NZ739742B2 - Heteroaryl compounds as irak inhibitors and uses thereof - Google Patents
Heteroaryl compounds as irak inhibitors and uses thereofInfo
- Publication number
- NZ739742B2 NZ739742B2 NZ739742A NZ73974216A NZ739742B2 NZ 739742 B2 NZ739742 B2 NZ 739742B2 NZ 739742 A NZ739742 A NZ 739742A NZ 73974216 A NZ73974216 A NZ 73974216A NZ 739742 B2 NZ739742 B2 NZ 739742B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- wkh
- dqg
- zdv
- ehq
- zlwk
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 title 1
- 102000006940 Interleukin-1 Receptor-Associated Kinases Human genes 0.000 abstract 2
- 108010072621 Interleukin-1 Receptor-Associated Kinases Proteins 0.000 abstract 2
- 229940058303 antinematodal Benzimidazole derivatives Drugs 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Classifications
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- A—HUMAN NECESSITIES
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
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- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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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
- C07D471/02—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
- C07D471/08—Bridged systems
Abstract
The present invention relates to benzimidazole derivatives of Formula (I) and pharmaceutically acceptable compositions thereof, useful as interleukin-1 receptor-associated kinase (IRAK) inhibitors.
Description
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ϭ͘ ĐŽŵƉŽƵŶĚ ŽĨ ĨŽƌŵƵůĂ /͕
Žƌ Ă ƉŚĂƌŵĂĐĞƵƚŝĐĂůůLJ ĂĐĐĞƉƚĂďůĞ ƐĂůƚ Ĩ͕ ǁŚĞƌĞŝŶ͗
ŝƐ ƐĞůĞĐƚĞĚ ĨƌŽŵ
ĂŶĚ ͖
ŝƐ Žƌ ͖
Zϯ ŝƐ ʹZ Žƌ ͲŚĂůŽĂůŬLJů͖
Zϰ ŝƐ ʹZ͕ ŚĂůŽŐĞŶ͕ ͲŚĂůŽĂůŬLJů͕ ʹKZ͕ ʹ^Z͕ ʹ E͕ ʹEKϮ͕ Ͳ^KϮZ͕ Ͳ^KZ͕ Ͳ ;KͿZ͕ Ͳ KϮZ͕ Ͳ ;KͿE;ZͿϮ͕ Ͳ
EZ ;KͿZ͕ ͲEZ ;KͿE;ZͿϮ͕ ͲEZ^KϮZ͕ Žƌ ʹE;ZͿϮ͖ ĂŶĚ
ĞĂĐŚ Z ŝƐ ŝŶĚĞƉĞŶĚĞŶƚůLJ ŚLJĚƌŽŐĞŶ͕ ϭʹϲ ĂůŝƉŚĂƚŝĐ͕ ϲʹϭϬ ĂƌLJů͕ Ă ϯͲϴ ĞĚ ƐĂƚƵƌĂƚĞĚ Žƌ ƉĂƌƚŝĂůůLJ
ƵŶƐĂƚƵƌĂƚĞĚ ĐĂƌďŽĐLJĐůŝĐ ƌŝŶŐ͕ Ă ϯͲϳ ĞĚ ŚĞƚĞƌŽĐLJĐůŝĐ ƌŝŶŐ ŚĂǀŝŶŐ ϭͲϰ ŚĞƚĞƌŽĂƚŽŵƐ
ŶĚĞŶƚůLJ ƐĞůĞĐƚĞĚ ĨƌŽŵ ŶŝƚƌŽŐĞŶ͕ ŽdžLJŐĞŶ͕ Žƌ ƐƵůĨƵƌ͕ Žƌ Ă ϱͲϲ ŵĞŵďĞƌĞĚ ĐůŝĐ
ĂƌLJů ƌŝŶŐ ŚĂǀŝŶŐ ϭͲϰ ŚĞƚĞƌŽĂƚŽŵƐ ŝŶĚĞƉĞŶĚĞŶƚůLJ ƐĞůĞĐƚĞĚ ĨƌŽŵ ŶŝƚƌŽŐĞŶ͕ ŽdžLJŐĞŶ͕ Žƌ ƐƵůĨƵƌ͖
ĞĂĐŚ ŽĨ ǁŚŝĐŚ ŝƐ ŽƉƚŝŽŶĂůůLJ ƚƵƚĞĚ͖ Žƌ
ƚǁŽ Z ŐƌŽƵƉƐ ŽŶ ƚŚĞ ƐĂŵĞ ĂƚŽŵ ĂƌĞ ƚĂŬĞŶ ƚŽŐĞƚŚĞƌ ǁŝƚŚ ƚŚĞ ĂƚŽŵ ƚŽ ǁŚŝĐŚ ƚŚĞLJ ĂƌĞ ĂƚƚĂĐŚĞĚ ƚŽ ĨŽƌŵ
Ă ϲʹϭϬ ĂƌLJů͕ Ă ϯͲϴ ŵĞŵďĞƌĞĚ ƐĂƚƵƌĂƚĞĚ Žƌ ƉĂƌƚŝĂůůLJ ƵŶƐĂƚƵƌĂƚĞĚ ĐĂƌďŽĐLJĐůŝĐ ƌŝŶŐ͕ Ă ϯͲϳ ŵĞŵďĞƌĞĚ
ŚĞƚĞƌŽĐLJĐůŝĐ ƌŝŶŐ ŚĂǀŝŶŐ ϭͲϰ ŚĞƚĞƌŽĂƚŽŵƐ ŝŶĚĞƉĞŶĚĞŶƚůLJ ƐĞůĞĐƚĞĚ ĨƌŽŵ ŶŝƚƌŽŐĞŶ͕ ŽdžLJŐĞŶ͕ Žƌ ƐƵůĨƵƌ͕
Žƌ Ă ϱͲϲ ŵĞŵďĞƌĞĚ ŵŽŶŽĐLJĐůŝĐ ŚĞƚĞƌŽĂƌLJů ƌŝŶŐ ŚĂǀŝŶŐ ϭͲϰ ŚĞƚĞƌŽĂƚŽŵƐ ŝŶĚĞƉĞŶĚĞŶƚůLJ ƐĞůĞĐƚĞĚ
ĨƌŽŵ ŶŝƚƌŽŐĞŶ͕ ͕ Žƌ ƐƵůĨƵƌ͖ ĞĂĐŚ ŽĨ ǁŚŝĐŚ ŝƐ ŽƉƚŝŽŶĂůůLJ ƐƵďƐƚŝƚƵƚĞĚ͖ ĂŶĚ
ǁŚĞƌĞŝŶ ͞ŽƉƚŝŽŶĂůůLJ ƐƵďƐƚŝƚƵƚĞĚ͟ ŵĞĂŶƐ ƚŚĂƚ ŐƌŽƵƉƐ ŵĂLJ ďĞ ƐƵďƐƚŝƚƵƚĞĚ ďLJ ŝŶĚĞƉĞŶĚĞŶƚ ƌĞƉůĂĐĞŵĞŶƚ
ŽĨ ŽŶĞ͕ ƚǁŽ͕ Žƌ ƚŚƌĞĞ Žƌ ŵŽƌĞ ŽĨ ƚŚĞ ŚLJĚƌŽŐĞŶ ĂƚŽŵƐ ƚŚĞƌĞŽŶ ďLJ ŽŶĞ Žƌ ŵŽƌĞ ŐƌŽƵƉƐ ƐĞůĞĐƚĞĚ ĨƌŽŵ Ͳ
&͕ Ͳ ů͕ Ͳ ƌ͕ Ͳ/͕ ĚĞƵƚĞƌŝƵŵ͕ ͲK,͕ ĂůŬŽdžLJ͕ ŽdžŽ͕ ͲEKϮ͕ Ͳ E͕ &ϯ͕ ͲE,Ϯ͕ ͲE, ĂůŬLJů͕ ͲE, ĂůŬĞŶLJů͕ ͲE, ĂůŬLJŶLJů͕ Ͳ
E, ĐLJĐůŽĂůŬLJů͕ ͲE, ͲĂƌLJů͕ ͲE, ͲŚĞƚĞƌŽĂƌLJů͕ ͲE, ͲŚĞƚĞƌŽĐLJĐůŝĐ͕ ͲĚŝĂůŬLJůĂŵŝŶŽ͕ ͲĚŝĂƌLJůĂŵŝŶŽ͕ Ͳ
ĚŝŚĞƚĞƌŽĂƌLJůĂŵŝŶŽ͕ ͲKͲ ĂůŬLJů͕ ͲK ĂůŬĞŶLJů͕ ͲKͲĂůŬLJŶLJů͕ ͲKͲ ĐLJĐůŽĂůŬLJů͕ ͲKͲĂƌLJů͕ ĞƌŽĂƌLJů͕ ͲKͲ
ŚĞƚĞƌŽĐLJĐůŝĐ͕ Ͳ ;KͿͲĂůŬLJů͕ Ͳ ;KͿͲĂůŬĞŶLJů͕ Ͳ ;KͿͲĂůŬLJŶLJů͕ Ͳ ;KͿͲĐĂƌďŽĐLJĐůLJů͕ Ͳ ;KͿͲĂƌLJů͕ Ͳ ;KͿͲŚĞƚĞƌŽĂƌLJů͕ Ͳ
ƚĞƌŽĐLJĐůLJů͕ Ͳ KE,Ϯ͕ Ͳ KE,Ͳ ĂůŬLJů͕ Ͳ KE,Ͳ ĂůŬĞŶLJů͕ Ͳ KE,Ͳ ĂůŬLJŶLJů͕ Ͳ KE,ͲĐĂƌďŽĐLJĐůLJů͕ Ͳ KE,Ͳ
ĂƌLJů͕ Ͳ KE,ͲŚĞƚĞƌŽĂƌLJů͕ Ͳ KE,ͲŚĞƚĞƌŽĐLJĐůLJů͕ ͲE, ;KͿͲĂůŬLJů͕ ͲE, ;KͿͲĂůŬĞŶLJů͕ ͲE, ;KͿͲĂůŬLJŶLJů͕ Ͳ
E, ;KͿͲ ĐĂƌďŽĐLJĐůLJů͕ ͲE, ;KͿͲĂƌLJů͕ ͲE, ;KͿͲŚĞƚĞƌŽĂƌLJů͕ ͲE, ;KͿͲŚĞƚĞƌŽĐLJĐůLJů͕ Ͳ ,ϮE,Ϯ͕ Ͳ ,Ϯ^KϮ ,ϯ͕ Ͳ
ĂůŬLJů͕ ͲĂůŬĞŶLJů͕ ͲĂůŬLJŶLJů͕ ͲĂƌLJů͕ ͲĂƌLJůĂůŬLJů͕ ͲŚĞƚĞƌŽĂƌLJů͕ ͲŚĞƚĞƌŽĂƌLJůĂůŬLJů͕ ͲŚĞƚĞƌŽĐLJĐůŽĂůŬLJů͕ ͲĐLJĐůŽĂůŬLJů͕ Ͳ
ĐĂƌďŽĐLJĐůŝĐ͕ ͲŚĞƚĞƌŽĐLJĐůŝĐ͕ ͲŵĞƚŚŽdžLJŵĞƚŚŽdžLJ͕ ĂŶĚ ͲŵĞƚŚŽdžLJĞƚŚŽdžLJ
Ϯ͘ dŚĞ ĐŽŵƉŽƵŶĚ ŽĨ ĐůĂŝŵ ϭ͕ ǁŚĞƌĞŝŶ Zϯ ŝƐ ϭʹϲ ĂůŝƉŚĂƚŝĐ͕ Ă ϯͲϴ ŵĞŵďĞƌĞĚ ƐĂƚƵƌĂƚĞĚ Žƌ ƉĂƌƚŝĂůůLJ
ƵŶƐĂƚƵƌĂƚĞĚ ĐĂƌďŽĐLJĐůŝĐ ƌŝŶŐ͕ Žƌ Ă ϯͲϳ ĞĚ ŚĞƚĞƌŽĐLJĐůŝĐ ƌŝŶŐ ŚĂǀŝŶŐ ϭͲϰ ŚĞƚĞƌŽĂƚŽŵƐ
ŝŶĚĞƉĞŶĚĞŶƚůLJ ƐĞůĞĐƚĞĚ ĨƌŽŵ ŶŝƚƌŽŐĞŶ͕ ŽdžLJŐĞŶ͕ Žƌ ƐƵůĨƵƌ͖ ĞĂĐŚ ŽĨ ǁŚŝĐŚ ŝƐ ŽƉƚŝŽŶĂůůLJ ƐƵďƐƚŝƚƵƚĞĚ͘
ϯ͘ dŚĞ ĐŽŵƉŽƵŶĚ ŽĨ ĐůĂŝŵ Ϯ͕ ǁŚĞƌĞŝŶ Zϯ ŝƐ ŵĞƚŚLJů͕ ĞƚŚLJů͕ ƉƌŽƉLJů͕ ŝͲƉƌŽƉLJů͕ ŶͲďƵƚLJů͕ ƐͲďƵƚLJů͕ ƚͲďƵƚLJů͕
Ă ƐƚƌĂŝŐŚƚ ĐŚĂŝŶ Žƌ ďƌĂŶĐŚĞĚ ƉĞŶƚLJů͕ Žƌ Ă ƐƚƌĂŝŐŚƚ ĐŚĂŝŶ Žƌ ďƌĂŶĐŚĞĚ ŚĞdžLJů͖ ĞĂĐŚ ŽĨ ǁŚŝĐŚ ŝƐ ŽƉƚŝŽŶĂůůLJ
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ĂŶĚ ͘
ϱ͘ dŚĞ ŶĚ ŽĨ ĐůĂŝŵ ϭ͕ ƐĞůĞĐƚĞĚ ĨƌŽŵ
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Žƌ Ă ƉŚĂƌŵĂĐĞƵƚŝĐĂůůLJ ĂďůĞ ƐĂůƚ Ĩ͘
ϲ͘ ƉŚĂƌŵĂĐĞƵƚŝĐĂů ĐŽŵƉŽƐŝƚŝŽŶ ĐŽŵƉƌŝƐŝŶŐ Ă ĐŽŵƉŽƵŶĚ ŽĨ ĐůĂŝŵ ϭ Žƌ Ă ƉŚĂƌŵĂĐĞƵƚŝĐĂůůLJ
ĂĐĐĞƉƚĂďůĞ ƐĂůƚ ƚŚĞƌĞŽĨ͕ ĂŶĚ Ă ƉŚĂƌŵĂĐĞƵƚŝĐĂůůLJ ĂĐĐĞƉƚĂďůĞ ĂĚũƵǀĂŶƚ͕ ĐĂƌƌŝĞƌ͕ Žƌ ǀĞŚŝĐůĞ͘
ϳ͘ hƐĞ ŽĨ Ă ĐŽŵƉŽƵŶĚ ĂĐĐŽƌĚŝŶŐ ƚŽ ĂŶLJŽŶĞ ŽĨ ĐůĂŝŵƐ ϭͲϱ͕ Žƌ Ă ƉŚĂƌŵĂĐĞƵƚŝĐĂůůLJ ĂĐĐĞƉƚĂďůĞ ƐĂůƚ
ƚŚĞƌĞŽĨ͕ ŝŶ ƚŚĞ ĐƚƵƌĞ ŽĨ Ă ŵĞĚŝĐĂŵĞŶƚ ĨŽƌ ƚƌĞĂƚŝŶŐ ĂŶ /Z <ͲŵĞĚŝĂƚĞĚ ĚŝƐŽƌĚĞƌ͘
ϴ͘ dŚĞ ƵƐĞ ŽĨ ĐůĂŝŵ ϳ͕ ǁŚĞƌĞŝŶ ƚŚĞ ĚŝƐŽƌĚĞƌ ŝƐ ĞĚ ĨƌŽŵ ZŚĞƵŵĂƚŽŝĚ ƌƚŚƌŝƚŝƐ͕ WƐŽƌŝĂƚŝĐ
ƚŝƐ͕ KƐƚĞŽĂƌƚŚƌŝƚŝƐ͕ ^LJƐƚĞŵŝĐ >ƵƉƵƐ ƌLJƚŚĞŵĂƚŽƐƵƐ͕ >ƵƉƵƐ ƚŝƐ͕ ŶŬLJůŽƐŝŶŐ ^ƉŽŶĚLJůŝƚŝƐ͕
KƐƚĞŽƉŽƌŽƐŝƐ͕ ŝĐ ƐĐůĞƌŽƐŝƐ͕ DƵůƚŝƉůĞ ^ĐůĞƌŽƐŝƐ͕ WƐŽƌŝĂƐŝƐ͕ dLJƉĞ / ĚŝĂďĞƚĞƐ͕ dLJƉĞ // ĚŝĂďĞƚĞƐ͕
/ŶĨůĂŵŵĂƚŽƌLJ ŽǁĞů ŝƐĞĂƐĞ ; ƌŽŶŚ͛Ɛ ŝƐĞĂƐĞ ĂŶĚ hůĐĞƌĂƚŝǀĞ ŽůŝƚŝƐͿ͕ ,LJƉĞƌŝŵŵƵŶŽŐůŽďƵůŝŶĞŵŝĂ
ĂŶĚ ƉĞƌŝŽĚŝĐ ĨĞǀĞƌ ƐLJŶĚƌŽŵĞ͕ ƌLJŽƉLJƌŝŶͲĂƐƐŽĐŝĂƚĞĚ ƉĞƌŝŽĚŝĐ ƐLJŶĚƌŽŵĞƐ͕ ^ĐŚŶŝƚnjůĞƌΖƐ ƐLJŶĚƌŽŵĞ͕
^LJƐƚĞŵŝĐ ũƵǀĞŶŝůĞ ŝĚŝŽƉĂƚŚŝĐ ĂƌƚŚƌŝƚŝƐ͕ ĚƵůƚΖƐ ŽŶƐĞƚ ^ƚŝůůΖƐ ĚŝƐĞĂƐĞ͕ 'ŽƵƚ͕ WƐĞƵĚŽŐŽƵƚ͕ ^ W,K
ƐLJŶĚƌŽŵĞ͕ ĂƐƚůĞŵĂŶΖƐ ĚŝƐĞĂƐĞ͕ ͕ ^ƚƌŽŬĞ͕ ƚŚĞƌŽƐĐůĞƌŽƐŝƐ͕ ĞůŝĂĐ ĚŝƐĞĂƐĞ͕ /Z ; ĞĨŝĐŝĞŶĐLJ ŽĨ
/>Ͳϭ ZĞĐĞƉƚŽƌ ŶƚĂŐŽŶŝƐƚͿ͕ ůnjŚĞŝŵĞƌ͛Ɛ ĚŝƐĞĂƐĞ͕ WĂƌŬŝŶƐŽŶ͛Ɛ Ğ͕ ĂŶĚ ĂŶĐĞƌ͘
ϵ͘ dŚĞ ƵƐĞ ŽĨ ĐůĂŝŵ ϴ͕ ǁŚĞƌĞŝŶ ƚŚĞ ĚŝƐŽƌĚĞƌ ŝƐ ƐĞůĞĐƚĞĚ ĨƌŽŵ ZŚĞƵŵĂƚŽŝĚ ƌƚŚƌŝƚŝƐ͕ ^LJƐƚĞŵŝĐ
>ƵƉƵƐ ƌLJƚŚĞŵĂƚŽƐƵƐ͕ >ƵƉƵƐ ŶĞƉŚƌŝƚŝƐ͕ ĂŶĚ DƵůƚŝƉůĞ ^ĐůĞƌŽƐŝƐ͘
ϭϬ͘ ĐŽŵƉŽƵŶĚ ĂĐĐŽƌĚŝŶŐ ƚŽ ĐůĂŝŵ ϭ ƐƵďƐƚĂŶƚŝĂůůLJ ĂƐ ŚĞƌĞŝŶ ĚĞƐĐƌŝďĞĚ Žƌ ĞdžĞŵƉůŝĨŝĞĚ͘
ϭϭ͘ ƉŚĂƌŵĂĐĞƵƚŝĐĂů ĐŽŵƉŽƐŝƚŝŽŶ ĂĐĐŽƌĚŝŶŐ ƚŽ ĐůĂŝŵ ϲ ƐƵďƐƚĂŶƚŝĂůůLJ ĂƐ ŚĞƌĞŝŶ ĚĞƐĐƌŝďĞĚ Žƌ
ĞdžĞŵƉůŝĨŝĞĚ͘
ϭϮ͘ ƵƐĞ ĂĐĐŽƌĚŝŶŐ ƚŽ ĐůĂŝŵ ϳ ƐƵďƐƚĂŶƚŝĂůůLJ ĂƐ ŚĞƌĞŝŶ ďĞĚ Žƌ ĞdžĞŵƉůŝĨŝĞĚ͘
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562220358P | 2015-09-18 | 2015-09-18 | |
| US62/220,358 | 2015-09-18 | ||
| PCT/US2016/052107 WO2017049069A1 (en) | 2015-09-18 | 2016-09-16 | Heteroaryl compounds as irak inhibitors and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ739742A NZ739742A (en) | 2022-03-25 |
| NZ739742B2 true NZ739742B2 (en) | 2022-06-28 |
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