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 |
|---|---|---|---|
| EP12196022.3 | 2012-12-07 | ||
| EP12196022 | 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 (OSRAM) | 2017-01-19 |
| JP6426618B2 JP6426618B2 (ja) | 2018-11-21 |
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Family Applications (1)
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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 |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US9522886B2 (OSRAM) |
| EP (2) | EP2928881B1 (OSRAM) |
| JP (1) | JP6426618B2 (OSRAM) |
| KR (1) | KR20150092282A (OSRAM) |
| CN (2) | CN107674061A (OSRAM) |
| AR (1) | AR093843A1 (OSRAM) |
| AU (2) | AU2013354278B2 (OSRAM) |
| BR (1) | BR112015012919A2 (OSRAM) |
| CA (1) | CA2890100A1 (OSRAM) |
| CL (1) | CL2015001536A1 (OSRAM) |
| CO (1) | CO7350620A2 (OSRAM) |
| CR (1) | CR20150250A (OSRAM) |
| DK (1) | DK2928881T3 (OSRAM) |
| EA (1) | EA026669B1 (OSRAM) |
| ES (1) | ES2668690T3 (OSRAM) |
| HR (1) | HRP20180672T1 (OSRAM) |
| HU (1) | HUE036911T2 (OSRAM) |
| IL (1) | IL239075B (OSRAM) |
| LT (1) | LT2928881T (OSRAM) |
| MA (1) | MA38239A1 (OSRAM) |
| MX (1) | MX2015007155A (OSRAM) |
| NO (1) | NO2928881T3 (OSRAM) |
| PE (1) | PE20151025A1 (OSRAM) |
| PH (1) | PH12015501083B1 (OSRAM) |
| PL (1) | PL2928881T3 (OSRAM) |
| PT (1) | PT2928881T (OSRAM) |
| RS (1) | RS57143B1 (OSRAM) |
| SG (2) | SG10201800170YA (OSRAM) |
| SI (1) | SI2928881T1 (OSRAM) |
| TW (1) | TWI600645B (OSRAM) |
| UA (1) | UA114656C2 (OSRAM) |
| WO (1) | WO2014086705A1 (OSRAM) |
| ZA (1) | ZA201503969B (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6514119B2 (ja) | 2013-03-07 | 2019-05-15 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 新規ピラゾール誘導体 |
| NO2978755T3 (OSRAM) | 2013-03-26 | 2018-06-02 | ||
| KR20160002857A (ko) | 2013-05-02 | 2016-01-08 | 에프. 호프만-라 로슈 아게 | CB2 수용체 작용제로서의 피롤로[2,3-d]피리미딘 유도체 |
| PE20151977A1 (es) | 2013-05-02 | 2016-01-07 | Hoffmann La Roche | Nuevos derivados de purina |
| KR20220140651A (ko) | 2013-09-06 | 2022-10-18 | 에프. 호프만-라 로슈 아게 | 신규의 트라이아졸로[4,5-d]피리미딘 유도체 |
| CR20160459A (es) * | 2014-04-04 | 2016-12-02 | Eidgenoessische Technische Hochschule Zuerich | Nuevos derivados de piridina |
| JP6571077B2 (ja) | 2014-06-13 | 2019-09-04 | 武田薬品工業株式会社 | 含窒素複素環化合物 |
| 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 |
| JP7300398B2 (ja) | 2017-06-20 | 2023-06-29 | エフ． ホフマン－ラ ロシュ アーゲー | ピリジン誘導体 |
| JP2021521228A (ja) * | 2018-04-18 | 2021-08-26 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | Ｄ−グルカロ−６，３−ラクトンモノエステル及びその製造方法 |
| BR112020025013A2 (pt) | 2018-06-27 | 2021-03-23 | F. Hoffmann-La Roche Ag | novos compostos de piridina e pirazina como inibidores do receptor 2 de canabinoide |
| 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 |
| EP3995155A1 (en) | 2018-06-27 | 2022-05-11 | F. Hoffmann-La Roche AG | Radiolabeled cannabinoid receptor 2 ligand |
| EP3814328A1 (en) * | 2018-06-27 | 2021-05-05 | F. Hoffmann-La Roche AG | Novel azetidine-substituted pyridine and pyrazine compounds as inhibitors of cannabinoid receptor 2 |
| WO2021063856A1 (en) * | 2019-09-30 | 2021-04-08 | F. Hoffmann-La Roche Ag | Substituted 3,4-dihydroquinazoline for the treatment and prophylaxis of hepatitis b virus infection |
| WO2022053651A2 (en) | 2020-09-10 | 2022-03-17 | Precirix N.V. | Antibody fragment against fap |
| CA3216874A1 (en) * | 2021-04-19 | 2022-10-27 | Chemocentryx, Inc. | Azetidinyl-acetamides as cxcr7 inhibitors |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| IL318992A (en) | 2022-05-02 | 2025-04-01 | Precirix N V | Cancer treatment through advance directives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2076499B1 (en) * | 2006-10-04 | 2010-05-12 | F.Hoffmann-La Roche Ag | Pyrazine-2-carboxamide derivatives as cb2 receptor modulators |
| WO2012031817A1 (en) * | 2010-09-09 | 2012-03-15 | F. Hoffmann-La Roche Ag | Determination of abca1 protein levels in cells |
| US8669370B2 (en) * | 2011-01-26 | 2014-03-11 | Sanofi | Substituted 3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals |
| US9321727B2 (en) * | 2011-06-10 | 2016-04-26 | Hoffmann-La Roche Inc. | Pyridine derivatives as agonists of the CB2 receptor |
-
2013
- 2013-12-02 SG SG10201800170YA patent/SG10201800170YA/en unknown
- 2013-12-02 CN CN201710932324.2A patent/CN107674061A/zh active Pending
- 2013-12-02 EP EP13799520.5A patent/EP2928881B1/en not_active Not-in-force
- 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 WO PCT/EP2013/075225 patent/WO2014086705A1/en not_active Ceased
- 2013-12-02 NO NO13799520A patent/NO2928881T3/no unknown
- 2013-12-02 CA CA2890100A patent/CA2890100A1/en not_active Abandoned
- 2013-12-02 HR HRP20180672TT patent/HRP20180672T1/hr unknown
- 2013-12-02 SI SI201331023T patent/SI2928881T1/en unknown
- 2013-12-02 UA UAA201506688A patent/UA114656C2/uk unknown
- 2013-12-02 EP EP18154216.8A patent/EP3357918A1/en not_active Withdrawn
- 2013-12-02 SG SG11201504416XA patent/SG11201504416XA/en unknown
- 2013-12-02 BR BR112015012919A patent/BR112015012919A2/pt not_active Application Discontinuation
- 2013-12-02 PT PT137995205T patent/PT2928881T/pt unknown
- 2013-12-02 PL PL13799520T patent/PL2928881T3/pl unknown
- 2013-12-02 LT LTEP13799520.5T patent/LT2928881T/lt unknown
- 2013-12-02 AU AU2013354278A patent/AU2013354278B2/en not_active Ceased
- 2013-12-02 CN CN201380063475.9A patent/CN104837831B/zh not_active Expired - Fee Related
- 2013-12-02 MX MX2015007155A patent/MX2015007155A/es unknown
- 2013-12-02 DK DK13799520.5T patent/DK2928881T3/en active
- 2013-12-02 PE PE2015000744A patent/PE20151025A1/es not_active Application Discontinuation
- 2013-12-02 HU HUE13799520A patent/HUE036911T2/hu unknown
- 2013-12-02 JP JP2015545757A patent/JP6426618B2/ja not_active Expired - Fee Related
- 2013-12-02 ES ES13799520.5T patent/ES2668690T3/es active Active
- 2013-12-02 US US14/648,431 patent/US9522886B2/en not_active Expired - Fee Related
- 2013-12-02 RS RS20180493A patent/RS57143B1/sr unknown
- 2013-12-02 KR KR1020157017889A patent/KR20150092282A/ko not_active Withdrawn
- 2013-12-06 AR ARP130104545A patent/AR093843A1/es unknown
- 2013-12-06 TW TW102144952A patent/TWI600645B/zh not_active IP Right Cessation
-
2015
- 2015-04-29 CO CO15097806A patent/CO7350620A2/es unknown
- 2015-05-12 CR CR20150250A patent/CR20150250A/es unknown
- 2015-05-15 PH PH12015501083A patent/PH12015501083B1/en unknown
- 2015-05-28 IL IL239075A patent/IL239075B/en not_active IP Right Cessation
- 2015-06-03 ZA ZA2015/03969A patent/ZA201503969B/en unknown
- 2015-06-05 CL CL2015001536A patent/CL2015001536A1/es unknown
-
2017
- 2017-12-20 AU AU2017279648A patent/AU2017279648A1/en not_active Abandoned
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