CA2325069A1 - Use of corticotropin releasing factor antagonists and related compositions - Google Patents
Use of corticotropin releasing factor antagonists and related compositions Download PDFInfo
- Publication number
- CA2325069A1 CA2325069A1 CA002325069A CA2325069A CA2325069A1 CA 2325069 A1 CA2325069 A1 CA 2325069A1 CA 002325069 A CA002325069 A CA 002325069A CA 2325069 A CA2325069 A CA 2325069A CA 2325069 A1 CA2325069 A1 CA 2325069A1
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- CA
- Canada
- Prior art keywords
- alkyl
- methyl
- phenyl
- ethyl
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 239000000203 mixture Substances 0.000 title claims abstract description 30
- 229940122010 Corticotropin releasing factor antagonist Drugs 0.000 title claims description 61
- 239000002769 corticotropin releasing factor antagonist Substances 0.000 title claims description 61
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 29
- 241001465754 Metazoa Species 0.000 claims abstract description 22
- 229940126013 glucocorticoid receptor antagonist Drugs 0.000 claims abstract description 22
- 239000003850 glucocorticoid receptor antagonist Substances 0.000 claims abstract description 20
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 835
- -1 hydroxy, fluoro, chloro, bromo, iodo Chemical group 0.000 claims description 337
- 229910052739 hydrogen Inorganic materials 0.000 claims description 236
- 229910052799 carbon Inorganic materials 0.000 claims description 227
- 239000001257 hydrogen Substances 0.000 claims description 203
- 125000001424 substituent group Chemical group 0.000 claims description 126
- 125000001153 fluoro group Chemical group F* 0.000 claims description 124
- 229910052760 oxygen Inorganic materials 0.000 claims description 121
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 118
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 114
- 125000003118 aryl group Chemical group 0.000 claims description 107
- 125000005843 halogen group Chemical group 0.000 claims description 94
- 150000001875 compounds Chemical class 0.000 claims description 93
- 229910052717 sulfur Inorganic materials 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 87
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 86
- 229910052757 nitrogen Inorganic materials 0.000 claims description 82
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 81
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
- 125000003545 alkoxy group Chemical group 0.000 claims description 71
- 239000001301 oxygen Substances 0.000 claims description 59
- 125000002947 alkylene group Chemical group 0.000 claims description 58
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 53
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 125000004076 pyridyl group Chemical group 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 125000001624 naphthyl group Chemical group 0.000 claims description 38
- 239000011593 sulfur Substances 0.000 claims description 38
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 36
- 150000001721 carbon Chemical group 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 34
- 125000001475 halogen functional group Chemical group 0.000 claims description 33
- PTDNMMRRZVLGHU-UHFFFAOYSA-N phenanthrene-2-carboxamide Chemical compound C1=CC=C2C3=CC=C(C(=O)N)C=C3C=CC2=C1 PTDNMMRRZVLGHU-UHFFFAOYSA-N 0.000 claims description 33
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- YPWLZGITFNGGKW-UHFFFAOYSA-N 2-phenanthrol Chemical compound C1=CC=C2C3=CC=C(O)C=C3C=CC2=C1 YPWLZGITFNGGKW-UHFFFAOYSA-N 0.000 claims description 30
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 30
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 30
- 125000002883 imidazolyl group Chemical group 0.000 claims description 30
- 125000001041 indolyl group Chemical group 0.000 claims description 30
- 125000001544 thienyl group Chemical group 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 29
- 125000002541 furyl group Chemical group 0.000 claims description 29
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 28
- 125000004434 sulfur atom Chemical group 0.000 claims description 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 125000005493 quinolyl group Chemical group 0.000 claims description 26
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 25
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 24
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 125000002971 oxazolyl group Chemical group 0.000 claims description 21
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 21
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 21
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910020008 S(O) Inorganic materials 0.000 claims description 17
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000002757 morpholinyl group Chemical group 0.000 claims description 17
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 15
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 14
- 125000000335 thiazolyl group Chemical group 0.000 claims description 14
- 125000004001 thioalkyl group Chemical group 0.000 claims description 14
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 13
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 13
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 13
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 10
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical group O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 10
- OBYABPUZVBFQAU-UHFFFAOYSA-N 2-methyl-n-pentan-3-yl-8-(2,4,6-trimethylphenyl)quinolin-4-amine Chemical compound C1=CC=C2C(NC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C OBYABPUZVBFQAU-UHFFFAOYSA-N 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 239000000651 prodrug Substances 0.000 claims description 7
- 229940002612 prodrug Drugs 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- QUANHMWAGRHYSS-UHFFFAOYSA-N 2,5-dimethyl-4-pentan-3-yloxy-6-(2,4,6-trimethylphenoxy)pyrimidine Chemical compound CCC(CC)OC1=NC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C QUANHMWAGRHYSS-UHFFFAOYSA-N 0.000 claims description 6
- UCFKSOVFXKRDMS-UHFFFAOYSA-N 2,5-dimethyl-4-pentan-3-yloxy-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-b]pyridine Chemical compound C12=NC(C)=CC2=C(OC(CC)CC)C(C)=CN1C1=C(C)C=C(C)C=C1C UCFKSOVFXKRDMS-UHFFFAOYSA-N 0.000 claims description 6
- VKKFIULENLDJRO-UHFFFAOYSA-N 2,5-dimethyl-4-pentan-3-yloxy-7-(2,4,6-trimethylphenyl)pyrrolo[3,2-d]pyrimidine Chemical compound C=1N(C)C=2C(OC(CC)CC)=NC(C)=NC=2C=1C1=C(C)C=C(C)C=C1C VKKFIULENLDJRO-UHFFFAOYSA-N 0.000 claims description 6
- NIEKVPZHTADNKL-UHFFFAOYSA-N 2,5-dimethyl-7-pentan-3-yloxy-3-(2,4,6-trimethylphenyl)pyrazolo[1,5-a]pyrimidine Chemical compound CC1=NN2C(OC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C NIEKVPZHTADNKL-UHFFFAOYSA-N 0.000 claims description 6
- MFGOIKCRAMOZST-UHFFFAOYSA-N 2-[[2-methyl-8-(2,4,6-trimethylphenyl)quinolin-4-yl]amino]butan-1-ol Chemical compound C1=CC=C2C(NC(CO)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C MFGOIKCRAMOZST-UHFFFAOYSA-N 0.000 claims description 6
- XDQCDBYXMDOGCG-UHFFFAOYSA-N 2-[[7-methyl-1-(2,4,6-trimethylphenyl)-2,4-dihydropyrido[2,3-d][1,3]oxazin-5-yl]amino]butan-1-ol Chemical compound C1OCC=2C(NC(CO)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C XDQCDBYXMDOGCG-UHFFFAOYSA-N 0.000 claims description 6
- AMQUNQDGMAPPCK-UHFFFAOYSA-N 2-[butyl-[2,5-dimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amino]ethanol Chemical compound C1=C(C)C=2C(N(CCO)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C AMQUNQDGMAPPCK-UHFFFAOYSA-N 0.000 claims description 6
- JCGHMRBJFIIZCB-UHFFFAOYSA-N 2-methyl-n-pentan-2-yl-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1CCC=2C(NC(C)CCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C JCGHMRBJFIIZCB-UHFFFAOYSA-N 0.000 claims description 6
- ZSEJGVQTBLJRCQ-UHFFFAOYSA-N 3,6-dimethyl-4-pentan-3-yloxy-2-(2,4,6-trimethylphenoxy)pyridine Chemical compound CCC(CC)OC1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C ZSEJGVQTBLJRCQ-UHFFFAOYSA-N 0.000 claims description 6
- VIZBSVDBNLAVAW-UHFFFAOYSA-N 3,6-dimethyl-n-pentan-3-yl-2-(2,4,6-trimethylphenoxy)pyridin-4-amine Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C VIZBSVDBNLAVAW-UHFFFAOYSA-N 0.000 claims description 6
- AKFWXFDMKRSYRD-UHFFFAOYSA-N 3-(2,4-dimethoxyphenyl)-n-(2-methoxyethyl)-2,5-dimethyl-n-propylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N(CCOC)CCC)=CC(C)=NC2=C1C1=CC=C(OC)C=C1OC AKFWXFDMKRSYRD-UHFFFAOYSA-N 0.000 claims description 6
- ANNRUWYFVIGKHA-UHFFFAOYSA-N 3-[6-(dimethylamino)-4-methylpyridin-3-yl]-2,5-dimethyl-n,n-dipropylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N(CCC)CCC)=CC(C)=NC2=C1C1=CN=C(N(C)C)C=C1C ANNRUWYFVIGKHA-UHFFFAOYSA-N 0.000 claims description 6
- NSZSAPMQWCARQU-UHFFFAOYSA-N 3-[[3,6-dimethyl-1-(2,4,6-trimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-yl]-[(4-methylphenyl)methyl]amino]propan-1-ol Chemical compound C12=NC(C)=NC(N(CCCO)CC=3C=CC(C)=CC=3)=C2C(C)=NN1C1=C(C)C=C(C)C=C1C NSZSAPMQWCARQU-UHFFFAOYSA-N 0.000 claims description 6
- ZZNOWBFPUVEVCB-UHFFFAOYSA-N 4,7-dimethyl-1-pentan-3-yl-5-(2,4,6-trimethylphenoxy)-2,3-dihydropyrido[3,4-b]pyrazine Chemical compound N1=C(C)C=C2N(C(CC)CC)CCN(C)C2=C1OC1=C(C)C=C(C)C=C1C ZZNOWBFPUVEVCB-UHFFFAOYSA-N 0.000 claims description 6
- CJERNBGBGBNILW-UHFFFAOYSA-N 4,7-dimethyl-1-pentan-3-yl-5-(2,4,6-trimethylphenoxy)-2h-pyrido[3,4-b]pyrazin-3-one Chemical compound N1=C(C)C=C2N(C(CC)CC)CC(=O)N(C)C2=C1OC1=C(C)C=C(C)C=C1C CJERNBGBGBNILW-UHFFFAOYSA-N 0.000 claims description 6
- PUZLSXWSLTZXSJ-UHFFFAOYSA-N 4-[butyl(ethyl)amino]-2,6-dimethyl-8-(2,4,6-trimethylphenyl)-5,6-dihydropyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(C)CC=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C PUZLSXWSLTZXSJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- HEHMAMAKTJHFJM-UHFFFAOYSA-N 5-methyl-n-pentan-3-yl-3-(2,4,6-trimethylphenyl)pyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=NN2C(NC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C HEHMAMAKTJHFJM-UHFFFAOYSA-N 0.000 claims description 6
- YWAODLGBSKCKEC-UHFFFAOYSA-N 6-methyl-1-pentan-3-yl-4-(2,4,6-trimethylphenoxy)-3h-imidazo[4,5-c]pyridin-2-one Chemical compound C=12NC(=O)N(C(CC)CC)C2=CC(C)=NC=1OC1=C(C)C=C(C)C=C1C YWAODLGBSKCKEC-UHFFFAOYSA-N 0.000 claims description 6
- IPPBHNMFESFVGT-UHFFFAOYSA-N 6-methyl-8-pentan-3-yloxy-4-(2,4,6-trimethylphenyl)-2,3-dihydro-1h-pyrido[2,3-b]pyrazine Chemical compound C1CNC=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C IPPBHNMFESFVGT-UHFFFAOYSA-N 0.000 claims description 6
- KGVVSDCYKJUXMV-UHFFFAOYSA-N 7-heptan-4-yl-2,5,6-trimethyl-4-(2,4,6-trimethylphenoxy)pyrrolo[2,3-d]pyrimidine Chemical compound N1=C(C)N=C2N(C(CCC)CCC)C(C)=C(C)C2=C1OC1=C(C)C=C(C)C=C1C KGVVSDCYKJUXMV-UHFFFAOYSA-N 0.000 claims description 6
- MZJBIBIKKQDVQS-UHFFFAOYSA-N 7-methyl-1-pentan-3-yl-5-(2,4,6-trimethylphenoxy)-2,4-dihydropyrido[4,3-d][1,3]oxazine Chemical compound N1=C(C)C=C2N(C(CC)CC)COCC2=C1OC1=C(C)C=C(C)C=C1C MZJBIBIKKQDVQS-UHFFFAOYSA-N 0.000 claims description 6
- QWZOTNGDCPJMOQ-UHFFFAOYSA-N 8-(1-hydroxybutan-2-ylamino)-6-methyl-4-(2,4,6-trimethylphenyl)-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1C(=O)NC=2C(NC(CO)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C QWZOTNGDCPJMOQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 6
- NHNUIXSRWNFVQP-UHFFFAOYSA-N n-ethyl-2,5-dimethyl-n-propyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(C)C=2C(N(CC)CCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C NHNUIXSRWNFVQP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- ZRPGMVFEQOQSGF-UHFFFAOYSA-N propan-2-yl 7-methyl-2-oxo-1-pentan-3-yl-5-(2,4,6-trimethylphenoxy)-3,4-dihydro-1,6-naphthyridine-3-carboxylate Chemical compound N1=C(C)C=C2N(C(CC)CC)C(=O)C(C(=O)OC(C)C)CC2=C1OC1=C(C)C=C(C)C=C1C ZRPGMVFEQOQSGF-UHFFFAOYSA-N 0.000 claims description 6
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims description 6
- QIIZTANZQMETMP-UHFFFAOYSA-N 2-methyl-4-pentan-3-yloxy-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-pyrido[2,3-d]pyrimidine Chemical compound C1CCC=2C(OC(CC)CC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C QIIZTANZQMETMP-UHFFFAOYSA-N 0.000 claims description 5
- SQVZUGHPSMFDBH-UHFFFAOYSA-N 2-methyl-4-pentan-3-yloxy-8-(2,4,6-trimethylphenyl)quinoline Chemical compound C1=CC=C2C(OC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C SQVZUGHPSMFDBH-UHFFFAOYSA-N 0.000 claims description 5
- NOVMRCQAXSODAQ-UHFFFAOYSA-N 3,6-dimethyl-4-pentan-3-yloxy-n-(2,4,6-trimethylphenyl)pyridin-2-amine Chemical compound CCC(CC)OC1=CC(C)=NC(NC=2C(=CC(C)=CC=2C)C)=C1C NOVMRCQAXSODAQ-UHFFFAOYSA-N 0.000 claims description 5
- MUXBHSAZFHTFEJ-UHFFFAOYSA-N 3-(2,4-dimethylphenyl)-2,5-dimethyl-n-pentan-3-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(NC(CC)CC)=CC(C)=NC2=C1C1=CC=C(C)C=C1C MUXBHSAZFHTFEJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- IMWQDIRXGPWJJC-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-(2,4-dimethylphenyl)-2,5-dimethyl-n-propylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C(=CC(C)=CC=3)C)C(C)=NN2C=1N(CCC)CC1CC1 IMWQDIRXGPWJJC-UHFFFAOYSA-N 0.000 claims description 5
- OYVBLBHOUAJPKQ-UHFFFAOYSA-N n-ethyl-3,6-dimethyl-n-propyl-1-(2,4,6-trimethylphenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(C)C=2C(N(CC)CCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C OYVBLBHOUAJPKQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 3
- HNMZXNKERMVFCH-UHFFFAOYSA-N 1,6-dimethyl-8-pentan-3-yloxy-4-(2,4,6-trimethylphenyl)-2,3-dihydropyrido[2,3-b]pyrazine Chemical compound C1CN(C)C=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C HNMZXNKERMVFCH-UHFFFAOYSA-N 0.000 claims description 3
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- SKRMDWHRWISVGC-UHFFFAOYSA-N 8-(4-bromo-2,6-dimethylphenyl)-n-hexan-2-yl-2-methyl-6,7-dihydro-5h-pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1CCC=2C(NC(C)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(Br)C=C1C SKRMDWHRWISVGC-UHFFFAOYSA-N 0.000 claims description 3
- BDNFYALKFBDLBT-UHFFFAOYSA-N 8-(4-chloro-2,6-dimethylphenyl)-2-methyl-4-pentan-3-yloxyquinoline Chemical compound C1=CC=C2C(OC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(Cl)C=C1C BDNFYALKFBDLBT-UHFFFAOYSA-N 0.000 claims description 3
- DGYIKHAPQPDTFS-UHFFFAOYSA-N 8-(4-chloro-2,6-dimethylphenyl)-2-methyl-n-pentan-3-ylquinolin-4-amine Chemical compound C1=CC=C2C(NC(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(Cl)C=C1C DGYIKHAPQPDTFS-UHFFFAOYSA-N 0.000 claims description 3
- QOYOMMYMWCBHDN-UHFFFAOYSA-N 8-(diethylamino)-6-methyl-4-(2,4,6-trimethylphenyl)-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1C(=O)NC=2C(N(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C QOYOMMYMWCBHDN-UHFFFAOYSA-N 0.000 claims description 3
- JXNBEYHSFHNFHX-UHFFFAOYSA-N 8-[butyl(ethyl)amino]-6-methyl-4-(2,4,6-trimethylphenyl)-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1C(=O)NC=2C(N(CC)CCCC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C JXNBEYHSFHNFHX-UHFFFAOYSA-N 0.000 claims description 3
- VCJQTLOUICAEMC-UHFFFAOYSA-N 8-[ethyl(propyl)amino]-6-methyl-4-(2,4,6-trimethylphenyl)-1,3-dihydropyrido[2,3-b]pyrazin-2-one Chemical compound C1C(=O)NC=2C(N(CC)CCC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C VCJQTLOUICAEMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000815 N-oxide group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- IXPROWGEHNVJOY-UHFFFAOYSA-N antalarmin Chemical compound CC1=C(C)C=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C IXPROWGEHNVJOY-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- FHQYJZCJRZHINA-UHFFFAOYSA-N cp-154,526 Chemical compound C1=C(C)C=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C FHQYJZCJRZHINA-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 150000002009 diols Chemical group 0.000 claims description 3
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims description 3
- AKSVHDZPCHMPRP-UHFFFAOYSA-N methyl 2-[5-[[4-(2-chloro-4-methoxyphenyl)-5-methyl-1,3-thiazol-2-yl]-propylamino]indol-1-yl]acetate Chemical compound C=1C=C2N(CC(=O)OC)C=CC2=CC=1N(CCC)C(SC=1C)=NC=1C1=CC=C(OC)C=C1Cl AKSVHDZPCHMPRP-UHFFFAOYSA-N 0.000 claims description 3
- MYFIUHJIEHESCM-UHFFFAOYSA-N methyl 6-methyl-4-(pentan-3-ylamino)-2-(2,4,6-trimethylphenoxy)pyridine-3-carboxylate Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(C)=CC=2C)C)=C1C(=O)OC MYFIUHJIEHESCM-UHFFFAOYSA-N 0.000 claims description 3
- DTAFOWXMJZNNMY-UHFFFAOYSA-N methyl 7-methyl-2-oxo-1-pentan-3-yl-5-(2,4,6-trimethylphenoxy)-3,4-dihydro-1,6-naphthyridine-3-carboxylate Chemical compound N1=C(C)C=C2N(C(CC)CC)C(=O)C(C(=O)OC)CC2=C1OC1=C(C)C=C(C)C=C1C DTAFOWXMJZNNMY-UHFFFAOYSA-N 0.000 claims description 3
- BDWZBIFQIVBVRF-UHFFFAOYSA-N n,n-diethyl-2-methyl-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1CCC=2C(N(CC)CC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C BDWZBIFQIVBVRF-UHFFFAOYSA-N 0.000 claims description 3
- BSSFADQRIVCKIW-UHFFFAOYSA-N n,n-diethyl-2-methyl-8-(2,4,6-trimethylphenyl)quinolin-4-amine Chemical compound C1=CC=C2C(N(CC)CC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C BSSFADQRIVCKIW-UHFFFAOYSA-N 0.000 claims description 3
- AKKMUVJKMSUTQN-UHFFFAOYSA-N n,n-diethyl-5-methyl-1-(2,4,6-trimethylphenyl)-4,4a-dihydro-2h-pyrido[2,3-d][1,3]oxazin-5-amine Chemical compound CCN(CC)C1(C)C=CN=C2C1COCN2C1=C(C)C=C(C)C=C1C AKKMUVJKMSUTQN-UHFFFAOYSA-N 0.000 claims description 3
- HOLJRRMGSSSVEO-UHFFFAOYSA-N n,n-diethyl-6-methyl-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(SC)C=2C(N(CC)CC)=NC(C)=NC=2N1C1=C(Cl)C=C(Cl)C=C1Cl HOLJRRMGSSSVEO-UHFFFAOYSA-N 0.000 claims description 3
- VOMVCTBIQJPYAY-UHFFFAOYSA-N n,n-diethyl-6-methyl-4-(2,4,6-trimethylphenyl)-2,3-dihydro-1h-pyrido[2,3-b]pyrazin-8-amine Chemical compound C1CNC=2C(N(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C VOMVCTBIQJPYAY-UHFFFAOYSA-N 0.000 claims description 3
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- NHMUETZDQWNYMF-UHFFFAOYSA-N n-(6-chloroisoquinolin-5-yl)-4-(2-chloro-4-methoxyphenyl)-5-methyl-n-propyl-1,3-thiazol-2-amine Chemical compound ClC=1C=CC2=CN=CC=C2C=1N(CCC)C(SC=1C)=NC=1C1=CC=C(OC)C=C1Cl NHMUETZDQWNYMF-UHFFFAOYSA-N 0.000 claims description 3
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- OGEPBWVHDWHFGF-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-[6-(dimethylamino)-4-methylpyridin-3-yl]-2,5-dimethyl-n-propylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C(=CC(=NC=3)N(C)C)C)C(C)=NN2C=1N(CCC)CC1CC1 OGEPBWVHDWHFGF-UHFFFAOYSA-N 0.000 claims description 3
- SJPOFRDVWLFHSD-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-[6-(dimethylamino)-4-methylpyridin-3-yl]-n-ethyl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C=1C(C)=NC2=C(C=3C(=CC(=NC=3)N(C)C)C)C(C)=NN2C=1N(CC)CC1CC1 SJPOFRDVWLFHSD-UHFFFAOYSA-N 0.000 claims description 3
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- WWHVAGVLUHFAGU-UHFFFAOYSA-N n-butyl-7-(2,4-dimethylphenyl)-n-ethyl-2,5-dimethylpyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=C(C)C=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=CC=C(C)C=C1C WWHVAGVLUHFAGU-UHFFFAOYSA-N 0.000 claims description 3
- IEVPAOCJKVVVJQ-UHFFFAOYSA-N n-butyl-n-ethyl-2,5-dimethyl-7-(2,4,6-trimethylphenyl)-5,6-dihydropyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1C(C)C=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C IEVPAOCJKVVVJQ-UHFFFAOYSA-N 0.000 claims description 3
- YLBFOSKJJOYRAY-UHFFFAOYSA-N n-butyl-n-ethyl-2-methyl-8-(2,4,6-trimethylphenyl)quinolin-4-amine Chemical compound C1=CC=C2C(N(CC)CCCC)=CC(C)=NC2=C1C1=C(C)C=C(C)C=C1C YLBFOSKJJOYRAY-UHFFFAOYSA-N 0.000 claims description 3
- MDELHEVEADGDQT-UHFFFAOYSA-N n-butyl-n-ethyl-6-methoxy-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(SC)C=2C(N(CC)CCCC)=NC(OC)=NC=2N1C1=C(Cl)C=C(Cl)C=C1Cl MDELHEVEADGDQT-UHFFFAOYSA-N 0.000 claims description 3
- HEMGDVZJLKPZNT-UHFFFAOYSA-N n-butyl-n-ethyl-6-methyl-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(SC)C=2C(N(CC)CCCC)=NC(C)=NC=2N1C1=C(Cl)C=C(Cl)C=C1Cl HEMGDVZJLKPZNT-UHFFFAOYSA-N 0.000 claims description 3
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- GMPYWTLKGAWMSS-UHFFFAOYSA-N n-butyl-n-ethyl-6-methyl-4-(2,4,6-trimethylphenyl)-1,2,4,7-tetrahydropyrido[2,3-d][1,3]oxazin-8-amine Chemical compound CCCCN(CC)N1CC(C)=CC2=C1NCOC2C1=C(C)C=C(C)C=C1C GMPYWTLKGAWMSS-UHFFFAOYSA-N 0.000 claims description 3
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- JPNFMNRDEZPDJH-UHFFFAOYSA-N phenanthrene-2-carbonitrile Chemical compound C1=CC=C2C3=CC=C(C#N)C=C3C=CC2=C1 JPNFMNRDEZPDJH-UHFFFAOYSA-N 0.000 claims description 3
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- GATYVUUKXLTIJT-UHFFFAOYSA-N 2-(4-chloro-2,6-dimethylphenoxy)-3,6-dimethyl-n-pentan-3-ylpyridin-4-amine Chemical compound CCC(CC)NC1=CC(C)=NC(OC=2C(=CC(Cl)=CC=2C)C)=C1C GATYVUUKXLTIJT-UHFFFAOYSA-N 0.000 claims description 2
- BNKGKWTYNSBHDH-UHFFFAOYSA-N 2-[[6-methyl-4-(2,4,6-trimethylphenyl)-2,3-dihydro-1h-pyrido[2,3-b]pyrazin-8-yl]oxy]butan-1-ol Chemical compound C1CNC=2C(OC(CO)CC)=CC(C)=NC=2N1C1=C(C)C=C(C)C=C1C BNKGKWTYNSBHDH-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- SJLQJFXGFZUSOI-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-n-(2-ethoxynaphthalen-1-yl)-5-methyl-n-propyl-1,3-thiazol-2-amine Chemical compound CCOC=1C=CC2=CC=CC=C2C=1N(CCC)C(SC=1C)=NC=1C1=CC=C(OC)C=C1Cl SJLQJFXGFZUSOI-UHFFFAOYSA-N 0.000 claims description 2
- CRKVOYZFPHXADQ-UHFFFAOYSA-N 5-methyl-3-phenyl-7-phenylmethoxypyrazolo[1,5-a]pyrimidine Chemical compound N12N=CC(C=3C=CC=CC=3)=C2N=C(C)C=C1OCC1=CC=CC=C1 CRKVOYZFPHXADQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 229910003827 NRaRb Inorganic materials 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- ZECSJWNWZNAGGW-UHFFFAOYSA-N n,2,5-trimethyl-3-phenylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(NC)=CC(C)=NC2=C1C1=CC=CC=C1 ZECSJWNWZNAGGW-UHFFFAOYSA-N 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 354
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 183
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 16
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 13
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 8
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 7
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 6
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 101100509371 Arabidopsis thaliana CHR11 gene Proteins 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000006375 C2-C10 alkynyl group Chemical group 0.000 claims 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 2
- HJYVOLRRIABQTI-UHFFFAOYSA-N 1-(4-chloro-2,6-dimethylphenyl)-7-methyl-5-pentan-3-yloxy-2h-pyrido[2,3-d][1,3]oxazin-4-one Chemical compound C1OC(=O)C=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(Cl)C=C1C HJYVOLRRIABQTI-UHFFFAOYSA-N 0.000 claims 2
- HNJCZHSFAURGSI-UHFFFAOYSA-N 2-[butyl-[6-methyl-3-methylsulfanyl-1-(2,4,6-trichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]ethanol Chemical compound N1=C(SC)C=2C(N(CCO)CCCC)=NC(C)=NC=2N1C1=C(Cl)C=C(Cl)C=C1Cl HNJCZHSFAURGSI-UHFFFAOYSA-N 0.000 claims 2
- QPAIYACHPNHYGO-UHFFFAOYSA-N 2-methyl-n-pentan-3-yl-8-(2,4,6-trimethylphenyl)-6,7-dihydro-5h-pyrido[2,3-d]pyrimidin-4-amine Chemical compound C1CCC=2C(NC(CC)CC)=NC(C)=NC=2N1C1=C(C)C=C(C)C=C1C QPAIYACHPNHYGO-UHFFFAOYSA-N 0.000 claims 2
- DOPVGJROKFQOTD-UHFFFAOYSA-N 3-(4-chlorophenyl)-2,5-dimethyl-n,n-dipropylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CC1=NN2C(N(CCC)CCC)=CC(C)=NC2=C1C1=CC=C(Cl)C=C1 DOPVGJROKFQOTD-UHFFFAOYSA-N 0.000 claims 2
- RMJGTILTBHQWOG-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-(2-methoxy-1-naphthalen-2-ylethyl)-5-methyl-n-propyl-1,3-thiazol-2-amine Chemical compound C=1C=C2C=CC=CC2=CC=1C(COC)N(CCC)C(SC=1C)=NC=1C1=CC=C(Cl)C=C1Cl RMJGTILTBHQWOG-UHFFFAOYSA-N 0.000 claims 2
- OEJUUBKXNPEFMQ-UHFFFAOYSA-N 4-(4-chloro-2,6-dimethylphenyl)-6-methyl-8-pentan-3-yloxy-2,3-dihydro-1h-pyrido[2,3-b]pyrazine Chemical compound C1CNC=2C(OC(CC)CC)=CC(C)=NC=2N1C1=C(C)C=C(Cl)C=C1C OEJUUBKXNPEFMQ-UHFFFAOYSA-N 0.000 claims 2
- GFNFPFIKVZCKPS-UHFFFAOYSA-N 6-bromo-5-(bromomethyl)-n-pentan-3-yl-3-(2,4,6-trimethylphenyl)triazolo[4,5-b]pyridin-7-amine Chemical compound N1=NC=2C(NC(CC)CC)=C(Br)C(CBr)=NC=2N1C1=C(C)C=C(C)C=C1C GFNFPFIKVZCKPS-UHFFFAOYSA-N 0.000 claims 2
- UZNIGLOKMZYASZ-UHFFFAOYSA-N 6-methyl-3-methylsulfanyl-n,n-dipropyl-1-(2,4,6-trichlorophenyl)pyrazolo[3,4-d]pyrimidin-4-amine Chemical compound N1=C(SC)C=2C(N(CCC)CCC)=NC(C)=NC=2N1C1=C(Cl)C=C(Cl)C=C1Cl UZNIGLOKMZYASZ-UHFFFAOYSA-N 0.000 claims 2
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Landscapes
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| US6867300B2 (en) | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| DE60225127T2 (de) | 2001-04-30 | 2009-02-19 | Glaxo Group Ltd., Greenford | Kondensierte pyrimidine als antagonisten des corticotropin releasing factor (crf) |
| JP2005532268A (ja) * | 2002-02-22 | 2005-10-27 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | 置換されたピリミジノンおよびピリミジンチオン |
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| DE60318188T2 (de) * | 2002-03-26 | 2008-12-11 | Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield | Glucocorticoid-mimetika, deren herstellung, pharmazeutische zusammensetzungen und verwendung |
| BR0309551A (pt) | 2002-04-26 | 2005-02-09 | Upjohn Co | Derivados substituìdos de pirazina |
| WO2003101949A2 (en) | 2002-05-29 | 2003-12-11 | 3M Innovative Properties Company | Process for imidazo[4,5-c]pyridin-4-amines |
| EP1521733B1 (en) * | 2002-07-08 | 2014-08-20 | Pfizer Products Inc. | Modulators of the glucocorticoid receptor |
| US20040116444A1 (en) * | 2002-09-12 | 2004-06-17 | Corbett Jeffrey W. | Substituted 1,4-pyrazine derivatives |
| AR041470A1 (es) | 2002-10-17 | 2005-05-18 | Upjohn Co | Compuestos de pirrolo (1,2 - b) piridazina y sus usos |
| CA2504751C (en) * | 2002-11-05 | 2013-02-05 | Corcept Therapeutics, Inc. | Methods for treating gastroesophageal reflux disease |
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| CA2499133A1 (en) * | 2002-11-21 | 2004-06-03 | Pharmacia & Upjohn Company Llc | Pyrazine compounds as crf modulators |
| HRP20050696B1 (en) | 2003-01-14 | 2008-10-31 | Arena Pharmaceuticals Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| JP2006524223A (ja) * | 2003-04-23 | 2006-10-26 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | Ｃｒｆアンタゴニストとしての置換されたピリミジノンおよびピリミジンチオン |
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| BRPI0409505A (pt) | 2003-05-09 | 2006-04-18 | Pharmacia & Upjohn Co Llc | compostos como antagonistas do receptor crf1 |
| EP1625115A1 (en) | 2003-05-09 | 2006-02-15 | Pharmacia & Upjohn Company LLC | Substituted pyrimidine derivatives |
| US7132426B2 (en) * | 2003-07-14 | 2006-11-07 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| AU2004266641A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| EP1658076B1 (en) | 2003-08-27 | 2013-03-06 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| US20050054665A1 (en) | 2003-09-05 | 2005-03-10 | 3M Innovative Properties Company | Treatment for CD5+ B cell lymphoma |
| UY28526A1 (es) * | 2003-09-24 | 2005-04-29 | Boehringer Ingelheim Pharma | Miméticos de glucocorticoides, métodos de preparación composiciones farmacéuticas y usos de los mismos |
| ES2544477T3 (es) | 2003-10-03 | 2015-08-31 | 3M Innovative Properties Company | Imidazoquinolinas sustituidas con alcoxi |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| JP2007511535A (ja) | 2003-11-14 | 2007-05-10 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミン置換イミダゾ環化合物 |
| US7897767B2 (en) | 2003-11-14 | 2011-03-01 | 3M Innovative Properties Company | Oxime substituted imidazoquinolines |
| RU2409576C2 (ru) | 2003-11-25 | 2011-01-20 | 3М Инновейтив Пропертиз Компани | Системы, содержащие имидазольное кольцо с заместителями, и способы их получения |
| AU2004309168B2 (en) * | 2003-12-22 | 2009-04-23 | Neurocrine Biosciences Inc | CRF receptor antagonists and methods relating thereto |
| US20070293511A1 (en) * | 2003-12-22 | 2007-12-20 | Sb Pharmco Puerto Rico Inc. And Neurocrine Biosciences, Inc., A Corporation | Crf Receptor Antagonists and Methods |
| WO2005066170A1 (en) | 2003-12-29 | 2005-07-21 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
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| EP1730143A2 (en) | 2004-03-24 | 2006-12-13 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
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| WO2006038923A2 (en) | 2004-06-18 | 2006-04-13 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US7504521B2 (en) * | 2004-08-05 | 2009-03-17 | Bristol-Myers Squibb Co. | Methods for the preparation of pyrrolotriazine compounds |
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2000
- 2000-10-23 IL IL13919700A patent/IL139197A0/xx unknown
- 2000-10-23 CO CO00080519A patent/CO5271670A1/es not_active Application Discontinuation
- 2000-10-24 AU AU66695/00A patent/AU776724B2/en not_active Ceased
- 2000-10-26 ZA ZA200006008A patent/ZA200006008B/xx unknown
- 2000-10-26 EP EP00309441A patent/EP1097709A3/en not_active Withdrawn
- 2000-10-26 US US09/696,822 patent/US6589947B1/en not_active Expired - Fee Related
- 2000-10-27 CA CA002325069A patent/CA2325069A1/en not_active Abandoned
- 2000-10-27 KR KR1020000063351A patent/KR20010051274A/ko not_active Ceased
- 2000-10-27 HU HU0004194A patent/HUP0004194A3/hu unknown
- 2000-10-27 PE PE2000001159A patent/PE20010807A1/es not_active Application Discontinuation
- 2000-10-27 NZ NZ507825A patent/NZ507825A/en unknown
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2003
- 2003-04-15 US US10/413,879 patent/US6777404B2/en not_active Expired - Fee Related
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| IL139197A0 (en) | 2001-11-25 |
| HUP0004194A3 (en) | 2002-03-28 |
| CO5271670A1 (es) | 2003-04-30 |
| ZA200006008B (en) | 2002-04-26 |
| HUP0004194A2 (hu) | 2001-12-28 |
| NZ507825A (en) | 2004-11-26 |
| EP1097709A3 (en) | 2005-12-21 |
| KR20010051274A (ko) | 2001-06-25 |
| US6589947B1 (en) | 2003-07-08 |
| AU776724B2 (en) | 2004-09-16 |
| AU6669500A (en) | 2001-05-03 |
| US20030199527A1 (en) | 2003-10-23 |
| EP1097709A2 (en) | 2001-05-09 |
| US6777404B2 (en) | 2004-08-17 |
| HU0004194D0 (enExample) | 2001-01-29 |
| PE20010807A1 (es) | 2001-08-03 |
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| FZDE | Discontinued |