JP2010520875A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010520875A5 JP2010520875A5 JP2009552762A JP2009552762A JP2010520875A5 JP 2010520875 A5 JP2010520875 A5 JP 2010520875A5 JP 2009552762 A JP2009552762 A JP 2009552762A JP 2009552762 A JP2009552762 A JP 2009552762A JP 2010520875 A5 JP2010520875 A5 JP 2010520875A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- oxo
- hydroxy
- dihydro
- ethyl
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 97
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000001475 halogen functional group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 208000035475 disorder Diseases 0.000 claims description 21
- 208000004296 neuralgia Diseases 0.000 claims description 21
- 208000002193 Pain Diseases 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 16
- 230000001404 mediated effect Effects 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- -1 hydroxy, amino Chemical group 0.000 claims description 14
- 208000037765 diseases and disorders Diseases 0.000 claims description 12
- 208000003251 Pruritus Diseases 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 208000023504 respiratory system disease Diseases 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 7
- 208000021722 neuropathic pain Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 206010043269 Tension headache Diseases 0.000 claims description 6
- 208000008548 Tension-Type Headache Diseases 0.000 claims description 6
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 208000004371 toothache Diseases 0.000 claims description 6
- 230000009529 traumatic brain injury Effects 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 206010069632 Bladder dysfunction Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 208000006561 Cluster Headache Diseases 0.000 claims description 5
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 208000034347 Faecal incontinence Diseases 0.000 claims description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
- 208000014540 Functional gastrointestinal disease Diseases 0.000 claims description 5
- 206010019233 Headaches Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 206010065390 Inflammatory pain Diseases 0.000 claims description 5
- 206010026749 Mania Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 206010046851 Uveitis Diseases 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 208000005298 acute pain Diseases 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 201000010105 allergic rhinitis Diseases 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 230000036772 blood pressure Effects 0.000 claims description 5
- 201000007637 bowel dysfunction Diseases 0.000 claims description 5
- 208000018912 cluster headache syndrome Diseases 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- 206010014599 encephalitis Diseases 0.000 claims description 5
- 231100000869 headache Toxicity 0.000 claims description 5
- 230000009610 hypersensitivity Effects 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 230000007803 itching Effects 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 230000027939 micturition Effects 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 208000010125 myocardial infarction Diseases 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 210000002307 prostate Anatomy 0.000 claims description 5
- 230000000241 respiratory effect Effects 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 208000019116 sleep disease Diseases 0.000 claims description 5
- 208000020431 spinal cord injury Diseases 0.000 claims description 5
- VAGQFUYFCXXJAL-LYTYMJBXSA-N (2r)-2-[5-[[2-(1-adamantyl)acetyl]amino]-6-chloro-1-oxoisoquinolin-2-yl]propanamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CN([C@@H](C(N)=O)C)C(=O)C2=CC=C1Cl VAGQFUYFCXXJAL-LYTYMJBXSA-N 0.000 claims description 4
- VIFCIENBDYQQDX-LLVKDONJSA-N (2r)-2-[6-chloro-1-oxo-5-[[2-[4-(trifluoromethyl)phenyl]acetyl]amino]isoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 VIFCIENBDYQQDX-LLVKDONJSA-N 0.000 claims description 4
- OPGCMPGPBPRTCR-SNVBAGLBSA-N (2r)-2-[6-chloro-5-[[2-(4-chloro-2-fluorophenyl)acetyl]amino]-1-oxoisoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C=C1F OPGCMPGPBPRTCR-SNVBAGLBSA-N 0.000 claims description 4
- MZMRGDSURPETPD-SNVBAGLBSA-N (2r)-2-[6-chloro-5-[[2-[2-fluoro-3-(trifluoromethyl)phenyl]acetyl]amino]-1-oxoisoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F MZMRGDSURPETPD-SNVBAGLBSA-N 0.000 claims description 4
- KGUURNWYZWNORB-GFCCVEGCSA-N (2r)-2-[6-methoxy-1-oxo-5-[[2-[4-(trifluoromethyl)phenyl]acetyl]amino]isoquinolin-2-yl]propanamide Chemical compound COC1=CC=C(C(N([C@H](C)C(N)=O)C=C2)=O)C2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 KGUURNWYZWNORB-GFCCVEGCSA-N 0.000 claims description 4
- VIFCIENBDYQQDX-NSHDSACASA-N (2s)-2-[6-chloro-1-oxo-5-[[2-[4-(trifluoromethyl)phenyl]acetyl]amino]isoquinolin-2-yl]propanamide Chemical compound ClC1=CC=C2C(=O)N([C@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 VIFCIENBDYQQDX-NSHDSACASA-N 0.000 claims description 4
- WKSFDYRQJMJNFR-NWDGAFQWSA-N (2s)-n-[2-[(2r)-1-amino-1-oxopropan-2-yl]-6-chloro-1-oxoisoquinolin-5-yl]-2-(4-chlorophenyl)propanamide Chemical compound C1([C@@H](C(=O)NC=2C3=C(C(N([C@H](C)C(N)=O)C=C3)=O)C=CC=2Cl)C)=CC=C(Cl)C=C1 WKSFDYRQJMJNFR-NWDGAFQWSA-N 0.000 claims description 4
- UFSZNGPKJWFSHR-CYBMUJFWSA-N 2-(4-chloro-3-fluorophenyl)-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 UFSZNGPKJWFSHR-CYBMUJFWSA-N 0.000 claims description 4
- NNKBOZOTRMTPFO-LLVKDONJSA-N 2-(4-chloro-3-fluorophenyl)-n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(F)=C1 NNKBOZOTRMTPFO-LLVKDONJSA-N 0.000 claims description 4
- OHYAXGAMZSGPOJ-UHFFFAOYSA-N 2-[2-fluoro-3-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-(2-hydroxyethylamino)-1-oxoisoquinolin-5-yl]acetamide Chemical compound OCCNC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F OHYAXGAMZSGPOJ-UHFFFAOYSA-N 0.000 claims description 4
- LKZDPAFXWXYVCK-UHFFFAOYSA-N 2-[2-fluoro-3-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F LKZDPAFXWXYVCK-UHFFFAOYSA-N 0.000 claims description 4
- VSGLANORJMNZRC-CYBMUJFWSA-N 2-[2-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F VSGLANORJMNZRC-CYBMUJFWSA-N 0.000 claims description 4
- BDROBZBNYQZUKM-GFCCVEGCSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methoxy-1-oxoisoquinolin-5-yl]acetamide Chemical compound COC1=CC=C(C(N([C@H](C)CO)C=C2)=O)C2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 BDROBZBNYQZUKM-GFCCVEGCSA-N 0.000 claims description 4
- JECILOFRRYCNDH-CYBMUJFWSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 JECILOFRRYCNDH-CYBMUJFWSA-N 0.000 claims description 4
- QGYFHOFGDBIVEE-HNNXBMFYSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-1-oxo-2-[(3s)-pyrrolidin-3-yl]isoquinolin-5-yl]acetamide Chemical compound C=1C=C(C(F)(F)F)C(F)=CC=1CC(=O)NC=1C(C)=CC=C(C2=O)C=1C=CN2[C@H]1CCNC1 QGYFHOFGDBIVEE-HNNXBMFYSA-N 0.000 claims description 4
- UTSFTJWRTXSFSI-CYBMUJFWSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 UTSFTJWRTXSFSI-CYBMUJFWSA-N 0.000 claims description 4
- BHWBPMXJZHATJD-HNNXBMFYSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[6-methyl-1-oxo-2-[(3s)-pyrrolidin-3-yl]isoquinolin-5-yl]acetamide Chemical compound C=1C=C(F)C(C(F)(F)F)=CC=1CC(=O)NC=1C(C)=CC=C(C2=O)C=1C=CN2[C@H]1CCNC1 BHWBPMXJZHATJD-HNNXBMFYSA-N 0.000 claims description 4
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 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 description 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 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- AFSOBVSIITWGAF-CQSZACIVSA-N n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]-2-[4-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1 AFSOBVSIITWGAF-CQSZACIVSA-N 0.000 claims description 4
- IZEFXOBBYMQCBC-UHFFFAOYSA-N n-[6-chloro-2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]-2-(3,4-dichlorophenyl)acetamide Chemical compound ClC1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(Cl)=C1 IZEFXOBBYMQCBC-UHFFFAOYSA-N 0.000 claims description 4
- XJRFFZIYWHIBPY-UHFFFAOYSA-N n-[6-chloro-2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]-2-[2-fluoro-3-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1F XJRFFZIYWHIBPY-UHFFFAOYSA-N 0.000 claims description 4
- ZXOKHTSAKAOOLZ-UHFFFAOYSA-N n-[6-chloro-2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 ZXOKHTSAKAOOLZ-UHFFFAOYSA-N 0.000 claims description 4
- CUGAKOQXTULJDP-UHFFFAOYSA-N n-[6-chloro-2-(2-hydroxyethyl)-1-oxoisoquinolin-5-yl]-2-[4-fluoro-3-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N(CCO)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 CUGAKOQXTULJDP-UHFFFAOYSA-N 0.000 claims description 4
- OTKCYGCETOSQLA-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-(3,4-dichlorophenyl)acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(Cl)C(Cl)=C1 OTKCYGCETOSQLA-LLVKDONJSA-N 0.000 claims description 4
- LAUUQYWKAHXBPX-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[2-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C=C1F LAUUQYWKAHXBPX-LLVKDONJSA-N 0.000 claims description 4
- FMOOSLMLRAUSBH-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 FMOOSLMLRAUSBH-LLVKDONJSA-N 0.000 claims description 4
- SOXLIWHVZZQEKK-LLVKDONJSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[4-fluoro-3-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 SOXLIWHVZZQEKK-LLVKDONJSA-N 0.000 claims description 4
- GFMGLRZDRMQUJJ-CYBMUJFWSA-N n-[6-cyclopropyl-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound C1CC1C1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 GFMGLRZDRMQUJJ-CYBMUJFWSA-N 0.000 claims description 4
- 230000003959 neuroinflammation Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- AYLWRSUFLVTPDR-UHFFFAOYSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 AYLWRSUFLVTPDR-UHFFFAOYSA-N 0.000 claims description 3
- 208000018569 Respiratory Tract disease Diseases 0.000 claims description 3
- 208000017169 kidney disease Diseases 0.000 claims description 3
- 201000006370 kidney failure Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 208000036273 reactive airway disease Diseases 0.000 claims description 3
- NPYWIUPZYUTEAK-GFCCVEGCSA-N (2r)-2-[5-[[2-[3-fluoro-4-(trifluoromethyl)phenyl]acetyl]amino]-6-methyl-1-oxoisoquinolin-2-yl]propanamide Chemical compound CC1=CC=C2C(=O)N([C@@H](C(N)=O)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 NPYWIUPZYUTEAK-GFCCVEGCSA-N 0.000 claims description 2
- YMFPTJMPYCNHKO-ASXFNGKXSA-N 2-(1-adamantyl)-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=C2C=CN([C@@H](CO)C)C(=O)C2=CC=C1C YMFPTJMPYCNHKO-ASXFNGKXSA-N 0.000 claims description 2
- IXZKBFCFFLHLOH-CQSZACIVSA-N 2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]isoquinoline-5-carboxamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=CC(C(F)(F)F)=C1 IXZKBFCFFLHLOH-CQSZACIVSA-N 0.000 claims description 2
- GVNUVQYGCQUSSM-OAHLLOKOSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2r)-1-(3-hydroxyazetidin-1-yl)propan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound C([C@@H](C)N1C(C2=CC=C(C)C(NC(=O)CC=3C=C(F)C(=CC=3)C(F)(F)F)=C2C=C1)=O)N1CC(O)C1 GVNUVQYGCQUSSM-OAHLLOKOSA-N 0.000 claims description 2
- JECILOFRRYCNDH-ZDUSSCGKSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[2-[(2s)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 JECILOFRRYCNDH-ZDUSSCGKSA-N 0.000 claims description 2
- FFEPLNNDVFVTTR-QGZVFWFLSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-1-oxo-2-[(2r)-1-piperazin-1-ylpropan-2-yl]isoquinolin-5-yl]acetamide Chemical compound C([C@@H](C)N1C(C2=CC=C(C)C(NC(=O)CC=3C=C(F)C(=CC=3)C(F)(F)F)=C2C=C1)=O)N1CCNCC1 FFEPLNNDVFVTTR-QGZVFWFLSA-N 0.000 claims description 2
- PSTNSIKFKNCGHB-CQSZACIVSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-2-[(2r)-1-(methylamino)propan-2-yl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@H](C)CNC)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 PSTNSIKFKNCGHB-CQSZACIVSA-N 0.000 claims description 2
- CSYHHBNQBKHTNI-UHFFFAOYSA-N 2-[3-fluoro-4-(trifluoromethyl)phenyl]-n-[6-methyl-2-[2-(methylamino)ethyl]-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N(CCNC)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 CSYHHBNQBKHTNI-UHFFFAOYSA-N 0.000 claims description 2
- AAMIKLACARMFCS-UHFFFAOYSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]-n-[2-(2-hydroxyethyl)-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C(C(N(CCO)C=C2)=O)C2=C1NC(=O)CC1=CC=C(F)C(C(F)(F)F)=C1 AAMIKLACARMFCS-UHFFFAOYSA-N 0.000 claims description 2
- ASENOMBGSSJKRC-MRXNPFEDSA-N 2-cycloheptyl-n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1CCCCCC1 ASENOMBGSSJKRC-MRXNPFEDSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- OXONEBANLJOTOC-GFCCVEGCSA-N 6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxo-n-[[2-(trifluoromethyl)phenyl]methyl]isoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=CC=C1C(F)(F)F OXONEBANLJOTOC-GFCCVEGCSA-N 0.000 claims description 2
- GBYDWBHRSCUQEX-GFCCVEGCSA-N 6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxo-n-[[3-(trifluoromethyl)phenyl]methyl]isoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=CC(C(F)(F)F)=C1 GBYDWBHRSCUQEX-GFCCVEGCSA-N 0.000 claims description 2
- AGNFDSPQPAUSFK-LLVKDONJSA-N 6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxo-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]isoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=C(C(F)(F)F)N=C1 AGNFDSPQPAUSFK-LLVKDONJSA-N 0.000 claims description 2
- STCKYUXIYJWHAM-SSDOTTSWSA-N 6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxylic acid Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(O)=O STCKYUXIYJWHAM-SSDOTTSWSA-N 0.000 claims description 2
- YKSYAQQQDHLPJI-CQSZACIVSA-N 6-chloro-n-(cycloheptylmethyl)-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1CCCCCC1 YKSYAQQQDHLPJI-CQSZACIVSA-N 0.000 claims description 2
- BEMQUFQRXPAIGV-CQSZACIVSA-N 6-chloro-n-[(1-hydroxycycloheptyl)methyl]-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1(O)CCCCCC1 BEMQUFQRXPAIGV-CQSZACIVSA-N 0.000 claims description 2
- FHXZVDBITWXWNE-CYBMUJFWSA-N 6-chloro-n-[(1-hydroxycyclohexyl)methyl]-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1(O)CCCCC1 FHXZVDBITWXWNE-CYBMUJFWSA-N 0.000 claims description 2
- GTJKHIXCDWFPNM-ABWNMTHHSA-N 6-chloro-n-[(3-hydroxy-3-bicyclo[2.2.1]heptanyl)methyl]-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1(O)C(C2)CCC2C1 GTJKHIXCDWFPNM-ABWNMTHHSA-N 0.000 claims description 2
- CAEONLAMIOORMA-GFCCVEGCSA-N 6-chloro-n-[(4,4-difluorocyclohexyl)methyl]-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1CCC(F)(F)CC1 CAEONLAMIOORMA-GFCCVEGCSA-N 0.000 claims description 2
- PWBBZHNVXSPICS-LLVKDONJSA-N 6-chloro-n-[(4-chloro-3-fluorophenyl)methyl]-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=C(Cl)C(F)=C1 PWBBZHNVXSPICS-LLVKDONJSA-N 0.000 claims description 2
- VTYGNFUYVGHQRP-LLVKDONJSA-N 6-chloro-n-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinoline-5-carboxamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=C(C(F)(F)F)C(F)=C1 VTYGNFUYVGHQRP-LLVKDONJSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims description 2
- 230000003412 degenerative effect Effects 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims description 2
- TWUJPPOAFORSHG-MRXNPFEDSA-N n-(cycloheptylmethyl)-2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinoline-5-carboxamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1CCCCCC1 TWUJPPOAFORSHG-MRXNPFEDSA-N 0.000 claims description 2
- KXQFFZDKVDPYRZ-MRXNPFEDSA-N n-[(1-hydroxycycloheptyl)methyl]-2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinoline-5-carboxamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1(O)CCCCCC1 KXQFFZDKVDPYRZ-MRXNPFEDSA-N 0.000 claims description 2
- BPPNPDKWLMZXDM-CYBMUJFWSA-N n-[(4-chloro-3-fluorophenyl)methyl]-2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinoline-5-carboxamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=C(Cl)C(F)=C1 BPPNPDKWLMZXDM-CYBMUJFWSA-N 0.000 claims description 2
- DUVRRTNJEKQIPG-UHFFFAOYSA-N n-[2-(1,3-dihydroxypropan-2-yl)-6-methyl-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=C(C(N(C(CO)CO)C=C2)=O)C2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 DUVRRTNJEKQIPG-UHFFFAOYSA-N 0.000 claims description 2
- RKIHNKBYTUYHDG-CYBMUJFWSA-N n-[2-[(2r)-1-aminopropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CN)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 RKIHNKBYTUYHDG-CYBMUJFWSA-N 0.000 claims description 2
- UTMNVXYOFWISHC-CQSZACIVSA-N n-[2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1 UTMNVXYOFWISHC-CQSZACIVSA-N 0.000 claims description 2
- ITLBYFHASKQNFP-GFCCVEGCSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[3-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1=CC=CC(C(F)(F)F)=C1 ITLBYFHASKQNFP-GFCCVEGCSA-N 0.000 claims description 2
- XIGDTHFEXZYBMC-CQSZACIVSA-N n-[6-chloro-2-[(2r)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-cycloheptylacetamide Chemical compound ClC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1NC(=O)CC1CCCCCC1 XIGDTHFEXZYBMC-CQSZACIVSA-N 0.000 claims description 2
- FMOOSLMLRAUSBH-NSHDSACASA-N n-[6-chloro-2-[(2s)-1-hydroxypropan-2-yl]-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide Chemical compound ClC1=CC=C2C(=O)N([C@H](CO)C)C=CC2=C1NC(=O)CC1=CC=C(C(F)(F)F)C(F)=C1 FMOOSLMLRAUSBH-NSHDSACASA-N 0.000 claims description 2
- XOUBDCKHGLMWMZ-CYBMUJFWSA-N n-[[3-fluoro-4-(trifluoromethyl)phenyl]methyl]-2-[(2r)-1-hydroxypropan-2-yl]-6-methyl-1-oxoisoquinoline-5-carboxamide Chemical compound CC1=CC=C2C(=O)N([C@@H](CO)C)C=CC2=C1C(=O)NCC1=CC=C(C(F)(F)F)C(F)=C1 XOUBDCKHGLMWMZ-CYBMUJFWSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 2
- 235000019645 odor Nutrition 0.000 claims 1
- 238000000034 method Methods 0.000 description 16
- 241000124008 Mammalia Species 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 206010029240 Neuritis Diseases 0.000 description 5
- 230000007794 irritation Effects 0.000 description 4
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 206010003399 Arthropod bite Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 208000001387 Causalgia Diseases 0.000 description 1
- 206010008334 Cervicobrachial syndrome Diseases 0.000 description 1
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- 208000021965 Glossopharyngeal Nerve disease Diseases 0.000 description 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 206010049949 Intercostal neuralgia Diseases 0.000 description 1
- 208000007914 Labor Pain Diseases 0.000 description 1
- 208000035945 Labour pain Diseases 0.000 description 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 1
- 208000002472 Morton Neuroma Diseases 0.000 description 1
- 208000020059 Morton neuralgia Diseases 0.000 description 1
- 206010068106 Occipital neuralgia Diseases 0.000 description 1
- 102100037602 P2X purinoceptor 7 Human genes 0.000 description 1
- 101710189965 P2X purinoceptor 7 Proteins 0.000 description 1
- 208000004983 Phantom Limb Diseases 0.000 description 1
- 206010056238 Phantom pain Diseases 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 208000003589 Spider Bites Diseases 0.000 description 1
- 206010053509 Venomous bite Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 229960002504 capsaicin Drugs 0.000 description 1
- 235000017663 capsaicin Nutrition 0.000 description 1
- 230000035606 childbirth Effects 0.000 description 1
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 201000005442 glossopharyngeal neuralgia Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 201000009985 neuronitis Diseases 0.000 description 1
- 210000003254 palate Anatomy 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 208000019629 polyneuritis Diseases 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000003491 tear gas Substances 0.000 description 1
- 210000001738 temporomandibular joint Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90604907P | 2007-03-09 | 2007-03-09 | |
| US91826107P | 2007-03-15 | 2007-03-15 | |
| US91826007P | 2007-03-15 | 2007-03-15 | |
| US91812307P | 2007-03-15 | 2007-03-15 | |
| US91808607P | 2007-03-15 | 2007-03-15 | |
| US837007P | 2007-12-20 | 2007-12-20 | |
| US838607P | 2007-12-20 | 2007-12-20 | |
| US838507P | 2007-12-20 | 2007-12-20 | |
| US1067208P | 2008-01-10 | 2008-01-10 | |
| PCT/US2008/003175 WO2008112205A1 (en) | 2007-03-09 | 2008-03-07 | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010520875A JP2010520875A (ja) | 2010-06-17 |
| JP2010520875A5 true JP2010520875A5 (https=) | 2011-03-31 |
Family
ID=39759833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009552762A Pending JP2010520875A (ja) | 2007-03-09 | 2008-03-07 | Ｐ２ｘ７調節因子としてのビシクロヘテロアリール化合物およびその使用 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8093265B2 (https=) |
| EP (1) | EP2124562B1 (https=) |
| JP (1) | JP2010520875A (https=) |
| CN (1) | CN101686680B (https=) |
| CA (1) | CA2680275C (https=) |
| DK (1) | DK2124562T3 (https=) |
| ES (1) | ES2576643T3 (https=) |
| WO (1) | WO2008112205A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2001474T3 (en) | 2006-03-16 | 2016-05-09 | Second Genome Inc | BICYCLOHETEROARYL COMPOUNDS AS P2X7 MODULATORS AND APPLICATIONS THEREOF |
| CA2645551C (en) * | 2006-03-16 | 2016-06-28 | Renovis, Inc. | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof |
| TWI464148B (zh) * | 2006-03-16 | 2014-12-11 | Evotec Us Inc | 作為ｐ２ｘ7調節劑之雙環雜芳基化合物與其用途 |
| MX2009000117A (es) * | 2006-07-06 | 2009-01-23 | Glaxo Group Ltd | N-fenilmetil-5-oxo-prolin-2-amidas sustituidas como antagonistas de receptores p2x7 y sus metodos de uso. |
| US8212723B2 (en) * | 2008-08-27 | 2012-07-03 | Qualcomm Incorporated | Method and apparatus for determining at a predetermined granularity the direction and range of a transmitting mobile device |
| CN103687860B (zh) * | 2011-07-22 | 2016-06-08 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
| US9409917B2 (en) | 2012-01-20 | 2016-08-09 | Actelion Pharmaceuticals Ltd. | Heterocyclic amide derivatives as P2X7 receptor antagonists |
| WO2014091415A1 (en) | 2012-12-12 | 2014-06-19 | Actelion Pharmaceuticals Ltd | Indole carboxamide derivatives as p2x7 receptor antagonists |
| KR102232744B1 (ko) | 2012-12-18 | 2021-03-26 | 이도르시아 파마슈티컬스 리미티드 | Ｐ２ｘ７ 수용체 길항제로서의 인돌 카르복사미드 유도체 |
| ES2616883T3 (es) | 2013-01-22 | 2017-06-14 | Actelion Pharmaceuticals Ltd. | Derivados amida heterocíclicos como antagonistas del receptor P2X7 |
| CA2896790C (en) | 2013-01-22 | 2022-05-10 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
| CN106573907B (zh) * | 2014-06-05 | 2020-09-08 | 默克专利有限公司 | 喹啉衍生物及其用于神经退化性疾病的用途 |
| TWI825637B (zh) | 2021-03-31 | 2023-12-11 | 美商輝瑞股份有限公司 | 啶－１，６（２ｈ，７ｈ）－二酮 |
| CN121843919A (zh) * | 2023-09-13 | 2026-04-10 | 苏文生命科学有限公司 | 作为p2x7受体拮抗剂的n-芳基苯甲酰胺衍生物 |
Family Cites Families (105)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US588736A (en) * | 1897-08-24 | Egg-tester | ||
| FR2450E (fr) | 1903-02-09 | 1904-04-07 | Sulzer Freres Soc | Palier pour pompes et autres machines analogues |
| DE2343984A1 (de) | 1973-08-31 | 1975-03-13 | Hoechst Ag | Wasserunloesliche disazomethinfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| US3950343A (en) * | 1973-11-06 | 1976-04-13 | Ayerst, Mckenna And Harrison Ltd. | Pyrroloisoquinoline derivatives |
| US3900477A (en) * | 1973-11-06 | 1975-08-19 | Ayerst Mckenna & Harrison | 5-amino-and 5-hydrazinodihydropyrroloisoquinoline derivatives |
| SU749832A1 (ru) | 1978-03-24 | 1980-07-23 | Предприятие П/Я М-5885 | Способ получени амино- -оксифенантридонов |
| GB2044254B (en) | 1979-01-26 | 1983-01-26 | Wyeth John & Brother Ltd | Piperidine derivatives |
| EP0093488A3 (en) | 1982-03-18 | 1984-05-23 | Beecham Group Plc | Nortropyl benzopyrrolinone compounds, process for their preparation and pharmaceutical compositions containing them |
| EP0095262B1 (en) | 1982-05-11 | 1986-12-03 | Beecham Group Plc | Azabicycloalkane derivatives, their preparation and medicaments containing them |
| EP0101641A3 (en) | 1982-07-22 | 1984-03-28 | Beecham Group Plc | Sulfonylamino-aza-bicyclo-alkyl derivatives |
| JPH0731405B2 (ja) | 1986-05-02 | 1995-04-10 | キヤノン株式会社 | 電子写真感光体 |
| JP2699511B2 (ja) | 1988-01-29 | 1998-01-19 | 武田薬品工業株式会社 | 置換アミン類 |
| US4897391A (en) * | 1988-06-17 | 1990-01-30 | Schering Corporation | Tricyclic anti-allergy, antiinflammatory and anti-hyperproliferative compounds |
| US5776963A (en) | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| GB8926560D0 (en) | 1989-11-24 | 1990-01-17 | Zambeletti Spa L | Pharmaceuticals |
| US5140023A (en) | 1990-04-27 | 1992-08-18 | G. D. Searle & Co. | Azatetracycle compounds |
| HU213136B (en) | 1990-08-14 | 1997-02-28 | Kyorin Seiyaku Kk | Process for producing fluoroethyl camptothecin derivatives and pharmaceutical compositions containing them |
| KR920008026A (ko) | 1990-10-24 | 1992-05-27 | 오노 화아마슈티칼 캄파니 리미팃드 | 이소퀴놀리논 유도체 또는 이의 무독성 산부가염 또는 이의 수화물, 이의 제조방법 및 이를 포함하는 약제 조성물 |
| JPH04270273A (ja) | 1991-02-25 | 1992-09-25 | Kyorin Pharmaceut Co Ltd | チアゾリジン−２，４−ジオン誘導体とその塩及びその製造法 |
| EP0502575A1 (en) | 1991-03-06 | 1992-09-09 | Merck & Co. Inc. | Substituted 1-(2H)-isoquinolinones |
| WO1992018115A1 (en) | 1991-04-18 | 1992-10-29 | Dr Lo Zambeletti S.P.A. | Use of heterocyclic compounds for the treatment of inflammatory pain |
| US5491148A (en) * | 1991-04-26 | 1996-02-13 | Syntex (U.S.A.) Inc. | Isoquinolinone and dihydroisoquinolinone 5-HT3 receptor antagonists |
| US5246948A (en) | 1991-05-10 | 1993-09-21 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| GB9122859D0 (en) | 1991-10-28 | 1991-12-11 | Smithkline Beecham Plc | Novel compounds |
| US5272158A (en) | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| JPH06295078A (ja) | 1992-04-24 | 1994-10-21 | Canon Inc | 電子写真感光体、該電子写真感光体を備えた電子写真装置並びにファクシミリ |
| US5840903A (en) | 1992-07-27 | 1998-11-24 | G. D. Searle & Co. | 4-aminomethyl-1-azaadamantane derived benzamides |
| US5354757A (en) | 1992-12-15 | 1994-10-11 | G. D. Searle & Co. | Azanoradamantanes |
| WO1994029273A1 (en) | 1993-06-09 | 1994-12-22 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| DE4333761A1 (de) | 1993-10-04 | 1995-04-06 | Luitpold Pharma Gmbh | Heterocyclische Carbamate, Verfahren zu ihrer Herstellung und Arzneimittel |
| US5716993A (en) | 1993-12-27 | 1998-02-10 | Eisai Co., Ltd. | Anthranilic acid derivatives |
| US5530018A (en) | 1994-02-04 | 1996-06-25 | G. D. Searle & Co. | Meso-azanoradamantanes |
| GB9409150D0 (en) | 1994-05-09 | 1994-06-29 | Black James Foundation | Cck and gastrin receptor ligands |
| US5500442A (en) | 1994-06-10 | 1996-03-19 | American Home Products Corporation | Cyclobut-3-ene-1,2-dione derivatives as smooth muscle relaxants |
| US5644144A (en) * | 1994-09-23 | 1997-07-01 | Advanced Micro Devices, Inc. | Device and method for programming a logic level within an integrated circuit using multiple mask layers |
| US5631280A (en) | 1995-03-29 | 1997-05-20 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| CA2225255A1 (en) | 1995-06-29 | 1997-01-16 | Merck & Co., Inc. | Combinations of inhibitors of farnesyl-protein transferase |
| US5723411A (en) * | 1995-10-31 | 1998-03-03 | E. I. Du Pont De Nemours And Company | Herbicidal pyridazinones |
| JP3285746B2 (ja) * | 1995-11-24 | 2002-05-27 | 株式会社資生堂 | フェニレンジアミン誘導体及びラジカルスカベンジャー、脳梗塞抑制剤、脳浮腫抑制剤 |
| US5756518A (en) | 1996-04-02 | 1998-05-26 | Kowa Co., Ltd. | Phenylene derivatives |
| WO1997047601A1 (en) | 1996-06-11 | 1997-12-18 | Yoshitomi Pharmaceutical Industries, Ltd. | Fused heterocyclic compounds and medicinal uses thereof |
| NZ333904A (en) | 1996-07-25 | 2000-06-23 | Biogen Inc | VLA-4 and IIb/IIIa cell adhesion inhibitors |
| US6429212B1 (en) | 1996-08-16 | 2002-08-06 | Ishihara Sangyo Kaisha Ltd. | Medicinal composition |
| DE19650975A1 (de) | 1996-12-09 | 1998-06-10 | Basf Ag | Neue heterocyclisch substituierte Benzamide und deren Anwendung |
| DE19653645A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| DE19653647A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| US6262068B1 (en) * | 1997-02-21 | 2001-07-17 | Bristol-Myers Squibb Company | Lactam derivatives as antiarrhythmic agents |
| PT877019E (pt) | 1997-05-09 | 2002-05-31 | Hoechst Ag | Acidos diaminocarboxilicos substituidos |
| TW544448B (en) | 1997-07-11 | 2003-08-01 | Novartis Ag | Pyridine derivatives |
| PT1023291E (pt) * | 1997-10-07 | 2004-09-30 | Ortho Mcneil Pharm Inc | Derivados de dipiridoimidazole uteis no tratamento de desordens do sistema nervoso central |
| EP1025087A1 (en) | 1997-10-24 | 2000-08-09 | Smithkline Beecham Plc | Substituted isoquinoline derivatives and their use as anticonvulsants |
| JP3337992B2 (ja) * | 1997-11-04 | 2002-10-28 | ファイザー製薬株式会社 | ５−置換ピコリン酸化合物及びその製造方法 |
| SE9704546D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| JPH11171774A (ja) | 1997-12-05 | 1999-06-29 | Kyowa Hakko Kogyo Co Ltd | 血球増多剤 |
| SE9704544D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| SE9704545D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
| EP1051403A1 (en) | 1998-01-29 | 2000-11-15 | Dr. Reddy's Research Foundation | Novel alkanoic acids and their use in medicine, process for their preparation and pharmaceutical compositions containing them |
| AU9298798A (en) | 1998-05-15 | 1999-12-06 | Guilford Pharmaceuticals Inc. | Fused tricyclic compounds which inhibit parp activity |
| GB9817424D0 (en) * | 1998-08-11 | 1998-10-07 | Smithkline Beecham Plc | Novel compounds |
| SE9901875D0 (sv) | 1999-05-25 | 1999-05-25 | Astra Pharma Prod | Novel compounds |
| GB9915995D0 (en) | 1999-07-09 | 1999-09-08 | Ahmed S | Non-steroidal sulphamate compounds for use as oestrone sulphatase inhibitors |
| ATE380176T1 (de) | 1999-08-04 | 2007-12-15 | Icagen Inc | Benzanilide als öffner des kaliumkanals |
| EP1200086A4 (en) | 1999-08-04 | 2009-05-27 | Icagen Inc | THERAPEUTIC OR PROPHYLACTIC METHODS OF PAIN AND ANXIETY |
| GB9919411D0 (en) | 1999-08-18 | 1999-10-20 | Zeneca Ltd | Chemical compounds |
| AU7314200A (en) | 1999-09-17 | 2001-04-24 | Yamanouchi Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| SE9904652D0 (sv) * | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
| JP2001172258A (ja) | 1999-12-17 | 2001-06-26 | Sumitomo Pharmaceut Co Ltd | 神経網膜変性疾患の治療薬 |
| CA2397575A1 (en) | 2000-01-13 | 2001-07-19 | Tularik Inc. | Antibacterial agents |
| GB0005366D0 (en) * | 2000-03-06 | 2000-04-26 | Xenova Ltd | Pharmaceutical compounds |
| WO2001072712A1 (en) | 2000-03-24 | 2001-10-04 | Cor Therapeutics, Inc. | ISOQUINOLONE INHIBITORS OF FACTOR Xa |
| US6545011B2 (en) | 2000-07-13 | 2003-04-08 | Guilford Pharmaceuticals Inc. | Substituted 4,9-dihydrocyclopenta[imn]phenanthridine-5-ones, derivatives thereof and their uses |
| US6603013B2 (en) * | 2000-07-17 | 2003-08-05 | Merck & Co., Inc. | Heterogeneously catalyzed process for cross coupling alkenyl halides with boronic acids |
| US20040122223A1 (en) | 2001-02-07 | 2004-06-24 | Davis Jeremy Martin | Non-natural nucleotides and dinucleotides |
| JP2002338837A (ja) | 2001-05-16 | 2002-11-27 | Fuji Photo Film Co Ltd | 新規化合物、色素、インク組成物、インクジェット用インク、インクジェット記録方法、及び熱転写色素 |
| EP1396488A1 (en) | 2001-05-23 | 2004-03-10 | Mitsubishi Pharma Corporation | Fused heterocyclic compound and medicinal use thereof |
| EP1414443B1 (en) | 2001-08-01 | 2006-11-15 | Merck & Co., Inc. | BENZIMIDAZO 4,5-f|ISOQUINOLINONE DERIVATIVES |
| CA2476936A1 (en) | 2002-02-20 | 2003-08-28 | Chih-Hung Lee | Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (vr1) receptor |
| US7074805B2 (en) * | 2002-02-20 | 2006-07-11 | Abbott Laboratories | Fused azabicyclic compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor |
| GB0206876D0 (en) | 2002-03-22 | 2002-05-01 | Merck Sharp & Dohme | Therapeutic agents |
| CA2480468C (en) | 2002-03-26 | 2012-03-13 | Biofrontera Discovery Gmbh | Fredericamycin derivatives |
| DE10215316C1 (de) | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
| US20060079503A1 (en) | 2002-05-03 | 2006-04-13 | Schering Aktiengesellschaft | Thiazolidinones and the use therof as polo-like kinase inhibitors |
| EP1541559A4 (en) | 2002-07-22 | 2007-08-22 | Asahi Kasei Pharma Corp | 5-SUBSTITUTED ISOQUINOLINE DERIVATIVE |
| DE10238865A1 (de) | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| JP2004203813A (ja) | 2002-12-26 | 2004-07-22 | Tokuyama Corp | クロメン化合物 |
| PA8591801A1 (es) * | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
| KR101076018B1 (ko) | 2003-01-08 | 2011-10-21 | 유니버시티 오브 워싱톤 | 항균제 |
| TW200503994A (en) | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| US20040192728A1 (en) | 2003-02-03 | 2004-09-30 | Ellen Codd | Quinoline-derived amide modulators of vanilloid VR1 receptor |
| AU2004234087A1 (en) | 2003-04-28 | 2004-11-11 | Tibotec Pharmaceuticals Ltd. | HIV integrase inhibitors |
| ATE355273T1 (de) * | 2003-05-12 | 2006-03-15 | Pfizer Prod Inc | Benzamidinhibitoren des p2x7-rezeptors |
| CN1566099A (zh) | 2003-06-13 | 2005-01-19 | 中国科学院上海药物研究所 | 异喹啉－1,3,4－三酮类化合物、制备方法及其用途 |
| WO2004113345A1 (ja) | 2003-06-20 | 2004-12-29 | Japan Tobacco Inc. | 縮合ピロール化合物及びその医薬用途 |
| US7390820B2 (en) * | 2003-08-25 | 2008-06-24 | Amgen Inc. | Substituted quinolinone derivatives and methods of use |
| MXPA06003951A (es) * | 2003-10-07 | 2006-06-27 | Renovis Inc | Derivados de amida como ligandos del canal de ion y composiciones farmaceuticas y sus metodos de uso. |
| US7491794B2 (en) * | 2003-10-14 | 2009-02-17 | Intermune, Inc. | Macrocyclic compounds as inhibitors of viral replication |
| TW200530235A (en) * | 2003-12-24 | 2005-09-16 | Renovis Inc | Bicycloheteroarylamine compounds as ion channel ligands and uses thereof |
| JP2005232175A (ja) | 2004-01-21 | 2005-09-02 | Asahi Kasei Pharma Kk | ５−置換イソキノリン医薬 |
| CA2553968A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments of inflammatory and neuropathic pain |
| US7576099B2 (en) * | 2005-02-28 | 2009-08-18 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
| US7402596B2 (en) * | 2005-03-24 | 2008-07-22 | Renovis, Inc. | Bicycloheteroaryl compounds as P2X7 modulators and uses thereof |
| TWI464148B (zh) * | 2006-03-16 | 2014-12-11 | Evotec Us Inc | 作為ｐ２ｘ7調節劑之雙環雜芳基化合物與其用途 |
| DK2001474T3 (en) * | 2006-03-16 | 2016-05-09 | Second Genome Inc | BICYCLOHETEROARYL COMPOUNDS AS P2X7 MODULATORS AND APPLICATIONS THEREOF |
| CA2645551C (en) * | 2006-03-16 | 2016-06-28 | Renovis, Inc. | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof |
| CA2645652A1 (en) * | 2006-03-16 | 2007-09-27 | Renovis, Inc. | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof |
-
2008
- 2008-03-07 JP JP2009552762A patent/JP2010520875A/ja active Pending
- 2008-03-07 WO PCT/US2008/003175 patent/WO2008112205A1/en not_active Ceased
- 2008-03-07 ES ES08726672.2T patent/ES2576643T3/es active Active
- 2008-03-07 US US12/075,111 patent/US8093265B2/en not_active Expired - Fee Related
- 2008-03-07 CA CA2680275A patent/CA2680275C/en not_active Expired - Fee Related
- 2008-03-07 DK DK08726672.2T patent/DK2124562T3/en active
- 2008-03-07 EP EP08726672.2A patent/EP2124562B1/en not_active Not-in-force
- 2008-03-07 CN CN200880014110.6A patent/CN101686680B/zh active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010520875A5 (https=) | ||
| JP2009530304A5 (https=) | ||
| JP2008534511A5 (https=) | ||
| JP2009541206A5 (https=) | ||
| JP2009530302A5 (https=) | ||
| CA2680275C (en) | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof | |
| DK1933622T3 (en) | Bicycloheteroarylforbindelser som P2X7-modulatorer og anvendelser deraf | |
| JP5306987B2 (ja) | Ｐ２ｘ７調節因子としてのビシクロへテロアリール化合物およびその使用 | |
| JP2010524930A5 (https=) | ||
| JP2008534511A (ja) | Ｐ２ｘ７調節因子としてのビシクロヘテロアリール化合物およびその使用 | |
| US20100184802A1 (en) | Bicycloheteroaryl Compounds as P2X7 Modulators and Uses Thereof | |
| WO2007109154A2 (en) | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof | |
| WO2007109182A2 (en) | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof | |
| JP2010526069A5 (https=) | ||
| PT2007752E (pt) | Benzoimidazol-2-il pirimidinas e pirazinas como moduladores do receptor de histamina h4 | |
| EP1937643A2 (en) | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof | |
| JP2019532054A5 (https=) | ||
| JP2011503072A5 (https=) | ||
| JP2019532052A5 (https=) | ||
| JP2018529643A (ja) | ユビキチン化−プロテアソーム系に関連する化合物および薬学的組成物 | |
| JP2007529501A (ja) | 疾患の治療のために有用な化合物 | |
| WO2005115147A2 (en) | Hiv reverse transcriptase inhibitors | |
| JP2009541205A5 (https=) | ||
| JP2009185060A (ja) | カンデサルタンシレキセチル多形体 | |
| EP1996585A2 (en) | Bicycloheteroaryl compounds as p2x7 modulators and uses thereof |