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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| 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. |
| US8129384B2 (en) | 2008-10-09 | 2012-03-06 | Glaxo Group Limited | Imidazo[1,2-a]pyrazines as orexin receptor antagonists |
| US8093255B2 (en) | 2008-10-09 | 2012-01-10 | Glaxo Group Limited | Imidazo[1,2-A]pyrimidines as orexin receptor antagonists |
| US8710076B2 (en) | 2008-10-21 | 2014-04-29 | Merck Sharp & Dohme Corp. | 2,5-disubstituted piperidine orexin receptor antagonists |
| EP2349270B1 (en) | 2008-10-21 | 2015-09-09 | Merck Sharp & Dohme Corp. | 2,5-disubstituted morpholine 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 |
| EP2348846B1 (en) | 2008-10-21 | 2013-08-28 | Merck Sharp & Dohme Corp. | Disubstituted azepan orexin receptor antagonists |
| WO2010048014A1 (en) | 2008-10-21 | 2010-04-29 | Merck Sharp & Dohme Corp. | 2,4-disubstituted pyrrolidine orexin receptor antagonists |
| MX2011004551A (es) | 2008-10-30 | 2011-05-25 | Merck Sharp & Dohme | Antagonistas del receptor de orexina de isonicotinamida. |
| US8399494B2 (en) | 2008-10-30 | 2013-03-19 | Merck Sharp & Dohme Corp. | 2,5-disubstituted phenyl carboxamide orexin receptor antagonists |
| AU2009308982A1 (en) | 2008-10-30 | 2010-05-06 | Merck Sharp & Dohme Corp. | Pyridazine carboxamide orexin receptor antagonists |
| WO2010060471A1 (en) | 2008-11-26 | 2010-06-03 | Glaxo Group Limited | Piperidine derivatives useful as orexin receptor antagonists |
| WO2010060470A1 (en) | 2008-11-26 | 2010-06-03 | Glaxo Group Limited | Piperidine derivatives useful as orexin receptor antagonists |
| EP2358713A1 (en) | 2008-11-26 | 2011-08-24 | Glaxo Group Limited | Imidazopyridazine derivatives acting as orexin antagonists |
| US20100144760A1 (en) | 2008-12-02 | 2010-06-10 | Giuseppe Alvaro | Novel compounds |
| 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 |
| 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 EP EP10773478.2A patent/EP2491031B1/en active Active
- 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
- 2010-10-22 TW TW099136021A patent/TW201141859A/zh unknown
- 2010-10-22 AR ARP100103875A patent/AR078732A1/es unknown
- 2010-10-22 CL CL2010001160A patent/CL2010001160A1/es unknown
- 2010-10-22 PE PE2010000998A patent/PE20110328A1/es not_active Application Discontinuation
- 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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