IL122159A - -4 Aril - 1phenylalkyl- 1, 2, 3, 6 - Tetrahydropyridines, their preparation and pharmaceuticals containing - Google Patents
-4 Aril - 1phenylalkyl- 1, 2, 3, 6 - Tetrahydropyridines, their preparation and pharmaceuticals containingInfo
- Publication number
- IL122159A IL122159A IL12215996A IL12215996A IL122159A IL 122159 A IL122159 A IL 122159A IL 12215996 A IL12215996 A IL 12215996A IL 12215996 A IL12215996 A IL 12215996A IL 122159 A IL122159 A IL 122159A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- mixture
- ethyl
- tetrahydropyridine
- mol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- -1 phenoxy, phenylamino Chemical group 0.000 claims abstract description 95
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 21
- 125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 3
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims abstract description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 3
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims abstract description 3
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000005504 styryl group Chemical group 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 101
- 238000000034 method Methods 0.000 claims description 61
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 23
- 230000008569 process Effects 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004465 cycloalkenyloxy group Chemical group 0.000 abstract description 3
- 230000000324 neuroprotective effect Effects 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006529 (C3-C6) alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 266
- 239000000203 mixture Substances 0.000 description 173
- 239000002904 solvent Substances 0.000 description 92
- 239000000047 product Substances 0.000 description 71
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 65
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 62
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 59
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 59
- 229910052938 sodium sulfate Inorganic materials 0.000 description 59
- 235000011152 sodium sulphate Nutrition 0.000 description 59
- 239000012074 organic phase Substances 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000003480 eluent Substances 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 238000004587 chromatography analysis Methods 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
- 239000003921 oil Substances 0.000 description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 18
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
- 239000012047 saturated solution Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 238000004809 thin layer chromatography Methods 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 9
- IFYKRMQORZOMNY-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCNCC=2)=C1 IFYKRMQORZOMNY-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- NMWSKOLWZZWHPL-UHFFFAOYSA-N 3-chlorobiphenyl Chemical group ClC1=CC=CC(C=2C=CC=CC=2)=C1 NMWSKOLWZZWHPL-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000000908 ammonium hydroxide Substances 0.000 description 6
- 229910000085 borane Inorganic materials 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 208000035475 disorder Diseases 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- IYTUKSIOQKTZEG-UHFFFAOYSA-N (3-chloro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C(Cl)=C1 IYTUKSIOQKTZEG-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 4
- HXTFUVWJFLDLJP-UHFFFAOYSA-N ethyl 2-[4-(2-methylpropyl)phenyl]propanoate Chemical compound CCOC(=O)C(C)C1=CC=C(CC(C)C)C=C1 HXTFUVWJFLDLJP-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- CNEWKIDCGDXBDE-UHFFFAOYSA-N 1-[2-(4-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=CC=CC=3)CC=2)=C1 CNEWKIDCGDXBDE-UHFFFAOYSA-N 0.000 description 3
- IZXWIWYERZDWOA-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propan-1-ol Chemical compound CC(C)CC1=CC=C(C(C)CO)C=C1 IZXWIWYERZDWOA-UHFFFAOYSA-N 0.000 description 3
- WALYRZRLDDOTJG-UHFFFAOYSA-N 2-chloro-6-[1-[2-(4-phenylphenyl)ethyl]-3,6-dihydro-2h-pyridin-4-yl]pyridine Chemical compound ClC1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C=CC=CC=3)CC=2)=N1 WALYRZRLDDOTJG-UHFFFAOYSA-N 0.000 description 3
- ILKPZCKFWLTEBQ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(O)CCNCC1 ILKPZCKFWLTEBQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- KXUHSQYYJYAXGZ-UHFFFAOYSA-N isobutylbenzene Chemical compound CC(C)CC1=CC=CC=C1 KXUHSQYYJYAXGZ-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- DKYRKAIKWFHQHM-UHFFFAOYSA-N (3,5-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=CC(Cl)=C1 DKYRKAIKWFHQHM-UHFFFAOYSA-N 0.000 description 2
- 125000006532 (C3-C5) alkyl group Chemical group 0.000 description 2
- VMHAYKUZIAAXIZ-UHFFFAOYSA-N 1,2-bis(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=CC=C1CC(C)C VMHAYKUZIAAXIZ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IARQHEORJGJTSH-UHFFFAOYSA-N 1-(2-bromoethyl)-4-(2-methylpropyl)benzene Chemical compound CC(C)CC1=CC=C(CCBr)C=C1 IARQHEORJGJTSH-UHFFFAOYSA-N 0.000 description 2
- IDGZWZOGXPFMAL-UHFFFAOYSA-N 1-(2-bromoethyl)-4-phenylbenzene Chemical group C1=CC(CCBr)=CC=C1C1=CC=CC=C1 IDGZWZOGXPFMAL-UHFFFAOYSA-N 0.000 description 2
- DRUFLWBKCQQARQ-UHFFFAOYSA-N 1-[2-(2-methoxy-5-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound COC1=CC=C(C=2C=CC=CC=2)C=C1CCN(CC=1)CCC=1C1=CC=CC(C(F)(F)F)=C1 DRUFLWBKCQQARQ-UHFFFAOYSA-N 0.000 description 2
- GEXQHZWNQSNYMQ-UHFFFAOYSA-N 1-[2-(3-phenylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-pyridine hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C(C=CC=3)C=3C=CC=CC=3)CC=2)=C1 GEXQHZWNQSNYMQ-UHFFFAOYSA-N 0.000 description 2
- PXDPEQSARDZRSU-UHFFFAOYSA-N 1-[2-[4-(2-chlorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=CC(=CC=3)C=3C(=CC=CC=3)Cl)CC=2)=C1 PXDPEQSARDZRSU-UHFFFAOYSA-N 0.000 description 2
- CPNHRQSEIFVLQO-UHFFFAOYSA-N 1-[2-[4-(4-fluorophenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(F)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 CPNHRQSEIFVLQO-UHFFFAOYSA-N 0.000 description 2
- KRZBYJLACJFLEQ-UHFFFAOYSA-N 1-[2-[4-(4-methoxyphenyl)phenyl]ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(OC)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 KRZBYJLACJFLEQ-UHFFFAOYSA-N 0.000 description 2
- RWXUNIMBRXGNEP-UHFFFAOYSA-N 1-bromo-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Br RWXUNIMBRXGNEP-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- MDTAULLCKGQYMK-UHFFFAOYSA-N 2-(2-chloro-4-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1Cl MDTAULLCKGQYMK-UHFFFAOYSA-N 0.000 description 2
- KINVBFAPQYQPTG-UHFFFAOYSA-N 2-(2-chloro-4-methoxyphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C(Cl)=C1 KINVBFAPQYQPTG-UHFFFAOYSA-N 0.000 description 2
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- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
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- FOQCNUUYQWIJPZ-UHFFFAOYSA-N ethyl 2-(3-chloro-4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C(Cl)=C1 FOQCNUUYQWIJPZ-UHFFFAOYSA-N 0.000 description 1
- XTSCLIBGCPXCLH-UHFFFAOYSA-N ethyl 2-(4-bromophenyl)-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)C1=CC=C(Br)C=C1 XTSCLIBGCPXCLH-UHFFFAOYSA-N 0.000 description 1
- JQSMDZBMTWENSF-UHFFFAOYSA-N ethyl 4-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenoxy]butanoate Chemical compound C1=CC(OCCCC(=O)OCC)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 JQSMDZBMTWENSF-UHFFFAOYSA-N 0.000 description 1
- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 1
- LKGFRTZVCPEBMJ-UHFFFAOYSA-N ethyl 5-[4-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]phenoxy]pentanoate Chemical compound C1=CC(OCCCCC(=O)OCC)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 LKGFRTZVCPEBMJ-UHFFFAOYSA-N 0.000 description 1
- DYFCEXPYPIZOOI-UHFFFAOYSA-N ethyl 5-[4-[4-[2-[4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridin-1-yl]ethyl]phenyl]phenoxy]pentanoate;hydrochloride Chemical compound Cl.C1=CC(OCCCCC(=O)OCC)=CC=C1C(C=C1)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 DYFCEXPYPIZOOI-UHFFFAOYSA-N 0.000 description 1
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- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
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- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000002161 motor neuron Anatomy 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002664 nootropic agent Substances 0.000 description 1
- 230000001777 nootropic effect Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229960004526 piracetam Drugs 0.000 description 1
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000002739 subcortical effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000012581 transferrin Substances 0.000 description 1
- UEKQSLXYFDHEJR-UHFFFAOYSA-N tributylstannane;hydrochloride Chemical compound Cl.CCCC[SnH](CCCC)CCCC UEKQSLXYFDHEJR-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- WJJYZXPHLSLMGE-UHFFFAOYSA-N xaliproden Chemical compound FC(F)(F)C1=CC=CC(C=2CCN(CCC=3C=C4C=CC=CC4=CC=3)CC=2)=C1 WJJYZXPHLSLMGE-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9507760A FR2736053B1 (fr) | 1995-06-28 | 1995-06-28 | Nouvelles 1-phenylalkyl-1,2,3,6-tetrahydropyridines |
| PCT/FR1996/000995 WO1997001536A1 (fr) | 1995-06-28 | 1996-06-26 | 4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines ayant une activite neurotrophique et neuroprotectrice |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL122159A0 IL122159A0 (en) | 1998-04-05 |
| IL122159A true IL122159A (en) | 2001-06-14 |
Family
ID=9480466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL12215996A IL122159A (en) | 1995-06-28 | 1996-06-26 | -4 Aril - 1phenylalkyl- 1, 2, 3, 6 - Tetrahydropyridines, their preparation and pharmaceuticals containing |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5981754A (cs) |
| EP (2) | EP0837848B1 (cs) |
| JP (2) | JP3147906B2 (cs) |
| KR (1) | KR100460581B1 (cs) |
| CN (1) | CN1153765C (cs) |
| AT (1) | ATE223897T1 (cs) |
| AU (1) | AU715090B2 (cs) |
| BR (1) | BR9608662A (cs) |
| CA (1) | CA2225746C (cs) |
| CY (1) | CY2312B1 (cs) |
| CZ (1) | CZ291075B6 (cs) |
| DE (1) | DE69623631T2 (cs) |
| DK (1) | DK0837848T3 (cs) |
| EE (1) | EE03870B1 (cs) |
| ES (1) | ES2183965T3 (cs) |
| FR (1) | FR2736053B1 (cs) |
| HK (1) | HK1014952A1 (cs) |
| HU (1) | HUP9900055A3 (cs) |
| IL (1) | IL122159A (cs) |
| IS (1) | IS1999B (cs) |
| NO (1) | NO310144B1 (cs) |
| NZ (1) | NZ312723A (cs) |
| PL (2) | PL192353B1 (cs) |
| PT (1) | PT837848E (cs) |
| RU (1) | RU2163237C2 (cs) |
| SK (2) | SK283707B6 (cs) |
| TR (1) | TR199701710T1 (cs) |
| UA (1) | UA62914C2 (cs) |
| WO (1) | WO1997001536A1 (cs) |
| ZA (1) | ZA965527B (cs) |
Families Citing this family (36)
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| FR2762514B1 (fr) * | 1997-04-29 | 1999-10-22 | Sanofi Sa | Utilisation de derives de la tetrahydropyridine pour la preparation de medicaments pour le traitement des maladies entrainant une demyelinisation |
| FR2763847B1 (fr) | 1997-05-28 | 2003-06-06 | Sanofi Sa | Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta-1 |
| FR2771006B1 (fr) * | 1997-11-14 | 2000-12-01 | Sanofi Sa | Association de principes actifs pour le traitement de la demence senile du type alzheimer |
| FR2771007B1 (fr) * | 1997-11-14 | 2000-12-01 | Sanofi Sa | Association de principes actifs pour le traitement de la demence senile du type alzheimer |
| CO4980891A1 (es) * | 1997-11-14 | 2000-11-27 | Sanofi Sa | Asociacion de principios activos para el tratamiento de la demencia senil de tipo azheimer |
| WO1999065896A1 (en) * | 1998-06-19 | 1999-12-23 | Eli Lilly And Company | Preparation of heteroaryl compounds |
| FR2803593B1 (fr) * | 2000-01-06 | 2002-02-15 | Sanofi Synthelabo | Nouvelles tetrahydropyridines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| ATE365162T1 (de) | 2001-04-20 | 2007-07-15 | Sanofi Aventis | Tetrahydropyridyl-alkyl-heterozykle, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen die sie enthalten |
| FR2823748B1 (fr) * | 2001-04-20 | 2004-02-20 | Sanofi Synthelabo | Tetrahydropyridyl-alkyl-benzodiazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2840896B1 (fr) * | 2002-06-18 | 2005-04-08 | Sanofi Synthelabo | Phenyl-et pyridyl-piperazines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| EA009027B1 (ru) * | 2002-12-16 | 2007-10-26 | Мицубиси Фарма Корпорейшн | Производные 3-замещенного-4-пиримидона |
| EP1657240A4 (en) | 2003-08-18 | 2009-04-08 | Fujifilm Finechemicals Co Ltd | PYRIDYLTETRAHYDROPYRIDINE, PYRIDYLPIPERIDINE AND METHOD FOR THE PRODUCTION THEREOF |
| TWI350168B (en) * | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| EA200700118A1 (ru) * | 2004-06-24 | 2007-08-31 | Инсайт Корпорейшн | Амидосоединения и их применение в качестве лекарственных средств |
| CA2584502A1 (en) * | 2004-06-24 | 2006-01-05 | Incyte Corporation | 2-methylpropanamides and their use as pharmaceuticals |
| EP1758882A4 (en) * | 2004-06-24 | 2008-01-23 | Incyte Corp | AMID COMPOUNDS AND THEIR USE AS MEDICAMENTS |
| US20060009491A1 (en) * | 2004-06-24 | 2006-01-12 | Incyte Corporation | Amido compounds and their use as pharmaceuticals |
| EP1758580A4 (en) | 2004-06-24 | 2008-01-16 | Incyte Corp | N-SUBSTITUTED PIPERIDINE AND ITS USE AS A MEDICAMENT |
| US20060122197A1 (en) * | 2004-08-10 | 2006-06-08 | Wenqing Yao | Amido compounds and their use as pharmaceuticals |
| GEP20125565B (en) * | 2004-11-10 | 2012-07-10 | Incyte Corp | Lactam compounds and their pharmaceutical use |
| US8110581B2 (en) | 2004-11-10 | 2012-02-07 | Incyte Corporation | Lactam compounds and their use as pharmaceuticals |
| CA2587153A1 (en) * | 2004-11-18 | 2006-05-26 | Incyte Corporation | Inhibitors of 11-.beta. hydroxyl steroid dehydrogenase type 1 and methods of using the same |
| FR2883285B1 (fr) * | 2005-03-17 | 2007-05-18 | Sanofi Aventis Sa | Sel besylate de la 7-(2-(4-(3-trifluoromethyl-phenyl) -1,2,3,6-tetrahudro-pyrid-1-yl)ethyl) isoquinoleine, sa preparation et son utilisation en therapeutique |
| JP4864342B2 (ja) * | 2005-04-27 | 2012-02-01 | 北興化学工業株式会社 | ビアリール化合物の製造方法 |
| US20070066584A1 (en) * | 2005-09-21 | 2007-03-22 | Wenqing Yao | Amido compounds and their use as pharmaceuticals |
| BRPI0619446A2 (pt) * | 2005-12-05 | 2011-10-04 | Incyte Corp | compostos de lactama, suas composições e método de modulação da atividade de 11bhsd1 |
| WO2007084314A2 (en) * | 2006-01-12 | 2007-07-26 | Incyte Corporation | MODULATORS OF 11-ß HYDROXYL STEROID DEHYDROGENASE TYPE 1, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USING THE SAME |
| BRPI0707408A2 (pt) * | 2006-01-31 | 2011-05-03 | Incyte Corp | compostos de amido e seu uso como produtos farmacêuticos |
| WO2007101270A1 (en) * | 2006-03-02 | 2007-09-07 | Incyte Corporation | MODULATORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE 1, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USING THE SAME |
| US20070208001A1 (en) * | 2006-03-03 | 2007-09-06 | Jincong Zhuo | Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| US20070293529A1 (en) * | 2006-05-01 | 2007-12-20 | Yun-Long Li | Tetrasubstituted ureas as modulators of 11-beta hydroxyl steroid dehydrogenase type 1 |
| WO2007137066A2 (en) * | 2006-05-17 | 2007-11-29 | Incyte Corporation | HETEROCYCLIC INHIBITORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE I AND METHODS OF USING THE SAME |
| CL2008001839A1 (es) * | 2007-06-21 | 2009-01-16 | Incyte Holdings Corp | Compuestos derivados de 2,7-diazaespirociclos, inhibidores de 11-beta hidroxil esteroide deshidrogenasa tipo 1; composicion farmaceutica que comprende a dichos compuestos; utiles para tratar la obesidad, diabetes, intolerancia a la glucosa, diabetes tipo ii, entre otras enfermedades. |
| KR20100135711A (ko) | 2007-12-20 | 2010-12-27 | 엔비보 파마슈티칼즈, 인코퍼레이티드 | 사중치환된 벤젠 |
| JP5899119B2 (ja) * | 2010-01-19 | 2016-04-06 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | アリール酢酸誘導体及びヘテロアリール酢酸誘導体を製造する方法 |
| US10858351B2 (en) | 2017-04-26 | 2020-12-08 | Alberta Research Chemicals Inc. | Substituted tetrahydropyridine derivatives as IDO-1 inhibitors and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2098248T3 (es) * | 1989-05-17 | 1997-05-01 | Pfizer | Derivados de 2-piperidino-1-alcanoles como agentes antiisquemicos. |
| FR2650505B1 (fr) * | 1989-08-07 | 1994-06-03 | Midy Spa | Utilisation de trifluoromethylphenyltetrahydropyridines pour la preparation de medicaments destines a combattre les troubles de la motricite intestinale |
| FR2662355B1 (fr) * | 1990-05-22 | 1994-11-10 | Sanofi Sa | Utilisation de la 1-[2-(2-naphtyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine pour la preparation de medicaments destines au traitement de troubles cerebraux et neuronaux. |
| HU211019B (en) * | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
| DE4325855A1 (de) * | 1993-08-02 | 1995-02-09 | Boehringer Ingelheim Kg | Neue Benzoesäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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1995
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1996
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- 1996-06-26 WO PCT/FR1996/000995 patent/WO1997001536A1/fr active IP Right Grant
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1997
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