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 containing

Info

Publication number: IL122159A
Authority: IL; Israel
Prior art keywords: alkyl; mixture; ethyl; tetrahydropyridine; mol
Prior art date: 1995-06-28

Application number

IL12215996A

Other languages

English (en)

Hebrew (he)

Other versions

IL122159A0 (en

Original Assignee

Sanofi Synthelabo

Priority date (The priority date 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 date listed.)

1995-06-28

Filing date

1996-06-26

Publication date

2001-06-14

1996-06-26 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

1998-04-05 Publication of IL122159A0 publication Critical patent/IL122159A0/xx

2001-06-14 Publication of IL122159A publication Critical patent/IL122159A/en

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
PMOSJSPFNDUAFY-UHFFFAOYSA-N 2-(4-bromophenyl)ethanol Chemical compound OCCC1=CC=C(Br)C=C1 PMOSJSPFNDUAFY-UHFFFAOYSA-N 0.000 description 2
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125000004432 carbon atom Chemical group C* 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000000718 cholinopositive effect Effects 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000006599 edta-medium Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
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
125000004494 ethyl ester group Chemical group 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
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
229960002390 flurbiprofen Drugs 0.000 description 1
230000006870 function Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
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
229960002216 methylparaben Drugs 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
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)
Neurology (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)
Neurosurgery (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)

IL12215996A 1995-06-28 1996-06-26 -4 Aril - 1phenylalkyl- 1, 2, 3, 6 - Tetrahydropyridines, their preparation and pharmaceuticals containing IL122159A (en)

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 (29)

Country	Link
US (1)	US5981754A (de)
EP (2)	EP0837848B1 (de)
JP (2)	JP3147906B2 (de)
KR (1)	KR100460581B1 (de)
CN (1)	CN1153765C (de)
AT (1)	ATE223897T1 (de)
AU (1)	AU715090B2 (de)
BR (1)	BR9608662A (de)
CA (1)	CA2225746C (de)
CY (1)	CY2312B1 (de)
CZ (1)	CZ291075B6 (de)
DE (1)	DE69623631T2 (de)
DK (1)	DK0837848T3 (de)
EE (1)	EE03870B1 (de)
ES (1)	ES2183965T3 (de)
FR (1)	FR2736053B1 (de)
HU (1)	HUP9900055A3 (de)
IL (1)	IL122159A (de)
IS (1)	IS1999B (de)
NO (1)	NO310144B1 (de)
NZ (1)	NZ312723A (de)
PL (2)	PL187087B1 (de)
PT (1)	PT837848E (de)
RU (1)	RU2163237C2 (de)
SK (2)	SK283707B6 (de)
TR (1)	TR199701710T1 (de)
UA (1)	UA62914C2 (de)
WO (1)	WO1997001536A1 (de)
ZA (1)	ZA965527B (de)

Families Citing this family (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
CO4980891A1 (es) *	1997-11-14	2000-11-27	Sanofi Sa	Asociacion de principios activos para el tratamiento de la demencia senil de tipo azheimer
FR2771007B1 (fr) *	1997-11-14	2000-12-01	Sanofi Sa	Association de principes actifs pour le traitement de la demence senile du type alzheimer
FR2771006B1 (fr) *	1997-11-14	2000-12-01	Sanofi Sa	Association de principes actifs pour le traitement de la demence senile du type alzheimer
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
FR2823748B1 (fr) *	2001-04-20	2004-02-20	Sanofi Synthelabo	Tetrahydropyridyl-alkyl-benzodiazines, procede pour leur preparation et compositions pharmaceutiques les contenant
EP1383762B1 (de)	2001-04-20	2007-06-20	Sanofi-Aventis	Tetrahydropyridyl-alkyl-heterozykle, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen die sie enthalten
FR2840896B1 (fr) *	2002-06-18	2005-04-08	Sanofi Synthelabo	Phenyl-et pyridyl-piperazines, procede pour leur preparation et compositions pharmaceutiques les contenant
JP4616003B2 (ja) *	2002-12-16	2011-01-19	田辺三菱製薬株式会社	３−置換−４−ピリミドン誘導体
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1995
- 1995-06-28 FR FR9507760A patent/FR2736053B1/fr not_active Expired - Fee Related
1996
- 1996-06-26 EP EP96924023A patent/EP0837848B1/de not_active Expired - Lifetime
- 1996-06-26 PL PL96324216A patent/PL187087B1/pl not_active IP Right Cessation
- 1996-06-26 KR KR1019970709747A patent/KR100460581B1/ko not_active Expired - Fee Related
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- 1996-06-26 EP EP02006482A patent/EP1216996A3/de not_active Withdrawn
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1997
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2000
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Also Published As

Publication number	Publication date
JPH11506118A (ja)	1999-06-02
ES2183965T3 (es)	2003-04-01
KR19990028431A (ko)	1999-04-15
PL192353B1 (pl)	2006-10-31
IL122159A0 (en)	1998-04-05
HK1014952A1 (en)	1999-10-08
IS4641A (is)	1997-12-23
NO310144B1 (no)	2001-05-28
SK283707B6 (sk)	2003-12-02
AU715090B2 (en)	2000-01-13
PL187087B1 (pl)	2004-05-31
CA2225746C (en)	2004-05-18
CN1189154A (zh)	1998-07-29
NO976079L (no)	1997-12-23
CZ422297A3 (cs)	1998-04-15
SK178197A3 (en)	1998-07-08
RU2163237C2 (ru)	2001-02-20
CN1153765C (zh)	2004-06-16
EE03870B1 (et)	2002-10-15
DK0837848T3 (da)	2003-01-06
MX9710472A (es)	1998-03-31
CA2225746A1 (en)	1997-01-16
IS1999B (is)	2005-04-15
HUP9900055A2 (hu)	1999-04-28
CZ291075B6 (cs)	2002-12-11
DE69623631T2 (de)	2003-08-07
ZA965527B (en)	1997-01-24
EP1216996A3 (de)	2003-10-15
WO1997001536A1 (fr)	1997-01-16
EE9700348A (et)	1998-06-15
CY2312B1 (en)	2003-11-14
PL324216A1 (en)	1998-05-11
JP3147906B2 (ja)	2001-03-19
ATE223897T1 (de)	2002-09-15
NZ312723A (en)	1999-10-28
TR199701710T1 (xx)	1998-05-21
KR100460581B1 (ko)	2005-04-14
JP2001114763A (ja)	2001-04-24
DE69623631D1 (en)	2002-10-17
SK285433B6 (sk)	2007-01-04
EP0837848A1 (de)	1998-04-29
EP1216996A2 (de)	2002-06-26
NO976079D0 (no)	1997-12-23
HUP9900055A3 (en)	1999-11-29
EP0837848B1 (de)	2002-09-11
AU6461996A (en)	1997-01-30
BR9608662A (pt)	1999-05-04
JP3302351B2 (ja)	2002-07-15
UA62914C2 (en)	2004-01-15
FR2736053A1 (fr)	1997-01-03
US5981754A (en)	1999-11-09
FR2736053B1 (fr)	1997-09-19
PT837848E (pt)	2002-12-31

Legal Events

Date	Code	Title
2001-11-25	FF	Patent granted
2002-02-10	KB	Patent renewed
2002-07-25	KB	Patent renewed
2011-02-28	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
US5981754A (en)	1999-11-09	4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines having neurotrophic and neuroprotective activity
AU730143B2 (en)	2001-03-01	1-phenylalkyl-1,2,3,6-tetrahydropyridines for treating Alzheimer's disease
AU730142B2 (en)	2001-03-01	Diphenylalkyl-tetrahydropyridines, process for their preparation and pharmaceutical composition containing them
US7151107B2 (en)	2006-12-19	Use of benzoylalkyl-1,2,3,6-tetrahydropyridines
CA2420620A1 (en)	1997-01-16	4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines having neurotrophic and neuroprotective activity
MXPA97010472A (en)	1998-10-15	4-aril-phenylalkil-1,2,3,6-tetrahydropiridines that have a neuroprophic activity and neuroprotect
MXPA99005651A (es)	2000-05-01	Uso de benzoilalquil-1,2,3,6-tetrahidropiridinas