CH493464A - Verfahren zur Herstellung von neuen Phenoxyaminopropanen - Google Patents

Verfahren zur Herstellung von neuen Phenoxyaminopropanen

Info

Publication number: CH493464A
Authority: CH; Switzerland
Prior art keywords: compounds; formula; ethanol; ether; mol
Prior art date: 1964-04-20

Application number

CH532965A

Other languages

German (de)

English (en)

Inventor

Otto Dr Thomae

Herbert Dr Koeppe

Gerhard Dr Ludwig

Anton Dr Mentrup

Karl Dr Zeile

Original Assignee

Boehringer Sohn Ingelheim

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.)

1964-04-20

Filing date

1965-04-15

Publication date

1970-07-15

1965-04-15 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1965-04-15 Priority to CH59768A priority Critical patent/CH486421A/de

1965-04-15 Priority to CH59868A priority patent/CH494735A/de

1970-07-15 Publication of CH493464A publication Critical patent/CH493464A/de

Links

MSROGRBMHWJLSB-UHFFFAOYSA-N n-phenoxypropan-1-amine Chemical class CCCNOC1=CC=CC=C1 MSROGRBMHWJLSB-UHFFFAOYSA-N 0.000 title claims description 3
230000000578 anorexic effect Effects 0.000 title 1
206010061428 decreased appetite Diseases 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
230000002829 reductive effect Effects 0.000 claims abstract description 8
239000002253 acid Substances 0.000 claims abstract description 7
150000003839 salts Chemical class 0.000 claims abstract description 5
-1 methylenedioxy Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 26
238000000034 method Methods 0.000 claims description 15
239000012279 sodium borohydride Substances 0.000 claims description 12
229910000033 sodium borohydride Inorganic materials 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 3
125000002560 nitrile group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
150000004678 hydrides Chemical class 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
238000006268 reductive amination reaction Methods 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims 1
230000003287 optical effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 8
239000002830 appetite depressant Substances 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract 2
239000002269 analeptic agent Substances 0.000 abstract 1
230000036528 appetite Effects 0.000 abstract 1
235000019789 appetite Nutrition 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 12
238000001816 cooling Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000126 substance Substances 0.000 description 6
230000005284 excitation Effects 0.000 description 5
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
239000000155 melt Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-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
230000005764 inhibitory process Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OOQWOQSMHKWCEB-UHFFFAOYSA-N 3,4-dimethyl-2-phenylmorpholine;hydron;chloride Chemical compound Cl.O1CCN(C)C(C)C1C1=CC=CC=C1 OOQWOQSMHKWCEB-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
235000021050 feed intake Nutrition 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
239000001294 propane Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
LFGYKNVJPGEVMJ-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenoxy]propan-2-one Chemical compound CC(=O)COC1=CC=CC(C(F)(F)F)=C1 LFGYKNVJPGEVMJ-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
241000700159 Rattus Species 0.000 description 1
BQIKRTGTPBOIMK-UHFFFAOYSA-N [O]C[O] Chemical compound [O]C[O] BQIKRTGTPBOIMK-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000037007 arousal Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical class C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Child & Adolescent Psychology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

CH532965A 1964-04-20 1965-04-15 Verfahren zur Herstellung von neuen Phenoxyaminopropanen CH493464A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH59768A CH486421A (de)	1964-04-20	1965-04-15	Verfahren zur Herstellung von neuen Phenoxyaminopropanen
CH59868A CH494735A (de)	1964-04-20	1965-04-15	Verfahren zur Herstellung von neuen Phenoxyaminopropanen

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB16202/64A GB1109364A (en)	1964-04-20	1964-04-20	Basic ethers

Publications (1)

Publication Number	Publication Date
CH493464A true CH493464A (de)	1970-07-15

Family

ID=10073014

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH532965A CH493464A (de)	1964-04-20	1965-04-15	Verfahren zur Herstellung von neuen Phenoxyaminopropanen

Country Status (5)

Country	Link
JP (1)	JPS4927861B1 (fr)
CH (1)	CH493464A (fr)
DE (1)	DE1493479A1 (fr)
FR (1)	FR5912M (fr)
GB (2)	GB1112839A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5688830A (en) *	1996-01-25	1997-11-18	Syntex (U.S.A.) Inc.	Treatment of neuropathic pain

1964
- 1964-04-20 GB GB55486/67A patent/GB1112839A/en not_active Expired
- 1964-04-20 GB GB16202/64A patent/GB1109364A/en not_active Expired
1965
- 1965-04-13 DE DE19651493479 patent/DE1493479A1/de active Pending
- 1965-04-15 CH CH532965A patent/CH493464A/de not_active IP Right Cessation
- 1965-04-20 FR FR13864A patent/FR5912M/fr not_active Expired
1967
- 1967-04-28 JP JP42026987A patent/JPS4927861B1/ja active Pending

Also Published As

Publication number	Publication date
GB1112839A (en)	1968-05-08
FR5912M (fr)	1968-04-01
JPS4927861B1 (fr)	1974-07-22
DE1493479A1 (de)	1972-03-30
GB1109364A (en)	1968-04-10

Legal Events

Date	Code	Title	Description
1975-11-14	PL	Patent ceased

Publication	Publication Date	Title
DE1493955B2 (de)	1976-11-18	Sulfonanilide und verfahren zu ihrer herstellung
DE1275069B (de)	1968-08-14	1-(3', 5'-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoalkane und Verfahren zu ihrer Herstellung
DE2710997B2 (de)	1979-12-06	4-Alkoxycarbonylamino-phenyläthanolamine, deren Herstellung und deren Verwendung als Arzneimittel
DE2413102B2 (de)	1980-01-17	Verfahren zur Herstellung von t-(33-Dihydroxyphenyl)-)-hydroxy-2- eckige Klammer auf l-methyl-2-(4-hydroxyphenyl)- äthyl] -aminoäthan
CH385196A (de)	1964-12-15	Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate
DE2631222A1 (de)	1978-01-19	Verfahren zur herstellung basisch substituierter phenylacetonitrile
DD216926A5 (de)	1985-01-02	Verfahren zur herstellung von neuen anhydro-aminopyridinium-hydroxid-derivaten
DE2225332A1 (de)	1972-12-14	1 eckige Klammer auf 4 Hydroxy 3 (hydroxymethyl) phenyl eckige Klammer zu 1 hydroxy 2 aralkylaminoathane
CH493464A (de)	1970-07-15	Verfahren zur Herstellung von neuen Phenoxyaminopropanen
DE1154119B (de)	1963-09-12	Verfahren zur Herstellung von 2-(2', 4', 6'-Trimethylbenzyl)-1, 3-diazacyclopenten-(2) und seinen Salzen
EP0088282A1 (fr)	1983-09-14	Dérivés d'indane, leur préparation et leur utilisation
AT260901B (de)	1968-03-25	Verfahren zur Herstellung von neuen basischen Phenoläthern und deren Additionssalzen
DE1925351A1 (de)	1969-11-27	3-Isopropylnorbornanamine und Verfahren zu ihrer Herstellung
EP0152598B1 (fr)	1988-04-20	Cyanométhyl-(2-cyano-éthyl)-(3-hydroxy-propyl)-amine et son utilisation pour la production de 1-(3-hydroxy-propyl)-1,4-diazepan et 1,4-bis-[3-(3,4,5-triméthoxy-benzoyloxy)-propyl]-diazepan
CH356121A (de)	1961-08-15	Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren
DE908138C (de)	1954-04-01	Verfahren zur Herstellung von 1-Benzyl-2-alkyl-1,2,3,4,5,6,7,8,-octa-hydroisochinolinen und ihren Salzen
DE946058C (de)	1956-07-26	Verfahren zur Herstellung von 3-Aminoindanen
AT219020B (de)	1962-01-10	Verfahren zur Herstellung von neuen N-substituierten Amino-norcamphanderivaten sowie deren Säureadditionssalzen und quaternären Ammoniumverbindungen
DE1493955C3 (de)	1977-07-14	Sulfonanilide und Verfahren zu ihrer Herstellung
DE2261914A1 (de)	1974-06-27	Neue amino-phenyl-aethanolamine und deren oxazolidine
AT266075B (de)	1968-11-11	Verfahren zur Herstellung von neuen Sulfonaniliden und deren Säureadditions- und Metallsalzen
DE1620658C (de)	1972-11-16	l-Phenyl-4-aminopyrazolderivate und Verfahren zu ihrer Herstellung
DE2132562C (de)	1973-07-26	(+) 3r N Monomethylamino 4c phenyl 4t athoxycarbonyl cyclohexen (1), dessen D bzw L O,O Dibenzoyltartrat, Hydro Chlorid bzw andere Salze physiologisch unbedenklicher Sauren und Verfahren zu deren Herstellung
AT238180B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
AT341500B (de)	1978-02-10	Verfahren zur herstellung von 1- (4-amino-3,5-dihalogen-phenyl)-2-amino-athanolen-(1)