IL23869A - 1 -) 2 - Dimethylaminoethyl (- 1 - phenylindene and 1 -] 2 -) methyl - amino (ethyl [- 1 - phenylindene - Google Patents

1 -) 2 - Dimethylaminoethyl (- 1 - phenylindene and 1 -] 2 -) methyl - amino (ethyl [- 1 - phenylindene

Info

Publication number: IL23869A
Authority: IL; Israel
Prior art keywords: phenylindene; formula; compound; group; dimethylaminoethyl
Prior art date: 1964-09-15

Application number

IL23869A

Other languages

English (en)

Hebrew (he)

Original Assignee

Mead Johnson & Co

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.)

1964-09-15

Filing date

1965-07-02

Publication date

1970-09-17

1965-07-02 Application filed by Mead Johnson & Co filed Critical Mead Johnson & Co

1970-09-17 Publication of IL23869A publication Critical patent/IL23869A/en

Links

KAQPNQMPHIRKJJ-UHFFFAOYSA-N n,n-dimethyl-2-(1-phenylinden-1-yl)ethanamine Chemical compound C1=CC2=CC=CC=C2C1(CCN(C)C)C1=CC=CC=C1 KAQPNQMPHIRKJJ-UHFFFAOYSA-N 0.000 title description 2
HUGLAQUJRPXQOX-UHFFFAOYSA-N n-methyl-2-(1-phenylinden-1-yl)ethanamine Chemical compound C1=CC2=CC=CC=C2C1(CCNC)C1=CC=CC=C1 HUGLAQUJRPXQOX-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 15
241001465754 Metazoa Species 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
ILASZRLOZFHWOJ-UHFFFAOYSA-N 3-phenyl-1h-indene Chemical compound C12=CC=CC=C2CC=C1C1=CC=CC=C1 ILASZRLOZFHWOJ-UHFFFAOYSA-N 0.000 claims description 7
-1 alkali metal salt Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
230000001430 anti-depressive effect Effects 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
239000000463 material Substances 0.000 claims description 4
230000037396 body weight Effects 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
230000000994 depressogenic effect Effects 0.000 claims description 3
238000004821 distillation Methods 0.000 claims description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
238000001640 fractional crystallisation Methods 0.000 claims description 2
125000002346 iodo group Chemical group I* 0.000 claims description 2
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
229910052739 hydrogen Chemical group 0.000 claims 1
239000001257 hydrogen Chemical group 0.000 claims 1
229910052744 lithium Inorganic materials 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 12
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 12
239000000935 antidepressant agent Substances 0.000 description 12
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 12
229960003147 reserpine Drugs 0.000 description 12
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
229940005513 antidepressants Drugs 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
206010015995 Eyelid ptosis Diseases 0.000 description 5
241000699666 Mus <mouse, genus> Species 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000012458 free base Substances 0.000 description 5
201000003004 ptosis Diseases 0.000 description 5
PXORBAGTGTXORO-UHFFFAOYSA-N 1-phenyl-1h-indene Chemical compound C1=CC2=CC=CC=C2C1C1=CC=CC=C1 PXORBAGTGTXORO-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000126 substance Substances 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229960000836 amitriptyline Drugs 0.000 description 3
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 3
230000000891 anti-reserpine Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
ZTCKJGNZNKVHOJ-UHFFFAOYSA-N n,n-dimethyl-2-(1-phenylinden-1-yl)ethanamine;hydrochloride Chemical compound Cl.C1=CC2=CC=CC=C2C1(CCN(C)C)C1=CC=CC=C1 ZTCKJGNZNKVHOJ-UHFFFAOYSA-N 0.000 description 3
239000003368 psychostimulant agent Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000002441 reversible effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229940025084 amphetamine Drugs 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
231100000517 death Toxicity 0.000 description 2
230000034994 death Effects 0.000 description 2
230000017858 demethylation Effects 0.000 description 2
238000010520 demethylation reaction Methods 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000002631 hypothermal effect Effects 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000002265 prevention Effects 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
206010011953 Decreased activity Diseases 0.000 description 1
206010021113 Hypothermia Diseases 0.000 description 1
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010027646 Miosis Diseases 0.000 description 1
208000006550 Mydriasis Diseases 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
206010039424 Salivary hypersecretion Diseases 0.000 description 1
229920002253 Tannate Polymers 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000036626 alertness Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000036528 appetite Effects 0.000 description 1
235000019789 appetite Nutrition 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
229960001948 caffeine Drugs 0.000 description 1
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003874 central nervous system depressant Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000002635 electroconvulsive therapy Methods 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229960004801 imipramine Drugs 0.000 description 1
BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940049920 malate Drugs 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
230000003547 miosis Effects 0.000 description 1
230000036651 mood Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229940127250 psychostimulant medication Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
HWEXKRHYVOGVDA-UHFFFAOYSA-M sodium;3-trimethylsilylpropane-1-sulfonate Chemical compound [Na+].C[Si](C)(C)CCCS([O-])(=O)=O HWEXKRHYVOGVDA-UHFFFAOYSA-M 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
BGRJTUBHPOOWDU-UHFFFAOYSA-N sulpiride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000041 toxicology testing Toxicity 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B12/00—Jointing of furniture or the like, e.g. hidden from exterior
- F16B12/44—Leg joints; Corner joints
- F16B12/48—Non-metal leg connections

Landscapes

Health & Medical Sciences (AREA)
General Engineering & Computer Science (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Chemical & Material Sciences (AREA)
Mechanical Engineering (AREA)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL23869A 1964-09-15 1965-07-02 1 -) 2 - Dimethylaminoethyl (- 1 - phenylindene and 1 -] 2 -) methyl - amino (ethyl [- 1 - phenylindene IL23869A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US39767364A	1964-09-15	1964-09-15
US457837A US3360435A (en)	1964-09-15	1965-05-21	Treatment of depressed states

Publications (1)

Publication Number	Publication Date
IL23869A true IL23869A (en)	1970-09-17

Family

ID=27015954

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL23869A IL23869A (en)	1964-09-15	1965-07-02	1 -) 2 - Dimethylaminoethyl (- 1 - phenylindene and 1 -] 2 -) methyl - amino (ethyl [- 1 - phenylindene

Country Status (11)

Country	Link
US (1)	US3360435A (fr)
BE (1)	BE667739A (fr)
BR (1)	BR6571638D0 (fr)
CH (2)	CH463486A (fr)
DE (1)	DE1543216B1 (fr)
ES (1)	ES315465A1 (fr)
FR (2)	FR4646M (fr)
GB (1)	GB1041989A (fr)
IL (1)	IL23869A (fr)
NL (1)	NL6509895A (fr)
SE (2)	SE322770B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE371190B (fr) *	1972-03-24	1974-11-11	Kabi Ab

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2798888A (en) *	1952-08-12	1957-07-09	Ciba Pharm Prod Inc	Indene and indane compounds and their production
NL282517A (fr) *	1961-08-31

1965
- 1965-05-21 US US457837A patent/US3360435A/en not_active Expired - Lifetime
- 1965-07-02 IL IL23869A patent/IL23869A/en unknown
- 1965-07-02 GB GB28248/65A patent/GB1041989A/en not_active Expired
- 1965-07-17 ES ES0315465A patent/ES315465A1/es not_active Expired
- 1965-07-26 SE SE9813/65A patent/SE322770B/xx unknown
- 1965-07-27 DE DE19651543216 patent/DE1543216B1/de active Pending
- 1965-07-28 BR BR171638/65A patent/BR6571638D0/pt unknown
- 1965-07-29 CH CH1068665A patent/CH463486A/de unknown
- 1965-07-29 CH CH1114968A patent/CH473760A/de not_active IP Right Cessation
- 1965-07-30 FR FR26747A patent/FR4646M/fr not_active Expired
- 1965-07-30 BE BE667739D patent/BE667739A/xx unknown
- 1965-07-30 FR FR26746A patent/FR1482826A/fr not_active Expired
- 1965-07-30 NL NL6509895A patent/NL6509895A/xx unknown
1968
- 1968-06-28 SE SE08871/68A patent/SE332171B/xx unknown

Also Published As

Publication number	Publication date
NL6509895A (fr)	1966-03-16
BE667739A (fr)	1966-01-31
ES315465A1 (es)	1966-06-01
SE322770B (fr)	1970-04-20
US3360435A (en)	1967-12-26
CH463486A (de)	1968-10-15
CH473760A (de)	1969-06-15
SE332171B (fr)	1971-02-01
FR1482826A (fr)	1967-06-02
DE1543216B1 (de)	1972-11-09
GB1041989A (en)	1966-09-07
FR4646M (fr)	1966-12-05
BR6571638D0 (pt)	1973-08-14

Publication	Publication Date	Title
US3534055A (en)	1970-10-13	Certain substituted 1-amino-1,2,3,4-tetrahydro naphthalenes and pharmaceutically acceptable salts thereof
US4299838A (en)	1981-11-10	Tryptophan derivatives having an increased effect on the central nervous system
HU197019B (en)	1989-02-28	Process for producing thiqzolo (4,5-c) quinoline derivatives and pharmaceuticals comprising same
EP0047536B1 (fr)	1984-06-27	Propylamines substituées
US3769427A (en)	1973-10-30	Pharmaceutical compositions and methods of using same
JPS63258476A (ja)	1988-10-25	ヘキサヒドロ−８−ヒドロキシ−２，６−メタノ−２ｈ−キノリジン−３（４ｈ）−オンのエステル類及び関連化合物類
JPH0440347B2 (fr)	1992-07-02
JPH04217977A (ja)	1992-08-07	新規なベンゾオキサジン及びベンゾチアジン誘導体及びその製造方法
IL32889A (en)	1973-03-30	Pyrido(4,3-b)indole derivatives,their preparation and pharmaceutical compositions containing them
JPH0446956B2 (fr)	1992-07-31
US3966731A (en)	1976-06-29	2-Fluoromethyl-3-o-tolyl-6-amino-4(3H)-quinazolinone
US4285943A (en)	1981-08-25	Novel pharmaceutical compositions incorporating an aryltrifluoroethanol
JPS5826332B2 (ja)	1983-06-02	テトラロ−ルカゴウブツノセイゾウホウ
JPS6139288B2 (fr)	1986-09-03
US3360435A (en)	1967-12-26	Treatment of depressed states
US3248292A (en)	1966-04-26	Pharmaceutically active dimethoxyquinazolines
Elslager et al.	1964	Synthetic Schistosomicides. VI. 4-Substituted 1-(Dialkylaminoalkylamino) naphthalenes1
US3496186A (en)	1970-02-17	2-aminomethyl benzofuran derivatives
US3796715A (en)	1974-03-12	8-alkoxy-3,4-dihydroisoquinolines
US4857529A (en)	1989-08-15	Interferon inducing, anti-vaccinia, and/or anti-influenza compositions
US3457354A (en)	1969-07-22	Treatment of hypertension with 2-hydroxy (or amino) - 4,5 - dihydroxyphenethylamine derivatives
US3420839A (en)	1969-01-07	Aminomethyl pyrazolone derivatives of nicotinamide
US3150139A (en)	1964-09-22	Nu-methylpiperazinocyclohexanol derivatives
US3487153A (en)	1969-12-30	Method of treating mental depression
US3128278A (en)	1964-04-07	Substituted l