CH507932A - Verfahren zur Herstellung basisch substituierter Cumarinderivate - Google Patents

Verfahren zur Herstellung basisch substituierter Cumarinderivate

Info

Publication number: CH507932A
Authority: CH; Switzerland
Prior art keywords: sep; formula; coumarin; derivs; alkoxy
Prior art date: 1968-01-19

Application number

CH66669A

Other languages

German (de)

English (en)

Inventor

Rudi Beyerle

Adolf Stachel

Rolf-Eberhard Nitz

Klaus Resag

Eckard Schraven

Original Assignee

Cassella Farbwerke Mainkur 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.)

1968-01-19

Filing date

1969-01-17

Publication date

1971-05-31

1968-01-19 Priority claimed from DE19681668877 external-priority patent/DE1668877C3/de

1969-01-17 Application filed by Cassella Farbwerke Mainkur Ag filed Critical Cassella Farbwerke Mainkur Ag

1971-05-31 Publication of CH507932A publication Critical patent/CH507932A/de

Links

239000003218 coronary vasodilator agent Substances 0.000 title abstract description 4
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title abstract 4
229960000956 coumarin Drugs 0.000 title abstract 2
235000001671 coumarin Nutrition 0.000 title abstract 2
150000001412 amines Chemical class 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 10
150000004775 coumarins Chemical class 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
DOBMPNYZJYQDGZ-UHFFFAOYSA-N dicoumarol Chemical compound C1=CC=CC2=C1OC(=O)C(CC=1C(OC3=CC=CC=C3C=1O)=O)=C2O DOBMPNYZJYQDGZ-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
235000015278 beef Nutrition 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 2
239000003814 drug Substances 0.000 abstract description 2
238000006480 benzoylation reaction Methods 0.000 abstract 1
150000004820 halides Chemical class 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 6
-1 γ-hydroxypropyl Chemical group 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
238000005259 measurement Methods 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229960005141 piperazine Drugs 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229940072033 potash Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
239000000047 product Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
235000002639 sodium chloride Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
ONIFCGFFEZDWSC-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]piperazine Chemical compound C1=C(OC)C(OC)=CC=C1CN1CCNCC1 ONIFCGFFEZDWSC-UHFFFAOYSA-N 0.000 description 1
CFECMQYNBQYDRQ-UHFFFAOYSA-N 1-n,1-n-diethyl-2-n-methylpropane-1,2-diamine Chemical compound CCN(CC)CC(C)NC CFECMQYNBQYDRQ-UHFFFAOYSA-N 0.000 description 1
XYXOUBBEZYLFKO-UHFFFAOYSA-N 2,3,4-trimethoxy-n-methyl-n-propan-2-ylaniline Chemical compound COC1=CC=C(N(C)C(C)C)C(OC)=C1OC XYXOUBBEZYLFKO-UHFFFAOYSA-N 0.000 description 1
HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 1
XNIOWJUQPMKCIJ-UHFFFAOYSA-N 2-(benzylamino)ethanol Chemical compound OCCNCC1=CC=CC=C1 XNIOWJUQPMKCIJ-UHFFFAOYSA-N 0.000 description 1
LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
RILLZYSZSDGYGV-UHFFFAOYSA-N 2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCCO RILLZYSZSDGYGV-UHFFFAOYSA-N 0.000 description 1
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
XBSMHLZMLQNTLY-UHFFFAOYSA-N 3,4,5-trimethoxy-n-methylaniline Chemical compound CNC1=CC(OC)=C(OC)C(OC)=C1 XBSMHLZMLQNTLY-UHFFFAOYSA-N 0.000 description 1
BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
WVZUKTGZCDSEAC-UHFFFAOYSA-N 3,4-dimethoxy-n-methyl-n-propan-2-ylaniline Chemical compound COC1=CC=C(N(C)C(C)C)C=C1OC WVZUKTGZCDSEAC-UHFFFAOYSA-N 0.000 description 1
PGBJWAKHAFOCEL-UHFFFAOYSA-N 3,4-dimethoxy-n-methylaniline Chemical compound CNC1=CC=C(OC)C(OC)=C1 PGBJWAKHAFOCEL-UHFFFAOYSA-N 0.000 description 1
KRGXWTOLFOPIKV-UHFFFAOYSA-N 3-(methylamino)propan-1-ol Chemical compound CNCCCO KRGXWTOLFOPIKV-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
XCEYKKJMLOFDSS-UHFFFAOYSA-N 4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1 XCEYKKJMLOFDSS-UHFFFAOYSA-N 0.000 description 1
JFXDIXYFXDOZIT-UHFFFAOYSA-N 4-methoxy-n-methylaniline Chemical compound CNC1=CC=C(OC)C=C1 JFXDIXYFXDOZIT-UHFFFAOYSA-N 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 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
241001465754 Metazoa Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
UHWVSEOVJBQKBE-UHFFFAOYSA-N Trimetazidine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCNCC1 UHWVSEOVJBQKBE-UHFFFAOYSA-N 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000000203 mixture Substances 0.000 description 1
MKDYQLJYEBWUIG-UHFFFAOYSA-N n',n'-diethyl-n-methylethane-1,2-diamine Chemical compound CCN(CC)CCNC MKDYQLJYEBWUIG-UHFFFAOYSA-N 0.000 description 1
NJKRFQIWDJSYOK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-piperazin-1-ylacetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCNCC1 NJKRFQIWDJSYOK-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
AAFDMAAXSJVSCP-UHFFFAOYSA-N n-methyl-2-(2,3,4-trimethoxyphenyl)ethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1OC AAFDMAAXSJVSCP-UHFFFAOYSA-N 0.000 description 1
IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 1
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH66669A 1968-01-19 1969-01-17 Verfahren zur Herstellung basisch substituierter Cumarinderivate CH507932A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19681668877 DE1668877C3 (de)	1968-01-19	1968-01-19	Basisch substituierte Cumarinderivate und deren pharmakologisch verträgliche Salze und Verfahren zu deren Herstellung

Publications (1)

Publication Number	Publication Date
CH507932A true CH507932A (de)	1971-05-31

Family

ID=5686145

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH66669A CH507932A (de)	1968-01-19	1969-01-17	Verfahren zur Herstellung basisch substituierter Cumarinderivate

Country Status (9)

Country	Link
AT (2)	AT279604B (cs)
BR (1)	BR6905654D0 (cs)
CH (1)	CH507932A (cs)
CS (2)	CS154608B2 (cs)
DK (2)	DK122608B (cs)
ES (2)	ES362656A1 (cs)
IL (1)	IL31370A (cs)
NO (1)	NO126227B (cs)
RO (1)	RO56654A (cs)

1969
- 1969-01-06 IL IL31370A patent/IL31370A/en unknown
- 1969-01-14 CS CS21269*#A patent/CS154608B2/cs unknown
- 1969-01-14 CS CS21169*#A patent/CS154607B2/cs unknown
- 1969-01-17 AT AT49469A patent/AT279604B/de not_active IP Right Cessation
- 1969-01-17 DK DK28569AA patent/DK122608B/da unknown
- 1969-01-17 DK DK28069AA patent/DK121659B/da unknown
- 1969-01-17 CH CH66669A patent/CH507932A/de not_active IP Right Cessation
- 1969-01-17 AT AT49369A patent/AT279603B/de not_active IP Right Cessation
- 1969-01-17 BR BR205654/69A patent/BR6905654D0/pt unknown
- 1969-01-18 ES ES362656A patent/ES362656A1/es not_active Expired
- 1969-01-18 RO RO58794A patent/RO56654A/ro unknown
- 1969-01-18 NO NO00203/69A patent/NO126227B/no unknown
- 1969-01-18 ES ES362657A patent/ES362657A1/es not_active Expired

Also Published As

Publication number	Publication date
CS154608B2 (cs)	1974-04-30
DK122608B (da)	1972-03-20
IL31370A (en)	1973-05-31
RO56654A (cs)	1975-01-15
AT279603B (de)	1970-03-10
BR6905654D0 (pt)	1973-02-13
ES362657A1 (es)	1970-11-16
NO126227B (cs)	1973-01-08
ES362656A1 (es)	1970-09-01
DK121659B (da)	1971-11-15
AT279604B (de)	1970-03-10
CS154607B2 (cs)	1974-04-30
IL31370A0 (en)	1969-03-27

Legal Events

Date	Code	Title	Description
1976-08-31	PL	Patent ceased

Publication	Publication Date	Title
DE2609645A1 (de)	1977-09-15	Aminoalkylheterocyclen
DE1443599A1 (de)	1968-10-24	Ungesaettigte Amine
DE2530894A1 (de)	1976-02-05	Chinanzolinderivate
DE2012138C3 (de)	1978-08-10	N{4-(ß-Pyrazin- 2-carboxyamido-äthyl)benzolsulphonyl] -N' - cycloalkylharnstoffe und diese enthaltende pharmazeutische Präparate
US2461038A (en)	1949-02-08	Chemical compositions and the preparation thereof
US2520153A (en)	1950-08-29	N-(diarylmethyl)-tertiary-aminoalkanamides and their preparation
DE1470194C3 (de)	1975-07-24	1,3,3-trisubstituierte 4-0mega-(Aminoalkyl) -2-pyrrolidinone und-2-thiopyrrolidinone
CH534687A (de)	1973-03-15	Verfahren zur Herstellung von Derivaten des 2-Oxo-1,2-dihydro-chinolins
CH507932A (de)	1971-05-31	Verfahren zur Herstellung basisch substituierter Cumarinderivate
DE1668877C3 (de)	1978-02-16	Basisch substituierte Cumarinderivate und deren pharmakologisch verträgliche Salze und Verfahren zu deren Herstellung
US3726902A (en)	1973-04-10	Furfuryl amino-coumarins
DE1215698B (de)	1966-05-05	Verfahren zur Herstellung von N'-Tricyclo[4, 3, 1, 1]-undec-3-yl-N-arylsulfonyl-harnstoffen
DE1934036A1 (de)	1971-01-07	Basisch substituierte Derivate des 2,4-(1H,3H)-Chinazolindions
US3377347A (en)	1968-04-09	Cyclobutene derivatives
CH402872A (de)	1965-11-30	Verfahren zur Herstellung von Theophyllin- oder Theobromin-Derivaten
US3772280A (en)	1973-11-13	Thiomorpholine-coumarin derivatives
DE1926075B2 (de)	1979-11-22	3-(3-Amino-3-benzoxy-propyl)-6,7,8trimethoxy-3H-lr23-benzotriazin-4-on-Derivate ihre Herstellung und Verwendung
DE1645936C (de)	1972-08-10	as-Triazino eckige Klammer auf 5,6-b eckige Klammer zu indole, ein Verfahren zu ihrer Herstellung und Arzneimittel. Ausscheidung aus: 1445454
AT151653B (de)	1937-11-25	Verfahren zur Darstellung von Perhydrocarbazolderivaten.
DE2247691A1 (de)	1974-04-11	Alkoxyzimtsaeureester basisch substituierter cumarinderivate
AT277990B (de)	1970-01-12	Verfahren zur Herstellung von neuen Cumarinderivaten
DE2310827B2 (de)	1975-10-02	Im phenylkern heterocyclisch substituierte Phenylalaninderivate
DE1668877B2 (de)	1977-06-30	Basisch substituierte cumarinderivate und deren pharmakologisch vertraegliche salze und verfahren zu deren herstellung
AT337158B (de)	1977-06-10	Verfahren zur herstellung von neuen n-(3,3-diphenylpropyl)-propylendiaminen und deren saureadditionssalzen
US2922789A (en)	1960-01-26	N-propylamide derivatives