IL179167A

IL179167A - Compounds which act on 11bhsd1, pharmaceutical compositions comprising them and their use

Compounds which act on 11bhsd1, pharmaceutical compositions comprising them and their use

Info

Publication number: IL179167A
Authority: IL; Israel
Prior art keywords: thiazol; alkyl; amino; ylamino; bicyclo
Prior art date: 2004-05-24

Application number

IL179167A

Other languages

English (en)

Other versions

IL179167A0 (en

Original Assignee

Biovitrum Ab

Amgen Inc

Priority date

2004-05-24

Filing date

2006-11-09

Publication date

2012-01-31

2004-05-24 Priority claimed from SE0401324A external-priority patent/SE0401324D0/xx

2004-10-15 Priority claimed from SE0402509A external-priority patent/SE0402509D0/xx

2005-05-24 Priority claimed from PCT/US2005/018081 external-priority patent/WO2005116002A2/en

2006-11-09 Application filed by Biovitrum Ab, Amgen Inc filed Critical Biovitrum Ab

2007-03-08 Publication of IL179167A0 publication Critical patent/IL179167A0/en

2012-01-31 Publication of IL179167A publication Critical patent/IL179167A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 190
239000008194 pharmaceutical composition Substances 0.000 title claims description 12
238000000034 method Methods 0.000 claims description 269
239000000203 mixture Substances 0.000 claims description 127
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 101
-1 aryl-Ci-8- alkyl Chemical group 0.000 claims description 93
125000003118 aryl group Chemical group 0.000 claims description 65
238000006243 chemical reaction Methods 0.000 claims description 62
238000011282 treatment Methods 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 57
125000000623 heterocyclic group Chemical group 0.000 claims description 57
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 44
239000003862 glucocorticoid Substances 0.000 claims description 41
125000003545 alkoxy group Chemical group 0.000 claims description 26
229920006395 saturated elastomer Polymers 0.000 claims description 25
230000003287 optical effect Effects 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 23
239000012453 solvate Substances 0.000 claims description 23
150000001204 N-oxides Chemical class 0.000 claims description 22
229940037128 systemic glucocorticoids Drugs 0.000 claims description 22
NNFCIYWJLLJEMN-UHFFFAOYSA-N dec-2-en-4-one Chemical compound CCCCCCC(=O)C=CC NNFCIYWJLLJEMN-UHFFFAOYSA-N 0.000 claims description 20
230000029663 wound healing Effects 0.000 claims description 20
102000004190 Enzymes Human genes 0.000 claims description 19
108090000790 Enzymes Proteins 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000001475 halogen functional group Chemical group 0.000 claims description 17
206010052428 Wound Diseases 0.000 claims description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
208000027418 Wounds and injury Diseases 0.000 claims description 14
206010012601 diabetes mellitus Diseases 0.000 claims description 14
150000004677 hydrates Chemical class 0.000 claims description 14
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 13
WTAYWTBOEQYGOG-QPJJXVBHSA-N 2-Nonen-4-one Chemical compound CCCCCC(=O)\C=C\C WTAYWTBOEQYGOG-QPJJXVBHSA-N 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 9
208000008589 Obesity Diseases 0.000 claims description 9
208000001132 Osteoporosis Diseases 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
235000020824 obesity Nutrition 0.000 claims description 9
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 8
206010020772 Hypertension Diseases 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
230000001771 impaired effect Effects 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
125000005309 thioalkoxy group Chemical group 0.000 claims description 7
102000008645 11-beta-Hydroxysteroid Dehydrogenase Type 1 Human genes 0.000 claims description 6
108010088011 11-beta-Hydroxysteroid Dehydrogenase Type 1 Proteins 0.000 claims description 6
208000010412 Glaucoma Diseases 0.000 claims description 6
230000003111 delayed effect Effects 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
230000001404 mediated effect Effects 0.000 claims description 6
UAXDBJVXVXJQFJ-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)SC11CCCC1 UAXDBJVXVXJQFJ-UHFFFAOYSA-N 0.000 claims description 5
YZDLNOVQXOSMBO-UHFFFAOYSA-N 2-(cycloheptylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound S1C2(CCCC2)C(=O)N=C1NC1CCCCCC1 YZDLNOVQXOSMBO-UHFFFAOYSA-N 0.000 claims description 5
JRXIMHQYNOCOAW-UHFFFAOYSA-N 2-(cyclooctylamino)-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound S1C2(CCCC2)C(=O)N=C1NC1CCCCCCC1 JRXIMHQYNOCOAW-UHFFFAOYSA-N 0.000 claims description 5
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
125000001072 heteroaryl group Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
229910052744 lithium Inorganic materials 0.000 claims description 5
AOPPTZIKPLJWDF-UHFFFAOYSA-N 2-(cyclooctylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound S1C2(CCCCC2)C(=O)N=C1NC1CCCCCCC1 AOPPTZIKPLJWDF-UHFFFAOYSA-N 0.000 claims description 4
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
YNBPGJSIXHBKLU-UHFFFAOYSA-N 6-(2-methylanilino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound CC1=CC=CC=C1NC(S1)=NC(=O)C11CCC1 YNBPGJSIXHBKLU-UHFFFAOYSA-N 0.000 claims description 4
GBHCRZABOYORSW-UHFFFAOYSA-N 6-(3-bicyclo[2.2.1]heptanylamino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)SC11CCC1 GBHCRZABOYORSW-UHFFFAOYSA-N 0.000 claims description 4
YNNSXEVWOODRDZ-UHFFFAOYSA-N 6-(cycloheptylamino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound S1C2(CCC2)C(=O)N=C1NC1CCCCCC1 YNNSXEVWOODRDZ-UHFFFAOYSA-N 0.000 claims description 4
SKXWISZNEAWCJW-UHFFFAOYSA-N 6-(cyclooctylamino)-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound S1C2(CCC2)C(=O)N=C1NC1CCCCCCC1 SKXWISZNEAWCJW-UHFFFAOYSA-N 0.000 claims description 4
101710088194 Dehydrogenase Proteins 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
238000011321 prophylaxis Methods 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
BOQWDXXFGRRTMJ-MRVPVSSYSA-N (5r)-2-(cycloheptylamino)-5-methyl-1,3-thiazol-4-one Chemical compound O=C1[C@@H](C)SC(NC2CCCCCC2)=N1 BOQWDXXFGRRTMJ-MRVPVSSYSA-N 0.000 claims description 3
VXWZKCPEMUMBQL-RJRLTIMHSA-N (5s)-2-[[(1r,4r,5s)-2-hydroxy-5-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound N([C@H]1C[C@@]2(C(C[C@@]1([H])C2)O)[H])C1=NC(=O)[C@](C)(C(C)C)S1 VXWZKCPEMUMBQL-RJRLTIMHSA-N 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
MWALCPLMKFAAPN-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)SC11CCCCC1 MWALCPLMKFAAPN-UHFFFAOYSA-N 0.000 claims description 3
BALONPGGQKBAOK-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-[(4-hydroxyphenyl)methyl]-1,3-thiazol-4-one Chemical compound C1=CC(O)=CC=C1CC1C(=O)N=C(NC2C3CCC(C3)C2)S1 BALONPGGQKBAOK-UHFFFAOYSA-N 0.000 claims description 3
YCNCXQNUXCHRRX-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical group O=C1C(C(C)C)(C)SC(NC2C3CCC(C3)C2)=N1 YCNCXQNUXCHRRX-UHFFFAOYSA-N 0.000 claims description 3
PBOZAHAHLGEZDH-UHFFFAOYSA-N 2-(cycloheptylamino)-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound S1C2(CCCCC2)C(=O)N=C1NC1CCCCCC1 PBOZAHAHLGEZDH-UHFFFAOYSA-N 0.000 claims description 3
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 3
BVBRHUUYFYAHST-UHFFFAOYSA-N 6-(3-tricyclo[3.3.1.03,7]nonanylimino)-5-thia-7-azaspiro[3.4]octan-8-one Chemical compound O=C1N=C(NC23C4CC(CC(C3)C4)C2)SC11CCC1 BVBRHUUYFYAHST-UHFFFAOYSA-N 0.000 claims description 3
206010012289 Dementia Diseases 0.000 claims description 3
206010060378 Hyperinsulinaemia Diseases 0.000 claims description 3
241000236488 Lepra Species 0.000 claims description 3
206010024229 Leprosy Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
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 description 3
150000004820 halides Chemical class 0.000 claims description 3
201000001421 hyperglycemia Diseases 0.000 claims description 3
230000003451 hyperinsulinaemic effect Effects 0.000 claims description 3
201000008980 hyperinsulinism Diseases 0.000 claims description 3
230000002519 immonomodulatory effect Effects 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
201000008827 tuberculosis Diseases 0.000 claims description 3
XSTQWNZHFKKBBT-KKSJPVRNSA-N (5s)-2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[(2s)-1-hydroxypropan-2-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)[C@](C)([C@@H](C)CO)S1 XSTQWNZHFKKBBT-KKSJPVRNSA-N 0.000 claims description 2
VXWZKCPEMUMBQL-JNQPULAQSA-N (5s)-2-[[(1r,4r,5r)-2-hydroxy-5-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical group N([C@@H]1C[C@@]2(C(C[C@@]1([H])C2)O)[H])C1=NC(=O)[C@](C)(C(C)C)S1 VXWZKCPEMUMBQL-JNQPULAQSA-N 0.000 claims description 2
SUBUXFVWUBEELD-AAEUAGOBSA-N (5s)-2-[[(2r)-2-phenylpropyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@H](C(C)C)SC(NC[C@H](C)C=2C=CC=CC=2)=N1 SUBUXFVWUBEELD-AAEUAGOBSA-N 0.000 claims description 2
SUBUXFVWUBEELD-YPMHNXCESA-N (5s)-2-[[(2s)-2-phenylpropyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1[C@H](C(C)C)SC(NC[C@@H](C)C=2C=CC=CC=2)=N1 SUBUXFVWUBEELD-YPMHNXCESA-N 0.000 claims description 2
RTQSUSWTUGCXER-UHFFFAOYSA-N 2-(1-cyclohexylethylamino)-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)(C)SC(NC(C)C2CCCCC2)=N1 RTQSUSWTUGCXER-UHFFFAOYSA-N 0.000 claims description 2
GZCSXGUKZIGILY-UHFFFAOYSA-N 2-(cycloheptylamino)-5-(1h-indol-3-ylmethyl)-1,3-thiazol-4-one Chemical compound S1C(CC=2C3=CC=CC=C3NC=2)C(=O)N=C1NC1CCCCCC1 GZCSXGUKZIGILY-UHFFFAOYSA-N 0.000 claims description 2
NHWXFERNEQMAPC-UHFFFAOYSA-N 2-(cyclooctylamino)-5-[(4-hydroxyphenyl)methyl]-1,3-thiazol-4-one Chemical compound C1=CC(O)=CC=C1CC1C(=O)N=C(NC2CCCCCCC2)S1 NHWXFERNEQMAPC-UHFFFAOYSA-N 0.000 claims description 2
CFPUUJOXOXNDQW-UHFFFAOYSA-N 2-[(2,2,3,3-tetramethylcyclopropyl)amino]-1-thia-3-azaspiro[4.4]non-2-en-4-one Chemical compound CC1(C)C(C)(C)C1NC(S1)=NC(=O)C11CCCC1 CFPUUJOXOXNDQW-UHFFFAOYSA-N 0.000 claims description 2
GUGBDNQGYWHFSW-HBNTYKKESA-N 2-[[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]amino]-8-oxa-1-thia-3-azaspiro[4.5]dec-2-en-4-one Chemical compound N([C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C(S1)=NC(=O)C21CCOCC2 GUGBDNQGYWHFSW-HBNTYKKESA-N 0.000 claims description 2
XLFDGKZAEMQJBH-UHFFFAOYSA-N 2-anilino-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C=CC=CC=2)=N1 XLFDGKZAEMQJBH-UHFFFAOYSA-N 0.000 claims description 2
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims description 2
BWDDIHJHDZPIAR-UHFFFAOYSA-N 6-[(2,2,3,3-tetramethylcyclopropyl)amino]-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound CC1(C)C(C)(C)C1NC(S1)=NC(=O)C11CCC1 BWDDIHJHDZPIAR-UHFFFAOYSA-N 0.000 claims description 2
DHGDFKXJSGECLO-UHFFFAOYSA-N 6-[[1-(4-chlorophenyl)cyclobutyl]amino]-5-thia-7-azaspiro[3.4]oct-6-en-8-one Chemical compound C1=CC(Cl)=CC=C1C1(NC=2SC3(CCC3)C(=O)N=2)CCC1 DHGDFKXJSGECLO-UHFFFAOYSA-N 0.000 claims description 2
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 claims description 2
206010056340 Diabetic ulcer Diseases 0.000 claims description 2
208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
208000004210 Pressure Ulcer Diseases 0.000 claims description 2
208000000558 Varicose Ulcer Diseases 0.000 claims description 2
241000700605 Viruses Species 0.000 claims description 2
230000001684 chronic effect Effects 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
238000009472 formulation Methods 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
JIOXZNMZWIIEOG-UHFFFAOYSA-N 2-(cycloheptylamino)-5-(1h-imidazol-5-ylmethyl)-1,3-thiazol-4-one Chemical compound S1C(CC=2N=CNC=2)C(=O)N=C1NC1CCCCCC1 JIOXZNMZWIIEOG-UHFFFAOYSA-N 0.000 claims 2
MGNAKJDWBJUEEW-UHFFFAOYSA-N 2-[[1-(4-chlorophenyl)cyclobutyl]amino]-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC2(CCC2)C=2C=CC(Cl)=CC=2)=N1 MGNAKJDWBJUEEW-UHFFFAOYSA-N 0.000 claims 2
HWVCGKOGMAXCRS-UHFFFAOYSA-N 5-(cyclohexylmethylamino)-4-thia-6-azaspiro[2.4]hept-5-en-7-one Chemical compound S1C2(CC2)C(=O)N=C1NCC1CCCCC1 HWVCGKOGMAXCRS-UHFFFAOYSA-N 0.000 claims 2
KMJISCSUVGMRLG-CMPLNLGQSA-N (5r)-5-ethyl-2-[[(2r)-2-phenylpropyl]amino]-1,3-thiazol-4-one Chemical compound O=C1[C@@H](CC)SC(NC[C@H](C)C=2C=CC=CC=2)=N1 KMJISCSUVGMRLG-CMPLNLGQSA-N 0.000 claims 1
KMJISCSUVGMRLG-ZYHUDNBSSA-N (5r)-5-ethyl-2-[[(2s)-2-phenylpropyl]amino]-1,3-thiazol-4-one Chemical compound O=C1[C@@H](CC)SC(NC[C@@H](C)C=2C=CC=CC=2)=N1 KMJISCSUVGMRLG-ZYHUDNBSSA-N 0.000 claims 1
XSTQWNZHFKKBBT-WCCFOQQASA-N (5s)-2-[[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]amino]-5-[(2r)-1-hydroxypropan-2-yl]-5-methyl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C1=NC(=O)[C@](C)([C@H](C)CO)S1 XSTQWNZHFKKBBT-WCCFOQQASA-N 0.000 claims 1
KIYQVTDQWYFUPA-JVXAONJBSA-N (5s)-2-[[(1r,4s,5s)-3-hydroxy-5-bicyclo[2.2.1]heptanyl]amino]-5-methyl-5-propan-2-yl-1,3-thiazol-4-one Chemical compound N([C@@H]1[C@@]2([H])C(O)C[C@](C2)(C1)[H])C1=NC(=O)[C@](C)(C(C)C)S1 KIYQVTDQWYFUPA-JVXAONJBSA-N 0.000 claims 1
WTDVJQRSTXJXKV-UHFFFAOYSA-N 2-(2-methylanilino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC=2C(=CC=CC=2)C)=N1 WTDVJQRSTXJXKV-UHFFFAOYSA-N 0.000 claims 1
GLUAKGKNBDZINR-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5,5-dimethyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(C)SC(NC2C3CCC(C3)C2)=N1 GLUAKGKNBDZINR-UHFFFAOYSA-N 0.000 claims 1
SIDMUSMJMIZMKV-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC2C3CCC(C3)C2)=N1 SIDMUSMJMIZMKV-UHFFFAOYSA-N 0.000 claims 1
ACLPTGFAHZHQDB-UHFFFAOYSA-N 2-(3-bicyclo[2.2.1]heptanylamino)-5-phenyl-1,3-thiazol-4-one Chemical compound O=C1N=C(NC2C3CCC(C3)C2)SC1C1=CC=CC=C1 ACLPTGFAHZHQDB-UHFFFAOYSA-N 0.000 claims 1
NRVZPJUAZVHNMN-UHFFFAOYSA-N 2-(cyclohexylamino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC2CCCCC2)=N1 NRVZPJUAZVHNMN-UHFFFAOYSA-N 0.000 claims 1
PERAPCUCBBSZOT-UHFFFAOYSA-N 2-(cyclohexylmethylamino)-5,5-dimethyl-1,3-thiazol-4-one Chemical compound O=C1C(C)(C)SC(NCC2CCCCC2)=N1 PERAPCUCBBSZOT-UHFFFAOYSA-N 0.000 claims 1
RQCIJBSJBFMYBX-UHFFFAOYSA-N 2-(cyclooctylamino)-5-ethyl-1,3-thiazol-4-one Chemical compound O=C1C(CC)SC(NC2CCCCCCC2)=N1 RQCIJBSJBFMYBX-UHFFFAOYSA-N 0.000 claims 1
UNUWSRCQXRZZAT-UHFFFAOYSA-N 2-(cyclooctylamino)-5-propan-2-yl-1,3-thiazol-4-one Chemical compound O=C1C(C(C)C)SC(NC2CCCCCCC2)=N1 UNUWSRCQXRZZAT-UHFFFAOYSA-N 0.000 claims 1
UNJGDEQMIBHKEY-UHFFFAOYSA-N 2-[1-(2-fluorophenyl)ethylamino]-5-(2-fluoropropan-2-yl)-5-methyl-1,3-thiazol-4-one Chemical compound C=1C=CC=C(F)C=1C(C)NC1=NC(=O)C(C)(C(C)(C)F)S1 UNJGDEQMIBHKEY-UHFFFAOYSA-N 0.000 claims 1
MWNAPXWHHGHKAK-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)ethylamino]-5-methyl-5-pyridin-4-yl-1,3-thiazol-4-one Chemical compound C=1C=C(F)C=CC=1C(C)NC(S1)=NC(=O)C1(C)C1=CC=NC=C1 MWNAPXWHHGHKAK-UHFFFAOYSA-N 0.000 claims 1
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