JP2005528361A5 - - Google Patents
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- Publication number
- JP2005528361A5 JP2005528361A5 JP2003577882A JP2003577882A JP2005528361A5 JP 2005528361 A5 JP2005528361 A5 JP 2005528361A5 JP 2003577882 A JP2003577882 A JP 2003577882A JP 2003577882 A JP2003577882 A JP 2003577882A JP 2005528361 A5 JP2005528361 A5 JP 2005528361A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidin
- butyl
- pyridin
- alkyl
- diphenylmethyl
- 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.)
- Granted
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- -1 1-propenylene, 1-butenylene, 2-butenylene Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 201000010099 disease Diseases 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 206010020718 hyperplasia Diseases 0.000 claims 6
- 208000002780 macular degeneration Diseases 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000001246 bromo group Chemical group Br* 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 208000017442 Retinal disease Diseases 0.000 claims 3
- 206010038923 Retinopathy Diseases 0.000 claims 3
- 206010038934 Retinopathy proliferative Diseases 0.000 claims 3
- 208000027418 Wounds and injury Diseases 0.000 claims 3
- 206010064930 age-related macular degeneration Diseases 0.000 claims 3
- 230000006378 damage Effects 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 208000014674 injury Diseases 0.000 claims 3
- 230000001613 neoplastic effect Effects 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 238000003745 diagnosis Methods 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 201000007914 proliferative diabetic retinopathy Diseases 0.000 claims 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- KPBNHDGDUADAGP-UHFFFAOYSA-N N-[4-(1-benzoyl-4-piperidinyl)butyl]-3-(3-pyridinyl)-2-propenamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1)CCN1C(=O)C1=CC=CC=C1 KPBNHDGDUADAGP-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 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
- 239000000470 constituent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 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 1
- 238000000338 in vitro Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- ZFFDSAVEVVISAQ-UHFFFAOYSA-N n-[2-(1-benzhydrylpiperidin-4-yl)ethyl]-5-pyridin-3-ylpenta-2,4-dienamide Chemical compound C=1C=CN=CC=1C=CC=CC(=O)NCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ZFFDSAVEVVISAQ-UHFFFAOYSA-N 0.000 claims 1
- QMGOUVLXSSUFFY-UHFFFAOYSA-N n-[2-(1-benzhydrylpiperidin-4-yl)ethyl]-5-pyridin-3-ylpentanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCNC(=O)CCCCC1=CC=CN=C1 QMGOUVLXSSUFFY-UHFFFAOYSA-N 0.000 claims 1
- JWTZXMSOHSUKSN-UHFFFAOYSA-N n-[2-(1-benzoylpiperidin-4-yl)ethyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCC(CC1)CCN1C(=O)C1=CC=CC=C1 JWTZXMSOHSUKSN-UHFFFAOYSA-N 0.000 claims 1
- NFOBNJVVUWROAR-UHFFFAOYSA-N n-[3-(1-benzoylpiperidin-4-yl)propyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCC1CCCNC(=O)CCC1=CC=CN=C1 NFOBNJVVUWROAR-UHFFFAOYSA-N 0.000 claims 1
- RIYGFDAGQVEUIR-UHFFFAOYSA-N n-[4-(1-acetylpiperidin-4-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C1CN(C(=O)C)CCC1CCCCNC(=O)C=CC1=CC=CN=C1 RIYGFDAGQVEUIR-UHFFFAOYSA-N 0.000 claims 1
- RYJCJRWFCNMLEK-UHFFFAOYSA-N n-[4-(1-acetylpiperidin-4-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(=O)C)CCC1CCCCNC(=O)CCC1=CC=CN=C1 RYJCJRWFCNMLEK-UHFFFAOYSA-N 0.000 claims 1
- UEDCOZIIIZHTBF-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-2,2-difluoro-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCNC(=O)C(F)(F)CC1=CC=CN=C1 UEDCOZIIIZHTBF-UHFFFAOYSA-N 0.000 claims 1
- RNPODAPCSOZJFN-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-2-fluoro-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCNC(=O)C(F)CC1=CC=CN=C1 RNPODAPCSOZJFN-UHFFFAOYSA-N 0.000 claims 1
- BWKQOBUKMSAJFJ-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-3-(2-fluoropyridin-3-yl)propanamide Chemical compound FC1=NC=CC=C1CCC(=O)NCCCCC1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 BWKQOBUKMSAJFJ-UHFFFAOYSA-N 0.000 claims 1
- PONFDXRJIHDZOO-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-3-(5-fluoropyridin-3-yl)propanamide Chemical compound FC1=CN=CC(CCC(=O)NCCCCC2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 PONFDXRJIHDZOO-UHFFFAOYSA-N 0.000 claims 1
- VZGLEQAAAJNIAH-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCNC(=O)CCC1=CC=CN=C1 VZGLEQAAAJNIAH-UHFFFAOYSA-N 0.000 claims 1
- ABNUGIPWBGEPAS-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-5-pyridin-3-ylpenta-2,4-dienamide Chemical compound C=1C=CN=CC=1C=CC=CC(=O)NCCCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 ABNUGIPWBGEPAS-UHFFFAOYSA-N 0.000 claims 1
- YFGVUBJQEGVJPM-UHFFFAOYSA-N n-[4-(1-benzhydrylpiperidin-4-yl)butyl]-5-pyridin-3-ylpentanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCNC(=O)CCCCC1=CC=CN=C1 YFGVUBJQEGVJPM-UHFFFAOYSA-N 0.000 claims 1
- NHJNQCIMIFKBCK-UHFFFAOYSA-N n-[4-(1-benzoyl-2,6-dioxopiperidin-4-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1=O)CC(=O)N1C(=O)C1=CC=CC=C1 NHJNQCIMIFKBCK-UHFFFAOYSA-N 0.000 claims 1
- UKQGSFUTDYQJST-UHFFFAOYSA-N n-[4-(1-benzoylpiperidin-4-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCC1CCCCNC(=O)CCC1=CC=CN=C1 UKQGSFUTDYQJST-UHFFFAOYSA-N 0.000 claims 1
- BMAOVQOVHZRCHM-UHFFFAOYSA-N n-[4-(1-benzoylpiperidin-4-yl)butyl]-5-pyridin-3-ylpenta-2,4-dienamide Chemical compound C=1C=CN=CC=1C=CC=CC(=O)NCCCCC(CC1)CCN1C(=O)C1=CC=CC=C1 BMAOVQOVHZRCHM-UHFFFAOYSA-N 0.000 claims 1
- DBOZGEOLRIWRBI-UHFFFAOYSA-N n-[4-(1-benzylpiperidin-4-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(CC=2C=CC=CC=2)CCC1CCCCNC(=O)CCC1=CC=CN=C1 DBOZGEOLRIWRBI-UHFFFAOYSA-N 0.000 claims 1
- MUBDYBMESZNOAP-UHFFFAOYSA-N n-[4-(2,6-dioxo-3-phenylpiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(C1=O)C(=O)CCC1C1=CC=CC=C1 MUBDYBMESZNOAP-UHFFFAOYSA-N 0.000 claims 1
- ICEPIXBJALVIJL-UHFFFAOYSA-N n-[4-(2,6-dioxo-4-phenylpiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(C(C1)=O)C(=O)CC1C1=CC=CC=C1 ICEPIXBJALVIJL-UHFFFAOYSA-N 0.000 claims 1
- LYRLTNWCNOCAJL-UHFFFAOYSA-N n-[4-(4,4-diphenylpiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 LYRLTNWCNOCAJL-UHFFFAOYSA-N 0.000 claims 1
- SZHHBVITRIOFFX-UHFFFAOYSA-N n-[4-(4-benzhydrylpiperazin-1-yl)butyl]-2-pyridin-3-ylpropanamide Chemical compound C=1C=CN=CC=1C(C)C(=O)NCCCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 SZHHBVITRIOFFX-UHFFFAOYSA-N 0.000 claims 1
- JFHVQGJIXVSWFD-UHFFFAOYSA-N n-[4-(4-benzhydrylpiperazin-1-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CCCCNC(=O)CCC1=CC=CN=C1 JFHVQGJIXVSWFD-UHFFFAOYSA-N 0.000 claims 1
- PUSSBYQCSZCMTI-UHFFFAOYSA-N n-[4-(4-benzoylpiperazin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCN1C(=O)C1=CC=CC=C1 PUSSBYQCSZCMTI-UHFFFAOYSA-N 0.000 claims 1
- BBFHHQNKVPXFBN-UHFFFAOYSA-N n-[4-(4-benzoylpiperazin-1-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCN1CCCCNC(=O)CCC1=CC=CN=C1 BBFHHQNKVPXFBN-UHFFFAOYSA-N 0.000 claims 1
- GUPTYDOOLOZVQS-UHFFFAOYSA-N n-[4-(4-benzoylpiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCC1C(=O)C1=CC=CC=C1 GUPTYDOOLOZVQS-UHFFFAOYSA-N 0.000 claims 1
- AEZGWSJOCITUGL-UHFFFAOYSA-N n-[4-(4-benzoylpiperidin-1-yl)butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CC(C(=O)C=2C=CC=CC=2)CCN1CCCCNC(=O)CCC1=CC=CN=C1 AEZGWSJOCITUGL-UHFFFAOYSA-N 0.000 claims 1
- WYJPOJTUEYSIBC-UHFFFAOYSA-N n-[4-(4-benzyl-2,6-dioxopiperazin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(C(C1)=O)C(=O)CN1CC1=CC=CC=C1 WYJPOJTUEYSIBC-UHFFFAOYSA-N 0.000 claims 1
- LPLXNYOOYXDJFK-UHFFFAOYSA-N n-[4-(4-phenylpiperidin-1-yl)butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCC1C1=CC=CC=C1 LPLXNYOOYXDJFK-UHFFFAOYSA-N 0.000 claims 1
- PQJHAVGHPXLTQD-UHFFFAOYSA-N n-[4-[1-(2,2-diphenylacetyl)piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1)CCN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 PQJHAVGHPXLTQD-UHFFFAOYSA-N 0.000 claims 1
- NNAUZAULZZIIQV-UHFFFAOYSA-N n-[4-[1-(2,2-diphenylacetyl)piperidin-4-yl]butyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCNC(=O)CCC1=CC=CN=C1 NNAUZAULZZIIQV-UHFFFAOYSA-N 0.000 claims 1
- GRTBFFDLPDANJH-UHFFFAOYSA-N n-[4-[1-(3,3-diphenylpropanoyl)piperidin-4-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCC(CC1)CCN1C(=O)CC(C=1C=CC=CC=1)C1=CC=CC=C1 GRTBFFDLPDANJH-UHFFFAOYSA-N 0.000 claims 1
- DFDWGAJVQZUYCS-UHFFFAOYSA-N n-[4-[4-(2,2-diphenylacetyl)piperazin-1-yl]butyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCN(CC1)CCN1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 DFDWGAJVQZUYCS-UHFFFAOYSA-N 0.000 claims 1
- DORZSCZPSGZOKB-UHFFFAOYSA-N n-[5-(1-benzhydrylpiperidin-4-yl)pentyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCCNC(=O)CCC1=CC=CN=C1 DORZSCZPSGZOKB-UHFFFAOYSA-N 0.000 claims 1
- RTOVZAWTXPBIEP-UHFFFAOYSA-N n-[5-(1-benzhydrylpiperidin-4-yl)pentyl]-5-pyridin-3-ylpenta-2,4-dienamide Chemical compound C=1C=CN=CC=1C=CC=CC(=O)NCCCCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 RTOVZAWTXPBIEP-UHFFFAOYSA-N 0.000 claims 1
- BWNGMTNRODBWPY-UHFFFAOYSA-N n-[5-(4-benzhydrylpiperazin-1-yl)pentyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 BWNGMTNRODBWPY-UHFFFAOYSA-N 0.000 claims 1
- KRFYUWHTBWCRHF-UHFFFAOYSA-N n-[6-(1-benzhydrylpiperidin-4-yl)hexyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1CCCCCCNC(=O)CCC1=CC=CN=C1 KRFYUWHTBWCRHF-UHFFFAOYSA-N 0.000 claims 1
- AVZNELZWYQWZGG-UHFFFAOYSA-N n-[6-(1-benzhydrylpiperidin-4-yl)hexyl]-5-pyridin-3-ylpenta-2,4-dienamide Chemical compound C=1C=CN=CC=1C=CC=CC(=O)NCCCCCCC(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 AVZNELZWYQWZGG-UHFFFAOYSA-N 0.000 claims 1
- YNVDXMVUUBLCDC-UHFFFAOYSA-N n-[6-(1-benzoylpiperidin-4-yl)hexyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCCCC(CC1)CCN1C(=O)C1=CC=CC=C1 YNVDXMVUUBLCDC-UHFFFAOYSA-N 0.000 claims 1
- YCCJHEXXHODDES-UHFFFAOYSA-N n-[6-(1-benzoylpiperidin-4-yl)hexyl]-3-pyridin-3-ylpropanamide Chemical compound C1CN(C(=O)C=2C=CC=CC=2)CCC1CCCCCCNC(=O)CCC1=CC=CN=C1 YCCJHEXXHODDES-UHFFFAOYSA-N 0.000 claims 1
- NOEFHKQJZGIEJM-UHFFFAOYSA-N n-[6-(4-benzhydrylpiperazin-1-yl)hexyl]-3-pyridin-3-ylprop-2-enamide Chemical compound C=1C=CN=CC=1C=CC(=O)NCCCCCCN(CC1)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NOEFHKQJZGIEJM-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000006711 vascular endothelial growth factor production Effects 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001772 anti-angiogenic effect Effects 0.000 description 2
- WFLOTYSKFUPZQB-OWOJBTEDSA-N (e)-1,2-difluoroethene Chemical compound F\C=C\F WFLOTYSKFUPZQB-OWOJBTEDSA-N 0.000 description 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
- 125000005569 butenylene group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02006697A EP1348434A1 (en) | 2002-03-27 | 2002-03-27 | Use of pyridyl amides as inhibitors of angiogenesis |
| PCT/EP2003/003060 WO2003080054A1 (en) | 2002-03-27 | 2003-03-24 | Use of pyridyl amides as inhibitors of angiogenesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005528361A JP2005528361A (ja) | 2005-09-22 |
| JP2005528361A5 true JP2005528361A5 (https=) | 2006-05-18 |
| JP4599062B2 JP4599062B2 (ja) | 2010-12-15 |
Family
ID=27798796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003577882A Expired - Fee Related JP4599062B2 (ja) | 2002-03-27 | 2003-03-24 | 脈管形成抑制剤としてのピリジルアミド |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20060052419A1 (https=) |
| EP (2) | EP1348434A1 (https=) |
| JP (1) | JP4599062B2 (https=) |
| AT (1) | ATE453393T1 (https=) |
| AU (1) | AU2003215672A1 (https=) |
| CY (1) | CY1109925T1 (https=) |
| DE (1) | DE60330757D1 (https=) |
| DK (1) | DK1487444T3 (https=) |
| ES (1) | ES2337780T3 (https=) |
| PT (1) | PT1487444E (https=) |
| SI (1) | SI1487444T1 (https=) |
| WO (1) | WO2003080054A1 (https=) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7977049B2 (en) | 2002-08-09 | 2011-07-12 | President And Fellows Of Harvard College | Methods and compositions for extending the life span and increasing the stress resistance of cells and organisms |
| MXPA06010543A (es) | 2004-03-15 | 2007-03-26 | Ptc Therapeutics Inc | Derivados de carbolina utiles en la inhibicion de la angiogenesis. |
| US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
| JP4855485B2 (ja) * | 2006-02-17 | 2012-01-18 | エフ．ホフマン−ラ ロシュ アーゲー | ５ｈｔ２／ｄ３モジュレーターとしてのベンゾイル−ピペリジン誘導体 |
| WO2008026018A1 (en) * | 2006-09-01 | 2008-03-06 | Topotarget Switzerland Sa | New method for the treatment of inflammatory diseases |
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| US4224326A (en) * | 1978-09-21 | 1980-09-23 | Eli Lilly And Company | Immunosuppressive agents |
| US4778796A (en) * | 1985-07-19 | 1988-10-18 | Dainippon Pharmaceutical Co., Ltd. | ω-(3-pyridyl)alkenamide derivatives and anti-allergenic pharmaceutical compositions containing same |
| DE19624659A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalken- und Pyridylalkinsäureamide |
| DE19624668A1 (de) * | 1996-06-20 | 1998-02-19 | Klinge Co Chem Pharm Fab | Verwendung von Pyridylalkan-, Pyridylalken- bzw. Pyridylalkinsäureamiden |
| DE19624704A1 (de) * | 1996-06-20 | 1998-01-08 | Klinge Co Chem Pharm Fab | Neue Pyridylalkansäureamide |
| WO1998002170A1 (en) * | 1996-07-17 | 1998-01-22 | The General Hospital Corporation | Method of inducing vasodilation and treating pulmonary hypertension using adenoviral-mediated transfer of the nitric oxide synthase gene |
| DE19756235A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperidinylsubstituierte Pyridylalkan- alken- und -alkincarbonsäureamide |
| DE19756236A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue piperazinylsubstituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
| DE19756212A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue, mit einem cyclischen Imid substituierte Pyridylalkan-, alken- und -alkincarbonsäureamide |
| DE19756261A1 (de) * | 1997-12-17 | 1999-07-01 | Klinge Co Chem Pharm Fab | Neue arylsubstituierte Pyridylalkan-, alken- und alkincarbonsäureamide |
| DE19818044A1 (de) * | 1998-04-22 | 1999-10-28 | Klinge Co Chem Pharm Fab | Verwendung von Vitamin-PP-Verbindungen |
-
2002
- 2002-03-27 EP EP02006697A patent/EP1348434A1/en not_active Withdrawn
-
2003
- 2003-03-24 DE DE60330757T patent/DE60330757D1/de not_active Expired - Lifetime
- 2003-03-24 WO PCT/EP2003/003060 patent/WO2003080054A1/en not_active Ceased
- 2003-03-24 AU AU2003215672A patent/AU2003215672A1/en not_active Abandoned
- 2003-03-24 SI SI200331755T patent/SI1487444T1/sl unknown
- 2003-03-24 ES ES03744849T patent/ES2337780T3/es not_active Expired - Lifetime
- 2003-03-24 JP JP2003577882A patent/JP4599062B2/ja not_active Expired - Fee Related
- 2003-03-24 EP EP03744849A patent/EP1487444B9/en not_active Expired - Lifetime
- 2003-03-24 US US10/509,362 patent/US20060052419A1/en not_active Abandoned
- 2003-03-24 DK DK03744849.5T patent/DK1487444T3/da active
- 2003-03-24 AT AT03744849T patent/ATE453393T1/de active
- 2003-03-24 PT PT03744849T patent/PT1487444E/pt unknown
-
2010
- 2010-03-22 CY CY20101100264T patent/CY1109925T1/el unknown
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