KR20190017030A - Dnmt1의 억제제로서의 치환된 피리딘 - Google Patents
Dnmt1의 억제제로서의 치환된 피리딘 Download PDFInfo
- Publication number
- KR20190017030A KR20190017030A KR1020197000766A KR20197000766A KR20190017030A KR 20190017030 A KR20190017030 A KR 20190017030A KR 1020197000766 A KR1020197000766 A KR 1020197000766A KR 20197000766 A KR20197000766 A KR 20197000766A KR 20190017030 A KR20190017030 A KR 20190017030A
- Authority
- KR
- South Korea
- Prior art keywords
- dicyano
- thio
- phenylacetamide
- amino
- ethyl
- 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.)
- Ceased
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- 150000003222 pyridines Chemical class 0.000 title claims abstract description 9
- 239000003112 inhibitor Substances 0.000 title claims description 9
- 102100036279 DNA (cytosine-5)-methyltransferase 1 Human genes 0.000 title abstract description 24
- 108010009540 DNA (Cytosine-5-)-Methyltransferase 1 Proteins 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 150000003839 salts Chemical class 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 53
- 208000007056 sickle cell anemia Diseases 0.000 claims abstract description 43
- 238000011282 treatment Methods 0.000 claims abstract description 41
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
- 201000011510 cancer Diseases 0.000 claims abstract description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 229940002612 prodrug Drugs 0.000 claims abstract description 25
- 239000000651 prodrug Substances 0.000 claims abstract description 25
- 208000005980 beta thalassemia Diseases 0.000 claims abstract description 17
- 208000022806 beta-thalassemia major Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 16
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 15
- 208000018565 Hemochromatosis Diseases 0.000 claims abstract description 14
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 9
- 230000005764 inhibitory process Effects 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 1092
- -1 Chloro, Bromo, Iodo Chemical group 0.000 claims description 942
- 125000001153 fluoro group Chemical group F* 0.000 claims description 524
- 125000001424 substituent group Chemical group 0.000 claims description 468
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 371
- 125000004043 oxo group Chemical group O=* 0.000 claims description 362
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 353
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 349
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 331
- 125000003118 aryl group Chemical group 0.000 claims description 322
- 125000001072 heteroaryl group Chemical group 0.000 claims description 302
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 260
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 154
- 125000003545 alkoxy group Chemical group 0.000 claims description 146
- 229910052739 hydrogen Inorganic materials 0.000 claims description 135
- 239000001257 hydrogen Substances 0.000 claims description 135
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 98
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 69
- 125000001246 bromo group Chemical group Br* 0.000 claims description 58
- 125000002346 iodo group Chemical group I* 0.000 claims description 55
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 19
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 229940034982 antineoplastic agent Drugs 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 210000004027 cell Anatomy 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 230000006378 damage Effects 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 273
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 166
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 116
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 58
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 claims 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 40
- 125000003386 piperidinyl group Chemical group 0.000 claims 20
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims 19
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 19
- 150000001408 amides Chemical class 0.000 claims 18
- 241000124008 Mammalia Species 0.000 claims 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 17
- 125000002883 imidazolyl group Chemical group 0.000 claims 17
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 15
- QKYYCHBWOLRIJJ-UHFFFAOYSA-N 2-pyrimidin-2-ylacetamide Chemical compound NC(=O)CC1=NC=CC=N1 QKYYCHBWOLRIJJ-UHFFFAOYSA-N 0.000 claims 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 12
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 12
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 12
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 12
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 12
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 11
- 125000003566 oxetanyl group Chemical group 0.000 claims 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims 11
- 125000002785 azepinyl group Chemical group 0.000 claims 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 10
- 208000009956 adenocarcinoma Diseases 0.000 claims 9
- 125000002393 azetidinyl group Chemical group 0.000 claims 8
- ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 8
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 7
- LNEBGQBVQRBDMK-UHFFFAOYSA-N 2-[6-(4-amino-4-methylpiperidin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1(CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N)C LNEBGQBVQRBDMK-UHFFFAOYSA-N 0.000 claims 6
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 6
- 201000009030 Carcinoma Diseases 0.000 claims 6
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 6
- FQYYIPZPELSLDK-UHFFFAOYSA-N ethyl pyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=CC=N1 FQYYIPZPELSLDK-UHFFFAOYSA-N 0.000 claims 6
- 208000005017 glioblastoma Diseases 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- XLECGUSMKLPCGO-UHFFFAOYSA-N pyrrolidin-3-yl dihydrogen phosphate Chemical compound OP(O)(=O)OC1CCNC1 XLECGUSMKLPCGO-UHFFFAOYSA-N 0.000 claims 6
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 5
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 5
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 5
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 5
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 150000003852 triazoles Chemical class 0.000 claims 5
- AYZZJIDLBKXRKQ-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[2-(hydroxymethyl)morpholin-4-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(OCC1)CO)SC(C(=O)N)C1=CC=CC=C1 AYZZJIDLBKXRKQ-UHFFFAOYSA-N 0.000 claims 4
- QVROPBZLGMQZIH-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[3-(dimethylamino)piperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(CCC1)N(C)C)SC(C(=O)N)C1=CC=CC=C1 QVROPBZLGMQZIH-UHFFFAOYSA-N 0.000 claims 4
- RKAYIEFADPAEOO-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-methyl-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CCC1)C)SC(C(=O)N)C1=CC=CC=C1 RKAYIEFADPAEOO-UHFFFAOYSA-N 0.000 claims 4
- AYNULTGWVKTAEP-UHFFFAOYSA-N 2-[6-(3-aminoazetidin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CN(C1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N AYNULTGWVKTAEP-UHFFFAOYSA-N 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 4
- LBZFDLXSLMTNIX-UHFFFAOYSA-N [1-[6-(2-amino-2-oxo-1-phenylethyl)sulfanyl-3,5-dicyano-4-ethylpyridin-2-yl]azetidin-3-yl] dihydrogen phosphate Chemical compound P(=O)(OC1CN(C1)C1=NC(=C(C(=C1C#N)CC)C#N)SC(C(=O)N)C1=CC=CC=C1)(O)O LBZFDLXSLMTNIX-UHFFFAOYSA-N 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 4
- BQIVJVAZDJHDJF-UHFFFAOYSA-N ethyl 2-amino-3-methylbutanoate Chemical compound CCOC(=O)C(N)C(C)C BQIVJVAZDJHDJF-UHFFFAOYSA-N 0.000 claims 4
- RSPHTIQPMLLATO-UHFFFAOYSA-N ethyl 3-fluoropyridine-2-carboxylate Chemical compound CCOC(=O)C1=NC=CC=C1F RSPHTIQPMLLATO-UHFFFAOYSA-N 0.000 claims 4
- YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical compound CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 claims 4
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 4
- FATAVLOOLIRUNA-UHFFFAOYSA-N formylmethyl Chemical group [CH2]C=O FATAVLOOLIRUNA-UHFFFAOYSA-N 0.000 claims 4
- 206010022498 insulinoma Diseases 0.000 claims 4
- 208000032839 leukemia Diseases 0.000 claims 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 4
- 201000002528 pancreatic cancer Diseases 0.000 claims 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 4
- 208000021255 pancreatic insulinoma Diseases 0.000 claims 4
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 4
- AGNMYVAFHGZZAZ-UHFFFAOYSA-N piperidin-4-yl dihydrogen phosphate Chemical compound OP(O)(=O)OC1CCNCC1 AGNMYVAFHGZZAZ-UHFFFAOYSA-N 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 4
- 238000003786 synthesis reaction Methods 0.000 claims 4
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 206010003571 Astrocytoma Diseases 0.000 claims 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims 3
- 206010006187 Breast cancer Diseases 0.000 claims 3
- 208000026310 Breast neoplasm Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 208000032612 Glial tumor Diseases 0.000 claims 3
- 206010018338 Glioma Diseases 0.000 claims 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 3
- 206010033128 Ovarian cancer Diseases 0.000 claims 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 3
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 3
- 239000005557 antagonist Substances 0.000 claims 3
- 208000029742 colonic neoplasm Diseases 0.000 claims 3
- 201000010536 head and neck cancer Diseases 0.000 claims 3
- 208000014829 head and neck neoplasm Diseases 0.000 claims 3
- 201000007270 liver cancer Diseases 0.000 claims 3
- 208000014018 liver neoplasm Diseases 0.000 claims 3
- 201000005202 lung cancer Diseases 0.000 claims 3
- 208000020816 lung neoplasm Diseases 0.000 claims 3
- 201000001441 melanoma Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 201000002510 thyroid cancer Diseases 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- CITLODUGFLYYPD-GOSISDBHSA-N (2R)-2-(3,5-dicyano-4-ethyl-6-morpholin-4-ylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCOCC1)S[C@@H](C(=O)N)C1=CC=CC=C1 CITLODUGFLYYPD-GOSISDBHSA-N 0.000 claims 2
- XOYGSTAJAGOUHB-QGZVFWFLSA-N (2R)-2-[3,5-dicyano-4-ethyl-6-[2-hydroxyethyl(methyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCO)S[C@@H](C(=O)N)C1=CC=CC=C1 XOYGSTAJAGOUHB-QGZVFWFLSA-N 0.000 claims 2
- SEPYRSOYBZMXCN-GOSISDBHSA-N (2R)-2-[3,5-dicyano-4-ethyl-6-[3-hydroxypropyl(methyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCCO)S[C@@H](C(=O)N)C1=CC=CC=C1 SEPYRSOYBZMXCN-GOSISDBHSA-N 0.000 claims 2
- KIEQQZZDWUNUQK-MRXNPFEDSA-N (2R)-2-[3,5-dicyano-6-(dimethylamino)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)C)S[C@@H](C(=O)N)C1=CC=CC=C1 KIEQQZZDWUNUQK-MRXNPFEDSA-N 0.000 claims 2
- MELQQCMEXPGRLW-OAQYLSRUSA-N (2R)-2-[3,5-dicyano-6-[4-(dimethylamino)piperidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)N(C)C)S[C@@H](C(=O)N)C1=CC=CC=C1 MELQQCMEXPGRLW-OAQYLSRUSA-N 0.000 claims 2
- KNKHRZYILDZLRE-LJQANCHMSA-N (2R)-2-[6-(4-aminopiperidin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CCN(CC1)C1=C(C(=C(C(=N1)S[C@@H](C(=O)N)C1=CC=CC=C1)C#N)CC)C#N KNKHRZYILDZLRE-LJQANCHMSA-N 0.000 claims 2
- HSKVBTYMHPVTJH-LJQANCHMSA-N (2R)-2-[[3,5-dicyano-6-(1,4-diazepan-1-yl)-4-ethylpyridin-2-yl]amino]-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCNCCC1)N[C@@H](C(=O)N)C1=CC=CC=C1 HSKVBTYMHPVTJH-LJQANCHMSA-N 0.000 claims 2
- KIEQQZZDWUNUQK-QKHLJXARSA-N (2R)-2-deuterio-2-[3,5-dicyano-6-(dimethylamino)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)C)S[C@](C(=O)N)([2H])C1=CC=CC=C1 KIEQQZZDWUNUQK-QKHLJXARSA-N 0.000 claims 2
- KNKHRZYILDZLRE-IBGZPJMESA-N (2S)-2-[6-(4-aminopiperidin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CCN(CC1)C1=C(C(=C(C(=N1)S[C@H](C(=O)N)C1=CC=CC=C1)C#N)CC)C#N KNKHRZYILDZLRE-IBGZPJMESA-N 0.000 claims 2
- LZTSCEYDCZBRCJ-UHFFFAOYSA-N 1,2-dihydro-1,2,4-triazol-3-one Chemical compound OC=1N=CNN=1 LZTSCEYDCZBRCJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- KYURKRFGKGRNNG-UHFFFAOYSA-N 2-(3,5-dichloro-4-ethyl-6-piperazin-1-ylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound ClC=1C(=NC(=C(C=1CC)Cl)N1CCNCC1)SC(C(=O)N)C1=CC=CC=C1 KYURKRFGKGRNNG-UHFFFAOYSA-N 0.000 claims 2
- DHNDYNWUHXEKBW-UHFFFAOYSA-N 2-(3,5-dicyano-4,6-diethylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)CC)SC(C(=O)N)C1=CC=CC=C1 DHNDYNWUHXEKBW-UHFFFAOYSA-N 0.000 claims 2
- AFWBPDSPAKJTII-UHFFFAOYSA-N 2-(3,5-dicyano-4-cyclopropyl-6-morpholin-4-ylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CCOCC1)SC(C(=O)N)C1=CC=CC=C1 AFWBPDSPAKJTII-UHFFFAOYSA-N 0.000 claims 2
- ZLCZVATZPMXDKH-UHFFFAOYSA-N 2-(3,5-dicyano-4-ethoxy-6-methylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1OCC)C#N)C)SC(C(=O)N)C1=CC=CC=C1 ZLCZVATZPMXDKH-UHFFFAOYSA-N 0.000 claims 2
- JSCBRTMDYAZVCC-UHFFFAOYSA-N 2-(3,5-dicyano-4-ethyl-6-methylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)C)SC(C(=O)N)C1=CC=CC=C1 JSCBRTMDYAZVCC-UHFFFAOYSA-N 0.000 claims 2
- CITLODUGFLYYPD-UHFFFAOYSA-N 2-(3,5-dicyano-4-ethyl-6-morpholin-4-ylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCOCC1)SC(C(=O)N)C1=CC=CC=C1 CITLODUGFLYYPD-UHFFFAOYSA-N 0.000 claims 2
- ZWCZXCXGYPKPTE-UHFFFAOYSA-N 2-(3,5-dicyano-4-ethyl-6-piperazin-1-ylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCNCC1)SC(C(=O)N)C1=CC=CC=C1 ZWCZXCXGYPKPTE-UHFFFAOYSA-N 0.000 claims 2
- BJCGICNWOLCBHD-UHFFFAOYSA-N 2-(3,5-dicyano-4-ethylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound NC(C(C1=CC=CC=C1)SC1=C(C(=C(C=N1)C#N)CC)C#N)=O BJCGICNWOLCBHD-UHFFFAOYSA-N 0.000 claims 2
- XZSDQGMQWFSLJW-UHFFFAOYSA-N 2-(3-cyano-4-ethyl-5-methyl-6-piperazin-1-ylpyridin-2-yl)sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C)N1CCNCC1)SC(C(=O)N)C1=CC=CC=C1 XZSDQGMQWFSLJW-UHFFFAOYSA-N 0.000 claims 2
- STOCLPJPNSTUAB-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-[3,5-dicyano-6-(dimethylamino)-4-ethylpyridin-2-yl]sulfanylacetamide Chemical compound ClC1=CC=C(C=C1)C(C(=O)N)SC1=NC(=C(C(=C1C#N)CC)C#N)N(C)C STOCLPJPNSTUAB-UHFFFAOYSA-N 0.000 claims 2
- IUQJKSRIDGDWOK-UHFFFAOYSA-N 2-(4-methyl-1,4-diazepan-1-yl)-4-methylsulfanylpyridine-3,5-dicarbonitrile Chemical compound C(#N)C=1C=NC(=C(C=1SC)C#N)N1CCN(CCC1)C IUQJKSRIDGDWOK-UHFFFAOYSA-N 0.000 claims 2
- QVYZTTVPGJCRMT-LLVKDONJSA-N 2-[(2R)-2-(aminomethyl)morpholin-4-yl]-4-ethylpyridine-3,5-dicarbonitrile Chemical compound NC[C@H]1OCCN(C1)C1=C(C(=C(C=N1)C#N)CC)C#N QVYZTTVPGJCRMT-LLVKDONJSA-N 0.000 claims 2
- LZGCBIRFDAKIIX-OAHLLOKOSA-N 2-[(2R)-2-(diethylaminomethyl)morpholin-4-yl]-4-ethylpyridine-3,5-dicarbonitrile Chemical compound C(#N)C=1C=NC(=C(C=1CC)C#N)N1C[C@H](OCC1)CN(CC)CC LZGCBIRFDAKIIX-OAHLLOKOSA-N 0.000 claims 2
- NUEXOSBNFCJKFO-OAHLLOKOSA-N 2-[(2R)-2-[(2,2-dimethylpropylamino)methyl]morpholin-4-yl]-4-ethylpyridine-3,5-dicarbonitrile Chemical compound C(#N)C=1C=NC(=C(C=1CC)C#N)N1C[C@H](OCC1)CNCC(C)(C)C NUEXOSBNFCJKFO-OAHLLOKOSA-N 0.000 claims 2
- NUEXOSBNFCJKFO-HNNXBMFYSA-N 2-[(2S)-2-[(2,2-dimethylpropylamino)methyl]morpholin-4-yl]-4-ethylpyridine-3,5-dicarbonitrile Chemical compound C(#N)C=1C=NC(=C(C=1CC)C#N)N1C[C@@H](OCC1)CNCC(C)(C)C NUEXOSBNFCJKFO-HNNXBMFYSA-N 0.000 claims 2
- ROOQPSGPTHMDFA-GFCCVEGCSA-N 2-[(3R)-3-(dimethylamino)pyrrolidin-1-yl]-4-ethylpyridine-3,5-dicarbonitrile Chemical compound C(#N)C=1C=NC(=C(C=1CC)C#N)N1C[C@@H](CC1)N(C)C ROOQPSGPTHMDFA-GFCCVEGCSA-N 0.000 claims 2
- ROOQPSGPTHMDFA-LBPRGKRZSA-N 2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-4-ethylpyridine-3,5-dicarbonitrile Chemical compound C(#N)C=1C=NC(=C(C=1CC)C#N)N1C[C@H](CC1)N(C)C ROOQPSGPTHMDFA-LBPRGKRZSA-N 0.000 claims 2
- BIKGIIMWQRGVJH-UHFFFAOYSA-N 2-[3,5-dichloro-4-ethyl-6-(4-methyl-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound ClC=1C(=NC(=C(C=1CC)Cl)N1CCN(CCC1)C)SC(C(=O)N)C1=CC=CC=C1 BIKGIIMWQRGVJH-UHFFFAOYSA-N 0.000 claims 2
- PAUHBDXOZUTHBS-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CCNCCC1)SC(C(=O)N)C1=CC=CC=C1 PAUHBDXOZUTHBS-UHFFFAOYSA-N 0.000 claims 2
- IYEHEHCKPMJGMI-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(2,6-dimethylmorpholin-4-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(OC(C1)C)C)SC(C(=O)N)C1=CC=CC=C1 IYEHEHCKPMJGMI-UHFFFAOYSA-N 0.000 claims 2
- WZQFJKWYRNLKDK-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(3-hydroxypiperidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(CCC1)O)SC(C(=O)N)C1=CC=CC=C1 WZQFJKWYRNLKDK-UHFFFAOYSA-N 0.000 claims 2
- KSEUXNSAPLLRCN-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(3-hydroxypyrrolidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(CC1)O)SC(C(=O)N)C1=CC=CC=C1 KSEUXNSAPLLRCN-UHFFFAOYSA-N 0.000 claims 2
- RKGZAWAZEJZLRD-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(3-methylpiperazin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(NCC1)C)SC(C(=O)N)C1=CC=CC=C1 RKGZAWAZEJZLRD-UHFFFAOYSA-N 0.000 claims 2
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- IPIAHZTYERRXQS-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(4-ethyl-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CCN(CCC1)CC)SC(C(=O)N)C1=CC=CC=C1 IPIAHZTYERRXQS-UHFFFAOYSA-N 0.000 claims 2
- BBCJAXNYDGYRPG-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(5-oxo-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CCNC(CC1)=O)SC(C(=O)N)C1=CC=CC=C1 BBCJAXNYDGYRPG-UHFFFAOYSA-N 0.000 claims 2
- SQSPRRWZSIZYKO-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-(dimethylamino)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N(C)C)SC(C(=O)N)C1=CC=CC=C1 SQSPRRWZSIZYKO-UHFFFAOYSA-N 0.000 claims 2
- WZQFJKWYRNLKDK-QRIPLOBPSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[(3R)-3-hydroxypiperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1C[C@@H](CCC1)O)SC(C(=O)N)C1=CC=CC=C1 WZQFJKWYRNLKDK-QRIPLOBPSA-N 0.000 claims 2
- WZQFJKWYRNLKDK-DJZRFWRSSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[(3S)-3-hydroxypiperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1C[C@H](CCC1)O)SC(C(=O)N)C1=CC=CC=C1 WZQFJKWYRNLKDK-DJZRFWRSSA-N 0.000 claims 2
- JJLWDWRURXASKJ-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[2-hydroxyethyl(methyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N(C)CCO)SC(C(=O)N)C1=CC=CC=C1 JJLWDWRURXASKJ-UHFFFAOYSA-N 0.000 claims 2
- VRKPCWYOSROMON-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[3-(hydroxymethyl)piperazin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(NCC1)CO)SC(C(=O)N)C1=CC=CC=C1 VRKPCWYOSROMON-UHFFFAOYSA-N 0.000 claims 2
- MTKDQKSITHIDHV-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[3-(methylamino)piperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CC(CCC1)NC)SC(C(=O)N)C1=CC=CC=C1 MTKDQKSITHIDHV-UHFFFAOYSA-N 0.000 claims 2
- DQOICBVYYITCQG-UHFFFAOYSA-N 2-[3,5-dicyano-4-cyclopropyl-6-[4-(dimethylamino)piperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1C1CC1)C#N)N1CCC(CC1)N(C)C)SC(C(=O)N)C1=CC=CC=C1 DQOICBVYYITCQG-UHFFFAOYSA-N 0.000 claims 2
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- KXVNYMOJYHKQRG-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(2-oxa-7-azaspiro[3.4]octan-7-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC2(COC2)CC1)SC(C(=O)N)C1=CC=CC=C1 KXVNYMOJYHKQRG-UHFFFAOYSA-N 0.000 claims 2
- TWLBWWRTVQHOCK-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(3-hydroxypyrrolidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(CC1)O)SC(C(=O)N)C1=CC=CC=C1 TWLBWWRTVQHOCK-UHFFFAOYSA-N 0.000 claims 2
- JXAUMWOTJFLYOC-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(3-methoxyazetidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(C1)OC)SC(C(=O)N)C1=CC=CC=C1 JXAUMWOTJFLYOC-UHFFFAOYSA-N 0.000 claims 2
- MLKKPDGYCFASPL-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(3-oxopiperazin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(NCC1)=O)SC(C(=O)N)C1=CC=CC=C1 MLKKPDGYCFASPL-UHFFFAOYSA-N 0.000 claims 2
- AVLOZCTUBSLSSQ-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-ethyl-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CCC1)CC)SC(C(=O)N)C1=CC=CC=C1 AVLOZCTUBSLSSQ-UHFFFAOYSA-N 0.000 claims 2
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- MZWZOPMPMLVLSG-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-hydroxypiperidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)O)SC(C(=O)N)C1=CC=CC=C1 MZWZOPMPMLVLSG-UHFFFAOYSA-N 0.000 claims 2
- WHHWWBOLJJWTFW-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-morpholin-4-ylpiperidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)N1CCOCC1)SC(C(=O)N)C1=CC=CC=C1 WHHWWBOLJJWTFW-UHFFFAOYSA-N 0.000 claims 2
- ZSYCORUQBBRZST-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-oxopiperidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)=O)SC(C(=O)N)C1=CC=CC=C1 ZSYCORUQBBRZST-UHFFFAOYSA-N 0.000 claims 2
- SBQYYTLFKRYESN-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-piperidin-4-ylpiperidin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound N1(CCC(CC1)C1CCNCC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N SBQYYTLFKRYESN-UHFFFAOYSA-N 0.000 claims 2
- ADKADAJBRJLLDR-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-propyl-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CCC1)CCC)SC(C(=O)N)C1=CC=CC=C1 ADKADAJBRJLLDR-UHFFFAOYSA-N 0.000 claims 2
- BXSOWNMNUBXYQU-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-propylpiperazin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CC1)CCC)SC(C(=O)N)C1=CC=CC=C1 BXSOWNMNUBXYQU-UHFFFAOYSA-N 0.000 claims 2
- XYFVYDXBONPTKL-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(4-propylsulfonylpiperazin-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CC1)S(=O)(=O)CCC)SC(C(=O)N)C1=CC=CC=C1 XYFVYDXBONPTKL-UHFFFAOYSA-N 0.000 claims 2
- NKZHWEUPJPIVQG-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(5-methyl-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCNC(CC1)C)SC(C(=O)N)C1=CC=CC=C1 NKZHWEUPJPIVQG-UHFFFAOYSA-N 0.000 claims 2
- DYRMDGWLQARAHJ-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(5-oxo-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCNC(CC1)=O)SC(C(=O)N)C1=CC=CC=C1 DYRMDGWLQARAHJ-UHFFFAOYSA-N 0.000 claims 2
- LEXIGEPZZLZYMJ-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-(6-fluoro-1,4-diazepan-1-yl)pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCNCC(C1)F)SC(C(=O)N)C1=CC=CC=C1 LEXIGEPZZLZYMJ-UHFFFAOYSA-N 0.000 claims 2
- TWLBWWRTVQHOCK-IKJXHCRLSA-N 2-[3,5-dicyano-4-ethyl-6-[(3R)-3-hydroxypyrrolidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1C[C@@H](CC1)O)SC(C(=O)N)C1=CC=CC=C1 TWLBWWRTVQHOCK-IKJXHCRLSA-N 0.000 claims 2
- TWLBWWRTVQHOCK-PIVQAISJSA-N 2-[3,5-dicyano-4-ethyl-6-[(3S)-3-hydroxypyrrolidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1C[C@H](CC1)O)SC(C(=O)N)C1=CC=CC=C1 TWLBWWRTVQHOCK-PIVQAISJSA-N 0.000 claims 2
- BZTZVKGCRZLLBX-CWQZNGJJSA-N 2-[3,5-dicyano-4-ethyl-6-[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1OC[C@H](C1)O)SC(C(=O)N)C1=CC=CC=C1 BZTZVKGCRZLLBX-CWQZNGJJSA-N 0.000 claims 2
- TVKFTXSUHZNTFK-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[2-(ethylamino)ethyl-methylamino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCNCC)SC(C(=O)N)C1=CC=CC=C1 TVKFTXSUHZNTFK-UHFFFAOYSA-N 0.000 claims 2
- GKIMTORUWNIQRW-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[2-(methylaminomethyl)morpholin-4-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(OCC1)CNC)SC(C(=O)N)C1=CC=CC=C1 GKIMTORUWNIQRW-UHFFFAOYSA-N 0.000 claims 2
- GWIYLVSLHAAZEW-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[2-(pyrrolidin-1-ylmethyl)morpholin-4-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(OCC1)CN1CCCC1)SC(C(=O)N)C1=CC=CC=C1 GWIYLVSLHAAZEW-UHFFFAOYSA-N 0.000 claims 2
- ZIGAZNXZOLPFOS-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[2-[ethyl(methyl)amino]ethyl-methylamino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCN(C)CC)SC(C(=O)N)C1=CC=CC=C1 ZIGAZNXZOLPFOS-UHFFFAOYSA-N 0.000 claims 2
- XOYGSTAJAGOUHB-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[2-hydroxyethyl(methyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCO)SC(C(=O)N)C1=CC=CC=C1 XOYGSTAJAGOUHB-UHFFFAOYSA-N 0.000 claims 2
- WUIIBRJZPQPKLB-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[2-methoxyethyl(methyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCOC)SC(C(=O)N)C1=CC=CC=C1 WUIIBRJZPQPKLB-UHFFFAOYSA-N 0.000 claims 2
- HIQJFAUXGXYIDL-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[3-(hydroxymethyl)azetidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(C1)CO)SC(C(=O)N)C1=CC=CC=C1 HIQJFAUXGXYIDL-UHFFFAOYSA-N 0.000 claims 2
- TXXSJMRWNWLMIM-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[3-(methylamino)pyrrolidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(CC1)NC)SC(C(=O)N)C1=CC=CC=C1 TXXSJMRWNWLMIM-UHFFFAOYSA-N 0.000 claims 2
- NJVYJNIZUSABLP-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[3-(methylaminomethyl)piperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(CCC1)CNC)SC(C(=O)N)C1=CC=CC=C1 NJVYJNIZUSABLP-UHFFFAOYSA-N 0.000 claims 2
- DHHQTWDRYOCVNT-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[4-(2-hydroxyethyl)piperazin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CC1)CCO)SC(C(=O)N)C1=CC=CC=C1 DHHQTWDRYOCVNT-UHFFFAOYSA-N 0.000 claims 2
- ZYLLCQFEFGXLIG-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[4-(furan-3-ylmethyl)piperazin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CC1)CC1=COC=C1)SC(C(=O)N)C1=CC=CC=C1 ZYLLCQFEFGXLIG-UHFFFAOYSA-N 0.000 claims 2
- UFTKGXPMSNOOTN-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[4-(methylamino)piperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)NC)SC(C(=O)N)C1=CC=CC=C1 UFTKGXPMSNOOTN-UHFFFAOYSA-N 0.000 claims 2
- HOIWOTUORCYCGG-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[4-(pyridin-4-ylmethyl)piperazin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCN(CC1)CC1=CC=NC=C1)SC(C(=O)N)C1=CC=CC=C1 HOIWOTUORCYCGG-UHFFFAOYSA-N 0.000 claims 2
- MZUYDNIDARRTKI-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[4-[ethyl(methyl)amino]piperidin-1-yl]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)N(C)CC)SC(C(=O)N)C1=CC=CC=C1 MZUYDNIDARRTKI-UHFFFAOYSA-N 0.000 claims 2
- QWCYDTNDPXJDQJ-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[methyl(2-morpholin-4-ylethyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CCN1CCOCC1)C)SC(C(=O)N)C1=CC=CC=C1 QWCYDTNDPXJDQJ-UHFFFAOYSA-N 0.000 claims 2
- YOLKANZDCJBWCN-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[methyl(2-piperazin-1-ylethyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CCN1CCNCC1)C)SC(C(=O)N)C1=CC=CC=C1 YOLKANZDCJBWCN-UHFFFAOYSA-N 0.000 claims 2
- WSRKQFVILNOYDU-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[methyl(2-piperidin-1-ylethyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CCN1CCCCC1)C)SC(C(=O)N)C1=CC=CC=C1 WSRKQFVILNOYDU-UHFFFAOYSA-N 0.000 claims 2
- JRVWPOXQXJNLHI-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[methyl(2-pyrrolidin-1-ylethyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CCN1CCCC1)C)SC(C(=O)N)C1=CC=CC=C1 JRVWPOXQXJNLHI-UHFFFAOYSA-N 0.000 claims 2
- AZCDJBJGTWPUEH-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[methyl-(2-morpholin-4-yl-2-oxoethyl)amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CC(=O)N1CCOCC1)C)SC(C(=O)N)C1=CC=CC=C1 AZCDJBJGTWPUEH-UHFFFAOYSA-N 0.000 claims 2
- FLMFAKLJVLHPCJ-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[methyl-[2-(methylamino)ethyl]amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CCNC)C)SC(C(=O)N)C1=CC=CC=C1 FLMFAKLJVLHPCJ-UHFFFAOYSA-N 0.000 claims 2
- GYTNFNQZAZKEBM-UHFFFAOYSA-N 2-[3,5-dicyano-4-ethyl-6-[methyl-[2-[(1-methylcyclopropyl)amino]ethyl]amino]pyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CCNC1(CC1)C)C)SC(C(=O)N)C1=CC=CC=C1 GYTNFNQZAZKEBM-UHFFFAOYSA-N 0.000 claims 2
- HHQYFPQJWMQIOG-UHFFFAOYSA-N 2-[3,5-dicyano-6-(1,1-dioxo-1,4-thiazinan-4-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCS(CC1)(=O)=O)SC(C(=O)N)C1=CC=CC=C1 HHQYFPQJWMQIOG-UHFFFAOYSA-N 0.000 claims 2
- TYESDUSDOSXIOA-UHFFFAOYSA-N 2-[3,5-dicyano-6-(1,4-diazepan-1-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCNCCC1)SC(C(=O)N)C1=CC=CC=C1 TYESDUSDOSXIOA-UHFFFAOYSA-N 0.000 claims 2
- XWKHPFHSUYTASB-UHFFFAOYSA-N 2-[3,5-dicyano-6-(1,7-diazaspiro[3.5]nonan-1-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC11CCNCC1)SC(C(=O)N)C1=CC=CC=C1 XWKHPFHSUYTASB-UHFFFAOYSA-N 0.000 claims 2
- LEWPINXKUHMGEL-UHFFFAOYSA-N 2-[3,5-dicyano-6-(2,6-diazaspiro[3.4]octan-6-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC2(CNC2)CC1)SC(C(=O)N)C1=CC=CC=C1 LEWPINXKUHMGEL-UHFFFAOYSA-N 0.000 claims 2
- JMLPWQOLWATUHA-UHFFFAOYSA-N 2-[3,5-dicyano-6-(2,7-diazaspiro[3.5]nonan-7-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC2(CNC2)CC1)SC(C(=O)N)C1=CC=CC=C1 JMLPWQOLWATUHA-UHFFFAOYSA-N 0.000 claims 2
- BEBNLHNDQXVVCT-UHFFFAOYSA-N 2-[3,5-dicyano-6-(2,8-diazaspiro[4.5]decan-8-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC2(CCNC2)CC1)SC(C(=O)N)C1=CC=CC=C1 BEBNLHNDQXVVCT-UHFFFAOYSA-N 0.000 claims 2
- PXUHGLRILYSXLC-UHFFFAOYSA-N 2-[3,5-dicyano-6-(2,9-diazaspiro[5.5]undecan-9-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC2(CCCNC2)CC1)SC(C(=O)N)C1=CC=CC=C1 PXUHGLRILYSXLC-UHFFFAOYSA-N 0.000 claims 2
- NDADFHCJBWQSAN-UHFFFAOYSA-N 2-[3,5-dicyano-6-(4,4-difluoropiperidin-1-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)(F)F)SC(C(=O)N)C1=CC=CC=C1 NDADFHCJBWQSAN-UHFFFAOYSA-N 0.000 claims 2
- MOMXNTDAKQMDGL-UHFFFAOYSA-N 2-[3,5-dicyano-6-(4-cyanopiperidin-1-yl)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)C#N)SC(C(=O)N)C1=CC=CC=C1 MOMXNTDAKQMDGL-UHFFFAOYSA-N 0.000 claims 2
- VJZCIQKFGZRKOZ-UHFFFAOYSA-N 2-[3,5-dicyano-6-(dimethylamino)-4-ethoxypyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1OCC)C#N)N(C)C)SC(C(=O)N)C1=CC=CC=C1 VJZCIQKFGZRKOZ-UHFFFAOYSA-N 0.000 claims 2
- KIEQQZZDWUNUQK-UHFFFAOYSA-N 2-[3,5-dicyano-6-(dimethylamino)-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)C)SC(C(=O)N)C1=CC=CC=C1 KIEQQZZDWUNUQK-UHFFFAOYSA-N 0.000 claims 2
- PGEYCFMOSDKGRP-UHFFFAOYSA-N 2-[3,5-dicyano-6-(dimethylamino)-4-methoxypyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1OC)C#N)N(C)C)SC(C(=O)N)C1=CC=CC=C1 PGEYCFMOSDKGRP-UHFFFAOYSA-N 0.000 claims 2
- JVFVJIMPWTUARY-CWQZNGJJSA-N 2-[3,5-dicyano-6-[(3S)-3-hydroxypyrrolidin-1-yl]-4-methoxypyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1OC)C#N)N1C[C@H](CC1)O)SC(C(=O)N)C1=CC=CC=C1 JVFVJIMPWTUARY-CWQZNGJJSA-N 0.000 claims 2
- XMZRJKUIERXLEA-UHFFFAOYSA-N 2-[3,5-dicyano-6-[2-(2,2-dimethylpropylamino)ethyl-methylamino]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(CCNCC(C)(C)C)C)SC(C(=O)N)C1=CC=CC=C1 XMZRJKUIERXLEA-UHFFFAOYSA-N 0.000 claims 2
- XXJFYRYKHCNOQK-UHFFFAOYSA-N 2-[3,5-dicyano-6-[2-(diaminomethylideneamino)oxyethyl-methylamino]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCONC(=N)N)SC(C(=O)N)C1=CC=CC=C1 XXJFYRYKHCNOQK-UHFFFAOYSA-N 0.000 claims 2
- BIZYAOCWRROOTD-UHFFFAOYSA-N 2-[3,5-dicyano-6-[2-(diethylamino)ethyl-methylamino]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCN(CC)CC)SC(C(=O)N)C1=CC=CC=C1 BIZYAOCWRROOTD-UHFFFAOYSA-N 0.000 claims 2
- AXKAVBGAZHPOHC-UHFFFAOYSA-N 2-[3,5-dicyano-6-[2-(diethylaminomethyl)morpholin-4-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(OCC1)CN(CC)CC)SC(C(=O)N)C1=CC=CC=C1 AXKAVBGAZHPOHC-UHFFFAOYSA-N 0.000 claims 2
- QBTLPLHSROYOIB-UHFFFAOYSA-N 2-[3,5-dicyano-6-[2-(dimethylamino)ethoxy]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)OCCN(C)C)SC(C(=O)N)C1=CC=CC=C1 QBTLPLHSROYOIB-UHFFFAOYSA-N 0.000 claims 2
- CMFOAXMRKJAQAS-UHFFFAOYSA-N 2-[3,5-dicyano-6-[2-(dimethylamino)ethyl-methylamino]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N(C)CCN(C)C)SC(C(=O)N)C1=CC=CC=C1 CMFOAXMRKJAQAS-UHFFFAOYSA-N 0.000 claims 2
- XDSCOQKNRNKTDB-UHFFFAOYSA-N 2-[3,5-dicyano-6-[2-(dimethylamino)ethylsulfanyl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)SCCN(C)C)SC(C(=O)N)C1=CC=CC=C1 XDSCOQKNRNKTDB-UHFFFAOYSA-N 0.000 claims 2
- ZGBWULPYTNVDDE-UHFFFAOYSA-N 2-[3,5-dicyano-6-[3-(diaminomethylideneamino)oxyazetidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(C1)ONC(=N)N)SC(C(=O)N)C1=CC=CC=C1 ZGBWULPYTNVDDE-UHFFFAOYSA-N 0.000 claims 2
- OGHLVJPRXFDONV-UHFFFAOYSA-N 2-[3,5-dicyano-6-[3-[(dimethylamino)methyl]piperidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(CCC1)CN(C)C)SC(C(=O)N)C1=CC=CC=C1 OGHLVJPRXFDONV-UHFFFAOYSA-N 0.000 claims 2
- CPKKLVQNKMXDBL-UHFFFAOYSA-N 2-[3,5-dicyano-6-[3-[(dimethylamino)methyl]pyrrolidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CC(CC1)CN(C)C)SC(C(=O)N)C1=CC=CC=C1 CPKKLVQNKMXDBL-UHFFFAOYSA-N 0.000 claims 2
- NUOFNLUIHZRQHJ-UHFFFAOYSA-N 2-[3,5-dicyano-6-[4-(2,2-dimethylpropylamino)piperidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)NCC(C)(C)C)SC(C(=O)N)C1=CC=CC=C1 NUOFNLUIHZRQHJ-UHFFFAOYSA-N 0.000 claims 2
- OHYCOVOLCLJBIQ-UHFFFAOYSA-N 2-[3,5-dicyano-6-[4-(cyclobutylamino)piperidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)NC1CCC1)SC(C(=O)N)C1=CC=CC=C1 OHYCOVOLCLJBIQ-UHFFFAOYSA-N 0.000 claims 2
- WLGBTBSZMJKZFA-UHFFFAOYSA-N 2-[3,5-dicyano-6-[4-(cyclopropylamino)piperidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)NC1CC1)SC(C(=O)N)C1=CC=CC=C1 WLGBTBSZMJKZFA-UHFFFAOYSA-N 0.000 claims 2
- BUFHWVIJQMGNTB-UHFFFAOYSA-N 2-[3,5-dicyano-6-[4-(diaminomethylideneamino)oxypiperidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)ONC(=N)N)SC(C(=O)N)C1=CC=CC=C1 BUFHWVIJQMGNTB-UHFFFAOYSA-N 0.000 claims 2
- MELQQCMEXPGRLW-UHFFFAOYSA-N 2-[3,5-dicyano-6-[4-(dimethylamino)piperidin-1-yl]-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(#N)C=1C(=NC(=C(C=1CC)C#N)N1CCC(CC1)N(C)C)SC(C(=O)N)C1=CC=CC=C1 MELQQCMEXPGRLW-UHFFFAOYSA-N 0.000 claims 2
- MBQJFQOCMNTMNQ-UHFFFAOYSA-N 2-[4-(2-amino-2-oxoethyl)phenyl]-2-[3,5-dicyano-6-(dimethylamino)-4-ethylpyridin-2-yl]sulfanylacetamide Chemical compound NC(CC1=CC=C(C=C1)C(C(=O)N)SC1=NC(=C(C(=C1C#N)CC)C#N)N(C)C)=O MBQJFQOCMNTMNQ-UHFFFAOYSA-N 0.000 claims 2
- IKEVWYBPAUJEDN-UHFFFAOYSA-N 2-[6-(2-amino-2-oxoethyl)sulfanyl-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC(CSC1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N)=O IKEVWYBPAUJEDN-UHFFFAOYSA-N 0.000 claims 2
- ZGFSVDFCYOMEJY-UHFFFAOYSA-N 2-[6-(3-aminopiperidin-1-yl)-3,5-dicyano-4-cyclopropylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CN(CCC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)C1CC1)C#N ZGFSVDFCYOMEJY-UHFFFAOYSA-N 0.000 claims 2
- WOFWYIKKGDFRKO-UHFFFAOYSA-N 2-[6-(4-acetylpiperazin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(C)(=O)N1CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N WOFWYIKKGDFRKO-UHFFFAOYSA-N 0.000 claims 2
- BEWQRCQQIKNSEB-UHFFFAOYSA-N 2-[6-(4-amino-4-methylpiperidin-1-yl)-3,5-dicyano-4-cyclopropylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1(CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)C1CC1)C#N)C BEWQRCQQIKNSEB-UHFFFAOYSA-N 0.000 claims 2
- UTKLFRLMLLGCFI-UHFFFAOYSA-N 2-[6-(4-aminopiperidin-1-yl)-3,5-dicyano-4-cyclopropylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)C1CC1)C#N UTKLFRLMLLGCFI-UHFFFAOYSA-N 0.000 claims 2
- KNKHRZYILDZLRE-UHFFFAOYSA-N 2-[6-(4-aminopiperidin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N KNKHRZYILDZLRE-UHFFFAOYSA-N 0.000 claims 2
- OYAWXAXYBNYPBS-UHFFFAOYSA-N 2-[6-(4-aminopiperidin-1-yl)-3,5-dicyano-4-methoxypyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)OC)C#N OYAWXAXYBNYPBS-UHFFFAOYSA-N 0.000 claims 2
- UOBFRXJLZIFHJN-UHFFFAOYSA-N 2-[6-(4-aminopiperidin-1-yl)-3-cyano-4-ethyl-5-methylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C UOBFRXJLZIFHJN-UHFFFAOYSA-N 0.000 claims 2
- QPYOXRCZBIGMHI-UHFFFAOYSA-N 2-[6-(4-benzoylpiperazin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound C(C1=CC=CC=C1)(=O)N1CCN(CC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N QPYOXRCZBIGMHI-UHFFFAOYSA-N 0.000 claims 2
- SRZPYPCNFUTKLJ-UHFFFAOYSA-N 2-[6-(azetidin-1-yl)-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound N1(CCC1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N SRZPYPCNFUTKLJ-UHFFFAOYSA-N 0.000 claims 2
- WEGOHWICAIDWSC-UHFFFAOYSA-N 2-[6-[(2-amino-2-oxoethyl)-methylamino]-3,5-dicyano-4-cyclopropylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC(CN(C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)C1CC1)C#N)C)=O WEGOHWICAIDWSC-UHFFFAOYSA-N 0.000 claims 2
- QNAWNFWIFHMERM-UHFFFAOYSA-N 2-[6-[(2-amino-2-oxoethyl)-methylamino]-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC(CN(C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N)C)=O QNAWNFWIFHMERM-UHFFFAOYSA-N 0.000 claims 2
- PMWNNSZNZVXNKL-NYRJJRHWSA-N 2-[6-[(2R)-2-(aminomethyl)morpholin-4-yl]-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC[C@H]1OCCN(C1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N PMWNNSZNZVXNKL-NYRJJRHWSA-N 0.000 claims 2
- PMWNNSZNZVXNKL-FUKCDUGKSA-N 2-[6-[(2S)-2-(aminomethyl)morpholin-4-yl]-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC[C@@H]1OCCN(C1)C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N PMWNNSZNZVXNKL-FUKCDUGKSA-N 0.000 claims 2
- RNQDUYUPMICSPU-UHFFFAOYSA-N 2-[6-[(3-aminocyclobutyl)-methylamino]-3,5-dicyano-4-ethylpyridin-2-yl]sulfanyl-2-phenylacetamide Chemical compound NC1CC(C1)N(C1=C(C(=C(C(=N1)SC(C(=O)N)C1=CC=CC=C1)C#N)CC)C#N)C RNQDUYUPMICSPU-UHFFFAOYSA-N 0.000 claims 2
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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| EA034786B1 (ru) | 2015-08-13 | 2020-03-20 | Мерк Шарп И Доум Корп. | Циклические динуклеотидные соединения в качестве агонистов sting |
| US11453697B1 (en) | 2015-08-13 | 2022-09-27 | Merck Sharp & Dohme Llc | Cyclic di-nucleotide compounds as sting agonists |
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