JP2017502010A5 - - Google Patents
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- JP2017502010A5 JP2017502010A5 JP2016539899A JP2016539899A JP2017502010A5 JP 2017502010 A5 JP2017502010 A5 JP 2017502010A5 JP 2016539899 A JP2016539899 A JP 2016539899A JP 2016539899 A JP2016539899 A JP 2016539899A JP 2017502010 A5 JP2017502010 A5 JP 2017502010A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- ring
- cycloalkyl
- 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.)
- Ceased
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- 125000000217 alkyl group Chemical group 0.000 claims description 120
- 125000000623 heterocyclic group Chemical group 0.000 claims description 93
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 57
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 52
- 125000003342 alkenyl group Chemical group 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 125000000304 alkynyl group Chemical group 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 38
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 35
- 229920006395 saturated elastomer Polymers 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- 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 29
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 claims description 28
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 28
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- -1 Doll Chemical compound 0.000 claims description 25
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 24
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 20
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 20
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 20
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 20
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 20
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 20
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 239000011593 sulfur Substances 0.000 claims description 20
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 claims description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 19
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 18
- 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 18
- 125000004429 atom Chemical group 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
- 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 16
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 13
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 claims description 11
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 10
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 10
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 10
- 239000012964 benzotriazole Substances 0.000 claims description 10
- 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 10
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 10
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical compound C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 claims description 10
- 150000003536 tetrazoles Chemical class 0.000 claims description 10
- 229930192474 thiophene Natural products 0.000 claims description 10
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 9
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 9
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 9
- 150000003852 triazoles Chemical class 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 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 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 claims description 5
- 229960003986 tuaminoheptane Drugs 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 150000003235 pyrrolidines Chemical class 0.000 claims description 2
- 230000003796 beauty Effects 0.000 claims 24
- 150000003839 salts Chemical class 0.000 claims 10
- 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 7
- 239000000203 mixture Substances 0.000 claims 7
- 208000002193 Pain Diseases 0.000 claims 5
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 208000004454 Hyperalgesia Diseases 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 150000002460 imidazoles Chemical class 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- YWCNJJKFDHWKNT-UHFFFAOYSA-N 1H-imidazole oxadiazole Chemical compound O1N=NC=C1.N1C=NC=C1 YWCNJJKFDHWKNT-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 206010058019 Cancer Pain Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 206010053552 allodynia Diseases 0.000 claims 1
- 150000001556 benzimidazoles Chemical group 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000009977 dual effect Effects 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 239000012046 mixed solvent Substances 0.000 claims 1
- 102000051367 mu Opioid Receptors Human genes 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 235000010378 sodium ascorbate Nutrition 0.000 claims 1
- 229960005055 sodium ascorbate Drugs 0.000 claims 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 208000009935 visceral pain Diseases 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 108020001612 μ-opioid receptors Proteins 0.000 claims 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 10
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- YVXHZKKCZYLQOP-UHFFFAOYSA-N hept-1-yne Chemical compound CCCCCC#C YVXHZKKCZYLQOP-UHFFFAOYSA-N 0.000 description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 0 Cc1cccc2c1*C*2 Chemical compound Cc1cccc2c1*C*2 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13384004 | 2013-12-20 | ||
| EP13384004.1 | 2013-12-20 | ||
| PCT/EP2014/078717 WO2015091939A1 (en) | 2013-12-20 | 2014-12-19 | Piperidine derivatives having multimodal activity against pain |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017502010A JP2017502010A (ja) | 2017-01-19 |
| JP2017502010A5 true JP2017502010A5 (enExample) | 2018-02-01 |
Family
ID=49998040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016539899A Ceased JP2017502010A (ja) | 2013-12-20 | 2014-12-19 | 疼痛に対して多重モードの活性を有するピペリジン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9981942B2 (enExample) |
| EP (1) | EP3083601B1 (enExample) |
| JP (1) | JP2017502010A (enExample) |
| CN (1) | CN105849096B (enExample) |
| CA (1) | CA2931051A1 (enExample) |
| MX (1) | MX2016006604A (enExample) |
| WO (1) | WO2015091939A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2018000418A (es) * | 2015-07-29 | 2018-08-14 | Esteve Labor Dr | Derivados de amida que tienen actividad multimodal contra el dolor. |
| JP2018525363A (ja) * | 2015-07-29 | 2018-09-06 | 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置換アミド誘導体 |
| 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 |
| JP7164521B2 (ja) | 2016-06-21 | 2022-11-01 | オリオン・オフサルモロジー・エルエルシー | 炭素環式プロリンアミド誘導体 |
| DK3472149T3 (da) | 2016-06-21 | 2023-11-27 | Orion Ophthalmology LLC | Heterocykliske prolinamidderivater |
| AU2018211057B2 (en) | 2017-01-17 | 2021-12-23 | Mebias Discovery, Inc. | Substituted 3-dialkylaminomethyl-piperidin-4-yl-benzamides and methods of making and using same |
| JP7013048B2 (ja) * | 2018-03-02 | 2022-01-31 | 国立大学法人大阪大学 | タンパク質及び／又はペプチド修飾用分子 |
| TW202304448A (zh) * | 2021-04-07 | 2023-02-01 | 西班牙商塔拉森斯調節公司 | 作為西格瑪配位基的新（高）哌啶基雜環 |
| EP4444305A2 (en) * | 2022-02-16 | 2024-10-16 | Duke Street Bio Limited | Pharmaceutical compound |
| WO2024105225A1 (en) | 2022-11-18 | 2024-05-23 | Universitat De Barcelona | Synergistic combinations of a sigma receptor 1 (s1r) antagonist and a soluble epoxide hydrolase inhibitor (sehi) and their use in the treatment of pain |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL275537A (enExample) * | 1961-03-06 | |||
| DE2109155A1 (en) * | 1971-02-26 | 1972-09-14 | CH. Boehringer Sohn, 6507 Ingelheim | 1-furylmethyl-4-phenyl-4-methoxycarbonylpiperidines - - with analgesic activity anorectic activity salt |
| GB9912410D0 (en) * | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| GB9912411D0 (en) * | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| US6727264B1 (en) * | 2001-07-05 | 2004-04-27 | Synaptic Pharmaceutical Corporation | Substituted anilinic piperidines as MCH selective antagonists |
| EP1411942A4 (en) * | 2001-07-05 | 2005-01-26 | Synaptic Pharma Corp | SUBSTITUTED ANILINPIPERIDINES AS MCH-SELECTIVE ANTAGONISTS |
| US7381721B2 (en) | 2003-03-17 | 2008-06-03 | Adolor Corporation | Substituted piperidine compounds |
| US20070265289A1 (en) | 2004-04-15 | 2007-11-15 | Yoshinori Okamoto | 2-Aminopyrimidine Derivative |
| US7645755B2 (en) * | 2004-10-22 | 2010-01-12 | Janssen Pharmaceutical N.V. | Inhibitors of c-fms kinase |
| EP1917255A2 (en) * | 2005-07-29 | 2008-05-07 | F. Hoffmann-Roche AG | Indol-3-yl-carbonyl-piperidin and piperazin derivatives |
| EP2009005A4 (en) * | 2006-04-19 | 2010-06-02 | Astellas Pharma Inc | AZOLECARBOXAMIDE DERIVATIVE |
| AU2007273057A1 (en) * | 2006-07-12 | 2008-01-17 | Merck Sharp & Dohme Corp. | Substituted pyrazoles as ghrelin receptor antagonists |
| WO2008157844A1 (en) | 2007-06-21 | 2008-12-24 | Forest Laboratories Holdings Limited | Novel piperazine derivatives as inhibitors of stearoyl-coa desaturase |
| ES2465621T3 (es) * | 2007-08-27 | 2014-06-06 | Theravance, Inc. | Compuestos de heteroarilalquil-8-azabiciclo[3.2.1]octano, como antagonistas de los receptores opiodes mu |
| WO2009058801A1 (en) * | 2007-11-02 | 2009-05-07 | Janssen Pharmaceutica, N.V. | Use of cfms inhibitor for treating or preventing bone cancer and the bone loss and bone pain associated with bone cancer |
| WO2010046780A2 (en) | 2008-10-22 | 2010-04-29 | Institut Pasteur Korea | Anti viral compounds |
| EP2375899B1 (en) | 2009-01-12 | 2015-02-25 | Array Biopharma Inc. | Piperidine-containing compounds and use thereof in the treatment of diabetes |
| GB2474748B (en) * | 2009-10-01 | 2011-10-12 | Amira Pharmaceuticals Inc | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
| KR20120140658A (ko) | 2010-02-12 | 2012-12-31 | 파마사이언스 인크. | Ｉａｐ ｂｉｒ 도메인 결합 화합물 |
| EP3083595B1 (en) | 2013-12-20 | 2020-05-27 | Esteve Pharmaceuticals, S.A. | Piperidine compounds having multimodal activity against pain |
-
2014
- 2014-12-19 MX MX2016006604A patent/MX2016006604A/es unknown
- 2014-12-19 CN CN201480070057.7A patent/CN105849096B/zh not_active Expired - Fee Related
- 2014-12-19 CA CA2931051A patent/CA2931051A1/en not_active Abandoned
- 2014-12-19 US US15/106,363 patent/US9981942B2/en not_active Expired - Fee Related
- 2014-12-19 JP JP2016539899A patent/JP2017502010A/ja not_active Ceased
- 2014-12-19 EP EP14824836.2A patent/EP3083601B1/en active Active
- 2014-12-19 WO PCT/EP2014/078717 patent/WO2015091939A1/en not_active Ceased
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