NO310144B1 - 4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning - Google Patents

4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning Download PDF

Info

Publication number: NO310144B1
Authority: NO; Norway
Prior art keywords: mixture; ethyl; tetrahydropyridine; mol; formula
Prior art date: 1995-06-28

Application number

NO19976079A

Other languages

English (en)

Norwegian (no)

Other versions

NO976079D0 (no

NO976079L (no

Inventor

Domenico Badone

Marco Baroni

Rosanna Cardamone

Jacqueline Fournier

Umberto Guzzi

Alessandra Ielmini

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

1997-12-23

Publication date

2001-05-28

1997-12-23 Application filed by Sanofi Synthelabo filed Critical Sanofi Synthelabo

1997-12-23 Publication of NO976079D0 publication Critical patent/NO976079D0/no

1997-12-23 Publication of NO976079L publication Critical patent/NO976079L/no

2001-05-28 Publication of NO310144B1 publication Critical patent/NO310144B1/no

Links

238000000034 method Methods 0.000 title claims description 74
238000002360 preparation method Methods 0.000 title claims description 12
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
230000000324 neuroprotective effect Effects 0.000 title description 3
230000002276 neurotropic effect Effects 0.000 title description 3
-1 phenoxy, phenylamino Chemical group 0.000 claims abstract description 41
150000003839 salts Chemical class 0.000 claims abstract description 32
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
239000012453 solvate Substances 0.000 claims abstract description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
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
150000001875 compounds Chemical class 0.000 claims description 161
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
238000010992 reflux Methods 0.000 claims description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 18
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 18
239000002585 base Substances 0.000 claims description 16
239000003795 chemical substances by application Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
238000012546 transfer Methods 0.000 claims description 8
150000002940 palladium Chemical class 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
239000012736 aqueous medium Substances 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
125000006529 (C3-C6) alkyl group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical group 0.000 claims description 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 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
230000008569 process Effects 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
150000003863 ammonium salts Chemical class 0.000 abstract 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
125000005111 carboxyalkoxy group Chemical group 0.000 abstract 1
125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
125000006310 cycloalkyl amino group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000004981 cycloalkylmethyl group Chemical group 0.000 abstract 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 abstract 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
125000005504 styryl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 263
239000000203 mixture Substances 0.000 description 174
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 107
239000002904 solvent Substances 0.000 description 94
239000000047 product Substances 0.000 description 71
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 70
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
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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
239000012074 organic phase Substances 0.000 description 53
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
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
239000000741 silica gel Substances 0.000 description 31
229910002027 silica gel Inorganic materials 0.000 description 31
238000004587 chromatography analysis Methods 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
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
239000003921 oil Substances 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
HAKSOKWVNPZVNM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridine;hydrochloride Chemical compound Cl.C1CNC=CC1 HAKSOKWVNPZVNM-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
239000012047 saturated solution Substances 0.000 description 18
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 17
239000002253 acid Substances 0.000 description 17
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 14
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
239000012071 phase Substances 0.000 description 12
238000004809 thin layer chromatography Methods 0.000 description 12
238000011282 treatment Methods 0.000 description 12
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 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
239000007787 solid Substances 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
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
235000011181 potassium carbonates Nutrition 0.000 description 9
239000011541 reaction mixture 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
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
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208000035475 disorder Diseases 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
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238000004519 manufacturing process Methods 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
JLORCINISDJUDL-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]propyl methanesulfonate Chemical compound CC(C)CC1=CC=C(C(C)COS(C)(=O)=O)C=C1 JLORCINISDJUDL-UHFFFAOYSA-N 0.000 description 5
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
150000002148 esters Chemical class 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
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229910000104 sodium hydride Inorganic materials 0.000 description 5
238000012360 testing method Methods 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
LAVVHCGEKVRBIR-UHFFFAOYSA-N 2-[3-chloro-4-(3-chlorophenyl)phenyl]acetic acid Chemical compound ClC1=CC(CC(=O)O)=CC=C1C1=CC=CC(Cl)=C1 LAVVHCGEKVRBIR-UHFFFAOYSA-N 0.000 description 4
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-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
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000010779 crude oil Substances 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
235000006408 oxalic acid Nutrition 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
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 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
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-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
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239000004215 Carbon black (E152) Substances 0.000 description 3
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
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239000007864 aqueous solution Substances 0.000 description 3
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230000015572 biosynthetic process Effects 0.000 description 3
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LKVWHRHPCHSGSI-UHFFFAOYSA-N ethyl 2-[3-chloro-4-(trifluoromethylsulfonyl)phenyl]acetate Chemical compound CCOC(=O)CC1=CC=C(S(=O)(=O)C(F)(F)F)C(Cl)=C1 LKVWHRHPCHSGSI-UHFFFAOYSA-N 0.000 description 3
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239000002609 medium Substances 0.000 description 3
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239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
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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
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FVAATHKAFDFBQL-UHFFFAOYSA-N 1-(2-bromoethyl)-4-cyclohexylbenzene Chemical compound C1=CC(CCBr)=CC=C1C1CCCCC1 FVAATHKAFDFBQL-UHFFFAOYSA-N 0.000 description 2
IDGZWZOGXPFMAL-UHFFFAOYSA-N 1-(2-bromoethyl)-4-phenylbenzene Chemical compound C1=CC(CCBr)=CC=C1C1=CC=CC=C1 IDGZWZOGXPFMAL-UHFFFAOYSA-N 0.000 description 2
RWPHWFAGKMQMNQ-UHFFFAOYSA-N 1-[2-(4-butylphenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine Chemical compound C1=CC(CCCC)=CC=C1CCN1CC=C(C=2C=C(C=CC=2)C(F)(F)F)CC1 RWPHWFAGKMQMNQ-UHFFFAOYSA-N 0.000 description 2
VALBFTWRAPRFAG-UHFFFAOYSA-N 1-[2-(4-cyclohexylphenyl)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)C3CCCCC3)CC=2)=C1 VALBFTWRAPRFAG-UHFFFAOYSA-N 0.000 description 2
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WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
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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

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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)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicinal Preparation (AREA)

NO19976079A 1995-06-28 1997-12-23 4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning NO310144B1 (no)

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 (3)

Publication Number	Publication Date
NO976079D0 NO976079D0 (no)	1997-12-23
NO976079L NO976079L (no)	1997-12-23
NO310144B1 true NO310144B1 (no)	2001-05-28

Family

ID=9480466

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19976079A NO310144B1 (no)	1995-06-28	1997-12-23	4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning

Country Status (29)

Country	Link
US (1)	US5981754A (de)
EP (2)	EP1216996A3 (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)	PL192353B1 (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)

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JP4866610B2 (ja)	2003-08-18	2012-02-01	富士フイルムファインケミカルズ株式会社	ピリジルテトラヒドロピリジン類およびピリジルピペリジン類
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US8110581B2 (en)	2004-11-10	2012-02-07	Incyte Corporation	Lactam compounds and their use as pharmaceuticals
CA2585797C (en) *	2004-11-10	2015-01-06	Incyte Corporation	Lactam compounds and their use as pharmaceuticals
JP2008520700A (ja) *	2004-11-18	2008-06-19	インサイト・コーポレイション	１１−βヒドロキシルステロイドデヒドロゲナーゼタイプＩの阻害剤およびその使用方法
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
WO2007038138A2 (en) *	2005-09-21	2007-04-05	Incyte Corporation	Amido compounds and their use as pharmaceuticals
EP1957494A2 (de) *	2005-12-05	2008-08-20	Incyte Corporation	Lactam-verbindungen und verfahren zu ihrer verwendung
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
WO2007103719A2 (en) *	2006-03-03	2007-09-13	Incyte Corporation	MODULATORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE 1, PHARMACEUTICAL COMPOSITIONS THEREOF, AND METHODS OF USING THE SAME
WO2007130898A1 (en) *	2006-05-01	2007-11-15	Incyte Corporation	TETRASUBSTITUTED UREAS AS MODULATORS OF 11-β HYDROXYL STEROID DEHYDROGENASE TYPE 1
JP2009537564A (ja) *	2006-05-17	2009-10-29	インサイト・コーポレイション	１１−βヒドロキシルステロイドデヒドロゲナーゼタイプＩの複素環阻害剤およびそれを用いる方法
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.
JP2011507909A (ja)	2007-12-20	2011-03-10	エンビボファーマシューティカルズインコーポレイテッド	四置換ベンゼン
CN102753513B (zh) *	2010-01-19	2015-03-18	拜耳知识产权有限责任公司	制备芳基和杂芳基乙酸衍生物的方法
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1995
- 1995-06-28 FR FR9507760A patent/FR2736053B1/fr not_active Expired - Fee Related
1996
- 1996-06-26 HU HU9900055A patent/HUP9900055A3/hu unknown
- 1996-06-26 CA CA002225746A patent/CA2225746C/en not_active Expired - Fee Related
- 1996-06-26 UA UA97126360A patent/UA62914C2/uk unknown
- 1996-06-26 EP EP02006482A patent/EP1216996A3/de not_active Withdrawn
- 1996-06-26 CN CNB961950900A patent/CN1153765C/zh not_active Expired - Fee Related
- 1996-06-26 PT PT96924023T patent/PT837848E/pt unknown
- 1996-06-26 WO PCT/FR1996/000995 patent/WO1997001536A1/fr not_active Ceased
- 1996-06-26 EP EP96924023A patent/EP0837848B1/de not_active Expired - Lifetime
- 1996-06-26 NZ NZ312723A patent/NZ312723A/en unknown
- 1996-06-26 SK SK1781-97A patent/SK283707B6/sk unknown
- 1996-06-26 ES ES96924023T patent/ES2183965T3/es not_active Expired - Lifetime
- 1996-06-26 BR BR9608662A patent/BR9608662A/pt not_active IP Right Cessation
- 1996-06-26 US US08/973,712 patent/US5981754A/en not_active Expired - Fee Related
- 1996-06-26 DE DE69623631T patent/DE69623631T2/de not_active Expired - Fee Related
- 1996-06-26 KR KR1019970709747A patent/KR100460581B1/ko not_active Expired - Fee Related
- 1996-06-26 TR TR97/01710T patent/TR199701710T1/xx unknown
- 1996-06-26 RU RU98101492/04A patent/RU2163237C2/ru not_active IP Right Cessation
- 1996-06-26 CZ CZ19974222A patent/CZ291075B6/cs not_active IP Right Cessation
- 1996-06-26 PL PL357052A patent/PL192353B1/pl not_active IP Right Cessation
- 1996-06-26 AT AT96924023T patent/ATE223897T1/de not_active IP Right Cessation
- 1996-06-26 DK DK96924023T patent/DK0837848T3/da active
- 1996-06-26 IL IL12215996A patent/IL122159A/en not_active IP Right Cessation
- 1996-06-26 AU AU64619/96A patent/AU715090B2/en not_active Ceased
- 1996-06-26 SK SK593-2003A patent/SK285433B6/sk unknown
- 1996-06-26 JP JP50420697A patent/JP3147906B2/ja not_active Expired - Fee Related
- 1996-06-26 EE EE9700348A patent/EE03870B1/xx not_active IP Right Cessation
- 1996-06-26 PL PL96324216A patent/PL187087B1/pl not_active IP Right Cessation
- 1996-06-28 ZA ZA965527A patent/ZA965527B/xx unknown
1997
- 1997-12-23 NO NO19976079A patent/NO310144B1/no unknown
- 1997-12-23 IS IS4641A patent/IS1999B/is unknown
2000
- 2000-07-31 JP JP2000231069A patent/JP3302351B2/ja not_active Expired - Fee Related
2003
- 2003-01-15 CY CY0300004A patent/CY2312B1/xx unknown

Also Published As

Publication number	Publication date
HUP9900055A3 (en)	1999-11-29
BR9608662A (pt)	1999-05-04
DK0837848T3 (da)	2003-01-06
CZ422297A3 (cs)	1998-04-15
MX9710472A (es)	1998-03-31
KR19990028431A (ko)	1999-04-15
IL122159A0 (en)	1998-04-05
HUP9900055A2 (hu)	1999-04-28
AU715090B2 (en)	2000-01-13
JP3147906B2 (ja)	2001-03-19
EE9700348A (et)	1998-06-15
DE69623631T2 (de)	2003-08-07
ATE223897T1 (de)	2002-09-15
JP2001114763A (ja)	2001-04-24
UA62914C2 (en)	2004-01-15
HK1014952A1 (en)	1999-10-08
EE03870B1 (et)	2002-10-15
FR2736053A1 (fr)	1997-01-03
TR199701710T1 (xx)	1998-05-21
CY2312B1 (en)	2003-11-14
DE69623631D1 (en)	2002-10-17
SK178197A3 (en)	1998-07-08
RU2163237C2 (ru)	2001-02-20
EP0837848A1 (de)	1998-04-29
FR2736053B1 (fr)	1997-09-19
KR100460581B1 (ko)	2005-04-14
NO976079D0 (no)	1997-12-23
EP1216996A3 (de)	2003-10-15
PL324216A1 (en)	1998-05-11
CA2225746C (en)	2004-05-18
PL192353B1 (pl)	2006-10-31
NZ312723A (en)	1999-10-28
CZ291075B6 (cs)	2002-12-11
IS4641A (is)	1997-12-23
JPH11506118A (ja)	1999-06-02
ZA965527B (en)	1997-01-24
AU6461996A (en)	1997-01-30
JP3302351B2 (ja)	2002-07-15
CA2225746A1 (en)	1997-01-16
CN1189154A (zh)	1998-07-29
ES2183965T3 (es)	2003-04-01
SK285433B6 (sk)	2007-01-04
PT837848E (pt)	2002-12-31
NO976079L (no)	1997-12-23
PL187087B1 (pl)	2004-05-31
EP1216996A2 (de)	2002-06-26
CN1153765C (zh)	2004-06-16
EP0837848B1 (de)	2002-09-11
IL122159A (en)	2001-06-14
US5981754A (en)	1999-11-09
WO1997001536A1 (fr)	1997-01-16
SK283707B6 (sk)	2003-12-02
IS1999B (is)	2005-04-15

Publication	Publication Date	Title
NO310144B1 (no)	2001-05-28	4-Aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridiner med neurotropisk og neurobeskyttende aktivitet, fremgangsmåte forfremstilling derav og farmasöytisk sammensetning
AU3255200A (en)	2000-11-09	New substituted pyridine or piperidine compounds, a process for their preparation and pharmaceutical compositions containing them
KR100560358B1 (ko)	2006-03-14	알츠하이머 질환 치료용 1-페닐알킬-1,2,3,6-테트라히드로피리딘
US6124318A (en)	2000-09-26	Diphenylalkyl-tetrahydropyridines, process for their preparation, and pharmaceutical compositions 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
CZ291185B6 (cs)	2003-01-15	Způsob přípravy bifenylových derivátů vhodných pro přípravu 4-aryl-1-fenylalkyl-1,2,3,6-tetrahydropyridinů