JP2014526526A5 - - Google Patents
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- 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 (https=) | 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 (https=) |
| EP (1) | EP2844648B1 (https=) |
| JP (1) | JP6163156B2 (https=) |
| CN (1) | CN103814024B (https=) |
| AU (1) | AU2012314943B9 (https=) |
| CA (1) | CA2849820C (https=) |
| ES (1) | ES2612934T3 (https=) |
| IL (1) | IL231699A (https=) |
| WO (1) | WO2013045028A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2567552T3 (es) * | 2012-01-30 | 2016-04-25 | Cephalon, Inc. | Imidazo [4,5-b] derivados de piridina como los moduladores ALK y JAK para el tratamiento de trastornos proliferativos |
| WO2016029146A1 (en) * | 2014-08-22 | 2016-02-25 | University Of Washington | Specific inhibitors of methionyl-trna synthetase |
| ES2870920T3 (es) | 2016-06-21 | 2021-10-28 | X4 Pharmaceuticals Inc | Inhibidores de CXCR4 y usos de los mismos |
| WO2017223243A1 (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. |
| ATE528276T1 (de) * | 2003-12-19 | 2011-10-15 | Ono Pharmaceutical Co | Lysophosphatidylsäurerezeptor-antagonistische verbindungen und ihre anwendungen |
| KR101143246B1 (ko) * | 2007-06-29 | 2012-05-18 | 화이자 인코포레이티드 | 벤즈이미다졸 유도체 |
| US20090062268A1 (en) * | 2007-08-27 | 2009-03-05 | Lead Therapeutics, Inc. | Novel inhibitors of poly(adp-ribose)polymerase (parp) |
| AU2009215111A1 (en) * | 2008-02-13 | 2009-08-20 | Merck Sharp & Dohme Corp. | Quinolizidinone M1 receptor positive allosteric modulators |
| WO2010063352A1 (en) * | 2008-12-01 | 2010-06-10 | Merck Patent Gmbh | 2, 5-diamino-substituted pyrido [4, 3-d] pyrimidines as autotaxin inhibitors against cancer |
| KR20120027177A (ko) * | 2009-04-02 | 2012-03-21 | 메르크 파텐트 게엠베하 | 오토탁신 저해제로서의 피페리딘 및 피라진 유도체 |
-
2012
- 2012-09-07 AU AU2012314943A patent/AU2012314943B9/en not_active Ceased
- 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 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 ES ES12758777.2T patent/ES2612934T3/es active Active
- 2012-09-07 US US14/344,267 patent/US9527850B2/en not_active Expired - Fee Related
-
2014
- 2014-03-25 IL IL231699A patent/IL231699A/en active IP Right Grant
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