CA2620534A1 - Imidazo[1,2b]pyridazines substituees constituant des inhibiteurs de kinases, leur production et leur utilisation comme medicaments - Google Patents
Imidazo[1,2b]pyridazines substituees constituant des inhibiteurs de kinases, leur production et leur utilisation comme medicamentsInfo
- Publication number
- CA2620534A1 CA2620534A1 CA002620534A CA2620534A CA2620534A1 CA 2620534 A1 CA2620534 A1 CA 2620534A1 CA 002620534 A CA002620534 A CA 002620534A CA 2620534 A CA2620534 A CA 2620534A CA 2620534 A1 CA2620534 A1 CA 2620534A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridazin
- imidazo
- amine
- alkyl
- heterocycloalkyl
- 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
- 238000002360 preparation method Methods 0.000 title description 7
- 229940043355 kinase inhibitor Drugs 0.000 title description 5
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 5
- 239000003814 drug Substances 0.000 title description 4
- 150000004942 imidazo[1,2-b]pyridazines Chemical class 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 26
- 102000001253 Protein Kinase Human genes 0.000 claims abstract description 15
- 108060006633 protein kinase Proteins 0.000 claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 128
- 229910052757 nitrogen Inorganic materials 0.000 claims description 123
- -1 - OH Chemical group 0.000 claims description 122
- 125000004169 (C1-C6) alkyl group Chemical class 0.000 claims description 117
- 150000001875 compounds Chemical class 0.000 claims description 116
- 125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 108
- 125000001072 heteroaryl group Chemical group 0.000 claims description 92
- 125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 claims description 87
- 125000004191 (C1-C6) alkoxy group Chemical class 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 229910052760 oxygen Inorganic materials 0.000 claims description 70
- 239000001301 oxygen Substances 0.000 claims description 69
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 67
- 125000000171 (C1-C6) haloalkyl group Chemical class 0.000 claims description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 125000004434 sulfur atom Chemical group 0.000 claims description 61
- 125000004737 (C1-C6) haloalkoxy group Chemical class 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 54
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 45
- 108091000080 Phosphotransferase Proteins 0.000 claims description 39
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- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 36
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 208000035475 disorder Diseases 0.000 claims description 34
- 125000004104 aryloxy group Chemical group 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000000882 C2-C6 alkenyl group Chemical class 0.000 claims description 26
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 25
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 21
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 20
- 230000001413 cellular effect Effects 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
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- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 11
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
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- 125000002541 furyl group Chemical class 0.000 claims description 9
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- 125000003226 pyrazolyl group Chemical class 0.000 claims description 9
- 125000004076 pyridyl group Chemical class 0.000 claims description 9
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- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 claims description 8
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- DGYQCUKDGTYYSH-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-n-(2-morpholin-4-ylethyl)imidazo[1,2-b]pyridazin-6-amine Chemical compound C1=NN(C)C=C1C1=CN=C2N1N=C(NCCN1CCOCC1)C=C2 DGYQCUKDGTYYSH-UHFFFAOYSA-N 0.000 claims description 2
- IBELUIICIYWCAD-UHFFFAOYSA-N 4-(3-phenylimidazo[1,2-b]pyridazin-6-yl)pentane-1,4-diamine Chemical compound C1(=CC=CC=C1)C1=CN=C2N1N=C(C=C2)C(CCCN)(C)N IBELUIICIYWCAD-UHFFFAOYSA-N 0.000 claims description 2
- XLYVQTFRSSMSAK-UHFFFAOYSA-N 4-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)pentane-1,4-diamine Chemical compound N12N=C(C(N)(CCCN)C)C=CC2=NC=C1C=1C=CSC=1 XLYVQTFRSSMSAK-UHFFFAOYSA-N 0.000 claims description 2
- 102100034111 Activin receptor type-1 Human genes 0.000 claims description 2
- BUCYNLUNAWUYRD-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CN=C2N1N=C(C=C2)NCC=2C=NC=CC2.CN2N=CC(=C2)C2=CN=C1N2N=C(C=C1)NCC=1C=NC=CC1 Chemical compound C1(=CC=CC=C1)C1=CN=C2N1N=C(C=C2)NCC=2C=NC=CC2.CN2N=CC(=C2)C2=CN=C1N2N=C(C=C1)NCC=1C=NC=CC1 BUCYNLUNAWUYRD-UHFFFAOYSA-N 0.000 claims description 2
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- GNFMXHSIEYENAE-UHFFFAOYSA-N n-(2-morpholin-4-ylethyl)-3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-amine Chemical compound C1=CC2=NC=C(C3=CSC=C3)N2N=C1NCCN1CCOCC1 GNFMXHSIEYENAE-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Immunology (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Emergency Medicine (AREA)
- Transplantation (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102005042742A DE102005042742A1 (de) | 2005-09-02 | 2005-09-02 | Substituierte Imidazo[1,2b]pyridazine als Kinase-Inhibitoren, deren Herstellung und Verwendung als Arzneimittel |
DE102005042742.1 | 2005-09-02 | ||
PCT/DE2006/001564 WO2007025540A2 (fr) | 2005-09-02 | 2006-09-01 | Imidazo[1,2b]pyridazines substituees constituant des inhibiteurs de kinases, leur production et leur utilisation comme medicaments |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2620534A1 true CA2620534A1 (fr) | 2007-03-08 |
CA2620534C CA2620534C (fr) | 2014-05-27 |
Family
ID=37709434
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2620534A Expired - Fee Related CA2620534C (fr) | 2005-09-02 | 2006-09-01 | Imidazo[1,2b]pyridazines substituees constituant des inhibiteurs de kinases, leur production et leur utilisation comme medicaments |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP2176266A2 (fr) |
JP (1) | JP5680824B2 (fr) |
CA (1) | CA2620534C (fr) |
DE (1) | DE102005042742A1 (fr) |
WO (1) | WO2007025540A2 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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AU2012325911B2 (en) * | 2011-10-20 | 2016-06-09 | Glaxosmithkline Llc | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
US9499547B2 (en) | 2011-09-06 | 2016-11-22 | Bayer Intellectual Property Gmbh | Amino-substituted imidazopyridazines |
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US7884109B2 (en) | 2005-04-05 | 2011-02-08 | Wyeth Llc | Purine and imidazopyridine derivatives for immunosuppression |
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US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
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PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
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US20110021513A1 (en) * | 2006-09-07 | 2011-01-27 | Biogen Idec Ma Inc. | Modulators of interleukin-1 receptor-associated kinase |
US7902187B2 (en) | 2006-10-04 | 2011-03-08 | Wyeth Llc | 6-substituted 2-(benzimidazolyl)purine and purinone derivatives for immunosuppression |
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CA2667962A1 (fr) * | 2006-10-30 | 2008-05-08 | Novartis Ag | Composes heterocycliques en tant qu'agents anti-inflammatoires |
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JP6916562B2 (ja) | 2017-08-11 | 2021-08-11 | テリジーン リミテッドTeligene Ltd. | 化合物、その薬学的に許容される塩、溶媒和物、立体異性体及び互変異性体、並びに薬物組成物、過剰増殖性障害治療剤、過剰増殖性障害予防剤、薬物、癌治療剤、癌予防剤、及びキナーゼシグナル伝達調節剤 |
US11236086B2 (en) * | 2017-10-18 | 2022-02-01 | Blueprint Medicines Corporation | Substituted pyrrolopyridines as inhibitors of activin receptor-like kinase |
CN110734437B (zh) * | 2018-07-19 | 2022-04-08 | 南京烁慧医药科技有限公司 | 吡唑并嘧啶化合物和药物组合物及其应用 |
CA3127502A1 (fr) | 2019-02-12 | 2020-08-20 | Sumitomo Dainippon Pharma Oncology, Inc. | Formulations comprenant des inhibiteurs de proteine kinase heterocycliques |
WO2020187291A1 (fr) | 2019-03-19 | 2020-09-24 | 华中师范大学 | Composé de pyrazolopyrimidine, composition pharmaceutique et utilisation associée |
CN111718351B (zh) * | 2019-03-19 | 2021-10-12 | 华中师范大学 | 含氧取代吡唑并嘧啶化合物和药物组合物及其应用 |
CN111718350B (zh) * | 2019-03-19 | 2021-04-13 | 华中师范大学 | 吡唑取代的吡唑并嘧啶化合物和药物组合物及其应用 |
CN111718349B (zh) * | 2019-03-19 | 2021-11-02 | 华中师范大学 | 含氟吡唑并嘧啶化合物和药物组合物及其应用 |
EP3967696A4 (fr) * | 2019-05-08 | 2023-08-09 | TYK Medicines Inc. | Composé utilisé comme inhibiteur de kinase et son application |
CN114437077B (zh) * | 2020-11-04 | 2024-01-30 | 浙江同源康医药股份有限公司 | 用作激酶抑制剂的化合物及其应用 |
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DE3542661A1 (de) * | 1985-12-03 | 1987-06-04 | Bayer Ag | Imidazopyridazinalkensaeureamide, verfahren zu ihrer herstellung, zwischenprodukte zu ihrer herstellung |
AU7079998A (en) * | 1997-04-25 | 1998-11-24 | Takeda Chemical Industries Ltd. | Condensed pyridazine derivatives, their production and use |
SE9800835D0 (sv) * | 1998-03-13 | 1998-03-13 | Astra Ab | New Compounds |
PL354241A1 (en) * | 1999-09-17 | 2003-12-29 | Abbott Gmbh & Co.Kgabbott Gmbh & Co.Kg | Kinase inhibitors as therapeutic agents |
AU3740101A (en) * | 2000-03-01 | 2001-09-12 | Janssen Pharmaceutica Nv | 2,4-disubstituted thiazolyl derivatives |
GB0103926D0 (en) * | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
MXPA05006478A (es) * | 2002-12-18 | 2005-09-08 | Vertex Pharma | Triazolopiridazinas como inhibidores de proteinas cinasas. |
NZ548098A (en) * | 2003-12-31 | 2010-05-28 | Schering Plough Ltd | Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives |
JP2009502734A (ja) * | 2005-07-29 | 2009-01-29 | アステラス製薬株式会社 | Lck阻害剤としての縮合複素環 |
-
2005
- 2005-09-02 DE DE102005042742A patent/DE102005042742A1/de not_active Withdrawn
-
2006
- 2006-09-01 WO PCT/DE2006/001564 patent/WO2007025540A2/fr active Application Filing
- 2006-09-01 JP JP2008528339A patent/JP5680824B2/ja not_active Expired - Fee Related
- 2006-09-01 EP EP06775928A patent/EP2176266A2/fr not_active Withdrawn
- 2006-09-01 CA CA2620534A patent/CA2620534C/fr not_active Expired - Fee Related
Cited By (2)
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US9499547B2 (en) | 2011-09-06 | 2016-11-22 | Bayer Intellectual Property Gmbh | Amino-substituted imidazopyridazines |
AU2012325911B2 (en) * | 2011-10-20 | 2016-06-09 | Glaxosmithkline Llc | Substituted bicyclic aza-heterocycles and analogues as sirtuin modulators |
Also Published As
Publication number | Publication date |
---|---|
JP2009506993A (ja) | 2009-02-19 |
WO2007025540A2 (fr) | 2007-03-08 |
EP2176266A2 (fr) | 2010-04-21 |
CA2620534C (fr) | 2014-05-27 |
DE102005042742A1 (de) | 2007-03-08 |
JP5680824B2 (ja) | 2015-03-04 |
WO2007025540A3 (fr) | 2007-05-18 |
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