JP2018526410A5 - - Google Patents
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- Publication number
- JP2018526410A5 JP2018526410A5 JP2018512604A JP2018512604A JP2018526410A5 JP 2018526410 A5 JP2018526410 A5 JP 2018526410A5 JP 2018512604 A JP2018512604 A JP 2018512604A JP 2018512604 A JP2018512604 A JP 2018512604A JP 2018526410 A5 JP2018526410 A5 JP 2018526410A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrahydro
- azabicyclo
- endo
- octane
- amine
- 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
- 229910052736 halogen Inorganic materials 0.000 claims description 90
- 150000002367 halogens Chemical class 0.000 claims description 90
- -1 3 -Methyl-1,2-thiazol-5-yl Chemical group 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 9
- 206010012289 Dementia Diseases 0.000 claims 6
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 4
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 208000024667 ABeta amyloidosis, Dutch type Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 3
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 3
- 201000010374 Down Syndrome Diseases 0.000 claims 3
- 206010044688 Trisomy 21 Diseases 0.000 claims 3
- 206010008118 cerebral infarction Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 208000036536 dutch type ABeta amyloidosis Diseases 0.000 claims 3
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 2
- GDQYFKGLAUOXST-UHFFFAOYSA-N indolizin-2-amine Chemical compound C1=CC=CN2C=C(N)C=C21 GDQYFKGLAUOXST-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- QGCRJRVFQZXCAZ-UHFFFAOYSA-N 1h-triazolo[1,5-a]pyridin-2-amine Chemical compound C1=CC=CC2=CN(N)NN21 QGCRJRVFQZXCAZ-UHFFFAOYSA-N 0.000 claims 1
- FZAXBPZVVJOFKX-UHFFFAOYSA-N 3-methyl-1,2,4-oxadiazole Chemical compound CC=1N=CON=1 FZAXBPZVVJOFKX-UHFFFAOYSA-N 0.000 claims 1
- KMOCWZDDMSUAPI-UHFFFAOYSA-N 8-(2,3,4-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound NC1=NN2CCCC(C2=N1)C1=C(F)C(F)=C(F)C=C1 KMOCWZDDMSUAPI-UHFFFAOYSA-N 0.000 claims 1
- RKOTXQYWCBGZLP-UHFFFAOYSA-N N-[(2,4-difluorophenyl)methyl]-2-ethyl-9-hydroxy-3-methoxy-1,8-dioxospiro[3H-pyrido[1,2-a]pyrazine-4,3'-oxolane]-7-carboxamide Chemical compound CCN1C(OC)C2(CCOC2)N2C=C(C(=O)NCC3=C(F)C=C(F)C=C3)C(=O)C(O)=C2C1=O RKOTXQYWCBGZLP-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 0 CCCCC(CCCCCC[C@]1C=*C)CCC(C2)C2C1N(CC1CC2)CC2C1Nc1n[n](C(C)C(*)CC2C3=CC=C*(*)C=C3)c2n1 Chemical compound CCCCC(CCCCCC[C@]1C=*C)CCC(C2)C2C1N(CC1CC2)CC2C1Nc1n[n](C(C)C(*)CC2C3=CC=C*(*)C=C3)c2n1 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BSOVAWQWIYEOAI-UHFFFAOYSA-N 2-bromo-8-[4-(trifluoromethylsulfanyl)phenyl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC(F)(F)SC1=CC=C(C=C1)C1=CC=CN2N=C(Br)N=C12 BSOVAWQWIYEOAI-UHFFFAOYSA-N 0.000 description 1
- DLILBKMOUOQUPL-UHFFFAOYSA-N 5-(trifluoromethyl)-8-(2,3,4-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-2-amine Chemical compound NC1=NN2C(CCC(C2=N1)C1=C(F)C(F)=C(F)C=C1)C(F)(F)F DLILBKMOUOQUPL-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LNAMMBFJMYMQTO-FNEBRGMMSA-N chloroform;(1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].ClC(Cl)Cl.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 LNAMMBFJMYMQTO-FNEBRGMMSA-N 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical compound CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15184480.0 | 2015-09-09 | ||
| EP15184480 | 2015-09-09 | ||
| PCT/EP2016/070800 WO2017042114A1 (en) | 2015-09-09 | 2016-09-05 | Bridged piperidine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018526410A JP2018526410A (ja) | 2018-09-13 |
| JP2018526410A5 true JP2018526410A5 (OSRAM) | 2019-09-26 |
| JP6831372B2 JP6831372B2 (ja) | 2021-02-17 |
Family
ID=54072754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018512604A Active JP6831372B2 (ja) | 2015-09-09 | 2016-09-05 | 架橋ピペリジン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10604517B2 (OSRAM) |
| EP (1) | EP3347363B1 (OSRAM) |
| JP (1) | JP6831372B2 (OSRAM) |
| CN (1) | CN107922437B (OSRAM) |
| AR (1) | AR105965A1 (OSRAM) |
| TW (1) | TWI716446B (OSRAM) |
| WO (1) | WO2017042114A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017042114A1 (en) | 2015-09-09 | 2017-03-16 | F. Hoffmann-La Roche Ag | Bridged piperidine derivatives |
| EP3475279B1 (en) * | 2016-06-27 | 2021-07-14 | F. Hoffmann-La Roche AG | Triazolopyridines as gamma-secretase modulators |
| ES2847903T3 (es) | 2016-09-09 | 2021-08-04 | Hoffmann La Roche | Procedimiento para la preparación de 2-(6-nitropiridin-3-il)-9H-dipirido[2,3-b;3',4'-d]pirrol |
| AR109829A1 (es) * | 2016-09-29 | 2019-01-30 | Hoffmann La Roche | Derivados de piperidina puenteados |
| CN109476670B (zh) | 2016-10-04 | 2022-06-28 | 豪夫迈·罗氏有限公司 | 二环杂芳基衍生物 |
| AR110001A1 (es) * | 2016-11-01 | 2019-02-13 | Hoffmann La Roche | Derivados heteroarilo bicíclicos |
| WO2019121434A1 (en) * | 2017-12-18 | 2019-06-27 | F. Hoffmann-La Roche Ag | Triazolo-azepine derivatives |
| WO2019141832A1 (en) * | 2018-01-22 | 2019-07-25 | F. Hoffmann-La Roche Ag | Triazolo-azepine derivatives |
| HUE064554T2 (hu) * | 2018-09-03 | 2024-03-28 | Hoffmann La Roche | Bicikluszos heteroaril származékok |
| PL3894411T3 (pl) | 2018-12-13 | 2024-10-07 | F. Hoffmann-La Roche Ag | Pochodne 7-fenoksy-N-(3-azabicyklo[3.2.1]oktan-8-ylo)-6,7-dihydro-5H-pirolo[1,2-b][1,2,4]triazolo-2-aminy i związki pokrewne jako modulatory gamma-sekretazy do leczenia choroby Alzheimera |
| AU2019412747B8 (en) | 2018-12-27 | 2025-04-24 | F. Hoffmann-La Roche Ag | Process for the preparation exo-tert-butyl N-(3-azabicyclo[3.2.1]octan-8-yl)carbamate |
| EP3956330A4 (en) | 2019-04-18 | 2023-01-18 | The Johns Hopkins University | SUBSTITUTED 2-AMINO-PYRAZOLYL-[1,2,4]TRIAZOLO[1,5A]PYRIDINE DERIVATIVES AND THEIR USE |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003211993A1 (en) * | 2002-02-15 | 2003-09-04 | Kyowa Hakko Kogyo Co., Ltd. | (1,2,4)TRIAZOLO(1,5-c)PYRIMIDINE DERIVATIVES |
| RU2010137300A (ru) * | 2008-02-22 | 2012-03-27 | Ф. Хоффманн-Ля Рош Аг (Ch) | Модуляторы бета-амилоида |
| CN102047454B (zh) * | 2008-04-16 | 2013-04-10 | Lg伊诺特有限公司 | 发光器件及其制造方法 |
| MX2011004954A (es) * | 2008-11-10 | 2011-05-30 | Hoffmann La Roche | Moduladores heterociclicos de gamma-secretasa. |
| TWI461425B (zh) * | 2009-02-19 | 2014-11-21 | Janssen Pharmaceuticals Inc | 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類 |
| WO2010145883A1 (en) * | 2009-05-07 | 2010-12-23 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc | Novel substituted indazole and aza-indazole derivatives as gamma secretase modulators |
| WO2010138901A1 (en) * | 2009-05-29 | 2010-12-02 | Biogen Idec Ma Inc | Carboxylic acid-containing compounds, derivatives thereof, and related methods of use |
| US20110117966A1 (en) * | 2009-10-23 | 2011-05-19 | Appsware Wireless, Llc | System and Device for Consolidating SIM, Personal Token, and Associated Applications |
| US20110190269A1 (en) * | 2010-02-01 | 2011-08-04 | Karlheinz Baumann | Gamma secretase modulators |
| US8486967B2 (en) * | 2010-02-17 | 2013-07-16 | Hoffmann-La Roche Inc. | Heteroaryl substituted piperidines |
| US8703763B2 (en) * | 2011-03-02 | 2014-04-22 | Hoffmann-La Roche Inc. | Bridged piperidine derivatives |
| EP2687528A1 (en) * | 2012-07-17 | 2014-01-22 | Ares Trading S.A. | Fused triazole derivatives as gamma secretase modulators |
| WO2017042114A1 (en) | 2015-09-09 | 2017-03-16 | F. Hoffmann-La Roche Ag | Bridged piperidine derivatives |
-
2016
- 2016-09-05 WO PCT/EP2016/070800 patent/WO2017042114A1/en not_active Ceased
- 2016-09-05 JP JP2018512604A patent/JP6831372B2/ja active Active
- 2016-09-05 EP EP16763491.4A patent/EP3347363B1/en active Active
- 2016-09-05 CN CN201680051165.9A patent/CN107922437B/zh active Active
- 2016-09-08 TW TW105129076A patent/TWI716446B/zh not_active IP Right Cessation
- 2016-09-08 AR ARP160102743A patent/AR105965A1/es unknown
-
2018
- 2018-03-06 US US15/913,087 patent/US10604517B2/en active Active
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