JP2014534974A - Nampt阻害剤 - Google Patents
Nampt阻害剤 Download PDFInfo
- Publication number
- JP2014534974A JP2014534974A JP2014540288A JP2014540288A JP2014534974A JP 2014534974 A JP2014534974 A JP 2014534974A JP 2014540288 A JP2014540288 A JP 2014540288A JP 2014540288 A JP2014540288 A JP 2014540288A JP 2014534974 A JP2014534974 A JP 2014534974A
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- isoindole
- dihydro
- pyridazin
- cancer
- 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
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- 108010064862 Nicotinamide phosphoribosyltransferase Proteins 0.000 title abstract description 36
- 102000015532 Nicotinamide phosphoribosyltransferase Human genes 0.000 title abstract description 35
- 239000003112 inhibitor Substances 0.000 title description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 45
- 239000000203 mixture Substances 0.000 claims abstract description 38
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 26
- -1 10,10-difluoro-2,7-diazaspiro [4.5] dec-2-yl Chemical group 0.000 claims description 116
- 206010028980 Neoplasm Diseases 0.000 claims description 44
- 201000011510 cancer Diseases 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000003814 drug Substances 0.000 claims description 31
- 208000011580 syndromic disease Diseases 0.000 claims description 24
- 230000002757 inflammatory effect Effects 0.000 claims description 23
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 22
- 208000030507 AIDS Diseases 0.000 claims description 21
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 15
- 206010009944 Colon cancer Diseases 0.000 claims description 14
- 206010025323 Lymphomas Diseases 0.000 claims description 14
- 206010012601 diabetes mellitus Diseases 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 208000032839 leukemia Diseases 0.000 claims description 14
- 229940124597 therapeutic agent Drugs 0.000 claims description 14
- 208000023275 Autoimmune disease Diseases 0.000 claims description 13
- 206010061218 Inflammation Diseases 0.000 claims description 13
- 206010060862 Prostate cancer Diseases 0.000 claims description 13
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 13
- 208000029742 colonic neoplasm Diseases 0.000 claims description 13
- 230000004054 inflammatory process Effects 0.000 claims description 13
- 206010005003 Bladder cancer Diseases 0.000 claims description 12
- 206010006187 Breast cancer Diseases 0.000 claims description 12
- 208000026310 Breast neoplasm Diseases 0.000 claims description 12
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 12
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 12
- 206010033128 Ovarian cancer Diseases 0.000 claims description 12
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 12
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 12
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 12
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 12
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 12
- 201000010881 cervical cancer Diseases 0.000 claims description 12
- 201000005202 lung cancer Diseases 0.000 claims description 12
- 208000020816 lung neoplasm Diseases 0.000 claims description 12
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 12
- 201000002528 pancreatic cancer Diseases 0.000 claims description 12
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 12
- 201000000849 skin cancer Diseases 0.000 claims description 12
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- 201000005112 urinary bladder cancer Diseases 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 11
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 11
- 206010006895 Cachexia Diseases 0.000 claims description 11
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 11
- 208000017604 Hodgkin disease Diseases 0.000 claims description 11
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- 208000001132 Osteoporosis Diseases 0.000 claims description 11
- 201000004681 Psoriasis Diseases 0.000 claims description 11
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 11
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 11
- 208000006011 Stroke Diseases 0.000 claims description 11
- 208000006673 asthma Diseases 0.000 claims description 11
- 201000007455 central nervous system cancer Diseases 0.000 claims description 11
- 230000003176 fibrotic effect Effects 0.000 claims description 11
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 201000006417 multiple sclerosis Diseases 0.000 claims description 11
- 210000000056 organ Anatomy 0.000 claims description 11
- 201000008482 osteoarthritis Diseases 0.000 claims description 11
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- 230000037380 skin damage Effects 0.000 claims description 11
- 208000017520 skin disease Diseases 0.000 claims description 11
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 11
- 230000017423 tissue regeneration Effects 0.000 claims description 11
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 10
- 201000008937 atopic dermatitis Diseases 0.000 claims description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 8
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 8
- 230000000304 vasodilatating effect Effects 0.000 claims description 8
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 7
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 7
- 208000036142 Viral infection Diseases 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 230000009385 viral infection Effects 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- ZFCAYXMJQSTZCA-UHFFFAOYSA-N n-[6-(2-oxa-7-azaspiro[3.5]nonane-7-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(CC1)CCC21COC2 ZFCAYXMJQSTZCA-UHFFFAOYSA-N 0.000 claims description 5
- UDDYMPKSRUKFIC-UHFFFAOYSA-N n-[4-[2-(azepan-1-yl)ethylcarbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCCN1CCCCCC1 UDDYMPKSRUKFIC-UHFFFAOYSA-N 0.000 claims description 4
- 206010003594 Ataxia telangiectasia Diseases 0.000 claims description 3
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 3
- XSRATKZXGGWCRN-UHFFFAOYSA-N n-[4-(1-oxa-8-azaspiro[4.5]decan-3-ylmethylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCC(C1)COC21CCNCC2 XSRATKZXGGWCRN-UHFFFAOYSA-N 0.000 claims description 3
- YAEVCWWABZFWBX-UHFFFAOYSA-N n-[4-(2-hydroxypropylcarbamoyl)phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1=CC(C(=O)NCC(O)C)=CC=C1NC(=O)N1CC2=CC=CC=C2C1 YAEVCWWABZFWBX-UHFFFAOYSA-N 0.000 claims description 3
- FTUWNEQWKOURLX-UHFFFAOYSA-N n-[4-[(2-methyl-2-morpholin-4-ylpropyl)carbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C=1C=C(NC(=O)N2CC3=CC=CC=C3C2)C=CC=1C(=O)NCC(C)(C)N1CCOCC1 FTUWNEQWKOURLX-UHFFFAOYSA-N 0.000 claims description 3
- BWTLJXNAYJRVDI-UHFFFAOYSA-N n-[4-[(2-methyloxolan-2-yl)methylcarbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C=1C=C(NC(=O)N2CC3=CC=CC=C3C2)C=CC=1C(=O)NCC1(C)CCCO1 BWTLJXNAYJRVDI-UHFFFAOYSA-N 0.000 claims description 3
- DFRRTGCVHBYSNN-UHFFFAOYSA-N n-[4-[2-(2-oxoimidazolidin-1-yl)ethylcarbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCCN1CCNC1=O DFRRTGCVHBYSNN-UHFFFAOYSA-N 0.000 claims description 3
- SRVHXWHUNUXWEN-UHFFFAOYSA-N n-[4-[2-(oxan-2-yl)ethylcarbamoyl]phenyl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(C=C1)=CC=C1C(=O)NCCC1CCCCO1 SRVHXWHUNUXWEN-UHFFFAOYSA-N 0.000 claims description 3
- BBTDAGRSEINTPB-UHFFFAOYSA-N n-[6-(1,3,3a,4,6,6a-hexahydrofuro[3,4-c]pyrrole-5-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC1=CC=C(C(=O)N2CC3COCC3C2)N=N1 BBTDAGRSEINTPB-UHFFFAOYSA-N 0.000 claims description 3
- WYNXBIZYIWOJSU-UHFFFAOYSA-N n-[6-(1-oxa-7-azaspiro[4.4]nonane-7-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCC21CCCO2 WYNXBIZYIWOJSU-UHFFFAOYSA-N 0.000 claims description 3
- UEWKXQJQRVCRSR-UHFFFAOYSA-N n-[6-(1-oxa-8-azaspiro[4.5]decan-3-ylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NC(C1)COC21CCNCC2 UEWKXQJQRVCRSR-UHFFFAOYSA-N 0.000 claims description 3
- CWHXMBBUPSCSCQ-UHFFFAOYSA-N n-[6-(1-oxa-8-azaspiro[4.5]decan-3-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NCC(C1)COC21CCNCC2 CWHXMBBUPSCSCQ-UHFFFAOYSA-N 0.000 claims description 3
- FPZKKUTZYAUETO-UHFFFAOYSA-N n-[6-(2,3,3a,4,6,6a-hexahydrofuro[2,3-c]pyrrole-5-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC1=CC=C(C(=O)N2CC3OCCC3C2)N=N1 FPZKKUTZYAUETO-UHFFFAOYSA-N 0.000 claims description 3
- FJWWBHOUTXMVKL-UHFFFAOYSA-N n-[6-(2,6-diazaspiro[3.3]heptane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CC21CNC2 FJWWBHOUTXMVKL-UHFFFAOYSA-N 0.000 claims description 3
- UVZRURWKZQODFO-UHFFFAOYSA-N n-[6-(2,6-diazaspiro[3.4]octane-6-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCC21CNC2 UVZRURWKZQODFO-UHFFFAOYSA-N 0.000 claims description 3
- HCOWADAUVVAOJF-UHFFFAOYSA-N n-[6-(2,6-dioxa-9-azaspiro[4.5]decane-9-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCOC21CCOC2 HCOWADAUVVAOJF-UHFFFAOYSA-N 0.000 claims description 3
- OSCGYYKVQHMMNP-UHFFFAOYSA-N n-[6-(2,7-diazaspiro[3.5]nonane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CC21CCNCC2 OSCGYYKVQHMMNP-UHFFFAOYSA-N 0.000 claims description 3
- NZPGYNJESDXRQX-UHFFFAOYSA-N n-[6-(2,7-diazaspiro[3.5]nonane-7-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(CC1)CCC21CNC2 NZPGYNJESDXRQX-UHFFFAOYSA-N 0.000 claims description 3
- ATTSAEJLHFZVGP-UHFFFAOYSA-N n-[6-(2,7-diazaspiro[4.5]decane-7-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCCC21CCNC2 ATTSAEJLHFZVGP-UHFFFAOYSA-N 0.000 claims description 3
- LMQDLOFHNVIVIB-UHFFFAOYSA-N n-[6-(2,8-diazaspiro[3.5]nonane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CC21CCCNC2 LMQDLOFHNVIVIB-UHFFFAOYSA-N 0.000 claims description 3
- ZIHQTRWFUZXJIQ-UHFFFAOYSA-N n-[6-(2,8-diazaspiro[4.5]decane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCC21CCNCC2 ZIHQTRWFUZXJIQ-UHFFFAOYSA-N 0.000 claims description 3
- NJDJPWURPXKUSA-UHFFFAOYSA-N n-[6-(2,8-diazaspiro[4.5]decane-8-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(CC1)CCC21CCNC2 NJDJPWURPXKUSA-UHFFFAOYSA-N 0.000 claims description 3
- BIRJFHFLIVWGNI-UHFFFAOYSA-N n-[6-(2-azaspiro[3.3]heptan-7-ylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NC1CCC11CNC1 BIRJFHFLIVWGNI-UHFFFAOYSA-N 0.000 claims description 3
- FJSRGIMPJOBXSV-UHFFFAOYSA-N n-[6-(2-oxa-6-azaspiro[3.3]heptane-6-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CC21COC2 FJSRGIMPJOBXSV-UHFFFAOYSA-N 0.000 claims description 3
- MVIVXMXNIBATDV-UHFFFAOYSA-N n-[6-(2-oxa-7-azaspiro[4.4]nonane-7-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCC21CCOC2 MVIVXMXNIBATDV-UHFFFAOYSA-N 0.000 claims description 3
- FIHONAKQUHQAIA-UHFFFAOYSA-N n-[6-(2-oxa-8-azaspiro[3.5]nonane-8-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCCC21COC2 FIHONAKQUHQAIA-UHFFFAOYSA-N 0.000 claims description 3
- QETXHPBHJVKKFA-UHFFFAOYSA-N n-[6-(3,3a,4,6,7,7a-hexahydro-2h-furo[3,2-c]pyridine-5-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC1=CC=C(C(=O)N2CC3CCOC3CC2)N=N1 QETXHPBHJVKKFA-UHFFFAOYSA-N 0.000 claims description 3
- VZZWMVIGBOLQAZ-UHFFFAOYSA-N n-[6-(3,9-diazaspiro[5.5]undecane-3-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(CC1)CCC21CCNCC2 VZZWMVIGBOLQAZ-UHFFFAOYSA-N 0.000 claims description 3
- PVGUPROBNQQMOU-UHFFFAOYSA-N n-[6-(4,5,6,7-tetrahydro-3h-imidazo[4,5-c]pyridin-2-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC1=CC=C(C(=O)NCC=2NC=3CNCCC=3N=2)N=N1 PVGUPROBNQQMOU-UHFFFAOYSA-N 0.000 claims description 3
- FHLDKVRWYIEUNJ-UHFFFAOYSA-N n-[6-(5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazin-3-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC1=CC=C(C(=O)NCC=2N3CCNCC3=NN=2)N=N1 FHLDKVRWYIEUNJ-UHFFFAOYSA-N 0.000 claims description 3
- ZXFAEJWXEYEXRE-UHFFFAOYSA-N n-[6-(5-oxa-2-azaspiro[3.4]octane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CC21CCCO2 ZXFAEJWXEYEXRE-UHFFFAOYSA-N 0.000 claims description 3
- LXXYQIGVLVXPGZ-UHFFFAOYSA-N n-[6-(5-oxa-2-azaspiro[3.5]nonane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CC21CCCCO2 LXXYQIGVLVXPGZ-UHFFFAOYSA-N 0.000 claims description 3
- QBUQIQBDZAHVBE-UHFFFAOYSA-N n-[6-(6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a][1,4]diazepin-3-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1NCCCN2C(CNC(=O)C3=CC=C(N=N3)NC(=O)N3CC4=CC=CC=C4C3)=NN=C21 QBUQIQBDZAHVBE-UHFFFAOYSA-N 0.000 claims description 3
- LZDWEKQORXLOGP-UHFFFAOYSA-N n-[6-(6-azaspiro[2.5]octan-2-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NCC1CC11CCNCC1 LZDWEKQORXLOGP-UHFFFAOYSA-N 0.000 claims description 3
- KKJNBUXRJGXZET-UHFFFAOYSA-N n-[6-(6-fluoro-2,9-diazaspiro[4.5]decane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound FC1CCNCC11CN(C(=O)C=2N=NC(NC(=O)N3CC4=CC=CC=C4C3)=CC=2)CC1 KKJNBUXRJGXZET-UHFFFAOYSA-N 0.000 claims description 3
- PHOQOAUFHKTGPH-UHFFFAOYSA-N n-[6-(6-oxa-2-azaspiro[3.4]octan-7-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NCC(OC1)CC21CNC2 PHOQOAUFHKTGPH-UHFFFAOYSA-N 0.000 claims description 3
- KLWSYGUPMLEFRM-UHFFFAOYSA-N n-[6-(7-azaspiro[3.5]nonan-2-ylmethylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NCC(C1)CC21CCNCC2 KLWSYGUPMLEFRM-UHFFFAOYSA-N 0.000 claims description 3
- QGWSDDBMCHGCJL-UHFFFAOYSA-N n-[6-(7-azaspiro[3.5]nonan-3-ylcarbamoyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)NC1CCC11CCNCC1 QGWSDDBMCHGCJL-UHFFFAOYSA-N 0.000 claims description 3
- XYZXNGTZTSHCMY-UHFFFAOYSA-N n-[6-(7-oxa-2-azaspiro[3.5]nonane-2-carbonyl)pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CC21CCOCC2 XYZXNGTZTSHCMY-UHFFFAOYSA-N 0.000 claims description 3
- QMPDZKBCUCJZBB-UHFFFAOYSA-N n-[6-[(4-fluoropiperidin-4-yl)methylcarbamoyl]pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C=1C=C(NC(=O)N2CC3=CC=CC=C3C2)N=NC=1C(=O)NCC1(F)CCNCC1 QMPDZKBCUCJZBB-UHFFFAOYSA-N 0.000 claims description 3
- VCUSYTIKMYGZID-UHFFFAOYSA-N n-[6-[1-(trifluoromethyl)-2,8-diazaspiro[4.5]decane-2-carbonyl]pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound FC(F)(F)C1N(C(=O)C=2N=NC(NC(=O)N3CC4=CC=CC=C4C3)=CC=2)CCC11CCNCC1 VCUSYTIKMYGZID-UHFFFAOYSA-N 0.000 claims description 3
- VLWXBMAWWDUHTL-UHFFFAOYSA-N n-[6-[3-(azetidin-3-yl)pyrrolidine-1-carbonyl]pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC(N=N1)=CC=C1C(=O)N(C1)CCC1C1CNC1 VLWXBMAWWDUHTL-UHFFFAOYSA-N 0.000 claims description 3
- KDQFPUZHYSMDJR-VMZNBEPHSA-N n-[6-[[(1s,5r)-3-azabicyclo[3.1.0]hexan-6-yl]carbamoyl]pyridazin-3-yl]-1,3-dihydroisoindole-2-carboxamide Chemical compound C1C2=CC=CC=C2CN1C(=O)NC1=CC=C(C(=O)NC2[C@@H]3CNC[C@@H]32)N=N1 KDQFPUZHYSMDJR-VMZNBEPHSA-N 0.000 claims description 3
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Classifications
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Abstract
Description
N−(4−{[2−(アゼパン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{4−[(2−ヒドロキシプロピル)カルバモイル]フェニル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−(2−オキソイミダゾリジン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−(テトラヒドロ−2H−ピラン−2−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[(2−メチルテトラヒドロフラン−2−イル)メチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−メチル−2−(モルホリン−4−イル)プロピル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{4−[(1−オキサ−8−アザスピロ[4.5]デカ−3−イルメチル)カルバモイル]フェニル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−7−アザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(テトラヒドロ−1H−フロ[3,4−c]ピロール−5(3H)−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(ヘキサヒドロフロ[3,2−c]ピリジン−5(4H)−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(ヘキサヒドロ−5H−フロ[2,3−c]ピロール−5−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジオキサ−9−アザスピロ[4.5]デカ−9−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−6−アザスピロ[3.3]ヘプタ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−6−アザスピロ[3.5]ノナ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−7−アザスピロ[4.4]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(10,10−ジフルオロ−2,7−ジアザスピロ[4.5]デカ−2−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(3−シアノ−1−オキサ−8−アザスピロ[4.5]デカ−8−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(7−オキサ−2−アザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(1−オキサ−7−アザスピロ[4.4]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(10−フルオロ−2,7−ジアザスピロ[4.5]デカ−2−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(3,9−ジアザスピロ[5.5]ウンデカ−3−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[4.5]デカ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,8−ジアザスピロ[4.5]デカ−8−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(7−アザスピロ[3.5]ノナ−1−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−アザスピロ[3.3]ヘプタ−5−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1R,5S)−3−アザビシクロ[3.1.0]ヘキサ−6−イルカルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[(7R)−オクタヒドロピロロ[1,2−a]ピラジン−7−イルメチル]カルバモイル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.4]オクタ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(2−オキサ−9−アザスピロ[5.5]ウンデカ−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1−オキサ−8−アザスピロ[4.5]デカ−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1−オキサ−8−アザスピロ[4.5]デカ−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,8−ジアザスピロ[4.5]デカ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[3−(アゼチジン−3−イル)ピロリジン−1−イル]カルボニル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(4,5,6,7−テトラヒドロ−3H−イミダゾ[4,5−c]ピリジン−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(1−オキサ−8−アザスピロ[4.5]デカ−3−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6,7,8,9−テトラヒドロ−5H−[1,2,4]トリアゾロ[4,3−a][1,4]ジアゼピン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6−アザスピロ[2.5]オクタ−1−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(5−オキサ−2−アザスピロ[3.4]オクタ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(5,6,7,8−テトラヒドロ[1,2,4]トリアゾロ[4,3−a]ピラジン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[(4−フルオロピペリジン−4−イル)メチル]カルバモイル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.3]ヘプタ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6−オキサ−2−アザスピロ[3.4]オクタ−7−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(5−オキサ−2−アザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[1−(トリフルオロメチル)−2,8−ジアザスピロ[4.5]デカ−2−イル]カルボニル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(7−アザスピロ[3.5]ノナ−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(5,6,7,8−テトラヒドロ−4H−[1,2,3]トリアゾロ[1,5−a][1,4]ジアゼピン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;およびこれらの医薬として許容される塩から選択される。
本明細書において他に特に規定しない限り、本発明と結び付けて使用する科学用語および技術用語は、当業者であれば一般に理解する意味を有するものとする。これらの用語の意味および範囲は明白でなければならないが、何らかの潜在的あいまい性を備えることが明らかな場合には、本明細書に提供した用語の意味があらゆる辞書もしくは外部の定義に優先される。本出願では、「または」の使用は、他に特に記載しない限り「および/または」を意味する。さらに、用語「含んでいる」ならびに他の形態、例えば「含む」および「に含まれた」の使用は、限定的ではない。本特許出願(請求項を含む。)における用語「含む」または「含んでいる」の使用に関連して、本出願人らは、状況が他のことを要求しない限り、これらの用語は、これらが排他的よりむしろ包含的であるという根拠および明確な理解に基づいて使用する、および本出願人らが下記の特許請求項を含む本特許出願を解釈する際にこれらの用語各々をこのように解釈すべきである。本発明のいずれかの置換基もしくは化合物または本明細書のいずれか他の式において2回以上存在する変量については、各存在に関する定義は、あらゆる他の存在でのこの定義とは無関係である。置換基の組み合わせは、当該の組み合わせが安定性化合物を生じさせる場合にのみ許容される。安定性化合物は、反応混合物から有用な純度で単離できる化合物である。
用語「アルキル」(単独または他の用語と組み合わせて)は、典型的には1から約10個の炭素原子;または他の実施形態では1から約8個の炭素原子;また別の実施形態では、1から約6個の炭素原子;およびまた別の実施形態では、1から約4個の炭素原子を含有する直鎖状もしくは分岐鎖状飽和ヒドロカルビル置換基を意味する。当該の置換基の例には、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、sec−ブチル、tert−ブチル、ペンチル、iso−アミルおよびヘキシルなどが含まれる。
本発明の化合物は、天然において最も豊富に見いだされる原子量もしくは原子量数とは異なる原子質量もしくは原子質量数を有する1個以上の原子を含有する同位体標識もしくは強化形で存在することができる。同位体は、放射性もしくは非放射性同位体であってよい。例えば水素、炭素、リン、硫黄、フッ素、塩素およびヨウ素などの原子の同位体には、2H、3H、13C、14C、15N、18O、32P、35S、18F、36Clおよび125Iが含まれるがこれらに限定されない。これらおよび/または他の原子の他の同位体を含有する化合物は、本発明の範囲内に含まれる。
さらにまた別の実施形態は、
N−(4−{[2−(アゼパン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{4−[(2−ヒドロキシプロピル)カルバモイル]フェニル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−(2−オキソイミダゾリジン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−(テトラヒドロ−2H−ピラン−2−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[(2−メチルテトラヒドロフラン−2−イル)メチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−メチル−2−(モルホリン−4−イル)プロピル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{4−[(1−オキサ−8−アザスピロ[4.5]デカ−3−イルメチル)カルバモイル]フェニル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−7−アザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(テトラヒドロ−1H−フロ[3,4−c]ピロール−5(3H)−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(ヘキサヒドロフロ[3,2−c]ピリジン−5(4H)−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(ヘキサヒドロ−5H−フロ[2,3−c]ピロール−5−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジオキサ−9−アザスピロ[4.5]デカ−9−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−6−アザスピロ[3.3]ヘプタ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−6−アザスピロ[3.5]ノナ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−7−アザスピロ[4.4]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(10,10−ジフルオロ−2,7−ジアザスピロ[4.5]デカ−2−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(3−シアノ−1−オキサ−8−アザスピロ[4.5]デカ−8−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(7−オキサ−2−アザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(1−オキサ−7−アザスピロ[4.4]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(10−フルオロ−2,7−ジアザスピロ[4.5]デカ−2−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(3,9−ジアザスピロ[5.5]ウンデカ−3−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[4.5]デカ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,8−ジアザスピロ[4.5]デカ−8−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(7−アザスピロ[3.5]ノナ−1−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−アザスピロ[3.3]ヘプタ−5−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1R,5S)−3−アザビシクロ[3.1.0]ヘキサ−6−イルカルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[(7R)−オクタヒドロピロロ[1,2−a]ピラジン−7−イルメチル]カルバモイル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.4]オクタ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(2−オキサ−9−アザスピロ[5.5]ウンデカ−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1−オキサ−8−アザスピロ[4.5]デカ−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1−オキサ−8−アザスピロ[4.5]デカ−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,8−ジアザスピロ[4.5]デカ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[3−(アゼチジン−3−イル)ピロリジン−1−イル]カルボニル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(4,5,6,7−テトラヒドロ−3H−イミダゾ[4,5−c]ピリジン−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(1−オキサ−8−アザスピロ[4.5]デカ−3−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6,7,8,9−テトラヒドロ−5H−[1,2,4]トリアゾロ[4,3−a][1,4]ジアゼピン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6−アザスピロ[2.5]オクタ−1−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(5−オキサ−2−アザスピロ[3.4]オクタ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(5,6,7,8−テトラヒドロ[1,2,4]トリアゾロ[4,3−a]ピラジン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[(4−フルオロピペリジン−4−イル)メチル]カルバモイル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.3]ヘプタ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6−オキサ−2−アザスピロ[3.4]オクタ−7−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(5−オキサ−2−アザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[1−(トリフルオロメチル)−2,8−ジアザスピロ[4.5]デカ−2−イル]カルボニル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(7−アザスピロ[3.5]ノナ−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(5,6,7,8−テトラヒドロ−4H−[1,2,3]トリアゾロ[1,5−a][1,4]ジアゼピン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;およびこれらの医薬として許容される塩である化合物に関する。
また別の実施形態は、本明細書の実施例1から49から選択された化合物またはこれらの医薬として許容される塩および賦形剤を含む医薬組成物を含んでいる。
NAMPTの阻害剤への結合剤およびNAMPTの阻害剤としての本明細書の実施例1から49からから選択された化合物およびこれらの医薬として許容される塩についての有用性の決定は、時間分解蛍光共鳴エネルギー移動(TR−FRET)結合アッセイを使用して実施した。
本アッセイは、18μLの低用量プレート(Owens Corning社)内の反応バッファ(50mM HEPES(NaOH)(pH7.5)、100mM NaCl、10mM MgCl2、1mM DTT、1%グリセロ−ル)内で6.8nMの組換えヒトC末端Hisタグ付きNAMPT、1nM Tb−抗His抗体(Invitrogen社、製品番号PV5895)および200nMプローブ(Oregon Green社、488−コンジュゲート化APO866;A−1251667.0)を用いて実施した。プレートを被覆し、反応を2から3時間実施した。プレートは、2から3時間後にEnvision(Laser Lantha低用量プロトコール)を用いて読み取った。励起は337nmで実施し、Oregon Green(520nm)対テルビウム(492nm)の発光比を決定し、これを使用して試験化合物のIC50値を計算した。
以下の略語は、指示した意味を有する。ADDPは、1,1’−(アゾジカルボニル)ジピペリジンを意味する;AD−mix−βは、(DHQD)2PHAL、K3Fe(CN)6、K2CO3およびK2SO4の混合物を意味する;9−BBNは、9−ボラビシクロ(3.3.1)ノナンを意味する;Bocは、tert−ブトキシカルボニルを意味する;(DHQD)2PHALは、ヒドロキニジン1,4−フタラジンジイルジエチルエーテルを意味する;DBUは、1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エンを意味する;DIBALは、ジイソブチルアルミニウムヒドリドを意味する;DIEAは、ジイソプロピルエチルアミンを意味する;DMAPは、N,N−ジメチルアミノピリジンを意味する;DMFは、N,N−ジメチルホルムアミドを意味する;dmpeは、1,2−ビス(ジメチルホスフィノ)エタンを意味する;DMSOは、ジメチルスルホキシドを意味する;dppbは、1,4−ビス(ジフェニルホスフィノ)−ブタンを意味する;dppeは、1,2−ビス(ジフェニルホスフィノ)エタンを意味する;dppfは、1,1’−ビス(ジフェニルホスフィノ)フェロセンを意味する;dppmは、1,1−ビス(ジフェニルホスフィノ)メタンを意味する;EDAC・HClは、1−(3−ジメチルアミノプロピル)−3−エチルカルボジイミドヒドロクロリドを意味する;Fmocは、フルオレニルメトキシカルボニルを意味する;HATUは、O−(7−アザベンゾトリアゾール−1−イル)−N,N’N’N’−テトラメチルウロニウムヘキサフルオロホスフェートを意味する;HMPAは、ヘキサメチルホスホルアミドを意味する;IPAは、イソプロピルアルコールを意味する;MP−BH3は、マクロ多孔性トリエチルアンモニウムメチルポリスチレンシアノボロヒドリドを意味する;TEAは、トリエチルアミンを意味する;TFAは、トリフルオロ酢酸を意味する;THFは、テトラヒドロフランを意味する;NCSは、N−クロロスクシンイミドを意味する;NMMは、N−メチルモルホリンを意味する;NMPは、N−メチルピロリドンを意味する;PPh3は、トリフェニルホスフィンを意味する。
N−(4−{[2−(アゼパン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド
エチル4−イソシアナートベンゾエート
エチル4−(イソインドリン−2−カルボキサミド)ベンゾエート
4−(イソインドリン−2−カルボキサミド)安息香酸
N−(4−{[2−(アゼパン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド
ジクロロメタン(2mL)中の4−(イソインドリン−2−カルボキサミド)安息香酸(100mg、0.35mmol)、1−エチル−3−[3−(ジメチルアミノ)プロピル]−カルボジイミドヒドロクロリド(82mg、0.43mmol)、1−ヒドロキシベンゾトリアゾール水和物(48mg、0.35mmol)およびトリエチルアミン(107mg、1.06mmol)の溶液を室温で30分間攪拌した。次に2−(アゼパン−1−イル)エタナミン(61mg、0.43mmol)を加えた。この混合液を室温で一晩攪拌した。この溶媒を減圧下で除去すると残留物が得られたので、これをprep−HPLCによって精製すると標題化合物が得られた。1H NMR(400MHz,DMSO−d6)・ppm 9.40(s,1H),8.64(s,1H),8.58−8.56(m,1H),7.79−7.76(d,J=8.8Hz,2H),7.70−7.68(d,J=9.2Hz,2H),7.36−7.29(m,4H),4.77(s,4H),3.61−3.57(m,2H),3.47−3.42(m,2H),3.29−3.25(m,2H),3.21−3.14(m,2H),1.82−1.71(m,4H),1.61−1.57(m,4H);MS(ESI(+))m/e407(M+H)+.
以下の実施例は、本質的には実施例1に記載したとおりに、実施例1Dにおける適切なアミンを置換して調製した。生成物を、逆相HPLCによって精製したので、従ってトリフルオロ酢酸塩として単離した。
N−[6−(2−オキサ−7−アザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド
メチル6−アミノピリダジン−3−カルボキシレート
メチル6−イソシアナートピリダジン−3−カルボキシレート
メチル6−(イソインドリン−2−カルボキサミド)ピリダジン−3−カルボキシレート
6−(イソインドリン−2−カルボキサミド)ピリダジン−3−カルボン酸
N−[6−(2−オキサ−7−アザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド
N,N−ジメチルホルムアミド(2mL)中の6−(イソインドリン−2−カルボキサミド)ピリダジン−3−カルボン酸(50mg、0.176mmol)およびO−(7−アザベンゾトリアゾール−1−イル)−N,N,N’,N’−テトラメチルウロニウムヘキサフルオロホスフェート(100mg、0.264mmol)の溶液にジイソプロピルエチルアミン(0.046mL、0.264mmol)および2−オキサ−7−アザスピロ[3.5]ノナン(25mg、0.193mmol)を加えた。この混合液を室温で一晩攪拌した。次にこの混合液を水(10mL)で希釈した。水相をエチルアセテートで抽出した(3×20mL)。結合有機相を食塩液(3×10mL)で洗浄し、Na2SO4で乾燥させ、ろ過して減圧下で濃縮すると、クロマトグラフィ後に標題化合物が得られた。1H NMR(400MHz,DMSO−d6)d ppm 9.89(s,1H),8.25−8.23(d,J=9.6,1H),7.76−7.74(d,J=9.2,1H),7.35−7.29(m,4H),4.84(s,4H),4.36−4.31(q,J=6.0,4H),3.6−3.58(t,J=5.2,2H),3.38−3.35(t,J=5.6,2H),1.87−1.79(m,4H);MS(ESI(+))m/e 394(M+H)+.
以下の実施例は、実施例2Eの適切なアミンを置換して、本質的には実施例1に記載したように調製した。一部の生成物はフラッシュクロマトグラフィによって精製したが、この他は逆相HPLCによって精製した;一部の化合物は、実施例2Dにおけるようにアミドカップリング後にBoc脱保護をさらに必要とした。従って、一部の実施例は、トリフルオロ酢酸塩として単離された。
Claims (4)
- N−(4−{[2−(アゼパン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{4−[(2−ヒドロキシプロピル)カルバモイル]フェニル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−(2−オキソイミダゾリジン−1−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−(テトラヒドロ−2H−ピラン−2−イル)エチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[(2−メチルテトラヒドロフラン−2−イル)メチル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(4−{[2−メチル−2−(モルホリン−4−イル)プロピル]カルバモイル}フェニル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{4−[(1−オキサ−8−アザスピロ[4.5]デカ−3−イルメチル)カルバモイル]フェニル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−7−アザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(テトラヒドロ−1H−フロ[3,4−c]ピロール−5(3H)−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(ヘキサヒドロフロ[3,2−c]ピリジン−5(4H)−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(ヘキサヒドロ−5H−フロ[2,3−c]ピロール−5−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジオキサ−9−アザスピロ[4.5]デカ−9−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−6−アザスピロ[3.3]ヘプタ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−6−アザスピロ[3.5]ノナ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−オキサ−7−アザスピロ[4.4]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(10,10−ジフルオロ−2,7−ジアザスピロ[4.5]デカ−2−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(3−シアノ−1−オキサ−8−アザスピロ[4.5]デカ−8−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(7−オキサ−2−アザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(1−オキサ−7−アザスピロ[4.4]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(10−フルオロ−2,7−ジアザスピロ[4.5]デカ−2−イル)カルボニル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(3,9−ジアザスピロ[5.5]ウンデカ−3−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[4.5]デカ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,8−ジアザスピロ[4.5]デカ−8−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(7−アザスピロ[3.5]ノナ−1−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2−アザスピロ[3.3]ヘプタ−5−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1R,5S)−3−アザビシクロ[3.1.0]ヘキス−6−イルカルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[(7R)−オクタヒドロピロロ[1,2−a]ピラジン−7−イルメチル]カルバモイル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.4]オクタ−6−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(2−オキサ−9−アザスピロ[5.5]ウンデカ−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1−オキサ−8−アザスピロ[4.5]デカ−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(1−オキサ−8−アザスピロ[4.5]デカ−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,7−ジアザスピロ[3.5]ノナ−7−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,8−ジアザスピロ[4.5]デカ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[3−(アゼチジン−3−イル)ピロリジン−1−イル]カルボニル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(4,5,6,7−テトラヒドロ−3H−イミダゾ[4,5−c]ピリジン−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(1−オキサ−8−アザスピロ[4.5]デカ−3−イルカルバモイル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6,7,8,9−テトラヒドロ−5H−[1,2,4]トリアゾロ[4,3−a][1,4]ジアゼピン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6−アザスピロ[2.5]オクタ−1−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(5−オキサ−2−アザスピロ[3.4]オクタ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(5,6,7,8−テトラヒドロ[1,2,4]トリアゾロ[4,3−a]ピラジン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[(4−フルオロピペリジン−4−イル)メチル]カルバモイル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(2,6−ジアザスピロ[3.3]ヘプタ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(6−オキサ−2−アザスピロ[3.4]オクタ−7−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−[6−(5−オキサ−2−アザスピロ[3.5]ノナ−2−イルカルボニル)ピリダジン−3−イル]−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−(6−{[1−(トリフルオロメチル)−2,8−ジアザスピロ[4.5]デカ−2−イル]カルボニル}ピリダジン−3−イル)−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(7−アザスピロ[3.5]ノナ−2−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミド;
N−{6−[(5,6,7,8−テトラヒドロ−4H−[1,2,3]トリアゾロ[1,5−a][1,4]ジアゼピン−3−イルメチル)カルバモイル]ピリダジン−3−イル}−1,3−ジヒドロ−2H−イソインドール−2−カルボキサミドから選択された化合物およびこれらの医薬として許容される塩。 - 炎症性および組織修復性障害、特に、関節リウマチ、炎症性腸症候群、喘息およびCOPD(慢性閉塞性肺疾患)、変形性関節症、骨粗鬆症および線維性疾患;乾癬、アトピー性皮膚炎および紫外線誘発性皮膚損傷を含む皮膚病;全身性エリテマトーデス、多発性硬化症、乾癬性関節炎、強直性脊椎炎、組織および臓器拒絶反応を含む自己免疫疾患;アルツハイマー病、脳卒中、アテローム硬化症、再狭窄症、糖尿病、糸球体腎炎、癌(特に癌は、乳癌、前立腺癌、肺癌、結腸癌、子宮頸癌、卵巣癌、皮膚癌、CNS癌、膀胱癌、膵臓癌、白血病、リンパ腫もしくはホジキン病(Hodgkin’s disease)から選択される。)、悪液質、感染に関連する炎症および後天性免疫不全症候群(AIDS)を含む所定のウイルス感染症、成人呼吸促迫症候群ならびに血管拡張性失調症を治療するための組成物であって、賦形剤および請求項1に記載の治療有効量の化合物またはこれらの医薬として許容される塩を含む組成物。
- 患者における炎症性および組織修復性障害、特に、関節リウマチ、炎症性腸症候群、喘息およびCOPD(慢性閉塞性肺疾患)、変形性関節症、骨粗鬆症および線維性疾患;乾癬、アトピー性皮膚炎および紫外線誘発性皮膚損傷を含む皮膚病;全身性エリテマトーデス、多発性硬化症、乾癬性関節炎、強直性脊椎炎、組織および臓器拒絶反応を含む自己免疫疾患;アルツハイマー病、脳卒中、アテローム硬化症、再狭窄症、糖尿病、糸球体腎炎、癌(特に癌は、乳癌、前立腺癌、肺癌、結腸癌、子宮頸癌、卵巣癌、皮膚癌、CNS癌、膀胱癌、膵臓癌、白血病、リンパ腫もしくはホジキン病から選択される。)、悪液質、感染に関連する炎症および後天性免疫不全症候群(AIDS)を含む所定のウイルス感染症、成人呼吸促迫症候群ならびに血管拡張性失調症を治療するための方法であって、前記患者に請求項1に記載の治療有効量の化合物またはこれらの医薬として許容される塩を投与する工程を含む方法。
- 患者における炎症性および組織修復性障害、特に、関節リウマチ、炎症性腸症候群、喘息およびCOPD(慢性閉塞性肺疾患)、変形性関節症、骨粗鬆症および線維性疾患;乾癬、アトピー性皮膚炎および紫外線誘発性皮膚損傷を含む皮膚病;全身性エリテマトーデス、多発性硬化症、乾癬性関節炎、強直性脊椎炎、組織および臓器拒絶反応を含む自己免疫疾患;アルツハイマー病、脳卒中、アテローム硬化症、再狭窄症、糖尿病、糸球体腎炎、癌(特に癌は、乳癌、前立腺癌、肺癌、結腸癌、子宮頸癌、卵巣癌、皮膚癌、CNS癌、膀胱癌、膵臓癌、白血病、リンパ腫もしくはホジキン病から選択される。)、悪液質、感染に関連する炎症および後天性免疫不全症候群(AIDS)を含む所定のウイルス感染症、成人呼吸促迫症候群ならびに血管拡張性失調症を治療するための方法であって、前記患者に請求項1に記載の治療有効量の化合物またはこれらの医薬として許容される塩ならびに治療有効量の1つの追加の治療薬もしくは2つ以上の追加の治療薬を投与する工程を含む方法。
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JP2014540288A Expired - Fee Related JP5980340B2 (ja) | 2011-11-11 | 2011-11-11 | Nampt阻害剤 |
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US (1) | US20160031813A1 (ja) |
EP (1) | EP2776393B1 (ja) |
JP (1) | JP5980340B2 (ja) |
CA (1) | CA2855510A1 (ja) |
MX (1) | MX348311B (ja) |
WO (1) | WO2013067710A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2019524716A (ja) * | 2016-07-14 | 2019-09-05 | ファイザー・インク | バニン1酵素の阻害薬としての新規のピリミジンカルボキサミド |
JP2021130662A (ja) * | 2015-06-19 | 2021-09-09 | ノバルティス アーゲー | Shp2の活性を阻害するための化合物および組成物 |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EA201692091A1 (ru) | 2014-04-18 | 2017-04-28 | Милленниум Фармасьютикалз, Инк. | Хиноксалиновые соединения и их применение |
TW201625641A (zh) * | 2014-05-22 | 2016-07-16 | 健臻公司 | Nampt抑制劑及方法 |
SG11201700039TA (en) | 2014-07-23 | 2017-02-27 | Aurigene Discovery Tech Ltd | 4,5-dihydroisoxazole derivatives as nampt inhibitors |
CN105601640B (zh) * | 2014-11-19 | 2018-08-03 | 天津药明康德新药开发有限公司 | 一种n-叔丁氧羰基-7-(胺甲基)-6-氧杂-2-螺[4.5]癸烷的合成方法 |
EP3247705B1 (en) | 2015-01-20 | 2019-11-20 | Millennium Pharmaceuticals, Inc. | Quinazoline and quinoline compounds and uses thereof as nampt inhibitors |
KR20190074292A (ko) | 2016-10-18 | 2019-06-27 | 시애틀 지네틱스, 인크. | 니코틴아미드 아데닌 디뉴클레오티드의 구제 경로 저해제의 표적화된 전달 |
MA51189A (fr) | 2017-04-27 | 2020-03-04 | Seattle Genetics Inc | Conjugués d'inhibiteur de la voie de récupération du nicotinamide adénine dinucléotide quaternarisé |
JP2021512103A (ja) | 2018-01-31 | 2021-05-13 | バイエル アクチェンゲゼルシャフトBayer Aktiengesellschaft | Nampt阻害剤を含む抗体薬物複合体(adcs) |
EP3856735B1 (en) * | 2018-10-05 | 2023-09-06 | New York University | Fused bicyclic heterocycles as therapeutic agents |
WO2021013693A1 (en) | 2019-07-23 | 2021-01-28 | Bayer Pharma Aktiengesellschaft | Antibody drug conjugates (adcs) with nampt inhibitors |
Citations (1)
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WO2011109441A1 (en) * | 2010-03-01 | 2011-09-09 | Myrexis, Inc. | Compounds and therapeutic uses thereof |
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GB0705882D0 (en) * | 2007-03-27 | 2007-05-02 | Glaxo Group Ltd | Novel compounds |
WO2010033349A1 (en) * | 2008-09-16 | 2010-03-25 | Merck & Co., Inc. | Phthalimide derivative metabotropic glutamate r4 ligands |
EP2454237B1 (en) * | 2009-07-14 | 2016-09-07 | Nerviano Medical Sciences S.r.l. | 3-oxo-2,3,-dihydro-1h-isoindole-4-carboxamides with selective parp-1 inhibition |
US9302989B2 (en) * | 2010-11-15 | 2016-04-05 | Abbvie Inc. | NAMPT and rock inhibitors |
-
2011
- 2011-11-11 EP EP11875269.0A patent/EP2776393B1/en not_active Not-in-force
- 2011-11-11 JP JP2014540288A patent/JP5980340B2/ja not_active Expired - Fee Related
- 2011-11-11 CA CA2855510A patent/CA2855510A1/en not_active Abandoned
- 2011-11-11 US US14/358,368 patent/US20160031813A1/en not_active Abandoned
- 2011-11-11 MX MX2014005730A patent/MX348311B/es active IP Right Grant
- 2011-11-11 WO PCT/CN2011/082108 patent/WO2013067710A1/en active Application Filing
Patent Citations (1)
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WO2011109441A1 (en) * | 2010-03-01 | 2011-09-09 | Myrexis, Inc. | Compounds and therapeutic uses thereof |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2021130662A (ja) * | 2015-06-19 | 2021-09-09 | ノバルティス アーゲー | Shp2の活性を阻害するための化合物および組成物 |
JP7146016B2 (ja) | 2015-06-19 | 2022-10-03 | ノバルティス アーゲー | Shp2の活性を阻害するための化合物および組成物 |
JP2019524716A (ja) * | 2016-07-14 | 2019-09-05 | ファイザー・インク | バニン1酵素の阻害薬としての新規のピリミジンカルボキサミド |
Also Published As
Publication number | Publication date |
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JP5980340B2 (ja) | 2016-08-31 |
CA2855510A1 (en) | 2013-05-16 |
EP2776393A4 (en) | 2015-05-27 |
MX2014005730A (es) | 2014-10-13 |
MX348311B (es) | 2017-06-06 |
EP2776393B1 (en) | 2017-12-20 |
CN104039762A (zh) | 2014-09-10 |
US20160031813A1 (en) | 2016-02-04 |
WO2013067710A1 (en) | 2013-05-16 |
EP2776393A1 (en) | 2014-09-17 |
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