MX2007016541A - Compuestos quimicos. - Google Patents
Compuestos quimicos.Info
- Publication number
- MX2007016541A MX2007016541A MX2007016541A MX2007016541A MX2007016541A MX 2007016541 A MX2007016541 A MX 2007016541A MX 2007016541 A MX2007016541 A MX 2007016541A MX 2007016541 A MX2007016541 A MX 2007016541A MX 2007016541 A MX2007016541 A MX 2007016541A
- Authority
- MX
- Mexico
- Prior art keywords
- indole
- carboxamide
- piperidinyl
- methyl
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 405
- 101710205525 Inhibitor of nuclear factor kappa-B kinase subunit beta Proteins 0.000 claims abstract description 56
- 102100021854 Inhibitor of nuclear factor kappa-B kinase subunit beta Human genes 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 230000000694 effects Effects 0.000 claims abstract description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 208000035475 disorder Diseases 0.000 claims abstract description 21
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 14
- 208000006673 asthma Diseases 0.000 claims abstract description 12
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 476
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 428
- -1 2,3-dihydro-1H-indenyl Chemical group 0.000 claims description 410
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 323
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 308
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 97
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 71
- 125000001072 heteroaryl group Chemical group 0.000 claims description 67
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 62
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 37
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 36
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 34
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 33
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 23
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 23
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 18
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
- 125000004450 alkenylene group Chemical group 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
- 125000006308 propyl amino group Chemical group 0.000 claims description 9
- 208000030507 AIDS Diseases 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 239000000443 aerosol Substances 0.000 claims description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 229910052770 Uranium Inorganic materials 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- 125000006311 cyclobutyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 230000002757 inflammatory effect Effects 0.000 claims description 6
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 5
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 claims description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 206010006895 Cachexia Diseases 0.000 claims description 4
- 208000017604 Hodgkin disease Diseases 0.000 claims description 4
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 241000009298 Trigla lyra Species 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 4
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 4
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 230000017423 tissue regeneration Effects 0.000 claims description 4
- 230000001052 transient effect Effects 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- VBHKZSRKHRGZSY-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-(piperazin-1-ylmethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CCNCC4)C=CC=3)C=C12 VBHKZSRKHRGZSY-UHFFFAOYSA-N 0.000 claims description 2
- QBPQGIFEWFUALZ-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-[1-(2-methylpropylamino)ethyl]phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(C=CC=3)C(C)NCC(C)C)C=C12 QBPQGIFEWFUALZ-UHFFFAOYSA-N 0.000 claims description 2
- REAJCPZFWYARQR-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[4-(4-methyl-2-oxopiperazin-1-yl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(=CC=3)N3C(CN(C)CC3)=O)C=C12 REAJCPZFWYARQR-UHFFFAOYSA-N 0.000 claims description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010003591 Ataxia Diseases 0.000 claims description 2
- 206010003645 Atopy Diseases 0.000 claims description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 2
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 2
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 230000003902 lesion Effects 0.000 claims description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GCMYIIBSCXYCKF-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-(6-morpholin-4-ylpyridazin-3-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3N=NC(=CC=3)N3CCOCC3)C=C12 GCMYIIBSCXYCKF-UHFFFAOYSA-N 0.000 claims 1
- UHEOPOYPPPOVIO-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[2-(morpholin-4-ylmethyl)-1,3-thiazol-4-yl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3N=C(CN4CCOCC4)SC=3)C=C12 UHEOPOYPPPOVIO-UHFFFAOYSA-N 0.000 claims 1
- VNHPASAJUZSEHH-UHFFFAOYSA-N 3-(1-ethylsulfonylpiperidin-4-yl)-5-[3-(pyrrolidin-1-ylmethyl)phenyl]-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN4CCCC4)C=CC=3)C=C12 VNHPASAJUZSEHH-UHFFFAOYSA-N 0.000 claims 1
- SIJJRPGHOJKDOF-UHFFFAOYSA-N 3-[(cyclopropylamino)methyl]phenol Chemical compound OC1=CC=CC(CNC2CC2)=C1 SIJJRPGHOJKDOF-UHFFFAOYSA-N 0.000 claims 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims 1
- VJGQGQQMSIQTEN-UHFFFAOYSA-N 5-(4-acetamidophenyl)-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(NC(C)=O)=CC=3)C=C12 VJGQGQQMSIQTEN-UHFFFAOYSA-N 0.000 claims 1
- AKDFXUYHCLOFKJ-UHFFFAOYSA-N 5-[3,4-dimethoxy-5-(pyrrolidin-1-ylmethyl)phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(OC)C(OC)=C(CN4CCCC4)C=3)C=C12 AKDFXUYHCLOFKJ-UHFFFAOYSA-N 0.000 claims 1
- AWCRDOVNLSIRBI-UHFFFAOYSA-N 5-[3-(aminomethyl)phenyl]-3-(1-ethylsulfonylpiperidin-4-yl)-1h-indole-7-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=CNC2=C(C(N)=O)C=C(C=3C=C(CN)C=CC=3)C=C12 AWCRDOVNLSIRBI-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- 101100456896 Drosophila melanogaster metl gene Proteins 0.000 claims 1
- 239000006002 Pepper Substances 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 claims 1
- 239000006063 cullet Substances 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 122
- 239000003112 inhibitor Substances 0.000 abstract description 23
- 238000011282 treatment Methods 0.000 abstract description 17
- 230000002401 inhibitory effect Effects 0.000 abstract description 11
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 217
- 238000001819 mass spectrum Methods 0.000 description 185
- 239000000243 solution Substances 0.000 description 182
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 155
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 108
- 229910001868 water Inorganic materials 0.000 description 106
- 238000006243 chemical reaction Methods 0.000 description 101
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 239000000203 mixture Substances 0.000 description 88
- 239000011541 reaction mixture Substances 0.000 description 88
- 238000002953 preparative HPLC Methods 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 67
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 229960000583 acetic acid Drugs 0.000 description 50
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 48
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 48
- 239000002253 acid Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 41
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 39
- 239000011734 sodium Substances 0.000 description 38
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- 229910052708 sodium Inorganic materials 0.000 description 37
- 229940083542 sodium Drugs 0.000 description 37
- 239000006196 drop Substances 0.000 description 33
- 239000012044 organic layer Substances 0.000 description 32
- 239000012043 crude product Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 29
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
- 125000004429 atom Chemical group 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 27
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69525605P | 2005-06-30 | 2005-06-30 | |
| PCT/US2006/025402 WO2007005534A2 (en) | 2005-06-30 | 2006-06-28 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007016541A true MX2007016541A (es) | 2008-03-07 |
Family
ID=37605008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007016541A MX2007016541A (es) | 2005-06-30 | 2006-06-28 | Compuestos quimicos. |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1896014A4 (ru) |
| JP (1) | JP5059756B2 (ru) |
| KR (1) | KR20080021077A (ru) |
| CN (1) | CN101247804B (ru) |
| AR (1) | AR055343A1 (ru) |
| AU (1) | AU2006266028B2 (ru) |
| BR (1) | BRPI0611674A2 (ru) |
| CA (1) | CA2613068A1 (ru) |
| EA (1) | EA014083B1 (ru) |
| IL (1) | IL187786A0 (ru) |
| MA (1) | MA29566B1 (ru) |
| MX (1) | MX2007016541A (ru) |
| NO (1) | NO20080457L (ru) |
| NZ (1) | NZ563687A (ru) |
| PE (1) | PE20070173A1 (ru) |
| TW (1) | TWI380973B (ru) |
| UA (1) | UA99699C2 (ru) |
| WO (1) | WO2007005534A2 (ru) |
| ZA (1) | ZA200709948B (ru) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0315950D0 (en) | 2003-06-11 | 2003-08-13 | Xention Discovery Ltd | Compounds |
| PE20060748A1 (es) * | 2004-09-21 | 2006-10-01 | Smithkline Beecham Corp | Derivados de indolcarboxamida como inhibidores de quinasa ikk2 |
| GB0525164D0 (en) * | 2005-12-09 | 2006-01-18 | Xention Discovery Ltd | Compounds |
| WO2007076286A2 (en) * | 2005-12-16 | 2007-07-05 | Smithkline Beecham Corporation | Chemical compounds |
| PE20081889A1 (es) | 2007-03-23 | 2009-03-05 | Smithkline Beecham Corp | Indol carboxamidas como inhibidores de ikk2 |
| JP5557849B2 (ja) * | 2008-12-19 | 2014-07-23 | ブリストル−マイヤーズ スクイブ カンパニー | カルバゾールおよびカルボリンキナーゼ阻害剤 |
| US8354539B2 (en) | 2009-03-10 | 2013-01-15 | Glaxo Group Limited | Indole derivatives as IKK2 inhibitors |
| US9567339B2 (en) * | 2013-06-26 | 2017-02-14 | Abbvie Inc. | Primary carboxamides as BTK inhibitors |
| LT3209656T (lt) * | 2014-10-24 | 2020-07-27 | Bristol-Myers Squibb Company | Indolo karboksamidai - junginiai, naudingi kaip kinazės inhibitoriai |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20000065A2 (en) * | 1997-08-06 | 2001-04-30 | Lilly Co Eli | 2-acylaminopropanamines as tachykinin receptor antagonists |
| DE19807993A1 (de) | 1998-02-26 | 1999-09-02 | Bayer Ag | Verwendung von ß-Carbolinderivaten zur Bekämpfung von TNF-alpha-abhängigen Krankheiten |
| DE50010931D1 (de) | 1999-06-23 | 2005-09-15 | Aventis Pharma Gmbh | Substituierte benzimidazole |
| DE19928424A1 (de) | 1999-06-23 | 2000-12-28 | Aventis Pharma Gmbh | Substituierte Benzimidazole |
| DE19951360A1 (de) | 1999-10-26 | 2001-05-03 | Aventis Pharma Gmbh | Substituierte Indole |
| GB0003154D0 (en) | 2000-02-12 | 2000-04-05 | Astrazeneca Uk Ltd | Novel compounds |
| EP1209158A1 (en) | 2000-11-18 | 2002-05-29 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines |
| EP1268477B1 (en) | 2000-03-15 | 2010-04-21 | Sanofi-Aventis Deutschland GmbH | Substituted beta-carbolines with ikb-kinase inhibiting activity |
| EP1134221A1 (en) | 2000-03-15 | 2001-09-19 | Aventis Pharma Deutschland GmbH | Substituted beta-carbolines as lkB kinase inhibitors |
| JP2001278886A (ja) * | 2000-03-28 | 2001-10-10 | Dai Ichi Seiyaku Co Ltd | ベンゾオキサジン誘導体及びこれを含有する医薬 |
| US6414013B1 (en) | 2000-06-19 | 2002-07-02 | Pharmacia & Upjohn S.P.A. | Thiophene compounds, process for preparing the same, and pharmaceutical compositions containing the same background of the invention |
| JP4272338B2 (ja) | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
| US6869956B2 (en) | 2000-10-03 | 2005-03-22 | Bristol-Myers Squibb Company | Methods of treating inflammatory and immune diseases using inhibitors of IκB kinase (IKK) |
| ATE319713T1 (de) | 2000-10-03 | 2006-03-15 | Bristol Myers Squibb Co | Amino- substituierte tetracyclische verbindungen die als entzündungshemmende mittel nützlich sind, und diese enthaltende arzneimittel. |
| AU2002211662A1 (en) | 2000-10-12 | 2002-04-22 | Smith Kline Beecham Corporation | Nf-kappab inhibitors |
| JP2004523476A (ja) | 2000-10-12 | 2004-08-05 | スミスクライン・ビーチャム・コーポレイション | NF−κB阻害剤 |
| MXPA03003599A (es) | 2000-10-26 | 2003-08-01 | Tularik Inc | Agentes antiinflamatorios. |
| JP2002193938A (ja) | 2000-12-01 | 2002-07-10 | Bayer Ag | 4−アリールピリジン誘導体 |
| US7122544B2 (en) | 2000-12-06 | 2006-10-17 | Signal Pharmaceuticals, Llc | Anilinopyrimidine derivatives as IKK inhibitors and compositions and methods related thereto |
| WO2002060386A2 (en) | 2001-02-01 | 2002-08-08 | Bristol-Myers Squibb Company | METHODS OF TREATING INFLAMMATORY AND IMMUNE DISEASES USING INHIBITORS OF IλB KINASE (IKK) |
| US20030045515A1 (en) | 2001-05-24 | 2003-03-06 | Lise Binderup | Combination medicament for treatment of neoplastic diseases |
| WO2002094813A1 (en) | 2001-05-24 | 2002-11-28 | Leo Pharma A/S | Novel pyridyl cyanoguanidine compounds |
| WO2002094265A1 (en) | 2001-05-24 | 2002-11-28 | Leo Pharma A/S | A method of modulating nf-$g(k)b activity |
| US6638679B2 (en) | 2001-07-12 | 2003-10-28 | Kodak Polychrome Graphics, Llc | Photosensitive compositions having mixtures of alkoxy and non-alkoxy diazonium salt containing compounds |
| SE0102617D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| SE0102616D0 (sv) | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| WO2003024935A2 (en) | 2001-09-19 | 2003-03-27 | Pharmacia Corporation | Substituted pyrazolyl compounds for the treatment of inflammation |
| BR0212661A (pt) | 2001-09-19 | 2004-08-24 | Pharmacia Corp | Compostos de pirazolil benzenossulfamida substituìdos para o tratamento de inflamação |
| US20030109550A1 (en) | 2001-09-19 | 2003-06-12 | Michael Clare | Substituted indazole compounds for the treatment of inflammation |
| CA2460939C (en) | 2001-09-19 | 2008-07-29 | Pharmacia Corporation | Substituted pyrazolyl compounds for the treatment of inflammation |
| BR0213734A (pt) | 2001-10-30 | 2004-10-19 | Pharmacia Corp | Derivados de carboxamida heteroaromático para o tratamento de inflamação |
| ATE370145T1 (de) | 2002-04-03 | 2007-09-15 | Bristol Myers Squibb Co | Tricyclische verbindungen auf thiophengrundlage und pharmazeutische zusammensetzungen, die diese enthalten |
| CA2485298C (en) | 2002-05-09 | 2008-03-11 | Pharmacia Corporation | Substituted pyrazolyl compounds for the treatment of inflammation |
| AU2003237330A1 (en) | 2002-06-06 | 2003-12-22 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 3-amino-thieno[2,3-b]pyridine-2-carboxylic acid amide compounds and processes for preparing and their uses |
| GB0217757D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | Novel compounds |
| AU2003261415C1 (en) * | 2002-08-09 | 2010-01-14 | Merck Sharp & Dohme Corp. | Tyrosine kinase inhibitors |
| DE10237722A1 (de) | 2002-08-17 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase |
| US7329668B2 (en) | 2003-02-25 | 2008-02-12 | Bristol-Myers Squibb Company | Pyrazolopurine-based tricyclic compounds and pharmaceutical compositions comprising same |
| GB0308466D0 (en) | 2003-04-11 | 2003-05-21 | Novartis Ag | Organic compounds |
| US7176214B2 (en) | 2003-05-21 | 2007-02-13 | Bristol-Myers Squibb Company | Imidazo-fused oxazolo[4,5-β]pyridine and imidazo-fused thiazolo[4,5-β]pyridine based tricyclic compounds and pharmaceutical compositions comprising same |
| WO2005012283A1 (en) | 2003-07-31 | 2005-02-10 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted benzothiophene compounds and uses thereof |
| US7265148B2 (en) * | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
| US7291733B2 (en) | 2003-10-10 | 2007-11-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted tricyclic heterocycles and their uses |
| US20070225291A1 (en) | 2003-10-14 | 2007-09-27 | Pfizer Inc. | Substituted Pyrazinone Compounds for the Treatment of Inflammation |
| GB0400895D0 (en) * | 2004-01-15 | 2004-02-18 | Smithkline Beecham Corp | Chemical compounds |
| TW200616967A (en) * | 2004-06-24 | 2006-06-01 | Smithkline Beecham Corp | Novel indazole carboxamides and their use |
| CN101060842A (zh) * | 2004-09-21 | 2007-10-24 | 葛兰素集团有限公司 | 化合物 |
| PE20060748A1 (es) * | 2004-09-21 | 2006-10-01 | Smithkline Beecham Corp | Derivados de indolcarboxamida como inhibidores de quinasa ikk2 |
-
2006
- 2006-06-28 AR ARP060102790A patent/AR055343A1/es not_active Application Discontinuation
- 2006-06-28 BR BRPI0611674-4A patent/BRPI0611674A2/pt not_active IP Right Cessation
- 2006-06-28 KR KR1020077030656A patent/KR20080021077A/ko not_active Ceased
- 2006-06-28 EP EP06785861A patent/EP1896014A4/en not_active Withdrawn
- 2006-06-28 JP JP2008519569A patent/JP5059756B2/ja not_active Expired - Fee Related
- 2006-06-28 AU AU2006266028A patent/AU2006266028B2/en not_active Ceased
- 2006-06-28 CA CA002613068A patent/CA2613068A1/en not_active Abandoned
- 2006-06-28 WO PCT/US2006/025402 patent/WO2007005534A2/en not_active Ceased
- 2006-06-28 UA UAA200714940A patent/UA99699C2/ru unknown
- 2006-06-28 CN CN2006800304481A patent/CN101247804B/zh not_active Expired - Fee Related
- 2006-06-28 EA EA200800183A patent/EA014083B1/ru not_active IP Right Cessation
- 2006-06-28 NZ NZ563687A patent/NZ563687A/en not_active IP Right Cessation
- 2006-06-28 TW TW095123240A patent/TWI380973B/zh not_active IP Right Cessation
- 2006-06-28 MX MX2007016541A patent/MX2007016541A/es active IP Right Grant
- 2006-06-28 PE PE2006000761A patent/PE20070173A1/es not_active Application Discontinuation
-
2007
- 2007-11-19 ZA ZA2007/09948A patent/ZA200709948B/en unknown
- 2007-11-29 IL IL187786A patent/IL187786A0/en unknown
- 2007-12-26 MA MA30513A patent/MA29566B1/fr unknown
-
2008
- 2008-01-24 NO NO20080457A patent/NO20080457L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AR055343A1 (es) | 2007-08-22 |
| UA99699C2 (ru) | 2012-09-25 |
| AU2006266028A1 (en) | 2007-01-11 |
| PE20070173A1 (es) | 2007-03-14 |
| TW200738588A (en) | 2007-10-16 |
| WO2007005534A8 (en) | 2008-01-17 |
| EA200800183A1 (ru) | 2008-08-29 |
| CN101247804B (zh) | 2012-09-26 |
| MA29566B1 (fr) | 2008-06-02 |
| WO2007005534A2 (en) | 2007-01-11 |
| JP2009500338A (ja) | 2009-01-08 |
| CN101247804A (zh) | 2008-08-20 |
| EP1896014A2 (en) | 2008-03-12 |
| EA014083B1 (ru) | 2010-08-30 |
| BRPI0611674A2 (pt) | 2009-04-28 |
| TWI380973B (zh) | 2013-01-01 |
| CA2613068A1 (en) | 2007-01-11 |
| WO2007005534A3 (en) | 2007-04-26 |
| ZA200709948B (en) | 2009-03-25 |
| NO20080457L (no) | 2008-01-29 |
| IL187786A0 (en) | 2008-08-07 |
| AU2006266028B2 (en) | 2012-03-15 |
| KR20080021077A (ko) | 2008-03-06 |
| EP1896014A4 (en) | 2010-07-21 |
| JP5059756B2 (ja) | 2012-10-31 |
| NZ563687A (en) | 2011-07-29 |
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