HRP20210051T1 - Spojevi pirazina kao modulatori map kinaze i njihove uporabe - Google Patents
Spojevi pirazina kao modulatori map kinaze i njihove uporabe Download PDFInfo
- Publication number
- HRP20210051T1 HRP20210051T1 HRP20210051TT HRP20210051T HRP20210051T1 HR P20210051 T1 HRP20210051 T1 HR P20210051T1 HR P20210051T T HRP20210051T T HR P20210051TT HR P20210051 T HRP20210051 T HR P20210051T HR P20210051 T1 HRP20210051 T1 HR P20210051T1
- Authority
- HR
- Croatia
- Prior art keywords
- naphthalen
- alkyl
- independently
- halogen
- isoquinolin
- Prior art date
Links
- 108091000080 Phosphotransferase Proteins 0.000 title 1
- 102000020233 phosphotransferase Human genes 0.000 title 1
- 150000003216 pyrazines Chemical class 0.000 title 1
- -1 indol-4-yl Chemical group 0.000 claims 27
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 16
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 14
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 14
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 9
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims 8
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000001041 indolyl group Chemical group 0.000 claims 5
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 230000027928 long-term synaptic potentiation Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Psychiatry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Luminescent Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Claims (12)
1. Spoj formule (I),
[image]
pri čemu
X1 je CH i X2 je N;
R1 je -N(R4)2, ciklopropil, ili R5-piperidin-4-il;
R2 je neovisno D ili halogen;
R3 je naftil, kvinolinil, izokvinolinil, ili indolil, pri čemu su spomenuti naftil, kvinolinil, izokvinolinil ili indolil izborno neovisno supstituirani s barem jednim D, halogenom, (C1-C3)-alkoksi, ili (C1-C3)-alkoksi supstituiranim s barem jednim D;
R4 je neovisno H, (C1-C3)-alkil, (C1-C3)-alkil supstituiran s barem jednim D, (C3-C5)-cikloalkil, ili svaki R4 zajedno s dušikom na kojeg su vezani tvore 3-7 člani heterociklični prsten, pri čemu je jedan od ugljikovih atoma izborno zamijenjen s NR6, O ili S;
R5 je H ili (C1-C3)-alkil, ili (C1-C3)-alkil supstituiran s barem jednim D;
R6 je H, (C1-C3)-alkil, ili (C1-C3)- alkil supstituiran s barem jednim D; i
n je cijeli broj od 0-4; ili njegova farmaceutski prihvatljiva sol,
pri čemu kada R3 je indol-4-il i n je 0, R1 nije N-metil-piperazinil.
2. Spoj prema zahtjevu 1, pri čemu
R3 je naftil, kvinolinil, izokvinolinil, ili indolil, pri čemu su spomenuti naftil, kvinolinil, izokvinolinil ili indolil izborno neovisno supstituirani s barem jednim D, halogenom, (C1-C3)-alkoksi, ili (C1-C3)-alkoksi supstituiranim s barem jednim D; i pri čemu spomenuti indolil nije indol-4-il.
3. Spoj prema zahtjevu 2, pri čemu
R3 je naftil, kvinolinil, izokvinolinil, ili indol-5-il, pri čemu su spomenuti naftil, kvinolinil, izokvinolinil ili indol-5-il izborno neovisno supstituirani s barem jednim D, halogenom, (C1-C3)-alkoksi, ili (C1-C3)-alkoksi supstituiranim s barem jednim D.
4. Spoj prema zahtjevu 3, pri čemu ili
(a)
R3 je naftalen-1-il, naftalen-2-il, kvinolin-8-il, izokvinolin-5-il, ili indol-5-il, pri čemu su spomenuti naftalen-1-il, naftalen-2-il, kvinolin-8-il, izokvinolin-5-il, ili indol-5-il izborno neovisno supstituirani s barem jednim D, halogenom, (C1-C3)-alkoksi, ili (C1-C3)-alkoksi supstituiranim s barem jednim D, ili
(b)
R2 je neovisno halogen;
R3 je naftalen-1-il, naftalen-2-il, kvinolin-8-il, izokvinolin-5-il, ili indol-5-il, pri čemu su spomenuti naftalen-1-il, naftalen-2-il, kvinolin-8-il, izokvinolin-5-il, ili indol-5-il izborno neovisno supstituirani s barem jednim halogenom ili (C1-C3)-alkoksi;
R4 je neovisno H, (C1-C3)-alkil, (C3-C5)-cikloalkil, ili svaki R4 zajedno s dušikom na kojeg su vezani tvore 3-7 člani heterociklični prsten, pri čemu je jedan od ugljikovih atoma izborno zamijenjen s NR6, O ili S;
R5 je H ili (C1-C3)-alkil; i
R6 je H ili (C1-C3)-alkil.
5. Spoj prema zahtjevu 4, pri čemu u (b)
R3 je naftalen-1-il, naftalen-2-il, kvinolin-8-il, ili izokvinolin-5-il, pri čemu su naftalen-1-il, naftalen-2-il, kvinolin-8-il, ili izokvinolin-5-il izborno neovisno supstituirani s barem jednim halogenom ili (C1-C3)-alkoksi;
R4 je neovisno H, (C1-C3)-alkil, (C3-C5)-cikloalkil, ili svaki R4 zajedno s dušikom na kojeg su vezani tvore N-metil piperazin, piperazin, piperidin, pirolidin, azetidin, ili morfolin; i
n je cijeli broj od 0-2, izborno pri čemu
R1 je -N(R4)2 ili ciklopropil;
R2 je fluor;
R3 je naftalen-1-il ili naftalen-2-il;
R4 je neovisno H, (C1-C3)-alkil, (C3-C5)-cikloalkil, ili svaki R4 zajedno s dušikom na kojeg su vezani tvore
[image]
i
n je 0 ili 1.
6. Spoj prema zahtjevu 4, pri čemu u (a)
X1 je CH i X2 je N;
R2 je neovisno halogen;
R3 je naftalen-1-il, naftalen-2-il, kvinolin-8-il, izokvinolin-5-il, ili indol-5-il, pri čemu su spomenuti naftalen-1-il, naftalen-2-il, kvinolin-8-il, izokvinolin-5-il, ili indol-5-il izborno neovisno supstituirani s barem jednim halogenom, ili (C1-C3)-alkoksi;
R4 je neovisno H, (C1-C3)-alkil, (C3-C5)-cikloalkil, ili svaki R4 zajedno s dušikom na kojeg su vezani tvore 3-7 člani heterociklični prsten, pri čemu je jedan od ugljikovih atoma izborno zamijenjen s NR6, O ili S;
R5 je H ili (C1-C3)-alkil; i
R6 je H ili (C1-C3)-alkil.
7. Spoj prema zahtjevu 6, pri čemu
R1 je -N(R4)2 ili ciklopropil;
R2 je neovisno halogen;
R3 je naftalen-1-il, naftalen-2-il, kvinolin-8-il, ili izokvinolin-5-il, pri čemu su naftalen-1-il, naftalen-2-il, kvinolin-8-il, ili izokvinolin-5-il izborno neovisno supstituirani s jednim ili više atoma halogena ili (C1-C3)-alkoksi;
R4 je neovisno H, (C1-C3)-alkil, (C3-C5)-cikloalkil, ili svaki R4 zajedno s dušikom na kojeg su vezani tvore NR6-piperazin, piperidin, pirolidin, azetidin, ili morfolin;
R6 je H, metil ili CD3; i
n je cijeli broj od 0-2, izborno pri čemu
R1 je -N(R4)2 ili ciklopropil;
R2 je neovisno halogen;
R3 je naftalen-1-il, naftalen-2-il, kvinolin-8-il, ili izokvinolin-5-il, pri čemu su naftalen-1-il, naftalen-2-il, kvinolin-8-il, ili izokvinolin-5-il izborno neovisno supstituirani s jednim ili više atoma fluora;
R4 je neovisno H, (C1-C3)-alkil, (C3-C5)-cikloalkil, ili svaki R4 zajedno s dušikom na kojeg su vezani tvore NR6-piperazin, piperidin, pirolidin, azetidin, ili morfolin;
R6 je H, metil ili CD3; i
n je cijeli broj od 0-2, izborno pri čemu
R1 je -N(CH3)2, ciklopropil, ili
[image]
R3 je naftalen-1-il ili naftalen-2-il;
R6 je H, metil ili CD3; i
n je 0, i izborno pri čemu je spoj
[image]
8. Sastav koji sadrži spoj prema bilo kojem od zahtjeva 1-7 i farmaceutski prihvatljivi nosač.
9. Spoj prema bilo kojem od zahtjeva 1-7, ili sastav prema zahtjevu 8, za uporabu u liječenju neurodegenerativne bolesti i/ili ishemije.
10. Spoj ili sastav za uporabu prema zahtjevu 9, pri čemu neurodegenerativna bolest je ALS, Huntingtonova bolest, Parkinsonova bolest ili Alzheimerova bolest.
11. Spoj ili sastav za uporabu prema zahtjevu 9 ili zahtjevu 10, pri čemu primjena spoja ili sastava povećava dugoročnu potencijaciju ili poboljšava pamćenje.
12. Spoj ili sastav za uporabu prema zahtjevu 9 ili zahtjevu 10, pri čemu ishemija je ishemija mozga.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361790207P | 2013-03-15 | 2013-03-15 | |
| EP18215113.4A EP3521284B1 (en) | 2013-03-15 | 2014-03-17 | Pyrazine compounds as map kinase modulators and uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210051T1 true HRP20210051T1 (hr) | 2021-05-14 |
Family
ID=51538480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210051TT HRP20210051T1 (hr) | 2013-03-15 | 2021-01-12 | Spojevi pirazina kao modulatori map kinaze i njihove uporabe |
Country Status (4)
| Country | Link |
|---|---|
| US (4) | US9783525B2 (hr) |
| EP (3) | EP3842424A1 (hr) |
| HR (1) | HRP20210051T1 (hr) |
| WO (1) | WO2014145485A2 (hr) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3842424A1 (en) | 2013-03-15 | 2021-06-30 | The Trustees of Columbia University in the City of New York | Map kinase modulators and uses thereof in the tretament of tauopathies |
| US20160151366A1 (en) * | 2014-11-17 | 2016-06-02 | Vanderbilt University | Compositions and Methods for Treating Autism Spectrum Disorders |
| JP6622822B2 (ja) | 2015-06-23 | 2019-12-18 | ノビリス セラピューティクス インコーポレイテッド | 希ガス組成物を用いた治療的な免疫調節 |
| US9427439B1 (en) | 2015-10-26 | 2016-08-30 | Eip Pharma, Llc | Methods and compositions for recovery from stroke |
| TWI704148B (zh) * | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| SG11202000431PA (en) | 2017-07-18 | 2020-02-27 | Nuvation Bio Inc | 1,8-naphthyridinone compounds and uses thereof |
| WO2019018584A1 (en) | 2017-07-18 | 2019-01-24 | GiraFpharma LLC | HETEROCYCLIC COMPOUNDS AS ADENOSINE ANTAGONISTS |
| US11466008B2 (en) | 2017-09-18 | 2022-10-11 | Eip Pharma, Llc | Co-crystals of neflamapimod (VX-745) |
| CN113924095A (zh) | 2019-01-18 | 2022-01-11 | 诺维逊生物股份有限公司 | 作为腺苷拮抗剂的杂环化合物 |
| EP3911324A4 (en) | 2019-01-18 | 2022-08-17 | Nuvation Bio Inc. | 1,8-NAPHTHYRIDINONE COMPOUNDS AND THEIR USES |
| CN114031558A (zh) * | 2021-12-14 | 2022-02-11 | 无锡捷化医药科技有限公司 | 一种1-(6-氯哒嗪-4-基）乙基-1-酮的制备方法 |
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| US4677620A (en) | 1985-02-28 | 1987-06-30 | Tektronix, Inc. | Graphical input of timing relationships |
| US6093742A (en) | 1997-06-27 | 2000-07-25 | Vertex Pharmaceuticals, Inc. | Inhibitors of p38 |
| US6841567B1 (en) | 1999-02-12 | 2005-01-11 | Cephalon, Inc. | Cyclic substituted fused pyrrolocarbazoles and isoindolones |
| CA2373883A1 (en) | 1999-07-02 | 2001-01-11 | Stuart A. Lipton | Method of reducing neuronal injury or apoptosis |
| DE60120219T2 (de) | 2000-12-21 | 2007-04-12 | Vertex Pharmaceuticals Inc., Cambridge | Pyrazolverbindungen als protein-kinase-inhibitoren |
| EP1470112A1 (en) * | 2002-01-18 | 2004-10-27 | Pharmacia Corporation | Substituted pyridazinones as inhibitors of p38 |
| PA8579601A1 (es) | 2002-08-30 | 2004-05-07 | Pfizer Prod Inc | Compuestos antiinflamatorios de di y trifloruro-triazolo-piridinas |
| EP1606283B1 (en) | 2003-03-03 | 2008-10-08 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| GB0329275D0 (en) | 2003-12-18 | 2004-01-21 | Merck Sharp & Dohme | Therapeutic treatment |
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| CA2589102C (en) | 2004-11-02 | 2013-08-13 | Northwestern University | Pyridazine compounds and methods for using the compounds to treat inflammatory diseases |
| WO2006110588A2 (en) | 2005-04-11 | 2006-10-19 | The Trustees Of Columbia University In The City Of New York | Methods for treating mild cognitive impairment |
| JP2009517390A (ja) | 2005-11-23 | 2009-04-30 | インターミューン インコーポレイテッド | ストレス活性化プロテインキナーゼ系を調節する方法 |
| US8158627B2 (en) | 2006-04-28 | 2012-04-17 | Northwestern University | Compositions and treatments using pyridazine compounds and cholinesterase inhibitors |
| US20080051410A1 (en) | 2006-08-02 | 2008-02-28 | Northwestern University | Protein Kinase Targeted Therapeutics |
| EP2131858A4 (en) | 2007-03-20 | 2011-11-23 | Cadila Pharmaceuticals Ltd | P38 INHIBITORS |
| WO2010074783A1 (en) | 2008-12-23 | 2010-07-01 | The Trustees Of Columbia University In The City Of New York | Phosphodiesterase inhibitors and uses thereof |
| JP6093180B2 (ja) | 2009-12-10 | 2017-03-08 | トラスティーズ・オブ・コロンビア・ユニバーシティ・イン・ザ・シティ・オブ・ニューヨーク | ヒストンアセチルトランスフェラーゼ活性化剤及びその使用 |
| EP3323813B1 (en) | 2010-12-22 | 2020-08-26 | The Trustees of Columbia University in the City of New York | Histone acetyltransferase modulators and uses thereof |
| EP2707369B1 (en) | 2011-05-09 | 2016-07-27 | Eip Pharma, LLC | Compositions and methods for treating alzheimer's disease |
| EP3842424A1 (en) | 2013-03-15 | 2021-06-30 | The Trustees of Columbia University in the City of New York | Map kinase modulators and uses thereof in the tretament of tauopathies |
-
2014
- 2014-03-17 EP EP20211078.9A patent/EP3842424A1/en active Pending
- 2014-03-17 EP EP14762602.2A patent/EP2968322B1/en active Active
- 2014-03-17 EP EP18215113.4A patent/EP3521284B1/en active Active
- 2014-03-17 WO PCT/US2014/030260 patent/WO2014145485A2/en active Application Filing
-
2015
- 2015-09-15 US US14/855,035 patent/US9783525B2/en active Active
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- 2019-08-27 US US16/552,537 patent/US11149020B2/en active Active
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2021
- 2021-01-12 HR HRP20210051TT patent/HRP20210051T1/hr unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2968322A4 (en) | 2016-11-16 |
| US20220009905A1 (en) | 2022-01-13 |
| EP3842424A1 (en) | 2021-06-30 |
| US20160130253A1 (en) | 2016-05-12 |
| US10428047B2 (en) | 2019-10-01 |
| US11566016B2 (en) | 2023-01-31 |
| US11149020B2 (en) | 2021-10-19 |
| US20190389840A1 (en) | 2019-12-26 |
| WO2014145485A2 (en) | 2014-09-18 |
| WO2014145485A3 (en) | 2014-11-27 |
| EP2968322A2 (en) | 2016-01-20 |
| US9783525B2 (en) | 2017-10-10 |
| EP3521284B1 (en) | 2020-12-02 |
| EP2968322B1 (en) | 2018-12-26 |
| US20170369472A1 (en) | 2017-12-28 |
| EP3521284A1 (en) | 2019-08-07 |
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