TW200843757A - Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors - Google Patents

Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors Download PDF

Info

Publication number: TW200843757A
Authority: TW; Taiwan
Prior art keywords: alkyl; compound; mmol; formula; group
Prior art date: 2007-03-28

Application number

TW097111546A

Other languages

English (en)

Chinese (zh)

Inventor

Fredrik P Marmsater

Mark C Munson

James P Rizzi

John E Robinson

Stephen T Schlachter

George T Topalov

Qian Zhao

Joseph P Lyssikatos

Original Assignee

Array Biopharma Inc

Priority date (The priority date 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 date listed.)

2007-03-28

Filing date

2008-03-28

Publication date

2008-11-16

2008-03-28 Application filed by Array Biopharma Inc filed Critical Array Biopharma Inc

2008-11-16 Publication of TW200843757A publication Critical patent/TW200843757A/zh

Links

229940127361 Receptor Tyrosine Kinase Inhibitors Drugs 0.000 title description 2
150000005234 imidazo[1,2-a]pyridines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 154
230000001404 mediated effect Effects 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims description 222
-1 C(0)NHMe Chemical compound 0.000 claims description 155
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 120
238000000034 method Methods 0.000 claims description 51
150000003839 salts Chemical class 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
125000000753 cycloalkyl group Chemical group 0.000 claims description 26
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000004076 pyridyl group Chemical group 0.000 claims description 23
229910052731 fluorine Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
150000002923 oximes Chemical class 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
229910003827 NRaRb Inorganic materials 0.000 claims description 15
206010028980 Neoplasm Diseases 0.000 claims description 15
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
125000004429 atom Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
229910052763 palladium Inorganic materials 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 10
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
229910052707 ruthenium Inorganic materials 0.000 claims description 9
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 8
208000024891 symptom Diseases 0.000 claims description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
201000011510 cancer Diseases 0.000 claims description 7
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000003446 ligand Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000003554 tetrahydropyrrolyl group Chemical group 0.000 claims description 7
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 6
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
125000000468 ketone group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 5
125000003709 fluoroalkyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
238000005859 coupling reaction Methods 0.000 claims description 4
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
230000009615 deamination Effects 0.000 claims 1
238000006481 deamination reaction Methods 0.000 claims 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
239000000835 fiber Substances 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
239000003112 inhibitor Substances 0.000 abstract description 15
108091008598 receptor tyrosine kinases Proteins 0.000 abstract description 15
102000027426 receptor tyrosine kinases Human genes 0.000 abstract description 15
201000010099 disease Diseases 0.000 abstract description 14
102000005962 receptors Human genes 0.000 abstract description 6
108020003175 receptors Proteins 0.000 abstract description 6
101001001642 Xenopus laevis Serine/threonine-protein kinase pim-3 Proteins 0.000 abstract description 5
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 abstract 1
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238000006243 chemical reaction Methods 0.000 description 220
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238000002360 preparation method Methods 0.000 description 182
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201000006417 multiple sclerosis Diseases 0.000 description 106
239000007787 solid Substances 0.000 description 82
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239000000243 solution Substances 0.000 description 76
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 73
239000011541 reaction mixture Substances 0.000 description 69
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
239000000047 product Substances 0.000 description 50
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 42
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 41
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 39
239000002585 base Substances 0.000 description 39
239000010410 layer Substances 0.000 description 39
238000010992 reflux Methods 0.000 description 39
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 35
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
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238000003818 flash chromatography Methods 0.000 description 23
239000010948 rhodium Substances 0.000 description 23
239000002253 acid Substances 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 21
229910052786 argon Inorganic materials 0.000 description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 19
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
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210000004027 cell Anatomy 0.000 description 17
150000004032 porphyrins Chemical class 0.000 description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 16
150000001412 amines Chemical class 0.000 description 16
229910052805 deuterium Inorganic materials 0.000 description 16
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 15
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Classifications

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- C07—ORGANIC CHEMISTRY
- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
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- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
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General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Immunology (AREA)
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Hematology (AREA)
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Rheumatology (AREA)
Neurology (AREA)
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Obesity (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Oncology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

TW097111546A 2007-03-28 2008-03-28 Imidazo[1,2-a]pyridine compounds as receptor tyrosine kinase inhibitors TW200843757A (en)

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US90855607P	2007-03-28	2007-03-28

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US (1)	US20100144751A1 (2)
EP (1)	EP2139888A2 (2)
JP (1)	JP2010522765A (2)
CN (1)	CN101679422A (2)
CA (1)	CA2682231A1 (2)
TW (1)	TW200843757A (2)
WO (1)	WO2008121687A2 (2)

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NZ580327A (en) *	2007-04-03	2012-02-24	Array Biopharma Inc	IMIDAZO[1,2-a]PYRIDINE COMPOUNDS AS RECEPTOR TYROSINE KINASE INHIBITORS
JP5244917B2 (ja)	2007-11-30	2013-07-24	ノバルティスアーゲー	Ｃ２−ｃ５−アルキル−イミダゾール−ビスホスホネート類
US8895550B2 (en)	2008-08-19	2014-11-25	Array Biopharma Inc.	Triazolopyridine compounds as PIM kinase inhibitors
US8557809B2 (en)	2008-08-19	2013-10-15	Array Biopharma Inc.	Triazolopyridine compounds as PIM kinase inhibitors
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- 2008-03-27 CA CA002682231A patent/CA2682231A1/en not_active Abandoned
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Publication number	Publication date
EP2139888A2 (en)	2010-01-06
CN101679422A (zh)	2010-03-24
JP2010522765A (ja)	2010-07-08
US20100144751A1 (en)	2010-06-10
CA2682231A1 (en)	2008-10-09
WO2008121687A2 (en)	2008-10-09
WO2008121687A3 (en)	2008-11-20

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