JP2016501240A5 - - Google Patents
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- JP2016501240A5 JP2016501240A5 JP2015545757A JP2015545757A JP2016501240A5 JP 2016501240 A5 JP2016501240 A5 JP 2016501240A5 JP 2015545757 A JP2015545757 A JP 2015545757A JP 2015545757 A JP2015545757 A JP 2015545757A JP 2016501240 A5 JP2016501240 A5 JP 2016501240A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridine
- cyclopropylmethoxy
- amide
- carboxylic acid
- amino
- 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 oxanylalkoxy Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims 6
- XBIFXIZBKZGCDC-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxylic acid Chemical compound C1CC1COC1=NC(C(=O)O)=CC=C1N1CC(F)(F)C1 XBIFXIZBKZGCDC-UHFFFAOYSA-N 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000001408 amides Chemical class 0.000 claims 5
- 206010016654 Fibrosis Diseases 0.000 claims 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- RJFPQEQTAJLPSJ-UHFFFAOYSA-N n-(3-amino-1-cyclohexyl-3-oxopropyl)-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CCCCC1C(CC(=O)N)NC(=O)C(N=C1OCC2CC2)=CC=C1C1CC1 RJFPQEQTAJLPSJ-UHFFFAOYSA-N 0.000 claims 3
- MEFUGYYDDPAFDH-UHFFFAOYSA-N n-(3-amino-1-cyclopropyl-3-oxopropyl)-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1C(CC(=O)N)NC(=O)C(N=C1OCC2CC2)=CC=C1C1CC1 MEFUGYYDDPAFDH-UHFFFAOYSA-N 0.000 claims 3
- GDGZHIWKCMGJAG-UHFFFAOYSA-N n-[1-(2-amino-2-oxoethyl)cyclobutyl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCC1 GDGZHIWKCMGJAG-UHFFFAOYSA-N 0.000 claims 3
- VKZXWJSWOPPLFH-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxolan-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCOC1 VKZXWJSWOPPLFH-UHFFFAOYSA-N 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 208000007788 Acute Liver Failure Diseases 0.000 claims 2
- 206010000804 Acute hepatic failure Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000031229 Cardiomyopathies Diseases 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 208000008069 Geographic Atrophy Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 206010051920 Glomerulonephropathy Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000002260 Keloid Diseases 0.000 claims 2
- 206010023330 Keloid scar Diseases 0.000 claims 2
- AIWBUXBRYDGMTO-JKSUJKDBSA-N N-[(1R,2S)-2-carbamoylcyclohexyl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound NC(=O)[C@H]1CCCC[C@H]1NC(=O)c1ccc(C2CC2)c(OCC2CC2)n1 AIWBUXBRYDGMTO-JKSUJKDBSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010069385 Ocular ischaemic syndrome Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 206010038933 Retinopathy of prematurity Diseases 0.000 claims 2
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 2
- 206010042953 Systemic sclerosis Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 231100000836 acute liver failure Toxicity 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- ULQNXMPOHCDCLP-UHFFFAOYSA-N ethyl 3-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(CC(=O)OCC)NC(=O)C(N=C1OCC2CC2)=CC=C1N1CC(F)(F)C1 ULQNXMPOHCDCLP-UHFFFAOYSA-N 0.000 claims 2
- 230000004761 fibrosis Effects 0.000 claims 2
- 208000007565 gingivitis Diseases 0.000 claims 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000005059 halophenyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims 2
- 230000001969 hypertrophic effect Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 210000001117 keloid Anatomy 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- RUUCEDXZNARXOO-UHFFFAOYSA-N n-(1-amino-1-oxoheptan-3-yl)-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)NC(CC(N)=O)CCCC)=CC=C1C1CC1 RUUCEDXZNARXOO-UHFFFAOYSA-N 0.000 claims 2
- YEGUINSKITWAPR-UHFFFAOYSA-N n-(1-amino-5-methyl-1-oxohexan-3-yl)-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)NC(CC(N)=O)CC(C)C)=CC=C1C1CC1 YEGUINSKITWAPR-UHFFFAOYSA-N 0.000 claims 2
- NYVIPUKWWICLDA-UHFFFAOYSA-N n-(4-amino-1,1,1-trifluoro-4-oxobutan-2-yl)-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)NC(CC(=O)N)C(F)(F)F)=CC=C1C1CC1 NYVIPUKWWICLDA-UHFFFAOYSA-N 0.000 claims 2
- ITVAFLXNSQAPPE-UHFFFAOYSA-N n-(4-amino-1,1,1-trifluoro-4-oxobutan-2-yl)-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)NC(CC(=O)N)C(F)(F)F)=CC=C1N1CC(F)(F)C1 ITVAFLXNSQAPPE-UHFFFAOYSA-N 0.000 claims 2
- KKXJEVRJTMPOIV-UHFFFAOYSA-N n-(4-amino-2-methyl-4-oxobutan-2-yl)-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)NC(C)(CC(N)=O)C)=CC=C1N1CC(F)(F)C1 KKXJEVRJTMPOIV-UHFFFAOYSA-N 0.000 claims 2
- WZYWZJBPRBZKFR-UONOGXRCSA-N n-[(1r,2s)-2-carbamoylcyclohexyl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound NC(=O)[C@H]1CCCC[C@H]1NC(=O)C(N=C1OCC2CC2)=CC=C1N1CC(F)(F)C1 WZYWZJBPRBZKFR-UONOGXRCSA-N 0.000 claims 2
- OMXHNXHSWWODTI-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CS(=O)(=O)C1 OMXHNXHSWWODTI-UHFFFAOYSA-N 0.000 claims 2
- HKUBPJATXVFEBI-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-6-(oxolan-2-ylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2OCCC2)=NC=1C(=O)NC1(CC(=O)N)CS(=O)(=O)C1 HKUBPJATXVFEBI-UHFFFAOYSA-N 0.000 claims 2
- BHXDCIAWZJHAND-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-6-(cyclopropylmethoxy)-5-(1-hydroxycyclobutyl)pyridine-2-carboxamide Chemical compound C=1C=C(C2(O)CCC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CS(=O)(=O)C1 BHXDCIAWZJHAND-UHFFFAOYSA-N 0.000 claims 2
- QETWDAHVHZFSHK-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CS(=O)(=O)C1 QETWDAHVHZFSHK-UHFFFAOYSA-N 0.000 claims 2
- OHPQSVQELCZOCS-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)azetidin-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CNC1 OHPQSVQELCZOCS-UHFFFAOYSA-N 0.000 claims 2
- OPHBSQRNATYTEN-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-5-cyclopropyl-6-(2,2,3,3,3-pentafluoropropoxy)pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC(F)(F)C(F)(F)F)=NC=1C(=O)NC1(CC(=O)N)COC1 OPHBSQRNATYTEN-UHFFFAOYSA-N 0.000 claims 2
- JUZOJWJEILOEFD-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)COC1 JUZOJWJEILOEFD-UHFFFAOYSA-N 0.000 claims 2
- VWDRVCVNSCYAFX-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)COC1 VWDRVCVNSCYAFX-UHFFFAOYSA-N 0.000 claims 2
- KGYKANRITXXAGL-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)pyrrolidin-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCNC1 KGYKANRITXXAGL-UHFFFAOYSA-N 0.000 claims 2
- CJENIGFJMKXURX-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)thietan-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CSC1 CJENIGFJMKXURX-UHFFFAOYSA-N 0.000 claims 2
- NAUSXSDYQDNOSP-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)thietan-3-yl]-6-(cyclopropylmethoxy)-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C=1C=C(C(F)(F)F)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CSC1 NAUSXSDYQDNOSP-UHFFFAOYSA-N 0.000 claims 2
- DPNBUBHZDLIKSZ-UHFFFAOYSA-N n-[3-amino-1-(oxan-4-yl)-3-oxopropyl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1COCCC1C(CC(=O)N)NC(=O)C(N=C1OCC2CC2)=CC=C1C1CC1 DPNBUBHZDLIKSZ-UHFFFAOYSA-N 0.000 claims 2
- OBMRNEJLBJQKKS-UHFFFAOYSA-N n-[4-(2-amino-2-oxoethyl)-1,1-dioxothian-4-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCS(=O)(=O)CC1 OBMRNEJLBJQKKS-UHFFFAOYSA-N 0.000 claims 2
- DVEGWZSDFANSEC-UHFFFAOYSA-N n-[4-(2-amino-2-oxoethyl)piperidin-4-yl]-5-cyclopropyl-6-[(4-fluorophenyl)methyl]pyridine-2-carboxamide;hydrochloride Chemical compound Cl.C=1C=C(C2CC2)C(CC=2C=CC(F)=CC=2)=NC=1C(=O)NC1(CC(=O)N)CCNCC1 DVEGWZSDFANSEC-UHFFFAOYSA-N 0.000 claims 2
- WEBIPWRCFXHPRG-UHFFFAOYSA-N n-[4-(2-amino-2-oxoethyl)piperidin-4-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCNCC1 WEBIPWRCFXHPRG-UHFFFAOYSA-N 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000005475 oxolanyl group Chemical group 0.000 claims 2
- 230000010412 perfusion Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 201000002793 renal fibrosis Diseases 0.000 claims 2
- 208000004644 retinal vein occlusion Diseases 0.000 claims 2
- 231100000241 scar Toxicity 0.000 claims 2
- 230000009885 systemic effect Effects 0.000 claims 2
- 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 claims 2
- 125000002053 thietanyl group Chemical group 0.000 claims 2
- 230000001052 transient effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- BJQCHHZCXNQQLO-UHFFFAOYSA-N 2-[1-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]cyclobutyl]acetic acid Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)O)CCC1 BJQCHHZCXNQQLO-UHFFFAOYSA-N 0.000 claims 1
- UNTTUPYHWXJEOZ-UHFFFAOYSA-N 2-[3-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]-1,1-dioxothietan-3-yl]acetic acid Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)O)CS(=O)(=O)C1 UNTTUPYHWXJEOZ-UHFFFAOYSA-N 0.000 claims 1
- MXHXRSAORMTNAA-UHFFFAOYSA-N 2-[4-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]oxan-4-yl]acetic acid Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)O)CCOCC1 MXHXRSAORMTNAA-UHFFFAOYSA-N 0.000 claims 1
- XGWVSIJTDZNDES-UHFFFAOYSA-N 2-[[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]methyl]-4-methylpentanoic acid Chemical compound C1CC1COC1=NC(C(=O)NCC(CC(C)C)C(O)=O)=CC=C1N1CC(F)(F)C1 XGWVSIJTDZNDES-UHFFFAOYSA-N 0.000 claims 1
- VYJVVPMCRWSCIJ-UHFFFAOYSA-N 5-cyclopropyl-6-(cyclopropylmethoxy)-n-[3-[2-(dimethylamino)-2-oxoethyl]oxetan-3-yl]pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N(C)C)COC1 VYJVVPMCRWSCIJ-UHFFFAOYSA-N 0.000 claims 1
- GUBZREBIEPAYBB-UHFFFAOYSA-N 5-cyclopropyl-6-(cyclopropylmethoxy)-n-[3-[2-(methylamino)-2-oxoethyl]oxetan-3-yl]pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)NC)COC1 GUBZREBIEPAYBB-UHFFFAOYSA-N 0.000 claims 1
- JPKWMNNAPKYWNH-UHFFFAOYSA-N 5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxylic acid Chemical compound C1CC1COC1=NC(C(=O)O)=CC=C1C1CC1 JPKWMNNAPKYWNH-UHFFFAOYSA-N 0.000 claims 1
- QMJXTQGAOJVGOF-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-n-(1-methyl-5-oxopyrrolidin-3-yl)pyridine-2-carboxamide Chemical compound C1C(=O)N(C)CC1NC(=O)C(N=C1OCC2CC2)=CC=C1N1CC(F)(F)C1 QMJXTQGAOJVGOF-UHFFFAOYSA-N 0.000 claims 1
- KTUOGFSNWGPPCZ-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-n-[1-(methylamino)-1-oxo-5-phenylpentan-3-yl]pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC(CC(=O)NC)CCC1=CC=CC=C1 KTUOGFSNWGPPCZ-UHFFFAOYSA-N 0.000 claims 1
- HPFMLZKVZXECAR-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-n-[1-(methylamino)-1-oxooctan-3-yl]pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)NC(CC(=O)NC)CCCCC)=CC=C1N1CC(F)(F)C1 HPFMLZKVZXECAR-UHFFFAOYSA-N 0.000 claims 1
- LPIOARKUUNUKMT-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-n-[2-methyl-4-(methylamino)-4-oxobutan-2-yl]pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)NC(C)(C)CC(=O)NC)=CC=C1N1CC(F)(F)C1 LPIOARKUUNUKMT-UHFFFAOYSA-N 0.000 claims 1
- TYIUIRJZAOKTNM-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-n-[3-[2-(dimethylamino)-2-oxoethyl]oxetan-3-yl]pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N(C)C)COC1 TYIUIRJZAOKTNM-UHFFFAOYSA-N 0.000 claims 1
- NPVJSXVKTDEMPP-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)-n-[3-[2-(methylamino)-2-oxoethyl]oxetan-3-yl]pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)NC)COC1 NPVJSXVKTDEMPP-UHFFFAOYSA-N 0.000 claims 1
- LCMLUQOKSCVTNT-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-n-[3-[2-(dimethylamino)-2-oxoethyl]oxetan-3-yl]-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C=1C=C(C(F)(F)F)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N(C)C)COC1 LCMLUQOKSCVTNT-UHFFFAOYSA-N 0.000 claims 1
- FTABBYLGXFXPFZ-UHFFFAOYSA-N 6-(cyclopropylmethoxy)-n-[3-[2-(methylamino)-2-oxoethyl]oxetan-3-yl]-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C=1C=C(C(F)(F)F)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)NC)COC1 FTABBYLGXFXPFZ-UHFFFAOYSA-N 0.000 claims 1
- YERSNKQZCVVVPY-UHFFFAOYSA-N C(N)(=O)CC1(CS(CC1)(=O)=O)NC(=O)C1=NC(=C(C=C1)N1CC(C1)(F)F)OCC1CC1 Chemical compound C(N)(=O)CC1(CS(CC1)(=O)=O)NC(=O)C1=NC(=C(C=C1)N1CC(C1)(F)F)OCC1CC1 YERSNKQZCVVVPY-UHFFFAOYSA-N 0.000 claims 1
- 206010010356 Congenital anomaly Diseases 0.000 claims 1
- JKWKFTPYJREQSH-UHFFFAOYSA-N NC(=O)CC1(CCCNC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 Chemical compound NC(=O)CC1(CCCNC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 JKWKFTPYJREQSH-UHFFFAOYSA-N 0.000 claims 1
- NPZMSRBPXBKREJ-UHFFFAOYSA-N NC(=O)CC1(CCCOC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 Chemical compound NC(=O)CC1(CCCOC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 NPZMSRBPXBKREJ-UHFFFAOYSA-N 0.000 claims 1
- TXBIASGINDWLIJ-UHFFFAOYSA-N NC(=O)CC1(CCCS(=O)(=O)C1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 Chemical compound NC(=O)CC1(CCCS(=O)(=O)C1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 TXBIASGINDWLIJ-UHFFFAOYSA-N 0.000 claims 1
- LLHQEWZFCARAGZ-UHFFFAOYSA-N NC(=O)CC1(CCNS(=O)(=O)C1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 Chemical compound NC(=O)CC1(CCNS(=O)(=O)C1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 LLHQEWZFCARAGZ-UHFFFAOYSA-N 0.000 claims 1
- WHFJEGNQJTVSSS-UHFFFAOYSA-N NC(=O)CC1(CCS(=O)(=O)NC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 Chemical compound NC(=O)CC1(CCS(=O)(=O)NC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 WHFJEGNQJTVSSS-UHFFFAOYSA-N 0.000 claims 1
- AVZPASQWVZLMCC-UHFFFAOYSA-N NC(=O)CC1(CCSC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 Chemical compound NC(=O)CC1(CCSC1)NC(=O)c1ccc(N2CC(F)(F)C2)c(OCC2CC2)n1 AVZPASQWVZLMCC-UHFFFAOYSA-N 0.000 claims 1
- AIWBUXBRYDGMTO-HZPDHXFCSA-N NC(=O)[C@@H]1CCCC[C@H]1NC(=O)c1ccc(C2CC2)c(OCC2CC2)n1 Chemical compound NC(=O)[C@@H]1CCCC[C@H]1NC(=O)c1ccc(C2CC2)c(OCC2CC2)n1 AIWBUXBRYDGMTO-HZPDHXFCSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- PJVWIRBYDQLUNG-UHFFFAOYSA-N benzyl 3-(2-amino-2-oxoethyl)-3-[[5-cyclopropyl-6-[(4-fluorophenyl)methyl]pyridine-2-carbonyl]amino]azetidine-1-carboxylate Chemical compound C1C(CC(=O)N)(NC(=O)C=2N=C(CC=3C=CC(F)=CC=3)C(C3CC3)=CC=2)CN1C(=O)OCC1=CC=CC=C1 PJVWIRBYDQLUNG-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- DRHVVRSXQKWRLY-UHFFFAOYSA-N ethyl 2-[3-[[5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carbonyl]amino]oxetan-3-yl]acetate Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)OCC)COC1 DRHVVRSXQKWRLY-UHFFFAOYSA-N 0.000 claims 1
- SUQMDOFGSQCRFG-UHFFFAOYSA-N ethyl 2-[3-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]-1,1-dioxothietan-3-yl]acetate Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)OCC)CS(=O)(=O)C1 SUQMDOFGSQCRFG-UHFFFAOYSA-N 0.000 claims 1
- RJASHWCIINMVAD-UHFFFAOYSA-N ethyl 3-[[5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carbonyl]amino]-5-methylhexanoate Chemical compound C1CC1COC1=NC(C(=O)NC(CC(C)C)CC(=O)OCC)=CC=C1C1CC1 RJASHWCIINMVAD-UHFFFAOYSA-N 0.000 claims 1
- UNQRHGWHJJTKHX-UHFFFAOYSA-N ethyl 3-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]-3-methylbutanoate Chemical compound C1CC1COC1=NC(C(=O)NC(C)(C)CC(=O)OCC)=CC=C1N1CC(F)(F)C1 UNQRHGWHJJTKHX-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- FIQOZEPHPUNFMD-UHFFFAOYSA-N methyl 2-[4-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]oxan-4-yl]acetate Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)OC)CCOCC1 FIQOZEPHPUNFMD-UHFFFAOYSA-N 0.000 claims 1
- DWIKTISJNINHMA-LJQANCHMSA-N n-[(1r)-3-amino-1-(3-chlorophenyl)-3-oxopropyl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound N([C@H](CC(=O)N)C=1C=C(Cl)C=CC=1)C(=O)C(N=C1OCC2CC2)=CC=C1C1CC1 DWIKTISJNINHMA-LJQANCHMSA-N 0.000 claims 1
- GYYJEEMEJSFPMF-INIZCTEOSA-N n-[(1s)-3-amino-1-(oxan-4-yl)-3-oxopropyl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound N([C@@H](CC(=O)N)C1CCOCC1)C(=O)C(N=C1OCC2CC2)=CC=C1N1CC(F)(F)C1 GYYJEEMEJSFPMF-INIZCTEOSA-N 0.000 claims 1
- AIWBUXBRYDGMTO-CVEARBPZSA-N n-[(1s,2r)-2-carbamoylcyclohexyl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound NC(=O)[C@@H]1CCCC[C@@H]1NC(=O)C(N=C1OCC2CC2)=CC=C1C1CC1 AIWBUXBRYDGMTO-CVEARBPZSA-N 0.000 claims 1
- NAVWGHGDVWLJOD-MRXNPFEDSA-N n-[(3r)-1-amino-4,4-dimethyl-1-oxopentan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)N[C@H](CC(N)=O)C(C)(C)C)=CC=C1C1CC1 NAVWGHGDVWLJOD-MRXNPFEDSA-N 0.000 claims 1
- GHIMVTXYTVDAKS-MRXNPFEDSA-N n-[(3r)-1-amino-4-methyl-1-oxopentan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)N[C@H](CC(N)=O)C(C)C)=CC=C1C1CC1 GHIMVTXYTVDAKS-MRXNPFEDSA-N 0.000 claims 1
- NAVWGHGDVWLJOD-INIZCTEOSA-N n-[(3s)-1-amino-4,4-dimethyl-1-oxopentan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)N[C@@H](CC(N)=O)C(C)(C)C)=CC=C1C1CC1 NAVWGHGDVWLJOD-INIZCTEOSA-N 0.000 claims 1
- GHIMVTXYTVDAKS-INIZCTEOSA-N n-[(3s)-1-amino-4-methyl-1-oxopentan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)N[C@@H](CC(N)=O)C(C)C)=CC=C1C1CC1 GHIMVTXYTVDAKS-INIZCTEOSA-N 0.000 claims 1
- LPGZNVWDDMFMBB-AWEZNQCLSA-N n-[(3s)-1-amino-4-methyl-1-oxopentan-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C1CC1COC1=NC(C(=O)N[C@@H](CC(N)=O)C(C)C)=CC=C1N1CC(F)(F)C1 LPGZNVWDDMFMBB-AWEZNQCLSA-N 0.000 claims 1
- RKEGUPGSLASPQV-UHFFFAOYSA-N n-[1-(2-amino-2-oxoethyl)-3,3-difluorocyclobutyl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CC(F)(F)C1 RKEGUPGSLASPQV-UHFFFAOYSA-N 0.000 claims 1
- MIXVNRBJTCUSOX-UHFFFAOYSA-N n-[1-acetyl-3-(2-amino-2-oxoethyl)azetidin-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C1N(C(=O)C)CC1(CC(N)=O)NC(=O)C(N=C1OCC2CC2)=CC=C1N1CC(F)(F)C1 MIXVNRBJTCUSOX-UHFFFAOYSA-N 0.000 claims 1
- XSWSVFHQCZSDPR-UHFFFAOYSA-N n-[1-acetyl-4-(2-amino-2-oxoethyl)piperidin-4-yl]-5-cyclopropyl-6-[(4-fluorophenyl)methyl]pyridine-2-carboxamide Chemical compound C1CN(C(=O)C)CCC1(CC(N)=O)NC(=O)C(N=C1CC=2C=CC(F)=CC=2)=CC=C1C1CC1 XSWSVFHQCZSDPR-UHFFFAOYSA-N 0.000 claims 1
- FRFNJAPOKUGIRN-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-6-(2-methylpropylsulfanyl)pyridine-2-carboxamide Chemical compound CC(C)CSC1=NC(C(=O)NC2(CC(N)=O)CS(=O)(=O)C2)=CC=C1C1CC1 FRFNJAPOKUGIRN-UHFFFAOYSA-N 0.000 claims 1
- BAGYVUOKBZQDNO-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-5-cyclopropyl-6-[(4-fluorophenyl)methyl]pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(CC=2C=CC(F)=CC=2)=NC=1C(=O)NC1(CC(=O)N)CS(=O)(=O)C1 BAGYVUOKBZQDNO-UHFFFAOYSA-N 0.000 claims 1
- BELHZNFDLAQKHV-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-6-(3-chloro-4-fluorophenyl)pyridine-2-carboxamide Chemical compound C=1C=CC(C=2C=C(Cl)C(F)=CC=2)=NC=1C(=O)NC1(CC(=O)N)CS(=O)(=O)C1 BELHZNFDLAQKHV-UHFFFAOYSA-N 0.000 claims 1
- WZAOVQPGFNHOJZ-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-1,1-dioxothietan-3-yl]-6-(oxan-4-ylmethoxy)-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C=1C=C(C(F)(F)F)C(OCC2CCOCC2)=NC=1C(=O)NC1(CC(=O)N)CS(=O)(=O)C1 WZAOVQPGFNHOJZ-UHFFFAOYSA-N 0.000 claims 1
- OQNYOBMLJMECIQ-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-5-oxopyrrolidin-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CNC(=O)C1 OQNYOBMLJMECIQ-UHFFFAOYSA-N 0.000 claims 1
- OILCIVFGPUEDQO-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)-6-oxopiperidin-3-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCC(=O)NC1 OILCIVFGPUEDQO-UHFFFAOYSA-N 0.000 claims 1
- JAVOGQONDUIWBS-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)azetidin-3-yl]-5-cyclopropyl-6-[(4-fluorophenyl)methyl]pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(CC=2C=CC(F)=CC=2)=NC=1C(=O)NC1(CC(=O)N)CNC1 JAVOGQONDUIWBS-UHFFFAOYSA-N 0.000 claims 1
- RFFDVCSKYYONHV-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-5-bromo-6-propan-2-ylsulfinylpyridine-2-carboxamide Chemical compound C1=C(Br)C(S(=O)C(C)C)=NC(C(=O)NC2(CC(N)=O)COC2)=C1 RFFDVCSKYYONHV-UHFFFAOYSA-N 0.000 claims 1
- HUUIRDBMDQDXPS-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-5-cyclopropyl-6-(1,1,1-trifluoropropan-2-yloxy)pyridine-2-carboxamide Chemical compound FC(F)(F)C(C)OC1=NC(C(=O)NC2(CC(N)=O)COC2)=CC=C1C1CC1 HUUIRDBMDQDXPS-UHFFFAOYSA-N 0.000 claims 1
- VNOGZGIBPZGNHM-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-5-cyclopropyl-6-(2-methylpropylsulfonyl)pyridine-2-carboxamide Chemical compound CC(C)CS(=O)(=O)C1=NC(C(=O)NC2(CC(N)=O)COC2)=CC=C1C1CC1 VNOGZGIBPZGNHM-UHFFFAOYSA-N 0.000 claims 1
- LWBOSJUTCHPBQH-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-6-(cyclopropylmethoxy)-5-(1-fluorocyclobutyl)pyridine-2-carboxamide Chemical compound C=1C=C(C2(F)CCC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)COC1 LWBOSJUTCHPBQH-UHFFFAOYSA-N 0.000 claims 1
- QLDLOCORCJTTSJ-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-6-(cyclopropylmethoxy)-5-(1-hydroxycyclobutyl)pyridine-2-carboxamide Chemical compound C=1C=C(C2(O)CCC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)COC1 QLDLOCORCJTTSJ-UHFFFAOYSA-N 0.000 claims 1
- LIVVTVZKMBHXDI-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-6-(cyclopropylmethoxy)-5-(trifluoromethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(OC(F)(F)F)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)COC1 LIVVTVZKMBHXDI-UHFFFAOYSA-N 0.000 claims 1
- BEKJMTNABVDZDG-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxetan-3-yl]-6-chloro-5-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(OCC2CC2)C(Cl)=NC=1C(=O)NC1(CC(=O)N)COC1 BEKJMTNABVDZDG-UHFFFAOYSA-N 0.000 claims 1
- STVPDYWZHDNCNB-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxolan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCOC1 STVPDYWZHDNCNB-UHFFFAOYSA-N 0.000 claims 1
- AJIKZDYWFXRZEW-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)oxolan-3-yl]-5-cyclopropyl-6-[(4-fluorophenyl)methyl]pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(CC=2C=CC(F)=CC=2)=NC=1C(=O)NC1(CC(=O)N)CCOC1 AJIKZDYWFXRZEW-UHFFFAOYSA-N 0.000 claims 1
- RBMAPBCAHIYVGD-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)thietan-3-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CSC1 RBMAPBCAHIYVGD-UHFFFAOYSA-N 0.000 claims 1
- GDMPFDPVDVOJSG-UHFFFAOYSA-N n-[3-(2-amino-2-oxoethyl)thietan-3-yl]-6-(cyclopropylmethoxy)-5-(1-hydroxycyclobutyl)pyridine-2-carboxamide Chemical compound C=1C=C(C2(O)CCC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CSC1 GDMPFDPVDVOJSG-UHFFFAOYSA-N 0.000 claims 1
- GYYJEEMEJSFPMF-UHFFFAOYSA-N n-[3-amino-1-(oxan-4-yl)-3-oxopropyl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C1COCCC1C(CC(=O)N)NC(=O)C(N=C1OCC2CC2)=CC=C1N1CC(F)(F)C1 GYYJEEMEJSFPMF-UHFFFAOYSA-N 0.000 claims 1
- KXZSKOBQQVUGOY-UHFFFAOYSA-N n-[3-amino-3-oxo-1-(oxolan-3-yl)propyl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C1COCC1C(CC(=O)N)NC(=O)C(N=C1OCC2CC2)=CC=C1C1CC1 KXZSKOBQQVUGOY-UHFFFAOYSA-N 0.000 claims 1
- XHMHPKDJLRTWFZ-UHFFFAOYSA-N n-[3-amino-3-oxo-1-(oxolan-3-yl)propyl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C1COCC1C(CC(=O)N)NC(=O)C(N=C1OCC2CC2)=CC=C1N1CC(F)(F)C1 XHMHPKDJLRTWFZ-UHFFFAOYSA-N 0.000 claims 1
- QUXMYBKHKFFWSQ-UHFFFAOYSA-N n-[4-(2-amino-2-oxoethyl)-2-oxopiperidin-4-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCNC(=O)C1 QUXMYBKHKFFWSQ-UHFFFAOYSA-N 0.000 claims 1
- ARZZJNIMXKTWAW-UHFFFAOYSA-N n-[4-(2-amino-2-oxoethyl)oxan-4-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCOCC1 ARZZJNIMXKTWAW-UHFFFAOYSA-N 0.000 claims 1
- ZVUWJOWNWZGZHC-UHFFFAOYSA-N n-[4-(2-amino-2-oxoethyl)piperidin-4-yl]-5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carboxamide Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCNCC1 ZVUWJOWNWZGZHC-UHFFFAOYSA-N 0.000 claims 1
- YRSQEAJIQUWFEK-UHFFFAOYSA-N n-[4-(2-amino-2-oxoethyl)thian-4-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CCSCC1 YRSQEAJIQUWFEK-UHFFFAOYSA-N 0.000 claims 1
- UYUYCOPNGHJMCR-UHFFFAOYSA-N n-[5-(2-amino-2-oxoethyl)-2-oxo-1,3-diazinan-5-yl]-6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carboxamide Chemical compound C=1C=C(N2CC(F)(F)C2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)N)CNC(=O)NC1 UYUYCOPNGHJMCR-UHFFFAOYSA-N 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000002269 spontaneous effect Effects 0.000 claims 1
- XQKKWPNUPQVNQK-UHFFFAOYSA-N tert-butyl 3-[[6-(cyclopropylmethoxy)-5-(3,3-difluoroazetidin-1-yl)pyridine-2-carbonyl]amino]-5-methylhexanoate Chemical compound C1CC1COC1=NC(C(=O)NC(CC(=O)OC(C)(C)C)CC(C)C)=CC=C1N1CC(F)(F)C1 XQKKWPNUPQVNQK-UHFFFAOYSA-N 0.000 claims 1
- UFJIURKENRZQJI-UHFFFAOYSA-N tert-butyl 4-[[5-cyclopropyl-6-(cyclopropylmethoxy)pyridine-2-carbonyl]amino]-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate Chemical compound C=1C=C(C2CC2)C(OCC2CC2)=NC=1C(=O)NC1(CC(=O)OC)CCN(C(=O)OC(C)(C)C)CC1 UFJIURKENRZQJI-UHFFFAOYSA-N 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
- 0 *c(cc1)c(*)nc1C(O)=O Chemical compound *c(cc1)c(*)nc1C(O)=O 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12196022 | 2012-12-07 | ||
| EP12196022.3 | 2012-12-07 | ||
| PCT/EP2013/075225 WO2014086705A1 (en) | 2012-12-07 | 2013-12-02 | Novel pyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016501240A JP2016501240A (ja) | 2016-01-18 |
| JP2016501240A5 true JP2016501240A5 (cg-RX-API-DMAC7.html) | 2017-01-19 |
| JP6426618B2 JP6426618B2 (ja) | 2018-11-21 |
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| JP2015545757A Expired - Fee Related JP6426618B2 (ja) | 2012-12-07 | 2013-12-02 | 新規なピリジン誘導体 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2964646B1 (en) | 2013-03-07 | 2017-04-19 | F. Hoffmann-La Roche AG | Novel pyrazol derivatives |
| CA2899168A1 (en) | 2013-03-26 | 2014-10-02 | F. Hoffmann-La Roche Ag | Novel pyridine derivatives |
| ES2635632T3 (es) | 2013-05-02 | 2017-10-04 | F. Hoffmann-La Roche Ag | Derivados de pirrolo[2,3-d]pirimidina como agonistas del receptor CB2 |
| PT2991987T (pt) | 2013-05-02 | 2018-07-13 | Hoffmann La Roche | Derivados de purina como agonistas do recetor cb2 |
| CA2915766C (en) | 2013-09-06 | 2023-09-26 | F. Hoffmann-La Roche Ag | Triazolo[4,5-d]pyrimidine derivatives and their use as cannabinoid receptor 2 agonists |
| KR20160132495A (ko) * | 2014-04-04 | 2016-11-18 | 에프. 호프만-라 로슈 아게 | 카나비노이드 수용체 작용제로서 5,6-이치환된 피리딘-2-카복스아미드 |
| EP3156397B1 (en) | 2014-06-13 | 2019-08-07 | Takeda Pharmaceutical Company Limited | Nitrogen-containing heterocyclic compound |
| DK3386951T3 (en) * | 2015-12-09 | 2020-04-27 | Hoffmann La Roche | Phenylderivater som cannabinoidreceptor-2-agonister |
| WO2017107089A1 (en) | 2015-12-23 | 2017-06-29 | Merck Sharp & Dohme Corp. | 3- (1h-pyrazol-4-yl) pyridineallosteric modulators of the m4 muscarinic acetylcholine receptor |
| EP3642200B1 (en) | 2017-06-20 | 2023-05-03 | F. Hoffmann-La Roche AG | Pyridine derivatives |
| CN112041309A (zh) * | 2018-04-18 | 2020-12-04 | 巴斯夫欧洲公司 | D-葡糖二酸-6,3-内酯单酯及其制备方法 |
| CN112074513B (zh) | 2018-06-27 | 2024-06-14 | 豪夫迈·罗氏有限公司 | 作为优先大麻素2激动剂的吡啶和吡嗪衍生物 |
| JP7478672B2 (ja) * | 2018-06-27 | 2024-05-07 | エフ． ホフマン－ラ ロシュ アーゲー | カンナビノイド受容体２の阻害剤としての新規なアゼチジン置換ピリジン及びピラジン化合物 |
| MA53002A (fr) | 2018-06-27 | 2021-05-05 | Eth Zuerich | Nouveaux composés de pyridine et de pyrazine en tant qu'inhibiteurs du récepteur cannabinoïde 2 |
| EP3813888B1 (en) | 2018-06-27 | 2025-11-26 | F. Hoffmann-La Roche AG | Radiolabeled cannabinoid receptor 2 ligand |
| EP4038055A1 (en) * | 2019-09-30 | 2022-08-10 | F. Hoffmann-La Roche AG | Substituted 3,4-dihydroquinazoline for the treatment and prophylaxis of hepatitis b virus infection |
| CA3192236A1 (en) | 2020-09-10 | 2022-03-17 | Tony Lahoutte | Antibody fragment against fap |
| EP4326257A4 (en) | 2021-04-19 | 2025-03-12 | ChemoCentryx, Inc. | AZETIDINYLACETAMIDES AS CXCR7 INHIBITORS |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| JP2025517625A (ja) | 2022-05-02 | 2025-06-10 | プレシリックス・ナームローゼ・ベンノートシヤープ | プレターゲティング |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2009003316A (es) | 2006-10-04 | 2009-04-09 | Hoffmann La Roche | Derivados de pirazina-2-carboxamida como moduladores receptores de cb2. |
| WO2012031817A1 (en) * | 2010-09-09 | 2012-03-15 | F. Hoffmann-La Roche Ag | Determination of abca1 protein levels in cells |
| AR085013A1 (es) * | 2011-01-26 | 2013-08-07 | Sanofi Aventis | Derivados de acido 3-heteroaroilamino-propionico sustituidos y su uso como sustancias farmaceuticas |
| US9321727B2 (en) | 2011-06-10 | 2016-04-26 | Hoffmann-La Roche Inc. | Pyridine derivatives as agonists of the CB2 receptor |
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2013
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- 2013-12-02 WO PCT/EP2013/075225 patent/WO2014086705A1/en not_active Ceased
- 2013-12-02 EP EP18154216.8A patent/EP3357918A1/en not_active Withdrawn
- 2013-12-02 LT LTEP13799520.5T patent/LT2928881T/lt unknown
- 2013-12-02 DK DK13799520.5T patent/DK2928881T3/en active
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- 2013-12-02 ES ES13799520.5T patent/ES2668690T3/es active Active
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- 2013-12-02 AU AU2013354278A patent/AU2013354278B2/en not_active Ceased
- 2013-12-02 US US14/648,431 patent/US9522886B2/en not_active Expired - Fee Related
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- 2013-12-02 JP JP2015545757A patent/JP6426618B2/ja not_active Expired - Fee Related
- 2013-12-02 HU HUE13799520A patent/HUE036911T2/hu unknown
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- 2013-12-02 EA EA201591064A patent/EA026669B1/ru not_active IP Right Cessation
- 2013-12-02 MA MA38239A patent/MA38239A1/fr unknown
- 2013-12-02 CN CN201710932324.2A patent/CN107674061A/zh active Pending
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- 2013-12-02 PE PE2015000744A patent/PE20151025A1/es not_active Application Discontinuation
- 2013-12-02 KR KR1020157017889A patent/KR20150092282A/ko not_active Withdrawn
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2015
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2017
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