CH551364A - Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa(cd)pentalenverbindungen. - Google Patents

Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa(cd)pentalenverbindungen.

Info

Publication number: CH551364A
Authority: CH; Switzerland
Prior art keywords: amino; tetrahydro; compounds; cyclopropa; dibenzo
Prior art date: 1969-08-29

Application number

CH1067572A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

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.)

1969-08-29

Filing date

1969-10-23

Publication date

1974-07-15

1969-10-23 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1974-07-15 Publication of CH551364A publication Critical patent/CH551364A/de

Links

239000000935 antidepressant agent Substances 0.000 title abstract description 6
229940005513 antidepressants Drugs 0.000 title abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 37
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 16
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
150000002148 esters Chemical group 0.000 claims abstract description 5
GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 claims abstract description 5
-1 3-dimethylaminopropyl Chemical group 0.000 claims description 82
150000001875 compounds Chemical class 0.000 claims description 43
125000000217 alkyl group Chemical group 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 25
238000000034 method Methods 0.000 claims description 24
150000002431 hydrogen Chemical group 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
125000002950 monocyclic group Chemical group 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 10
239000000155 melt Substances 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 10
YYQHYJBBKFEONL-UHFFFAOYSA-N C1C=CC=C2C1C1C3C1C1=C(C23)C=CC=C1 Chemical compound C1C=CC=C2C1C1C3C1C1=C(C23)C=CC=C1 YYQHYJBBKFEONL-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000005237 alkyleneamino group Chemical group 0.000 claims description 8
125000001302 tertiary amino group Chemical group 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
239000003638 chemical reducing agent Substances 0.000 claims description 4
239000000706 filtrate Substances 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
LPIFIFQXHYTBGR-UHFFFAOYSA-N tricyclo[3.3.0.02,8]octa-1(5),2(8),3,6-tetraene Chemical compound C1=CC=2C=3C2C=CC13 LPIFIFQXHYTBGR-UHFFFAOYSA-N 0.000 claims description 4
KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical class C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
150000001299 aldehydes Chemical class 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 claims description 2
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 claims description 2
YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
239000012280 lithium aluminium hydride Substances 0.000 claims description 2
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims description 2
239000002994 raw material Substances 0.000 claims description 2
238000001953 recrystallisation Methods 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
238000003756 stirring Methods 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
230000036647 reaction Effects 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 14
125000003118 aryl group Chemical group 0.000 abstract description 9
230000001430 anti-depressive effect Effects 0.000 abstract description 8
125000002252 acyl group Chemical group 0.000 abstract description 3
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract 1
PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
150000001204 N-oxides Chemical class 0.000 abstract 1
150000003863 ammonium salts Chemical class 0.000 abstract 1
150000003254 radicals Chemical class 0.000 description 18
239000000243 solution Substances 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 4
241000282693 Cercopithecidae Species 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
229940025084 amphetamine Drugs 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
230000035939 shock Effects 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
LNQUWGZAZIOHMM-UHFFFAOYSA-N ethoxy-hydroxy-methoxy-lambda3-chlorane Chemical compound CCOCl(O)OC LNQUWGZAZIOHMM-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
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 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
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LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
RATAQXOLJVRERC-UHFFFAOYSA-N 4b,4c,8b,8d-tetrahydrodibenzo[a,f]cyclopropa[cd]pentalene Chemical class C1=CC=C2C3C4=CC=CC=C4C4C3C4C2=C1 RATAQXOLJVRERC-UHFFFAOYSA-N 0.000 description 1
VWDKVBGOVYWYFZ-UHFFFAOYSA-N 9,10-dihydro-9,10-ethenoanthracene Chemical class C12=CC=CC=C2C2C=CC1C1=CC=CC=C12 VWDKVBGOVYWYFZ-UHFFFAOYSA-N 0.000 description 1
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125000006310 cycloalkyl amino group Chemical group 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
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125000005059 halophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
GDDAJHJRAKOILH-UHFFFAOYSA-N octa-2,5-diene Chemical compound CCC=CCC=CC GDDAJHJRAKOILH-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
239000000376 reactant Substances 0.000 description 1
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 1
229960003147 reserpine Drugs 0.000 description 1
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 1
150000003335 secondary amines Chemical class 0.000 description 1
230000036280 sedation Effects 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
UJTRRNALUYKHQE-UHFFFAOYSA-N sodium;diphenylmethylbenzene Chemical compound [Na+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 UJTRRNALUYKHQE-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
235000014101 wine Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/31—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by at least three rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/39—Unsaturated compounds containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C61/16—Unsaturated compounds
- C07C61/40—Unsaturated compounds containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Psychiatry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1067572A 1969-08-29 1969-10-23 Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa(cd)pentalenverbindungen. CH551364A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US85427069A	1969-08-29	1969-08-29

Publications (1)

Publication Number	Publication Date
CH551364A true CH551364A (de)	1974-07-15

Family

ID=25318202

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH1067572A CH551364A (de)	1969-08-29	1969-10-23	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa(cd)pentalenverbindungen.
CH1067972A CH551370A (de)	1969-08-29	1969-10-23	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa (cd)pentalenverbindungen.
CH1067772A CH551368A (de)	1969-08-29	1969-10-23	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa (cd)pentalenverbindungen.
CH1067372A CH551366A (de)	1969-08-29	1969-10-23	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa (cd)pentalenverbindungen.

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
CH1067972A CH551370A (de)	1969-08-29	1969-10-23	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa (cd)pentalenverbindungen.
CH1067772A CH551368A (de)	1969-08-29	1969-10-23	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa (cd)pentalenverbindungen.
CH1067372A CH551366A (de)	1969-08-29	1969-10-23	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa (cd)pentalenverbindungen.

Country Status (5)

Country	Link
JP (2)	JPS4921133B1 (fr)
AT (3)	AT305238B (fr)
CH (4)	CH551364A (fr)
OA (1)	OA03608A (fr)
SU (2)	SU420166A3 (fr)

1969
- 1969-10-23 CH CH1067572A patent/CH551364A/de not_active IP Right Cessation
- 1969-10-23 CH CH1067972A patent/CH551370A/xx not_active IP Right Cessation
- 1969-10-23 CH CH1067772A patent/CH551368A/xx not_active IP Right Cessation
- 1969-10-23 CH CH1067372A patent/CH551366A/xx not_active IP Right Cessation
- 1969-11-25 AT AT839071A patent/AT305238B/de not_active IP Right Cessation
- 1969-11-25 SU SU1709437A patent/SU420166A3/ru active
- 1969-11-25 AT AT838971A patent/AT305237B/de not_active IP Right Cessation
- 1969-11-25 SU SU1709436A patent/SU442593A3/ru active
- 1969-11-25 AT AT839271A patent/AT305972B/de not_active IP Right Cessation
- 1969-12-02 OA OA53800A patent/OA03608A/fr unknown
1971
- 1971-10-22 JP JP46083832A patent/JPS4921133B1/ja active Pending
- 1971-10-22 JP JP46083834A patent/JPS4927866B1/ja active Pending

Also Published As

Publication number	Publication date
SU420166A3 (ru)	1974-03-15
CH551366A (de)	1974-07-15
AT305237B (de)	1973-02-12
SU442593A3 (ru)	1974-09-05
AT305972B (de)	1973-03-26
JPS4921133B1 (fr)	1974-05-30
OA03608A (fr)	1971-03-30
JPS4927866B1 (fr)	1974-07-22
CH551370A (de)	1974-07-15
CH551368A (de)	1974-07-15
AT305238B (de)	1973-02-12

Legal Events

Date	Code	Title	Description
1976-05-31	PL	Patent ceased

Publication	Publication Date	Title
AT368125B (de)	1982-09-10	Verfahren zur herstellung von neuen 9-aminoalkyl- fluorenen und von deren salzen
DE2855703C2 (de)	1987-02-26	8-Substituierte 3-Fluor-10-piperazino-10,11-dihydrodibenzo[b,f]thiepine, ihre Herstellung und diese enthaltende pharmazeutische Mittel
DE2314639A1 (de)	1973-10-04	Pharmakodynamisch aktive aminoalkyloximaether
DE3225879A1 (de)	1984-01-12	Trans-3-(4'-tert.-butylcyclohexyl-1')-2-methyl-1-dialkyl-aminopropane, ihre herstellung und verwendung als arzneimittel
DE2122259A1 (de)	1971-11-18	alpha-Aminoalkyl-4-hydroxy-3-carboalkoxyaminobenzylalkohole, ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneipräparate
DE2462967C2 (de)	1982-12-02	Derivate des 3-Amino-5-methyl-2-phenyl-pyrrols, deren Salze und diese enthaltende pharmazeutische Zubereitung
CH551364A (de)	1974-07-15	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa(cd)pentalenverbindungen.
DE1695962A1 (de)	1971-05-19	(2-Aminocycloalkyl)hydrochinone und Derivate derselben sowie Verfahren zu ihrer Herstellung
DE2456098B2 (de)	1978-04-27	Xanthen- und Thioxanthen-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2253748A1 (de)	1973-05-30	Carboxamidobenzoesaeuren
AT305975B (de)	1973-03-26	Verfahren zur herstellung von neuen 4b,8b,8c,8d-tetrahydro-dibenzo(a,f)cyclopropa(c,d)pentalenverbindungen
DE2654888A1 (de)	1977-06-08	Diphenylacetamide, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CH551369A (de)	1974-07-15	Verfahren zur herstellung von 4b,8b,8c,8d-tetrahydro-dibenzo (a,f)cyclopropa (cd)pentalenverbindungen.
AT350580B (de)	1979-06-11	Verfahren zur herstellung von neuen morpholin- derivaten und deren salzen
CH540219A (de)	1973-08-15	Verfahren zur Herstellung von neuen 4b, 8b, 8c, 8d-Tetrahydro-dibenzo(a,f)cyclopropa(cd)pentalenverbindungen
AT334338B (de)	1976-01-10	Verfahren zur herstellung von neuen alpha- (1-bis-arylalkylaminoalkyl) -aralkoxybenzylalkoholen
DE2504689A1 (de)	1975-08-14	Indanderivate
DE1643265C3 (de)	1978-08-31	Kernsubstituierte 2-Aminomethylbenzhydrole, Verfahren zu deren Herstellung und Arzneimittel auf der Basis dieser Verbindungen
DE2236005C3 (de)	1976-07-08	Dibenzo- eckige Klammer auf d,f eckige Klammer zu -dioxepin- eckige Klammer auf 1,3 eckige Klammer zu -derivate und deren pharmakologisch verträgliche Salze, sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
AT334339B (de)	1976-01-10	Verfahren zur herstellung von neuen alpha- (1-bis-arylalkylaminoalkyl) -aralkoxybenzylalkoholen
AT333743B (de)	1976-12-10	Verfahren zur herstellung von neuen, basisch substituierten indanderivaten
AT360995B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
DE1695944A1 (de)	1971-05-13	Verfahren zur Herstellung neuer 1,3-Aminoalkohole
AT262255B (de)	1968-06-10	Verfahren zur Herstellung des neuen 2-(2',3',5',6'-Tetramethylbenzyl)-2-propylamins und dessen Salze
AT226710B (de)	1963-04-10	Verfahren zur Herstellung von neuen Dihydrochinoxalonen-(2) und von deren Salzen