CH436302A - Verfahren zur Herstellung 6-basisch substituierter Morphanthridine - Google Patents

Verfahren zur Herstellung 6-basisch substituierter Morphanthridine

Info

Publication number: CH436302A
Authority: CH; Switzerland
Prior art keywords: sep; formula; acid; preparation; hydrogen
Prior art date: 1963-06-14

Application number

CH741363A

Other languages

German (de)

English (en)

Inventor

Jean Dr Schmutz

Fritz Dr Hunziker

Martin Kuenzle Franz

Original Assignee

Wander Ag Dr A

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.)

1963-06-14

Filing date

1963-06-14

Publication date

1967-05-31

1963-06-14 Application filed by Wander Ag Dr A filed Critical Wander Ag Dr A

1963-06-14 Priority to CH741363A priority Critical patent/CH436302A/de

1964-02-03 Priority to AT87765A priority patent/AT248449B/de

1964-05-29 Priority to GB22367/64A priority patent/GB1006156A/en

1964-06-02 Priority to AT475064A priority patent/AT246167B/de

1964-06-02 Priority to AT87565A priority patent/AT247360B/de

1964-06-02 Priority to AT87665A priority patent/AT248448B/de

1964-06-02 Priority to DE19641470427 priority patent/DE1470427C3/de

1964-06-11 Priority to NO15363064A priority patent/NO115658B/no

1964-06-12 Priority to NL646406700A priority patent/NL140239B/xx

1964-06-12 Priority to DK86865A priority patent/DK107616C/da

1964-06-12 Priority to FR978010A priority patent/FR3490M/fr

1964-06-12 Priority to DK296164A priority patent/DK107612C/da

1964-06-12 Priority to SE718864A priority patent/SE318279B/xx

1964-06-12 Priority to SE1631665A priority patent/SE331683B/xx

1964-06-12 Priority to FI128164A priority patent/FI42561B/fi

1964-06-12 Priority to DK86765A priority patent/DK107615C/da

1964-06-12 Priority to SE1631765A priority patent/SE331684B/xx

1964-06-12 Priority to BR15998664A priority patent/BR6459986D0/pt

1964-06-13 Priority to ES300986A priority patent/ES300986A1/es

1964-06-15 Priority to BE649284A priority patent/BE649284A/xx

1965-02-19 Priority to DK86965A priority patent/DK115402B/da

1965-06-12 Priority to SE1631865A priority patent/SE331685B/xx

1966-06-02 Priority to US554670A priority patent/US3389139A/en

1967-05-31 Publication of CH436302A publication Critical patent/CH436302A/de

Links

238000000034 method Methods 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 5
239000011541 reaction mixture Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
150000001768 cations Chemical class 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
239000003208 petroleum Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
150000003951 lactams Chemical class 0.000 description 3
239000012071 phase Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000008096 xylene Substances 0.000 description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
PWRPUAKXMQAFCJ-UHFFFAOYSA-N Perlapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2CC2=CC=CC=C12 PWRPUAKXMQAFCJ-UHFFFAOYSA-N 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 2
229960001076 chlorpromazine Drugs 0.000 description 2
239000004927 clay Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000004899 motility Effects 0.000 description 2
DHSLOIFKVQGCQU-UHFFFAOYSA-N n-(10h-anthracen-9-ylidene)hydroxylamine Chemical class C1=CC=C2C(=NO)C3=CC=CC=C3CC2=C1 DHSLOIFKVQGCQU-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-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
-1 4-methyl-1-piperazinyl group Chemical group 0.000 description 1
ANVUIQDFTNLNMQ-UHFFFAOYSA-N 8-chloro-6-(4-methylpiperazin-1-yl)-11h-benzo[c][1]benzazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2CC2=CC=C(Cl)C=C12 ANVUIQDFTNLNMQ-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
238000006434 Ritter amidation reaction Methods 0.000 description 1
238000006085 Schmidt reaction Methods 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
UEDBHEFYEKZZBA-UHFFFAOYSA-N ac1np5zy Chemical compound C1=CC=[C+]=C[CH]1 UEDBHEFYEKZZBA-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
150000008425 anthrones Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000013016 damping Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
150000003571 thiolactams Chemical class 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/238—Cyclohexane rings substituted by two guanidine radicals, e.g. streptomycins

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CH741363A 1963-06-14 1963-06-14 Verfahren zur Herstellung 6-basisch substituierter Morphanthridine CH436302A (de)

Priority Applications (23)

Application Number	Priority Date	Filing Date	Title
CH741363A CH436302A (de)	1963-06-14	1963-06-14	Verfahren zur Herstellung 6-basisch substituierter Morphanthridine
AT87765A AT248449B (de)	1963-06-14	1964-02-03	Verfahren zur Herstellung von neuen, in 6-Stellung basisch substituierten Morphanthridinen
GB22367/64A GB1006156A (en)	1963-06-14	1964-05-29	6-basic substituted morphanthridines
AT475064A AT246167B (de)	1963-06-14	1964-06-02	Verfahren zur Herstellung von neuen, in 6-Stellung basisch substituierten Morphanthridinen
AT87565A AT247360B (de)	1963-06-14	1964-06-02	Verfahren zur Herstellung von neuen, in 6-Stellung basisch substituierten Morphanthridinen
AT87665A AT248448B (de)	1963-06-14	1964-06-02	Verfahren zur Herstellung von neuen, in 6-Stellung basisch substituierten Morphanthridinen
DE19641470427 DE1470427C3 (de)	1963-06-14	1964-06-02	Substituierte 6-Piperazino-morphanthridine
NO15363064A NO115658B (da)	1963-06-14	1964-06-11
NL646406700A NL140239B (nl)	1963-06-14	1964-06-12	Werkwijze ter bereiding van op de 6-plaats gesubstitueerde morfantridinen, alsmede werkwijze ter bereiding van farmaceutische preparaten en gevormde farmaceutische preparaten.
DK86865A DK107616C (da)	1963-06-14	1964-06-12	Fremgangsmåde til fremstilling af i 6-stillingen basisk substiturede morphanthridiner eller syreadditionssalte deraf.
FR978010A FR3490M (fr)	1963-06-14	1964-06-12	Morphanthridines substituées par des groupes basiques en position 6, utiles comme agents neuroplégiques, neuroleptiques et analgésiques.
DK296164A DK107612C (da)	1963-06-14	1964-06-12	Fremgangsmåde til fremstilling af i 6-stillingen basisk substituerede morphanthridiner eller syreadditionssalte deraf.
SE718864A SE318279B (da)	1963-06-14	1964-06-12
SE1631665A SE331683B (da)	1963-06-14	1964-06-12
FI128164A FI42561B (da)	1963-06-14	1964-06-12
DK86765A DK107615C (da)	1963-06-14	1964-06-12	Fremgangsmåde til fremstilling af i 6-stillingen basisk substituerede morphanthridiner eller syreadditionssalte deraf.
SE1631765A SE331684B (da)	1963-06-14	1964-06-12
BR15998664A BR6459986D0 (pt)	1963-06-14	1964-06-12	Processo para a preparacao de morfantridinas basicamente substituidas em posicao 6
ES300986A ES300986A1 (es)	1963-06-14	1964-06-13	Procedimiento para la preparación de morfantridinas 6 - básicamente sustituídas
BE649284A BE649284A (da)	1963-06-14	1964-06-15
DK86965A DK115402B (da)	1963-06-14	1965-02-19	Fremgangsmåde til fremstilling af i 6-stillingen basisk substituerede morphanthridiner eller syradditionssalte deraf.
SE1631865A SE331685B (da)	1963-06-14	1965-06-12
US554670A US3389139A (en)	1963-06-14	1966-06-02	6-homopiperazino and piperazinomorphanthridines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH741363A CH436302A (de)	1963-06-14	1963-06-14	Verfahren zur Herstellung 6-basisch substituierter Morphanthridine

Publications (1)

Publication Number	Publication Date
CH436302A true CH436302A (de)	1967-05-31

Family

ID=4324732

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH741363A CH436302A (de)	1963-06-14	1963-06-14	Verfahren zur Herstellung 6-basisch substituierter Morphanthridine

Country Status (4)

Country	Link
AT (4)	AT248449B (da)
CH (1)	CH436302A (da)
DK (3)	DK107612C (da)
ES (1)	ES300986A1 (da)

1963
- 1963-06-14 CH CH741363A patent/CH436302A/de unknown
1964
- 1964-02-03 AT AT87765A patent/AT248449B/de active
- 1964-06-02 AT AT87665A patent/AT248448B/de active
- 1964-06-02 AT AT475064A patent/AT246167B/de active
- 1964-06-02 AT AT87565A patent/AT247360B/de active
- 1964-06-12 DK DK296164A patent/DK107612C/da active
- 1964-06-12 DK DK86865A patent/DK107616C/da active
- 1964-06-12 DK DK86765A patent/DK107615C/da active
- 1964-06-13 ES ES300986A patent/ES300986A1/es not_active Expired

Also Published As

Publication number	Publication date
DK107616C (da)	1967-06-19
AT248449B (de)	1966-07-25
ES300986A1 (es)	1964-09-16
AT246167B (de)	1966-04-12
AT248448B (de)	1966-07-25
DK107615C (da)	1967-06-19
AT247360B (de)	1966-06-10
DK107612C (da)	1967-06-19

Publication	Publication Date	Title
DE2265371C3 (de)	1980-12-11	N-(3-Benzoylaminopropyl)-aniline
DE1670849B2 (de)	1977-12-01	Verfahren zur herstellung von 8-acylamino-1,2,3,4-tetrahydroisochinolinen
CH422793A (de)	1966-10-31	Verfahren zur Herstellung 11-basisch substituierter Dibenzo(b,f) (1,4)thiazepine
DE1470427C3 (de)	1975-07-03	Substituierte 6-Piperazino-morphanthridine
CH436306A (de)	1967-05-31	Verfahren zur Herstellung 6-basisch substituierter Morphanthridine
CH476753A (de)	1969-08-15	Verfahren zur Herstellung von 11-basisch substituierter Dibenzo(b,f)(1,4)thiazepine
CH436307A (de)	1967-05-31	Verfahren zur Herstellung 6-basisch substituierter Morphanthridine
CH436305A (de)	1967-05-31	Verfahren zur Herstellung 6-basisch substituierter Morphanthridine
CH450422A (de)	1968-01-31	Verfahren zur Herstellung 11-basisch substituierter Dibenz(b,f)(1,4)oxazepine
DE2600202C2 (de)	1986-08-21	Verfahren zur Herstellung von Benzodiazepinen
DE1038047B (de)	1958-09-04	Verfahren zur Herstellung von N-aminoalkylierten Iminodibenzylen und deren Salzen
CH502354A (de)	1971-01-31	Verfahren zur Herstellung von Benzodiazepin-Derivaten
DE1670162C3 (de)	1979-02-22	Verfahren zur Herstellung von 2-substituierten Phenylamino-13-diazacycloalkenen-(2) und dessen Säureadditionssalzen
AT349474B (de)	1979-04-10	Verfahren zur herstellung von neuen, basisch substituierten 3,4-dihydro-2h-isochinolin-1- thionen und ihren salzen
CH436308A (de)	1967-05-31	Verfahren zur Herstellung 6-basisch substituierter Morphanthridine
AT256825B (de)	1967-09-11	Verfahren zur Herstellung von neuen heterocyclischen Benzamidoverbindungen und ihren Salzen
DE1811831C3 (de)	1978-02-02	Verfahren zur Herstellung von 5-Phenyl-13-dihydro-2H-l,4-benzodiazepin-2-on-derivaten
AT246153B (de)	1966-04-12	Verfahren zur Herstellung von neuen Triazinverbindungen
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