JP2018503673A5 - - Google Patents
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- Publication number
- JP2018503673A5 JP2018503673A5 JP2017540724A JP2017540724A JP2018503673A5 JP 2018503673 A5 JP2018503673 A5 JP 2018503673A5 JP 2017540724 A JP2017540724 A JP 2017540724A JP 2017540724 A JP2017540724 A JP 2017540724A JP 2018503673 A5 JP2018503673 A5 JP 2018503673A5
- Authority
- JP
- Japan
- Prior art keywords
- halogen
- optionally substituted
- pyrrolo
- alkoxy
- alkyl
- 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 75
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 60
- 125000005843 halogen group Chemical group 0.000 claims 55
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 50
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 48
- -1 cyano, amino Chemical group 0.000 claims 41
- 150000001875 compounds Chemical class 0.000 claims 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 28
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 24
- 229910052731 fluorine Inorganic materials 0.000 claims 24
- 239000011737 fluorine Substances 0.000 claims 24
- 125000001153 fluoro group Chemical group F* 0.000 claims 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 20
- 150000002367 halogens Chemical class 0.000 claims 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 15
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 14
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims 12
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 12
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 12
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 11
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 7
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 6
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 230000003287 optical effect Effects 0.000 claims 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 3
- 235000005152 nicotinamide Nutrition 0.000 claims 3
- 239000011570 nicotinamide Substances 0.000 claims 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910004013 NO 2 Inorganic materials 0.000 claims 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 230000002285 radioactive effect Effects 0.000 claims 2
- 229910052722 tritium Chemical group 0.000 claims 2
- HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims 1
- NAEQZBNOUXKFFI-UHFFFAOYSA-N 11-(1H-pyrazol-4-yl)-4,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene Chemical compound c1n[nH]cc1-c1ccc2c(n1)[nH]c1ccncc21 NAEQZBNOUXKFFI-UHFFFAOYSA-N 0.000 claims 1
- FUMZJKNGBMBNRB-UHFFFAOYSA-N 11-(1H-pyrazol-4-yl)-5,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene Chemical compound N1C=C(C=N1)C1=NC2=C(C=C1)C1=CC=NC=C1N2 FUMZJKNGBMBNRB-UHFFFAOYSA-N 0.000 claims 1
- VSDNGHSDNIOQKJ-UHFFFAOYSA-N 11-pyridin-3-yl-4,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene Chemical compound c1cncc(c1)-c1ccc2c(n1)[nH]c1ccncc21 VSDNGHSDNIOQKJ-UHFFFAOYSA-N 0.000 claims 1
- LEYKWMQWDLHJTO-UHFFFAOYSA-N 11-pyridin-4-yl-4,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene Chemical compound c1cc(ccn1)-c1ccc2c(n1)[nH]c1ccncc21 LEYKWMQWDLHJTO-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ZGSNZVRXASCXRP-UHFFFAOYSA-N 5-methoxy-1h-pyrazole Chemical group COC=1C=CNN=1 ZGSNZVRXASCXRP-UHFFFAOYSA-N 0.000 claims 1
- IBBMAWULFFBRKK-IBTRZKOZSA-N 6-tritiopyridine-2-carboxamide Chemical compound N1=C(C=CC=C1[3H])C(=O)N IBBMAWULFFBRKK-IBTRZKOZSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 238000003384 imaging method Methods 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 238000012544 monitoring process Methods 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 150000003053 piperidines Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- IIHQNAXFIODVDU-UHFFFAOYSA-N pyrimidine-2-carbonitrile Chemical compound N#CC1=NC=CC=N1 IIHQNAXFIODVDU-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15153448 | 2015-02-02 | ||
| EP15153448.4 | 2015-02-02 | ||
| PCT/EP2016/051993 WO2016124508A1 (en) | 2015-02-02 | 2016-01-29 | 9h-pyrrolo-dipyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018503673A JP2018503673A (ja) | 2018-02-08 |
| JP2018503673A5 true JP2018503673A5 (enExample) | 2018-09-06 |
| JP6579670B2 JP6579670B2 (ja) | 2019-09-25 |
Family
ID=52477553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017540724A Active JP6579670B2 (ja) | 2015-02-02 | 2016-01-29 | ９ｈ−ピロロ−ジピリジン誘導体 |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US20180022748A1 (enExample) |
| EP (1) | EP3253762B1 (enExample) |
| JP (1) | JP6579670B2 (enExample) |
| KR (1) | KR102621513B1 (enExample) |
| CN (1) | CN107207508B (enExample) |
| AU (1) | AU2016214537B2 (enExample) |
| BR (1) | BR112017016311A2 (enExample) |
| CA (1) | CA2973648C (enExample) |
| CL (1) | CL2017001923A1 (enExample) |
| DK (1) | DK3253762T3 (enExample) |
| EA (1) | EA036518B1 (enExample) |
| ES (1) | ES2875734T3 (enExample) |
| IL (1) | IL253381B (enExample) |
| MX (1) | MX378155B (enExample) |
| MY (1) | MY191590A (enExample) |
| SG (1) | SG11201705727TA (enExample) |
| WO (1) | WO2016124508A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110046378A1 (en) | 2008-02-14 | 2011-02-24 | Siemens Medical Solutions Usa, Inc. | Novel Imaging Agents for Detecting Neurological Dysfunction |
| EP3253762B1 (en) * | 2015-02-02 | 2021-05-05 | UCB Biopharma SRL | 9h-pyrrolo-dipyridine derivatives |
| SG11201811311VA (en) * | 2016-07-22 | 2019-01-30 | Ac Immune Sa | Compounds for imaging tau protein aggregates |
| US10865207B2 (en) | 2016-07-22 | 2020-12-15 | Ac Immune S.A. | Compounds for imaging Tau protein aggregates |
| WO2018046428A1 (en) * | 2016-09-09 | 2018-03-15 | F. Hoffmann-La Roche Ag | Process for preparation of 2-(6-nitropyridin-3-yl)-9h-dipyrido[2,3-b;3',4'-d]pyrrole |
| IL304982A (en) * | 2016-11-01 | 2023-10-01 | Arvinas Operations Inc | PROTACS Targeted Tau-Protein and Related Methods of Use |
| EP3636262A4 (en) | 2017-06-02 | 2020-06-10 | FUJIFILM Toyama Chemical Co., Ltd. | AGENT FOR PREVENTING OR TREATING ALZHEIMER-LIKE DEMENTIA |
| KR20220101001A (ko) * | 2017-06-02 | 2022-07-18 | 후지필름 도야마 케미컬 가부시키가이샤 | 타우병증 예방 또는 치료제 |
| CA3067453C (en) | 2017-06-02 | 2021-11-23 | Fujifilm Toyama Chemical Co., Ltd. | Agent for preventing or treating brain atrophy |
| US11666551B2 (en) | 2017-06-02 | 2023-06-06 | Fujifilm Toyama Chemical Co., Ltd. | Agent for reducing amount of amyloid β protein |
| WO2018221730A1 (ja) | 2017-06-02 | 2018-12-06 | 富山化学工業株式会社 | 脊髄小脳変性症予防または治療剤 |
| US11548878B2 (en) | 2017-10-30 | 2023-01-10 | Fujifilm Toyama Chemical Co., Ltd. | Emopamil binding protein binding agent and use thereof |
| EP3743426A1 (en) * | 2018-01-24 | 2020-12-02 | AC Immune SA | Azacarboline compounds for the detection of tau aggregates |
| EP3743427B1 (en) * | 2018-01-24 | 2022-10-19 | AC Immune SA | Novel method of preparing an imaging compound |
| EP3743423A1 (en) | 2018-01-24 | 2020-12-02 | AC Immune SA | Gamma-carboline compounds for the detection of tau aggregates |
| EP3999182A1 (en) | 2019-07-17 | 2022-05-25 | Arvinas Operations, Inc. | Tau-protein targeting compounds and associated methods of use |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1268771A (en) | 1968-03-15 | 1972-03-29 | Glaxo Lab Ltd | Azacarbazoles |
| WO2008132454A1 (en) * | 2007-04-26 | 2008-11-06 | Ge Healthcare Limited | Carbolines and their use as imaging agents |
| US20110046378A1 (en) * | 2008-02-14 | 2011-02-24 | Siemens Medical Solutions Usa, Inc. | Novel Imaging Agents for Detecting Neurological Dysfunction |
| US8815840B2 (en) * | 2008-12-19 | 2014-08-26 | Bristol-Myers Squibb Company | Carbazole and carboline kinase inhibitors |
| EP2852572B1 (en) * | 2012-05-22 | 2020-04-01 | Eli Lilly and Company | Carboline and carbazole based imaging agents for detecting neurological dysfunction |
| WO2014194169A1 (en) | 2013-05-31 | 2014-12-04 | The General Hospital Corporation | Radiosynthesis of tau radiopharmaceuticals |
| WO2015010263A1 (en) * | 2013-07-24 | 2015-01-29 | Telefonaktiebolaget L M Ericsson(Publ) | Method and apparautus relating to reception of radio signals |
| PT3055308T (pt) * | 2013-10-08 | 2018-01-18 | Hoffmann La Roche | Resumo |
| US10662193B2 (en) * | 2014-01-21 | 2020-05-26 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyloid-like proteins |
| EP3253762B1 (en) * | 2015-02-02 | 2021-05-05 | UCB Biopharma SRL | 9h-pyrrolo-dipyridine derivatives |
-
2016
- 2016-01-29 EP EP16702121.1A patent/EP3253762B1/en active Active
- 2016-01-29 CN CN201680008314.3A patent/CN107207508B/zh active Active
- 2016-01-29 US US15/547,980 patent/US20180022748A1/en not_active Abandoned
- 2016-01-29 KR KR1020177024371A patent/KR102621513B1/ko active Active
- 2016-01-29 DK DK16702121.1T patent/DK3253762T3/da active
- 2016-01-29 MY MYPI2017702668A patent/MY191590A/en unknown
- 2016-01-29 JP JP2017540724A patent/JP6579670B2/ja active Active
- 2016-01-29 WO PCT/EP2016/051993 patent/WO2016124508A1/en not_active Ceased
- 2016-01-29 AU AU2016214537A patent/AU2016214537B2/en active Active
- 2016-01-29 ES ES16702121T patent/ES2875734T3/es active Active
- 2016-01-29 CA CA2973648A patent/CA2973648C/en active Active
- 2016-01-29 MX MX2017009505A patent/MX378155B/es unknown
- 2016-01-29 SG SG11201705727TA patent/SG11201705727TA/en unknown
- 2016-01-29 BR BR112017016311A patent/BR112017016311A2/pt not_active Application Discontinuation
- 2016-01-29 EA EA201791733A patent/EA036518B1/ru not_active IP Right Cessation
-
2017
- 2017-07-10 IL IL253381A patent/IL253381B/en active IP Right Grant
- 2017-07-27 CL CL2017001923A patent/CL2017001923A1/es unknown
-
2020
- 2020-01-22 US US16/749,537 patent/US11312716B2/en active Active
-
2022
- 2022-03-21 US US17/700,075 patent/US12006316B2/en active Active
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