JP2010523562A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010523562A5 JP2010523562A5 JP2010502114A JP2010502114A JP2010523562A5 JP 2010523562 A5 JP2010523562 A5 JP 2010523562A5 JP 2010502114 A JP2010502114 A JP 2010502114A JP 2010502114 A JP2010502114 A JP 2010502114A JP 2010523562 A5 JP2010523562 A5 JP 2010523562A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- pyrido
- tetrahydro
- methyl
- pyrimidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 54
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 50
- 208000004296 neuralgia Diseases 0.000 claims description 49
- 201000010099 disease Diseases 0.000 claims description 37
- 208000002193 Pain Diseases 0.000 claims description 32
- 206010029240 Neuritis Diseases 0.000 claims description 18
- -1 cycloheteroalkyl Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 208000035475 disorder Diseases 0.000 claims description 13
- 208000037765 diseases and disorders Diseases 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 208000021722 neuropathic pain Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 201000008482 osteoarthritis Diseases 0.000 claims description 9
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 9
- 208000023275 Autoimmune disease Diseases 0.000 claims description 8
- 208000020925 Bipolar disease Diseases 0.000 claims description 8
- 208000003251 Pruritus Diseases 0.000 claims description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 208000014674 injury Diseases 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 208000019695 Migraine disease Diseases 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 206010043269 Tension headache Diseases 0.000 claims description 7
- 208000008548 Tension-Type Headache Diseases 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 230000006378 damage Effects 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 208000004371 toothache Diseases 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 6
- 230000002159 abnormal effect Effects 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 230000000155 isotopic effect Effects 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 208000023504 respiratory system disease Diseases 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000012453 solvate Substances 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- 206010014599 encephalitis Diseases 0.000 claims description 5
- 230000003959 neuroinflammation Effects 0.000 claims description 5
- 230000009529 traumatic brain injury Effects 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 208000000094 Chronic Pain Diseases 0.000 claims description 4
- 208000006561 Cluster Headache Diseases 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 206010019233 Headaches Diseases 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 206010065390 Inflammatory pain Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 208000005298 acute pain Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 201000009961 allergic asthma Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 230000036506 anxiety Effects 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 208000028683 bipolar I disease Diseases 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 231100000869 headache Toxicity 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 238000001727 in vivo Methods 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 230000002757 inflammatory effect Effects 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 230000000968 intestinal effect Effects 0.000 claims description 4
- 230000007803 itching Effects 0.000 claims description 4
- 150000002632 lipids Chemical class 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 210000002307 prostate Anatomy 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
- 208000036273 reactive airway disease Diseases 0.000 claims description 4
- 230000000241 respiratory effect Effects 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 208000020431 spinal cord injury Diseases 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 206010003399 Arthropod bite Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
- 206010069632 Bladder dysfunction Diseases 0.000 claims description 3
- 206010006784 Burning sensation Diseases 0.000 claims description 3
- 206010008334 Cervicobrachial syndrome Diseases 0.000 claims description 3
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 206010015150 Erythema Diseases 0.000 claims description 3
- 208000034347 Faecal incontinence Diseases 0.000 claims description 3
- 208000001640 Fibromyalgia Diseases 0.000 claims description 3
- 208000014540 Functional gastrointestinal disease Diseases 0.000 claims description 3
- 208000021965 Glossopharyngeal Nerve disease Diseases 0.000 claims description 3
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 208000006877 Insect Bites and Stings Diseases 0.000 claims description 3
- 206010049949 Intercostal neuralgia Diseases 0.000 claims description 3
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 3
- 208000002472 Morton Neuroma Diseases 0.000 claims description 3
- 208000020059 Morton neuralgia Diseases 0.000 claims description 3
- 206010068106 Occipital neuralgia Diseases 0.000 claims description 3
- 208000004983 Phantom Limb Diseases 0.000 claims description 3
- 206010056238 Phantom pain Diseases 0.000 claims description 3
- 206010036105 Polyneuropathy Diseases 0.000 claims description 3
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 claims description 3
- 206010040744 Sinus headache Diseases 0.000 claims description 3
- 208000004078 Snake Bites Diseases 0.000 claims description 3
- 208000003589 Spider Bites Diseases 0.000 claims description 3
- 206010046851 Uveitis Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000002146 bilateral effect Effects 0.000 claims description 3
- 230000036772 blood pressure Effects 0.000 claims description 3
- 201000007637 bowel dysfunction Diseases 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 230000035606 childbirth Effects 0.000 claims description 3
- 231100000321 erythema Toxicity 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 201000005442 glossopharyngeal neuralgia Diseases 0.000 claims description 3
- 230000009610 hypersensitivity Effects 0.000 claims description 3
- 210000003127 knee Anatomy 0.000 claims description 3
- 208000037805 labour Diseases 0.000 claims description 3
- 230000005906 menstruation Effects 0.000 claims description 3
- 230000027939 micturition Effects 0.000 claims description 3
- 201000009985 neuronitis Diseases 0.000 claims description 3
- 201000001119 neuropathy Diseases 0.000 claims description 3
- 208000027232 peripheral nervous system disease Diseases 0.000 claims description 3
- 208000019629 polyneuritis Diseases 0.000 claims description 3
- 210000003497 sciatic nerve Anatomy 0.000 claims description 3
- 230000001953 sensory effect Effects 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 231100000331 toxic Toxicity 0.000 claims description 3
- 230000002588 toxic effect Effects 0.000 claims description 3
- 230000008733 trauma Effects 0.000 claims description 3
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
- RKPAFGOLZJQTPL-IBGZPJMESA-N (2r)-2-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound N1=CC(C)=CC=C1N1CC2=C(N[C@@H](CO)C=3C=CC=CC=3)N=CN=C2CC1 RKPAFGOLZJQTPL-IBGZPJMESA-N 0.000 claims description 2
- COHPLRFPNJNJIX-GOSISDBHSA-N (2s)-2-(6-methoxypyridin-3-yl)-2-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]ethanol Chemical compound C1=NC(OC)=CC=C1[C@@H](CO)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 COHPLRFPNJNJIX-GOSISDBHSA-N 0.000 claims description 2
- WPBBTBJCOJRQNE-QGZVFWFLSA-N (2s)-2-[[6-(5-chloropyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-2-(6-methoxypyridin-3-yl)ethanol Chemical compound C1=NC(OC)=CC=C1[C@@H](CO)NC1=NC=NC2=C1CN(C=1N=CC(Cl)=CC=1)CC2 WPBBTBJCOJRQNE-QGZVFWFLSA-N 0.000 claims description 2
- XTUGYSDHPHABIN-LJQANCHMSA-N (2s)-2-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-2-[4-(trifluoromethyl)phenyl]ethanol Chemical compound N1=CC(C)=CC=C1N1CC2=C(N[C@H](CO)C=3C=CC(=CC=3)C(F)(F)F)N=CN=C2CC1 XTUGYSDHPHABIN-LJQANCHMSA-N 0.000 claims description 2
- RKPAFGOLZJQTPL-LJQANCHMSA-N (2s)-2-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-2-phenylethanol Chemical compound N1=CC(C)=CC=C1N1CC2=C(N[C@H](CO)C=3C=CC=CC=3)N=CN=C2CC1 RKPAFGOLZJQTPL-LJQANCHMSA-N 0.000 claims description 2
- PUIPLPMBTAVSBG-GOSISDBHSA-N (3r)-3-(6-methoxypyridin-3-yl)-3-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]propan-1-ol Chemical compound C1=NC(OC)=CC=C1[C@@H](CCO)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 PUIPLPMBTAVSBG-GOSISDBHSA-N 0.000 claims description 2
- SSNDZSZPTDFBHC-LJQANCHMSA-N (3r)-3-(6-methylpyridin-3-yl)-3-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]propan-1-ol Chemical compound N1=CC(C)=CC=C1N1CC2=C(N[C@H](CCO)C=3C=NC(C)=CC=3)N=CN=C2CC1 SSNDZSZPTDFBHC-LJQANCHMSA-N 0.000 claims description 2
- JYXGOVPRQNIYKV-QGZVFWFLSA-N (3r)-3-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-3-[6-(trifluoromethyl)pyridin-3-yl]propan-1-ol Chemical compound N1=CC(C)=CC=C1N1CC2=C(N[C@H](CCO)C=3C=NC(=CC=3)C(F)(F)F)N=CN=C2CC1 JYXGOVPRQNIYKV-QGZVFWFLSA-N 0.000 claims description 2
- LELBPCNKKRJYQV-UHFFFAOYSA-N 1-(6-methoxypyridin-3-yl)propan-1-ol Chemical compound CCC(O)C1=CN=C(OC)C=C1 LELBPCNKKRJYQV-UHFFFAOYSA-N 0.000 claims description 2
- DTQUOODAYMQTHN-UHFFFAOYSA-N 2-[[6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-yl]amino]-2-pyridin-3-ylethanol Chemical compound N1=CC(C)=CC=C1N1CC2=C(NC(CO)C=3C=NC=CC=3)N=CN=C2CC1 DTQUOODAYMQTHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
- VCVJHUNWPOOPQN-GFCCVEGCSA-N 6-(5-chloropyridin-2-yl)-n-[(1r)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=NC(=CC=1)C(F)(F)F)C(C=1C2)=NC=NC=1CCN2C1=CC=C(Cl)C=N1 VCVJHUNWPOOPQN-GFCCVEGCSA-N 0.000 claims description 2
- VCVJHUNWPOOPQN-LBPRGKRZSA-N 6-(5-chloropyridin-2-yl)-n-[(1s)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)C(C=1C2)=NC=NC=1CCN2C1=CC=C(Cl)C=N1 VCVJHUNWPOOPQN-LBPRGKRZSA-N 0.000 claims description 2
- CMEYRTUYGFNHBD-HXUWFJFHSA-N 6-(5-chloropyridin-2-yl)-n-[(r)-cyclopropyl-[6-(trifluoromethyl)pyridin-3-yl]methyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC(C(F)(F)F)=CC=C1[C@@H](C1CC1)NC1=NC=NC2=C1CN(C=1N=CC(Cl)=CC=1)CC2 CMEYRTUYGFNHBD-HXUWFJFHSA-N 0.000 claims description 2
- CMEYRTUYGFNHBD-FQEVSTJZSA-N 6-(5-chloropyridin-2-yl)-n-[(s)-cyclopropyl-[6-(trifluoromethyl)pyridin-3-yl]methyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=NC(C(F)(F)F)=CC=C1[C@H](C1CC1)NC1=NC=NC2=C1CN(C=1N=CC(Cl)=CC=1)CC2 CMEYRTUYGFNHBD-FQEVSTJZSA-N 0.000 claims description 2
- DGCROPBFIBILRA-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-(1-naphthalen-1-ylethyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 DGCROPBFIBILRA-UHFFFAOYSA-N 0.000 claims description 2
- XVVMIRNQEFEULE-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-(1-phenylpropyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1C(CC)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 XVVMIRNQEFEULE-UHFFFAOYSA-N 0.000 claims description 2
- UUWHBMBIWZIRLD-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-(1-pyridin-2-ylethyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=NC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 UUWHBMBIWZIRLD-UHFFFAOYSA-N 0.000 claims description 2
- KHKPRVFTDKPHCV-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-(1-pyridin-3-ylethyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CN=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 KHKPRVFTDKPHCV-UHFFFAOYSA-N 0.000 claims description 2
- QVWXUUHKIMGPFG-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-(1-pyridin-4-ylethyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=NC=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 QVWXUUHKIMGPFG-UHFFFAOYSA-N 0.000 claims description 2
- MEMSDESZGNUHMN-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-(2,2,2-trifluoro-1-phenylethyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N1=CC(C)=CC=C1N1CC2=C(NC(C=3C=CC=CC=3)C(F)(F)F)N=CN=C2CC1 MEMSDESZGNUHMN-UHFFFAOYSA-N 0.000 claims description 2
- XNAFMMCWOUXFDU-CQSZACIVSA-N 6-(5-methylpyridin-2-yl)-n-[(1r)-1-(2-methylpyrimidin-5-yl)ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=NC(C)=NC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 XNAFMMCWOUXFDU-CQSZACIVSA-N 0.000 claims description 2
- ICLOKAIXSUXTKZ-CQSZACIVSA-N 6-(5-methylpyridin-2-yl)-n-[(1r)-1-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=NC(=CC=1)C(F)(F)F)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 ICLOKAIXSUXTKZ-CQSZACIVSA-N 0.000 claims description 2
- PODLAPNQWXJKQM-MRXNPFEDSA-N 6-(5-methylpyridin-2-yl)-n-[(1r)-1-phenylethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 PODLAPNQWXJKQM-MRXNPFEDSA-N 0.000 claims description 2
- XVVMIRNQEFEULE-IBGZPJMESA-N 6-(5-methylpyridin-2-yl)-n-[(1s)-1-phenylpropyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@@H](CC)C=1C=CC=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 XVVMIRNQEFEULE-IBGZPJMESA-N 0.000 claims description 2
- VEHRIESAOMHDBK-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-[1-(4-methylsulfonylphenyl)ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 VEHRIESAOMHDBK-UHFFFAOYSA-N 0.000 claims description 2
- HNFLMSORXFUDLB-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-[1-[2-(trifluoromethyl)phenyl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 HNFLMSORXFUDLB-UHFFFAOYSA-N 0.000 claims description 2
- RDXICZFIIAPTMJ-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-[1-[3-(trifluoromethyl)phenyl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 RDXICZFIIAPTMJ-UHFFFAOYSA-N 0.000 claims description 2
- KMHMFCXBSABZLF-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-[1-[4-(1,2,4-triazol-1-yl)phenyl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(N2N=CN=C2)C=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 KMHMFCXBSABZLF-UHFFFAOYSA-N 0.000 claims description 2
- KPQNVEFDANSNEJ-UHFFFAOYSA-N 6-(5-methylpyridin-2-yl)-n-[1-[4-(trifluoromethyl)phenyl]ethyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 KPQNVEFDANSNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 208000014644 Brain disease Diseases 0.000 claims description 2
- 208000018569 Respiratory Tract disease Diseases 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 208000029028 brain injury Diseases 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 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 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000005945 imidazopyridyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- BSHIAFMHMKJSPC-MRXNPFEDSA-N n-[(1r)-1-(3-methoxyphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound COC1=CC=CC([C@@H](C)NC=2C=3CN(CCC=3N=CN=2)C=2N=CC(C)=CC=2)=C1 BSHIAFMHMKJSPC-MRXNPFEDSA-N 0.000 claims description 2
- CJYBSPSAYUVDMV-CYBMUJFWSA-N n-[(1r)-1-(4-chlorophenyl)ethyl]-6-(5-chloropyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC(Cl)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(Cl)C=N1 CJYBSPSAYUVDMV-CYBMUJFWSA-N 0.000 claims description 2
- NAJWMPSVESSMGN-OAHLLOKOSA-N n-[(1r)-1-(4-chlorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC(Cl)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 NAJWMPSVESSMGN-OAHLLOKOSA-N 0.000 claims description 2
- DUPYPBQTFOKCSC-OAHLLOKOSA-N n-[(1r)-1-(4-fluorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 DUPYPBQTFOKCSC-OAHLLOKOSA-N 0.000 claims description 2
- YGIOSPPWRLVBJP-MRXNPFEDSA-N n-[(1r)-1-(4-methoxyphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1[C@@H](C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 YGIOSPPWRLVBJP-MRXNPFEDSA-N 0.000 claims description 2
- JSQPMXXGCBUZST-QGZVFWFLSA-N n-[(1r)-1-(4-methylphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@H](C)C=1C=CC(C)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 JSQPMXXGCBUZST-QGZVFWFLSA-N 0.000 claims description 2
- BSHIAFMHMKJSPC-INIZCTEOSA-N n-[(1s)-1-(3-methoxyphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound COC1=CC=CC([C@H](C)NC=2C=3CN(CCC=3N=CN=2)C=2N=CC(C)=CC=2)=C1 BSHIAFMHMKJSPC-INIZCTEOSA-N 0.000 claims description 2
- NAJWMPSVESSMGN-HNNXBMFYSA-N n-[(1s)-1-(4-chlorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@@H](C)C=1C=CC(Cl)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 NAJWMPSVESSMGN-HNNXBMFYSA-N 0.000 claims description 2
- DUPYPBQTFOKCSC-HNNXBMFYSA-N n-[(1s)-1-(4-fluorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@@H](C)C=1C=CC(F)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 DUPYPBQTFOKCSC-HNNXBMFYSA-N 0.000 claims description 2
- YGIOSPPWRLVBJP-INIZCTEOSA-N n-[(1s)-1-(4-methoxyphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1[C@H](C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 YGIOSPPWRLVBJP-INIZCTEOSA-N 0.000 claims description 2
- JSQPMXXGCBUZST-KRWDZBQOSA-N n-[(1s)-1-(4-methylphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound N([C@@H](C)C=1C=CC(C)=CC=1)C(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 JSQPMXXGCBUZST-KRWDZBQOSA-N 0.000 claims description 2
- CLBSVPYCZLWSCF-UHFFFAOYSA-N n-[1-(2,4-dichlorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 CLBSVPYCZLWSCF-UHFFFAOYSA-N 0.000 claims description 2
- HUNKNRMFRKNUAR-UHFFFAOYSA-N n-[1-(2,4-difluorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(F)C=C(F)C=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 HUNKNRMFRKNUAR-UHFFFAOYSA-N 0.000 claims description 2
- YCUDKFILFQRHLI-UHFFFAOYSA-N n-[1-(2-chlorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=C(Cl)C=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 YCUDKFILFQRHLI-UHFFFAOYSA-N 0.000 claims description 2
- GGDAJJXTRCEWJF-UHFFFAOYSA-N n-[1-(2-fluorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC=C(F)C=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 GGDAJJXTRCEWJF-UHFFFAOYSA-N 0.000 claims description 2
- VUJYFXHHIVJFMA-UHFFFAOYSA-N n-[1-(2-methoxy-5-methylphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound COC1=CC=C(C)C=C1C(C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 VUJYFXHHIVJFMA-UHFFFAOYSA-N 0.000 claims description 2
- KCOZDLJGLHTDIQ-UHFFFAOYSA-N n-[1-(2-methoxyphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound COC1=CC=CC=C1C(C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 KCOZDLJGLHTDIQ-UHFFFAOYSA-N 0.000 claims description 2
- STMMULZVHSKPDR-UHFFFAOYSA-N n-[1-(3,5-difluorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C(F)=CC(F)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 STMMULZVHSKPDR-UHFFFAOYSA-N 0.000 claims description 2
- IUPSCNROFMBCEW-UHFFFAOYSA-N n-[1-(3-chlorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC(Cl)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 IUPSCNROFMBCEW-UHFFFAOYSA-N 0.000 claims description 2
- DQEIWRKPVLQBJW-UHFFFAOYSA-N n-[1-(3-fluoro-4-methoxyphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=C(F)C(OC)=CC=C1C(C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 DQEIWRKPVLQBJW-UHFFFAOYSA-N 0.000 claims description 2
- GJAUWURFLVNMPO-UHFFFAOYSA-N n-[1-(3-fluorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=CC(F)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 GJAUWURFLVNMPO-UHFFFAOYSA-N 0.000 claims description 2
- YVOGFFAHHJCXSZ-UHFFFAOYSA-N n-[1-(4-bromophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(Br)C=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 YVOGFFAHHJCXSZ-UHFFFAOYSA-N 0.000 claims description 2
- CNUGQOFQIIDDCR-UHFFFAOYSA-N n-[1-(4-chloro-3-fluorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(Cl)C(F)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 CNUGQOFQIIDDCR-UHFFFAOYSA-N 0.000 claims description 2
- NAJWMPSVESSMGN-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 NAJWMPSVESSMGN-UHFFFAOYSA-N 0.000 claims description 2
- RHMCVUQKMIMGDA-UHFFFAOYSA-N n-[1-(4-ethoxyphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=CC(OCC)=CC=C1C(C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 RHMCVUQKMIMGDA-UHFFFAOYSA-N 0.000 claims description 2
- WTEFMFHLHIXCDB-UHFFFAOYSA-N n-[1-(4-ethylphenyl)ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=CC(CC)=CC=C1C(C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 WTEFMFHLHIXCDB-UHFFFAOYSA-N 0.000 claims description 2
- UFOPSRNDIOHMMG-UHFFFAOYSA-N n-[1-[3,5-bis(trifluoromethyl)phenyl]ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C=1C(C(F)(F)F)=CC(C(F)(F)F)=CC=1C(C)NC(C=1C2)=NC=NC=1CCN2C1=CC=C(C)C=N1 UFOPSRNDIOHMMG-UHFFFAOYSA-N 0.000 claims description 2
- UWKZKGGSAWUHAF-UHFFFAOYSA-N n-[1-[4-(2-methylpropyl)phenyl]ethyl]-6-(5-methylpyridin-2-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-4-amine Chemical compound C1=CC(CC(C)C)=CC=C1C(C)NC1=NC=NC2=C1CN(C=1N=CC(C)=CC=1)CC2 UWKZKGGSAWUHAF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 210000001738 temporomandibular joint Anatomy 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 230000001594 aberrant effect Effects 0.000 claims 1
- 230000001364 causal effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 238000000034 method Methods 0.000 description 10
- 208000012902 Nervous system disease Diseases 0.000 description 3
- 208000025966 Neurological disease Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 208000017169 kidney disease Diseases 0.000 description 3
- 230000000926 neurological effect Effects 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 208000026278 immune system disease Diseases 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US92160407P | 2007-04-02 | 2007-04-02 | |
| US92160307P | 2007-04-02 | 2007-04-02 | |
| US60/921,603 | 2007-04-02 | ||
| US60/921,604 | 2007-04-02 | ||
| PCT/US2008/004202 WO2008123963A1 (en) | 2007-04-02 | 2008-03-31 | Pyrid-2-yl fused heterocyclic compounds, and compositions and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010523562A JP2010523562A (ja) | 2010-07-15 |
| JP2010523562A5 true JP2010523562A5 (enExample) | 2011-04-07 |
| JP5396379B2 JP5396379B2 (ja) | 2014-01-22 |
Family
ID=39831232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010502114A Expired - Fee Related JP5396379B2 (ja) | 2007-04-02 | 2008-03-31 | ピリド−２−イル縮合複素環式化合物ならびにその組成物および使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8653091B2 (enExample) |
| EP (1) | EP2136639B1 (enExample) |
| JP (1) | JP5396379B2 (enExample) |
| CA (1) | CA2682162C (enExample) |
| ES (1) | ES2566387T3 (enExample) |
| WO (1) | WO2008123963A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8076345B2 (en) * | 2007-04-17 | 2011-12-13 | Evotec Ag | 2-cyanophenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine compounds, compositions and uses thereof |
| CA2747170C (en) * | 2008-12-19 | 2017-07-18 | Abbott Laboratories | Tetrahydroisoquinoline derivatives and their uses to treat cancers and autoimmune disorders |
| UA112517C2 (uk) * | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
| EP2619204A4 (en) * | 2010-09-21 | 2014-08-27 | Merck Sharp & Dohme | TRIAZOLOPYRAZINONE AS P2X7 RECEPTOR ANTAGONISTS |
| EA029473B1 (ru) | 2011-12-15 | 2018-03-30 | Новартис Аг | Применение ингибиторов pi3k для лечения острой и церебральной малярии |
| JP6458429B2 (ja) * | 2014-09-30 | 2019-01-30 | 大日本印刷株式会社 | 導電材充填貫通電極基板及びその製造方法 |
| HRP20211002T1 (hr) | 2014-12-09 | 2021-09-17 | Bayer Aktiengesellschaft | 1,3-tiazol-2-il supstituirani benzamidi |
| US10183937B2 (en) | 2014-12-09 | 2019-01-22 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides |
| JP6689297B2 (ja) * | 2015-07-23 | 2020-04-28 | 武田薬品工業株式会社 | 複素環化合物 |
| US20230096028A1 (en) * | 2019-03-01 | 2023-03-30 | Revolution Medicines, Inc. | Bicyclic heterocyclyl compounds and uses thereof |
| AU2020285336A1 (en) | 2019-05-31 | 2022-01-06 | Chiesi Farmaceutici S.P.A. | Amino quinazoline derivatives as P2X3 inhibitors |
| EP3976609A1 (en) | 2019-05-31 | 2022-04-06 | Chiesi Farmaceutici S.p.A. | Pyridopyrimidines derivatives as p2x3 inhibitors |
| WO2022028506A1 (zh) * | 2020-08-06 | 2022-02-10 | 北京泰德制药股份有限公司 | Sos1抑制剂、包含其的药物组合物及其用途 |
| KR20230113536A (ko) * | 2020-11-27 | 2023-07-31 | 키에시 파르마슈티시 엣스. 피. 에이. | P2x3 억제제로서 (아자)퀴놀린 4-아민 유도체 |
| ES3026309T3 (en) | 2020-11-27 | 2025-06-11 | Chiesi Farm Spa | Amino quinazoline derivatives as p2x3 inhibitors |
| CA3196335A1 (en) * | 2020-11-27 | 2022-06-02 | Chiesi Farmaceutici S.P.A. | Phthalazine derivatives as p2x3 inhibitors |
| IL305046A (en) * | 2021-02-08 | 2023-10-01 | Wuhan Humanwell Innovative Drug Res And Development Center Limited Company | Pyridopyrimidinone derivative, the method of preparation thereof and its use |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3424760A (en) * | 1966-03-07 | 1969-01-28 | Robins Co Inc A H | 3-ureidopyrrolidines |
| US3424761A (en) * | 1966-03-07 | 1969-01-28 | Robins Co Inc A H | 3-ureidopyrrolidines |
| DE2502588A1 (de) | 1975-01-23 | 1976-07-29 | Troponwerke Dinklage & Co | Basisch substituierte derivate des 7-amino-2-chinolons, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| PL341356A1 (en) | 1997-12-22 | 2001-04-09 | Bayer Ag | Raf kinase inhibition employing aryl- and heteroaryl-substituted heterocyclic ureas |
| ATE346600T1 (de) | 1997-12-22 | 2006-12-15 | Bayer Pharmaceuticals Corp | Inhibierung der p38 kinase-aktivität durch die verwendung von aryl- und heteroarylsubstituierten harnstoffen |
| DE60023128T2 (de) | 1999-05-12 | 2006-07-06 | Ortho-Mcneil Pharmaceutical, Inc. | Pyrazolcarboxamide zur behandlung von fettleibigkeit und anderen erkrankungen |
| ATE336492T1 (de) | 2000-01-14 | 2006-09-15 | Us Gov Health & Human Serv | Methonocarbacycloalkylanaloga von nucleosiden |
| US6531478B2 (en) | 2000-02-24 | 2003-03-11 | Cheryl P. Kordik | Amino pyrazole derivatives useful for the treatment of obesity and other disorders |
| AU8066701A (en) | 2000-07-20 | 2002-02-05 | Neurogen Corp | Capsaicin receptor ligands |
| WO2002053558A1 (en) | 2001-01-02 | 2002-07-11 | F.Hoffman-La Roche Ag | Quinazolone derivatives as alpha 1a/b adrenergic receptor antagonists |
| WO2002088079A2 (en) * | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| CA2473634C (en) | 2002-02-25 | 2011-11-29 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzofused cycloalkyl urea compounds useful in treating cytokine mediated diseases |
| GB0206033D0 (en) | 2002-03-14 | 2002-04-24 | Pfizer Ltd | Compounds useful in therapy |
| EP1552842A1 (en) * | 2002-06-07 | 2005-07-13 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| GB0225908D0 (en) | 2002-11-06 | 2002-12-11 | Pfizer Ltd | Treatment of female sexual dysfunction |
| US20060100245A1 (en) | 2002-12-19 | 2006-05-11 | Neurogen Corporation | Substituted biphenyl-4-carboxylic acid arylamide analogues |
| WO2005110994A2 (en) | 2004-04-30 | 2005-11-24 | Bayer Pharmaceuticals Corporation | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
| WO2006119504A2 (en) * | 2005-05-04 | 2006-11-09 | Renovis, Inc. | Fused heterocyclic compounds, and compositions and uses thereof |
-
2008
- 2008-03-31 JP JP2010502114A patent/JP5396379B2/ja not_active Expired - Fee Related
- 2008-03-31 CA CA2682162A patent/CA2682162C/en not_active Expired - Fee Related
- 2008-03-31 WO PCT/US2008/004202 patent/WO2008123963A1/en not_active Ceased
- 2008-03-31 EP EP08727238.1A patent/EP2136639B1/en not_active Not-in-force
- 2008-03-31 ES ES08727238.1T patent/ES2566387T3/es active Active
- 2008-03-31 US US12/594,364 patent/US8653091B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010523562A5 (enExample) | ||
| JP2010524930A5 (enExample) | ||
| JP2012502986A5 (enExample) | ||
| JP2008546639A5 (enExample) | ||
| JP2009513703A5 (enExample) | ||
| JP2008534511A5 (enExample) | ||
| JP2011514894A5 (enExample) | ||
| JP2013056930A5 (enExample) | ||
| JP2017533968A5 (enExample) | ||
| JP2008050365A5 (enExample) | ||
| JP2013531055A5 (enExample) | ||
| HRP20110670T1 (hr) | Derivati 4-(2-amino-1-hidroksietil)fenola kao agonisti beta-2 adrenergičkog receptora | |
| JP2015529235A5 (enExample) | ||
| JP2021502387A5 (enExample) | ||
| JP2012523440A5 (enExample) | ||
| JP2009530302A5 (enExample) | ||
| JP2017537948A5 (enExample) | ||
| JP2013538801A5 (enExample) | ||
| JP2007509043A5 (enExample) | ||
| JP2018522852A5 (enExample) | ||
| JP2019532054A5 (enExample) | ||
| JP2019511466A5 (enExample) | ||
| JP2019510801A5 (enExample) | ||
| JP4272056B2 (ja) | アリールピペラジンに連結したテトラヒドロインドロン及びプリン誘導体 | |
| JP2011519845A5 (enExample) |