AT262964B - Process for the preparation of basic substituted O-ethers of 10,11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oxime - Google Patents
Process for the preparation of basic substituted O-ethers of 10,11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oximeInfo
- Publication number
- AT262964B AT262964B AT1065365A AT1065365A AT262964B AT 262964 B AT262964 B AT 262964B AT 1065365 A AT1065365 A AT 1065365A AT 1065365 A AT1065365 A AT 1065365A AT 262964 B AT262964 B AT 262964B
- Authority
- AT
- Austria
- Prior art keywords
- cyclohepten
- dibenzo
- oxime
- dihydro
- starting substances
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- BYNLMOBUYHLZQC-UHFFFAOYSA-N n-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylidene)hydroxylamine Chemical compound C1CC2=CC=CC=C2C(=NO)C2=CC=CC=C21 BYNLMOBUYHLZQC-UHFFFAOYSA-N 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- YFBQXUGQIFAFMM-UHFFFAOYSA-N 2-chloro-n-methylethanamine Chemical compound CNCCCl YFBQXUGQIFAFMM-UHFFFAOYSA-N 0.000 claims description 2
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003277 amino 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
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 3
- AUERUDPETOKUPT-UHFFFAOYSA-N 1-(3-chloropropyl)-4-methylpiperazine Chemical compound CN1CCN(CCCCl)CC1 AUERUDPETOKUPT-UHFFFAOYSA-N 0.000 claims 1
- HDDNBUNZJIQDBQ-UHFFFAOYSA-N 1-(3-chloropropyl)piperidine Chemical compound ClCCCN1CCCCC1 HDDNBUNZJIQDBQ-UHFFFAOYSA-N 0.000 claims 1
- 150000002366 halogen compounds Chemical class 0.000 claims 1
- 150000002443 hydroxylamines Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- -1 β-diethylaminoethyl-O-ether Chemical compound 0.000 description 2
- CQGJLKXZDHEZSZ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxyperoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOOOCCN(C)C CQGJLKXZDHEZSZ-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 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
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003270 anti-cataleptic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- HDHCLUGKRJBUBL-UHFFFAOYSA-N o-[2-(diethylamino)ethyl]hydroxylamine Chemical compound CCN(CC)CCON HDHCLUGKRJBUBL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung von basisch substituierten O-thern des l0, ll-Dihydro-5H- dibenzo [a, d] cyclohepten-5-on-oxims
EMI1.1
EMI1.2
in der A für eine verzweigte oder unverzweigte Alkylenkette mit bis zu 6 C-Atomen steht, Ri und R, Wasserstoff oder einen Alkylrest mit 1-8 C-Atomen bedeuten, die gegebenenfalls auch über ein Heteroatom wie N, S oder 0 miteinander oder mit A verbunden sein können, Rs und R4 Wasserstoff, Alkylgruppen mit 1-4 C-Atomen, Halogen, Hydroxy, Nitro oder Aminogruppen bedeuten und n für die Zahlen 1 oder 2 steht, wertvolle pharmakologische Eigenschaften besitzen.
Die Verbindungen haben im Tierexperiment als solche oder in Form ihrer Salze mit nichttoxischen anorganischen oder organischen Säuren starke antikataleptische Wirkungen gegenüber pharmakogen bewirkten extrapyramidal-motorischen Reizzuständen.
Sie sind weiterhin wirksam in verschiedenen tierexperimentellen Versuchsanordnungen, die Hinweise für antidepressive (thymoleptische) Wirkungsqualitäten beim Menschen geben.
Die Verbindungen sind, ausserdem in vitro stark spasmolytisch wirksam.
Zur Salzbildung geeignete nichttoxische Säuren sind z. B. Essigsäure, Propionsäure, Milchsäure, Maleinsäure, Fumarsäure, Bernsteinsäure, Weinsäure, Zitronensäure, Salicylsäure, Naphthalin-I, 5-disulfo- säure, Phosphorsäure, Salzsäure usw.
EMI1.3
EMI1.4
EMI1.5
EMI1.6
<Desc/Clms Page number 2>
1l-Dihydro-5H-Dibenzo[a, d]cyc1oheptenoneumsetzt, oder erst mit Hydroxylamin in die Oxime der allgemeinen Formel
EMI2.1
überführt und diese in Form geeigneter Metallsalze mit Halogeniden der allgemeinen Formel
EMI2.2
reagieren lässt. In diesen Formeln haben A, RI, R, Ra, R4 und n die oben angegebene Bedeutung.
Beispiel 1 : 2, 08 g 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-on und 1, 5 ml ss-Diäthylamino- äthoxyamin werden in 2 ml Methanol gelöst. Man setzt methanolische Salzsäure hinzu bis ein PH von 3 bis 4 erreicht ist und kocht über Nacht unter Rückfluss. Anschliessend wird zur Trockne eingedampft, der Rückstand mit Äther angerieben und abgesaugt. Man löst den festen Rückstand in Wasser, stellt alkalisch und trennt das ausfallende Öl ab, das man in Äther mit ätherischer Salzsäure in das Hydrochlorid überführt. Schliesslich wird das Hydrochlorid des ss-Diäthylaminoäthyl-O-Äthers des 10, 11-Di- hydro-5H-dibenzo [a, d] cyclohepten-5-on-oxims durch Umkristallisieren aus Aceton gereinigt, Fp. 169 bis 171 0 C.
Beispiel 2 : 1, 15 g Natrium werden in 100 ml absolutem Äthanol gelöst. Man trägt portionsweise 11, 2 g 5-Oximino-10,11-Dihydro-5H-Dibenzo[a,d]cyclohepten ein und kocht kurz auf. Anschliessend tropft man 6, 4 g ss-Dimethylaminoäthylchlorid ein und kocht vier Stunden unter Rückfluss. Das Lösungsmittel wird abgezogen, der Rückstand in Benzol aufgenommen und erneut zur Trockene eingeengt.
Der Rückstand wird wiederum in Benzol gelöst und an Aluminiumoxyd (nach Brockmann) chromatographiert. Die ersten Benzolfraktionen enthalten 7 g des ss-Dimethylaminoäthyl-O-Äthers des 10, 11-Di- hydro-5H-dibenzo[a, d]cyclohepten-5-on-oxims, dessen Hydrochlorid man aus Aceton mit ätherischer Salzsäure fällt.
EMI2.3
C.hydro-5H-dibenzo[a,d]cyclohepten-5-on-oxims ein und gibt anschliessend eine Lösung von 6, 5 g ss-Methyl- aminoäthy1chlorid in absolutem Äthanol hinzu und rührt eine Stunde bei Raumtemperatur. Anschliessend wird über Nacht auf 600 C erwärmt und schliesslich eineinhalb Stunden unter Rückfluss gekocht. Man saugt ab, dampft das Filtrat ein und behandelt den Rückstand mit Cyclohexan.
Der Cyclohexanauszug wird mit ätherischer Salzsäure versetzt und das ausgefallene Hydrochlorid des ss-Methylamino-äthyl-O- Äthers des 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-on-oxims nach dem Abdekantieren des Lösungsmittels aus Aceton umkristallisiert, Fp. 1960 C.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of basic substituted O-ethers of l0, ll-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oxime
EMI1.1
EMI1.2
in which A stands for a branched or unbranched alkylene chain with up to 6 carbon atoms, Ri and R, hydrogen or an alkyl radical with 1-8 carbon atoms, which optionally also have a heteroatom such as N, S or 0 with each other or with A can be linked, Rs and R4 are hydrogen, alkyl groups with 1-4 C atoms, halogen, hydroxy, nitro or amino groups and n is the numbers 1 or 2, have valuable pharmacological properties.
In animal experiments, as such or in the form of their salts with non-toxic inorganic or organic acids, the compounds have strong anticataleptic effects against pharmacogenically induced extrapyramidal motor irritation.
They are still effective in various animal experiments which give indications of antidepressant (thymoleptic) qualities in humans.
The compounds are also strongly spasmolytic in vitro.
Non-toxic acids suitable for salt formation are e.g. B. acetic acid, propionic acid, lactic acid, maleic acid, fumaric acid, succinic acid, tartaric acid, citric acid, salicylic acid, naphthalene-1,5-disulfonic acid, phosphoric acid, hydrochloric acid, etc.
EMI1.3
EMI1.4
EMI1.5
EMI1.6
<Desc / Clms Page number 2>
1l-dihydro-5H-dibenzo [a, d] cyc1oheptenone reacted, or only with hydroxylamine in the oximes of the general formula
EMI2.1
converted and these in the form of suitable metal salts with halides of the general formula
EMI2.2
lets react. In these formulas, A, RI, R, Ra, R4 and n have the meanings given above.
Example 1: 2.08 g of 10,11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one and 1.5 ml of β-diethylaminoethoxyamine are dissolved in 2 ml of methanol. Methanolic hydrochloric acid is added until a pH of 3 to 4 is reached and the mixture is refluxed overnight. It is then evaporated to dryness, the residue rubbed with ether and filtered off with suction. The solid residue is dissolved in water, made alkaline and the precipitated oil is separated off, which is converted into the hydrochloride in ether with ethereal hydrochloric acid. Finally, the hydrochloride of the β-diethylaminoethyl-O-ether of 10, 11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oxime is purified by recrystallization from acetone, melting point 169 to 171 ° C.
Example 2: 1.15 g of sodium are dissolved in 100 ml of absolute ethanol. 11.2 g of 5-oximino-10,11-dihydro-5H-dibenzo [a, d] cycloheptene are added in portions and the mixture is briefly boiled. Then 6.4 g of ss-dimethylaminoethyl chloride are added dropwise and the mixture is refluxed for four hours. The solvent is stripped off, the residue is taken up in benzene and again concentrated to dryness.
The residue is again dissolved in benzene and chromatographed on aluminum oxide (according to Brockmann). The first benzene fractions contain 7 g of the β-dimethylaminoethyl-O-ether of 10, 11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oxime, the hydrochloride of which is precipitated from acetone with ethereal hydrochloric acid.
EMI2.3
C.hydro-5H-dibenzo [a, d] cyclohepten-5-one oxime and then a solution of 6.5 g of β-methylaminoethyl chloride in absolute ethanol is added and the mixture is stirred for one hour at room temperature. The mixture is then heated to 600 ° C. overnight and finally refluxed for one and a half hours. It is filtered off with suction, the filtrate is evaporated and the residue is treated with cyclohexane.
The cyclohexane extract is mixed with ethereal hydrochloric acid and the precipitated hydrochloride of the β-methylamino-ethyl-O-ether of 10,11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oxime after decanting off the solvent from acetone recrystallized, m.p. 1960 C.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE262964T | 1964-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT262964B true AT262964B (en) | 1968-07-10 |
Family
ID=29751444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT1065365A AT262964B (en) | 1964-11-26 | 1965-11-26 | Process for the preparation of basic substituted O-ethers of 10,11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oxime |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT262964B (en) |
-
1965
- 1965-11-26 AT AT1065365A patent/AT262964B/en active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AT262964B (en) | Process for the preparation of basic substituted O-ethers of 10,11-dihydro-5H-dibenzo [a, d] cyclohepten-5-one oxime | |
| CH520117A (en) | 5h-dibenzo-a d-10 11-dihydro-cyclohepten-5-one oximes | |
| DE1543388B1 (en) | Basically substituted, tricyclic heterocyclic compounds and their pharmacologically non-toxic salts and processes for their preparation | |
| DE1937526B2 (en) | PROCESS FOR PRODUCING SUBSTITUTED PHENYLAMINE | |
| AT148476B (en) | Process for introducing aminoalkyl groups into the amino groups of amines. | |
| AT234104B (en) | Process for the production of new indolyl derivatives and their acid salts | |
| AT214918B (en) | Process for the preparation of new, substituted benzimidazoles and their acid addition salts | |
| AT160652B (en) | Process for the preparation of oxyketones of the cyclopentanopolyhydrophenanthrene series. | |
| AT233016B (en) | Process for the preparation of new iminodibenzyl derivatives | |
| AT225176B (en) | Process for the preparation of new hydrazine derivatives | |
| AT343814B (en) | PROCESS FOR THE PREPARATION OF NEW 9-ALKYLAMINO-ERYTHROMYCINE AND THEIR SALT | |
| AT218518B (en) | Process for the preparation of new alkyl-substituted, basic tetralone derivatives | |
| AT202133B (en) | Process for the preparation of mixed, secondary amines and their salts | |
| AT266101B (en) | Process for the preparation of new basic substituted naphthalene- (1,4,5,8) -tetracarboxylic acid diimides | |
| AT238167B (en) | Process for the preparation of N- (2,3-dimethylphenyl) anthranilic acid and its salts | |
| DE954155C (en) | Process for the preparation of 4-aminochromans | |
| DE924212C (en) | Process for the preparation of ring-substituted ª -oxypyruvic acids or their derivatives | |
| AT203497B (en) | Process for the production of new diphenylmethane derivatives, their acid salts and quaternary salts | |
| AT230882B (en) | Process for the production of 6-aminochryses | |
| AT319213B (en) | Process for the production of new β-phenyl fatty acids and their esters, amides or salts | |
| AT216496B (en) | Process for the preparation of new α-substituted glycine derivatives | |
| AT200134B (en) | Process for the preparation of a-amino-b-oxycarboxamides | |
| AT226888B (en) | Process for the production of nordihydrotoxiferin and its quaternization products | |
| AT202134B (en) | Process for the preparation of mixed, secondary amines and their salts | |
| AT227686B (en) | Process for the production of new anthranilic acids and their salts |