UA62914C2 - 4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines, methods for preparation thereof and a pharmaceutical composition based thereon - Google Patents
4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines, methods for preparation thereof and a pharmaceutical composition based thereon Download PDFInfo
- Publication number
- UA62914C2 UA62914C2 UA97126360A UA97126360A UA62914C2 UA 62914 C2 UA62914 C2 UA 62914C2 UA 97126360 A UA97126360 A UA 97126360A UA 97126360 A UA97126360 A UA 97126360A UA 62914 C2 UA62914 C2 UA 62914C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- group
- compound
- tetrahydropyridine
- mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 82
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 186
- -1 phenoxy, phenylamino Chemical group 0.000 claims abstract description 113
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 239000012453 solvate Substances 0.000 claims abstract description 14
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical group 0.000 claims abstract description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 7
- 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 238000001816 cooling Methods 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 22
- 239000002585 base Substances 0.000 claims description 16
- 238000009835 boiling Methods 0.000 claims description 14
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 150000002940 palladium Chemical class 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 230000016507 interphase Effects 0.000 claims description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 claims description 2
- WUWPOFDLIREPEU-UHFFFAOYSA-N 3-fluoro-2-(1,2,3,6-tetrahydropyridin-4-yl)pyridine Chemical compound FC1=CC=CN=C1C1=CCNCC1 WUWPOFDLIREPEU-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 230000000324 neuroprotective effect Effects 0.000 abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl 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
- 230000000508 neurotrophic effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 149
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 147
- 239000002904 solvent Substances 0.000 description 93
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000047 product Substances 0.000 description 65
- 239000000243 solution Substances 0.000 description 65
- 238000002844 melting Methods 0.000 description 64
- 230000008018 melting Effects 0.000 description 64
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 62
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 58
- 235000011152 sodium sulphate Nutrition 0.000 description 58
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 57
- 229910052938 sodium sulfate Inorganic materials 0.000 description 57
- 239000012074 organic phase Substances 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000003480 eluent Substances 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
- 239000012043 crude product Substances 0.000 description 20
- 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 239000012047 saturated solution 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-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
- 239000007864 aqueous solution Substances 0.000 description 13
- 238000010992 reflux Methods 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
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 235000011181 potassium carbonates Nutrition 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 8
- 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 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 6
- NMWSKOLWZZWHPL-UHFFFAOYSA-N 3-chlorobiphenyl Chemical group ClC1=CC=CC(C=2C=CC=CC=2)=C1 NMWSKOLWZZWHPL-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 229910000085 borane Inorganic materials 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
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- 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
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- 150000001412 amines Chemical class 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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- 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 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
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- 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
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
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- 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
- 238000001521 two-tailed test Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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)
- 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)
- Plural Heterocyclic Compounds (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 (1)
| Publication Number | Publication Date |
|---|---|
| UA62914C2 true UA62914C2 (en) | 2004-01-15 |
Family
ID=9480466
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA97126360A UA62914C2 (en) | 1995-06-28 | 1996-06-26 | 4-aryl-1-phenylalkyl-1,2,3,6-tetrahydropyridines, methods for preparation thereof and a pharmaceutical composition based thereon |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US5981754A (is) |
| EP (2) | EP1216996A3 (is) |
| JP (2) | JP3147906B2 (is) |
| KR (1) | KR100460581B1 (is) |
| CN (1) | CN1153765C (is) |
| AT (1) | ATE223897T1 (is) |
| AU (1) | AU715090B2 (is) |
| BR (1) | BR9608662A (is) |
| CA (1) | CA2225746C (is) |
| CY (1) | CY2312B1 (is) |
| CZ (1) | CZ291075B6 (is) |
| DE (1) | DE69623631T2 (is) |
| DK (1) | DK0837848T3 (is) |
| EE (1) | EE03870B1 (is) |
| ES (1) | ES2183965T3 (is) |
| FR (1) | FR2736053B1 (is) |
| HK (1) | HK1014952A1 (is) |
| HU (1) | HUP9900055A3 (is) |
| IL (1) | IL122159A (is) |
| IS (1) | IS1999B (is) |
| NO (1) | NO310144B1 (is) |
| NZ (1) | NZ312723A (is) |
| PL (2) | PL192353B1 (is) |
| PT (1) | PT837848E (is) |
| RU (1) | RU2163237C2 (is) |
| SK (2) | SK285433B6 (is) |
| TR (1) | TR199701710T1 (is) |
| UA (1) | UA62914C2 (is) |
| WO (1) | WO1997001536A1 (is) |
| ZA (1) | ZA965527B (is) |
Families Citing this family (36)
| 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 |
| 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 |
| 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 |
| ATE365162T1 (de) | 2001-04-20 | 2007-07-15 | 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 |
| US7632950B2 (en) | 2003-08-18 | 2009-12-15 | Fujifilm Finechemicals Co., Ltd | Pyridyltetrahydropyridines and pyridylpiperidines and method of manufacturing them |
| TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| US7687665B2 (en) * | 2004-06-24 | 2010-03-30 | Incyte Corporation | 2-methylprop anamides and their use as pharmaceuticals |
| JP2008504279A (ja) * | 2004-06-24 | 2008-02-14 | インサイト・コーポレイション | アミド化合物およびその医薬としての使用 |
| EP1758582A4 (en) * | 2004-06-24 | 2008-01-09 | Incyte Corp | AMIDO COMPOUNDS AND THEIR USE AS PHARMACEUTICAL PRODUCTS |
| JP2008504274A (ja) * | 2004-06-24 | 2008-02-14 | インサイト・コーポレイション | アミド化合物およびその医薬としての使用 |
| EA200700117A1 (ru) | 2004-06-24 | 2007-06-29 | Инсайт Корпорейшн | N-замещенные пиперидины и их применение в качестве фармацевтических препаратов |
| MX2007001540A (es) * | 2004-08-10 | 2007-04-23 | Incyte Corp | Compuestos amido y sus usos como farmaceuticos. |
| US8110581B2 (en) | 2004-11-10 | 2012-02-07 | Incyte Corporation | Lactam compounds and their use as pharmaceuticals |
| ES2547724T3 (es) * | 2004-11-10 | 2015-10-08 | Incyte Corporation | Compuestos de lactama y su uso como productos farmacéuticos |
| KR20070097441A (ko) * | 2004-11-18 | 2007-10-04 | 인사이트 산 디에고 인코포레이티드 | 11-β 하이드록실 스테로이드 데하이드로게나제 유형 1의억제제 및 이를 사용하는 방법 |
| 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 |
| TW200804382A (en) * | 2005-12-05 | 2008-01-16 | Incyte Corp | Lactam compounds and methods of using the same |
| 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 |
| US20070197530A1 (en) * | 2006-01-31 | 2007-08-23 | Yun-Long Li | Amido compounds and their use as pharmaceuticals |
| 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 |
| CA2649677A1 (en) * | 2006-05-01 | 2007-11-15 | Incyte Corporation | Tetrasubstituted ureas as modulators of 11-.beta. hydroxyl steroid dehydrogenase type 1 |
| US7838544B2 (en) * | 2006-05-17 | 2010-11-23 | Incyte Corporation | Heterocyclic inhibitors of 11-β hydroxyl steroid dehydrogenase type 1 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. |
| EP2234954B1 (en) | 2007-12-20 | 2015-02-18 | Envivo Pharmaceuticals, Inc. | Tetrasubstituted benzenes |
| KR101773070B1 (ko) * | 2010-01-19 | 2017-09-12 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 아릴 및 헤테로아릴아세트산 유도체의 제조방법 |
| US10858351B2 (en) | 2017-04-26 | 2020-12-08 | Alberta Research Chemicals Inc. | Substituted tetrahydropyridine derivatives as IDO-1 inhibitors and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0398578B1 (en) * | 1989-05-17 | 1997-03-12 | Pfizer Inc. | 2-piperidino-1-alkanol derivatives as antiischemic agents |
| 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 |
-
1995
- 1995-06-28 FR FR9507760A patent/FR2736053B1/fr not_active Expired - Fee Related
-
1996
- 1996-06-26 WO PCT/FR1996/000995 patent/WO1997001536A1/fr active IP Right Grant
- 1996-06-26 RU RU98101492/04A patent/RU2163237C2/ru not_active IP Right Cessation
- 1996-06-26 HU HU9900055A patent/HUP9900055A3/hu unknown
- 1996-06-26 EP EP02006482A patent/EP1216996A3/fr not_active Withdrawn
- 1996-06-26 PL PL357052A patent/PL192353B1/pl not_active IP Right Cessation
- 1996-06-26 CN CNB961950900A patent/CN1153765C/zh not_active Expired - Fee Related
- 1996-06-26 AT AT96924023T patent/ATE223897T1/de not_active IP Right Cessation
- 1996-06-26 EE EE9700348A patent/EE03870B1/xx not_active IP Right Cessation
- 1996-06-26 SK SK593-2003A patent/SK285433B6/sk unknown
- 1996-06-26 PT PT96924023T patent/PT837848E/pt unknown
- 1996-06-26 US US08/973,712 patent/US5981754A/en not_active Expired - Fee Related
- 1996-06-26 TR TR97/01710T patent/TR199701710T1/xx unknown
- 1996-06-26 IL IL12215996A patent/IL122159A/en not_active IP Right Cessation
- 1996-06-26 EP EP96924023A patent/EP0837848B1/fr not_active Expired - Lifetime
- 1996-06-26 AU AU64619/96A patent/AU715090B2/en not_active Ceased
- 1996-06-26 UA UA97126360A patent/UA62914C2/uk unknown
- 1996-06-26 CZ CZ19974222A patent/CZ291075B6/cs not_active IP Right Cessation
- 1996-06-26 SK SK1781-97A patent/SK283707B6/sk unknown
- 1996-06-26 DE DE69623631T patent/DE69623631T2/de not_active Expired - Fee Related
- 1996-06-26 PL PL96324216A patent/PL187087B1/pl not_active IP Right Cessation
- 1996-06-26 DK DK96924023T patent/DK0837848T3/da active
- 1996-06-26 KR KR1019970709747A patent/KR100460581B1/ko not_active IP Right Cessation
- 1996-06-26 CA CA002225746A patent/CA2225746C/en not_active Expired - Fee Related
- 1996-06-26 BR BR9608662A patent/BR9608662A/pt not_active IP Right Cessation
- 1996-06-26 NZ NZ312723A patent/NZ312723A/en unknown
- 1996-06-26 JP JP50420697A patent/JP3147906B2/ja not_active Expired - Fee Related
- 1996-06-26 ES ES96924023T patent/ES2183965T3/es not_active Expired - Lifetime
- 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
-
1999
- 1999-01-14 HK HK99100183A patent/HK1014952A1/xx not_active IP Right Cessation
-
2000
- 2000-07-31 JP JP2000231069A patent/JP3302351B2/ja not_active Expired - Fee Related
-
2003
- 2003-01-15 CY CY0300004A patent/CY2312B1/xx unknown
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