CA2133984A1 - N-aryloxy(thio)alkyl-azacycloalcanes utiles comme antagonistes des canaux calciques - Google Patents
N-aryloxy(thio)alkyl-azacycloalcanes utiles comme antagonistes des canaux calciquesInfo
- Publication number
- CA2133984A1 CA2133984A1 CA002133984A CA2133984A CA2133984A1 CA 2133984 A1 CA2133984 A1 CA 2133984A1 CA 002133984 A CA002133984 A CA 002133984A CA 2133984 A CA2133984 A CA 2133984A CA 2133984 A1 CA2133984 A1 CA 2133984A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- piperidinoheptane
- compound
- benzyloxyphenoxy
- phenoxy
- 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.)
- Abandoned
Links
- 229940127291 Calcium channel antagonist Drugs 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 239000003814 drug Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000005864 Sulphur Chemical group 0.000 claims abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
- -1 phenoxy, benzyl Chemical group 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 239000011575 calcium Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 4
- 210000004958 brain cell Anatomy 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims 4
- 238000006722 reduction reaction Methods 0.000 claims 3
- LSQKLHWGHCMRKP-UHFFFAOYSA-N 1-(7-dibenzofuran-2-yloxyheptyl)piperidine Chemical compound C=1C=C2OC3=CC=CC=C3C2=CC=1OCCCCCCCN1CCCCC1 LSQKLHWGHCMRKP-UHFFFAOYSA-N 0.000 claims 2
- YIBXXBUKEIUFOL-UHFFFAOYSA-N 1-(7-phenoxyheptyl)piperidine Chemical compound C1CCCCN1CCCCCCCOC1=CC=CC=C1 YIBXXBUKEIUFOL-UHFFFAOYSA-N 0.000 claims 2
- BKSUQYCRJROASG-UHFFFAOYSA-N 1-[5-(4-phenylmethoxyphenoxy)pentyl]piperidine Chemical compound C1CCCCN1CCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 BKSUQYCRJROASG-UHFFFAOYSA-N 0.000 claims 2
- QVFSRJUBPRWJNS-UHFFFAOYSA-N 1-[7-(2,4-dichlorophenoxy)heptyl]piperidine Chemical compound ClC1=CC(Cl)=CC=C1OCCCCCCCN1CCCCC1 QVFSRJUBPRWJNS-UHFFFAOYSA-N 0.000 claims 2
- XMYSNIWLWWAISN-UHFFFAOYSA-N 1-[7-(2-benzylphenoxy)heptyl]piperidine Chemical compound C1CCCCN1CCCCCCCOC1=CC=CC=C1CC1=CC=CC=C1 XMYSNIWLWWAISN-UHFFFAOYSA-N 0.000 claims 2
- CLIKOSBXQSDHSP-UHFFFAOYSA-N 1-[7-(3-phenoxyphenoxy)heptyl]piperidine Chemical compound C1CCCCN1CCCCCCCOC(C=1)=CC=CC=1OC1=CC=CC=C1 CLIKOSBXQSDHSP-UHFFFAOYSA-N 0.000 claims 2
- PLBFAWQXTZPNHH-UHFFFAOYSA-N 1-[7-(4-benzylphenoxy)heptyl]piperidine Chemical compound C1CCCCN1CCCCCCCOC(C=C1)=CC=C1CC1=CC=CC=C1 PLBFAWQXTZPNHH-UHFFFAOYSA-N 0.000 claims 2
- FWSPLUYVMGSWJI-UHFFFAOYSA-N 1-[7-(4-fluorophenoxy)heptyl]piperidine Chemical compound C1=CC(F)=CC=C1OCCCCCCCN1CCCCC1 FWSPLUYVMGSWJI-UHFFFAOYSA-N 0.000 claims 2
- YUKDYBMKSQMTMY-UHFFFAOYSA-N 1-[7-(4-methoxyphenoxy)heptyl]piperidine Chemical compound C1=CC(OC)=CC=C1OCCCCCCCN1CCCCC1 YUKDYBMKSQMTMY-UHFFFAOYSA-N 0.000 claims 2
- VMGKCIIZGDHHKN-UHFFFAOYSA-N 1-[7-(4-phenylmethoxyphenoxy)heptyl]azepane Chemical compound C1CCCCCN1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 VMGKCIIZGDHHKN-UHFFFAOYSA-N 0.000 claims 2
- RUUQQYYBMMZSNJ-UHFFFAOYSA-N 1-[7-(4-phenylmethoxyphenoxy)heptyl]piperidine Chemical compound C1CCCCN1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 RUUQQYYBMMZSNJ-UHFFFAOYSA-N 0.000 claims 2
- IEYWJLFYRFFDHX-UHFFFAOYSA-N 1-[7-(4-phenylmethoxyphenoxy)heptyl]pyrrolidine Chemical compound C1CCCN1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 IEYWJLFYRFFDHX-UHFFFAOYSA-N 0.000 claims 2
- LRSRBFLNCDGSSM-UHFFFAOYSA-N 1-[7-(4-tert-butylphenoxy)heptyl]piperidine Chemical compound C1=CC(C(C)(C)C)=CC=C1OCCCCCCCN1CCCCC1 LRSRBFLNCDGSSM-UHFFFAOYSA-N 0.000 claims 2
- MAFADRUQOFLNMM-UHFFFAOYSA-N 1-[7-[4-[(4-fluorophenyl)methoxy]phenoxy]heptyl]piperidine Chemical compound C1=CC(F)=CC=C1COC(C=C1)=CC=C1OCCCCCCCN1CCCCC1 MAFADRUQOFLNMM-UHFFFAOYSA-N 0.000 claims 2
- IWAULUGAJGNVTN-UHFFFAOYSA-N 1-[7-[4-[(4-methoxyphenyl)methoxy]phenoxy]heptyl]piperidine Chemical compound C1=CC(OC)=CC=C1COC(C=C1)=CC=C1OCCCCCCCN1CCCCC1 IWAULUGAJGNVTN-UHFFFAOYSA-N 0.000 claims 2
- CVNCGCRVLCSRCV-CCEZHUSRSA-N 1-[7-[4-[(e)-2-phenylethenyl]phenoxy]heptyl]piperidine Chemical compound C1CCCCN1CCCCCCCOC(C=C1)=CC=C1\C=C\C1=CC=CC=C1 CVNCGCRVLCSRCV-CCEZHUSRSA-N 0.000 claims 2
- IKRVARMBENOSFS-UHFFFAOYSA-N 1-[7-[4-[2-(4-chlorophenyl)ethyl]phenoxy]heptyl]piperidine Chemical compound C1=CC(Cl)=CC=C1CCC(C=C1)=CC=C1OCCCCCCCN1CCCCC1 IKRVARMBENOSFS-UHFFFAOYSA-N 0.000 claims 2
- GPNZHMVBQLHVFK-UHFFFAOYSA-N 1-[8-(4-phenylmethoxyphenoxy)octyl]piperidine Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1OCCCCCCCCN1CCCCC1 GPNZHMVBQLHVFK-UHFFFAOYSA-N 0.000 claims 2
- SYDZPXRKIGDZDX-UHFFFAOYSA-N 2,6-dimethyl-1-[7-(4-phenylmethoxyphenoxy)heptyl]piperidine Chemical compound CC1CCCC(C)N1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 SYDZPXRKIGDZDX-UHFFFAOYSA-N 0.000 claims 2
- MJQLSJJYJLWZPJ-UHFFFAOYSA-N 2-methyl-1-[7-(4-phenylmethoxyphenoxy)heptyl]piperidine Chemical compound CC1CCCCN1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 MJQLSJJYJLWZPJ-UHFFFAOYSA-N 0.000 claims 2
- TYDKQZLNRBEYFR-UHFFFAOYSA-N 4-methoxy-1-[7-(4-phenylmethoxyphenoxy)heptyl]piperidine Chemical compound C1CC(OC)CCN1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 TYDKQZLNRBEYFR-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- JMJMXDWDHMUSGD-UHFFFAOYSA-N 1-[6-(3,4-dichlorophenoxy)hexyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1OCCCCCCN1CCCCC1 JMJMXDWDHMUSGD-UHFFFAOYSA-N 0.000 claims 1
- PIOOGWBWNMQWLQ-UHFFFAOYSA-N 1-[6-(4-phenylmethoxyphenoxy)hexyl]piperidine Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1OCCCCCCN1CCCCC1 PIOOGWBWNMQWLQ-UHFFFAOYSA-N 0.000 claims 1
- UECCEOBDBRSUIF-UHFFFAOYSA-N 1-[7-(1,3-benzodioxol-5-yloxy)heptyl]piperidine Chemical compound C=1C=C2OCOC2=CC=1OCCCCCCCN1CCCCC1 UECCEOBDBRSUIF-UHFFFAOYSA-N 0.000 claims 1
- BPHLVILJVXPBTG-UHFFFAOYSA-N 1-[7-(3,4-dichlorophenoxy)heptyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1OCCCCCCCN1CCCCC1 BPHLVILJVXPBTG-UHFFFAOYSA-N 0.000 claims 1
- YKVLISJFQMXYSC-UHFFFAOYSA-N 1-[7-(4-phenoxyphenoxy)heptyl]piperidine Chemical compound C1CCCCN1CCCCCCCOC(C=C1)=CC=C1OC1=CC=CC=C1 YKVLISJFQMXYSC-UHFFFAOYSA-N 0.000 claims 1
- BHJPOGXVKOFPIU-UHFFFAOYSA-N 1-[7-[4-(2-phenylethyl)phenoxy]heptyl]piperidine Chemical compound C1CCCCN1CCCCCCCOC(C=C1)=CC=C1CCC1=CC=CC=C1 BHJPOGXVKOFPIU-UHFFFAOYSA-N 0.000 claims 1
- POGYCCYUHNVZNL-UHFFFAOYSA-N 1-[7-[4-[(3,4-dichlorophenyl)methoxy]phenoxy]heptyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1COC(C=C1)=CC=C1OCCCCCCCN1CCCCC1 POGYCCYUHNVZNL-UHFFFAOYSA-N 0.000 claims 1
- ZIUGYMYHAIAIRF-UHFFFAOYSA-N 1-[8-(4-phenoxyphenoxy)octyl]piperidine Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1OCCCCCCCCN1CCCCC1 ZIUGYMYHAIAIRF-UHFFFAOYSA-N 0.000 claims 1
- ARDHGFUPBDFNKH-UHFFFAOYSA-N 1-[9-(3,4-dichlorophenoxy)nonyl]piperidine Chemical compound C1=C(Cl)C(Cl)=CC=C1OCCCCCCCCCN1CCCCC1 ARDHGFUPBDFNKH-UHFFFAOYSA-N 0.000 claims 1
- YNSBJKKVBLTXEP-UHFFFAOYSA-N 1-[9-(4-phenylmethoxyphenoxy)nonyl]piperidine Chemical compound C1CCCCN1CCCCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 YNSBJKKVBLTXEP-UHFFFAOYSA-N 0.000 claims 1
- SVCMKZQYDKUKGX-UHFFFAOYSA-N 3-methyl-1-[7-(4-phenylmethoxyphenoxy)heptyl]piperidine Chemical compound C1C(C)CCCN1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 SVCMKZQYDKUKGX-UHFFFAOYSA-N 0.000 claims 1
- FVIQPBRUGUTXKB-UHFFFAOYSA-N 4-methyl-1-[7-(4-phenylmethoxyphenoxy)heptyl]piperidine Chemical compound C1CC(C)CCN1CCCCCCCOC(C=C1)=CC=C1OCC1=CC=CC=C1 FVIQPBRUGUTXKB-UHFFFAOYSA-N 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 239000000480 calcium channel blocker Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 235000002639 sodium chloride Nutrition 0.000 description 13
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 241000009298 Trigla lyra Species 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 229910021653 sulphate ion Inorganic materials 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 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 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 4
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- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 4
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N niclosamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+]([O-])=O)C=C1Cl RJMUSRYZPJIFPJ-UHFFFAOYSA-N 0.000 description 3
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- 229940032147 starch Drugs 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9208859.0 | 1992-04-24 | ||
| GB929208871A GB9208871D0 (en) | 1992-04-24 | 1992-04-24 | Compounds |
| GB929208859A GB9208859D0 (en) | 1992-04-24 | 1992-04-24 | Compounds |
| GB9208871.5 | 1992-04-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2133984A1 true CA2133984A1 (fr) | 1993-11-11 |
Family
ID=26300767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002133984A Abandoned CA2133984A1 (fr) | 1992-04-24 | 1993-04-15 | N-aryloxy(thio)alkyl-azacycloalcanes utiles comme antagonistes des canaux calciques |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0637303A1 (fr) |
| JP (1) | JPH07506104A (fr) |
| KR (1) | KR950701330A (fr) |
| CN (1) | CN1083055A (fr) |
| AU (1) | AU3959893A (fr) |
| CA (1) | CA2133984A1 (fr) |
| IL (1) | IL105495A0 (fr) |
| MA (1) | MA22880A1 (fr) |
| SI (1) | SI9300217A (fr) |
| WO (1) | WO1993022302A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9321811D0 (en) * | 1993-10-22 | 1993-12-15 | Smithkline Beecham Plc | Pharmaceuticals |
| KR100533431B1 (ko) * | 1995-01-23 | 2006-05-03 | 다이이치 아스비오파마 가부시키가이샤 | 허혈성질환에기인하는증상의완화또는치료용약제및이에유용한화합물 |
| US5794887A (en) | 1995-11-17 | 1998-08-18 | Komerath; Narayanan M. | Stagnation point vortex controller |
| AU1600599A (en) | 1998-02-27 | 1999-09-15 | Warner-Lambert Company | Heterocyclic substituted aniline calcium channel blockers |
| US6166052A (en) | 1998-03-11 | 2000-12-26 | Warner-Lambert Company | Heteroaryl alkyl alpha substituted peptidylamine calcium channel blockers |
| US7417040B2 (en) | 2004-03-01 | 2008-08-26 | Bristol-Myers Squibb Company | Fused tricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
| US12162851B2 (en) * | 2020-03-11 | 2024-12-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| WO2025188837A1 (fr) * | 2024-03-06 | 2025-09-12 | Nocion Therapeutics, Inc. | Bloqueurs de canaux ioniques chargés et procédés d'utilisation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1299247A (en) * | 1970-06-22 | 1972-12-13 | Labaz | Benzofuran derivatives and process for preparing the same |
| GB2078217B (en) * | 1980-06-14 | 1984-01-11 | Beecham Group Ltd | Phenolic ethers their preparation and use |
| AU9145782A (en) * | 1981-12-14 | 1983-06-23 | Syntex (U.S.A.) Inc. | Naphthoxy ackylamines and related compounds |
| US4851423A (en) * | 1986-12-10 | 1989-07-25 | Schering Corporation | Pharmaceutically active compounds |
| DE3706585A1 (de) * | 1987-02-25 | 1988-09-08 | Schering Ag | Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung |
| CA2020888A1 (fr) * | 1989-07-27 | 1991-01-28 | Philippe Guerry | Derives d'aminoalkoxybenzene substitues |
| TW199153B (fr) * | 1990-08-07 | 1993-02-01 | Dtsuka Seiyaku Kk |
-
1993
- 1993-04-15 KR KR1019940703826A patent/KR950701330A/ko not_active Withdrawn
- 1993-04-15 JP JP5519026A patent/JPH07506104A/ja active Pending
- 1993-04-15 EP EP93909052A patent/EP0637303A1/fr not_active Withdrawn
- 1993-04-15 AU AU39598/93A patent/AU3959893A/en not_active Abandoned
- 1993-04-15 CA CA002133984A patent/CA2133984A1/fr not_active Abandoned
- 1993-04-15 WO PCT/GB1993/000801 patent/WO1993022302A1/fr not_active Ceased
- 1993-04-22 IL IL105495A patent/IL105495A0/xx unknown
- 1993-04-22 MA MA23173A patent/MA22880A1/fr unknown
- 1993-04-23 SI SI9300217A patent/SI9300217A/sl unknown
- 1993-04-23 CN CN93106361A patent/CN1083055A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR950701330A (ko) | 1995-03-23 |
| SI9300217A (sl) | 1993-12-31 |
| JPH07506104A (ja) | 1995-07-06 |
| WO1993022302A1 (fr) | 1993-11-11 |
| EP0637303A1 (fr) | 1995-02-08 |
| AU3959893A (en) | 1993-11-29 |
| CN1083055A (zh) | 1994-03-02 |
| IL105495A0 (en) | 1993-08-18 |
| MA22880A1 (fr) | 1993-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |