 2022-06-30 | Mekanistic Therapeutics Llc | Substituted aminobenzyl heteroaryl compounds as egfr and/or pi3k inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0536419B1 (en) * | 1991-04-23 | 1999-10-13 | Toray Industries, Inc. | Tricyclic triazole derivatives, production and use thereof |
| AU3176297A (en) * | 1996-06-25 | 1998-01-14 | Novartis Ag | Substituted 7-amino-pyrrolo{3,2-d}pyrimidines and the use thereof |
| ZA979961B (en) * | 1996-11-15 | 1999-05-05 | Lilly Co Eli | 5-HT1F agonists |
| ES2165274B1 (es) * | 1999-06-04 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| DK1309592T3 (da) | 2000-08-14 | 2006-08-21 | Ortho Mcneil Pharm Inc | Substituerede pyrazoler |
| NZ524682A (en) * | 2000-09-06 | 2004-11-26 | Ortho Mcneil Pharm Inc | A method for treating allergies using substituted pyrazoles |
| ES2172436B1 (es) | 2000-10-31 | 2004-01-16 | Almirall Prodesfarma Sa | Derivados de indolilpiperidina como agentes antihistaminicos y antialergicos. |
| MXPA03005432A (es) | 2000-12-22 | 2003-09-10 | Wyeth Corp | Compuestos de heterociclilindazol y -azaindazol como ligandos de 5-hidroxitriptamina-6. |
| WO2002079151A1 (en) | 2001-03-29 | 2002-10-10 | Smithkline Beecham P.L.C. | 3-substituted indoels or fused pyrroles as antagonists of the chemokine mcp-1 (ccr2b) receptor |
-
2002
- 2002-04-01 ES ES200200753A patent/ES2201899B1/es not_active Expired - Fee Related
-
2003
- 2003-04-01 PT PT03745302T patent/PT1497292E/pt unknown
- 2003-04-01 ES ES03745302T patent/ES2265577T3/es not_active Expired - Lifetime
- 2003-04-01 JP JP2003580332A patent/JP2005526816A/ja not_active Ceased
- 2003-04-01 EP EP03745302A patent/EP1497292B1/en not_active Expired - Lifetime
- 2003-04-01 AU AU2003226765A patent/AU2003226765A1/en not_active Abandoned
- 2003-04-01 DK DK03745302T patent/DK1497292T3/da active
- 2003-04-01 DE DE60306138T patent/DE60306138T2/de not_active Expired - Lifetime
- 2003-04-01 US US10/509,279 patent/US7622480B2/en not_active Expired - Fee Related
- 2003-04-01 WO PCT/EP2003/003377 patent/WO2003082867A1/en not_active Ceased
- 2003-04-01 AT AT03745302T patent/ATE329916T1/de not_active IP Right Cessation
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