CH542207A - Verfahren zur Herstellung neuer Phenylpiperidinderivate - Google Patents

Verfahren zur Herstellung neuer Phenylpiperidinderivate

Info

Publication number: CH542207A
Authority: CH; Switzerland
Prior art keywords: formula; phenyl; compounds; benzoyl; hydroxy
Prior art date: 1970-12-04

Application number

CH1793970A

Other languages

German (de)

English (en)

Inventor

Ebnoether Anton

Rissi Erwin

Original Assignee

Sandoz 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.)

1970-12-04

Filing date

1970-12-04

Publication date

1973-09-30

1970-12-04 Application filed by Sandoz Ag filed Critical Sandoz Ag

1970-12-04 Priority to CH1793970A priority Critical patent/CH542207A/de

1971-04-03 Priority to DE19712116316 priority patent/DE2116316A1/de

1971-04-06 Priority to FR7112074A priority patent/FR2092019B1/fr

1971-04-06 Priority to IE437/71A priority patent/IE35162B1/xx

1971-04-06 Priority to IL36559A priority patent/IL36559A/xx

1971-04-07 Priority to BE765443A priority patent/BE765443A/xx

1971-04-07 Priority to BG019908A priority patent/BG19152A3/bg

1971-04-07 Priority to OA54219A priority patent/OA03703A/xx

1971-04-07 Priority to SE04520/71A priority patent/SE365214B/xx

1971-04-07 Priority to CA109,831A priority patent/CA956315A/en

1971-04-08 Priority to NL7104735A priority patent/NL7104735A/xx

1971-04-08 Priority to SU1765202A priority patent/SU423295A3/ru

1972-09-01 Priority to US00285747A priority patent/US3793334A/en

1973-09-30 Publication of CH542207A publication Critical patent/CH542207A/de

Links

239000002253 acid Substances 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 35
238000000034 method Methods 0.000 claims description 12
LLSKXGRDUPMXLC-UHFFFAOYSA-N 1-phenylpiperidine Chemical class C1CCCCN1C1=CC=CC=C1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229940051803 opioid analgesics phenylpiperidine derivative Drugs 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 abstract description 13
-1 4-Benzoyl-4-hydroxy-3-phenyl-piperidino Chemical group 0.000 abstract description 7
229910052794 bromium Inorganic materials 0.000 abstract description 4
229910052801 chlorine Inorganic materials 0.000 abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
101100496169 Arabidopsis thaliana CLH1 gene Proteins 0.000 abstract 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
101100044057 Mesocricetus auratus SYCP3 gene Proteins 0.000 abstract 1
101100080600 Schizosaccharomyces pombe (strain 972 / ATCC 24843) nse6 gene Proteins 0.000 abstract 1
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
101150111293 cor-1 gene Proteins 0.000 abstract 1
125000004663 dialkyl amino group Chemical group 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
NKEJNNRTXMYMTR-UHFFFAOYSA-N (4-hydroxy-3-phenylpiperidin-4-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1(C(CNCC1)C1=CC=CC=C1)O NKEJNNRTXMYMTR-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 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
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000047 product Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
AIUGCCRGGIRXQC-UHFFFAOYSA-N (1-methyl-3-phenylpiperidin-4-yl)-phenylmethanone Chemical compound C1N(C)CCC(C(=O)C=2C=CC=CC=2)C1C1=CC=CC=C1 AIUGCCRGGIRXQC-UHFFFAOYSA-N 0.000 description 1
RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
ZYQRQLOOSVFLBC-UHFFFAOYSA-N [4-hydroxy-1-(2-hydroxyethyl)-3-phenylpiperidin-4-yl]-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1(C(CN(CC1)CCO)C1=CC=CC=C1)O ZYQRQLOOSVFLBC-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000005431 alkyl carboxamide group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/38—Halogen atoms or nitro radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/48—Oxygen atoms attached in position 4 having an acyclic carbon atom attached in position 4
- C07D211/50—Aroyl radical

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1793970A 1970-04-08 1970-12-04 Verfahren zur Herstellung neuer Phenylpiperidinderivate CH542207A (de)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CH1793970A CH542207A (de)	1970-12-04	1970-12-04	Verfahren zur Herstellung neuer Phenylpiperidinderivate
DE19712116316 DE2116316A1 (de)	1970-04-08	1971-04-03	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
FR7112074A FR2092019B1 (bg)	1970-04-08	1971-04-06
IE437/71A IE35162B1 (en)	1970-04-08	1971-04-06	Piperidine derivatives
IL36559A IL36559A (en)	1970-04-08	1971-04-06	N-substituted-4-hydroxy-4-benzoyl-3-phenyl-piperidine derivatives,their preparation and pharmaceutical compositions containing them
BE765443A BE765443A (fr)	1970-04-08	1971-04-07	Nouveaux derives de la piperidine, leur preparation et medicaments contenant ces derives
BG019908A BG19152A3 (bg)	1970-12-04	1971-04-07	Метод за получаване на хетероциклични съединения
OA54219A OA03703A (fr)	1970-04-08	1971-04-07	Nouveaux dérivés de la pipéridine et leur préparation.
SE04520/71A SE365214B (bg)	1970-04-08	1971-04-07
CA109,831A CA956315A (en)	1970-04-08	1971-04-07	4-benzoyl-4-hydroxy-3-phenyl pyridine derivatives
NL7104735A NL7104735A (bg)	1970-04-08	1971-04-08
SU1765202A SU423295A3 (ru)	1970-12-04	1971-04-08	Способ получения производных фенилпиперидина или их солей
US00285747A US3793334A (en)	1970-04-08	1972-09-01	4-benzoyl-4-hydroxy-3-phenyl-1-substituted piperidines

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1793970A CH542207A (de)	1970-12-04	1970-12-04	Verfahren zur Herstellung neuer Phenylpiperidinderivate

Publications (1)

Publication Number	Publication Date
CH542207A true CH542207A (de)	1973-09-30

Family

ID=4429225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1793970A CH542207A (de)	1970-04-08	1970-12-04	Verfahren zur Herstellung neuer Phenylpiperidinderivate

Country Status (3)

Country	Link
BG (1)	BG19152A3 (bg)
CH (1)	CH542207A (bg)
SU (1)	SU423295A3 (bg)

1970
- 1970-12-04 CH CH1793970A patent/CH542207A/de not_active IP Right Cessation
1971
- 1971-04-07 BG BG019908A patent/BG19152A3/bg unknown
- 1971-04-08 SU SU1765202A patent/SU423295A3/ru active

Also Published As

Publication number	Publication date
SU423295A3 (ru)	1974-04-05
BG19152A3 (bg)	1975-04-30

Legal Events

Date	Code	Title	Description
1977-07-15	PL	Patent ceased

Publication	Publication Date	Title
EP0579615A1 (de)	1994-01-26	Neue ester bi- und tricyclischer aminoalkohole, ihre herstellung und ihre verwendung in arzneimitteln
EP0418716A1 (de)	1991-03-27	Neue Thienylcarbonsäureester von Aminoalkoholen, ihre Quaternierungsprodukte sowie die Herstellung und Verwendung dieser Verbindungen
DE2812625A1 (de)	1978-09-28	Oximderivate der 3-acetoxymethyl-7- aminothiazolyl-acetamido-cephalosporansaeure, ihre herstellung und pharmazeutische mittel
DD148055A5 (de)	1981-05-06	Verfahren zur herstellung von o-substituierten derivaten des(+)-cyanidan-3-ols
DE2938302A1 (de)	1980-04-03	Neue derivate des 3-(aminoaethyl)- phenols und deren salze, deren herstellungsverfahren, deren verwendung als arzneimittel und die diese enthaltenden pharmazeutischen zusammensetzungen
DE2129124C3 (bg)	1974-01-10
DE1518452B2 (de)	1973-03-08	4-substituierte 2-benzhydryl-2butanol-derivate und verfahren zu ihrer herstellung
DE2128375B2 (de)	1980-06-26	Basische substituierte Alkylidenamino-oxyalkyl-carbonsäureester, deren Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE3025804C2 (de)	1985-09-05	1-S-Alkyl-2-0-acyl-3-phosphocholin-1-mercapto-2,3-propandiole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE2456082B2 (de)	1978-08-03	Substituierte Phenoxyäthanolester, Verfahren zu deren Herstellung und Schädlingsbekämpfungsmittel
EP0004260B1 (de)	1980-10-29	Substituierte Chinolizidin- und Indolizidinmethanolderivate, Verfahren zur Herstellung derselben und Arzneimittel, welche diese enthalten
DE2560602C2 (de)	1986-08-28	Sauerstoffhaltige Diarylamidine
DE2525962A1 (de)	1976-01-08	Neue heterocyclische verbindungen, ihre herstellung und verwendung
DE2265580C2 (de)	1982-11-18	Heptamethylenimino-alkyl-xanthen-9-carbonsäureester, deren Säureadditionssalze und Verfahren zu deren Herstellung, sowie Arzneimittel, welche diese enthalten
CH526546A (de)	1972-08-15	Verfahren zur Herstellung neuer 3-Phenylpiperidinderivate
CH529756A (de)	1972-10-31	Verfahren zur Herstellung neuer 3-Phenylpiperidinderivate
DE1470275C (de)	1973-04-19	Oxazohdon (2)-denvate und Ver fahren zu ihrer Herstellung
DE1770355A1 (de)	1972-03-16	Neue Morpholinderivate und Verfahren zu ihrer Herstellung
CH602766A5 (en)	1978-07-31	10-Alpha-methoxy-di:hydro-beta-ergosine derivs.
DE1620275A1 (de)	1970-03-26	Verfahren zur Herstellung von 3-Tropanyl-2-phenyl-aerylat-Verbindungen
AT238184B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
AT364836B (de)	1981-11-25	Verfahren zur herstellung von neuen o-substituierten derivaten des (+)-cyanidan-3-ols und deren salzen
AT219584B (de)	1962-02-12	Verfahren zur Herstellung neuer basischer Hydrazinverbindungen und deren Salze
AT354449B (de)	1979-01-10	Verfahren zur herstellung von neuen hydratropa- saeure-derivaten und ihren salzen
DE1795110C (de)	1973-08-16	N Substituierte 2 Methoxy 4,5 azimidobenzamide