HRP20131048T1 - Cikliäśki derivati kao modulatori aktivnosti receptora kemokina - Google Patents
Cikliäśki derivati kao modulatori aktivnosti receptora kemokina Download PDFInfo
- Publication number
- HRP20131048T1 HRP20131048T1 HRP20131048TT HRP20131048T HRP20131048T1 HR P20131048 T1 HRP20131048 T1 HR P20131048T1 HR P20131048T T HRP20131048T T HR P20131048TT HR P20131048 T HRP20131048 T HR P20131048T HR P20131048 T1 HRP20131048 T1 HR P20131048T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- amino
- isopropyl
- tert
- oxopyrrolidin
- Prior art date
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- 230000000694 effects Effects 0.000 title claims 6
- 102000009410 Chemokine receptor Human genes 0.000 title claims 2
- 108050000299 Chemokine receptor Proteins 0.000 title claims 2
- 125000004122 cyclic group Chemical group 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 29
- -1 carbocyclic radical Chemical class 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 21
- NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 125000005842 heteroatom Chemical group 0.000 claims 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 13
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 12
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 12
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 claims 12
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 10
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 9
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 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 6
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims 6
- GBLRQXKSCRCLBZ-YVQAASCFSA-N (1R,2S,1'R,2'S)-doxacurium Chemical compound COC1=C(OC)C(OC)=CC(C[C@H]2[N@+](CCC3=C2C(=C(OC)C(OC)=C3)OC)(C)CCCOC(=O)CCC(=O)OCCC[N@@+]2(C)[C@@H](C3=C(OC)C(OC)=C(OC)C=C3CC2)CC=2C=C(OC)C(OC)=C(OC)C=2)=C1 GBLRQXKSCRCLBZ-YVQAASCFSA-N 0.000 claims 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 125000001041 indolyl group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 201000006417 multiple sclerosis Diseases 0.000 claims 3
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 2
- VUTFQZRCOLEYDX-GAGAFAOGSA-N (3s)-1-[(1s,2r,4r)-4-[ethyl(propan-2-yl)amino]-2-(propan-2-ylsulfonylmethyl)cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)S(=O)(=O)C[C@@H]1C[C@H](N(C(C)C)CC)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 VUTFQZRCOLEYDX-GAGAFAOGSA-N 0.000 claims 2
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 2
- 206010001889 Alveolitis Diseases 0.000 claims 2
- 102100021943 C-C motif chemokine 2 Human genes 0.000 claims 2
- 101710155857 C-C motif chemokine 2 Proteins 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000005512 benztetrazolyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010009887 colitis Diseases 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims 2
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 230000003589 nefrotoxic effect Effects 0.000 claims 2
- 201000008383 nephritis Diseases 0.000 claims 2
- 231100000381 nephrotoxic Toxicity 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 210000002966 serum Anatomy 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- GGTXPWHBBKWWAU-KAORUIQYSA-N (3r)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-3-[[6-(trifluoromethyl)quinolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@H](NC=2C3=CC(=CC=C3N=CC=2)C(F)(F)F)CC1 GGTXPWHBBKWWAU-KAORUIQYSA-N 0.000 claims 1
- QDJNNUUXDKEKSK-DVWBAYGPSA-N (3s)-1-[(1r,2s,4s)-2-methoxy-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CO[C@H]1C[C@@H](N(C)C(C)C)CC[C@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QDJNNUUXDKEKSK-DVWBAYGPSA-N 0.000 claims 1
- JDSSVFGDHUHJLE-YVCBRDFCSA-N (3s)-1-[(1s,2r,4r)-2-(methoxymethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound COC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 JDSSVFGDHUHJLE-YVCBRDFCSA-N 0.000 claims 1
- QJQMEUAVQLMKRZ-REIYTJMXSA-N (3s)-1-[(1s,2r,4r)-2-(methoxymethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound COC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QJQMEUAVQLMKRZ-REIYTJMXSA-N 0.000 claims 1
- DOEJUJATHMUHEL-CIDQWEOVSA-N (3s)-1-[(1s,2r,4r)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[(6-chloroquinazolin-4-yl)amino]pyrrolidin-2-one Chemical compound CC(C)(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 DOEJUJATHMUHEL-CIDQWEOVSA-N 0.000 claims 1
- UGBYHTSFHVLWAY-CIDQWEOVSA-N (3s)-1-[(1s,2r,4r)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 UGBYHTSFHVLWAY-CIDQWEOVSA-N 0.000 claims 1
- ZILPZMJIIYWEIE-IIPCHUTBSA-N (3s)-1-[(1s,2r,4r)-2-ethyl-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 ZILPZMJIIYWEIE-IIPCHUTBSA-N 0.000 claims 1
- QDJNNUUXDKEKSK-MBPVOVBZSA-N (3s)-1-[(1s,2r,4r)-2-methoxy-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CO[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QDJNNUUXDKEKSK-MBPVOVBZSA-N 0.000 claims 1
- HPPBSQCQNSEBDB-GIHONLOASA-N (3s)-1-[(1s,2r,4r)-4-(diethylamino)-2-propylcyclohexyl]-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(CC)CC)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 HPPBSQCQNSEBDB-GIHONLOASA-N 0.000 claims 1
- ZNHBWLSZPPXUQJ-GNRVTEMESA-N (3s)-1-[(1s,2r,4r)-4-(diethylamino)-2-propylcyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(CC)CC)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 ZNHBWLSZPPXUQJ-GNRVTEMESA-N 0.000 claims 1
- YYCQIDWQINLVGT-SZUBIPLGSA-N (3s)-1-[(1s,2r,4r)-4-(dimethylamino)-2-propylcyclohexyl]-3-[[6-(2-methoxyphenyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C=2C(=CC=CC=2)OC)CC1 YYCQIDWQINLVGT-SZUBIPLGSA-N 0.000 claims 1
- IGPPRIHSIXZQKE-RFZJPIJTSA-N (3s)-1-[(1s,2r,4r)-4-(dimethylamino)-2-propylcyclohexyl]-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 IGPPRIHSIXZQKE-RFZJPIJTSA-N 0.000 claims 1
- IUMMGHHWZNCPLL-SLWXAUBPSA-N (3s)-1-[(1s,2r,4r)-4-(dimethylamino)-2-propylcyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 IUMMGHHWZNCPLL-SLWXAUBPSA-N 0.000 claims 1
- DDMIUZIWMIRUDD-IIPCHUTBSA-N (3s)-1-[(1s,2r,4r)-4-(tert-butylamino)-2-propylcyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 DDMIUZIWMIRUDD-IIPCHUTBSA-N 0.000 claims 1
- GRTCZZMPNUJSBW-IKVMQTKTSA-N (3s)-1-[(1s,2r,4r)-4-[ethyl(propan-2-yl)amino]-2-(propan-2-ylsulfonylmethyl)cyclohexyl]-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)S(=O)(=O)C[C@@H]1C[C@H](N(C(C)C)CC)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 GRTCZZMPNUJSBW-IKVMQTKTSA-N 0.000 claims 1
- CJGHKRWUTQLMOP-REIYTJMXSA-N (3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 CJGHKRWUTQLMOP-REIYTJMXSA-N 0.000 claims 1
- JDGLGHFGXNBWKY-PLWWPAAYSA-N (3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(propan-2-ylsulfonylmethyl)cyclohexyl]-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 JDGLGHFGXNBWKY-PLWWPAAYSA-N 0.000 claims 1
- KJRSHBWEIJVIPK-CIDQWEOVSA-N (3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(propan-2-ylsulfonylmethyl)cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 KJRSHBWEIJVIPK-CIDQWEOVSA-N 0.000 claims 1
- DYHKMKNGPQGDFI-GIHONLOASA-N (3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 DYHKMKNGPQGDFI-GIHONLOASA-N 0.000 claims 1
- NUJWKQSEJDYCDB-GNRVTEMESA-N (3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 NUJWKQSEJDYCDB-GNRVTEMESA-N 0.000 claims 1
- GGTXPWHBBKWWAU-ZBXIDMRXSA-N (3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-3-[[6-(trifluoromethyl)quinolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CC=2)C(F)(F)F)CC1 GGTXPWHBBKWWAU-ZBXIDMRXSA-N 0.000 claims 1
- DDMIUZIWMIRUDD-QQOZLPODSA-N (3s)-1-[(1s,2r,4s)-4-(tert-butylamino)-2-propylcyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 DDMIUZIWMIRUDD-QQOZLPODSA-N 0.000 claims 1
- LANSWOXPCGGIDN-GNRVTEMESA-N (3s)-1-[(1s,2s,4r)-2-(2-methoxyethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound COCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 LANSWOXPCGGIDN-GNRVTEMESA-N 0.000 claims 1
- WURFNVVNKHPVBR-FUAMJQMHSA-N (3s)-1-[(1s,2s,4r)-4-[methyl(propan-2-yl)amino]-2-propan-2-ylcyclohexyl]-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 WURFNVVNKHPVBR-FUAMJQMHSA-N 0.000 claims 1
- MTBTXJDOIZCIGH-FUKQBSRTSA-N (3s)-1-[(1s,2s,4r)-4-[methyl(propan-2-yl)amino]-2-propan-2-ylcyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 MTBTXJDOIZCIGH-FUKQBSRTSA-N 0.000 claims 1
- MTBTXJDOIZCIGH-ZZTDLJEGSA-N (3s)-1-[(1s,2s,4s)-4-[methyl(propan-2-yl)amino]-2-propan-2-ylcyclohexyl]-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-2-one Chemical compound CC(C)[C@@H]1C[C@@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 MTBTXJDOIZCIGH-ZZTDLJEGSA-N 0.000 claims 1
- QRYBVFBEZKQLNV-REIYTJMXSA-N (3s)-3-[(6-chloroquinazolin-4-yl)amino]-1-[(1s,2r,4r)-2-(methoxymethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]pyrrolidin-2-one Chemical compound COC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 QRYBVFBEZKQLNV-REIYTJMXSA-N 0.000 claims 1
- VDUDGTQPNCGUJV-IIPCHUTBSA-N (3s)-3-[(6-chloroquinazolin-4-yl)amino]-1-[(1s,2r,4r)-4-(propan-2-ylamino)-2-propylcyclohexyl]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](NC(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 VDUDGTQPNCGUJV-IIPCHUTBSA-N 0.000 claims 1
- ADFQYWQOGVHSME-REIYTJMXSA-N (3s)-3-[(6-chloroquinazolin-4-yl)amino]-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]pyrrolidin-2-one Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 ADFQYWQOGVHSME-REIYTJMXSA-N 0.000 claims 1
- DEXJQUDODNDJEZ-GNRVTEMESA-N (3s)-3-[(6-chloroquinazolin-4-yl)amino]-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 DEXJQUDODNDJEZ-GNRVTEMESA-N 0.000 claims 1
- FIQWQSQKPPDHEM-KUHDOKTFSA-N (3s)-3-[(6-chloroquinazolin-4-yl)amino]-1-[(1s,2r,4s)-4-[ethyl(propan-2-yl)amino]-2-propylcyclohexyl]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@@H](N(CC)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 FIQWQSQKPPDHEM-KUHDOKTFSA-N 0.000 claims 1
- GGFIAPCTULKLKC-FUKQBSRTSA-N (3s)-3-[(6-chloroquinazolin-4-yl)amino]-1-[(1s,2s,4r)-4-[methyl(propan-2-yl)amino]-2-propan-2-ylcyclohexyl]pyrrolidin-2-one Chemical compound CC(C)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 GGFIAPCTULKLKC-FUKQBSRTSA-N 0.000 claims 1
- REQCAJAZXKNXLL-GNRVTEMESA-N (3s)-3-[(6-fluoroquinazolin-4-yl)amino]-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(F)=CC=C3N=CN=2)CC1 REQCAJAZXKNXLL-GNRVTEMESA-N 0.000 claims 1
- HJSKAGLDLFHIGB-XSYGEPLQSA-N (3s)-3-[(6-tert-butylpyrimido[5,4-d]pyrimidin-4-yl)amino]-1-[(1s,2r,4r)-4-(dimethylamino)-2-propylcyclohexyl]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=NC(=NC=C3N=CN=2)C(C)(C)C)CC1 HJSKAGLDLFHIGB-XSYGEPLQSA-N 0.000 claims 1
- RGBQAKKWKWSVRL-YQHHHJOQSA-N (3s)-3-[[6-(2-methoxyphenyl)quinazolin-4-yl]amino]-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]pyrrolidin-2-one Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C=2C(=CC=CC=2)OC)CC1 RGBQAKKWKWSVRL-YQHHHJOQSA-N 0.000 claims 1
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- VRXHQZREFIDXHU-AANQFLQQSA-N 1-methyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(propan-2-ylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]indole-2-carboxamide Chemical compound CC(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N(C3=CC=CC=C3C=2)C)CC1 VRXHQZREFIDXHU-AANQFLQQSA-N 0.000 claims 1
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- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- WBTVYZRDXKTLKT-YNGFEMSNSA-N 2-(cyclopropylcarbamoylamino)-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethyl)benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NC(=O)NC2CC2)CC1 WBTVYZRDXKTLKT-YNGFEMSNSA-N 0.000 claims 1
- DAGJQQQPIJRRQT-IHIBHSRISA-N 2-(ethylcarbamoylamino)-n-[(3s)-1-[(1s,2r,4r)-2-(methoxymethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethyl)benzamide Chemical compound CCNC(=O)NC1=CC=C(C(F)(F)F)C=C1C(=O)N[C@@H]1C(=O)N([C@@H]2[C@@H](C[C@@H](CC2)N(C)C(C)C)COC)CC1 DAGJQQQPIJRRQT-IHIBHSRISA-N 0.000 claims 1
- NIGNHDUWKZDZLS-YKBLPDKLSA-N 2-(ethylcarbamoylamino)-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethyl)benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NC(=O)NCC)CC1 NIGNHDUWKZDZLS-YKBLPDKLSA-N 0.000 claims 1
- DPLHSLFLMLESDN-GNRVTEMESA-N 2-(methanesulfonamido)-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethyl)benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NS(C)(=O)=O)CC1 DPLHSLFLMLESDN-GNRVTEMESA-N 0.000 claims 1
- STHNDGFAUHHZPJ-WKZKVMAPSA-N 2-amino-n-[(3s)-1-[(1s,2r,4r)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethoxy)benzamide Chemical compound CC(C)(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C(=CC=C(OC(F)(F)F)C=2)N)CC1 STHNDGFAUHHZPJ-WKZKVMAPSA-N 0.000 claims 1
- KYEVTHKPFTUPMM-GQSCTRQFSA-N 2-amino-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethoxy)benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C(=CC=C(OC(F)(F)F)C=2)N)CC1 KYEVTHKPFTUPMM-GQSCTRQFSA-N 0.000 claims 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 1
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- ZIJADGCGWMSBPR-WKDRNLAYSA-N 2-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]pyrimidine-4-carboxamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(N=CC=2)C(C)(C)C)CC1 ZIJADGCGWMSBPR-WKDRNLAYSA-N 0.000 claims 1
- DAIYEMOYRVDTRP-XMURLOJTSA-N 2-tert-butyl-n-[1-[(1s,2r,4r)-2-(1-hydroxypropyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]pyrimidine-4-carboxamide Chemical compound CCC(O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)C(NC(=O)C=2N=C(N=CC=2)C(C)(C)C)CC1 DAIYEMOYRVDTRP-XMURLOJTSA-N 0.000 claims 1
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- HJDICAXROWGRHE-CZGNIMDHSA-N 3-[(1s,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[3-(trifluoromethyl)benzoyl]amino]pyrrolidin-1-yl]cyclohexyl]propanoic acid Chemical compound OC(=O)CC[C@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 HJDICAXROWGRHE-CZGNIMDHSA-N 0.000 claims 1
- ADZGQOOPSMBOBF-HHGOQMMWSA-N 3-[4-[[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]amino]quinazolin-6-yl]benzonitrile Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C=2C=C(C=CC=2)C#N)CC1 ADZGQOOPSMBOBF-HHGOQMMWSA-N 0.000 claims 1
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- GEOVCGHMHBQHKL-CZGNIMDHSA-N 3-fluoro-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=C(F)C=2)C(F)(F)F)CC1 GEOVCGHMHBQHKL-CZGNIMDHSA-N 0.000 claims 1
- PGZPXHNORRTSBB-ZXMXYHOLSA-N 3-tert-butyl-4-hydroxy-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(O)=CC=2)C(C)(C)C)CC1 PGZPXHNORRTSBB-ZXMXYHOLSA-N 0.000 claims 1
- SVNIBIDJSNMYNV-VHXCZSFDSA-N 3-tert-butyl-5-[[(3s)-1-[(1s,2r,4r)-2-(ethylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]carbamoyl]benzoic acid Chemical compound CCS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=C(C=2)C(O)=O)C(C)(C)C)CC1 SVNIBIDJSNMYNV-VHXCZSFDSA-N 0.000 claims 1
- GTGOJOCBSZQQMV-HVVFZDMJSA-N 3-tert-butyl-5-[[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]carbamoyl]benzoic acid Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=C(C=2)C(O)=O)C(C)(C)C)CC1 GTGOJOCBSZQQMV-HVVFZDMJSA-N 0.000 claims 1
- BUFSZUZKTQLIRG-VRUIKYSZSA-N 3-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-4-hydroxybenzamide Chemical compound CC(C)(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(O)=CC=2)C(C)(C)C)CC1 BUFSZUZKTQLIRG-VRUIKYSZSA-N 0.000 claims 1
- ZAYUWNOQQYDPBS-IVOMFYJKSA-N 3-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-4-(dimethylamino)-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-4-hydroxybenzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(O)=CC=2)C(C)(C)C)CC1 ZAYUWNOQQYDPBS-IVOMFYJKSA-N 0.000 claims 1
- KMTYDBXWIODFGQ-KMQNXVAFSA-N 3-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-4-[ethyl(propan-2-yl)amino]-2-(propan-2-ylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]benzamide Chemical compound CC(C)S(=O)(=O)C[C@@H]1C[C@H](N(C(C)C)CC)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(C)(C)C)CC1 KMTYDBXWIODFGQ-KMQNXVAFSA-N 0.000 claims 1
- HLRAWMGOLABNON-IGABQKFOSA-N 3-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(C)(C)C)CC1 HLRAWMGOLABNON-IGABQKFOSA-N 0.000 claims 1
- HLKNYNKFFPVBFM-GATIMQMVSA-N 3-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(C)(C)C)CC1 HLKNYNKFFPVBFM-GATIMQMVSA-N 0.000 claims 1
- AYICHJPUUFFCNV-JWWGGVBKSA-N 4-chloro-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(Cl)=CC=2)C(F)(F)F)CC1 AYICHJPUUFFCNV-JWWGGVBKSA-N 0.000 claims 1
- FRNSOYQFHDEBCE-CIOIWQPASA-N 4-hydroxy-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-3-phenylbenzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(O)=CC=2)C=2C=CC=CC=2)CC1 FRNSOYQFHDEBCE-CIOIWQPASA-N 0.000 claims 1
- VQUGRAMPRAKKNU-MXNKGDRCSA-N 4-methyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(C)=CC=2)C(F)(F)F)CC1 VQUGRAMPRAKKNU-MXNKGDRCSA-N 0.000 claims 1
- YGXTWIZVIIYMTK-YRPNKDGESA-N 5-tert-butyl-2-methyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]pyrazole-3-carboxamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N(N=C(C=2)C(C)(C)C)C)CC1 YGXTWIZVIIYMTK-YRPNKDGESA-N 0.000 claims 1
- ZASIXQLHCIHBBA-LRSLUSHPSA-N 5-tert-butyl-2-methyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(propan-2-ylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]pyrazole-3-carboxamide Chemical compound CC(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N(N=C(C=2)C(C)(C)C)C)CC1 ZASIXQLHCIHBBA-LRSLUSHPSA-N 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- CXZHVHDUTKBDFQ-WKDRNLAYSA-N 6-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-2-(2-hydroxypropan-2-yl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]pyridine-2-carboxamide Chemical compound CC(O)(C)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(C=CC=2)C(C)(C)C)CC1 CXZHVHDUTKBDFQ-WKDRNLAYSA-N 0.000 claims 1
- LBDNVIMPANYCRT-SCPDWHHUSA-N 6-tert-butyl-n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]pyridine-2-carboxamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(C=CC=2)C(C)(C)C)CC1 LBDNVIMPANYCRT-SCPDWHHUSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 108700028369 Alleles Chemical group 0.000 claims 1
- 206010002329 Aneurysm Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 claims 1
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 claims 1
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 claims 1
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 claims 1
- 102100023702 C-C motif chemokine 13 Human genes 0.000 claims 1
- 101710112613 C-C motif chemokine 13 Proteins 0.000 claims 1
- 102100032367 C-C motif chemokine 5 Human genes 0.000 claims 1
- 102100032366 C-C motif chemokine 7 Human genes 0.000 claims 1
- 101710155834 C-C motif chemokine 7 Proteins 0.000 claims 1
- 102100034871 C-C motif chemokine 8 Human genes 0.000 claims 1
- 101710155833 C-C motif chemokine 8 Proteins 0.000 claims 1
- UVYZSNRLSUFFDP-BJLQDIEVSA-N CC(C)(C)N[C@H]1CC[C@@H](CC1)N1CC[C@H](NC(=O)c2ccc(O)c(c2)C(C)(C)C)C1=O Chemical compound CC(C)(C)N[C@H]1CC[C@@H](CC1)N1CC[C@H](NC(=O)c2ccc(O)c(c2)C(C)(C)C)C1=O UVYZSNRLSUFFDP-BJLQDIEVSA-N 0.000 claims 1
- VTZDTCPRYCUTDK-BXWFABGCSA-N CC(C)(C)N[C@H]1CC[C@@H](CC1)N1CC[C@H](Nc2ncnc3ccc(cc23)C(F)(F)F)C1=O Chemical compound CC(C)(C)N[C@H]1CC[C@@H](CC1)N1CC[C@H](Nc2ncnc3ccc(cc23)C(F)(F)F)C1=O VTZDTCPRYCUTDK-BXWFABGCSA-N 0.000 claims 1
- ZQEFOMJJNBIMPC-PUHABZHSSA-N CC(C)N(C)[C@H](CC1)C[C@@H](CS(C(C)(C)C)(=O)=O)[C@H]1N(CC[C@@H]1N(C(C2=CN=CC(C3=CC=CC=C3)=C2)=O)O)C1=O Chemical compound CC(C)N(C)[C@H](CC1)C[C@@H](CS(C(C)(C)C)(=O)=O)[C@H]1N(CC[C@@H]1N(C(C2=CN=CC(C3=CC=CC=C3)=C2)=O)O)C1=O ZQEFOMJJNBIMPC-PUHABZHSSA-N 0.000 claims 1
- LMAHMOPDJPDTOI-CIOIWQPASA-N CCC[C@H](C[C@@H](CC1)N(C)C(C)C)[C@H]1N(CC[C@@H]1N(C(C2=CC=NC(C3=CC=CC=C3)=C2)=O)O)C1=O Chemical compound CCC[C@H](C[C@@H](CC1)N(C)C(C)C)[C@H]1N(CC[C@@H]1N(C(C2=CC=NC(C3=CC=CC=C3)=C2)=O)O)C1=O LMAHMOPDJPDTOI-CIOIWQPASA-N 0.000 claims 1
- 102000004274 CCR5 Receptors Human genes 0.000 claims 1
- 108010017088 CCR5 Receptors Proteins 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 102000001326 Chemokine CCL4 Human genes 0.000 claims 1
- 108010055165 Chemokine CCL4 Proteins 0.000 claims 1
- 108010055166 Chemokine CCL5 Proteins 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
- 208000031886 HIV Infections Diseases 0.000 claims 1
- 208000037357 HIV infectious disease Diseases 0.000 claims 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 101000978374 Mus musculus C-C motif chemokine 12 Proteins 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 claims 1
- 244000250129 Trigonella foenum graecum Species 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 1
- 125000003971 isoxazolinyl group Chemical group 0.000 claims 1
- AEUKDPKXTPNBNY-XEYRWQBLSA-N mcp 2 Chemical compound C([C@@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CS)NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)C1=CC=CC=C1 AEUKDPKXTPNBNY-XEYRWQBLSA-N 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- ICEODVBGOLGGAG-MGBDSLLKSA-N methyl (1R,2S,5R)-2-[(3S)-3-[(2-tert-butyl-1H-pyridine-2-carbonyl)amino]-2-oxopyrrolidin-1-yl]-5-[methyl(propan-2-yl)amino]cyclohexane-1-carboxylate Chemical compound C(C)(C)(C)C1(NC=CC=C1)C(=O)N[C@@H]1C(N(CC1)[C@@H]1[C@@H](C[C@@H](CC1)N(C)C(C)C)C(=O)OC)=O ICEODVBGOLGGAG-MGBDSLLKSA-N 0.000 claims 1
- DIEFYRYLWZHRAQ-ZRNYENFQSA-N methyl (1r,2s,5r)-2-[(3s)-3-[[3-fluoro-5-(trifluoromethyl)benzoyl]amino]-2-oxopyrrolidin-1-yl]-5-[methyl(propan-2-yl)amino]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=C(F)C=2)C(F)(F)F)CC1 DIEFYRYLWZHRAQ-ZRNYENFQSA-N 0.000 claims 1
- KLLFANHCCISSCD-BNDYYXHWSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[(2-phenyl-1,3-thiazole-4-carbonyl)amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(SC=2)C=2C=CC=CC=2)CC1 KLLFANHCCISSCD-BNDYYXHWSA-N 0.000 claims 1
- GNBQCQRWZOFCLF-BNDYYXHWSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[(3-phenyl-1,2-oxazole-5-carbonyl)amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2ON=C(C=2)C=2C=CC=CC=2)CC1 GNBQCQRWZOFCLF-BNDYYXHWSA-N 0.000 claims 1
- QZPXJSMZGGAOQF-BNDYYXHWSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[(4-phenyl-1,3-thiazole-2-carbonyl)amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2SC=C(N=2)C=2C=CC=CC=2)CC1 QZPXJSMZGGAOQF-BNDYYXHWSA-N 0.000 claims 1
- MOUQTDZEOLFDOO-CZYKHXBRSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[(4-phenylfuran-2-carbonyl)amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC=C(C=2)C=2C=CC=CC=2)CC1 MOUQTDZEOLFDOO-CZYKHXBRSA-N 0.000 claims 1
- ZKMURXGKMILLKL-UGTOYMOASA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[(6-phenylpyrazine-2-carbonyl)amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(C=NC=2)C=2C=CC=CC=2)CC1 ZKMURXGKMILLKL-UGTOYMOASA-N 0.000 claims 1
- GULNECQGYQKNRC-YRXWBPOGSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[3-(trifluoromethyl)benzoyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 GULNECQGYQKNRC-YRXWBPOGSA-N 0.000 claims 1
- PDAVOOLBPXNXMW-MQYQWHSLSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[4-(1,1,2,2,2-pentafluoroethyl)-1,3-thiazole-2-carbonyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2SC=C(N=2)C(F)(F)C(F)(F)F)CC1 PDAVOOLBPXNXMW-MQYQWHSLSA-N 0.000 claims 1
- ZJBXVMDYVTVPMX-CZYKHXBRSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[4-[4-(trifluoromethyl)phenyl]furan-2-carbonyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC=C(C=2)C=2C=CC(=CC=2)C(F)(F)F)CC1 ZJBXVMDYVTVPMX-CZYKHXBRSA-N 0.000 claims 1
- GUUVMVVNERRMLF-KBXIAJHMSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[5-(trifluoromethyl)furan-2-carbonyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C(F)(F)F)CC1 GUUVMVVNERRMLF-KBXIAJHMSA-N 0.000 claims 1
- YTGLEBFANDDICO-CGXNFDGLSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[5-[3-(trifluoromethyl)phenyl]furan-2-carbonyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C=2C=C(C=CC=2)C(F)(F)F)CC1 YTGLEBFANDDICO-CGXNFDGLSA-N 0.000 claims 1
- PLSYSFZNEWCRHF-JBCDFXQESA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 PLSYSFZNEWCRHF-JBCDFXQESA-N 0.000 claims 1
- WGSWFANUTZOQPJ-JBPLPALLSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[(2-methyl-5-phenylpyrazole-3-carbonyl)amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N(N=C(C=2)C=2C=CC=CC=2)C)CC1 WGSWFANUTZOQPJ-JBPLPALLSA-N 0.000 claims 1
- LLHPWLURFZXCHM-FPAYPSAMSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[(2-tert-butylpyrimidine-4-carbonyl)amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(N=CC=2)C(C)(C)C)CC1 LLHPWLURFZXCHM-FPAYPSAMSA-N 0.000 claims 1
- MGCWLLSAWNZNKG-QCFAMHMHSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[(3-tert-butyl-4-hydroxybenzoyl)amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(O)=CC=2)C(C)(C)C)CC1 MGCWLLSAWNZNKG-QCFAMHMHSA-N 0.000 claims 1
- RQLATVDREZFAII-CZYKHXBRSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[(3-tert-butylbenzoyl)amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(C)(C)C)CC1 RQLATVDREZFAII-CZYKHXBRSA-N 0.000 claims 1
- MJZCPWBWLLTWJU-LMCOJAPRSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[(5-tert-butyl-2-methylfuran-3-carbonyl)amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C2=C(OC(=C2)C(C)(C)C)C)CC1 MJZCPWBWLLTWJU-LMCOJAPRSA-N 0.000 claims 1
- JCZGMZDQISMMIK-BEKAIBRUSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[(6-chloroquinazolin-4-yl)amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(Cl)=CC=C3N=CN=2)CC1 JCZGMZDQISMMIK-BEKAIBRUSA-N 0.000 claims 1
- FCTCDYLYKKLYGE-VXNCWWDNSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[(6-tert-butylpyrimido[5,4-d]pyrimidin-4-yl)amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=NC(=NC=C3N=CN=2)C(C)(C)C)CC1 FCTCDYLYKKLYGE-VXNCWWDNSA-N 0.000 claims 1
- ALISOMWQABRTBC-BNDYYXHWSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[[2-(4-chlorophenyl)-1,3-thiazole-4-carbonyl]amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(SC=2)C=2C=CC(Cl)=CC=2)CC1 ALISOMWQABRTBC-BNDYYXHWSA-N 0.000 claims 1
- WDXBPJPKKHNPIF-JYWFKMLOSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[[5-(3,4-difluorophenyl)furan-2-carbonyl]amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C=2C=C(F)C(F)=CC=2)CC1 WDXBPJPKKHNPIF-JYWFKMLOSA-N 0.000 claims 1
- WVLHYOUBKKMFAX-CZYKHXBRSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[[5-(3-cyanophenyl)furan-2-carbonyl]amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C=2C=C(C=CC=2)C#N)CC1 WVLHYOUBKKMFAX-CZYKHXBRSA-N 0.000 claims 1
- XNWMABOBQOSLQY-CGXNFDGLSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[[5-(4-fluorophenyl)furan-2-carbonyl]amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C=2C=CC(F)=CC=2)CC1 XNWMABOBQOSLQY-CGXNFDGLSA-N 0.000 claims 1
- LFVHQGHTVFFDCS-LMQGHGSNSA-N methyl (1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-3-[[5-[2-chloro-5-(trifluoromethyl)phenyl]furan-2-carbonyl]amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C=2C(=CC=C(C=2)C(F)(F)F)Cl)CC1 LFVHQGHTVFFDCS-LMQGHGSNSA-N 0.000 claims 1
- YDHXMJINFVSQPV-ZRNYENFQSA-N methyl (1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[3-(trifluoromethyl)benzoyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 YDHXMJINFVSQPV-ZRNYENFQSA-N 0.000 claims 1
- QNCHTAGCNPZEQH-NXXWWENFSA-N methyl (1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 QNCHTAGCNPZEQH-NXXWWENFSA-N 0.000 claims 1
- UTMWITQECWBUAF-LMQGHGSNSA-N methyl (1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 UTMWITQECWBUAF-LMQGHGSNSA-N 0.000 claims 1
- FFPTVPJNQOLONW-ZRNYENFQSA-N methyl (1r,2s,5r)-5-[tert-butyl(methyl)amino]-2-[(3s)-2-oxo-3-[[3-(trifluoromethyl)benzoyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 FFPTVPJNQOLONW-ZRNYENFQSA-N 0.000 claims 1
- RURACEGWGNZEJQ-NXXWWENFSA-N methyl (1r,2s,5r)-5-[tert-butyl(methyl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethoxy)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(OC(F)(F)F)=CC=C3N=CN=2)CC1 RURACEGWGNZEJQ-NXXWWENFSA-N 0.000 claims 1
- CIVMIQAHLXLBGZ-LMQGHGSNSA-N methyl (1r,2s,5r)-5-[tert-butyl(methyl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 CIVMIQAHLXLBGZ-LMQGHGSNSA-N 0.000 claims 1
- PCHMFFADYGHDID-CZYKHXBRSA-N methyl (1r,2s,5r)-5-[tert-butyl(methyl)amino]-2-[(3s)-3-[[5-(4-chlorophenyl)furan-2-carbonyl]amino]-2-oxopyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@H](N(C)C(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C=2C=CC(Cl)=CC=2)CC1 PCHMFFADYGHDID-CZYKHXBRSA-N 0.000 claims 1
- GULNECQGYQKNRC-RDGPPVDQSA-N methyl (1r,2s,5s)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[3-(trifluoromethyl)benzoyl]amino]pyrrolidin-1-yl]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@@H]1C[C@@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 GULNECQGYQKNRC-RDGPPVDQSA-N 0.000 claims 1
- NVXDHOUIFDBQSQ-MLNNCEHLSA-N methyl (1s,2s,5r)-2-[(3s)-3-[[5-(4-chlorophenyl)furan-2-carbonyl]amino]-2-oxopyrrolidin-1-yl]-5-[methyl(propan-2-yl)amino]cyclohexane-1-carboxylate Chemical compound COC(=O)[C@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2OC(=CC=2)C=2C=CC(Cl)=CC=2)CC1 NVXDHOUIFDBQSQ-MLNNCEHLSA-N 0.000 claims 1
- YJHYVPSQSMGPHA-ZDULRJDPSA-N methyl 3-tert-butyl-5-[[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]carbamoyl]benzoate Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=C(C=2)C(=O)OC)C(C)(C)C)CC1 YJHYVPSQSMGPHA-ZDULRJDPSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- YBEHVCFTKMBBRR-CGXNFDGLSA-N n-[(3s)-1-[(1s,2r,4r)-2-(2-hydroxypropan-2-yl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CC(O)(C)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 YBEHVCFTKMBBRR-CGXNFDGLSA-N 0.000 claims 1
- BGXXPILYOXMBOB-CIDQWEOVSA-N n-[(3s)-1-[(1s,2r,4r)-2-(ethoxymethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-2-(ethylcarbamoylamino)-5-(trifluoromethyl)benzamide Chemical compound CCNC(=O)NC1=CC=C(C(F)(F)F)C=C1C(=O)N[C@@H]1C(=O)N([C@@H]2[C@@H](C[C@@H](CC2)N(C)C(C)C)COCC)CC1 BGXXPILYOXMBOB-CIDQWEOVSA-N 0.000 claims 1
- PNFYVFLTAQSWCO-FKVLARQCSA-N n-[(3s)-1-[(1s,2r,4r)-2-(ethoxymethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CCOC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 PNFYVFLTAQSWCO-FKVLARQCSA-N 0.000 claims 1
- VPQJUCNKBPHRCP-FKVLARQCSA-N n-[(3s)-1-[(1s,2r,4r)-2-(ethylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CCS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 VPQJUCNKBPHRCP-FKVLARQCSA-N 0.000 claims 1
- IJGUMSCZVYOVTC-MQFRRQCYSA-N n-[(3s)-1-[(1s,2r,4r)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethoxy)benzamide Chemical compound CC(C)(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(OC(F)(F)F)C=CC=2)CC1 IJGUMSCZVYOVTC-MQFRRQCYSA-N 0.000 claims 1
- GQRNJMIZAVHYCF-MALNDZBISA-N n-[(3s)-1-[(1s,2r,4r)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CC(C)(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 GQRNJMIZAVHYCF-MALNDZBISA-N 0.000 claims 1
- LCRQLTUHUPJEOG-YDLSIGKMSA-N n-[(3s)-1-[(1s,2r,4r)-2-(tert-butylsulfonylmethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-4-fluoro-3-(trifluoromethyl)benzamide Chemical compound CC(C)(C)S(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C(F)=CC=2)C(F)(F)F)CC1 LCRQLTUHUPJEOG-YDLSIGKMSA-N 0.000 claims 1
- BRQYEGIGNRTWEA-XCLNPWKQSA-N n-[(3s)-1-[(1s,2r,4r)-2-methyl-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 BRQYEGIGNRTWEA-XCLNPWKQSA-N 0.000 claims 1
- ANXWHQQGNJFKHO-NRDMVMEKSA-N n-[(3s)-1-[(1s,2r,4r)-4-(2,2-dimethylpropylamino)-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](NCC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 ANXWHQQGNJFKHO-NRDMVMEKSA-N 0.000 claims 1
- RSPQIEVMFSYUNX-XCLNPWKQSA-N n-[(3s)-1-[(1s,2r,4r)-4-(dimethylamino)-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 RSPQIEVMFSYUNX-XCLNPWKQSA-N 0.000 claims 1
- GBCVEIWZFPCXRP-FKVLARQCSA-N n-[(3s)-1-[(1s,2r,4r)-4-[ethyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C(C)C)CC)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 GBCVEIWZFPCXRP-FKVLARQCSA-N 0.000 claims 1
- KZYUPKXEHNEFIY-NRDMVMEKSA-N n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 KZYUPKXEHNEFIY-NRDMVMEKSA-N 0.000 claims 1
- DOXRNZDBWSJRKA-XUJYPJAKSA-N n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-3-phenylbenzamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C=2C=CC=CC=2)CC1 DOXRNZDBWSJRKA-XUJYPJAKSA-N 0.000 claims 1
- IVXIGEJNHPAUSE-MTQWNXOMSA-N n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-6-phenylpyrazine-2-carboxamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(C=NC=2)C=2C=CC=CC=2)CC1 IVXIGEJNHPAUSE-MTQWNXOMSA-N 0.000 claims 1
- SULJXHZZZYQUCJ-DDOAZUFRSA-N n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-(methylsulfonylmethyl)cyclohexyl]-2-oxopyrrolidin-3-yl]-6-phenylpyridine-2-carboxamide Chemical compound CS(=O)(=O)C[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2N=C(C=CC=2)C=2C=CC=CC=2)CC1 SULJXHZZZYQUCJ-DDOAZUFRSA-N 0.000 claims 1
- MWBKHKYLQFMZSK-GFRNBQLOSA-N n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 MWBKHKYLQFMZSK-GFRNBQLOSA-N 0.000 claims 1
- CBEQVCDYVLBOHA-OIIADRAWSA-N n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-3-phenylbenzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C=C(C=CC=2)C=2C=CC=CC=2)CC1 CBEQVCDYVLBOHA-OIIADRAWSA-N 0.000 claims 1
- TZPXDPKKJMIGOG-IIPCHUTBSA-N n-[(3s)-1-[(1s,2r,4r)-4-[methyl(propan-2-yl)amino]-2-propylcyclohexyl]-2-oxopyrrolidin-3-yl]-5-(trifluoromethyl)-2-(trifluoromethylsulfonylamino)benzamide Chemical compound CCC[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC(=O)C=2C(=CC=C(C=2)C(F)(F)F)NS(=O)(=O)C(F)(F)F)CC1 TZPXDPKKJMIGOG-IIPCHUTBSA-N 0.000 claims 1
- BOBQSVHLUMRRHE-GFKNVZDQSA-N n-[1-[(1s,2r,4r)-2-(1-hydroxyethyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CC(O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)C(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 BOBQSVHLUMRRHE-GFKNVZDQSA-N 0.000 claims 1
- LROXJTOGZMMCKN-MICNXPBNSA-N n-[1-[(1s,2r,4r)-2-(1-hydroxypropyl)-4-[methyl(propan-2-yl)amino]cyclohexyl]-2-oxopyrrolidin-3-yl]-3-(trifluoromethyl)benzamide Chemical compound CCC(O)[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)C(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)CC1 LROXJTOGZMMCKN-MICNXPBNSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
- HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
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Claims (21)
1. Spoj formule (Ia):
[image]
ili njegov stereoizomer ili farmaceutski prihvatljiva sol, gdje:
Z se izabire između -NR8C(O)- i -NR9-;
R1 se izabire između H, R6, C1-6 alkila supstituiranog s 0-3 R6, C2-6 alkenila supstituiranog s 0-3 R6, C2-6 alkinila supstituiranog s 0-3 R6, C6-10 arilne skupine supstituirane s 0-5 R6, i 5-10-eročlanog heteroarilnog sustava koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiranog s 0-3 R6;
R2 se izabire između C6-10 arilne skupine supstituirane s 0-5 R7 i 5-10-eročlanog heteroarilnog sustava koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiranog s 0-3 R7;
R5 je -NR5aR5a;
R5a, pri svakom pojavljivanju, se nezavisno izabire između H, metil, C1-6 alkila supstituiranog s 0-2 R5e gdje se alkil izabire između etil, propil, i-propil, butil, i-butil, pentil, heksil; alila supstituiranog s 0-1 R5e; propinila supstituiranog s 0-1 R5e; i (CH2)r-C3-4 karbocikličkog ostatka supstituiranog s 0-5 R5e, gdje se karbociklički ostatak izabire između ciklopropil, i ciklobutil;
R5e, pri svakom pojavljivanju, se izabire između C1-6 alkil, C2-8 alkenil, C2-8 alkinil, C3-6 cikloalkil, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rOC1-5 alkil, OH, SH, (CH2)rSC1-5 alkil, (CH2)rNR5fR5f, i (CH2)rfenil;
R5f, pri svakom pojavljivanju, se izabire između H, C1-6 alkil, i C3-6 cikloalkil;
R6, pri svakom pojavljivanju, se izabire između C1-8 alkil, (CH2)rC3-6 cikloalkil, Cl, Br, I, F, NO2, CN, (CR’R’)rNR6aR6a, (CR’R’)rOH, (CR’R’)rO (CR’R’)rR6d, (CR’R’)rSH, (CR’R’)rC (O)H, (CR’R’)rS (CR’R’)rR6d, (CR’R’)rSC (O) (CR’R’)rR6b, (CR’R’)rC (O)OH, (CR’R’)rC (O) (CR’R’)rR6b, (CR’R’)rC (O) NR6aR6a, (CR’R’)rNR6fC (O) (CR’R’)rR6b, (CR’R’)rC (O) O (CR’R’)rR6d, (CR’R’)rOC (O) (CR’R’)rR6b, (CR’R’)rOC (O) NR6a (CR’R’)rR6d, (CR’R’)rNR6aC (O) NR6a (CR’R’)rR6d, (CR’R’)rNR6aC (S) NR6a (CR’R’)rR6d, (CR’R’)rNR6fC (O) O (CR’R’)rR6b, (CR’R’)rC (=NR6f) NR6aR6a, (CR’R’)rNHC (=NR6f) NR6fR6f, -(CR’R’)rS (O)p (CR’R’)rR6b, (CR’R’)rS (O)2NR6aR6a, (CR’R’)rNR6fS (O)2NR6aR6a, (CR’R’)rNR6fS (O)2 (CR’R’)rR6b, C1-6 haloalkil, C2-8 alkenil supstituiran s 0-3 R’, C2-8 alkinil supstituiran s 0-3 R’, (CR’R’)rfenil supstituiran s 0-3 R6e, i (CH2)r-5-6-eročlani heterociklički sustav koji sadrži 1-2 heteroatoma izabrana između N, O, i S, supstituiran s 0-2 R6e;
alternativno, dva R6 na susjednim atomima na R1 mogu se spojiti da formiraju ciklički acetal;
R6a, pri svakom pojavljivanju, se izabire između H, metila supstituiranog s 0-1 R6g, C2-6 alkila supstituiranog s 0-2 R6e, C3-8 alkenila supstituiranog s 0-2 R6e, i C3-8 alkinila supstituiranog s 0-2 R6e;
R6b, pri svakom pojavljivanju, se izabire između H, C1-6 alkila supstituiranog s 0-2 R6e, C3-8 alkenila supstituiranog s 0-2 R6e, i C3-8 alkinila supstituiranog s 0-2 R6e;
R6d, pri svakom pojavljivanju, se izabire između C3-8 alkenila supstituiranog s 0-2 R6e, C3-8 alkinila supstituiranog s 0-2 R6e, metil, CF3, C2-6 alkil supstituiran s 0-3 R6e, i C2-4 haloalkil;
R6e, pri svakom pojavljivanju, se izabire između C1-6 alkil, C2-8 alkenil, C2-8 alkinil, (CH2)rC3-6 cikloalkil, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rOC1-5 alkil, OH, SH, (CH2)rSC1-5 alkil, (CH2)rNR6fR6f, i (CH2)rfenil;
R6f, pri svakom pojavljivanju, se izabire između H, C1-5 alkil, i C3-6 cikloalkil, i fenil;
R6g se nezavisno izabire između- C (O) R6b, -C (O) OR6d, -C (O) NR6fR6f, i (CH2)rfenil;
R7, pri svakom pojavljivanju, se izabire između C1-8 alkil, (CH2)rC3-6 cikloalkil, Cl, Br, I, F, NO2, CN, (CR’R’)rNR7aR7a, (CR’R’)rOH, (CR’R’)rO (CR’R’)rR7d, (CR’R’)rSH, (CR’R’)rC (O) H, (CR’R’)rS (CR’R’)rR7d, (CR’R’)rC (O) OH, (CR’R’)rC (O) (CR’R’)rR7b, (CR’R’)rC (O) NR7aR7a, (CR’R’)rNR7fC (O) (CR’R’)rR7b, (CR’R’)rC (O) O (CR’R’)rR7d, (CR’R’)rOC (O) (CRR’)rR7b, (CR’R’)rOC (O) NR7a (CR’R’)rR7a, (CR’R’)rNR7aC (O) NR7a (CR’R’)rR7a, (CR’R’)rNR7fC (O) O (CR’R’)rR7d, (CR’R’)rC (=NR7f) NR7aR7a, (CR’R’)rNHC (=NR7f) NR7fR7f, (CR’R’)rS (O)p (CR’R’)rR7b, (CR’R’)rS (O)2NR7aR7a, (CR’R’)rNR7aS (O)2NR7aR7a, (CR’R’)rNR7fS (O)2 (CR’R’)rR7b, C1-6 haloalkil, C2-8 alkenil supstituiran s 0-3 R’, C2-8 alkinil supstituiran s 0-3 R’, i (CR’R’)rfenil supstituiran s 0-3 R7e;
alternativno, dva R7 na susjednim atomima na R2 mogu se spojiti da formiraju ciklički acetal;
R7a, pri svakom pojavljivanju, se nezavisno izabire između H, metila supstituiranog s 0-1 R7g, C2-6 alkila supstituiranog s 0-2 R7e, C3-8 alkenila supstituiranog s 0-2 R7e, C3-8 alkinila supstituiranog s 0-2 R7e, (CH2)r-C3-10 karbocikličkog ostatka supstituiranog s 0-5 R7e, i (CH2)r-5-10-eročlanog heterocikličkog sustava koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiranog s 0-2 R7e;
R7b, pri svakom pojavljivanju, se izabire između C1-6 alkila supstituiranog s 0-2 R7e, C3-8 alkenila supstituiranog s 0-2 R7e, C3-8 alkinila supstituiranog s 0-2 R7e, (CH2)rC3-6 karbocikličkog ostatka supstituiranog s 0-3 R7e, i (CH2)r-5-6-eročlanog heterocikličkog sustava koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiranog s 0-2 R7e;
R7d, pri svakom pojavljivanju, se izabire između C3-8 alkenila supstituiranog s 0-2 R7e, C3-8 alkinila supstituiranog s 0-2 R7e, metil, CF3, C2-4 haloalkil, C2-6 alkil supstituiran s 0-3 R7e, (CH2)r-C3-10 karbociklički ostatak supstituiran s 0-3 R7e, i (CH2)r-5-6-eročlani heterociklički sustav koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiran s 0-3 R7e;
R7e, pri svakom pojavljivanju, se izabire između C1-6 alkil, C2-8 alkenil, C2-8 alkinil, (CH2)rC3-6 cikloalkil, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rOC1-5 alkil, OH, SH, C (O) OC1-5 alkil, (CH2)rSC1-5 alkil, (CH2)rNR7fR7f, i (CH2)rfenil;
R7f, pri svakom pojavljivanju, se izabire između H, C1-5 alkil, i C3-6 cikloalkil, i fenil;
R7g se nezavisno izabire između- C (O) R7b, -C (O) OR7d, -C (O) NR7fR7f, i (CH2)rfenil;
R’, pri svakom pojavljivanju, se izabire između H, C1-6 alkila supstituiranog s R6e, C2-8 alkenil, C2-8 alkinil, (CH2)rC3-6 cikloalkil;
R8 se izabire između H, C1-4 alkil, i C3-4 cikloalkil;
R9 se izabire između H, C1-4 alkil, C3-4 cikloalkil, -C (O) H, i - C (O)- C1-4alkil;
p, pri svakom pojavljivanju, se nezavisno izabire između 0, 1, i 2; i
r, pri svakom pojavljivanju, se nezavisno izabire između 0, 1, 2, 3, i 4.
2. Spoj prema zahtjevu 1, gdje:
R5a, pri svakom pojavljivanju, se nezavisno izabire između H, metil, etil, propil, i-propil, butil, i-butil, pentil, heksil, ciklopropil, i ciklobutil; i
r, pri svakom pojavljivanju, se izabire između 0, 1, i 2.
3. Spoj prema zahtjevu 2, gdje:
R1 se izabire između H, R6, C1-6 alkila supstituiranog s 0-3 R6, C2-6 alkenila supstituiranog s 0-3 R6, C2-6 alkinila supstituiranog s 0-3 R6, C6-10 arilne skupine supstituirane s 0-5 R6, gdje se arilna skupina izabire između fenil i naftil, i 5-10-eročlani heteroarilni sustav koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiran s 0-3 R6, gdje se heteroaril izabire između indolil, benzimidazolil, benzofuranil, benzotiofuranil, benzoksazolil, benztiazolil, benztriazolil, benztetrazolil, benzizoksazolil, benzizotiazolil, benzimidazalonil, cinolinil, furanil, imidazolil, indazolil, indolil, izonikotinil, izokinolinil izotiazolil, izoksazolinil, izoksazolil, oksazolil, ftalazinil, pikolinil, pirazinil, pirazolil, piridazinil, piridil, piridinil, pirimidinil, pirolil, kinazolinil, kinolinil, tiazolil, tienil, triazinil, i tetrazolil;
R2 se izabire između fenila supstituiranog s 0-2 R7, i 5-10-eročlanog heteroarilnog sustava koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiranog s 0-3 R7 gdje se heteroaril izabire između indolil, benzimidazolil, benzofuranil, benzotiofuranil, benzoksazolil, benztiazolil, benztriazolil, benztetrazolil, benzizoksazolil, benzizotiazolil, benzimidazalonil, cinolinil, furanil, imidazolil, indazolil, indolil, izokinolinil izotiazolil, izoksazolil, oksazolil, ftalazinil, pirazinil, pirazolil, piridazinil, piridil, piridinil, pirimidinil, pirolil, pirolotriazinil, kinazolinil, kinolinil, tiazolil, tienil, i tetrazolil; i
R8 se izabire između H, metil, etil, propil, i-propil, i ciklopropil.
4. Spoj prema zahtjevu 2 ili 3, gdje:
R6, pri svakom pojavljivanju, se izabire između C1-8 alkil, C2-8 alkenil, C2-8 alkinil, (CH2)rC3-6 cikloalkil, Cl, Br, I, F, NO2, CN, (CH2)rNR6a’R6a’, (CH2)rOH, (CH2)rO (CH2)rR6d, (CH2)rSH, (CH2)rC (O) H, (CH2)rS (CH2)rR6d, (CH2)rC(O) OH, (CH2)rC (O) (CH2)rR6b, (CH2)rC (O) NR6aR6a, (CH2)rNR6fC (O) R6b’, (CH2)rC (O) O (CH2)rR6d, (CH2)rNR6aC (O) NR6a’R6d’, (CH2)rNR6aC (S) NR6aR6a, (CH2)rOC (O) (CH2)rR6b, (CH2)rS (O)pR6b’, (CH2)rS(O)2NR6aR6a, (CH2)rNR6fS (O)2 (CH2)rR6b, (CH2)rNR6fS (O)2 NR6aR6a, C1-6 haloalkil, i (CH2)rfenil supstituiran s 0-3 R6e, i (CH2)r- 5-6-eročlani heterociklički sustav koji sadrži 1- 2 heteroatoma izabrana između N, O, i S, supstituiran s 0-2 R6e, gdje se heterociklički sustav izabire između aziridinil, azetidinil, pirolil, piperidinil, i morfolinil;
R6a, pri svakom pojavljivanju, se nezavisno izabire između H, metil, etil, propil, i-propil, butil, i-butil, t-butil, pentil, i heksil;
R6b, pri svakom pojavljivanju, se izabire između H, metil, etil, propil, i-propil, butil, i-butil, t-butil, pentil, i heksil;
R6d, pri svakom pojavljivanju, se izabire između metil, CF3, etil, propil, i-propil, butil, i-butil, t-butil, pentil, i heksil;
R6e, pri svakom pojavljivanju, se izabire između C1-6 alkil, C2-8 alkenil, C2-8 alkinil, (CH2)rC3-6 cikloalkil, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rOC1-5 alkil, OH, SH, (CH2)rSC1-5 alkil, (CH2)rNR6fR6f, C (O) NHR6h, C (O) OC1-5 alkil, (CH2)rOH, C (O) OH, (CH2)rC (O) NHSO2- R6h, NHSO2R6h, (CH2)rtetrazolil, i (CH2)rfenil i (CH2)r-5-6-eročlani heterociklički sustav koji sadrži 1- 4 heteroatoma izabrana između N, O, i S;
R6f, pri svakom pojavljivanju, se izabire između H, metil, etil, propil, i-propil, butil, i-butil, t-butil, pentil, heksil, ciklopropil, i fenil;
R7 se izabire između metil, etil, propil, i-propil, butil, i-butil, s-butil, t-butil, pentil, heksil, (CH2)rC3-6 cikloalkil, Cl, Br, I, F, NO2, CN, (CH2)rNR7aR7a, (CH2)rOH, (CH2)rO (CH2)rR7d, (CH2)rSH, (CH2)rC (O) H, (CH2)rS (CH2)rR7d, (CH2)rC (O) OH, (CH2)rC (O) (CH2)rR7b, (CH2)rC (O) NR7aR7a, (CH2)rNR7fC (O) (CH2)rR7b, (CH2)rC (O) O (CH2)rR7d, (CH2)rOC (O) (CH2)rR7b, (CH2)rOC (O) NR7aR7a, (CH2)rNR7aC (O) NR7aR7a, (CH2)rNR7aC (O) O (CH2)rR7d, (CH2)rS (O)p (CH2)rR7b, (CH2)rS (O)2NR7aR7a, (CH2)rNR7fS (O)2 (CH2)rR7b, C1-6 haloalkil, i (CH2)rfenil supstituiran s 0-3 R7e i (CH2)r-5-6-eročlani heterociklički sustav koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiran s 0-3 R7e, gdje se heterociklički sustav izabire između tienil, piridinil, benzotiazolil, i tetrazolil;
R7a, pri svakom pojavljivanju, se izabire između H, metil, etil, propil, i-propil, butil, i-butil, t- butil, pentil, heksil, prop-2-enil, 2-metil-2-propenil, ciklopropil, ciklobutil, ciklopentil, cikloheksil, CH2ciklopropil, i benzil;
R7b, pri svakom pojavljivanju, se izabire između metil, etil, propil, i-propil, butil, i-butil, t-butil, pentil, heksil, ciklopropil, ciklopentil, CH2-ciklopentil, cikloheksil, CH2- cikloheksil, CF3, pirolidinil, morfolinil, piperizenil supstituiran s 0-1 R7e, i azetidinil;
R7d, pri svakom pojavljivanju, se izabire između metil, CF3, CF2CF3, CHF2, CH2F, etil, propil, i-propil, butil, ibutil, t-butil, pentil, heksil, i ciklopropil;
R7e, pri svakom pojavljivanju, se izabire između C1-6 alkil, C2-8 alkenil, C2-8 alkinil, (CH2)rC3-6 cikloalkil, Cl, F, Br, I, CN, NO2, (CF2)rCF3, (CH2)rOC1-5 alkil, (CH2)rOH, OH, SH, C (O) OH, C (O) NHR7h, C (O) OC1-5 alkil, (CH2)rSC1-5 alkil, (CH2)rNR7fR7f, (CH2)rC (O) NHSO2- R7h, NHSO2R7h, i (CH2)rfenil, (CH2)rtetrazolil;
R7f, pri svakom pojavljivanju, se izabire između H, metil, etil, propil, i-propil, butil, i-butil, t-butil, pentil, heksil, ciklopropil, i fenil; i
r je 0 ili 1.
5. Spoj prema zahtjevima 1-4, gdje:
R7, pri svakom pojavljivanju, se izabire između metil, etil, propil, i- propil, butil, i- butil, s- butil, t- butil, pentil, heksil, (CH2)rC3-6 cikloalkil, Cl, Br, I, F, NO2, CN, (CH2)rNR7aR7a, (CH2)rOH, (CH2)rOR7d, (CH2)rSH, (CH2)rC(O) H, (CH2)rSR7d, (CH2)rC (O) OH, (CH2)rC (O) R7b, (CH2)rC (O) NR7aR7a, (CH2)rNR7fC (O) R7b, (CH2)rC (O)OR7d, (CH2)rOC (O) R7b, (CH2)rOC (O) NR7aR7a, (CH2)rNR7aC (O) NR7aR7a, (CH2)rNR7fC (O) OR7d, (CH2)rS(O)pR7b, (CH2)rS (O)2NR7aR7a, (CH2)rNR7aS (O)2NR7aR7a, (CH2)rNR7fS (O)2R7b, C1-2 haloalkil, (CH2)rfenil supstituiran s 0-3 R7e, i (CH2)r-5-6-eročlani heterociklički sustav koji sadrži 1- 4 heteroatoma izabrana između N, O, i S, supstituiran s 0-3 R7e, gdje se heterociklički prsten izabire između tiofenil, piridinil, benzotiazolil, i tetrazolil.
6. Spoj prema zahtjevima 1-4, gdje
Z se izabire između -NHC(O)-, i -NH-;
R1 se izabire između C1-6 alkila supstituiranog od 0-1 R6, i - C (O) O- C1-6 alkil; i
R2 se izabire između fenila supstituiranog s 0-2 R7, i 5-10-eročlani heteroarilni sustav koji sadrži 1-4 heteroatoma izabrana između N, O, i S, supstituiran s 0-3 R7 gdje se heteroarilni sustav izabire između kinazolinil, triazinil, pirimidinil, pikolinil, izonikotinil, furanil, indolil, piridinil, pirazolil, pirazinil, tiazolil, tiofenil, i izoksazolil.
7. Spoj prema zahtjevima 1- 4, gdje
R1 se izabire između H, C1-6 alkila supstituiranog s 0-1 R6, i - C (O) O- C1-6 alkil.
8. Spoj prema zahtjevu 1 koji ima strukturu:
[image]
ili njegova farmaceutski prihvatljiva sol.
9. Spoj prema zahtjevu 1 koji ima strukturu:
[image]
ili njegova farmaceutski prihvatljiva sol.
10. Spoj prema zahtjevu 1 koji ima strukturu:
[image]
ili njegova farmaceutski prihvatljiva sol.
11. Spoj prema zahtjevu 1 koji ima strukturu
Cis-(3S)-1-(4-(tert- butilamino)cikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2-on,
trans-(3S)-1-(4-(tert- butilamino)cikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on,
Cis-(3S)-1-(4-(tert- butilamino)cikloheksil)-3-(6-tert-butilpirolo[1,2-f][1,2,4] triazin-4- ilamino) pirolidin-2- on,
trans-(3S)-1-(4-(tert- butilamino)cikloheksil)-3-(6- tert- butilpirolo [1,2-f][1,2,4] triazin-4- ilamino) pirolidin-2- on,
cis-(3S)-3- tert- butil- N-(1-(4-(tert- butilamino) cikloheksil)-2- oksopirolidin-3- il)-4- hidroksibenzamid,
trans-(3S)-3- tert- butil- N-(1-(4-(tert- butilamino) cikloheksil)-2- oksopirolidin-3- il)-4- hidroksibenzamid,
Cis- i trans-(3S)-4- tert- butil- N-(1-(4-(tert- butilamino) cikloheksil)-2- oksopirolidin-3- il)- 1H- pirol-2-karboksamid,
Cis- i trans-(3S)-4- tert- butil- N-(1-(4-(tert- butilamino) cikloheksil)-2- oksopirolidin-3- il)-1- metil- 1Hpirol-2- karboksamid,
N- {(3S)-1-[(1S, 2R, 4R)-4-(Izopropil- metil- amino)-2- propil- cikloheksil]-2- okso- pirolidin-3- il}-2-(3-izopropil- ureido)- 5- trifluorometil- benzamid,
1- {2-[((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il) karbamoil]-4-(trifluorometil) fenil}-3- etilurea,
1-(2-(((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il) karbamoil)-4-(trifluorometil) fenil)-3- ciklopropilurea,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil)benzamid,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)benzamid,
2- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)pirimidin-4- karboksamid,
3- tert- butil-4- hidroksi- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il) benzamid,
6- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)pikolinamid,
2- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)izonikotinamid,
(S)-1-[(1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil]-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-3-(6-(trifluorometoksi) kinazolin-4-ilamino) pirolidin-2- on,
(S)-3-(6- klorokinazolin-4- ilamino)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)pirolidin-2- on,
(S)-3-(6- fluorokinazolin-4- ilamino)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil) pirolidin-2- on,
(S)-3-(6- tert- butilpirimido [5, 4- d] pirimidin-4- ilamino)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-propilcikloheksil) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-3-(6-(2- metoksifenil) kinazolin-4-ilamino) pirolidin-2- on,
3-(4-((S)-1-((lS, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- ilamino) kinazolin-6- il) benzonitril,
(S)-3-(6- klorokinazolin-4- ilamino)-1-((1S, 2R, 4R)-4-(izopropilamino)-2- propilcikloheksil) pirolidin-2- on,
(S)-3-(6- klorokinazolin-4- ilamino)-1-((1S, 2R, 4S)-4-(etil (izopropil) amino)-2- propilcikloheksil) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(tert- butilamino)-2- propilcikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino)pirolidin-2- on,
(S)-1-((1S, 2R, 4S)-4-(tert- butilamino)-2- propilcikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino)pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino)pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-3-(6-(trifluorometoksi) kinazolin-4- ilamino)pirolidin-2- on,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-4- hidroksibenzamid,
N-((S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
N-((S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-2-(trifluorometil) pirimidin-4- karboksamid,
(S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-3-(6-(2- metoksifenil) kinazolin-4- ilamino)pirolidin-2- on,
6- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-2- oksopirolidin-3- il) pikolinamid,
5-(4- klorofenil)- N-((S)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)-2- oksopirolidin-3- il) furan-2- karboksamid,
(S)-3-(6- tert- butilpirimido [5, 4- d] pirimidin-4- ilamino)-1-((1S, 2R, 4R)-4-(dimetilamino)-2- propilcikloheksil)pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(dietilamino)-2- propilcikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(dietilamino)-2- propilcikloheksil)-3-(6-(trifluorometoksi) kinazolin-4- ilamino)pirolidin-2- on,
N-((S)-1-((1S, 2R, 4R)-4-(dietilamino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
2- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(dietilamino)-2- propilcikloheksil)-2- oksopirolidin-3- il) pirimidin-4-karboksamid,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-3-(6-(trifluorometil) kinolin-4- ilamino)pirolidin-2- on,
(R)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-3-(6-(trifluorometil) kinolin-4- ilamino)pirolidin-2- on,
4- hidroksi- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-3-fenil- benzamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-3- fenilbenzamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-2- fenilizonikotinamid N- oksid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-1- metil- 1Hindol-3- karboksamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-1- metil- 1Hindol-2- karboksamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-2-(metilsulfonamido)-5-(trifluorometil) benzamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)- 5-(trifluorometil)-2-(trifluorometilsulfonamido) benzamid,
5- izopropil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)-2-(trifluorometilsulfonamido) benzamid,
2- kloro- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il)- 5-(trifluorometil) benzamid,
metil 3-(((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il) karbamoil)-5- tert- butilbenzoat,
3-(((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il) karbamoil)- 5-tert- butilbenzojeva kiselina,
2- tert- butil-1- okso- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- propilcikloheksil)-2- oksopirolidin-3- il) pirimidin-4- karboksamid,
(S)-1-((1S, 2S, 4R)-2- izopropil-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on,
(S)-1-((1S, 2S, 4S)-2- izopropil-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on,
(S)-1-((1S, 2S, 4R)-2- izopropil-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometoksi) kinazolin-4- ilamino) pirolidin-2- on,
(S)-3-(6- klorokinazolin-4- ilamino)-1-((1S, 2S, 4R)-2- izopropil-4-(izopropil (metil) amino) cikloheksil)pirolidin-2- on,
6- tert- butil- N-((S)-1-((1S, 2S, 4R)-2- izopropil-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3-il) pikolinamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- metilcikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil)benzamid,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- metilcikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- metilcikloheksil)-3-(6-(trifluorometoksi) kinazolin-4-ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-2- etil-4-(izopropil (metil) amino)- cikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metoksimetil) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
1-(2-(((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metoksimetil) cikloheksil)-2- oksopirolidin-3- il)karbamoil)-4-(trifluorometil) fenil)-3- etilurea,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metoksimetil) cikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
(S)-3-(6- klorokinazolin-4- ilamino)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metoksimetil) cikloheksil)pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metoksimetil) cikloheksil)-3-(6-(trifluorometoksi) kinazolin-4- ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metoksimetil) cikloheksil)-3-(6-(2- metoksifenil)kinazolin-4- ilamino) pirolidin-2- on,
N-((S)-1-((1S, 2R, 4R)-2-(etoksimetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
(S)-1-((1S, 2R, 4R)-2-(etoksimetil)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
1-(2-(((S)-1-((1S, 2R, 4R)-2-(etoksimetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)karbamoil)-4-(trifluorometil) fenil)-3- etilurea,
N-((S)-1-((1S, 2S, 4R)-4-(izopropil (metil) amino)-2-(2- metoksietil) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
(S)-1-((1S, 2S, 4R)-4-(izopropil (metil) amino)-2-(2- metoksietil) cikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
1-(2-(((S)-1-((1S, 2S, 4R)-4-(izopropil (metil) amino)-2-(2- metoksietil) cikloheksil)-2- oksopirolidin-3- il)karbamoil)-4-(trifluorometil) fenil)-3- etilurea,
1-((1S, 2R, 4R)-2-(1- hidroksipropil)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
1-((1S, 2R, 4R)-2-(1- hidroksipropil)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
N-(1-((1S, 2R, 4R)-2-(1- hidroksipropil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
N-(1-((1S, 2R, 4R)-2-(1- hidroksipropil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-2-(tertbutil)pirimidin-4- karboksamid,
5-(4- klorofenil)- N-(1-((1S, 2R, 4R)-2-(1- hidroksipropil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il) furan-2- karboksamid,
1-((1S, 2R, 4R)-2-(1- hidroksietil)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
N-(1-((1S, 2R, 4R)-2-(1-hidroksietil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
1-((1S, 2R, 4R)-2-(hidroksimetil)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-2- on,
1-((1S, 2R, 4R)-2-(2- hidroksipropan-2- il)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil)kinazolin-4- ilamino) pirolidin-2- on,
N-((S)-1-((1S, 2R, 4R)-2-(2- hidroksipropan-2- il)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
6- tert- butil- N-((S)-1-((1S, 2R, 4R)-2-(2- hidroksipropan-2- il)-4-(izopropil (metil) amino) cikloheksil)-2-oksopirolidin-3- il) pikolinamid,
((1R, 2S, 5R)- 5-(izopropil (metil) amino)-2-(2- okso-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-1- il) cikloheksil) metil izobutirat,
((1R, 2S, 5R)- 5-(izopropil (metil) amino)-2-(2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1- il) cikloheksil)metil izobutirat,
((1R, 2S, 5R)-2-(3-(3- tert- butil-1- metil- 1H- pirazol- 5- karboksamido)-2- oksopirolidin-1- il)- 5-(izopropil(metil) amino) cikloheksil) metil izobutirat,
((1R, 2S, 5R)- 5-(dimetilamino)-2-(2- okso-3-(6-(trifluorometil) kinazolin-4- karboksamido) pirolidin-1- il)cikloheksil) metil izobutirat,
((1R, 2S, 5R)- 5-(dimetilamino)-2-(2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1- il) cikloheksil) metil izobutirat,
((1R, 2S, 5R)-2-(3-(3- tert- butil-1- metil- 1H- pirazol- 5- karboksamido)-2- oksopirolidin-1- il)- 5-(dimetilamino)cikloheksil) metil izobutirat,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3-il)-3-(trifluorometil) benzamid,
2- amino- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3- il)- 5-(trifluorometoksi) benzamid,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il)-1- metil- 1H- pirazol- 5- karboksamid,
6- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il) pikolinamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3-il)- 6-(trifluorometil) pikolinamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3-il)- 6- fenilpikolinamid,
N-((S)-1-((1S, 2R, 4R)-4-(etil (izopropil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
N-((S)-1-((1S, 2R, 4R)-2-(metilsulfonilmetil)-4-(neopentilamino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3-il)-4- metil-3-(trifluorometil) benzamid,
4- kloro- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il) benzamid,
3- fenil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3- il) benzamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3-il)- 6- fenilpirazin-2- karboksamid,
3- fluoro- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3- il)- 5-(trifluorometil) benzamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3-il)-3-(trifluorometoksi) benzamid,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-3-(6-(trifluorometil)kinazolin-4- ilamino) pirolidin-2- on,
(S)-3-(6- klorokinazolin-4- ilamino)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil)cikloheksil) pirolidin-2- on,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2- oksopirolidin-3-il)- 3, 5- bis (trifluorometil) benzamid,
3, 5- dikloro- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(metilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il) benzamid,
N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-4- fluoro-3-(trifluorometil) benzamid,
N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)- 6-(trifluorometil) pikolinamid,
N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
6- tert- butil- N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2-oksopirolidin-3- il) pikolinamid,
N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometoksi) benzamid,
N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3- fluoro- 5-(trifluorometil) benzamid,
2- amino- N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2-oksopirolidin-3- il)- 5-(trifluorometoksi) benzamid,
3- amino- N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2-oksopirolidin-3- il)- 5-(trifluorometil) benzamid,
N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)- 5- fenilnikotinamid N- oksid,
(S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil)kinazolin-4- ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-3-(6- klorokinazolin-4- ilamino) pirolidin-2- on,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2-oksopirolidin-3- il)-4- hidroksibenzamid,
N-((S)-1-((1S, 2R, 4R)-2-(tert- butilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)- 5- fenilnikotinamid,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-3-(6-(trifluorometil)kinazolin-4- ilamino) pirolidin-2- on,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il)-1- metil- 1H- pirazol- 5- karboksamid,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il) benzamid,
(S)-1-((1S, 2R, 4R)-4-(etil (izopropil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-3-(6-(trifluorometil)kinazolin-4- ilamino) pirolidin-2- on,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(etil (izopropil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il) benzamid,
3- tert- butil- N-((S)-1-((1S, 2R, 4R)-4-(izopropil (propil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-2-oksopirolidin-3- il) benzamid,
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-3-(6-(trifluorometoksi)kinazolin-4- ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(etil (izopropil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-3-(6-(trifluorometoksi)kinazolin-4- ilamino) pirolidin-2- on,
(S)-1-((1S, 2R, 4R)-4-(etil (izopropil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-3-(6-(trifluorometil)kinazolin-4- ilamino) pirolidin-2- on,
N-((S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2-(izopropilsulfonilmetil) cikloheksil)-2- oksopirolidin-3- il)-1- metil- 1H- indol-2- karboksamid,
N-((S)-1-((1S, 2R, 4R)-2-(etilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(trifluorometil) benzamid,
(S)-1-((1S, 2R, 4R)-2-(etilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-3-(6-(trifluorometil)kinazolin-4- ilamino) pirolidin-2- on,
N-((S)-1-((1S, 2R, 4R)-2-(etilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)-3-(fenil) benzamid,
3-(((S)-1-((1S, 2R, 4R)-2-(etilsulfonilmetil)-4-(izopropil (metil) amino) cikloheksil)-2- oksopirolidin-3- il)karbamoil)- 5- tert- butilbenzojeva kiselina,
(1R, 2S, 5R)- metil 5-(izopropil (metil) amino)-2-((S)-2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butil (metil) amino)-2-((S)-2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(izopropil (metil) amino)-2-((S)-2- okso-3-(6-(trifluorometil) kinazolin-4- ilamino)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(izopropil (metil) amino)-2-((S)-2- okso-3-(6-(trifluorometoksi) kinazolin-4- ilamino)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 2-((S)-3-(3- tert- butil-4- hidroksibenzamido)-2- oksopirolidin-1- il)- 5-(izopropil (metil)amino)- cikloheksankarboksilat,
(1R, 2S, 5R)- metil 2-((S)-3-(3- fluoro- 5-(trifluorometil) benzamido)-2- oksopirolidin-1- il)- 5-(izopropil(metil) amino)- cikloheksankarboksilat,
(1R, 2S, 5R)- metil 2-((S)-3-(2- tert- butilpikolinamido)-2- oksopirolidin-1- il)- 5-(izopropil (metil) amino)-cikloheksankarboksilat,
(1R, 2S, 5R)- metil 2-((S)-3-(3- tert- butil-4- hidroksibenzamido)-2- oksopirolidin-1- il)- 5-(tert- butilamino)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 2-((S)-3-(3- tert- butilbenzamido)-2- oksopirolidin-1- il)- 5-(tert- butilamino) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2- tert- butilpirimidin-4- karboksamido)-2- oksopirolidin-1-il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2- tert- butilpikolinamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(3- fenilbenzamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(2- fenilpirazin- 6- karboksamido) pirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(4- fluoro-3-(trifluorometil)- benzamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butil (metil) amino)-2-((S)-3-(2-(4- klorofenil) furan- 5- karboksamido)-2-oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butil (metil) amino)-2-((S)-2- okso-3-(6-(trifluorometoksi) kinazolin-4- ilamino)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butil (metil) amino)-2-((S)-2- okso-3-(6-(trifluorometil) kinazolin-4- ilamino)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(4-(perfluoroetil) tiazol-2- karboksamido) pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(4- tert- butiltiazol-2- karboksamido)-2- oksopirolidin-1-il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(4-(3-(trifluorometil)- fenil) tiazol-2- karboksamido)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(4- feniltiazol-2- karboksamido) pirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(4-(4- klorofenil) tiazol-2- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(2- feniltiazol-4- karboksamido) pirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(4- klorofenil) tiazol-4- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 2-((S)-3-(2- tert- butil- 5- metilfuran-4- karboksamido)-2- oksopirolidin-1- il)- 5-(tertbutilamino)cikloheksan- karboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(2-(trifluorometil) furan- 5- karboksamido) pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(4- klorofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(2-(3-(trifluorometil) fenil) furan- 5- karboksamido)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(2- kloro- 5-(trifluorometil) fenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(2, 5- diklorofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(4- izopropilfenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(4- fluorofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(2- fenilfuran- 5- karboksamido) pirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(3- fluorofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(3- cijanofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(3- metoksifenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(4- cijanofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(3, 4- difluorofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(2-(4-(trifluorometil) fenil) furan- 5- karboksamido)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(3-(4- metoksifenil) furan- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(3-(4-(trifluorometil) fenil) furan- 5- karboksamido)pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(3- fenilfuran- 5- karboksamido) pirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(3- feniltiofen- 5- karboksamido) pirolidin-1-il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(2- feniltiofen- 5- karboksamido) pirolidin-1-il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(2-(4- metoksifenil) tiofen- 5- karboksamido)-2- oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(1- metil-3- fenil- 1H- pirazol- 5- karboksamido)-2-oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(3- fenilizoksazol- 5- karboksamido) pirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(6-(trifluorometil) kinazolin-4- ilamino) pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(6- tert- butilpirimido [5, 4- d] pirimidin-4- ilamino)-2-oksopirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-3-(6- klorokinazolin-4- ilamino)-2- oksopirolidin-1- il)cikloheksankarboksilat,
(1R, 2S, 5R)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(6-(trifluorometoksi)- kinazolin-4- ilamino) pirolidin-1- il) cikloheksankarboksilat,
(1R, 2S, 5S)- metil 5-(tert- butilamino)-2-((S)-2- okso-3-(3-(trifluorometil)- benzamido) pirolidin-1- il)cikloheksankarboksilat,
(1S, 2S, 5R)- metil 5-(izopropil (metil) amino)-2-((S)-2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1-il) cikloheksankarboksilat,
(1S, 2S, 5R)- metil 2-((S)-3-(2-(4- klorofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il)- 5-(izopropil(metil) amino) cikloheksankarboksilat,
(1S, 2S, 5R)- metil 2-((S)-3-(3- tert- butil-4- hidroksibenzamido)-2- oksopirolidin-1- il)- 5-(izopropil (metil)amino) cikloheksankarboksilat,
(1S, 2S, 5R)- etil 2-((S)-3-(2-(4- klorofenil) furan- 5- karboksamido)-2- oksopirolidin-1- il)- 5-(izopropil(metil) amino) cikloheksankarboksilat,
etil 3-((1S, 2S, 5R)- 5-(izopropil (metil) amino)-2-((S)-2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1- il) cikloheksil) propanoat,
3-((1S, 2S, 5R)- 5-(izopropil (metil) amino)-2-((S)-2- okso-3-(3-(trifluorometil) benzamido) pirolidin-1- il)cikloheksil) propan kiselina,
(S)-1-((1R, 2S, 4S)-4-(izopropil (metil) amino)-2- metoksicikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on, ili
(S)-1-((1S, 2R, 4R)-4-(izopropil (metil) amino)-2- metoksicikloheksil)-3-(6-(trifluorometil) kinazolin-4-ilamino) pirolidin-2- on.
12. Spoj prema bilo kojem od zahtjeva 1-11, za uporabu u liječenju.
13. Farmaceutska smjesa, sadrži farmaceutski prihvatljivi nosač i terapijski učinkovitu količinu spoja prema zahtjevima 1-11.
14. Spoj prema bilo kojem od zahtjeva 1-11 za uporabu u liječenju poremećaja izabranog između osteoartritisa, aneurizme, vrućice, kardiovaskularnih učinaka, Crohnove bolesti, kongestivnog zatajenja srca, autoimunih bolesti, HIV-infekcije, HIV-povezane demencije, psorijaze, idiopatske plućne fibroze, transplantacijske arterioskleroze, fizički ili kemijski inducirane traume mozga, upalne bolesti crijeva, alveolitisa, kolitisa, sistemskog lupus eritematosus, nefrotoksičnog serumskog nefritisa, glomerulonefritisa, astme, multiple skleroze, ateroskleroze, reumatoidnog artritisa, restenoze, transplantacije organa i raka.
15. Uporaba spoja prema bilo kojem od zahtjeva 1 do 11 u pripremi lijeka za modulaciju aktivnosti receptora kemokina u bolesnika kojemu je to potrebno.
16. Uporaba spoja prema bilo kojem od zahtjeva 1 do 11 u pripremi lijeka za modulaciju MCP-1, MCP-2, MCP-3, MCP-4, i MCP-5 aktivnosti u bolesnika kojemu je to potrebno.
17. Uporaba spoja prema bilo kojem od zahtjeva 1 do 11 u pripremi lijeka za modulaciju MCP-1 aktivnosti u bolesnika kojemu je to potrebno.
18. Uporaba spoja prema bilo kojem od zahtjeva 1 do 11 u pripremi lijeka za modulaciju MIP-1β i RANTES aktivnosti koja je posredovana CCR5 receptorom u bolesnika kojemu je to potrebno.
19. Uporaba spoja prema bilo kojem od zahtjeva 1 do u pripremi lijeka za inhibiciju CCR2 i CCR5 aktivnosti u bolesnika kojemu je to potrebno.
20. Spoj prema bilo kojem od zahtjeva 1-11, za uporabu u liječenju poremećaja izabranog između alveolitisa, kolitisa, sistemskog lupus eritematosus, nefrotoksičnog serumskog nefritisa, glomerulonefritisa, astme, multiple skleroze, ateroskleroze, reumatoidnog artritisa, restenoze, transplantacije organa i raka.
21. Spoj prema bilo kojem od zahtjeva 1-11, za uporabu u liječenju poremećaja izabranog između astme, multiple skleroze, ateroskleroze, i reumatoidnog artritisa.
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DE10135043A1 (de) | 2001-07-11 | 2003-01-30 | Bayer Cropscience Gmbh | Substituierte 3-Heteroaryl(amino- oder oxy)-pyrrolidin-2-one, Verfahren zu deren Herstellung und Verwendung als Herbizide oder als Pflanzenwachstumsregulatoren |
WO2003065692A1 (fr) * | 2002-01-31 | 2003-08-07 | Sanyo Electric Co., Ltd. | Telephone cellulaire |
WO2003075853A2 (en) | 2002-03-08 | 2003-09-18 | Bristol-Myers Squibb Company | Cyclic derivatives as modulators of chemokine receptor activity |
TW200307667A (en) | 2002-05-06 | 2003-12-16 | Bristol Myers Squibb Co | Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors |
AU2003263393A1 (en) | 2002-09-04 | 2004-03-29 | Glenmark Pharmaceuticals Limited | New heterocyclic amide compounds useful for the treatment of inflammatory and allergic disorders: process for their preparation and pharmaceutical compositions containing them |
TW200508224A (en) | 2003-02-12 | 2005-03-01 | Bristol Myers Squibb Co | Cyclic derivatives as modulators of chemokine receptor activity |
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-
2004
- 2004-08-19 US US10/923,619 patent/US7163937B2/en not_active Expired - Lifetime
- 2004-08-20 RS YUP-2006/0116A patent/RS20060116A/sr unknown
- 2004-08-20 MX MXPA06001819A patent/MXPA06001819A/es active IP Right Grant
- 2004-08-20 SI SI200432117T patent/SI1656345T1/sl unknown
- 2004-08-20 WO PCT/US2004/027196 patent/WO2005021500A1/en active Application Filing
- 2004-08-20 DK DK04781806.7T patent/DK1656345T3/da active
- 2004-08-20 PT PT47818067T patent/PT1656345E/pt unknown
- 2004-08-20 ES ES04781806.7T patent/ES2437104T3/es not_active Expired - Lifetime
- 2004-08-20 KR KR1020067003442A patent/KR101120338B1/ko not_active IP Right Cessation
- 2004-08-20 NZ NZ545317A patent/NZ545317A/en not_active IP Right Cessation
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- 2004-08-20 EP EP04781806.7A patent/EP1656345B1/en not_active Expired - Lifetime
- 2004-08-20 AU AU2004268968A patent/AU2004268968B2/en not_active Ceased
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- 2006-10-10 US US11/545,415 patent/US7482335B2/en not_active Expired - Lifetime
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2009
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2013
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