ZA200503959B - 1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands - Google Patents
1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands Download PDFInfo
- Publication number
- ZA200503959B ZA200503959B ZA200503959A ZA200503959A ZA200503959B ZA 200503959 B ZA200503959 B ZA 200503959B ZA 200503959 A ZA200503959 A ZA 200503959A ZA 200503959 A ZA200503959 A ZA 200503959A ZA 200503959 B ZA200503959 B ZA 200503959B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- methyl
- quinolin
- fluoro
- trifluoromethylpentyl
- Prior art date
Links
- 239000003862 glucocorticoid Substances 0.000 title claims description 30
- 239000003446 ligand Substances 0.000 title description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 title description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- -1 aminocarbonyloxy Chemical group 0.000 claims description 77
- 125000001424 substituent group Chemical group 0.000 claims description 57
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 50
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 229940002612 prodrug Drugs 0.000 claims description 29
- 239000000651 prodrug Substances 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000004043 oxo group Chemical group O=* 0.000 claims description 22
- 150000003457 sulfones Chemical class 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 150000003462 sulfoxides Chemical class 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000004434 sulfur atom Chemical group 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 15
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 14
- 102000003676 Glucocorticoid Receptors Human genes 0.000 claims description 13
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 230000002757 inflammatory effect Effects 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 9
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 9
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 8
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000003003 spiro group Chemical group 0.000 claims description 8
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- IVKNUIVDQMARCO-UHFFFAOYSA-N oxazin-4-one Chemical compound O=C1C=CON=C1 IVKNUIVDQMARCO-UHFFFAOYSA-N 0.000 claims description 7
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 102000005962 receptors Human genes 0.000 claims description 6
- 108020003175 receptors Proteins 0.000 claims description 6
- 230000000172 allergic effect Effects 0.000 claims description 5
- 208000010668 atopic eczema Diseases 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000025747 Rheumatic disease Diseases 0.000 claims description 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 4
- DHZYXWMZLAKTQV-UHFFFAOYSA-N diazepin-3-one Chemical compound O=C1C=CC=CN=N1 DHZYXWMZLAKTQV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- SJSABZBUTDSWMJ-UHFFFAOYSA-N pyrrolo[3,4-c]pyridine-1,3-dione Chemical compound N1=CC=C2C(=O)NC(=O)C2=C1 SJSABZBUTDSWMJ-UHFFFAOYSA-N 0.000 claims description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
- 238000002054 transplantation Methods 0.000 claims description 4
- NENLYAQPNATJSU-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline Chemical compound C1NCCC2CCCCC21 NENLYAQPNATJSU-UHFFFAOYSA-N 0.000 claims description 3
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 3
- SWEICGMKXPNXNU-UHFFFAOYSA-N 1,2-dihydroindazol-3-one Chemical compound C1=CC=C2C(O)=NNC2=C1 SWEICGMKXPNXNU-UHFFFAOYSA-N 0.000 claims description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 3
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims description 3
- WYLSGWZVDHQRNX-UHFFFAOYSA-N 2-(3,4-dimethoxy-n-(4-methylphenyl)sulfonylanilino)-n-(2,4-dimethylpentan-3-yl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1N(CC(=O)NC(C(C)C)C(C)C)S(=O)(=O)C1=CC=C(C)C=C1 WYLSGWZVDHQRNX-UHFFFAOYSA-N 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 3
- MWRKXVUGPRFLTD-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-1h-1,8-naphthyridin-2-one Chemical compound C1C=CN=C2NC(=O)CCC21 MWRKXVUGPRFLTD-UHFFFAOYSA-N 0.000 claims description 3
- YBBLSBDJIKMXNQ-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzothiazine Chemical compound C1=CC=C2NCCSC2=C1 YBBLSBDJIKMXNQ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- HORKYAIEVBUXGM-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoxaline Chemical compound C1=CC=C2NCCNC2=C1 HORKYAIEVBUXGM-UHFFFAOYSA-N 0.000 claims description 2
- ROSODFDWJFAKQI-UHFFFAOYSA-N 1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NC=C2C(=O)NCC2=C1 ROSODFDWJFAKQI-UHFFFAOYSA-N 0.000 claims description 2
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 claims description 2
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 2
- NSPLFNGUPLZYHV-UHFFFAOYSA-N 1h-1,5-naphthyridin-4-one Chemical compound C1=CN=C2C(O)=CC=NC2=C1 NSPLFNGUPLZYHV-UHFFFAOYSA-N 0.000 claims description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
- YMMHAIJRFWRDMG-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-1h-quinolin-2-one Chemical compound C1C=CC=C2NC(=O)CCC21 YMMHAIJRFWRDMG-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
- CYJAWBVQRMVFEO-UHFFFAOYSA-N piperazine-2,6-dione Chemical compound O=C1CNCC(=O)N1 CYJAWBVQRMVFEO-UHFFFAOYSA-N 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- PMZDQRJGMBOQBF-UHFFFAOYSA-N 1H-quinolin-4-one Natural products C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 claims 126
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 10
- 150000002148 esters Chemical class 0.000 claims 9
- VSGPVHSTVTXREH-UHFFFAOYSA-N quinolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=CN=C21 VSGPVHSTVTXREH-UHFFFAOYSA-N 0.000 claims 9
- 208000002193 Pain Diseases 0.000 claims 7
- 208000014674 injury Diseases 0.000 claims 7
- 208000012902 Nervous system disease Diseases 0.000 claims 6
- 208000025966 Neurological disease Diseases 0.000 claims 6
- 230000001154 acute effect Effects 0.000 claims 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims 6
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 5
- 208000027418 Wounds and injury Diseases 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 4
- 230000006378 damage Effects 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 201000001320 Atherosclerosis Diseases 0.000 claims 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 3
- 208000019693 Lung disease Diseases 0.000 claims 3
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 3
- 206010051606 Necrotising colitis Diseases 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims 3
- 206010047115 Vasculitis Diseases 0.000 claims 3
- 230000001919 adrenal effect Effects 0.000 claims 3
- 208000024447 adrenal gland neoplasm Diseases 0.000 claims 3
- 208000026935 allergic disease Diseases 0.000 claims 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
- 208000019664 bone resorption disease Diseases 0.000 claims 3
- 208000030172 endocrine system disease Diseases 0.000 claims 3
- 208000030533 eye disease Diseases 0.000 claims 3
- 210000003714 granulocyte Anatomy 0.000 claims 3
- 238000001631 haemodialysis Methods 0.000 claims 3
- 208000014951 hematologic disease Diseases 0.000 claims 3
- 230000000322 hemodialysis Effects 0.000 claims 3
- 208000017169 kidney disease Diseases 0.000 claims 3
- 208000019423 liver disease Diseases 0.000 claims 3
- 208000037890 multiple organ injury Diseases 0.000 claims 3
- 208000010125 myocardial infarction Diseases 0.000 claims 3
- 208000004995 necrotizing enterocolitis Diseases 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 210000000056 organ Anatomy 0.000 claims 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims 3
- 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 claims 3
- 230000002062 proliferating effect Effects 0.000 claims 3
- 208000037803 restenosis Diseases 0.000 claims 3
- 230000035939 shock Effects 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- 210000001519 tissue Anatomy 0.000 claims 3
- 230000008733 trauma Effects 0.000 claims 3
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims 2
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 2
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 2
- KFLMSHBVMPZGFE-UHFFFAOYSA-N 1-[2-hydroxy-4-(2-methoxy-5-pyridin-3-ylphenyl)-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=C(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)C(OC)=CC=C1C1=CC=CN=C1 KFLMSHBVMPZGFE-UHFFFAOYSA-N 0.000 claims 2
- JTMSOPRMNMRXRT-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-4-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=CC2=C1OCO2 JTMSOPRMNMRXRT-UHFFFAOYSA-N 0.000 claims 2
- RSPFQPBIFPECRA-UHFFFAOYSA-N 1-[4-(5-fluoro-2-phenylmethoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OCC1=CC=CC=C1 RSPFQPBIFPECRA-UHFFFAOYSA-N 0.000 claims 2
- UFMBERDMCRCVSM-UHFFFAOYSA-N 1h-cinnolin-4-one Chemical compound C1=CC=C2C(O)=CN=NC2=C1 UFMBERDMCRCVSM-UHFFFAOYSA-N 0.000 claims 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 claims 2
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 2
- 208000012659 Joint disease Diseases 0.000 claims 2
- 201000009906 Meningitis Diseases 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 208000005298 acute pain Diseases 0.000 claims 2
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 2
- 238000007887 coronary angioplasty Methods 0.000 claims 2
- 125000005265 dialkylamine group Chemical group 0.000 claims 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 2
- DWLVWMUCHSLGSU-UHFFFAOYSA-N dimethylcarbamic acid Chemical compound CN(C)C(O)=O DWLVWMUCHSLGSU-UHFFFAOYSA-N 0.000 claims 2
- KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical compound CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 claims 2
- LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-UHFFFAOYSA-N 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- DZURPZLMFFCDLO-UHFFFAOYSA-N (2,2,3,3-tetramethylcyclopropyl)carbamic acid Chemical compound CC1(C)C(NC(O)=O)C1(C)C DZURPZLMFFCDLO-UHFFFAOYSA-N 0.000 claims 1
- SELSOWQGQHXLRG-UHFFFAOYSA-N 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]pentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1CCN(C=2N=CC=CN=2)CC1 SELSOWQGQHXLRG-UHFFFAOYSA-N 0.000 claims 1
- WUKHDMKITXNHQL-UHFFFAOYSA-N 1,2-dihydropyrido[3,2-d][1,3]oxazin-4-one Chemical compound C1=CN=C2C(=O)OCNC2=C1 WUKHDMKITXNHQL-UHFFFAOYSA-N 0.000 claims 1
- YLRRFARMTNWZKA-UHFFFAOYSA-N 1,2-dimethylpiperidin-4-one Chemical compound CC1CC(=O)CCN1C YLRRFARMTNWZKA-UHFFFAOYSA-N 0.000 claims 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 1
- WSMNCAPPEXBZHI-UHFFFAOYSA-N 1-[2-hydroxy-4-(2-hydroxy-3,5-dimethylphenyl)-4-methyl-2-(trifluoromethyl)pentyl]-3-methylquinolin-4-one Chemical compound CC1=CC(C)=C(O)C(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C(C)=C2)C(F)(F)F)=C1 WSMNCAPPEXBZHI-UHFFFAOYSA-N 0.000 claims 1
- PIUKGCFHXLVZSM-UHFFFAOYSA-N 1-[2-hydroxy-4-(2-hydroxy-3,5-dimethylphenyl)-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CC1=CC(C)=C(O)C(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 PIUKGCFHXLVZSM-UHFFFAOYSA-N 0.000 claims 1
- REEKGWMWTJMSCP-UHFFFAOYSA-N 1-[2-hydroxy-4-(2-hydroxy-3-phenylphenyl)-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C(C=1O)=CC=CC=1C1=CC=CC=C1 REEKGWMWTJMSCP-UHFFFAOYSA-N 0.000 claims 1
- ZXCRSPMVIMIGNN-UHFFFAOYSA-N 1-[2-hydroxy-4-(2-hydroxy-5-pyrimidin-5-ylphenyl)-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C(C(=CC=1)O)=CC=1C1=CN=CN=C1 ZXCRSPMVIMIGNN-UHFFFAOYSA-N 0.000 claims 1
- AJIYDXFOGMHOGN-UHFFFAOYSA-N 1-[2-hydroxy-4-(2-methoxy-3,5-dimethylphenyl)-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound COC1=C(C)C=C(C)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(=O)C=C1 AJIYDXFOGMHOGN-UHFFFAOYSA-N 0.000 claims 1
- PQWVWNTUWREDFD-UHFFFAOYSA-N 1-[2-hydroxy-4-(2-methoxy-5-thiophen-2-ylphenyl)-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=C(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)C(OC)=CC=C1C1=CC=CS1 PQWVWNTUWREDFD-UHFFFAOYSA-N 0.000 claims 1
- YIMZSFXNNBDZOH-UHFFFAOYSA-N 1-[2-hydroxy-4-(3-methoxyphenyl)-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical class COC1=CC=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 YIMZSFXNNBDZOH-UHFFFAOYSA-N 0.000 claims 1
- JPRRCWQCHQWROA-UHFFFAOYSA-N 1-[2-hydroxy-4-[3-[(3-hydroxypyrrolidin-1-yl)methyl]phenyl]-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C(C=1)=CC=CC=1CN1CCC(O)C1 JPRRCWQCHQWROA-UHFFFAOYSA-N 0.000 claims 1
- JFGWACUUTVOWHL-UHFFFAOYSA-N 1-[2-hydroxy-4-methyl-4-(3-phenylphenyl)-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C(C=1)=CC=CC=1C1=CC=CC=C1 JFGWACUUTVOWHL-UHFFFAOYSA-N 0.000 claims 1
- ZGEXONNSMROENQ-UHFFFAOYSA-N 1-[2-hydroxy-4-methyl-4-(3-propan-2-yloxyphenyl)-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CC(C)OC1=CC=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 ZGEXONNSMROENQ-UHFFFAOYSA-N 0.000 claims 1
- FBJDMPCRJXWODV-UHFFFAOYSA-N 1-[2-hydroxy-4-methyl-4-(3-pyridin-3-ylphenyl)-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C(C=1)=CC=CC=1C1=CC=CN=C1 FBJDMPCRJXWODV-UHFFFAOYSA-N 0.000 claims 1
- QZYACYACUMOLBV-UHFFFAOYSA-N 1-[2-hydroxy-4-methyl-4-(5-methylsulfonyl-2,3-dihydro-1-benzofuran-7-yl)-2-(trifluoromethyl)pentyl]-3,5-dimethylpyridin-4-one Chemical compound C1=C(C)C(=O)C(C)=CN1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(S(C)(=O)=O)=CC2=C1OCC2 QZYACYACUMOLBV-UHFFFAOYSA-N 0.000 claims 1
- LPEODVMLFQMMHO-UHFFFAOYSA-N 1-[2-hydroxy-4-methyl-4-[3-(2-oxopropoxy)phenyl]-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CC(=O)COC1=CC=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 LPEODVMLFQMMHO-UHFFFAOYSA-N 0.000 claims 1
- YQYDHYOQGHYBHL-UHFFFAOYSA-N 1-[2-hydroxy-4-methyl-4-[3-(morpholin-4-ylmethyl)phenyl]-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C(C=1)=CC=CC=1CN1CCOCC1 YQYDHYOQGHYBHL-UHFFFAOYSA-N 0.000 claims 1
- DEQBSEVXHDSTRS-UHFFFAOYSA-N 1-[4-(2,4-dimethylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CC1=CC(C)=CC=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(=O)C=C1 DEQBSEVXHDSTRS-UHFFFAOYSA-N 0.000 claims 1
- OXJJMMSDOFXJSI-UHFFFAOYSA-N 1-[4-(3,4-dihydro-2h-chromen-8-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1CCOC2=C1C=CC=C2C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(=O)C=C1 OXJJMMSDOFXJSI-UHFFFAOYSA-N 0.000 claims 1
- HGXBGOPTUBIGQK-UHFFFAOYSA-N 1-[4-(3,5-difluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC(F)=C1 HGXBGOPTUBIGQK-UHFFFAOYSA-N 0.000 claims 1
- YYWAGWKEZUXODX-UHFFFAOYSA-N 1-[4-(3,5-dimethylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CC1=CC(C)=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 YYWAGWKEZUXODX-UHFFFAOYSA-N 0.000 claims 1
- NAUQEZCOOUYMCL-UHFFFAOYSA-N 1-[4-(3-acetylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CC(=O)C1=CC=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 NAUQEZCOOUYMCL-UHFFFAOYSA-N 0.000 claims 1
- HFSJYERQZOUDHG-UHFFFAOYSA-N 1-[4-(3-ethoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CCOC1=CC=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 HFSJYERQZOUDHG-UHFFFAOYSA-N 0.000 claims 1
- FLIQQXKZHMFPNX-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-3-propan-2-ylquinolin-4-one Chemical compound C12=CC=CC=C2C(=O)C(C(C)C)=CN1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 FLIQQXKZHMFPNX-UHFFFAOYSA-N 0.000 claims 1
- FSXYIBOBKUHJKO-UHFFFAOYSA-N 1-[4-(4-fluorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 FSXYIBOBKUHJKO-UHFFFAOYSA-N 0.000 claims 1
- YBPFOCRRJWUUJO-UHFFFAOYSA-N 1-[4-(5-acetyl-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound COC1=CC=C(C(C)=O)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(=O)C=C1 YBPFOCRRJWUUJO-UHFFFAOYSA-N 0.000 claims 1
- JBDLJHDVLZXQPM-UHFFFAOYSA-N 1-[4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound COC1=CC=C(Br)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(=O)C=C1 JBDLJHDVLZXQPM-UHFFFAOYSA-N 0.000 claims 1
- GWCHLOXFNOQGAD-UHFFFAOYSA-N 1-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-3-methylquinolin-4-one Chemical compound C12=CC=CC=C2C(=O)C(C)=CN1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O GWCHLOXFNOQGAD-UHFFFAOYSA-N 0.000 claims 1
- SNNRWCNXGKZUJK-UHFFFAOYSA-N 1-[4-(5-fluoro-2-hydroxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-7-hydroxyquinolin-4-one Chemical compound C1=CC(=O)C2=CC=C(O)C=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1O SNNRWCNXGKZUJK-UHFFFAOYSA-N 0.000 claims 1
- WHASCUJPCLZNNI-UHFFFAOYSA-N 1-[4-(5-fluoro-2-methoxyphenyl)-2-(fluoromethyl)-2-hydroxy-4-methylpentyl]quinolin-4-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(CF)CN1C2=CC=CC=C2C(=O)C=C1 WHASCUJPCLZNNI-UHFFFAOYSA-N 0.000 claims 1
- BUSFOGHPNRPNNG-UHFFFAOYSA-N 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-2h-indazol-3-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(=O)N1 BUSFOGHPNRPNNG-UHFFFAOYSA-N 0.000 claims 1
- GYFHCJODBQJBAH-UHFFFAOYSA-N 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-3h-indol-2-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2CC1=O GYFHCJODBQJBAH-UHFFFAOYSA-N 0.000 claims 1
- ZMBODQRATLFARV-UHFFFAOYSA-N 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-6-methylquinolin-4-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=C(C)C=C2C(=O)C=C1 ZMBODQRATLFARV-UHFFFAOYSA-N 0.000 claims 1
- UARQLVZEGSYUCJ-UHFFFAOYSA-N 1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-propan-2-ylpentyl]quinolin-4-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(C)C)CN1C2=CC=CC=C2C(=O)C=C1 UARQLVZEGSYUCJ-UHFFFAOYSA-N 0.000 claims 1
- NBCQSSGFXYDLQL-UHFFFAOYSA-N 1-[4-(5-fluoro-2-methylphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-3,3-dimethyl-2h-quinolin-4-one Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2C(=O)C(C)(C)C1 NBCQSSGFXYDLQL-UHFFFAOYSA-N 0.000 claims 1
- NOQDCKVDZMYZHM-UHFFFAOYSA-N 1-[4-[3-(1,3-dioxan-2-yl)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C(C=1)=CC=CC=1C1OCCCO1 NOQDCKVDZMYZHM-UHFFFAOYSA-N 0.000 claims 1
- UXTPDIXNBNTLQU-UHFFFAOYSA-N 1-[4-[3-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound CC1=NOC(C)=C1C1=CC=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 UXTPDIXNBNTLQU-UHFFFAOYSA-N 0.000 claims 1
- HGKWISBGOFYYKP-UHFFFAOYSA-N 1-[4-[3-[[3-(dimethylamino)pyrrolidin-1-yl]methyl]phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1C(N(C)C)CCN1CC1=CC=CC(C(C)(C)CC(O)(CN2C3=CC=CC=C3C(=O)C=C2)C(F)(F)F)=C1 HGKWISBGOFYYKP-UHFFFAOYSA-N 0.000 claims 1
- MDVSUWXXTWDHTK-UHFFFAOYSA-N 1-[4-cyclohexyl-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound C1=CC(=O)C2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1CCCCC1 MDVSUWXXTWDHTK-UHFFFAOYSA-N 0.000 claims 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims 1
- WFDUOXJKEHADRT-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1,5-benzodiazepine Chemical compound N1CCCNC2=CC=CC=C21 WFDUOXJKEHADRT-UHFFFAOYSA-N 0.000 claims 1
- PACKYNVUQVOINR-UHFFFAOYSA-N 2,3,4a,5-tetrahydro-1h-quinolin-4-one Chemical compound C1=CCC2C(=O)CCNC2=C1 PACKYNVUQVOINR-UHFFFAOYSA-N 0.000 claims 1
- ZCSZZRCQMGYDPB-UHFFFAOYSA-N 2,3-dihydro-1h-1,5-naphthyridin-4-one Chemical compound C1=CN=C2C(=O)CCNC2=C1 ZCSZZRCQMGYDPB-UHFFFAOYSA-N 0.000 claims 1
- BUWPZNOVIHAWHW-UHFFFAOYSA-N 2,3-dihydro-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CCNC2=C1 BUWPZNOVIHAWHW-UHFFFAOYSA-N 0.000 claims 1
- XSYDNOHKYPCPBK-UHFFFAOYSA-N 2-(2,3-dihydroindol-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2CC1 XSYDNOHKYPCPBK-UHFFFAOYSA-N 0.000 claims 1
- XJFMATJFYVPYBR-UHFFFAOYSA-N 2-(3,4-dihydro-2h-quinolin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2CCC1 XJFMATJFYVPYBR-UHFFFAOYSA-N 0.000 claims 1
- FWPHSRLSSLGKKX-UHFFFAOYSA-N 2-(3,4-dihydro-2h-quinoxalin-1-ylmethyl)-1,1,1-trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-ol Chemical compound C1CNC2=CC=CC=C2N1CC(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1 FWPHSRLSSLGKKX-UHFFFAOYSA-N 0.000 claims 1
- FGGNCXHTELBEET-UHFFFAOYSA-N 2-(3,4-dihydro-2h-quinoxalin-1-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2NCC1 FGGNCXHTELBEET-UHFFFAOYSA-N 0.000 claims 1
- YANJJZMVVBWOBL-UHFFFAOYSA-N 2-[[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]methyl]-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1CCN(C=2C(=CC(=CN=2)C(F)(F)F)Cl)CC1 YANJJZMVVBWOBL-UHFFFAOYSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- VTOFAGGGKJYRRI-UHFFFAOYSA-N 3-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinazolin-4-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C(=O)C2=CC=CC=C2N=C1 VTOFAGGGKJYRRI-UHFFFAOYSA-N 0.000 claims 1
- OYTLYOFEZPQDBO-UHFFFAOYSA-N 4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-1-methyl-3h-quinoxalin-2-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=CC=C2N(C)C(=O)C1 OYTLYOFEZPQDBO-UHFFFAOYSA-N 0.000 claims 1
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 1
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims 1
- ARIREUPIXAKDAY-UHFFFAOYSA-N 4-butylbenzaldehyde Chemical compound CCCCC1=CC=C(C=O)C=C1 ARIREUPIXAKDAY-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- ZLILRRGWBOKBIG-UHFFFAOYSA-N 4h-1,4-benzothiazine Chemical compound C1=CC=C2NC=CSC2=C1 ZLILRRGWBOKBIG-UHFFFAOYSA-N 0.000 claims 1
- VSKYPIQGPOXUOF-UHFFFAOYSA-N 6-fluoro-1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC=C(F)C=C2C(=O)C=C1 VSKYPIQGPOXUOF-UHFFFAOYSA-N 0.000 claims 1
- PMFYMHDLYGHSHY-UHFFFAOYSA-N 7-chloro-1-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]quinolin-4-one Chemical compound COC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)CN1C2=CC(Cl)=CC=C2C(=O)C=C1 PMFYMHDLYGHSHY-UHFFFAOYSA-N 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 1
- JHFINHOBWIGQHJ-UHFFFAOYSA-N cyclopropylcarbamic acid Chemical compound OC(=O)NC1CC1 JHFINHOBWIGQHJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- ZXQKYQVJDRTTLZ-UHFFFAOYSA-N n,n-diethylpiperidine-3-carboxamide Chemical compound CCN(CC)C(=O)C1CCCNC1 ZXQKYQVJDRTTLZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- MUKCXROGIQHFNN-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1.O=C1CNCCN1 MUKCXROGIQHFNN-UHFFFAOYSA-N 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 230000000552 rheumatic effect Effects 0.000 claims 1
- XKZRQNXDEHFYFM-UHFFFAOYSA-N tert-butyl 4-[4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentyl]-3-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate Chemical compound COC(=O)CC1CN(C(=O)OC(C)(C)C)CCN1CC(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1OC XKZRQNXDEHFYFM-UHFFFAOYSA-N 0.000 claims 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 claims 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 description 17
- 229940037128 systemic glucocorticoids Drugs 0.000 description 13
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 7
- 230000009229 glucose formation Effects 0.000 description 6
- 208000027866 inflammatory disease Diseases 0.000 description 5
- 230000003637 steroidlike Effects 0.000 description 5
- 230000035903 transrepression Effects 0.000 description 5
- 108010085012 Steroid Receptors Proteins 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 102000005969 steroid hormone receptors Human genes 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 208000026278 immune system disease Diseases 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- HYTIPJFUWHYQON-UHFFFAOYSA-N 3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC=C2NC(=O)CNC2=C1 HYTIPJFUWHYQON-UHFFFAOYSA-N 0.000 description 2
- 102000003979 Mineralocorticoid Receptors Human genes 0.000 description 2
- 108090000375 Mineralocorticoid Receptors Proteins 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000010494 dissociation reaction Methods 0.000 description 2
- 230000005593 dissociations Effects 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 239000002395 mineralocorticoid Substances 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 102000003998 progesterone receptors Human genes 0.000 description 2
- 108090000468 progesterone receptors Proteins 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- SPJLEQRFKKAENL-UHFFFAOYSA-N 1,2-dihydro-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OCNC2=C1 SPJLEQRFKKAENL-UHFFFAOYSA-N 0.000 description 1
- QMBIKDNTNNAHDU-UHFFFAOYSA-N 2,2-dimethylpiperazine-1-carbaldehyde Chemical compound CC1(C)CNCCN1C=O QMBIKDNTNNAHDU-UHFFFAOYSA-N 0.000 description 1
- YUCAWERYTVMQIV-UHFFFAOYSA-N 2h-quinoxaline-1-carbaldehyde Chemical compound C1=CC=C2N(C=O)CC=NC2=C1 YUCAWERYTVMQIV-UHFFFAOYSA-N 0.000 description 1
- JRIDNJRPMHCUMK-UHFFFAOYSA-N 3,3,3-triphenylpropanamide Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC(=O)N)C1=CC=CC=C1 JRIDNJRPMHCUMK-UHFFFAOYSA-N 0.000 description 1
- YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- ZGJDQLDCBPXGGF-UHFFFAOYSA-N 5,6,7,8-tetrahydro-1h-quinolin-4-one Chemical class C1CCCC2=C1NC=CC2=O ZGJDQLDCBPXGGF-UHFFFAOYSA-N 0.000 description 1
- YSMODUONRAFBET-UHFFFAOYSA-N 5-hydroxylysine Chemical group NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 230000004568 DNA-binding Effects 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 108700039691 Genetic Promoter Regions Proteins 0.000 description 1
- 229940123037 Glucocorticoid antagonist Drugs 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 206010019755 Hepatitis chronic active Diseases 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 108010057466 NF-kappa B Proteins 0.000 description 1
- 102000003945 NF-kappa B Human genes 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 208000000491 Tendinopathy Diseases 0.000 description 1
- 206010043255 Tendonitis Diseases 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 102000001307 androgen receptors Human genes 0.000 description 1
- 108010080146 androgen receptors Proteins 0.000 description 1
- 230000001399 anti-metabolic effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000009045 body homeostasis Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- BLSSXMNIDIBXEO-UHFFFAOYSA-N cinnolin-4-one Chemical compound C1=CC=C[C]2C(=O)C=NN=C21 BLSSXMNIDIBXEO-UHFFFAOYSA-N 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 230000009260 cross reactivity Effects 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 102000015694 estrogen receptors Human genes 0.000 description 1
- 108010038795 estrogen receptors Proteins 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003635 glucocorticoid antagonist Substances 0.000 description 1
- 229940124750 glucocorticoid receptor agonist Drugs 0.000 description 1
- 230000004110 gluconeogenesis Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006028 immune-suppresssive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 102000027411 intracellular receptors Human genes 0.000 description 1
- 108091008582 intracellular receptors Proteins 0.000 description 1
- 201000004990 juvenile ankylosing spondylitis Diseases 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000009456 molecular mechanism Effects 0.000 description 1
- 210000004789 organ system Anatomy 0.000 description 1
- 210000000963 osteoblast Anatomy 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- ICSAXRANXQSPQP-VUKDEKJYSA-M sodium;(5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate Chemical compound [Na+].S([C@@H]1[C@H](C(N1C=1C([O-])=O)=O)[C@H](O)C)C=1[C@H]1CCCO1 ICSAXRANXQSPQP-VUKDEKJYSA-M 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43792503P | 2003-01-03 | 2003-01-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200503959B true ZA200503959B (en) | 2006-10-25 |
Family
ID=36077523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200503959A ZA200503959B (en) | 2003-01-03 | 2005-05-17 | 1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN1735599A (zh) |
| ZA (1) | ZA200503959B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8138189B2 (en) * | 2009-03-26 | 2012-03-20 | Hoffman-La Roche Inc. | Substituted benzene compounds as modulators of the glucocorticoid receptor |
| CN115197200B (zh) * | 2022-06-29 | 2023-03-21 | 河南农业大学 | 一种三氟甲基叔醇及其合成方法和应用 |
-
2003
- 2003-12-18 CN CN 200380108207 patent/CN1735599A/zh active Pending
-
2005
- 2005-05-17 ZA ZA200503959A patent/ZA200503959B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1735599A (zh) | 2006-02-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10800750B2 (en) | Compounds and compositions for inhibition of FASN | |
| JP6695457B2 (ja) | エストロゲン受容体調節剤としての６，７−ジヒドロ−５ｈ−ベンゾ［７］アヌレン誘導体 | |
| JP6416275B2 (ja) | ヘテロアリールｓｙｋ阻害剤 | |
| US10780073B2 (en) | N4-phenyl-quinazoline-4-amine derivatives and related compounds as ErbB type I receptor tyrosine kinase inhibitors for the treatment of hyperproliferative diseases | |
| JP6182592B2 (ja) | アミノ−インドリル−置換イミダゾリル−ピリミジン及び医薬としてのその使用 | |
| JP5959537B2 (ja) | 置換ピリジニル−ピリミジン及び医薬としてのその使用 | |
| US8541404B2 (en) | Inhibitors of the human aldosterone synthase CYP11B2 | |
| JP6026441B2 (ja) | キナーゼ阻害剤としてのアミノキノリン | |
| US6710047B2 (en) | Phthalazines with angiogenesis inhibiting activity | |
| US7205295B2 (en) | Benzoxazin-3-ones and derivatives thereof as therapeutic agents | |
| US8658637B2 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions and uses thereof | |
| US7579469B2 (en) | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof | |
| HRP20110808T1 (hr) | Derivati piridazina | |
| KR101214031B1 (ko) | 피리미딘 유도체 | |
| IL171480A (en) | Aza spiro alkane derivatives as inhibitors of metalloproteases and pharmaceutical compositions and uses thereof | |
| EP1596656A2 (en) | Pyrazoles and methods of making and using the same | |
| MX2014000867A (es) | Quinolinas sustituidas y su uso como medicamentos. | |
| AU2009228649A1 (en) | Novel P2X7R antagonists and their use | |
| TW201425307A (zh) | 作為激酶抑制劑之胺基－喹啉類 | |
| US10689362B2 (en) | Quinoxaline compounds as type III receptor tyrosine kinase inhibitors | |
| ZA200503959B (en) | 1-propanol and 1-propylamine derivatives and their use as glucocorticoid ligands | |
| JP2007526242A (ja) | カンナビノイドｃｂ１受容体アゴニストとしての三環式１−［（３−インドール−３−イル）カルボニル］ピペラジン誘導体 |