CN104363903A - 用作蛋白聚集抑制剂的苯基脲和苯基氨基甲酸盐/酯衍生物 - Google Patents
用作蛋白聚集抑制剂的苯基脲和苯基氨基甲酸盐/酯衍生物 Download PDFInfo
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- CN104363903A CN104363903A CN201380017441.6A CN201380017441A CN104363903A CN 104363903 A CN104363903 A CN 104363903A CN 201380017441 A CN201380017441 A CN 201380017441A CN 104363903 A CN104363903 A CN 104363903A
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- Prior art keywords
- ethyl
- indol
- urea
- compound
- methyl
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- 230000004845 protein aggregation Effects 0.000 title claims abstract description 17
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 title abstract description 10
- PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical class OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title description 5
- 238000000034 method Methods 0.000 claims abstract description 53
- 201000010099 disease Diseases 0.000 claims abstract description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 23
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 14
- 208000001089 Multiple system atrophy Diseases 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 104
- -1 hydroxyl Chemical group 0.000 claims description 70
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000004202 carbamide Substances 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- FKFSPCZNABVGFH-UHFFFAOYSA-N 1-[3-ethyl-4-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C=C(CC=2C3=CC=CC=C3NC=2)C(CC)=CC=1NC(=O)NCCN1CCN(C)CC1 FKFSPCZNABVGFH-UHFFFAOYSA-N 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 5
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- RBYNETHHEMQMNK-UHFFFAOYSA-N 1-(2-aminoethyl)-3-[3-ethyl-4-(1h-indol-3-ylmethyl)phenyl]urea Chemical compound CCC1=CC(NC(=O)NCCN)=CC=C1CC1=CNC2=CC=CC=C12 RBYNETHHEMQMNK-UHFFFAOYSA-N 0.000 claims description 4
- BUMROPPMYBHLLF-UHFFFAOYSA-N 1-[3-butyl-5-hydroxy-4-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(O)=C(CC=2C3=CC=CC=C3NC=2)C(CCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 BUMROPPMYBHLLF-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 4
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000005936 piperidyl group Chemical group 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims description 3
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 210000004558 lewy body Anatomy 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- HBDDRESWUAFAHY-UHFFFAOYSA-N thiomorpholin-3-one Chemical compound O=C1CSCCN1 HBDDRESWUAFAHY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 4
- CVGWWSWCDADCHQ-UHFFFAOYSA-N 1-[3-(1h-indol-3-ylmethyl)-5-methoxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OC)=CC(CC=2C3=CC=CC=C3NC=2)=CC=1NC(=O)NCCN1CCN(C)CC1 CVGWWSWCDADCHQ-UHFFFAOYSA-N 0.000 claims 1
- OEWMTCRSEPVHFY-UHFFFAOYSA-N 1-[3-[2-(1h-indol-3-yl)ethyl]-5-propan-2-ylphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]thiourea Chemical compound C=1C(C(C)C)=CC(CCC=2C3=CC=CC=C3NC=2)=CC=1NC(=S)NCCN1CCN(C)CC1 OEWMTCRSEPVHFY-UHFFFAOYSA-N 0.000 claims 1
- QVPSBZWFQYGAKC-UHFFFAOYSA-N 1-[3-butyl-4-(1h-indol-3-ylmethyl)-5-(trifluoromethoxy)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OC(F)(F)F)=C(CC=2C3=CC=CC=C3NC=2)C(CCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 QVPSBZWFQYGAKC-UHFFFAOYSA-N 0.000 claims 1
- GGBQZKQFGCFYRL-UHFFFAOYSA-N 1-[3-butyl-4-(1h-indol-3-ylmethyl)-5-methoxyphenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C=1C(OC)=C(CC=2C3=CC=CC=C3NC=2)C(CCCC)=CC=1NC(=O)NCCN1CCN(C)CC1 GGBQZKQFGCFYRL-UHFFFAOYSA-N 0.000 claims 1
- QAKMKLOSXMOKPU-UHFFFAOYSA-N 1-[3-butyl-5-(1h-indol-3-ylmethyl)phenyl]-3-(2-piperidin-4-ylethyl)urea Chemical compound C=1C(CCCC)=CC(CC=2C3=CC=CC=C3NC=2)=CC=1NC(=O)NCCC1CCNCC1 QAKMKLOSXMOKPU-UHFFFAOYSA-N 0.000 claims 1
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- RDXTURUZNDFRCO-UHFFFAOYSA-N 1-[3-cyclopentyloxy-5-(1h-indol-3-ylmethyl)phenyl]-3-[2-(4-methylpiperazin-1-yl)ethyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1=CC(CC=2C3=CC=CC=C3NC=2)=CC(OC2CCCC2)=C1 RDXTURUZNDFRCO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
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- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
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- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/14—Radicals substituted by nitrogen atoms
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- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| US201261616771P | 2012-03-28 | 2012-03-28 | |
| US61/616,771 | 2012-03-28 | ||
| PCT/US2013/032552 WO2013148365A1 (en) | 2012-03-28 | 2013-03-15 | Phenyl-urea and phenyl-carbamate derivatives as inhibitors of protein aggregation |
Publications (1)
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| CN104363903A true CN104363903A (zh) | 2015-02-18 |
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS57533B1 (sr) | 2014-01-29 | 2018-10-31 | Ucb Biopharma Sprl | Heteroaril amidi kao inhibitori proteinske agregacije |
| WO2016040780A1 (en) * | 2014-09-11 | 2016-03-17 | Neuropore Therapies, Inc. | Aminomethyl- and methyloxy-linked tricyclic compounds as inhibitors of protein aggregation |
| WO2017020010A1 (en) | 2015-07-29 | 2017-02-02 | Neuropore Therapies, Inc. | Bis-heteroaryl derivatives as modulators of protein aggregation |
| BR112019011932A2 (pt) | 2017-01-26 | 2019-10-29 | Ucb Biopharma Sprl | derivados de bis-heteroarila como moduladores da agregação de proteína |
| ES2884145T3 (es) | 2017-01-26 | 2021-12-10 | UCB Biopharma SRL | Derivados bicíclicos de bis-heteroarilo como moduladores de la agregación de proteínas |
| JP7100042B2 (ja) | 2017-01-26 | 2022-07-12 | ユーシービー バイオファルマ エスアールエル | タンパク質凝集のモジュレーターとしてのアルコキシビス－ヘテロアリール誘導体 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030125354A1 (en) * | 1999-11-16 | 2003-07-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds use as anti-inflammatory agents |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| US20040097499A1 (en) * | 1998-07-31 | 2004-05-20 | Arnold Macklin Brian | Amide, carbamate, and urea derivatives |
| WO2011084642A1 (en) * | 2009-12-16 | 2011-07-14 | Neuropore Therapies, Inc. | Compound suitable for the treatment of synucleopathies |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE59712297D1 (de) * | 1996-01-26 | 2005-06-09 | Altana Pharma Ag | 3-alkylimidazopyridine |
| GB2384776C (en) * | 2000-10-30 | 2006-02-03 | Kudos Pharm Ltd | Phthalazinone derivatives |
| JP2006520333A (ja) * | 2003-03-14 | 2006-09-07 | ハー・ルンドベック・アクチエゼルスカベット | 置換されたアニリン誘導体 |
| MXPA05010000A (es) * | 2003-03-21 | 2005-11-17 | Lundbeck & Co As H | Derivados de p-diaminobenceno substituidos. |
| EP1684762A4 (en) * | 2003-11-13 | 2009-06-17 | Ambit Biosciences Corp | UREA DERIVATIVES AS MODULATORS OF KINASE |
| PL1893612T3 (pl) | 2005-06-22 | 2012-01-31 | Plexxikon Inc | Pochodne pirolo-[2,3-b]pirydyny jako inhibitory kinazy białkowej |
| WO2007124423A2 (en) | 2006-04-21 | 2007-11-01 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO2008044688A1 (en) * | 2006-10-11 | 2008-04-17 | Daiichi Sankyo Company, Limited | Urea derivative |
| WO2010036316A1 (en) | 2008-09-24 | 2010-04-01 | Yangbo Feng | Urea and carbamate compounds and analogs as kinase inhibitors |
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2013
- 2013-03-15 NZ NZ631388A patent/NZ631388A/en not_active IP Right Cessation
- 2013-03-15 ES ES13768915T patent/ES2768602T3/es active Active
- 2013-03-15 RU RU2014143242A patent/RU2014143242A/ru not_active Application Discontinuation
- 2013-03-15 CN CN201380017441.6A patent/CN104363903A/zh active Pending
- 2013-03-15 EP EP13768915.4A patent/EP2830608B8/en active Active
- 2013-03-15 KR KR1020147030291A patent/KR20150002713A/ko not_active Withdrawn
- 2013-03-15 WO PCT/US2013/032552 patent/WO2013148365A1/en not_active Ceased
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- 2014-09-23 IL IL234825A patent/IL234825A0/en unknown
- 2014-10-15 IN IN8633DEN2014 patent/IN2014DN08633A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040097499A1 (en) * | 1998-07-31 | 2004-05-20 | Arnold Macklin Brian | Amide, carbamate, and urea derivatives |
| US20030125354A1 (en) * | 1999-11-16 | 2003-07-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds use as anti-inflammatory agents |
| EP1402888A1 (en) * | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| WO2011084642A1 (en) * | 2009-12-16 | 2011-07-14 | Neuropore Therapies, Inc. | Compound suitable for the treatment of synucleopathies |
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| US20150166543A1 (en) | 2015-06-18 |
| KR20150002713A (ko) | 2015-01-07 |
| JP6159388B2 (ja) | 2017-07-05 |
| EP2830608B1 (en) | 2019-12-11 |
| ES2768602T3 (es) | 2020-06-23 |
| US9527852B2 (en) | 2016-12-27 |
| HK1202452A1 (en) | 2015-10-02 |
| IL234825A0 (en) | 2014-12-31 |
| IN2014DN08633A (enExample) | 2015-05-22 |
| NZ631388A (en) | 2016-01-29 |
| JP2015515465A (ja) | 2015-05-28 |
| EP2830608B8 (en) | 2020-01-15 |
| CA2867175A1 (en) | 2013-10-03 |
| EP2830608A1 (en) | 2015-02-04 |
| AU2013240219A1 (en) | 2014-10-09 |
| WO2013148365A1 (en) | 2013-10-03 |
| RU2014143242A (ru) | 2016-05-20 |
| MX2014011615A (es) | 2015-01-19 |
| EP2830608A4 (en) | 2015-08-19 |
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