JP2014526526A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014526526A5 JP2014526526A5 JP2014531124A JP2014531124A JP2014526526A5 JP 2014526526 A5 JP2014526526 A5 JP 2014526526A5 JP 2014531124 A JP2014531124 A JP 2014531124A JP 2014531124 A JP2014531124 A JP 2014531124A JP 2014526526 A5 JP2014526526 A5 JP 2014526526A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidin
- benzyl
- methyl
- sub
- expression
- 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
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- DKXVMUSAJPOKQF-JOCHJYFZSA-N 2-[(2r)-1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-5-fluoro-1h-indole Chemical compound C1=C(C)C(C)=CC=C1CN1[C@@H](C=2NC3=CC=C(F)C=C3C=2)CCCC1 DKXVMUSAJPOKQF-JOCHJYFZSA-N 0.000 claims 1
- OLRMYAAPFOHNRD-HXUWFJFHSA-N 2-[(2r)-1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-6-fluoro-1h-benzimidazole Chemical compound C1=C(C)C(C)=CC=C1CN1[C@@H](C=2NC3=CC(F)=CC=C3N=2)CCCC1 OLRMYAAPFOHNRD-HXUWFJFHSA-N 0.000 claims 1
- NBJDKJUIPOILKD-HXUWFJFHSA-N 2-[(2r)-1-[(4-fluorophenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound C1=CC(F)=CC=C1CN1[C@@H](C=2NC3=CC=CC=C3C=2)CCCC1 NBJDKJUIPOILKD-HXUWFJFHSA-N 0.000 claims 1
- LZCSBLQJPVGFBZ-UHFFFAOYSA-N 2-[1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-1h-imidazo[4,5-b]pyrazine Chemical compound C1=C(C)C(C)=CC=C1CN1C(C=2NC3=NC=CN=C3N=2)CCCC1 LZCSBLQJPVGFBZ-UHFFFAOYSA-N 0.000 claims 1
- TWMPWEBCEQSZAX-UHFFFAOYSA-N 2-[1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-3h-benzimidazole-5-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1CN1C(C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)CCCC1 TWMPWEBCEQSZAX-UHFFFAOYSA-N 0.000 claims 1
- OLRMYAAPFOHNRD-UHFFFAOYSA-N 2-[1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-6-fluoro-1h-benzimidazole Chemical compound C1=C(C)C(C)=CC=C1CN1C(C=2NC3=CC(F)=CC=C3N=2)CCCC1 OLRMYAAPFOHNRD-UHFFFAOYSA-N 0.000 claims 1
- GZWZQOYGKXFONA-UHFFFAOYSA-N 2-[1-[(3-methylphenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound CC1=CC=CC(CN2C(CCCC2)C=2NC3=CC=CC=C3C=2)=C1 GZWZQOYGKXFONA-UHFFFAOYSA-N 0.000 claims 1
- FQWCWYFLZZZXKW-UHFFFAOYSA-N 2-[1-[(3-methylphenyl)methyl]piperidin-2-yl]-3h-benzimidazole-5-sulfonamide Chemical compound CC1=CC=CC(CN2C(CCCC2)C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)=C1 FQWCWYFLZZZXKW-UHFFFAOYSA-N 0.000 claims 1
- NBJDKJUIPOILKD-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound C1=CC(F)=CC=C1CN1C(C=2NC3=CC=CC=C3C=2)CCCC1 NBJDKJUIPOILKD-UHFFFAOYSA-N 0.000 claims 1
- QFOCLRLROCNMLK-UHFFFAOYSA-N 2-ethyl-4-[[2-(5-fluoro-1h-indol-2-yl)piperidin-1-yl]methyl]-1,3-thiazole Chemical compound S1C(CC)=NC(CN2C(CCCC2)C=2NC3=CC=C(F)C=C3C=2)=C1 QFOCLRLROCNMLK-UHFFFAOYSA-N 0.000 claims 1
- YCVYVPOQQDXIPA-UHFFFAOYSA-N 2-ethyl-4-[[2-(6-fluoro-1h-benzimidazol-2-yl)piperidin-1-yl]methyl]-1,3-thiazole Chemical compound S1C(CC)=NC(CN2C(CCCC2)C=2NC3=CC(F)=CC=C3N=2)=C1 YCVYVPOQQDXIPA-UHFFFAOYSA-N 0.000 claims 1
- SCIAOYUFSDEZFK-UHFFFAOYSA-N 5-chloro-2-[1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-6-methyl-1h-benzimidazole Chemical compound C1=C(C)C(C)=CC=C1CN1C(C=2NC3=CC(C)=C(Cl)C=C3N=2)CCCC1 SCIAOYUFSDEZFK-UHFFFAOYSA-N 0.000 claims 1
- LDMIZGWIAFZNAZ-UHFFFAOYSA-N 5-chloro-2-[1-[(4-methoxyphenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound C1=CC(OC)=CC=C1CN1C(C=2NC3=CC=C(Cl)C=C3C=2)CCCC1 LDMIZGWIAFZNAZ-UHFFFAOYSA-N 0.000 claims 1
- IQMSPNHSPWELAK-UHFFFAOYSA-N 5-chloro-6-methyl-2-[1-[(3-methylphenyl)methyl]piperidin-2-yl]-1h-benzimidazole Chemical compound CC1=CC=CC(CN2C(CCCC2)C=2NC3=CC(C)=C(Cl)C=C3N=2)=C1 IQMSPNHSPWELAK-UHFFFAOYSA-N 0.000 claims 1
- FZXJCAJAGROONK-UHFFFAOYSA-N 5-chloro-6-methyl-2-[1-[[3-(trifluoromethyl)phenyl]methyl]piperidin-2-yl]-1h-benzimidazole Chemical compound N=1C=2C=C(Cl)C(C)=CC=2NC=1C1CCCCN1CC1=CC=CC(C(F)(F)F)=C1 FZXJCAJAGROONK-UHFFFAOYSA-N 0.000 claims 1
- XGMLIHFZNRVXAI-HXUWFJFHSA-N 5-fluoro-2-[(2r)-1-[(4-fluorophenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound C1=CC(F)=CC=C1CN1[C@@H](C=2NC3=CC=C(F)C=C3C=2)CCCC1 XGMLIHFZNRVXAI-HXUWFJFHSA-N 0.000 claims 1
- NRMDGJLVROYMCQ-UHFFFAOYSA-N 5-fluoro-2-[1-[(3-methoxyphenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound COC1=CC=CC(CN2C(CCCC2)C=2NC3=CC=C(F)C=C3C=2)=C1 NRMDGJLVROYMCQ-UHFFFAOYSA-N 0.000 claims 1
- OJOFGJOYTKTNNM-UHFFFAOYSA-N 5-fluoro-2-[1-[(4-fluorophenyl)methyl]-6-methylpiperidin-2-yl]-1h-indole Chemical compound CC1CCCC(C=2NC3=CC=C(F)C=C3C=2)N1CC1=CC=C(F)C=C1 OJOFGJOYTKTNNM-UHFFFAOYSA-N 0.000 claims 1
- XZQDCSDFFLUYMO-UHFFFAOYSA-N 5-fluoro-2-[1-[(4-methoxyphenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound C1=CC(OC)=CC=C1CN1C(C=2NC3=CC=C(F)C=C3C=2)CCCC1 XZQDCSDFFLUYMO-UHFFFAOYSA-N 0.000 claims 1
- NYACPLPGMSSHKQ-UHFFFAOYSA-N 5-fluoro-2-[1-[(4-methylphenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound C1=CC(C)=CC=C1CN1C(C=2NC3=CC=C(F)C=C3C=2)CCCC1 NYACPLPGMSSHKQ-UHFFFAOYSA-N 0.000 claims 1
- GQOMLCGNFQKYCS-UHFFFAOYSA-N 5-fluoro-2-[6-methyl-1-[(3-methylphenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound CC1CCCC(C=2NC3=CC=C(F)C=C3C=2)N1CC1=CC=CC(C)=C1 GQOMLCGNFQKYCS-UHFFFAOYSA-N 0.000 claims 1
- DRMAXGDSLXBBNB-UHFFFAOYSA-N 5-fluoro-2-[6-methyl-1-[(5-methylfuran-2-yl)methyl]piperidin-2-yl]-1h-indole Chemical compound CC1CCCC(C=2NC3=CC=C(F)C=C3C=2)N1CC1=CC=C(C)O1 DRMAXGDSLXBBNB-UHFFFAOYSA-N 0.000 claims 1
- FSVHLZXSAWCYRP-UHFFFAOYSA-N 5-methoxy-2-[1-[(3-methoxyphenyl)methyl]piperidin-2-yl]-1h-indole Chemical compound COC1=CC=CC(CN2C(CCCC2)C=2NC3=CC=C(OC)C=C3C=2)=C1 FSVHLZXSAWCYRP-UHFFFAOYSA-N 0.000 claims 1
- DWCJVIMWGAXCOY-UHFFFAOYSA-N 6-bromo-2-[1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-1h-benzimidazole Chemical compound C1=C(C)C(C)=CC=C1CN1C(C=2NC3=CC(Br)=CC=C3N=2)CCCC1 DWCJVIMWGAXCOY-UHFFFAOYSA-N 0.000 claims 1
- HBVCXUNMLJPSFB-UHFFFAOYSA-N 6-bromo-2-[1-[(3-methylphenyl)methyl]piperidin-2-yl]-1h-benzimidazole Chemical compound CC1=CC=CC(CN2C(CCCC2)C=2NC3=CC(Br)=CC=C3N=2)=C1 HBVCXUNMLJPSFB-UHFFFAOYSA-N 0.000 claims 1
- BDKBNCKILMILOE-GOSISDBHSA-N 6-chloro-2-[(2r)-1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(C)C(C)=CC=C1CN1[C@@H](C=2NC3=CC(Cl)=CN=C3N=2)CCCC1 BDKBNCKILMILOE-GOSISDBHSA-N 0.000 claims 1
- SBRDCIZEAUSTSZ-UHFFFAOYSA-N 6-chloro-2-[1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-1h-benzimidazole Chemical compound C1=C(C)C(C)=CC=C1CN1C(C=2NC3=CC(Cl)=CC=C3N=2)CCCC1 SBRDCIZEAUSTSZ-UHFFFAOYSA-N 0.000 claims 1
- BDKBNCKILMILOE-UHFFFAOYSA-N 6-chloro-2-[1-[(3,4-dimethylphenyl)methyl]piperidin-2-yl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=C(C)C(C)=CC=C1CN1C(C=2NC3=CC(Cl)=CN=C3N=2)CCCC1 BDKBNCKILMILOE-UHFFFAOYSA-N 0.000 claims 1
- LDXWYKHFWRVGTF-UHFFFAOYSA-N 6-chloro-2-[1-[(3-methylphenyl)methyl]piperidin-2-yl]-1h-benzimidazole Chemical compound CC1=CC=CC(CN2C(CCCC2)C=2NC3=CC(Cl)=CC=C3N=2)=C1 LDXWYKHFWRVGTF-UHFFFAOYSA-N 0.000 claims 1
- NNONZLPUZSUOLW-UHFFFAOYSA-N 6-chloro-2-[1-[(4-fluorophenyl)methyl]piperidin-2-yl]-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC(F)=CC=C1CN1C(C=2NC3=CC(Cl)=CN=C3N=2)CCCC1 NNONZLPUZSUOLW-UHFFFAOYSA-N 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000005576 amination reaction Methods 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 208000035474 group of disease Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 208000014341 psoriasis 7 Diseases 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 230000005747 tumor angiogenesis Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11007796.3 | 2011-09-26 | ||
| EP11007796 | 2011-09-26 | ||
| PCT/EP2012/003771 WO2013045028A1 (en) | 2011-09-26 | 2012-09-07 | Benzyl piperidine compounds as lysophosphatidic acid (lpa) receptor antagonist |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014526526A JP2014526526A (ja) | 2014-10-06 |
| JP2014526526A5 true JP2014526526A5 (enExample) | 2015-11-05 |
| JP6163156B2 JP6163156B2 (ja) | 2017-07-12 |
Family
ID=46845693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014531124A Expired - Fee Related JP6163156B2 (ja) | 2011-09-26 | 2012-09-07 | リゾホスファチジン酸（ｌｐａ）受容体アンタゴニストとしてのベンジルピペリジン化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9527850B2 (enExample) |
| EP (1) | EP2844648B1 (enExample) |
| JP (1) | JP6163156B2 (enExample) |
| CN (1) | CN103814024B (enExample) |
| AU (1) | AU2012314943B9 (enExample) |
| CA (1) | CA2849820C (enExample) |
| ES (1) | ES2612934T3 (enExample) |
| IL (1) | IL231699A (enExample) |
| WO (1) | WO2013045028A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013116291A1 (en) * | 2012-01-30 | 2013-08-08 | Cephalon, Inc. | Imidazo [4, 5 - b] pyridine derivatives as alk and jak modulators for the treatment of proliferative disorders |
| US10913736B2 (en) * | 2014-08-22 | 2021-02-09 | University Of Washington | Specific inhibitors of methionyl-tRNA synthetase |
| JP7054529B2 (ja) | 2016-06-21 | 2022-04-14 | エックス４ ファーマシューティカルズ， インコーポレイテッド | Ｃｘｃｒ４阻害剤およびその使用 |
| CA3027500A1 (en) * | 2016-06-21 | 2017-12-28 | X4 Pharmaceuticals, Inc. | Cxcr4 inhibitors and uses thereof |
| JPWO2018016523A1 (ja) * | 2016-07-20 | 2019-05-09 | 国立大学法人 長崎大学 | 新規放射線防護剤 |
| WO2020007964A1 (en) * | 2018-07-05 | 2020-01-09 | Idorsia Pharmaceuticals Ltd | 2-(2-azabicyclo[3.1.0]hexan-1-yl)-1h-benzimidazole derivatives |
| CN113461640B (zh) * | 2021-06-17 | 2023-08-11 | 中央民族大学 | Lpar1抑制剂、医药用途及其制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB804786A (en) * | 1955-12-16 | 1958-11-26 | Rhone Poulenc Sa | New indole derivatives and process for their preparation |
| FR2666582B1 (fr) * | 1990-09-07 | 1994-09-02 | Synthelabo | Derives de benzimidazole, leur preparation et leur application en therapeutique. |
| ES2048109B1 (es) * | 1992-07-20 | 1994-12-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol. |
| JP4766384B2 (ja) * | 2003-12-19 | 2011-09-07 | 小野薬品工業株式会社 | リゾホスファチジン酸受容体拮抗作用を有する化合物およびその用途 |
| HRP20161562T2 (hr) * | 2007-06-29 | 2017-04-21 | Pfizer Inc. | Derivati benzimidazola |
| US20090062268A1 (en) * | 2007-08-27 | 2009-03-05 | Lead Therapeutics, Inc. | Novel inhibitors of poly(adp-ribose)polymerase (parp) |
| CA2712946A1 (en) * | 2008-02-13 | 2009-08-20 | Merck Sharp & Dohme Corp. | Quinolizidinone m1 receptor positive allosteric modulators |
| EA201100879A1 (ru) * | 2008-12-01 | 2012-01-30 | Мерк Патент Гмбх | Производные пиридопиримидина в качестве ингибиторов аутотаксина |
| EP2623101B1 (en) * | 2009-04-02 | 2021-04-21 | Merck Patent GmbH | Piperidine and piperazine derivatives as autotaxin inhibitors |
-
2012
- 2012-09-07 AU AU2012314943A patent/AU2012314943B9/en not_active Ceased
- 2012-09-07 WO PCT/EP2012/003771 patent/WO2013045028A1/en not_active Ceased
- 2012-09-07 CN CN201280046889.6A patent/CN103814024B/zh not_active Expired - Fee Related
- 2012-09-07 CA CA2849820A patent/CA2849820C/en not_active Expired - Fee Related
- 2012-09-07 US US14/344,267 patent/US9527850B2/en not_active Expired - Fee Related
- 2012-09-07 JP JP2014531124A patent/JP6163156B2/ja not_active Expired - Fee Related
- 2012-09-07 EP EP12758777.2A patent/EP2844648B1/en not_active Not-in-force
- 2012-09-07 ES ES12758777.2T patent/ES2612934T3/es active Active
-
2014
- 2014-03-25 IL IL231699A patent/IL231699A/en active IP Right Grant
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2477723C2 (ru) | Ингибиторы протеинкиназ (варианты), их применение для лечения онкологических заболеваний и фармацевтическая композиция на их основе | |
| JP6505023B2 (ja) | Ｃｎｓおよび他の障害を治療するための、ｐｄｅ４アイソザイムの阻害薬としてのアザベンゾイミダゾール化合物 | |
| TW201927756A (zh) | 整合應激路徑之調節劑 | |
| JP2013510120A5 (enExample) | ||
| JP2011511073A5 (enExample) | ||
| WO2009115517A3 (en) | Pyridines and pyrazines as inhibitors of pi3k | |
| JP2016504290A5 (enExample) | ||
| MX2010007714A (es) | Piridinas fusionadas activas como inhibidores de c-met. | |
| JP2016525076A5 (enExample) | ||
| JP2009536620A5 (enExample) | ||
| EA201301302A1 (ru) | Производные пиридина и пиразина | |
| JP2016525075A5 (enExample) | ||
| JP2017528475A5 (enExample) | ||
| JP2013516479A5 (enExample) | ||
| JP2014511892A5 (enExample) | ||
| MX2010010647A (es) | Proceso para preparar formulaciones de dabigatran para administracion oral. | |
| JP2014520898A5 (enExample) | ||
| NZ613235A (en) | Substituted n-(1h-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide compounds as type iii receptor tyrosine kinase inhibitors | |
| PE20141167A1 (es) | Piridopirazinas sustituidas como inhibidores novedosos de ptk | |
| CA2973773C (en) | 2-phenyl-3h-imidazo[4,5-b]pyridine derivatives useful as inhibitors of mammalian tyrosine kinase ror1 activity | |
| JP2015500884A5 (enExample) | ||
| CA2729833A1 (fr) | Derives de pyridino-pyridinones, leur preparation et leur application en therapeutique | |
| RU2015147447A (ru) | Производные доластатина 10 и ауристатинов | |
| PE20081159A1 (es) | Inhibidores de las quinasas y metodos para su utilizacion | |
| TW202003485A (zh) | 原肌球蛋白相關之激酶（ｔｒｋ）抑制劑 |