CH389639A - Verfahren zur Herstellung von Phenylalanin-Derivaten - Google Patents

Verfahren zur Herstellung von Phenylalanin-Derivaten

Info

Publication number: CH389639A
Authority: CH; Switzerland
Prior art keywords: compound; dimethoxyphenyl; formula; acetonitrile; aqueous
Prior art date: 1960-02-29

Application number

CH225161A

Other languages

German (de)

English (en)

Inventor

Sletzinger Meyer

Floyd Reinhold Donald

Harlen Markillie John

Original Assignee

Merck & Co Inc

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.)

1960-02-29

Filing date

1961-02-24

Publication date

1965-03-31

1961-02-24 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1965-03-31 Publication of CH389639A publication Critical patent/CH389639A/de

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 5
150000002993 phenylalanine derivatives Chemical class 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 29
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
ASLSUMISAQDOOB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC ASLSUMISAQDOOB-UHFFFAOYSA-N 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 8
239000001099 ammonium carbonate Substances 0.000 claims description 8
235000012501 ammonium carbonate Nutrition 0.000 claims description 8
PGBQLBXSVSRQPF-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)butan-2-one Chemical compound CCC(=O)CC1=CC=C(OC)C(OC)=C1 PGBQLBXSVSRQPF-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
239000012736 aqueous medium Substances 0.000 claims description 5
238000010992 reflux Methods 0.000 claims description 5
-1 alkali metal cyanide Chemical class 0.000 claims description 4
150000002825 nitriles Chemical class 0.000 claims description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims 2
ANZZETGCYJWZNV-UHFFFAOYSA-N 5-[(3,4-dimethoxyphenyl)methyl]-5-ethylimidazolidine-2,4-dione Chemical compound C(C)C1(C(NC(N1)=O)=O)CC1=CC(=C(C=C1)OC)OC ANZZETGCYJWZNV-UHFFFAOYSA-N 0.000 claims 1
239000002585 base Substances 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
ZLWTZLGNRONHHR-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-oxopentanenitrile Chemical compound CCC(=O)C(C#N)C1=CC=C(OC)C(OC)=C1 ZLWTZLGNRONHHR-UHFFFAOYSA-N 0.000 description 7
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 7
235000004279 alanine Nutrition 0.000 description 7
235000019441 ethanol Nutrition 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 4
229910001863 barium hydroxide Inorganic materials 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
IUBYCVAREHLXRG-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)pentan-2-one Chemical compound CCCC(=O)CC1=CC=C(OC)C(OC)=C1 IUBYCVAREHLXRG-UHFFFAOYSA-N 0.000 description 3
HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 3
NWSHWWYXTGLXTN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-oxohexanenitrile Chemical compound CCCC(=O)C(C#N)C1=CC=C(OC)C(OC)=C1 NWSHWWYXTGLXTN-UHFFFAOYSA-N 0.000 description 3
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000007787 solid Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 2
229940091173 hydantoin Drugs 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
238000005303 weighing Methods 0.000 description 2
DARKEASZJAKOQL-ZETCQYMHSA-N (2s)-2-(3,4-dimethoxyanilino)propanoic acid Chemical compound COC1=CC=C(N[C@@H](C)C(O)=O)C=C1OC DARKEASZJAKOQL-ZETCQYMHSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
ICMAFTSLXCXHRK-UHFFFAOYSA-N Ethyl pentanoate Chemical compound CCCCC(=O)OCC ICMAFTSLXCXHRK-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
150000002148 esters Chemical class 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
238000001914 filtration Methods 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
- C07D233/78—Radicals substituted by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

CH225161A 1960-02-29 1961-02-24 Verfahren zur Herstellung von Phenylalanin-Derivaten CH389639A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US1149960A	1960-02-29	1960-02-29

Publications (1)

Publication Number	Publication Date
CH389639A true CH389639A (de)	1965-03-31

Family

ID=21750651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH225161A CH389639A (de)	1960-02-29	1961-02-24	Verfahren zur Herstellung von Phenylalanin-Derivaten

Country Status (4)

Country	Link
BE (1)	BE600673A (fr)
CH (1)	CH389639A (fr)
FR (1)	FR1450360A (fr)
GB (1)	GB945892A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1240091B (de) *	1962-07-28	1967-05-11	Bayer Ag	Verfahren zur Herstellung von alpha-Methyl-beta-(3, 4-dihydroxyphenyl)-alanin

1961
- 1961-02-22 GB GB6521/61A patent/GB945892A/en not_active Expired
- 1961-02-24 CH CH225161A patent/CH389639A/de unknown
- 1961-02-24 FR FR853804A patent/FR1450360A/fr not_active Expired
- 1961-02-27 BE BE600673A patent/BE600673A/fr unknown

Also Published As

Publication number	Publication date
GB945892A (en)	1964-01-08
BE600673A (fr)	1961-08-28
FR1450360A (fr)	1966-06-24

Publication	Publication Date	Title
DE19926233C1 (de)	2000-10-19	Verfahren zur Herstellung von Thiazolidin
DE1620501A1 (de)	1970-04-16	Neue Sydnonimin-Derivate und Verfahren zu ihrer Herstellung
DE1807887A1 (de)	1970-05-21	2,7-Diamino-6-arylpyrido [2,3-d] pyrimidinverbindungen und Verfahren zu ihrer Herstellung
DE3103372A1 (de)	1982-09-02	Neue indanyl-derivate, ihre herstellung und verwendung
CH640230A5 (de)	1983-12-30	Substituierte 2-phenylimino-imidazolidine, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben.
CH389639A (de)	1965-03-31	Verfahren zur Herstellung von Phenylalanin-Derivaten
DE2318986A1 (de)	1973-12-06	Neue penicilline
DE2462967C2 (de)	1982-12-02	Derivate des 3-Amino-5-methyl-2-phenyl-pyrrols, deren Salze und diese enthaltende pharmazeutische Zubereitung
DE2240215C3 (de)	1981-06-25	Verfahren zur Herstellung von α -[5-Indanyloxycarbonyl]-benzylpenicillin
AT225181B (de)	1963-01-10	Verfahren zur Herstellung von neuen Phenylalaninderivaten
DE1670143C3 (fr)	1974-05-30
DE1793483C3 (de)	1977-07-07	2,6-Dichlorphenylacetyl-bzw. 2,6-Dimethylphenylacetyl guanidin, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel
DE2113529C3 (de)	1980-04-30	2-(5-Nitro-2-furyl)-5-(2-alkylaminoäthoxy)-pyrimidin-Verbindungen
AT232500B (de)	1964-03-25	Verfahren zur Herstellung von neuen Phenylalaninderivaten
AT321289B (de)	1975-03-25	Verfahren zur Herstellung von neuen Diphenyläthanalkylaminen und deren Säureadditionssalzen
DE1032257B (de)	1958-06-19	Verfahren zur Herstellung neuer Hydantoine
DE1470160C (de)	1971-10-21	2-Chlor-9-piperazinopropyliden-thioxanthene und ein Verfahren zu ihrer Herstellung
AT373588B (de)	1984-02-10	Verfahren zur herstellung von neuen substituierten 1-benzoyl-2-phenylimino-imidazolidinen und von deren salzen
AT217025B (de)	1961-09-11	Verfahren zur Herstellung von neuen α-Aminoisobutyrophenonverbindungen und deren Säureadditionssalzen
AT234687B (de)	1964-07-10	Verfahren zur Herstellung von neuen Benzodioxanderivaten, sowie von deren Säureadditionssalzen
AT336572B (de)	1977-05-10	Verfahren zur herstellung von neuen alkylsulfonylaminoglycinen sowie deren salzen
AT219036B (de)	1962-01-10	Verfahren zur Herstellung von neuen 3-substituierten 1-Benzylindanen und deren Salzen
AT230364B (de)	1963-12-10	Verfahren zur Herstellung von 9,10-Dihydroanthracenen und ihren Säureadditionssalzen
AT273139B (de)	1969-08-11	Verfahren zur Herstellung von neuen 2,4,6-Triaminochinazolinen sowie von deren Säureadditionssalzen
CH398631A (de)	1966-03-15	Verfahren zur Herstellung von a-(niedrig Alkyl)-B-(3,4-dioxyphenyl)-alaninen