JP2016540792A5 - - Google Patents
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- JP2016540792A5 JP2016540792A5 JP2016539896A JP2016539896A JP2016540792A5 JP 2016540792 A5 JP2016540792 A5 JP 2016540792A5 JP 2016539896 A JP2016539896 A JP 2016539896A JP 2016539896 A JP2016539896 A JP 2016539896A JP 2016540792 A5 JP2016540792 A5 JP 2016540792A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- phenyl
- methyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 165
- 125000000623 heterocyclic group Chemical group 0.000 claims description 123
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 92
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
- -1 ethylene, propylene, butylene, pentylene, hexylene, heptylene Chemical group 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 80
- 125000000304 alkynyl group Chemical group 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000003342 alkenyl group Chemical group 0.000 claims description 64
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 58
- 150000002367 halogens Chemical class 0.000 claims description 58
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 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 47
- 229920006395 saturated elastomer Polymers 0.000 claims description 47
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 45
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 claims description 44
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 43
- 229910052740 iodine Inorganic materials 0.000 claims description 42
- 229910052794 bromium Inorganic materials 0.000 claims description 41
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 34
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 32
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 28
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 28
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 28
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 28
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 28
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 28
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 28
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 28
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 28
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 28
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 28
- 229910052717 sulfur Inorganic materials 0.000 claims description 28
- 239000011593 sulfur Substances 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 27
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 20
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 20
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 17
- 229930192474 thiophene Natural products 0.000 claims description 16
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 claims description 15
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 15
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 14
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 14
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 14
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 14
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 14
- 239000012964 benzotriazole Substances 0.000 claims description 14
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 14
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 14
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 14
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 14
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 14
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 claims description 14
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 14
- 150000003536 tetrazoles Chemical class 0.000 claims description 14
- 150000003852 triazoles Chemical class 0.000 claims description 14
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 13
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000003222 pyridines Chemical class 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 150000003235 pyrrolidines Chemical class 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000011630 iodine Substances 0.000 claims description 3
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 claims description 3
- 229960003986 tuaminoheptane Drugs 0.000 claims description 3
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 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 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 208000004454 Hyperalgesia Diseases 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- 150000001556 benzimidazoles Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 150000001879 copper Chemical class 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000012046 mixed solvent Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 claims 1
- OHWJECJFVKKZMR-UHFFFAOYSA-N 3-[4-[(1-benzyltriazol-4-yl)methyl]piperazin-1-yl]phenol Chemical compound OC1=CC(=CC=C1)N1CCN(CC2=CN(CC3=CC=CC=C3)N=N2)CC1 OHWJECJFVKKZMR-UHFFFAOYSA-N 0.000 claims 1
- WMSIZSKZBUCEHA-UHFFFAOYSA-N 3-[4-[(1-phenylpyrazol-4-yl)methyl]piperazin-1-yl]phenol Chemical compound C1(=CC=CC=C1)N1N=CC(=C1)CN1CCN(CC1)C=1C=C(C=CC1)O WMSIZSKZBUCEHA-UHFFFAOYSA-N 0.000 claims 1
- PYDAINOAXWAHNN-UHFFFAOYSA-N 3-[4-[(1-phenyltriazol-4-yl)methyl]piperazin-1-yl]aniline Chemical compound C1(=CC=CC=C1)N1N=NC(=C1)CN1CCN(CC1)C=1C=C(N)C=CC=1 PYDAINOAXWAHNN-UHFFFAOYSA-N 0.000 claims 1
- UWMOCXBIPRMODY-UHFFFAOYSA-N 3-[4-[(1-phenyltriazol-4-yl)methyl]piperazin-1-yl]phenol Chemical compound C1(=CC=CC=C1)N1N=NC(=C1)CN1CCN(CC1)C=1C=C(C=CC1)O UWMOCXBIPRMODY-UHFFFAOYSA-N 0.000 claims 1
- IJCQVTXTRTXCKQ-UHFFFAOYSA-N 3-[4-[(1-pyridin-2-yltriazol-4-yl)methyl]piperazin-1-yl]phenol Chemical compound OC1=CC(=CC=C1)N1CCN(CC2=CN(N=N2)C2=NC=CC=C2)CC1 IJCQVTXTRTXCKQ-UHFFFAOYSA-N 0.000 claims 1
- 206010058019 Cancer Pain Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 208000035154 Hyperesthesia Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- SYOXPLIPOYMWBH-SZPZYZBQSA-N N-[3-[(1R,5S)-3-[(1-phenyltriazol-4-yl)methyl]-3,8-diazabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1(=CC=CC=C1)N1N=NC(=C1)CN1C[C@H]2CC[C@@H](C1)N2C=1C=C(C=CC=1)NS(=O)(=O)C SYOXPLIPOYMWBH-SZPZYZBQSA-N 0.000 claims 1
- JZYNQHYPIINROR-UHFFFAOYSA-N N-[3-[4-[(1-benzylpyrazol-4-yl)methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound C(C1=CC=CC=C1)N1N=CC(=C1)CN1CCN(CC1)C=1C=C(C=CC1)NS(=O)(=O)C JZYNQHYPIINROR-UHFFFAOYSA-N 0.000 claims 1
- FMROZDQOXRRQBA-UHFFFAOYSA-N N-[3-[4-[(1-benzyltriazol-4-yl)methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound C(C1=CC=CC=C1)N1N=NC(=C1)CN1CCN(CC1)C=1C=C(C=CC=1)NS(=O)(=O)C FMROZDQOXRRQBA-UHFFFAOYSA-N 0.000 claims 1
- RFNRKHAVTQDMLR-UHFFFAOYSA-N N-[3-[4-[(1-phenylpyrazol-4-yl)methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound C1(=CC=CC=C1)N1N=CC(=C1)CN1CCN(CC1)C=1C=C(C=CC1)NS(=O)(=O)C RFNRKHAVTQDMLR-UHFFFAOYSA-N 0.000 claims 1
- LKIFLEOHZPMIIU-UHFFFAOYSA-N N-[3-[4-[(1-phenyltriazol-4-yl)methyl]-1,4-diazepan-1-yl]phenyl]methanesulfonamide Chemical compound C1(=CC=CC=C1)N1N=NC(=C1)CN1CCN(CCC1)C=1C=C(C=CC1)NS(=O)(=O)C LKIFLEOHZPMIIU-UHFFFAOYSA-N 0.000 claims 1
- ZHODOIJXILJEIM-UHFFFAOYSA-N N-[3-[4-[(1-phenyltriazol-4-yl)methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC(=CC=C1)N1CCN(CC2=CN(N=N2)C2=CC=CC=C2)CC1 ZHODOIJXILJEIM-UHFFFAOYSA-N 0.000 claims 1
- KHBBVGYFILAJEY-UHFFFAOYSA-N N-[3-[4-[(1-pyridin-2-ylpyrazol-4-yl)methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound N1=C(C=CC=C1)N1N=CC(=C1)CN1CCN(CC1)C=1C=C(C=CC1)NS(=O)(=O)C KHBBVGYFILAJEY-UHFFFAOYSA-N 0.000 claims 1
- CHLUHDHVLQKJKU-UHFFFAOYSA-N N-[3-[4-[[1-(pyridin-2-ylmethyl)pyrazol-4-yl]methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound N1=C(C=CC=C1)CN1N=CC(=C1)CN1CCN(CC1)C=1C=C(C=CC=1)NS(=O)(=O)C CHLUHDHVLQKJKU-UHFFFAOYSA-N 0.000 claims 1
- NIQUJZPSSVJAIE-UHFFFAOYSA-N N-[3-[[1-[(1-phenyltriazol-4-yl)methyl]azetidin-3-yl]amino]phenyl]methanesulfonamide Chemical compound C1(=CC=CC=C1)N1N=NC(=C1)CN1CC(C1)NC=1C=C(C=CC=1)NS(=O)(=O)C NIQUJZPSSVJAIE-UHFFFAOYSA-N 0.000 claims 1
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| JP2018521090A (ja) * | 2015-07-29 | 2018-08-02 | ラボラトリオス・デル・デエレ・エステベ・エセ・ア | 疼痛に対する多様な活性を有するアミド誘導体 |
| AR105522A1 (es) * | 2015-07-29 | 2017-10-11 | Esteve Labor Dr | Derivados de amida sustituida que tienen actividad multimodal contra el dolor |
| JP2019516736A (ja) * | 2016-05-20 | 2019-06-20 | エステベ ファーマシューティカルズ，エセ．アー． | 疼痛に対する多様な活性を有するテトラヒドロピラン誘導体およびチオピラン誘導体 |
| US10961249B2 (en) * | 2017-03-21 | 2021-03-30 | Temple University-Of The Commonwealth System Of Higher Education | Modulators of the sigma-2 receptor and their method of use |
| JP7365238B2 (ja) * | 2017-03-21 | 2023-10-19 | テンプル・ユニバーシティ－オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | ５－ヒドロキシトリプタミン受容体７調節物質および治療剤としてのその使用 |
| MD3762368T2 (ro) | 2018-03-08 | 2022-07-31 | Incyte Corp | Compuși diol aminopirazină ca inhibitori ai PI3K-Y |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| TWI824050B (zh) * | 2018-10-31 | 2023-12-01 | 西班牙塔拉森斯調理協會 | 化合物、製備化合物的方法、化合物的用途、藥物組合物、用作藥物的化合物及用作治療疼痛的藥物的化合物 |
| EP3753932A1 (en) * | 2019-06-17 | 2020-12-23 | Esteve Pharmaceuticals, S.A. | Substituted bicyclic derivatives having multimodal activity against pain |
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| FR2580648B1 (fr) * | 1985-04-17 | 1987-05-15 | Adir | Nouveaux derives du triazole, leur procede de preparation et les compositions pharmaceutiques les renfermant |
| DK93087A (da) * | 1986-02-27 | 1987-08-28 | Duphar Int Res | Hidtil ukendte aryl substituerede (n-piperidinyl)methyl- og (n-piperazinyl)methylazoler med antipsykotiske egenskaber |
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| WO2007123269A1 (ja) * | 2006-04-19 | 2007-11-01 | Astellas Pharma Inc. | アゾールカルボキサミド誘導体 |
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| KR20090029274A (ko) * | 2006-07-21 | 2009-03-20 | 아이알엠 엘엘씨 | Ｉｔｐｋｂ 억제제로서의 화합물 및 조성물 |
| MX2009004786A (es) * | 2006-10-31 | 2009-06-05 | Schering Corp | Derivados de anilinopiperazina y sus metodos de uso. |
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| RU2498982C2 (ru) * | 2007-04-16 | 2013-11-20 | Грюненталь Гмбх | Новые лиганды ванилоидных рецепторов и их применение для изготовления лекарственных средств |
| EP1982714A1 (en) * | 2007-04-16 | 2008-10-22 | Laboratorios del Dr. Esteve S.A. | Pyrano-pyrazole-amines |
| DK2155717T3 (da) * | 2007-05-11 | 2012-11-19 | Lilly Co Eli | 2-[4-(pyrazol-4-ylalkyl)piperazin-1-yl]-3-phenyl-pyraziner og -pyridiner og 3-[4-(pyrazol-4-ylalkyl)piperazin-1-yl]-2-phenyl-pyridiner som 5-ht7-receptorantagonister |
| US7842696B2 (en) | 2007-06-21 | 2010-11-30 | Forest Laboratories Holdings Limited | Piperazine derivatives as inhibitors of stearoyl-CoA desaturase |
| TW200914020A (en) * | 2007-08-28 | 2009-04-01 | Lilly Co Eli | Substituted piperazinyl pyrazines and pyridines as 5-HT7 receptor antagonists |
| KR20140139125A (ko) | 2007-08-31 | 2014-12-04 | 퍼듀 퍼머 엘피 | 치환-퀴녹살린-형 피페리딘 화합물 및 그의 용도 |
| WO2010046780A2 (en) | 2008-10-22 | 2010-04-29 | Institut Pasteur Korea | Anti viral compounds |
| CN102271681B (zh) * | 2008-11-04 | 2014-11-12 | 凯莫森特里克斯股份有限公司 | Cxcr7调节剂 |
| US8853202B2 (en) * | 2008-11-04 | 2014-10-07 | Chemocentryx, Inc. | Modulators of CXCR7 |
| EP2375899B1 (en) | 2009-01-12 | 2015-02-25 | Array Biopharma Inc. | Piperidine-containing compounds and use thereof in the treatment of diabetes |
| MX340870B (es) | 2010-02-12 | 2016-07-27 | Pharmascience Inc | Compuestos de unión del dominio de repetición de inhibidores de proteínas de apoptosis de baculovirus. |
| EP2395003A1 (en) * | 2010-05-27 | 2011-12-14 | Laboratorios Del. Dr. Esteve, S.A. | Pyrazole compounds as sigma receptor inhibitors |
| EP2576520A1 (en) | 2010-05-28 | 2013-04-10 | GE Healthcare UK Limited | Radiolabeled compounds and methods thereof |
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