JP2016540786A5 - - Google Patents
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- JP2016540786A5 JP2016540786A5 JP2016539025A JP2016539025A JP2016540786A5 JP 2016540786 A5 JP2016540786 A5 JP 2016540786A5 JP 2016539025 A JP2016539025 A JP 2016539025A JP 2016539025 A JP2016539025 A JP 2016539025A JP 2016540786 A5 JP2016540786 A5 JP 2016540786A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- independently
- aryl
- alkoxy
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 229910052805 deuterium Inorganic materials 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 18
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 230000001404 mediated effect Effects 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- -1 n- propyl Chemical group 0.000 claims description 12
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 10
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 208000015114 central nervous system disease Diseases 0.000 claims description 9
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000002207 metabolite Substances 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 201000001119 neuropathy Diseases 0.000 claims description 6
- 230000007823 neuropathy Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 5
- 208000008589 Obesity Diseases 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 235000020824 obesity Nutrition 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical group O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229940124597 therapeutic agent Drugs 0.000 claims description 4
- IAXDNLOYHAJESK-UHFFFAOYSA-N 6-bromo-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonylindole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(Br)=CC=C3C=C2)C=C1N1CCNCC1 IAXDNLOYHAJESK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 2
- MAYQIFVKVAUMPD-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-methyl-4-piperazin-1-ylbenzimidazole Chemical compound CC1=NC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 MAYQIFVKVAUMPD-UHFFFAOYSA-N 0.000 claims description 2
- IBUHDDLETPJVGP-UHFFFAOYSA-N 2,8-dimethyl-5-(2-phenylethyl)-3,4-dihydro-1h-pyrido[4,3-b]indole Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=CC=C1 IBUHDDLETPJVGP-UHFFFAOYSA-N 0.000 claims description 2
- KSAUCBGUWGWPDL-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,7-dimethyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KSAUCBGUWGWPDL-UHFFFAOYSA-N 0.000 claims description 2
- WJBLNOPPDWQMCH-MBPVOVBZSA-N Nalmefene Chemical compound N1([C@@H]2CC3=CC=C(C=4O[C@@H]5[C@](C3=4)([C@]2(CCC5=C)O)CC1)O)CC1CC1 WJBLNOPPDWQMCH-MBPVOVBZSA-N 0.000 claims description 2
- XNBRWUQWSKXMPW-UHFFFAOYSA-N Tozadenant Chemical compound C1=2SC(NC(=O)N3CCC(C)(O)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 XNBRWUQWSKXMPW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims description 2
- PMKMNTBZJOXTJW-UHFFFAOYSA-N brilaroxazine Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)COC4=CC=3)CC2)=C1Cl PMKMNTBZJOXTJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 229960003530 donepezil Drugs 0.000 claims description 2
- 229960005297 nalmefene Drugs 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 2
- 229960001534 risperidone Drugs 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000002053 thietanyl group Chemical group 0.000 claims description 2
- 229950000564 tozadenant Drugs 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 235000019165 vitamin E Nutrition 0.000 claims description 2
- 239000011709 vitamin E Substances 0.000 claims description 2
- GBBSUAFBMRNDJC-MRXNPFEDSA-N (5R)-zopiclone Chemical compound C1CN(C)CCN1C(=O)O[C@@H]1C2=NC=CN=C2C(=O)N1C1=CC=C(Cl)C=N1 GBBSUAFBMRNDJC-MRXNPFEDSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims 1
- YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 claims 1
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims 1
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 claims 1
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 claims 1
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims 1
- 229960003914 desipramine Drugs 0.000 claims 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 1
- 229960004640 memantine Drugs 0.000 claims 1
- 229960001785 mirtazapine Drugs 0.000 claims 1
- RONZAEMNMFQXRA-UHFFFAOYSA-N mirtazapine Chemical compound C1C2=CC=CN=C2N2CCN(C)CC2C2=CC=CC=C21 RONZAEMNMFQXRA-UHFFFAOYSA-N 0.000 claims 1
- 229960003642 nicergoline Drugs 0.000 claims 1
- 229960001158 nortriptyline Drugs 0.000 claims 1
- 229960001476 pentoxifylline Drugs 0.000 claims 1
- 229960004526 piracetam Drugs 0.000 claims 1
- 229960004136 rivastigmine Drugs 0.000 claims 1
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 claims 1
- 229960003946 selegiline Drugs 0.000 claims 1
- 229960001685 tacrine Drugs 0.000 claims 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims 1
- 229960004688 venlafaxine Drugs 0.000 claims 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 claims 1
- 229960001475 zolpidem Drugs 0.000 claims 1
- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 claims 1
- 229960000820 zopiclone Drugs 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 11
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 8
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 4
- 208000020925 Bipolar disease Diseases 0.000 description 4
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 4
- 208000006029 Cardiomegaly Diseases 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 206010019280 Heart failures Diseases 0.000 description 4
- 208000026139 Memory disease Diseases 0.000 description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 4
- 208000018737 Parkinson disease Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 4
- 208000028683 bipolar I disease Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 4
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 4
- 208000002815 pulmonary hypertension Diseases 0.000 description 4
- 201000000980 schizophrenia Diseases 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 229920002873 Polyethylenimine Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 2
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical class ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 238000002600 positron emission tomography Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 238000002603 single-photon emission computed tomography Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- CWGFSQJQIHRAAE-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.OCC(N)(CO)CO CWGFSQJQIHRAAE-UHFFFAOYSA-N 0.000 description 1
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| CA2953004C (en) * | 2014-07-08 | 2023-02-21 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
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Family Cites Families (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002511097A (ja) | 1997-07-11 | 2002-04-09 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | ５−ｈｔ▲下６▼レセプターアンタゴニストであるスルホンアミド誘導体およびその製造方法 |
| EP0930302B1 (en) | 1998-01-16 | 2003-04-02 | F.Hoffmann-La Roche Ag | Benzosulfone derivatives |
| GB9801392D0 (en) | 1998-01-22 | 1998-03-18 | Smithkline Beecham Plc | Novel compounds |
| US6133287A (en) | 1998-03-24 | 2000-10-17 | Allelix Biopharmaceuticals Inc. | Piperidine-indole compounds having 5-HT6 affinity |
| GB9820113D0 (en) | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
| ATE375990T1 (de) | 1999-04-21 | 2007-11-15 | Nps Allelix Corp | Piperidin-indol derivate mit 5-ht6 affinität |
| CA2382247C (en) | 1999-08-12 | 2010-09-28 | Nps Allelix Corp. | Azaindoles having serotonin receptor affinity |
| AU1542201A (en) | 1999-11-05 | 2001-05-14 | Nps Allelix Corp. | Compounds having 5-HT6 receptor antagonist activity |
| KR100823908B1 (ko) | 2000-10-20 | 2008-04-21 | 바이오비트럼 에이비(피유비엘) | 2-, 3-, 4-, 또는 5-치환-ｎ1-(벤젠술포닐)인돌 및 이의치료 용도 |
| EP2298738B1 (en) | 2000-11-02 | 2012-09-19 | Wyeth LLC | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| WO2002041889A2 (en) | 2000-11-24 | 2002-05-30 | Smithkline Beecham P.L.C. | Indolsulfonyl compounds useful in the treatment of cns disorders |
| MXPA03005433A (es) | 2000-12-22 | 2003-09-10 | Wyeth Corp | Compuestos de heterociclilalquilindol o-azaindol como ligandos de 5-hidroxitriptamina-6. |
| JP4307073B2 (ja) | 2000-12-22 | 2009-08-05 | ワイス | ５−ヒドロキシトリプトアミン−６リガンドとしてのヘテロサイクルインダゾールおよびアザインダゾール化合物 |
| TW593278B (en) | 2001-01-23 | 2004-06-21 | Wyeth Corp | 1-aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| BR0207302A (pt) | 2001-02-08 | 2004-02-10 | Memory Pharm Corp | Trifluorometilpurinas como inibidores da fosfodiesterase 4 |
| CN1293072C (zh) | 2001-04-20 | 2007-01-03 | 惠氏公司 | 作为5－羟色胺－6配体的杂环基氧基－、－硫代－和－氨基吲哚衍生物 |
| AU2002309585B2 (en) | 2001-04-20 | 2008-01-31 | Wyeth | Heterocyclylalkoxy-, -alkylthio- and -alkylaminobenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| JP4187642B2 (ja) | 2001-06-07 | 2008-11-26 | エフ．ホフマン−ラ ロシュ アーゲー | ５−ｈｔ６受容体親和性を有する新規インドール誘導体 |
| KR20090019894A (ko) | 2001-06-11 | 2009-02-25 | 바이오비트럼 에이비(피유비엘) | 치환 술폰아미드 화합물, ｃｎｓ 장애, 비만 및 ⅱ 형 당뇨병 치료용 약제로서의 이들의 사용 방법 |
| ES2268113T3 (es) | 2001-06-15 | 2007-03-16 | F. Hoffmann-La Roche Ag | Derivados de 4-piperazinilindol con afinidad al receptor 5-ht6. |
| MXPA04001250A (es) | 2001-08-10 | 2004-05-27 | Hoffmann La Roche | Derivados de arilsulfonilo con afinidad receptora de 5-hidroxitriptamina6 (5-ht6). |
| TW200301251A (en) | 2001-12-20 | 2003-07-01 | Wyeth Corp | Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
| AU2002357270B2 (en) | 2001-12-20 | 2007-06-14 | Wyeth | Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
| GB0202679D0 (en) | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| EP1476428B1 (en) | 2002-02-22 | 2010-11-17 | Pharmacia & Upjohn Company LLC | Pyridyl sulfone derivatives as 5-ht6 receptor ligands |
| US20050124626A1 (en) | 2002-03-27 | 2005-06-09 | Johnson Christopher N. | Novel compounds |
| US6906095B2 (en) | 2002-05-10 | 2005-06-14 | Wyeth | Indolylalkylidenehydrazine-carboximidamide derivatives as 5-hydroxytryptamine-6 ligands |
| CN1293053C (zh) | 2002-06-05 | 2007-01-03 | 弗·哈夫曼-拉罗切有限公司 | 作为5－ht6－受体调节剂用于治疗cns－病症的1－磺酰基－4－氨基烷氧基吲哚衍生物 |
| NZ552282A (en) | 2002-06-20 | 2008-07-31 | Biovitrum Ab Publ | New compounds useful for the treatment of obesity, type II diabetes and CNS disorders |
| WO2004026831A1 (en) | 2002-09-17 | 2004-04-01 | F. Hoffmann-La Roche Ag | 2,4-substituted indoles and their use as 5-ht6 modulators |
| JP4327091B2 (ja) | 2002-09-17 | 2009-09-09 | エフ．ホフマン−ラ ロシュ アーゲー | ２，７−置換インドール及び５−ｈｔ６モジュレーターとしてのその使用 |
| WO2004035047A1 (en) * | 2002-10-18 | 2004-04-29 | F. Hoffmann-La Roche Ag | 4-piperazinyl benzenesulfonyl indoles with 5-ht6 receptor affinity |
| KR100776118B1 (ko) | 2002-11-28 | 2007-11-15 | 수벤 라이프 사이언시스 리미티드 | 엔-아릴술포닐-3-아미노알콕시인돌 |
| EP1581492B1 (en) | 2002-11-28 | 2008-07-16 | Suven Life Sciences Limited | N-arylsulfonyl-3-substituted indoles having serotonin receptor affinity, process for their preparation and pharmaceutical composition containing them |
| GB0305575D0 (en) | 2003-03-11 | 2003-04-16 | Glaxo Group Ltd | Novel compounds |
| SE0302760D0 (sv) | 2003-10-20 | 2003-10-20 | Biovitrum Ab | New compounds |
| WO2005066157A1 (en) | 2004-01-02 | 2005-07-21 | Suven Life Sciences | 3-(pyrolidin-3-l) indoles as 5-ht6 receptor modulators |
| EP1758884A2 (en) | 2004-05-20 | 2007-03-07 | Elan Pharmaceuticals, Inc. | N-cyclic sulfonamido inhibitors of gamma secretase |
| PE20060303A1 (es) | 2004-06-23 | 2006-05-19 | Wyeth Corp | Metabolitos de indolilalquilamina como ligandos de 5-hidroxitriptamina-6 |
| AR052308A1 (es) | 2004-07-16 | 2007-03-14 | Lundbeck & Co As H | Derivados de 2-(1h-indolilsulfanil)-arilamina y una composicion farmaceutica que contiene al compuesto |
| EP1632491A1 (en) | 2004-08-30 | 2006-03-08 | Laboratorios Del Dr. Esteve, S.A. | Substituted indole compounds and their use as 5-HT6 receptor modulators |
| EA013875B1 (ru) | 2005-08-12 | 2010-08-30 | Сувен Лайф Сайенсиз Лимитед | Аминоарильные сульфонамидные производные как функциональные 5-нтлиганды |
| WO2007020653A1 (en) | 2005-08-12 | 2007-02-22 | Suven Life Sciences Limited | Thioether derivatives as functional 5-ht6 ligands |
| AU2007217040A1 (en) | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Compounds having 5-HT6 receptor affinity |
| WO2007138611A1 (en) | 2006-05-30 | 2007-12-06 | Suven Life Sciences Limited | 3-(heterocyclyl)-n-(arylsulfonyl)indole derivatives as functional 5-ht6 ligands |
| EP2046741B1 (en) | 2006-07-03 | 2012-10-31 | Proximagen Ltd. | Indoles as 5-ht6 modulators |
| JP2010509266A (ja) | 2006-11-09 | 2010-03-25 | エフ．ホフマン−ラ ロシュ アーゲー | ５−ｈｔ６阻害剤としてのアリールスルホニルピロリジン |
| EA016015B1 (ru) | 2007-01-08 | 2012-01-30 | Сувен Лайф Сайенсиз Лимитед | 4-(гетероциклил)алкил-n-(арилсульфонил)индолсоединения и их применение в качестве 5-нтлигандов |
| ES2357584T3 (es) | 2007-01-08 | 2011-04-27 | Suven Life Sciences Limited | Compuestos de 5-(heterociclil) alquil-n-(arilsulfonil)indol y su uso como ligandos de 5-th6. |
| EP1947085A1 (en) | 2007-01-19 | 2008-07-23 | Laboratorios del Dr. Esteve S.A. | Substituted indole sulfonamide compounds, their preparation and use as medicaments |
| CA2676145A1 (en) | 2007-02-06 | 2008-08-14 | Novartis Ag | 1-benzenesulfonyl-1h-indole derivatives as inhibitors of ccr9 activity |
| AU2008216032A1 (en) | 2007-02-16 | 2008-08-21 | Memory Pharmaceuticals Corporation | 6 ' substituted indole and indazole derivatives having 5-HT6 receptor affinity |
| PE20090159A1 (es) | 2007-03-08 | 2009-02-21 | Plexxikon Inc | COMPUESTOS DERIVADOS DE ACIDO INDOL-PROPIONICO COMO MODULADORES PPARs |
| EP2155724A1 (en) | 2007-03-23 | 2010-02-24 | Abbott GmbH & Co. KG | Azetidin compounds suitable for treating disorders that respond to modulation of the serotonin 5-ht6 receptor |
| EA016594B1 (ru) | 2007-05-03 | 2012-06-29 | Сувен Лайф Сайенсиз Лимитед | Производные 1-(аминоалкоксиарилсульфонил)индола в качестве 5-нтлигандов |
| KR20100031578A (ko) * | 2007-05-24 | 2010-03-23 | 메모리 파마슈티칼스 코포레이션 | 5-ｈｔ6 수용체 친화성을 갖는 4'-치환된 화합물 |
| JP2010536789A (ja) | 2007-08-15 | 2010-12-02 | メモリー・ファーマシューティカルズ・コーポレイション | ５−ｈｔ６受容体親和性を有する３’置換化合物 |
| WO2009034581A1 (en) | 2007-09-11 | 2009-03-19 | Suven Life Sciences Limited | Substituted indolyl compounds and their use as 5-ht6 ligands |
| CA2703157C (en) | 2007-10-26 | 2013-02-05 | Suven Life Sciences Limited | Amino arylsulfonamide compounds and their use as 5-ht6 ligands |
| US20100016297A1 (en) * | 2008-06-24 | 2010-01-21 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| US20100022581A1 (en) * | 2008-07-02 | 2010-01-28 | Memory Pharmaceuticals Corporation | Pyrrolidine-substituted azaindole compounds having 5-ht6 receptor affinity |
| US20100029629A1 (en) | 2008-07-25 | 2010-02-04 | Memory Pharmaceuticals Corporation | Acyclic compounds having 5-ht6 receptor affinity |
| US20100056531A1 (en) | 2008-08-22 | 2010-03-04 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| US20100056491A1 (en) | 2008-08-29 | 2010-03-04 | Memory Pharmaceuticals Corporation | 4'-amino cyclic compounds having 5-ht6 receptor affinity |
| US8318725B2 (en) | 2008-09-17 | 2012-11-27 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-HT6 ligands |
| US8362010B2 (en) | 2009-04-30 | 2013-01-29 | Abbott Gmbh & Co. Kg | Benzenesulfonanilide compounds suitable for treating disorders that respond to modulation of the serotonin 5-HT6 receptor |
| US8343959B2 (en) | 2009-04-30 | 2013-01-01 | Abbott Gmbh & Co. Kg | N-phenyl-(piperazinyl or homopiperazinyl)-benzenesulfonamide or benzenesulfonyl-phenyl-(piperazine or homopiperazine) compounds suitable for treating disorders that respond to modulation of the serotonin 5-HT6 receptor |
| CN102459197B (zh) | 2009-04-30 | 2015-08-19 | Abbvie公司 | 适用于治疗响应血清素5-ht6受体的调节的病症的n-苯基-(哌嗪基或高哌嗪基)-苯磺酰胺或苯磺酰基-苯基-(哌嗪或高哌嗪)化合物 |
| MX2011011519A (es) | 2009-04-30 | 2012-01-30 | Abbott Gmbh & Co Kg | Compuestos de bencensulfonanilida adecuados para tratar trastornos que responden a la modulacion del receptor de serotonina 5-ht6. |
| US8119683B2 (en) | 2009-08-10 | 2012-02-21 | Taipei Medical University | Aryl substituted sulfonamide compounds and their use as anticancer agents |
| US8153680B2 (en) | 2009-08-25 | 2012-04-10 | The Ohio State University Research Foundation | Alkyl indole-3-carbinol-derived antitumor agents |
| WO2012059431A1 (en) | 2010-11-01 | 2012-05-10 | Abbott Gmbh & Co. Kg | Benzenesulfonyl or sulfonamide compounds suitable for treating disorders that respond to the modulation of the serotonin 5-ht6 receptor |
| WO2012059432A1 (en) | 2010-11-01 | 2012-05-10 | Abbott Gmbh & Co. Kg | N-phenyl-(homo)piperazinyl-benzenesulfonyl or benzenesulfonamide compounds suitable for treating disorders that respond to the modulation of the 5-ht6 receptor |
| JP6063870B2 (ja) | 2010-11-08 | 2017-01-18 | ライセラ・コーポレイション | ＲＯＲγ活性の阻害用のＮ−スルホニル化テトラヒドロキノリンおよび関連二環化合物および病気の治療 |
| US9051265B2 (en) | 2011-06-06 | 2015-06-09 | The Scripps Research Institute | N-benzylindole modulators of PPARG |
| CN104276993B (zh) | 2013-07-12 | 2019-03-15 | 广东东阳光药业有限公司 | 吲哚衍生物及其在药物上的应用 |
| CN104557726B (zh) | 2013-10-19 | 2019-05-24 | 广东东阳光药业有限公司 | 芳杂环类衍生物及其在药物上的应用 |
-
2014
- 2014-12-19 CN CN201410808745.0A patent/CN104725295B/zh active Active
- 2014-12-19 EP EP14871538.6A patent/EP3083588B1/en active Active
- 2014-12-19 JP JP2016539025A patent/JP6454346B2/ja active Active
- 2014-12-19 WO PCT/CN2014/094428 patent/WO2015090233A1/en not_active Ceased
- 2014-12-19 US US15/027,691 patent/US9663498B2/en active Active
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