CH621781A5 - - Google Patents

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Publication number: CH621781A5
Authority: CH; Switzerland
Prior art keywords: radical; carbon atoms; formula; alkyl; methylidene
Prior art date: 1975-01-06

Application number

CH2176A

Other languages

German (de)

English (en)

Inventor

Junki Katsube

Atsuyuki Kojima

Makoto Sunagawa

Yoshinori Takashima

Yoshito Kameno

Hisao Yamamoto

Original Assignee

Sumitomo Chemical 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.)

1975-01-06

Filing date

1976-01-05

Publication date

1981-02-27

1975-01-06 Priority claimed from JP454075A external-priority patent/JPS5817469B2/ja

1975-06-04 Priority claimed from JP6776775A external-priority patent/JPS51143679A/ja

1976-01-05 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1981-02-27 Publication of CH621781A5 publication Critical patent/CH621781A5/de

Links

-1 alkyl radical Chemical group 0.000 claims description 116
125000004432 carbon atom Chemical group C* 0.000 claims description 78
150000001875 compounds Chemical class 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 19
150000003254 radicals Chemical class 0.000 claims description 19
238000000034 method Methods 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
238000009833 condensation Methods 0.000 claims description 10
230000005494 condensation Effects 0.000 claims description 10
231100000252 nontoxic Toxicity 0.000 claims description 9
230000003000 nontoxic effect Effects 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000006684 polyhaloalkyl group Polymers 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
150000001728 carbonyl compounds Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
WRXDYGKMJYHHHY-UHFFFAOYSA-N 2-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidenemethyl)morpholine Chemical compound C1NCCOC1C=C1C2=CC=CC=C2C=CC2=CC=CC=C21 WRXDYGKMJYHHHY-UHFFFAOYSA-N 0.000 claims description 3
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical compound C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
230000020335 dealkylation Effects 0.000 claims description 3
238000006900 dealkylation reaction Methods 0.000 claims description 3
230000008707 rearrangement Effects 0.000 claims description 3
230000002829 reductive effect Effects 0.000 claims description 3
ZQYUVRODZFKULG-UHFFFAOYSA-N 2-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidenemethyl)-4-methylmorpholine Chemical compound C1N(C)CCOC1C=C1C2=CC=CC=C2C=CC2=CC=CC=C21 ZQYUVRODZFKULG-UHFFFAOYSA-N 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
COLOHWPRNRVWPI-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound [CH2]C(F)(F)F COLOHWPRNRVWPI-UHFFFAOYSA-N 0.000 claims 1
IGHWKTWWNJNJIH-UHFFFAOYSA-N 2-(9-methylidene-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)morpholine Chemical compound N1CC(OCC1)C1C2=C(C(CC3=C1C=CC=C3)=C)C=CC=C2 IGHWKTWWNJNJIH-UHFFFAOYSA-N 0.000 claims 1
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims 1
150000005840 aryl radicals Chemical class 0.000 claims 1
RMCDUNHIVVEEDD-UHFFFAOYSA-N methylcyclopropane Chemical compound [CH2]C1CC1 RMCDUNHIVVEEDD-UHFFFAOYSA-N 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 claims 1
231100000331 toxic Toxicity 0.000 claims 1
230000002588 toxic effect Effects 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 17
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
238000000354 decomposition reaction Methods 0.000 description 10
239000012442 inert solvent Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000002585 base Substances 0.000 description 5
239000002026 chloroform extract Substances 0.000 description 5
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 4
238000006243 chemical reaction Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
239000000935 antidepressant agent Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
229940005513 antidepressants Drugs 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 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
230000037396 body weight Effects 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052987 metal hydride Inorganic materials 0.000 description 2
150000004681 metal hydrides Chemical class 0.000 description 2
229910000000 metal hydroxide Inorganic materials 0.000 description 2
150000004692 metal hydroxides Chemical class 0.000 description 2
150000002780 morpholines Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-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
GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical class C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
SRTMGQXUCMILBQ-UHFFFAOYSA-N 11-methylidene-5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulene Chemical compound C1CC2=CC=CC=C2C(=C)C2=CC=CC=C21 SRTMGQXUCMILBQ-UHFFFAOYSA-N 0.000 description 1
GOIWZZQXWJVDOG-UHFFFAOYSA-N 2,2,2-trifluoroethyl trichloromethanesulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(Cl)(Cl)Cl GOIWZZQXWJVDOG-UHFFFAOYSA-N 0.000 description 1
OEGMNXUJXBHKLQ-UHFFFAOYSA-N 2-(1-methyl-9H-thioxanthen-9-yl)-4-propan-2-ylmorpholine Chemical compound C(C)(C)N1CC(OCC1)C1C2=CC=CC=C2SC=2C=CC=C(C1=2)C OEGMNXUJXBHKLQ-UHFFFAOYSA-N 0.000 description 1
JGSNVMBWRRNCDC-UHFFFAOYSA-N 2-(1-methyl-9H-xanthen-9-yl)morpholine Chemical compound N1CC(OCC1)C1C2=CC=CC=C2OC=2C=CC=C(C12)C JGSNVMBWRRNCDC-UHFFFAOYSA-N 0.000 description 1
MXBSIGICMQHKJT-UHFFFAOYSA-N 2-(2-chloro-10-methylidene-9H-thioxanthen-9-yl)-4-methylmorpholine Chemical compound ClC1=CC=2C(C3=CC=CC=C3S(C=2C=C1)=C)C1CN(CCO1)C MXBSIGICMQHKJT-UHFFFAOYSA-N 0.000 description 1
NISIKGYFNOTZEO-UHFFFAOYSA-N 2-(7-methyl-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)morpholine Chemical compound N1CC(OCC1)C1C2=C(C=CC3=C1C=CC=C3C)C=CC=C2 NISIKGYFNOTZEO-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
FMIYMWFMEHHJBH-UHFFFAOYSA-N 2-[2-(9-methylidene-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)morpholin-4-yl]ethanol Chemical compound OCCN1CC(OCC1)C1C2=C(C(CC3=C1C=CC=C3)=C)C=CC=C2 FMIYMWFMEHHJBH-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
PZBBIQDESDCRBM-UHFFFAOYSA-N 4-benzyl-2-(1-methyl-9H-xanthen-9-yl)morpholine Chemical compound C(C1=CC=CC=C1)N1CC(OCC1)C1C2=CC=CC=C2OC=2C=CC=C(C12)C PZBBIQDESDCRBM-UHFFFAOYSA-N 0.000 description 1
XHNRPVAMGLPCDV-UHFFFAOYSA-N 4-benzyl-2-(5,6-dihydrodibenzo[1,2-a:1',2'-e][7]annulen-11-ylidenemethyl)morpholine Chemical compound C1COC(C=C2C3=CC=CC=C3CCC3=CC=CC=C32)CN1CC1=CC=CC=C1 XHNRPVAMGLPCDV-UHFFFAOYSA-N 0.000 description 1
OBSKUZUKHWYITA-UHFFFAOYSA-N 4-benzyl-2-(7-methyl-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)morpholine Chemical compound C(C1=CC=CC=C1)N1CC(OCC1)C1C2=C(C=CC3=C1C=CC=C3C)C=CC=C2 OBSKUZUKHWYITA-UHFFFAOYSA-N 0.000 description 1
LPFNLAIQNLLFMN-UHFFFAOYSA-N 4-benzyl-2-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidenemethyl)morpholine Chemical compound C1COC(C=C2C3=CC=CC=C3C=CC3=CC=CC=C32)CN1CC1=CC=CC=C1 LPFNLAIQNLLFMN-UHFFFAOYSA-N 0.000 description 1
RDPPCNAQFHVVSN-UHFFFAOYSA-N 4-methyl-2-(7-methyl-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenyl)morpholine Chemical compound CN1CC(OCC1)C1C2=C(C=CC3=C1C=CC=C3C)C=CC=C2 RDPPCNAQFHVVSN-UHFFFAOYSA-N 0.000 description 1
VKRQIGXFKMQTJR-UHFFFAOYSA-N 4-methyl-2-(9-methylidene-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl)morpholine Chemical compound C1N(C)CCOC1C1C2=CC=CC=C2C(=C)CC2=CC=CC=C21 VKRQIGXFKMQTJR-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
241000251730 Chondrichthyes Species 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
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 1
101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
238000003833 Wallach reaction Methods 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
231100001259 acute cardiotoxicity Toxicity 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
229960000836 amitriptyline Drugs 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
QLFNUXTWJGXNLH-UHFFFAOYSA-N bis(2-methoxyethoxy)alumane Chemical compound COCCO[AlH]OCCOC QLFNUXTWJGXNLH-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UFKDESIUZHMUGL-UHFFFAOYSA-N boron;formonitrile;sodium Chemical compound [B].[Na].N#C UFKDESIUZHMUGL-UHFFFAOYSA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000003001 depressive effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 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
229910017604 nitric acid Inorganic materials 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 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
238000007363 ring formation reaction Methods 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
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
101150035983 str1 gene Proteins 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/10—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH2176A 1975-01-06 1976-01-05 CH621781A5 (xx)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP454075A JPS5817469B2 (ja)	1975-01-06	1975-01-06	シンキナモルホリンユウドウタイノシンキセイゾウホウ
JP6776775A JPS51143679A (en)	1975-06-04	1975-06-04	A new process for preparing novel morpholine derivatives

Publications (1)

Publication Number	Publication Date
CH621781A5 true CH621781A5 (xx)	1981-02-27

Family

ID=26338346

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH2176A CH621781A5 (xx)	1975-01-06	1976-01-05
CH579880A CH623816A5 (xx)	1975-01-06	1980-07-29

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH579880A CH623816A5 (xx)	1975-01-06	1980-07-29

Country Status (18)

Country	Link
US (1)	US4085210A (xx)
AR (2)	AR213280A1 (xx)
AT (1)	AT346353B (xx)
AU (1)	AU498463B2 (xx)
BE (1)	BE837341A (xx)
CA (1)	CA1065310A (xx)
CH (2)	CH621781A5 (xx)
CS (1)	CS189735B2 (xx)
DE (1)	DE2600358A1 (xx)
DK (1)	DK2476A (xx)
ES (1)	ES444101A1 (xx)
FI (1)	FI753701A (xx)
FR (1)	FR2296412A1 (xx)
GB (1)	GB1501321A (xx)
NL (1)	NL7600096A (xx)
NO (1)	NO145197C (xx)
PL (1)	PL98488B1 (xx)
SE (1)	SE7514779L (xx)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4169146A (en) *	1975-01-06	1979-09-25	Sumitomo Chemical Company, Limited	Novel morpholine derivatives and treating depression therewith
WO1993015052A1 (en) *	1992-01-28	1993-08-05	Smithkline Beecham Plc	Compounds as calcium channel antagonists
WO1999047517A1 (en) *	1998-03-17	1999-09-23	Novo Nordisk A/S	Novel heterocyclic compounds
US6214816B1 (en) *	1998-03-17	2001-04-10	Novo Nordisk A/S	Heterocyclic compounds
US7294637B2 (en)	2000-09-11	2007-11-13	Sepracor, Inc.	Method of treating addiction or dependence using a ligand for a monamine receptor or transporter
US7517892B2 (en)	2000-09-11	2009-04-14	Sepracor Inc.	Ligands for monoamine receptors and transporters, and methods of use thereof
TW200400816A (en) *	2002-06-26	2004-01-16	Lilly Co Eli	Tricyclic steroid hormone nuclear receptor modulators

1975
- 1975-12-30 FI FI753701A patent/FI753701A/fi not_active Application Discontinuation
- 1975-12-30 SE SE7514779A patent/SE7514779L/xx not_active Application Discontinuation
1976
- 1976-01-04 CS CS7636A patent/CS189735B2/cs unknown
- 1976-01-05 FR FR7600106A patent/FR2296412A1/fr active Granted
- 1976-01-05 DK DK2476*#A patent/DK2476A/da not_active Application Discontinuation
- 1976-01-05 CA CA242,957A patent/CA1065310A/en not_active Expired
- 1976-01-05 AU AU10020/76A patent/AU498463B2/en not_active Expired
- 1976-01-05 NO NO760018A patent/NO145197C/no unknown
- 1976-01-05 AT AT2276A patent/AT346353B/de not_active IP Right Cessation
- 1976-01-05 GB GB224/76A patent/GB1501321A/en not_active Expired
- 1976-01-05 AR AR261847A patent/AR213280A1/es active
- 1976-01-05 CH CH2176A patent/CH621781A5/de not_active IP Right Cessation
- 1976-01-05 PL PL1976186338A patent/PL98488B1/pl unknown
- 1976-01-05 ES ES444101A patent/ES444101A1/es not_active Expired
- 1976-01-06 NL NL7600096A patent/NL7600096A/xx not_active Application Discontinuation
- 1976-01-06 US US05/646,908 patent/US4085210A/en not_active Expired - Lifetime
- 1976-01-06 BE BE163339A patent/BE837341A/xx unknown
- 1976-01-07 DE DE19762600358 patent/DE2600358A1/de not_active Withdrawn
- 1976-09-28 AR AR264895A patent/AR212816A1/es active
1980
- 1980-07-29 CH CH579880A patent/CH623816A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE2600358A1 (de)	1976-07-08
GB1501321A (en)	1978-02-15
BE837341A (fr)	1976-07-06
AR212816A1 (es)	1978-10-13
AU498463B2 (en)	1979-03-15
CA1065310A (en)	1979-10-30
NL7600096A (nl)	1976-07-08
ES444101A1 (es)	1977-07-16
SE7514779L (sv)	1976-07-07
AR213280A1 (es)	1979-01-15
CH623816A5 (xx)	1981-06-30
ATA2276A (de)	1978-03-15
CS189735B2 (en)	1979-04-30
DK2476A (da)	1976-07-07
NO145197B (no)	1981-10-26
US4085210A (en)	1978-04-18
PL98488B1 (pl)	1978-05-31
FI753701A (xx)	1976-07-07
FR2296412B1 (xx)	1981-12-31
AT346353B (de)	1978-11-10
NO760018L (xx)	1976-07-07
FR2296412A1 (fr)	1976-07-30
AU1002076A (en)	1977-07-14
NO145197C (no)	1982-02-03

Publication	Publication Date	Title
DE69914594T2 (de)	2004-12-09	Aryl-annellierte azapolycyclische verbindungen
DE1620198C3 (de)	1975-05-28	5H-Benz eckige Klammer auf f eckige Klammer zu 2,5-oxazocine oder Benz eckige Klammer auf g eckige Klammer zu 2,6-oxazonine, ihre Salze und Arzneimittel
CH637935A5 (de)	1983-08-31	Verfahren zur herstellung neuer derivate von perhydro-aza-heterocyclen.
DE3002367A1 (de)	1980-07-24	2-substituierte trans-5-aryl-2,3,4,4a,5, 9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole
CH621781A5 (xx)	1981-02-27
DE1543777C3 (de)	1974-05-16	Verfahren zur Herstellung von alpha-niedrig Alkyl-beta-(4-hydroxyphenyl)-alaninen
DE10235312A1 (de)	2004-02-12	Verfahren zur Herstellung von Aminoalkoxybenzylaminen und Aminoalkoxybenzonitrilen als Zwischenprodukte
DE2726836A1 (de)	1977-12-29	6,7-benzomorphane, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel
CH615412A5 (xx)	1980-01-31
CH638784A5 (de)	1983-10-14	Verfahren zur herstellung neuer phenylazacycloalkane.
DE2526966A1 (de)	1976-01-08	Tricyclische alkylaminverbindungen, verfahren zu ihrer herstellung und sie enthaltende mittel
CH622792A5 (xx)	1981-04-30
DE2630587A1 (de)	1977-01-27	Morpholinderivate, verfahren zu ihrer herstellung und arzneimittel
AT350580B (de)	1979-06-11	Verfahren zur herstellung von neuen morpholin- derivaten und deren salzen
CH617920A5 (xx)	1980-06-30
DE1190463B (de)	1965-04-08	Verfahren zur Herstellung von neuen N, N'-substituierten Diaminoaethylenverbindungenoder deren Salzen mit physiologisch vertraeglichen Saeuren
CH383998A (de)	1964-11-15	Verfahren zur Herstellung neuer sekundärer Amine
DE2340160A1 (de)	1974-02-21	Norbornanderivate
DE2039396A1 (de)	1971-02-18	Neue Dibenzazepinderivate und ihre Herstellung
DE2422309C3 (de)	1977-05-18	2,3,4,5,6,7-Hexahydro-1,6-methano-1 H-4-Penzazonin- Derivate
DE1470161C (de)	1973-06-20	5 (gamma Alkylammopropyl) 5, 7 dihydro 6H dibenzo eckige Klammer auf d,f eckige Klammer zu eckige Klammer auf 1,3 eckige Klammer zu diazepm 6 on derivate
AT363094B (de)	1981-07-10	Verfahren zur herstellung von neuen piperazinderivaten und deren salzen
AT205038B (de)	1959-08-25	Verfahren zur Herstellung neuer, in 10-Stellung substituierter 11-Oxo-dibenzo-[b, f]-thia-[1]-aza-[4]-cycloheptadien-[2,6]-Verbindungen
DE19720475A1 (de)	1998-11-19	Verfahren zur Herstellung von N-Alkyl-2,6-dialkyl-morpholinen
DE1793611B2 (de)	1973-06-07	4,4-diphenylcyclohexylamine, ihre saeureadditionssalze und quartaeren ammoniumsalze

Legal Events

Date	Code	Title	Description
1983-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased