ES2875734T3 - Derivados de 9H-pirrolo-dipiridina - Google Patents
Derivados de 9H-pirrolo-dipiridina Download PDFInfo
- Publication number
- ES2875734T3 ES2875734T3 ES16702121T ES16702121T ES2875734T3 ES 2875734 T3 ES2875734 T3 ES 2875734T3 ES 16702121 T ES16702121 T ES 16702121T ES 16702121 T ES16702121 T ES 16702121T ES 2875734 T3 ES2875734 T3 ES 2875734T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrrolo
- dipyridine
- methyl
- dipyridin
- mmol
- 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.)
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- -1 di-methyl-amino Chemical group 0.000 claims abstract description 321
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 80
- 239000011737 fluorine Substances 0.000 claims abstract description 79
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 79
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 60
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 46
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 40
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 38
- 230000002285 radioactive effect Effects 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 24
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 19
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims abstract description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052722 tritium Chemical group 0.000 claims abstract description 18
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims abstract description 17
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
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- 230000003287 optical effect Effects 0.000 claims abstract description 13
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 12
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
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- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 14
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- CYLWDEZKPRWZMU-UHFFFAOYSA-N 11-(1H-pyrazol-5-yl)-4,8,10-triazatricyclo[7.4.0.02,7]trideca-1(9),2(7),3,5,10,12-hexaene Chemical compound N1N=CC=C1C1=NC2=C(C=C1)C1=CN=CC=C1N2 CYLWDEZKPRWZMU-UHFFFAOYSA-N 0.000 claims description 6
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0455—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0459—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0463—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Physics & Mathematics (AREA)
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- General Chemical & Material Sciences (AREA)
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- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
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| EP15153448 | 2015-02-02 | ||
| PCT/EP2016/051993 WO2016124508A1 (en) | 2015-02-02 | 2016-01-29 | 9h-pyrrolo-dipyridine derivatives |
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| ES2875734T3 true ES2875734T3 (es) | 2021-11-11 |
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| ES16702121T Active ES2875734T3 (es) | 2015-02-02 | 2016-01-29 | Derivados de 9H-pirrolo-dipiridina |
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| MY (1) | MY191590A (enExample) |
| SG (1) | SG11201705727TA (enExample) |
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| WO2009102498A1 (en) | 2008-02-14 | 2009-08-20 | Siemens Medical Solutions Usa, Inc. | Novel imaging agents for detecting neurological dysfunction |
| WO2016124508A1 (en) * | 2015-02-02 | 2016-08-11 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
| JP7059270B2 (ja) * | 2016-07-22 | 2022-04-25 | エーシー・イミューン・エス・アー | タウタンパク質凝集体を画像化するための化合物 |
| SG11201811311VA (en) | 2016-07-22 | 2019-01-30 | Ac Immune Sa | Compounds for imaging tau protein aggregates |
| 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 |
| AU2017367872B2 (en) * | 2016-11-01 | 2022-03-31 | Arvinas, Inc. | Tau-protein targeting protacs and associated methods of use |
| JPWO2018221728A1 (ja) | 2017-06-02 | 2020-04-02 | 富士フイルム富山化学株式会社 | アルツハイマー型認知症予防または治療剤 |
| CN110691595A (zh) | 2017-06-02 | 2020-01-14 | 富士胶片富山化学株式会社 | β-淀粉样蛋白量减少剂 |
| JP7133547B2 (ja) | 2017-06-02 | 2022-09-08 | 富士フイルム富山化学株式会社 | 脊髄小脳変性症予防または治療剤 |
| JP7370859B2 (ja) * | 2017-06-02 | 2023-10-30 | 富士フイルム富山化学株式会社 | タウオパチー予防または治療剤 |
| CN116473962A (zh) | 2017-06-02 | 2023-07-25 | 富士胶片富山化学株式会社 | 脑萎缩预防或治疗剂 |
| WO2019088083A1 (ja) | 2017-10-30 | 2019-05-09 | 富士フイルム富山化学株式会社 | エモパミル結合タンパク質結合剤およびその利用 |
| US11306089B2 (en) | 2018-01-24 | 2022-04-19 | Life Molecular Imaging Limited | Gamma-carboline compounds for the detection of Tau aggregates |
| US20210041447A1 (en) * | 2018-01-24 | 2021-02-11 | Ac Immune Sa | Azacarboline compounds for the detection of tau aggregates |
| CN111868062B (zh) * | 2018-01-24 | 2023-07-07 | Ac免疫有限公司 | 制备显像化合物的方法 |
| CN114867727B (zh) | 2019-07-17 | 2025-02-21 | 阿尔维纳斯运营股份有限公司 | Tau蛋白靶向化合物及相关使用方法 |
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| WO2008132454A1 (en) * | 2007-04-26 | 2008-11-06 | Ge Healthcare Limited | Carbolines and their use as imaging agents |
| WO2009102498A1 (en) * | 2008-02-14 | 2009-08-20 | Siemens Medical Solutions Usa, Inc. | Novel imaging agents for detecting neurological dysfunction |
| CN102325752B (zh) * | 2008-12-19 | 2015-02-04 | 百时美施贵宝公司 | 咔唑和咔啉激酶抑制剂 |
| CA2873963C (en) * | 2012-05-22 | 2017-04-11 | Eli Lilly And Company | Carboline and carbazole based imaging agents for detecting neurological dysfunction |
| US20160115162A1 (en) | 2013-05-31 | 2016-04-28 | 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 |
| WO2016124508A1 (en) * | 2015-02-02 | 2016-08-11 | Ucb Biopharma Sprl | 9h-pyrrolo-dipyridine derivatives |
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| EA036518B1 (ru) | 2020-11-18 |
| CA2973648C (en) | 2023-09-26 |
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| DK3253762T3 (da) | 2021-07-19 |
| BR112017016311A2 (pt) | 2018-03-27 |
| CL2017001923A1 (es) | 2018-02-16 |
| US20220213103A1 (en) | 2022-07-07 |
| KR20170113607A (ko) | 2017-10-12 |
| EP3253762A1 (en) | 2017-12-13 |
| WO2016124508A1 (en) | 2016-08-11 |
| AU2016214537B2 (en) | 2018-05-10 |
| EA201791733A1 (ru) | 2018-01-31 |
| US12006316B2 (en) | 2024-06-11 |
| US11312716B2 (en) | 2022-04-26 |
| MX2017009505A (es) | 2017-11-02 |
| US20180022748A1 (en) | 2018-01-25 |
| SG11201705727TA (en) | 2017-08-30 |
| CN107207508A (zh) | 2017-09-26 |
| CA2973648A1 (en) | 2016-08-11 |
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