JP2013508405A5 - - Google Patents
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- Publication number
- JP2013508405A5 JP2013508405A5 JP2012535386A JP2012535386A JP2013508405A5 JP 2013508405 A5 JP2013508405 A5 JP 2013508405A5 JP 2012535386 A JP2012535386 A JP 2012535386A JP 2012535386 A JP2012535386 A JP 2012535386A JP 2013508405 A5 JP2013508405 A5 JP 2013508405A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- diazabicyclo
- triazol
- fluoro
- octane
- 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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- -1 1H-pyrazol-1-yl Chemical group 0.000 claims 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 20
- 239000000126 substance Substances 0.000 claims 18
- 125000001475 halogen functional group Chemical group 0.000 claims 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 10
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 6
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 5
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 5
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- HBAPRWLCCBZDNA-UHFFFAOYSA-N 4-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidine Chemical compound CC1=NC=NC2=C1CCC2 HBAPRWLCCBZDNA-UHFFFAOYSA-N 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 3
- VZWOXDYRBDIHMA-UHFFFAOYSA-N 2-methyl-1,3-thiazole Chemical group CC1=NC=CS1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- GKVDLTTVBNOGNJ-UHFFFAOYSA-N 2-methylpyrimidin-4-amine Chemical compound CC1=NC=CC(N)=N1 GKVDLTTVBNOGNJ-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- JJOOKXUUVWIARB-UHFFFAOYSA-N 6-chloro-1,3-benzoxazole Chemical compound ClC1=CC=C2N=COC2=C1 JJOOKXUUVWIARB-UHFFFAOYSA-N 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- RZWKLEHRXNOKGT-UHFFFAOYSA-N CC=1C(=C(C=CC1)C=O)C1=CC=NN1 Chemical compound CC=1C(=C(C=CC1)C=O)C1=CC=NN1 RZWKLEHRXNOKGT-UHFFFAOYSA-N 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010033307 Overweight Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- 208000001871 Tachycardia Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 206010022437 insomnia Diseases 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- KDUWWQCGLSYDIY-UHFFFAOYSA-N n,n,2-trimethylpyrimidin-4-amine Chemical compound CN(C)C1=CC=NC(C)=N1 KDUWWQCGLSYDIY-UHFFFAOYSA-N 0.000 claims 2
- LAURYIYOSYVBIZ-UHFFFAOYSA-N n,n,4-trimethylpyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(C)=N1 LAURYIYOSYVBIZ-UHFFFAOYSA-N 0.000 claims 2
- MSXIOWULDXZJLX-UHFFFAOYSA-N n,n-dimethylpyrimidin-4-amine Chemical compound CN(C)C1=CC=NC=N1 MSXIOWULDXZJLX-UHFFFAOYSA-N 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 235000020825 overweight Nutrition 0.000 claims 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 230000006794 tachycardia Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- ZERSCKSOBJMLBC-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-(4-quinoxalin-6-yl-4,7-diazabicyclo[4.2.0]octan-7-yl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C2CN(C=3C=C4N=CC=NC4=CC=3)CCC2C1 ZERSCKSOBJMLBC-UHFFFAOYSA-N 0.000 claims 1
- MERAYSGZQADQGE-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-[4-(4-phenylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C2CN(C=3N=C(C=CN=3)C=3C=CC=CC=3)CCC2C1 MERAYSGZQADQGE-UHFFFAOYSA-N 0.000 claims 1
- USOABOIEIQKGGQ-UHFFFAOYSA-N (2-bromophenyl)-[3-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]methanone Chemical compound CC1=CC(C)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2)Br)=N1 USOABOIEIQKGGQ-UHFFFAOYSA-N 0.000 claims 1
- GXDONUFNDCCJQI-UHFFFAOYSA-N (2-bromophenyl)-[3-(4-methylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]methanone Chemical compound CC1=CC=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2)Br)=N1 GXDONUFNDCCJQI-UHFFFAOYSA-N 0.000 claims 1
- JXXXJWSNTPQUSL-UHFFFAOYSA-N (2-phenylphenyl)-(3-quinoxalin-2-yl-3,6-diazabicyclo[3.2.0]heptan-6-yl)methanone Chemical compound C1C2CN(C=3N=C4C=CC=CC4=NC=3)CC2N1C(=O)C1=CC=CC=C1C1=CC=CC=C1 JXXXJWSNTPQUSL-UHFFFAOYSA-N 0.000 claims 1
- NCRSYKPNXDTNQA-UHFFFAOYSA-N (2-phenylphenyl)-(4-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-7-yl)methanone Chemical compound C1C2CCN(C=3N=C4C=CC=CC4=NC=3)CC2N1C(=O)C1=CC=CC=C1C1=CC=CC=C1 NCRSYKPNXDTNQA-UHFFFAOYSA-N 0.000 claims 1
- WWHREMBTHQBQAA-UHFFFAOYSA-N (2-phenylphenyl)-[3-(4-phenylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]methanone Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)N(C1C2)CC1CN2C(N=1)=NC=CC=1C1=CC=CC=C1 WWHREMBTHQBQAA-UHFFFAOYSA-N 0.000 claims 1
- FCAOJQYTXNQTOI-UHFFFAOYSA-N (2-phenylphenyl)-[4-(4-phenylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)N(C1C2)CC1CCN2C(N=1)=NC=CC=1C1=CC=CC=C1 FCAOJQYTXNQTOI-UHFFFAOYSA-N 0.000 claims 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 1
- YHUWINJRLYIHCD-UHFFFAOYSA-N 2-[7-(2,5-dimethylphenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octan-4-yl]quinoxaline Chemical compound CC1=CC=C(C)C(S(=O)(=O)N2C3CN(CCC3C2)C=2N=C3C=CC=CC3=NC=2)=C1 YHUWINJRLYIHCD-UHFFFAOYSA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- YESCPKTWTUCNTK-UHFFFAOYSA-N 2-fluoro-6-(triazol-2-yl)benzaldehyde Chemical compound FC1=C(C(=CC=C1)N1N=CC=N1)C=O YESCPKTWTUCNTK-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- AGFPGULYIMKQGT-UHFFFAOYSA-N 3-fluoro-2-(1H-pyrazol-5-yl)benzaldehyde Chemical compound FC=1C(=C(C=CC=1)C=O)C=1NN=CC=1 AGFPGULYIMKQGT-UHFFFAOYSA-N 0.000 claims 1
- QSYWKQLZNHTFCV-UHFFFAOYSA-N 3-fluoro-2-(triazol-2-yl)benzaldehyde Chemical compound FC1=CC=CC(C=O)=C1N1N=CC=N1 QSYWKQLZNHTFCV-UHFFFAOYSA-N 0.000 claims 1
- OBFNEMXIPDVHRI-UHFFFAOYSA-N 4-fluoro-2-pyrimidin-2-ylbenzaldehyde Chemical compound FC1=CC(=C(C=C1)C=O)C1=NC=CC=N1 OBFNEMXIPDVHRI-UHFFFAOYSA-N 0.000 claims 1
- ZJTUYXLOPPDBGH-UHFFFAOYSA-N 4-methoxy-2-(triazol-2-yl)benzaldehyde Chemical compound COC1=CC=C(C=O)C(N2N=CC=N2)=C1 ZJTUYXLOPPDBGH-UHFFFAOYSA-N 0.000 claims 1
- NUZBBIHTIXZDDY-UHFFFAOYSA-N 7-(2,5-dimethylphenyl)sulfonyl-4-(4-phenylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound CC1=CC=C(C)C(S(=O)(=O)N2C3CN(CCC3C2)C=2N=C(C=CN=2)C=2C=CC=CC=2)=C1 NUZBBIHTIXZDDY-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006820 Arthralgia Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010007556 Cardiac failure acute Diseases 0.000 claims 1
- 206010012218 Delirium Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- PGEXEBHDXNLTIE-UHFFFAOYSA-N FC=1C(=C(C=CC1)C=O)C1=CC(=NO1)C Chemical compound FC=1C(=C(C=CC1)C=O)C1=CC(=NO1)C PGEXEBHDXNLTIE-UHFFFAOYSA-N 0.000 claims 1
- STLYQTNIULBKGY-UHFFFAOYSA-N FC=1C(=C(C=CC1)C=O)C1=CC=NO1 Chemical compound FC=1C(=C(C=CC1)C=O)C1=CC=NO1 STLYQTNIULBKGY-UHFFFAOYSA-N 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 208000008930 Low Back Pain Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 102000002512 Orexin Human genes 0.000 claims 1
- 108050000742 Orexin Receptor Proteins 0.000 claims 1
- 102000008834 Orexin receptor Human genes 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- ZFZULBCQSGGOHR-DNVCBOLYSA-N [(1r,6s)-4-(4,5-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound N1=C(C)C(C)=CN=C1N1C[C@H]2N(C(=O)C=3C(=CC=C(F)C=3)N3N=CC=N3)C[C@H]2CC1 ZFZULBCQSGGOHR-DNVCBOLYSA-N 0.000 claims 1
- DBODIMKUPBUYBB-SJLPKXTDSA-N [(1r,6s)-4-(4,5-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[6-methyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=CC=C(N=C2N2N=NC=C2)C)CN1C1=NC=C(C)C(C)=N1 DBODIMKUPBUYBB-SJLPKXTDSA-N 0.000 claims 1
- VNNKBQGOFHYHOZ-VQIMIIECSA-N [(1r,6s)-4-(4,6-dimethylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=C1 VNNKBQGOFHYHOZ-VQIMIIECSA-N 0.000 claims 1
- ARCNMXAESGIZJJ-VQIMIIECSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-(3-fluoro-2-pyrazol-1-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=C2)=N1 ARCNMXAESGIZJJ-VQIMIIECSA-N 0.000 claims 1
- RAWRQCGINRXFGJ-VQIMIIECSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-(3-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)C=2N=CC=CN=2)=N1 RAWRQCGINRXFGJ-VQIMIIECSA-N 0.000 claims 1
- RNPBAIRMGAFCTD-UYAOXDASSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-(3-methyl-2-pyrazol-1-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(C)C=CC=2)N2N=CC=C2)=N1 RNPBAIRMGAFCTD-UYAOXDASSA-N 0.000 claims 1
- NFHNWNGGAXTAHB-VQIMIIECSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(=O)N2[C@@H]3CN(CC[C@@H]3C2)C=2N=C(C)C=C(C)N=2)=N1 NFHNWNGGAXTAHB-VQIMIIECSA-N 0.000 claims 1
- QMUHLWWRQXORGR-CRAIPNDOSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-fluoro-6-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C(=C(F)C=CC=2)C(=O)N2[C@@H]3CN(CC[C@@H]3C2)C=2N=C(C)C=C(C)N=2)=N1 QMUHLWWRQXORGR-CRAIPNDOSA-N 0.000 claims 1
- GDIQDZVRMKTDML-CRAIPNDOSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 GDIQDZVRMKTDML-CRAIPNDOSA-N 0.000 claims 1
- VQLZITAIIORYNU-DNVCBOLYSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-fluoro-2-(1h-pyrazol-5-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)C=2NN=CC=2)=N1 VQLZITAIIORYNU-DNVCBOLYSA-N 0.000 claims 1
- CNVDHNKVDSWDHK-CRAIPNDOSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-fluoro-2-(triazol-1-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)N2N=NC=C2)=N1 CNVDHNKVDSWDHK-CRAIPNDOSA-N 0.000 claims 1
- KPLJXBDVXNWNGI-CRAIPNDOSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 KPLJXBDVXNWNGI-CRAIPNDOSA-N 0.000 claims 1
- MUKSCISAZPPELV-SJLPKXTDSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-methoxy-2-(triazol-1-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C=CC=C(C=2N2N=NC=C2)OC)CN1C1=NC(C)=CC(C)=N1 MUKSCISAZPPELV-SJLPKXTDSA-N 0.000 claims 1
- RHJBVNFMVXMMQA-SJLPKXTDSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C=CC=C(C=2N2N=CC=N2)OC)CN1C1=NC(C)=CC(C)=N1 RHJBVNFMVXMMQA-SJLPKXTDSA-N 0.000 claims 1
- KALRYPOHHCRTNN-IEBWSBKVSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-methyl-2-(triazol-1-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(C)C=CC=2)N2N=NC=C2)=N1 KALRYPOHHCRTNN-IEBWSBKVSA-N 0.000 claims 1
- IPKRWZKTQZLMOQ-OXQOHEQNSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)CN1C1=NC(C)=CC(C)=N1 IPKRWZKTQZLMOQ-OXQOHEQNSA-N 0.000 claims 1
- FLWWBLDVCVQTRI-DNVCBOLYSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 FLWWBLDVCVQTRI-DNVCBOLYSA-N 0.000 claims 1
- XTBUKDIQTIIDEW-OXQOHEQNSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)CN1C1=NC(C)=CC(C)=N1 XTBUKDIQTIIDEW-OXQOHEQNSA-N 0.000 claims 1
- MTLHNBTZPPYZMD-SJLPKXTDSA-N [(1r,6s)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[6-methyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=CC=C(N=C2N2N=NC=C2)C)CN1C1=NC(C)=CC(C)=N1 MTLHNBTZPPYZMD-SJLPKXTDSA-N 0.000 claims 1
- DHGNKEKRMDXCQR-CXAGYDPISA-N [(1r,6s)-4-(4-aminopyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)CN1C1=NC=CC(N)=N1 DHGNKEKRMDXCQR-CXAGYDPISA-N 0.000 claims 1
- MBJQSBKKTPPLFW-SJLPKXTDSA-N [(1r,6s)-4-(4-methylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[6-methyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound CC1=CC=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=NC(C)=CC=2)N2N=NC=C2)=C1 MBJQSBKKTPPLFW-SJLPKXTDSA-N 0.000 claims 1
- SCAZJSXMMAEAFL-CRAIPNDOSA-N [(1r,6s)-4-(5-chloro-4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(=O)N2[C@@H]3CN(CC[C@@H]3C2)C=2N=C(C)C(Cl)=C(C)N=2)=N1 SCAZJSXMMAEAFL-CRAIPNDOSA-N 0.000 claims 1
- ZNRGINVDUKPUGG-RDTXWAMCSA-N [(1r,6s)-4-(5-chloro-4-methylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(=O)N2[C@@H]3CN(CC[C@@H]3C2)C=2N=C(C)C(Cl)=CN=2)=N1 ZNRGINVDUKPUGG-RDTXWAMCSA-N 0.000 claims 1
- FTJRZQDAPUBTRL-CRAIPNDOSA-N [(1r,6s)-4-(5-fluoro-4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(=O)N2[C@@H]3CN(CC[C@@H]3C2)C=2N=C(C)C(F)=C(C)N=2)=N1 FTJRZQDAPUBTRL-CRAIPNDOSA-N 0.000 claims 1
- QAWGVYWAZNEIQG-RHSMWYFYSA-N [(1r,6s)-4-(5-fluoro-4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-fluoro-2-(1,2-oxazol-5-yl)phenyl]methanone Chemical compound CC1=C(F)C(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)C=2ON=CC=2)=N1 QAWGVYWAZNEIQG-RHSMWYFYSA-N 0.000 claims 1
- GZVFQNVGXNUCDW-RDTXWAMCSA-N [(1r,6s)-4-(5-fluoro-4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-fluoro-2-(1h-pyrazol-5-yl)phenyl]methanone Chemical compound CC1=C(F)C(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)C=2NN=CC=2)=N1 GZVFQNVGXNUCDW-RDTXWAMCSA-N 0.000 claims 1
- GJJBYNIKRYEDKK-CRAIPNDOSA-N [(1r,6s)-4-(5-fluoro-4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-fluoro-2-(3-methyl-1,2-oxazol-5-yl)phenyl]methanone Chemical compound O1N=C(C)C=C1C1=C(F)C=CC=C1C(=O)N1[C@@H]2CN(C=3N=C(C)C(F)=C(C)N=3)CC[C@@H]2C1 GJJBYNIKRYEDKK-CRAIPNDOSA-N 0.000 claims 1
- MTPLZRJKIYAGIP-CXAGYDPISA-N [(1r,6s)-4-(5-fluoro-4-methylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C1=C(F)C(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 MTPLZRJKIYAGIP-CXAGYDPISA-N 0.000 claims 1
- MGMPEAOCKQATPX-AUUYWEPGSA-N [(1r,6s)-4-(5-fluoro-4-methylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)CN1C1=NC=C(F)C(C)=N1 MGMPEAOCKQATPX-AUUYWEPGSA-N 0.000 claims 1
- PXPUTKAXBSAKFK-RHSMWYFYSA-N [(1r,6s)-4-(5-fluoro-4-methylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[6-methyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=CC=C(N=C2N2N=NC=C2)C)CN1C1=NC=C(F)C(C)=N1 PXPUTKAXBSAKFK-RHSMWYFYSA-N 0.000 claims 1
- YQBCCVKQJDKKLH-RDTXWAMCSA-N [(1r,6s)-4-(6-chloro-1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[6-methyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound N=1C(C)=CC=C(C(=O)N2[C@@H]3CN(CC[C@@H]3C2)C=2OC3=CC(Cl)=CC=C3N=2)C=1N1C=CN=N1 YQBCCVKQJDKKLH-RDTXWAMCSA-N 0.000 claims 1
- BWZPGVXWIPAXHT-OXQOHEQNSA-N [(1r,6s)-4-[2-(dimethylamino)-6-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)CN1C1=CC(C)=NC(N(C)C)=N1 BWZPGVXWIPAXHT-OXQOHEQNSA-N 0.000 claims 1
- XYDFOQGVMNVZED-OXQOHEQNSA-N [(1r,6s)-4-[2-(dimethylamino)-6-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)CN1C1=CC(C)=NC(N(C)C)=N1 XYDFOQGVMNVZED-OXQOHEQNSA-N 0.000 claims 1
- JZNNDXCXDLORRN-OXQOHEQNSA-N [(1r,6s)-4-[6-(dimethylamino)-2-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)CN1C1=CC(N(C)C)=NC(C)=N1 JZNNDXCXDLORRN-OXQOHEQNSA-N 0.000 claims 1
- WZEYQMOJZMWFRR-OXQOHEQNSA-N [(1r,6s)-4-[6-(dimethylamino)-2-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)CN1C1=CC(N(C)C)=NC(C)=N1 WZEYQMOJZMWFRR-OXQOHEQNSA-N 0.000 claims 1
- MQKFUBZBDXWABR-CRAIPNDOSA-N [(1r,6s)-4-[6-(dimethylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound C1=NC(N(C)C)=CC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=CC=CC=2)C=2ON=C(C)N=2)=N1 MQKFUBZBDXWABR-CRAIPNDOSA-N 0.000 claims 1
- MXTVTJUCDQIPFH-CRAIPNDOSA-N [(1r,6s)-4-[6-(dimethylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1=NC(N(C)C)=CC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 MXTVTJUCDQIPFH-CRAIPNDOSA-N 0.000 claims 1
- WPXGIWSOQDTKFO-DNVCBOLYSA-N [(1r,6s)-4-[6-(dimethylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)CN1C1=CC(N(C)C)=NC=N1 WPXGIWSOQDTKFO-DNVCBOLYSA-N 0.000 claims 1
- FSRQWMZGEOOPHT-DNVCBOLYSA-N [(1r,6s)-4-[6-(dimethylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)CN1C1=CC(N(C)C)=NC=N1 FSRQWMZGEOOPHT-DNVCBOLYSA-N 0.000 claims 1
- YJDODUFNQDTQKZ-REWPJTCUSA-N [(1s,6r)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-(2-phenylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2C[C@@H]3N(C[C@@H]3CC2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 YJDODUFNQDTQKZ-REWPJTCUSA-N 0.000 claims 1
- UJSDQRUUAHJSND-PXNSSMCTSA-N [(1s,6r)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2C[C@@H]3N(C[C@@H]3CC2)C(=O)C=2C(=CC=CC=2)C=2SC=CC=2)=N1 UJSDQRUUAHJSND-PXNSSMCTSA-N 0.000 claims 1
- GDIQDZVRMKTDML-YJBOKZPZSA-N [(1s,6r)-4-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C[C@@H]3N(C[C@@H]3CC2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 GDIQDZVRMKTDML-YJBOKZPZSA-N 0.000 claims 1
- KNERPANAKIIIDU-YLJYHZDGSA-N [2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]-[(1r,6s)-4-(4,5,6-trimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(=O)N2[C@@H]3CN(CC[C@@H]3C2)C=2N=C(C)C(C)=C(C)N=2)=N1 KNERPANAKIIIDU-YLJYHZDGSA-N 0.000 claims 1
- SZKASESVFVXQAK-UZUQRXQVSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1r,6s)-4-(2-methylquinolin-4-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound C([C@H]1CCN(C[C@H]11)C=2C=C(N=C3C=CC=CC3=2)C)N1C(=O)C1=C(F)C=CC=C1N1N=CC=N1 SZKASESVFVXQAK-UZUQRXQVSA-N 0.000 claims 1
- ZDIDFEWWLZIXGF-VQIMIIECSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1r,6s)-4-(4,5,6-trimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound CC1=C(C)C(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 ZDIDFEWWLZIXGF-VQIMIIECSA-N 0.000 claims 1
- NPXVZFRHSSBVEF-IUODEOHRSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1r,6s)-4-[4-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C2=C(C=CC=C2F)N2N=CC=N2)CN1C1=NC=CC(C(F)(F)F)=N1 NPXVZFRHSSBVEF-IUODEOHRSA-N 0.000 claims 1
- VPFCLKHXIUNDJX-OPAMFIHVSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1r,6s)-4-quinolin-4-yl-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound N1([C@@H]2CN(CC[C@@H]2C1)C=1C2=CC=CC=C2N=CC=1)C(=O)C=1C(F)=CC=CC=1N1N=CC=N1 VPFCLKHXIUNDJX-OPAMFIHVSA-N 0.000 claims 1
- NPXVZFRHSSBVEF-WFASDCNBSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1s,6r)-4-[4-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound C([C@H]1CN([C@H]1C1)C(=O)C2=C(C=CC=C2F)N2N=CC=N2)CN1C1=NC=CC(C(F)(F)F)=N1 NPXVZFRHSSBVEF-WFASDCNBSA-N 0.000 claims 1
- DUZGNMGVQFOPMO-UHFFFAOYSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[3-[4-methyl-6-(trifluoromethyl)pyrimidin-2-yl]-3,6-diazabicyclo[3.2.0]heptan-6-yl]methanone Chemical compound CC1=CC(C(F)(F)F)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 DUZGNMGVQFOPMO-UHFFFAOYSA-N 0.000 claims 1
- NAQKCUDYBFCCNK-UHFFFAOYSA-N [3-(3,6-dimethylpyrazin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 NAQKCUDYBFCCNK-UHFFFAOYSA-N 0.000 claims 1
- VFIAMRFRWFFWTA-UHFFFAOYSA-N [3-(4,6-dimethoxypyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound COC1=CC(OC)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 VFIAMRFRWFFWTA-UHFFFAOYSA-N 0.000 claims 1
- OFXUUYPFMNNTIU-UHFFFAOYSA-N [3-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-(2-phenylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 OFXUUYPFMNNTIU-UHFFFAOYSA-N 0.000 claims 1
- RUUBWSXPUVGENA-UHFFFAOYSA-N [3-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2)C=2SC=CC=2)=N1 RUUBWSXPUVGENA-UHFFFAOYSA-N 0.000 claims 1
- GWVNNSNIAOPTHK-UHFFFAOYSA-N [3-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-(5-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=C(F)C=2)C=2N=CC=CN=2)=N1 GWVNNSNIAOPTHK-UHFFFAOYSA-N 0.000 claims 1
- HXQRNACRFYBQKE-UHFFFAOYSA-N [3-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 HXQRNACRFYBQKE-UHFFFAOYSA-N 0.000 claims 1
- XZELEIIAULBWNR-UHFFFAOYSA-N [3-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 XZELEIIAULBWNR-UHFFFAOYSA-N 0.000 claims 1
- UDXTYHKJPIAMNH-UHFFFAOYSA-N [3-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2CC3N(CC3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 UDXTYHKJPIAMNH-UHFFFAOYSA-N 0.000 claims 1
- VHRBCQYXYFTSKC-UHFFFAOYSA-N [3-(4-methylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-(2-phenylphenyl)methanone Chemical compound CC1=CC=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 VHRBCQYXYFTSKC-UHFFFAOYSA-N 0.000 claims 1
- ULIIXYYYZPFWOG-UHFFFAOYSA-N [3-(4-methylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-6-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound CC1=CC=NC(N2CC3N(CC3C2)C(=O)C=2C(=CC=CC=2)C=2SC=CC=2)=N1 ULIIXYYYZPFWOG-UHFFFAOYSA-N 0.000 claims 1
- KLPFRSAEGIGZFZ-VQIMIIECSA-N [3-fluoro-2-(1,2-oxazol-5-yl)phenyl]-[(1r,6s)-4-(4,5,6-trimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound CC1=C(C)C(C)=NC(N2C[C@H]3N(C[C@H]3CC2)C(=O)C=2C(=C(F)C=CC=2)C=2ON=CC=2)=N1 KLPFRSAEGIGZFZ-VQIMIIECSA-N 0.000 claims 1
- LLRGSYGXXWURGI-CXAGYDPISA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1r,6s)-4-[4-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C=CC=C(C=2N2N=CC=N2)F)CN1C1=CC(C(F)(F)F)=CC=N1 LLRGSYGXXWURGI-CXAGYDPISA-N 0.000 claims 1
- DAYJKGFFLDEOFR-CZUORRHYSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1r,6s)-4-[6-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C=CC=C(C=2N2N=CC=N2)F)CN1C1=CC=CC(C(F)(F)F)=N1 DAYJKGFFLDEOFR-CZUORRHYSA-N 0.000 claims 1
- XOSYGJTXILGMNE-IUODEOHRSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1r,6s)-4-[6-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-7-yl]methanone Chemical compound C([C@@H]1CN([C@@H]1C1)C(=O)C=2C=CC=C(C=2N2N=CC=N2)F)CN1C1=CC(C(F)(F)F)=NC=N1 XOSYGJTXILGMNE-IUODEOHRSA-N 0.000 claims 1
- JCWXAQBOQLLUDY-UHFFFAOYSA-N [4-(1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-7-yl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C2CN(C=3OC4=CC=CC=C4N=3)CCC2C1 JCWXAQBOQLLUDY-UHFFFAOYSA-N 0.000 claims 1
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| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| RU2014136339A (ru) | 2012-02-07 | 2016-03-27 | Иолас Терапьютикс, Инк. | Замещенные пролины/пиперидины как антагонисты орексиновых рецепторов |
| PT2855453T (pt) | 2012-06-04 | 2017-03-09 | Actelion Pharmaceuticals Ltd | Derivados de benzimidazol-prolina |
| WO2014057435A1 (en) | 2012-10-10 | 2014-04-17 | Actelion Pharmaceuticals Ltd | Orexin receptor antagonists which are [ortho bi (hetero )aryl]-[2-(meta bi (hetero )aryl)-pyrrolidin-1-yl]-methanone derivatives |
| CN103012293A (zh) * | 2012-12-13 | 2013-04-03 | 同济大学 | 一种抗失眠药物mk-4305中间体的合成方法 |
| EP2970241A1 (en) | 2013-03-12 | 2016-01-20 | Actelion Pharmaceuticals Ltd. | Azetidine amide derivatives as orexin receptor antagonists |
| TW201444821A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代之哌啶化合物及其作為食慾素受體調節劑之用途 |
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| TW201444849A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代的7-氮雜雙環類及其作為食慾激素受體調節劑之用途 |
| TWI644671B (zh) | 2013-03-14 | 2018-12-21 | 比利時商健生藥品公司 | Ｐ２ｘ７調節劑 |
| EP3068783B1 (en) | 2013-11-15 | 2020-09-23 | The Board of Trustees of the Leland Stanford Junior University | Agonists of hypocretin receptor 2 for use for treating heart failure |
| UA116053C2 (uk) | 2013-12-04 | 2018-01-25 | Ідорсія Фармасьютікалз Лтд | Застосування похідних бензоімідазолу-проліну |
| EP3180332B1 (en) | 2014-08-13 | 2021-10-27 | Eolas Therapeutics Inc. | Difluoropyrrolidines as orexin receptor modulators |
| WO2016040789A1 (en) | 2014-09-11 | 2016-03-17 | Janssen Pharmaceutica Nv | Substituted 2-azabicycles and their use as orexin receptor modulators |
| US10196383B2 (en) | 2015-07-17 | 2019-02-05 | Sunshine Lake Pharma Co., Ltd. | Substituted quinazoline compounds and preparation and uses thereof |
| WO2017088759A1 (en) | 2015-11-23 | 2017-06-01 | Sunshine Lake Pharma Co., Ltd. | OCTAHYDROPYRROLO [3, 4-c] PYRROLE DERIVATIVES AND USES THEREOF |
| KR102738491B1 (ko) | 2016-02-12 | 2024-12-03 | 아스트라제네카 아베 | 오렉신 수용체 조정제로서의 할로-치환된 피페리딘 |
| RS63296B1 (sr) | 2016-03-10 | 2022-07-29 | Janssen Pharmaceutica Nv | Metode lečenja depresije korišćenjem antagonista receptora oreksin-2 |
| CA3059394C (en) | 2017-05-03 | 2023-09-12 | Idorsia Pharmaceuticals Ltd | Preparation of 2-([1,2,3]triazol-2-yl)-benzoic acid derivatives |
| WO2020065614A1 (en) | 2018-09-28 | 2020-04-02 | Janssen Pharmaceutica Nv | Monoacylglycerol lipase modulators |
| CN113164459B (zh) | 2018-09-28 | 2024-09-03 | 詹森药业有限公司 | 单酰基甘油脂肪酶调节剂 |
| ES2988132T3 (es) | 2018-11-14 | 2024-11-19 | Janssen Pharmaceutica Nv | Métodos sintéticos mejorados para fabricar compuestos heterocíclicos fusionados como moduladores del receptor de orexina |
| PE20220842A1 (es) | 2019-08-07 | 2022-05-24 | Janssen Pharmaceutica Nv | Metodos sinteticos mejorados para la elaboracion de compuestos de (2h-1,2,3-triazol-2-il)fenilo como moduladores del receptor de orexina |
| ES3037365T3 (en) | 2019-09-30 | 2025-10-01 | Janssen Pharmaceutica Nv | Radiolabelled mgl pet ligands |
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Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6375897B1 (en) | 2000-02-14 | 2002-04-23 | Ansys Technologies, Inc. | Urine collection cup |
| US6809105B2 (en) | 2000-04-27 | 2004-10-26 | Abbott Laboratories | Diazabicyclic central nervous system active agents |
| MY145722A (en) | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
| US7470710B2 (en) | 2001-06-28 | 2008-12-30 | Smithkline Beecham P.L.C. | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| GB2383315B (en) | 2001-12-18 | 2005-04-06 | Christopher Donald Clarke | Vehicle imaging system |
| GB0130341D0 (en) | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
| ES2278197T3 (es) | 2002-07-09 | 2007-08-01 | Actelion Pharmaceuticals Ltd. | Derivados de 7,8,9,10-tetrahidro-6h-azepino, 6,7,8,9-tetrahidro-pirido y 2,3-dihidro-2h-pirrolo(1,2-b)-quinazolinona. |
| WO2004033418A2 (en) | 2002-10-11 | 2004-04-22 | Actelion Pharmaceuticals Ltd. | Sulfonylamino-acetic derivatives and their use as orexin receptor antagonists |
| GB0225944D0 (en) | 2002-11-06 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
| US20040242641A1 (en) | 2003-05-27 | 2004-12-02 | Buckley Michael J. | (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent |
| US7399765B2 (en) | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
| US20050065178A1 (en) | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| CA2587141A1 (en) | 2004-11-24 | 2006-06-01 | Pfizer Inc. | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| DE102004061344A1 (de) | 2004-12-20 | 2006-07-06 | Siemens Ag | Verfahren zur sicheren Auslegung eines Systems, zugehörige Systemkomponente und Software |
| US20060258691A1 (en) | 2005-05-13 | 2006-11-16 | Joseph Barbosa | Methods and compositions for improving cognition |
| RU2007146444A (ru) | 2005-05-13 | 2009-06-20 | Лексикон Фармасьютикалз, Инк. (Us) | Полициклические соединения и способы их применения |
| GB0510204D0 (en) | 2005-05-19 | 2005-06-22 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| JP2009506061A (ja) * | 2005-08-26 | 2009-02-12 | メルク エンド カムパニー インコーポレーテッド | ジアザスピロデカンオレキシン受容体拮抗薬 |
| US20090105318A1 (en) | 2006-03-29 | 2009-04-23 | Coleman Paul J | Amidoethylthioether Orexin Receptor Antagonists |
| WO2007126935A2 (en) | 2006-03-29 | 2007-11-08 | Merck & Co., Inc. | Diazepan orexin receptor antagonists |
| AU2007272795A1 (en) | 2006-07-14 | 2008-01-17 | Merck & Co., Inc. | 2-substituted proline bis-amide orexin receptor antagonists |
| DK2049529T3 (da) | 2006-07-14 | 2010-11-29 | Merck Sharp & Dohme | Substituerede diazepan-orexin-receptor- antagonister |
| EP2049110B1 (en) | 2006-07-14 | 2014-08-20 | Merck Sharp & Dohme Corp. | Bridged diazepan orexin receptor antagonists |
| DE602007007497D1 (de) | 2006-09-18 | 2010-08-12 | Hoffmann La Roche | Octahydropyrroloä3,4-cüpyrrolderivate und ihre verwendung als antivirale mittel |
| EP2089018A2 (en) | 2006-11-07 | 2009-08-19 | Lexicon Pharmaceuticals, Inc. | Methods of treating cognitive impairment and dementia |
| PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| EP2150114A4 (en) | 2007-05-18 | 2012-01-18 | Merck Sharp & Dohme | OXO-BRIDGED DIAZEPANOREXINE RECEPTOR ANTAGONISTS |
| FR2918061B1 (fr) | 2007-06-28 | 2010-10-22 | Sanofi Aventis | Derives de 6-cycloamino-3-(pyridin-4-yl)imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique. |
| FR2918986B1 (fr) | 2007-07-19 | 2009-09-04 | Sanofi Aventis Sa | Derives de 6-cycloamino-3-(pyridazin-4-yl)imidazo[1,2-b]- pyridazine, leur preparation et leur application en therapeutique |
| ES2400830T3 (es) | 2007-08-15 | 2013-04-12 | Actelion Pharmaceuticals Ltd. | Derivados de 1,2-diamido-etileno como antagonistas de orexina |
| JP2011502146A (ja) | 2007-10-29 | 2011-01-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 置換ジアゼパンオレキシン受容体アンタゴニスト |
| EP2058001A1 (en) | 2007-11-08 | 2009-05-13 | Crossbeta Biosciences B.V. | Enhancement of immunogenicity of antigens |
| KR20100099742A (ko) | 2007-12-21 | 2010-09-13 | 아스트라제네카 아베 | 안드로겐 수용체 관련 병태의 치료에서 사용하기 위한 이환식 유도체 |
| WO2009080533A1 (en) | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heteroaryl derivatives as orexin receptor antagonists |
| GB0806536D0 (en) | 2008-04-10 | 2008-05-14 | Glaxo Group Ltd | Novel compounds |
| AR072899A1 (es) | 2008-08-07 | 2010-09-29 | Merck Sharp & Dohme | Derivados de terpiridina-carboxamida antagonistas de receptores de orexina, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento del insomnio y la obesidad. |
| US8093255B2 (en) | 2008-10-09 | 2012-01-10 | Glaxo Group Limited | Imidazo[1,2-A]pyrimidines as orexin receptor antagonists |
| US8129384B2 (en) | 2008-10-09 | 2012-03-06 | Glaxo Group Limited | Imidazo[1,2-a]pyrazines as orexin receptor antagonists |
| US8623863B2 (en) | 2008-10-21 | 2014-01-07 | Merck Sharp & Dohme Corp. | Disubstituted azepan orexin receptor antagonists |
| EP2349270B1 (en) | 2008-10-21 | 2015-09-09 | Merck Sharp & Dohme Corp. | 2,5-disubstituted morpholine orexin receptor antagonists |
| WO2010048014A1 (en) | 2008-10-21 | 2010-04-29 | Merck Sharp & Dohme Corp. | 2,4-disubstituted pyrrolidine orexin receptor antagonists |
| CA2739916A1 (en) | 2008-10-21 | 2010-04-29 | Merck Sharp & Dohme Corp. | 2,5-disubstituted piperidine orexin receptor antagonists |
| JP2012506374A (ja) | 2008-10-21 | 2012-03-15 | メルク・シャープ・エンド・ドーム・コーポレイション | ２，５−二置換ピペリジンオレキシン受容体アンタゴニスト |
| US8703770B2 (en) | 2008-10-30 | 2014-04-22 | Merck Sharp & Dohme Corp. | Pyridazine carboxamide orexin receptor antagonists |
| MX2011004551A (es) | 2008-10-30 | 2011-05-25 | Merck Sharp & Dohme | Antagonistas del receptor de orexina de isonicotinamida. |
| EP2349262B1 (en) | 2008-10-30 | 2014-06-25 | Merck Sharp & Dohme Corp. | 2,5-disubstituted phenyl carboxamide orexin receptor antagonists |
| WO2010060470A1 (en) | 2008-11-26 | 2010-06-03 | Glaxo Group Limited | Piperidine derivatives useful as orexin receptor antagonists |
| JP2012509912A (ja) | 2008-11-26 | 2012-04-26 | グラクソ グループ リミテッド | 新規の化合物 |
| JP2012509911A (ja) | 2008-11-26 | 2012-04-26 | グラクソ グループ リミテッド | 新規の化合物 |
| AU2009324238A1 (en) | 2008-12-02 | 2010-06-10 | Glaxo Group Limited | N-{[(IR,4S,6R-3-(2-pyridinylcarbonyl)-3-azabicyclo [4.1.0] hept-4-yl] methyl}-2-heteroarylamine derivatives and uses thereof |
| AU2009324239A1 (en) | 2008-12-02 | 2010-06-10 | Glaxo Group Limited | N-{[(IR,4S,6R-3-(2-pyridinylcarbonyl)-3-azabicyclo [4.1.0]hept-4-yl] methyl}-2-heteroarylamine derivatives and uses thereof |
| GB0823467D0 (en) | 2008-12-23 | 2009-01-28 | Glaxo Group Ltd | Novel Compounds |
| WO2011050202A1 (en) * | 2009-10-23 | 2011-04-28 | Janssen Pharmaceutica Nv | Fused heterocyclic compounds as orexin receptor modulators |
-
2010
- 2010-10-21 WO PCT/US2010/053611 patent/WO2011050202A1/en not_active Ceased
- 2010-10-21 US US13/503,298 patent/US9062044B2/en active Active
- 2010-10-21 JP JP2012535386A patent/JP5848251B2/ja not_active Expired - Fee Related
- 2010-10-21 EP EP10773478.2A patent/EP2491031B1/en active Active
- 2010-10-22 CL CL2010001160A patent/CL2010001160A1/es unknown
- 2010-10-22 AR ARP100103875A patent/AR078732A1/es unknown
- 2010-10-22 PE PE2010000998A patent/PE20110328A1/es not_active Application Discontinuation
- 2010-10-22 TW TW099136021A patent/TW201141859A/zh unknown
- 2010-10-25 UY UY0001032967A patent/UY32967A/es not_active Application Discontinuation
-
2015
- 2015-11-26 JP JP2015230474A patent/JP6170121B2/ja not_active Expired - Fee Related
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