MX2011006680A - Compuestos etanaminicos y su uso para tratar la depresion. - Google Patents
Compuestos etanaminicos y su uso para tratar la depresion.Info
- Publication number
- MX2011006680A MX2011006680A MX2011006680A MX2011006680A MX2011006680A MX 2011006680 A MX2011006680 A MX 2011006680A MX 2011006680 A MX2011006680 A MX 2011006680A MX 2011006680 A MX2011006680 A MX 2011006680A MX 2011006680 A MX2011006680 A MX 2011006680A
- Authority
- MX
- Mexico
- Prior art keywords
- pharmaceutically acceptable
- compound
- methyl
- pyridin
- amine
- Prior art date
Links
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical class CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 title abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 114
- IFOJJUKSLKNAOM-UHFFFAOYSA-N 2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-amine Chemical compound C=1C=CC=NC=1C(C)(C)C(N)C1=CC=CC=C1 IFOJJUKSLKNAOM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 180
- 238000000034 method Methods 0.000 claims description 68
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 34
- 239000008194 pharmaceutical composition Substances 0.000 claims description 32
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 30
- 239000003085 diluting agent Substances 0.000 claims description 26
- 208000024714 major depressive disease Diseases 0.000 claims description 26
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 25
- 239000002671 adjuvant Substances 0.000 claims description 24
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 15
- JCABFPBDEZEFKI-CQSZACIVSA-N (1r)-1-(3-fluorophenyl)-2-methyl-2-pyridin-2-ylpropan-1-amine Chemical compound C1([C@@H](N)C(C)(C)C=2N=CC=CC=2)=CC=CC(F)=C1 JCABFPBDEZEFKI-CQSZACIVSA-N 0.000 claims description 12
- IFOJJUKSLKNAOM-AWEZNQCLSA-N (1s)-2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-amine Chemical compound C1([C@H](N)C(C)(C)C=2N=CC=CC=2)=CC=CC=C1 IFOJJUKSLKNAOM-AWEZNQCLSA-N 0.000 claims description 10
- JCABFPBDEZEFKI-UHFFFAOYSA-N 1-(3-fluorophenyl)-2-methyl-2-pyridin-2-ylpropan-1-amine Chemical compound C=1C=CC=NC=1C(C)(C)C(N)C1=CC=CC(F)=C1 JCABFPBDEZEFKI-UHFFFAOYSA-N 0.000 claims description 10
- JCABFPBDEZEFKI-AWEZNQCLSA-N (1s)-1-(3-fluorophenyl)-2-methyl-2-pyridin-2-ylpropan-1-amine Chemical compound C1([C@H](N)C(C)(C)C=2N=CC=CC=2)=CC=CC(F)=C1 JCABFPBDEZEFKI-AWEZNQCLSA-N 0.000 claims description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 9
- IFOJJUKSLKNAOM-CQSZACIVSA-N (1r)-2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-amine Chemical compound C1([C@@H](N)C(C)(C)C=2N=CC=CC=2)=CC=CC=C1 IFOJJUKSLKNAOM-CQSZACIVSA-N 0.000 claims description 6
- CFSJJFHTEWSWEU-UHFFFAOYSA-N 2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-one Chemical compound C=1C=CC=NC=1C(C)(C)C(=O)C1=CC=CC=C1 CFSJJFHTEWSWEU-UHFFFAOYSA-N 0.000 claims description 6
- IMFYGXNQBXJCAN-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(3-fluorophenyl)-2-methyl-2-pyridin-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=NC=1C(C)(C)C(N)C1=CC=CC(F)=C1 IMFYGXNQBXJCAN-WLHGVMLRSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 3
- MAKZOTAGHBIOMS-WLHGVMLRSA-N (e)-but-2-enedioic acid;2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C=1C=CC=NC=1C(C)(C)C(N)C1=CC=CC=C1 MAKZOTAGHBIOMS-WLHGVMLRSA-N 0.000 claims description 2
- MAKZOTAGHBIOMS-WZGZYPNHSA-N (e)-but-2-enedioic acid;(1r)-2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C1([C@@H](N)C(C)(C)C=2N=CC=CC=2)=CC=CC=C1 MAKZOTAGHBIOMS-WZGZYPNHSA-N 0.000 claims 2
- IMFYGXNQBXJCAN-KZHAMYRLSA-N (e)-but-2-enedioic acid;(1s)-1-(3-fluorophenyl)-2-methyl-2-pyridin-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C1([C@H](N)C(C)(C)C=2N=CC=CC=2)=CC=CC(F)=C1 IMFYGXNQBXJCAN-KZHAMYRLSA-N 0.000 claims 1
- MAKZOTAGHBIOMS-KZHAMYRLSA-N (e)-but-2-enedioic acid;(1s)-2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-amine Chemical compound OC(=O)\C=C\C(O)=O.C1([C@H](N)C(C)(C)C=2N=CC=CC=2)=CC=CC=C1 MAKZOTAGHBIOMS-KZHAMYRLSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 18
- 238000011282 treatment Methods 0.000 abstract description 15
- 208000020401 Depressive disease Diseases 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000000203 mixture Substances 0.000 description 48
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- -1 phenylacetyl Chemical group 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 239000002207 metabolite Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 125000002252 acyl group Chemical group 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 238000002560 therapeutic procedure Methods 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- KHEXSXPVKHWNOZ-CQSZACIVSA-N n-benzylidene-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N=CC1=CC=CC=C1 KHEXSXPVKHWNOZ-CQSZACIVSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 229940002612 prodrug Drugs 0.000 description 6
- 239000000651 prodrug Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- SBUFLLIBYNAWGH-UHFFFAOYSA-N 2-methyl-1-phenyl-2-pyridin-2-ylpropan-1-amine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=NC=1C(C)(C)C(N)C1=CC=CC=C1 SBUFLLIBYNAWGH-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000007903 gelatin capsule Substances 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 238000004808 supercritical fluid chromatography Methods 0.000 description 5
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 4
- PFYPDUUXDADWKC-UHFFFAOYSA-N 2-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC=N1 PFYPDUUXDADWKC-UHFFFAOYSA-N 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 125000003435 aroyl group Chemical group 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 229960002870 gabapentin Drugs 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
- 229940011051 isopropyl acetate Drugs 0.000 description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 4
- 229960000604 valproic acid Drugs 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000007080 aromatic substitution reaction Methods 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 3
- 229960000623 carbamazepine Drugs 0.000 description 3
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- 230000007062 hydrolysis Effects 0.000 description 3
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- 238000007918 intramuscular administration Methods 0.000 description 3
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- 239000012279 sodium borohydride Substances 0.000 description 3
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- AEQFSUDEHCCHBT-UHFFFAOYSA-M sodium valproate Chemical compound [Na+].CCCC(C([O-])=O)CCC AEQFSUDEHCCHBT-UHFFFAOYSA-M 0.000 description 3
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- YLXDSYKOBKBWJQ-LBPRGKRZSA-N N-[2-[(8S)-2,6,7,8-tetrahydro-1H-cyclopenta[e]benzofuran-8-yl]ethyl]propanamide Chemical compound C1=C2OCCC2=C2[C@H](CCNC(=O)CC)CCC2=C1 YLXDSYKOBKBWJQ-LBPRGKRZSA-N 0.000 description 2
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 2
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
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- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
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- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
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- DTMPGSXFUXZBDK-UHFFFAOYSA-N uldazepam Chemical compound C12=CC(Cl)=CC=C2N=C(NOCC=C)CN=C1C1=CC=CC=C1Cl DTMPGSXFUXZBDK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Confectionery (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14067308P | 2008-12-24 | 2008-12-24 | |
| PCT/SE2009/051493 WO2010074647A1 (en) | 2008-12-24 | 2009-12-22 | Ethanamine compounds and their use for treating depression |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2011006680A true MX2011006680A (es) | 2011-07-12 |
Family
ID=42288011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2011006680A MX2011006680A (es) | 2008-12-24 | 2009-12-22 | Compuestos etanaminicos y su uso para tratar la depresion. |
Country Status (31)
| Country | Link |
|---|---|
| US (4) | US8013165B2 (enExample) |
| EP (2) | EP2610246A1 (enExample) |
| JP (1) | JP5491524B2 (enExample) |
| KR (1) | KR20110097996A (enExample) |
| CN (1) | CN102333762B (enExample) |
| AR (1) | AR074981A1 (enExample) |
| AU (1) | AU2009330745B2 (enExample) |
| BR (1) | BRPI0923476A2 (enExample) |
| CA (1) | CA2748235A1 (enExample) |
| CL (1) | CL2011001590A1 (enExample) |
| CO (1) | CO6450688A2 (enExample) |
| CR (1) | CR20110365A (enExample) |
| CU (1) | CU24017B1 (enExample) |
| DO (1) | DOP2011000205A (enExample) |
| EA (1) | EA201190064A1 (enExample) |
| EC (1) | ECSP11011161A (enExample) |
| GT (1) | GT201100186A (enExample) |
| HN (1) | HN2011001773A (enExample) |
| IL (1) | IL213518A0 (enExample) |
| MX (1) | MX2011006680A (enExample) |
| NI (1) | NI201100131A (enExample) |
| NZ (1) | NZ593282A (enExample) |
| PE (1) | PE20120249A1 (enExample) |
| SA (1) | SA109310013B1 (enExample) |
| SG (2) | SG192510A1 (enExample) |
| SV (1) | SV2011003962A (enExample) |
| TW (1) | TWI442922B (enExample) |
| UA (1) | UA106056C2 (enExample) |
| UY (1) | UY32360A (enExample) |
| WO (1) | WO2010074647A1 (enExample) |
| ZA (1) | ZA201105441B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8013165B2 (en) | 2008-12-24 | 2011-09-06 | Astrazeneca Ab | Ethanamine compounds and methods of using the same 545 |
| CN112250676B (zh) * | 2020-11-24 | 2023-05-16 | 深圳市第二人民医院(深圳市转化医学研究院) | 一种具有抗抑郁活性的含氧杂环化合物 |
| CN112279843B (zh) * | 2020-11-24 | 2023-05-16 | 深圳市第二人民医院(深圳市转化医学研究院) | 一种具有抗抑郁活性的含氮杂环化合物 |
Family Cites Families (17)
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| US3422191A (en) * | 1965-01-21 | 1969-01-14 | Synergistics Inc | Compositions and methods for tranquilization employing salts of n-morpholine ethanol |
| GB1427026A (en) | 1972-11-20 | 1976-03-03 | Ici Ltd | Synthetic film materials |
| JPS5756474B2 (enExample) | 1973-05-26 | 1982-11-30 | ||
| US5455259A (en) * | 1987-02-06 | 1995-10-03 | Fisons Corporation | Compounds for the treatment of neurodegenerative disorders |
| GB9320273D0 (en) | 1993-04-01 | 1993-11-17 | Fisons Corp | Compound useful in therapy |
| EP0356035B1 (en) | 1988-08-12 | 1996-03-13 | Astra Aktiebolag | Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| JP2514855B2 (ja) | 1990-08-08 | 1996-07-10 | キッセイ薬品工業株式会社 | 光学活性なアラニンアニリド誘導体の酸付加塩 |
| US5206248A (en) * | 1992-03-27 | 1993-04-27 | Smith Richard A | Method for reducing emotional lability |
| DK0612314T3 (da) * | 1991-10-30 | 2000-05-29 | Astra Ab | 2-pyrazinylethylaminderivater og deres anvendelse som lægemidler |
| KR100259567B1 (ko) * | 1992-04-03 | 2000-07-01 | 클래스 빌헬름슨 | 신경변성 질환 치료용 1-페닐-2-(2-피리디닐)에틸아민 에난티오머 |
| IL120669A (en) * | 1996-04-19 | 2001-04-30 | Akzo Nobel Nv | Benzoheterocyclic benzylamine derivatives and pharmaceutical compositions containing them |
| ATE229004T1 (de) | 1997-03-31 | 2002-12-15 | Korea Res Inst Chem Tech | Chinolinische sulfid-derivate als nmda rezeptor- antagonisten und verfahren zu ihrer herstellung |
| TW544448B (en) | 1997-07-11 | 2003-08-01 | Novartis Ag | Pyridine derivatives |
| SE9901077D0 (sv) | 1999-03-23 | 1999-03-23 | Astra Ab | Novel use |
| SE9901340D0 (sv) * | 1999-04-15 | 1999-04-15 | Astra Pharma Prod | Novel process |
| DE10334188B4 (de) * | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
| US8013165B2 (en) | 2008-12-24 | 2011-09-06 | Astrazeneca Ab | Ethanamine compounds and methods of using the same 545 |
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2009
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- 2009-12-22 EA EA201190064A patent/EA201190064A1/ru unknown
- 2009-12-22 KR KR1020117017236A patent/KR20110097996A/ko not_active Withdrawn
- 2009-12-22 JP JP2011543474A patent/JP5491524B2/ja not_active Expired - Fee Related
- 2009-12-22 CA CA2748235A patent/CA2748235A1/en not_active Abandoned
- 2009-12-22 WO PCT/SE2009/051493 patent/WO2010074647A1/en not_active Ceased
- 2009-12-22 BR BRPI0923476A patent/BRPI0923476A2/pt not_active IP Right Cessation
- 2009-12-22 NZ NZ593282A patent/NZ593282A/xx not_active IP Right Cessation
- 2009-12-22 AU AU2009330745A patent/AU2009330745B2/en not_active Ceased
- 2009-12-22 SG SG2013053749A patent/SG192510A1/en unknown
- 2009-12-22 EP EP13159532.4A patent/EP2610246A1/en not_active Withdrawn
- 2009-12-22 EP EP09835355A patent/EP2391606A4/en not_active Withdrawn
- 2009-12-22 UA UAA201107171A patent/UA106056C2/uk unknown
- 2009-12-22 MX MX2011006680A patent/MX2011006680A/es active IP Right Grant
- 2009-12-22 SA SA109310013A patent/SA109310013B1/ar unknown
- 2009-12-22 SG SG2011040342A patent/SG171928A1/en unknown
- 2009-12-22 PE PE2011001282A patent/PE20120249A1/es not_active Application Discontinuation
- 2009-12-22 CN CN200980157411.9A patent/CN102333762B/zh not_active Expired - Fee Related
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