JP2010523668A5 - - Google Patents
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- Publication number
- JP2010523668A5 JP2010523668A5 JP2010503041A JP2010503041A JP2010523668A5 JP 2010523668 A5 JP2010523668 A5 JP 2010523668A5 JP 2010503041 A JP2010503041 A JP 2010503041A JP 2010503041 A JP2010503041 A JP 2010503041A JP 2010523668 A5 JP2010523668 A5 JP 2010523668A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- pyrazolo
- ylmethyl
- pyridine
- adamantan
- 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.)
- Pending
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- -1 cyano, amino Chemical group 0.000 claims description 131
- 208000002193 Pain Diseases 0.000 claims description 40
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 208000004296 neuralgia Diseases 0.000 claims description 18
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 206010029240 Neuritis Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 6
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 210000005036 nerve Anatomy 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- 201000001119 neuropathy Diseases 0.000 claims description 5
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical compound O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 238000001356 surgical procedure Methods 0.000 claims description 3
- 150000003536 tetrazoles Chemical group 0.000 claims description 3
- 208000004998 Abdominal Pain Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 2
- 206010072005 Spinal pain Diseases 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 230000001684 chronic effect Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 208000014674 injury Diseases 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- 230000008764 nerve damage Effects 0.000 claims description 2
- 201000009985 neuronitis Diseases 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 230000008653 root damage Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- JTKOPFYDSWAYOU-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-4-carboxamide Chemical compound NC(=O)C1=CC=CN2N=CC=C12 JTKOPFYDSWAYOU-UHFFFAOYSA-N 0.000 claims 8
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 7
- 102000005962 receptors Human genes 0.000 claims 6
- 108020003175 receptors Proteins 0.000 claims 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 5
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 4
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- QPLANJREYKBWPK-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound N1=C(C=C2N1C=CC=C2C(=O)N)C(=O)N QPLANJREYKBWPK-UHFFFAOYSA-N 0.000 claims 4
- 125000003003 spiro group Chemical group 0.000 claims 4
- 125000002837 carbocyclic group Chemical group 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 208000008035 Back Pain Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000000839 emulsion Substances 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 239000000843 powder Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 claims 1
- SBEYSORPLCAQTE-UHFFFAOYSA-N 2-(4-cyanophenyl)-n-[(1-pyridin-3-ylcyclohexyl)methyl]indolizine-8-carboxamide Chemical compound C=1C=CN2C=C(C=3C=CC(=CC=3)C#N)C=C2C=1C(=O)NCC1(C=2C=NC=CC=2)CCCCC1 SBEYSORPLCAQTE-UHFFFAOYSA-N 0.000 claims 1
- QVPDWYITOFRENT-UHFFFAOYSA-N 2-[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]-3-phenylpropanoic acid Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(C(=O)O)CC1=CC=CC=C1 QVPDWYITOFRENT-UHFFFAOYSA-N 0.000 claims 1
- YUIHGRMJYBFGDF-UHFFFAOYSA-N 2-[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]acetic acid Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(CC(=O)O)=N2 YUIHGRMJYBFGDF-UHFFFAOYSA-N 0.000 claims 1
- UERXTKPJCZRCLJ-UHFFFAOYSA-N 2-[4-[[1-(4-chlorophenyl)cyclohexyl]methylcarbamoyl]pyrazolo[1,5-a]pyridin-2-yl]-3-phenylpropanoic acid Chemical compound C1=C2C(C(=O)NCC3(CCCCC3)C=3C=CC(Cl)=CC=3)=CC=CN2N=C1C(C(=O)O)CC1=CC=CC=C1 UERXTKPJCZRCLJ-UHFFFAOYSA-N 0.000 claims 1
- OVERMEQXACQAMN-UHFFFAOYSA-N 2-[[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]methoxy]acetic acid Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(COCC(=O)O)=N2 OVERMEQXACQAMN-UHFFFAOYSA-N 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GVKOSRMDVRPKDI-UHFFFAOYSA-N 2-n-(2-fluoroethyl)-2-n-methyl-4-n-[4-methyl-2-[4-(trifluoromethyl)phenyl]pentyl]pyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C=1C=CN2N=C(C(=O)N(C)CCF)C=C2C=1C(=O)NCC(CC(C)C)C1=CC=C(C(F)(F)F)C=C1 GVKOSRMDVRPKDI-UHFFFAOYSA-N 0.000 claims 1
- CPFVPCFIEGUMKE-UHFFFAOYSA-N 3-[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]-3-phenylpropanoic acid Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(CC(=O)O)C1=CC=CC=C1 CPFVPCFIEGUMKE-UHFFFAOYSA-N 0.000 claims 1
- IHDPSHPBSKAZMG-UHFFFAOYSA-N 3-[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]-4-phenylbutanoic acid Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(CC(=O)O)CC1=CC=CC=C1 IHDPSHPBSKAZMG-UHFFFAOYSA-N 0.000 claims 1
- YHUVSEBRYYJVPU-UHFFFAOYSA-N 3-[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]butanoic acid Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(C(CC(O)=O)C)=N2 YHUVSEBRYYJVPU-UHFFFAOYSA-N 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- KLOXQPJMPFEMRI-UHFFFAOYSA-N 4-[8-(1-adamantylmethylcarbamoyl)indolizin-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CN2C=CC=C(C(=O)NCC34CC5CC(CC(C5)C3)C4)C2=C1 KLOXQPJMPFEMRI-UHFFFAOYSA-N 0.000 claims 1
- OTYRUBULVUCRRY-UHFFFAOYSA-N 4-[[2-(1-adamantyl)acetyl]amino]-n-(2-fluoroethyl)-n-methylpyrazolo[1,5-a]pyridine-2-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CN2C1=CC(C(=O)N(CCF)C)=N2 OTYRUBULVUCRRY-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- TWNVBWKQZQUFIY-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-(2,2-difluoroethyl)-2-n-methylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(C(=O)N(CC(F)F)C)=N2 TWNVBWKQZQUFIY-UHFFFAOYSA-N 0.000 claims 1
- WBDMGAIUPYOVOC-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-(2-fluoroethyl)-2-n-methylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(C(=O)N(CCF)C)=N2 WBDMGAIUPYOVOC-UHFFFAOYSA-N 0.000 claims 1
- RZLWDWCWBJFUJH-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-(2-methoxyethyl)-2-n-methylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(C(=O)N(C)CCOC)=N2 RZLWDWCWBJFUJH-UHFFFAOYSA-N 0.000 claims 1
- YWPZSCFOAAFRAM-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-[(2-fluorophenyl)methyl]-2-n-methylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(=O)N(C)CC1=CC=CC=C1F YWPZSCFOAAFRAM-UHFFFAOYSA-N 0.000 claims 1
- IBXGUPZDCYHJTL-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-[(3-fluorophenyl)methyl]-2-n-methylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(=O)N(C)CC1=CC=CC(F)=C1 IBXGUPZDCYHJTL-UHFFFAOYSA-N 0.000 claims 1
- SWYLYYMKAYSRJI-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-[(4-fluorophenyl)methyl]-2-n-methylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(=O)N(C)CC1=CC=C(F)C=C1 SWYLYYMKAYSRJI-UHFFFAOYSA-N 0.000 claims 1
- GACVSPFNSLISBV-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-methyl-2-n-pyridin-2-ylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(=O)N(C)C1=CC=CC=N1 GACVSPFNSLISBV-UHFFFAOYSA-N 0.000 claims 1
- QVFZQFKUDMCGRG-UHFFFAOYSA-N 4-n-(1-adamantylmethyl)-2-n-methyl-2-n-pyridin-4-ylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C1=C2C(C(=O)NCC34CC5CC(CC(C5)C3)C4)=CC=CN2N=C1C(=O)N(C)C1=CC=NC=C1 QVFZQFKUDMCGRG-UHFFFAOYSA-N 0.000 claims 1
- IZLWAUQRDGJXQJ-UHFFFAOYSA-N 4-n-[[1-(4-chlorophenyl)cyclohexyl]methyl]-2-n-(2-fluoroethyl)-2-n-methylpyrazolo[1,5-a]pyridine-2,4-dicarboxamide Chemical compound C=1C=CN2N=C(C(=O)N(CCF)C)C=C2C=1C(=O)NCC1(C=2C=CC(Cl)=CC=2)CCCCC1 IZLWAUQRDGJXQJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010058019 Cancer Pain Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000002881 Colic Diseases 0.000 claims 1
- 206010014020 Ear pain Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Chemical group 0.000 claims 1
- 206010015958 Eye pain Diseases 0.000 claims 1
- 206010016059 Facial pain Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010023230 Joint stiffness Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000000112 Myalgia Diseases 0.000 claims 1
- AOPGBEZKFDWGPK-UHFFFAOYSA-N N1=C(C=C2N1C=CC=C2C(=O)N)C(=O)NCC(F)F Chemical compound N1=C(C=C2N1C=CC=C2C(=O)N)C(=O)NCC(F)F AOPGBEZKFDWGPK-UHFFFAOYSA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010049002 Scar pain Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 206010042496 Sunburn Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 230000008484 agonism Effects 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 230000008485 antagonism Effects 0.000 claims 1
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- 229940125810 compound 20 Drugs 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 201000006549 dyspepsia Diseases 0.000 claims 1
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- FSGIYBOKACTVIV-UHFFFAOYSA-N ethyl 2-[[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]methoxy]acetate Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(COCC(=O)OCC)=N2 FSGIYBOKACTVIV-UHFFFAOYSA-N 0.000 claims 1
- RMBQMOYUPDNESA-UHFFFAOYSA-N ethyl 2-[[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridin-2-yl]methyl-methylamino]acetate Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(CN(C)CC(=O)OCC)=N2 RMBQMOYUPDNESA-UHFFFAOYSA-N 0.000 claims 1
- PENCNLSXVHSZQT-UHFFFAOYSA-N ethyl 2-[[4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridine-2-carbonyl]-methylamino]acetate Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(C(=O)N(C)CC(=O)OCC)=N2 PENCNLSXVHSZQT-UHFFFAOYSA-N 0.000 claims 1
- KRIVZXKVQHPSBY-UHFFFAOYSA-N ethyl 4-(1-adamantylmethylcarbamoyl)pyrazolo[1,5-a]pyridine-2-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13CNC(=O)C1=CC=CN2C1=CC(C(=O)OCC)=N2 KRIVZXKVQHPSBY-UHFFFAOYSA-N 0.000 claims 1
- OGVPLGLVEMXWKC-UHFFFAOYSA-N ethyl 4-[[2-(1-adamantyl)acetyl]amino]pyrazolo[1,5-a]pyridine-2-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CN2C1=CC(C(=O)OCC)=N2 OGVPLGLVEMXWKC-UHFFFAOYSA-N 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
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- 239000006260 foam Substances 0.000 claims 1
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- 208000033065 inborn errors of immunity Diseases 0.000 claims 1
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- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
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| KR102232744B1 (ko) | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
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| KR102222220B1 (ko) | 2013-01-22 | 2021-03-03 | 이도르시아 파마슈티컬스 리미티드 | Ｐ2ｘ7 수용체 길항제로서의 헤테로시클릭 아미드 유도체 |
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2008
- 2008-04-09 BR BRPI0809567-1A patent/BRPI0809567A2/pt not_active IP Right Cessation
- 2008-04-09 MY MYPI20094173A patent/MY148461A/en unknown
- 2008-04-09 CA CA002682925A patent/CA2682925A1/en not_active Abandoned
- 2008-04-09 MX MX2009010523A patent/MX2009010523A/es active IP Right Grant
- 2008-04-09 CN CN200880019683A patent/CN101772498A/zh active Pending
- 2008-04-09 JP JP2010503041A patent/JP2010523668A/ja active Pending
- 2008-04-09 EP EP08742668A patent/EP2155744A1/en not_active Withdrawn
- 2008-04-09 EP EP13154412.4A patent/EP2592082A1/en not_active Withdrawn
- 2008-04-09 AU AU2008236649A patent/AU2008236649B2/en not_active Ceased
- 2008-04-09 KR KR1020097023254A patent/KR20090130109A/ko not_active Ceased
- 2008-04-09 EA EA200970931A patent/EA200970931A1/ru unknown
- 2008-04-09 US US12/595,394 patent/US8580812B2/en not_active Expired - Fee Related
- 2008-04-09 NZ NZ580394A patent/NZ580394A/en not_active IP Right Cessation
- 2008-04-09 CN CN2013101274201A patent/CN103204852A/zh active Pending
- 2008-04-09 UA UAA200910331A patent/UA99610C2/ru unknown
- 2008-04-09 WO PCT/US2008/004563 patent/WO2008124153A1/en not_active Ceased
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2009
- 2009-10-01 IL IL201356A patent/IL201356A0/en unknown
- 2009-11-10 CO CO09127786A patent/CO6241110A2/es not_active Application Discontinuation
-
2013
- 2013-10-02 US US14/043,861 patent/US20140038955A1/en not_active Abandoned
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