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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| US16234099P | 1999-10-29 | 1999-10-29 | |
| US60/162,340 | 1999-10-29 |
Publications (1)
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| CA2325069A1 true CA2325069A1 (en) | 2001-04-29 |
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| CA002325069A Abandoned CA2325069A1 (en) | 1999-10-29 | 2000-10-27 | Use of corticotropin releasing factor antagonists and related compositions |
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| US (2) | US6589947B1 (en:Method) |
| EP (1) | EP1097709A3 (en:Method) |
| KR (1) | KR20010051274A (en:Method) |
| AU (1) | AU776724B2 (en:Method) |
| CA (1) | CA2325069A1 (en:Method) |
| CO (1) | CO5271670A1 (en:Method) |
| HU (1) | HUP0004194A3 (en:Method) |
| IL (1) | IL139197A0 (en:Method) |
| NZ (1) | NZ507825A (en:Method) |
| PE (1) | PE20010807A1 (en:Method) |
| ZA (1) | ZA200006008B (en:Method) |
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| EP1449532A1 (en) * | 1999-08-27 | 2004-08-25 | Pfizer Products Inc. | Compound [2-(4-chloro-2,6-dimethyl-phenoxy)- 3,6-dimethyl-pyridin-4-yl]- (1-ethyl-propyl)- amine and use as CRF antagonist |
| EA200200422A1 (ru) * | 1999-09-30 | 2002-10-31 | Ньюроджен Корпорейшн | НЕКОТОРЫЕ АЛКИЛЕНДИАМИНОЗАМЕЩЕННЫЕ ПИРАЗОЛО[1,5-а]-1,5-ПИРИМИДИНЫ И ПИРАЗОЛО[1,5-а]-1,3,5-ТРИАЗИНЫ |
| CO5271670A1 (es) * | 1999-10-29 | 2003-04-30 | Pfizer Prod Inc | Antagonistas del factor de liberacion de corticitropina y composiciones relacionadas |
| EP1149583A3 (en) * | 2000-04-13 | 2001-11-14 | Pfizer Products Inc. | Combinations of corticotropin releasing factor antagonists and growth hormone secretagogues |
| US6867300B2 (en) | 2000-11-17 | 2005-03-15 | Bristol-Myers Squibb Company | Methods for the preparation of pyrrolotriazine compounds useful as kinase inhibitors |
| CA2446514A1 (en) * | 2001-04-30 | 2002-11-07 | Glaxo Group Limited | Fused pyrimidines as antagonists of the corticotropin releasing factor (crf) |
| WO2003072107A1 (en) * | 2002-02-22 | 2003-09-04 | Pharmacia & Upjohn Company | Substituted pyrimidinones and pyrimidinthiones |
| MXPA04008790A (es) * | 2002-03-13 | 2004-11-26 | Pharmacia & Upjohn Co Llc | Derivados pirazolo(1,5,a)piridina como moduladores neurotransmisores. |
| DE60318188T2 (de) * | 2002-03-26 | 2008-12-11 | Boehringer Ingelheim Pharmaceuticals, Inc., Ridgefield | Glucocorticoid-mimetika, deren herstellung, pharmazeutische zusammensetzungen und verwendung |
| AU2003223475A1 (en) | 2002-04-26 | 2003-11-10 | Pharmacia And Upjohn Company | Substituted pyrazine derivatives |
| JP2005531599A (ja) | 2002-05-29 | 2005-10-20 | スリーエム イノベイティブ プロパティズ カンパニー | イミダゾ［４，５−ｃ］ピリジン−４−アミンのための方法 |
| DK1521733T3 (da) * | 2002-07-08 | 2014-10-13 | Pfizer Prod Inc | Modulatorer af glucocorticoid receptoren |
| WO2004024719A1 (en) * | 2002-09-12 | 2004-03-25 | Pharmacia & Upjohn Company Llc | 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 |
| US20060052354A1 (en) * | 2002-11-05 | 2006-03-09 | Corcept Therapeutics, Inc. | Methods for treating migraine |
| JP2006508951A (ja) * | 2002-11-05 | 2006-03-16 | コーセプト セラピューティクス， インコーポレイテッド | 片頭痛を処置するための方法 |
| WO2004046136A1 (en) * | 2002-11-21 | 2004-06-03 | Pharmacia & Upjohn Company Llc | Pyrazine compounds as crf modulators |
| ATE374766T1 (de) | 2003-01-14 | 2007-10-15 | Arena Pharm Inc | 1,2,3-trisubstituierte aryl- und heteroarylderivate als modulatoren des metabolismus zur vorbeugung und behandlung von metabolismus-bedingten krankheiten wie diabetes oder hyperglykämie |
| BRPI0409649A (pt) * | 2003-04-23 | 2006-04-25 | Pharmacia & Upjohn Co Llc | pirimidinonas e pirimidinotionas substituìdas como antagonistas de crf |
| CA2523072A1 (en) * | 2003-05-07 | 2004-11-18 | Pharmacia & Upjohn Company Llc | Pyrrolo (1,2-b) pyridazine compounds and their use as crf-1 receptor antagonists |
| JP2006525989A (ja) * | 2003-05-09 | 2006-11-16 | 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 | Ｃｎｓ障害を治療するためのｃｒｆ１受容体アンタゴニストとしてのピラジノン |
| CA2524352A1 (en) | 2003-05-09 | 2004-11-18 | Pharmacia & Upjohn Company Llc | Substituted pyrimidine derivatives |
| WO2004099201A1 (en) | 2003-05-09 | 2004-11-18 | Pharmacia & Upjohn Company Llc | Compounds as crf1 receptor antagonists |
| NZ544200A (en) | 2003-07-14 | 2009-07-31 | Arena Pharm Inc | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| BRPI0412902A (pt) | 2003-08-12 | 2006-09-26 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por oxima |
| CA2536136C (en) | 2003-08-27 | 2012-10-30 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| AU2004270201A1 (en) | 2003-09-05 | 2005-03-17 | 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 |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| CN1897948A (zh) | 2003-10-03 | 2007-01-17 | 3M创新有限公司 | 烷氧基取代的咪唑并喹啉 |
| JP2007511527A (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 | オキシム置換イミダゾ環化合物 |
| EP1682544A4 (en) | 2003-11-14 | 2009-05-06 | 3M Innovative Properties Co | HYDROXYLAMINE SUBSTITUTED IMIDAZO RING COMPOUNDS |
| RU2409576C2 (ru) | 2003-11-25 | 2011-01-20 | 3М Инновейтив Пропертиз Компани | Системы, содержащие имидазольное кольцо с заместителями, и способы их получения |
| CN1938309B (zh) * | 2003-12-22 | 2011-11-09 | 史密斯克莱.比奇曼（科克）有限公司 | Crf受体拮抗剂及其相关方法 |
| JP2007515474A (ja) * | 2003-12-22 | 2007-06-14 | エスビー・ファルムコ・プエルト・リコ・インコーポレイテッド | Ｃｒｆ受容体アンタゴニストおよびそれらに関連する方法 |
| US8802853B2 (en) | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| US8735421B2 (en) | 2003-12-30 | 2014-05-27 | 3M Innovative Properties Company | Imidazoquinolinyl sulfonamides |
| US8697873B2 (en) | 2004-03-24 | 2014-04-15 | 3M Innovative Properties Company | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| WO2005123080A2 (en) | 2004-06-15 | 2005-12-29 | 3M Innovative Properties Company | Nitrogen-containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
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- 2000-10-23 IL IL13919700A patent/IL139197A0/xx unknown
- 2000-10-24 AU AU66695/00A patent/AU776724B2/en not_active Ceased
- 2000-10-26 EP EP00309441A patent/EP1097709A3/en not_active Withdrawn
- 2000-10-26 ZA ZA200006008A patent/ZA200006008B/xx unknown
- 2000-10-26 US US09/696,822 patent/US6589947B1/en not_active Expired - Fee Related
- 2000-10-27 PE PE2000001159A patent/PE20010807A1/es not_active Application Discontinuation
- 2000-10-27 NZ NZ507825A patent/NZ507825A/en unknown
- 2000-10-27 CA CA002325069A patent/CA2325069A1/en not_active Abandoned
- 2000-10-27 HU HU0004194A patent/HUP0004194A3/hu unknown
- 2000-10-27 KR KR1020000063351A patent/KR20010051274A/ko not_active Ceased
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2003
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| EP1097709A2 (en) | 2001-05-09 |
| NZ507825A (en) | 2004-11-26 |
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| HU0004194D0 (en:Method) | 2001-01-29 |
| AU6669500A (en) | 2001-05-03 |
| US6777404B2 (en) | 2004-08-17 |
| IL139197A0 (en) | 2001-11-25 |
| HUP0004194A2 (hu) | 2001-12-28 |
| CO5271670A1 (es) | 2003-04-30 |
| PE20010807A1 (es) | 2001-08-03 |
| EP1097709A3 (en) | 2005-12-21 |
| US20030199527A1 (en) | 2003-10-23 |
| ZA200006008B (en) | 2002-04-26 |
| US6589947B1 (en) | 2003-07-08 |
| AU776724B2 (en) | 2004-09-16 |
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