MX2007010227A - Derivados de tetrahidroindolona y tetrahidroindazolona. - Google Patents
Derivados de tetrahidroindolona y tetrahidroindazolona.Info
- Publication number
- MX2007010227A MX2007010227A MX2007010227A MX2007010227A MX2007010227A MX 2007010227 A MX2007010227 A MX 2007010227A MX 2007010227 A MX2007010227 A MX 2007010227A MX 2007010227 A MX2007010227 A MX 2007010227A MX 2007010227 A MX2007010227 A MX 2007010227A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- oxo
- tetrahydro
- benzamide
- trimethyl
- Prior art date
Links
- QPNLUIFEKCYQHR-UHFFFAOYSA-N 1,2,3a,4-tetrahydroindazol-3-one Chemical class C1=CCC2C(=O)NNC2=C1 QPNLUIFEKCYQHR-UHFFFAOYSA-N 0.000 title 1
- YJJUTLWYXYQJNJ-UHFFFAOYSA-N 1,3,3a,4-tetrahydroindol-2-one Chemical compound C1C=CC=C2NC(=O)CC21 YJJUTLWYXYQJNJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 408
- 150000003839 salts Chemical class 0.000 claims abstract description 89
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 55
- 238000011282 treatment Methods 0.000 claims abstract description 48
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 44
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 201000011510 cancer Diseases 0.000 claims abstract description 26
- 206010061218 Inflammation Diseases 0.000 claims abstract description 16
- 230000004054 inflammatory process Effects 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 206010003246 arthritis Diseases 0.000 claims abstract description 13
- 230000004663 cell proliferation Effects 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 1782
- 125000000217 alkyl group Chemical group 0.000 claims description 512
- -1 cyano, carboxy Chemical group 0.000 claims description 467
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 296
- 125000004429 atom Chemical group 0.000 claims description 209
- 125000005843 halogen group Chemical group 0.000 claims description 170
- 125000001188 haloalkyl group Chemical group 0.000 claims description 152
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 128
- 239000001257 hydrogen Substances 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 123
- 125000003545 alkoxy group Chemical group 0.000 claims description 120
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 110
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 103
- 125000003342 alkenyl group Chemical group 0.000 claims description 102
- 125000000304 alkynyl group Chemical group 0.000 claims description 101
- 125000004043 oxo group Chemical group O=* 0.000 claims description 97
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 91
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical group FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 88
- 125000005518 carboxamido group Chemical group 0.000 claims description 87
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 87
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 86
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 86
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 85
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 83
- 229910052799 carbon Inorganic materials 0.000 claims description 82
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 77
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 77
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 76
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 73
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 66
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 63
- 125000001072 heteroaryl group Chemical group 0.000 claims description 63
- 229910052717 sulfur Inorganic materials 0.000 claims description 63
- 229910052760 oxygen Inorganic materials 0.000 claims description 62
- 125000004434 sulfur atom Chemical group 0.000 claims description 61
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 40
- 239000003814 drug Substances 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 33
- 208000035475 disorder Diseases 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 21
- 102000004169 proteins and genes Human genes 0.000 claims description 21
- 108090000623 proteins and genes Proteins 0.000 claims description 21
- 208000015181 infectious disease Diseases 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- 150000003857 carboxamides Chemical class 0.000 claims description 16
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 12
- 241000224016 Plasmodium Species 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 244000045947 parasite Species 0.000 claims description 11
- 150000001721 carbon Chemical group 0.000 claims description 10
- 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 10
- 230000001842 fibrogenetic effect Effects 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 239000002671 adjuvant Substances 0.000 claims description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 206010017533 Fungal infection Diseases 0.000 claims description 6
- 208000031888 Mycoses Diseases 0.000 claims description 6
- 241000223960 Plasmodium falciparum Species 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 230000002062 proliferating effect Effects 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000009885 systemic effect Effects 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 208000020446 Cardiac disease Diseases 0.000 claims description 4
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 229940121375 antifungal agent Drugs 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 208000019622 heart disease Diseases 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 201000006334 interstitial nephritis Diseases 0.000 claims description 4
- 208000028867 ischemia Diseases 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 208000030159 metabolic disease Diseases 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- IMHFIQCVCFFHKF-UHFFFAOYSA-N 2-bromo-4-(3,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzonitrile Chemical compound C1=2CC(C)(C)CC(=O)C=2C(C)=CN1C1=CC=C(C#N)C(Br)=C1 IMHFIQCVCFFHKF-UHFFFAOYSA-N 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 239000002246 antineoplastic agent Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims description 3
- 208000011379 keloid formation Diseases 0.000 claims description 3
- 238000001959 radiotherapy Methods 0.000 claims description 3
- 241000894007 species Species 0.000 claims description 3
- 125000005960 1,4-diazepanyl group Chemical group 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 239000003429 antifungal agent Substances 0.000 claims description 2
- 125000003725 azepanyl group Chemical group 0.000 claims description 2
- 230000036210 malignancy Effects 0.000 claims description 2
- 230000003211 malignant effect Effects 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 213
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 25
- 150000002431 hydrogen Chemical group 0.000 claims 18
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 16
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 9
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 8
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 6
- 239000005711 Benzoic acid Substances 0.000 claims 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 6
- 235000010233 benzoic acid Nutrition 0.000 claims 6
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 5
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 4
- 125000005336 allyloxy group Chemical group 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-M L-alaninate Chemical compound C[C@H](N)C([O-])=O QNAYBMKLOCPYGJ-REOHCLBHSA-M 0.000 claims 3
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical compound CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims 3
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
- 125000006309 butyl amino group Chemical group 0.000 claims 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 2
- UISMCSZGMQXHCU-UHFFFAOYSA-N 2,6,6-trimethyl-5,7-dihydro-1h-indol-4-one Chemical compound N1C(C)=CC2=C1CC(C)(C)CC2=O UISMCSZGMQXHCU-UHFFFAOYSA-N 0.000 claims 2
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-UWTATZPHSA-M D-alaninate Chemical compound C[C@@H](N)C([O-])=O QNAYBMKLOCPYGJ-UWTATZPHSA-M 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 102100032510 Heat shock protein HSP 90-beta Human genes 0.000 claims 2
- 101001016856 Homo sapiens Heat shock protein HSP 90-beta Proteins 0.000 claims 2
- 101000988090 Leishmania donovani Heat shock protein 83 Proteins 0.000 claims 2
- JOGYJSWMNZFXIT-UHFFFAOYSA-N N'-(thian-4-yl)benzohydrazide Chemical compound C(C1=CC=CC=C1)(=O)NNC1CCSCC1 JOGYJSWMNZFXIT-UHFFFAOYSA-N 0.000 claims 2
- CWAVJWRJEOJGJN-UHFFFAOYSA-N N-(2,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound Cc1cc2c(CC(C)(C)CC2=O)n1NC(=O)c1ccccc1 CWAVJWRJEOJGJN-UHFFFAOYSA-N 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- QFOFHVLDBOVMQI-DKWTVANSSA-N (2S)-2-aminopropanoic acid methanesulfonic acid Chemical compound S(C)(=O)(=O)O.N[C@@H](C)C(=O)O QFOFHVLDBOVMQI-DKWTVANSSA-N 0.000 claims 1
- ZBMHORQWJYDOEB-WCCKRBBISA-N (2s)-2-amino-3-methylbutanoic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC(C)[C@H](N)C(O)=O ZBMHORQWJYDOEB-WCCKRBBISA-N 0.000 claims 1
- KQPNNGHKYLJOMB-UHFFFAOYSA-N (4-hydroxycyclohexyl) methanesulfonate Chemical compound CS(=O)(=O)OC1CCC(O)CC1 KQPNNGHKYLJOMB-UHFFFAOYSA-N 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- QTRYLSXMZATWAB-UHFFFAOYSA-N 2-(2,3-dihydroxypropylamino)-4-[6,6-dimethyl-4-oxo-3-(trifluoromethyl)-5,7-dihydroindazol-1-yl]benzamide Chemical compound O=C1CC(C)(C)CC2=C1C(C(F)(F)F)=NN2C1=CC=C(C(N)=O)C(NCC(O)CO)=C1 QTRYLSXMZATWAB-UHFFFAOYSA-N 0.000 claims 1
- RXRKQIOQFJFXGR-UHFFFAOYSA-N 2-(2,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound CC=1N(C=2CC(CC(C2C1)=O)(C)C)C1=C(C(=O)N)C=CC=C1 RXRKQIOQFJFXGR-UHFFFAOYSA-N 0.000 claims 1
- MDOSVPWIRUKODC-UHFFFAOYSA-N 2-(2-methoxyethylamino)-4-(3,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound C1=C(C(N)=O)C(NCCOC)=CC(N2C3=C(C(CC(C)(C)C3)=O)C(C)=C2)=C1 MDOSVPWIRUKODC-UHFFFAOYSA-N 0.000 claims 1
- ONWOLFRMYZHLEQ-UHFFFAOYSA-N 2-(3,4,5-trimethoxyanilino)-4-(2,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2C(=CC=C(C=2)N2C3=C(C(CC(C)(C)C3)=O)C=C2C)C(N)=O)=C1 ONWOLFRMYZHLEQ-UHFFFAOYSA-N 0.000 claims 1
- OWSIHWQXSVOXSU-UHFFFAOYSA-N 2-(4-methoxyanilino)-4-(2,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound C1=CC(OC)=CC=C1NC1=CC(N2C3=C(C(CC(C)(C)C3)=O)C=C2C)=CC=C1C(N)=O OWSIHWQXSVOXSU-UHFFFAOYSA-N 0.000 claims 1
- LTWDQYVINBHCBO-UHFFFAOYSA-N 2-(benzylamino)-4-(2,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound CC1=CC(C(CC(C)(C)C2)=O)=C2N1C(C=1)=CC=C(C(N)=O)C=1NCC1=CC=CC=C1 LTWDQYVINBHCBO-UHFFFAOYSA-N 0.000 claims 1
- QJGYVXXTSDYNNQ-UHFFFAOYSA-N 2-(carbamoylamino)-4-(3,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound C1=2CC(C)(C)CC(=O)C=2C(C)=CN1C1=CC=C(C(N)=O)C(NC(N)=O)=C1 QJGYVXXTSDYNNQ-UHFFFAOYSA-N 0.000 claims 1
- FMOSGTTYAFQMSD-UHFFFAOYSA-N 2-[(4-hydroxycyclohexyl)amino]-4-(3,6,6-trimethyl-4-oxo-5,7-dihydroindazol-1-yl)benzamide Chemical compound C1=2CC(C)(C)CC(=O)C=2C(C)=NN1C(C=1)=CC=C(C(N)=O)C=1NC1CCC(O)CC1 FMOSGTTYAFQMSD-UHFFFAOYSA-N 0.000 claims 1
- NLVGCYUZIQJCDS-UHFFFAOYSA-N 2-[(4-oxocyclohexyl)amino]-4-(3,6,6-trimethyl-4-oxo-5,7-dihydroindol-1-yl)benzamide Chemical compound C1=2CC(C)(C)CC(=O)C=2C(C)=CN1C(C=1)=CC=C(C(N)=O)C=1NC1CCC(=O)CC1 NLVGCYUZIQJCDS-UHFFFAOYSA-N 0.000 claims 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims 1
- SKYYKWPAURBNOV-UHFFFAOYSA-N 2-[2-(dimethylsulfamoyl)ethylamino]-4-(3,6,6-trimethyl-4-oxo-5,7-dihydroindazol-1-yl)benzamide Chemical compound C1=C(C(N)=O)C(NCCS(=O)(=O)N(C)C)=CC(N2C3=C(C(CC(C)(C)C3)=O)C(C)=N2)=C1 SKYYKWPAURBNOV-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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| US20080269193A1 (en) * | 2007-04-16 | 2008-10-30 | Kenneth He Huang | Tetrahydroindole and Tetrahydroindazole Derivatives |
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| FR2955323B1 (fr) * | 2010-01-19 | 2015-01-16 | Sanofi Aventis | Nouveaux derives d'indazole inhibiteurs d'hsp90, compositions les contenant et utilisation |
| FR2943341B1 (fr) * | 2009-03-19 | 2011-03-11 | Sanofi Aventis | Nouveaux derives d'indazole inhibiteurs d'hsp90,compositions les contenant et utilisation |
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| EP2770327B1 (en) * | 2009-03-30 | 2017-06-14 | Nordic Bioscience A/S | Fibrosis biomarker assay |
| AR077405A1 (es) | 2009-07-10 | 2011-08-24 | Sanofi Aventis | Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer |
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| CN101872359B (zh) * | 2010-06-11 | 2013-08-14 | 北京邮电大学 | 实现演变点发现的社会网络演化分析方法及系统 |
| CN102311389A (zh) * | 2010-06-29 | 2012-01-11 | 王小龙 | 一种氮芳香取代吡唑衍生物、及其合成和抗癌应用 |
| CN101955461B (zh) * | 2010-10-08 | 2012-11-21 | 广州暨南生物医药研究开发基地有限公司 | 一种Hsp90抑制剂Xbj-B11及其制备方法与应用 |
| CN101967125B (zh) | 2010-10-08 | 2012-07-04 | 广州暨南生物医药研究开发基地有限公司 | 一种Hsp90抑制剂Xbj-B16-1及其制备方法与应用 |
| BR112013023452A2 (pt) | 2011-03-15 | 2016-12-06 | Univ British Columbia | combinação de oligonucleotídeo anti-clusterina com inibidor de hsp90 para o tratamento de câncer de próstata |
| CN102675288B (zh) * | 2011-03-18 | 2014-01-01 | 北京师范大学 | 2-((2-(双(2-吡啶甲基)氨基)乙基)氨基)-4-(3,6,6-三甲基-4-氧-4,5,6,7-四氢吲唑基)苯甲酰胺及制备、应用 |
| JP2014534228A (ja) | 2011-11-02 | 2014-12-18 | シンタ ファーマシューティカルズ コーポレーション | 白金含有剤とhsp90阻害剤の組合せ療法 |
| JP2014532712A (ja) | 2011-11-02 | 2014-12-08 | シンタ ファーマシューティカルズ コーポレーション | トポイソメラーゼi阻害剤とhsp90阻害剤の組合せを使用する癌療法 |
| AU2012339679A1 (en) | 2011-11-14 | 2014-06-12 | Synta Pharmaceuticals Corp. | Combination therapy of Hsp90 inhibitors with BRAF inhibitors |
| EP2879675B1 (en) | 2012-08-06 | 2019-11-13 | Duke University | Compounds and methods for targeting hsp90 |
| CN103467356B (zh) * | 2013-08-12 | 2015-04-01 | 绍兴文理学院 | 一种四氢吲哚化合物及其制备方法与应用 |
| SG11201700777VA (en) | 2014-08-04 | 2017-02-27 | Nuevolution As | Optionally fused heterocyclyl-substituted derivatives of pyrimidine useful for the treatment of inflammatory, metabolic, oncologic and autoimmune diseases |
| EP3191473A1 (en) * | 2014-09-11 | 2017-07-19 | Esanex, Inc. | Indazolyl- and indolyl-benzamide derivatives |
| WO2016086153A2 (en) | 2014-11-26 | 2016-06-02 | Esanex, Inc. | Use of tetrahydro!ndazolylbeimzamide and tetrahydroindolylbenzamide derivatives for the treatment of human immunodeficiency virus (hiv) and acquired immune deficiency syndrome (aids) |
| CN104592230B (zh) * | 2015-01-30 | 2017-02-01 | 广州暨南生物医药研究开发基地有限公司 | 一种2‑(石榴皮烷‑3‑氨基)‑4‑四氢吲唑取代的苯甲酰胺化合物及其应用 |
| CN104592203A (zh) * | 2015-01-30 | 2015-05-06 | 广州暨南生物医药研究开发基地有限公司 | 一种2-氨基-4-四氢吲唑取代的苯甲酰胺化合物及其在制备抗肿瘤药物中的应用 |
| US9737509B1 (en) | 2015-05-26 | 2017-08-22 | University Of South Florida | Antimicrobial compositions, methods of use, and methods of treatment of infections |
| WO2017059434A1 (en) | 2015-10-02 | 2017-04-06 | Esanex, Inc. | Use of tetrahydroindazolylbenzamide and tetrahydroindolylbenzamide derivatives for the treatment of cancer |
| KR102073779B1 (ko) * | 2015-10-13 | 2020-02-05 | 니혼노야쿠가부시키가이샤 | 옥심기를 가지는 축합복소환 화합물 또는 그의 염류 및 상기 화합물을 함유하는 농원예용 살충제 및 그 사용 방법 |
| WO2017184956A1 (en) | 2016-04-22 | 2017-10-26 | Duke University | Compounds and methods for targeting hsp90 |
| KR20190009346A (ko) * | 2016-05-18 | 2019-01-28 | 에사넥스, 인코포레이티드 | 암의 치료를 위한 인다졸릴벤즈아미드 유도체를 이용한 조합 요법 |
| EP3515436A1 (en) | 2016-09-23 | 2019-07-31 | Esanex, Inc. | Combination therapies using indazolylbenzamide derivatives for the treatment of cancer |
| US11014927B2 (en) | 2017-03-20 | 2021-05-25 | Forma Therapeutics, Inc. | Pyrrolopyrrole compositions as pyruvate kinase (PKR) activators |
| US12053458B2 (en) | 2018-09-19 | 2024-08-06 | Novo Nordisk Health Care Ag | Treating sickle cell disease with a pyruvate kinase R activating compound |
| ES2989438T3 (es) | 2018-09-19 | 2024-11-26 | Novo Nordisk Healthcare Ag | Activación de la piruvato cinasa R |
| EP4031132A4 (en) | 2019-09-19 | 2023-09-13 | Forma Therapeutics, Inc. | Activating pyruvate kinase r |
| US11685727B2 (en) | 2019-12-20 | 2023-06-27 | Nuevolution A/S | Compounds active towards nuclear receptors |
| JP2021098692A (ja) | 2019-12-20 | 2021-07-01 | ヌエヴォリューション・アクティーゼルスカブNuevolution A/S | 核内受容体に対して活性の化合物 |
| JP7713954B2 (ja) | 2020-03-31 | 2025-07-28 | ヌエヴォリューション・アクティーゼルスカブ | 核内受容体に対して活性な化合物 |
| MX2022012260A (es) | 2020-03-31 | 2022-11-30 | Nuevolution As | Compuestos activos frente a receptores nucleares. |
| CN117126097A (zh) * | 2020-06-11 | 2023-11-28 | 贝达药业股份有限公司 | 双环化合物及其应用 |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
| CN114213332B (zh) * | 2022-02-21 | 2022-05-17 | 深圳市人民医院 | 一种四氢吲唑类化合物及其制备方法和应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4024862A1 (de) | 1990-08-04 | 1992-02-13 | Hoechst Ag | 4,5,6,7-tetrahydro-3-aryl-indazole, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| GB9812038D0 (en) * | 1998-06-04 | 1998-07-29 | Merck Sharp & Dohme | Therapeutic compound |
| GB9900222D0 (en) * | 1999-01-06 | 1999-02-24 | Merck Sharp & Dohme | Therapeutic compounds |
| GB9911053D0 (en) * | 1999-05-12 | 1999-07-14 | Pharmacia & Upjohn Spa | 4,5,6,7-tetrahydroindazole derivatives process for their preparation and their use as antitumour agents |
| WO2002020480A1 (en) * | 2000-09-06 | 2002-03-14 | Neurogen Corporation | Substituted fused pyrroleimines and pyrazoleimines |
| EP1431267A4 (en) | 2001-08-09 | 2004-12-22 | Ono Pharmaceutical Co | COMPOUNDS DERIVED FROM CARBOXYLIC ACID AND MEDICAMENTS COMPRISING SUCH COMPOUNDS AS ACTIVE INGREDIENT |
| DE10148618B4 (de) * | 2001-09-25 | 2007-05-03 | Schering Ag | Substituierte N-(1,4,5,6-Tetrahydro-cyclopentapyrazol-3-yl)-Derivate, deren Herstellung und Verwendung als Arzneimittel |
| AU2003217870A1 (en) * | 2002-03-01 | 2003-09-16 | Pintex Pharmaceuticals, Inc. | Pini-modulating compounds and methods of use thereof |
| AU2003288994A1 (en) | 2002-12-10 | 2004-06-30 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic compounds and medicinal use thereof |
| PE20040804A1 (es) | 2002-12-19 | 2004-12-31 | Boehringer Ingelheim Pharma | DERIVADOS DE CARBOXAMIDAS COMO INHIBIDORES DEL FACTOR Xa |
| KR101617774B1 (ko) * | 2005-02-25 | 2016-05-04 | 에사넥스, 인코포레이티드 | 테트라히드로인돌론 및 테트라히드로인다졸론 유도체 |
| JPWO2006109846A1 (ja) | 2005-04-06 | 2008-11-20 | 武田薬品工業株式会社 | トリアゾール誘導体およびその用途 |
| US20080269193A1 (en) * | 2007-04-16 | 2008-10-30 | Kenneth He Huang | Tetrahydroindole and Tetrahydroindazole Derivatives |
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