CH509327A - Verfahren zur Herstellung von am Kohlenstoff des Heterocyclus alkylierten N,N'-disubstituierten Diazacycloalkanen - Google Patents

Verfahren zur Herstellung von am Kohlenstoff des Heterocyclus alkylierten N,N'-disubstituierten Diazacycloalkanen

Info

Publication number: CH509327A
Authority: CH; Switzerland
Prior art keywords: formula; compound; mol; methyl; hydrogen
Prior art date: 1967-12-06

Application number

CH1725968A

Other languages

German (de)

English (en)

Inventor

Habil Arnold Herbert Dr Phil

Norbert Dr Med Brock

Habil Lenke Hans-Dieter Dr Vet

Klaus Dr Molge

Rolf Dr Rebling

Dietrich Dr Vogelsang

Original Assignee

Asta Werke Ag Chem Fab

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.)

1967-12-06

Filing date

1968-11-19

Publication date

1971-06-30

1968-11-19 Application filed by Asta Werke Ag Chem Fab filed Critical Asta Werke Ag Chem Fab

1971-06-30 Publication of CH509327A publication Critical patent/CH509327A/de

Links

239000002253 acid Substances 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 13
150000001875 compounds Chemical class 0.000 claims description 34
239000002585 base Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
-1 alkaline earth metal cation Chemical class 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
230000000144 pharmacologic effect Effects 0.000 claims description 3
SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical class COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical class O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
230000000916 dilatatory effect Effects 0.000 abstract description 3
JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract 2
150000007513 acids Chemical class 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
239000000243 solution Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
LCAUMHWMXSOPCJ-UHFFFAOYSA-N 3-chloropropyl 3,4,5-trimethoxybenzoate Chemical compound COC1=CC(C(=O)OCCCCl)=CC(OC)=C1OC LCAUMHWMXSOPCJ-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 5
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
KRQAMFQCSAJCRH-UHFFFAOYSA-N hexobendine Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OCCCN(C)CCN(C)CCCOC(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 KRQAMFQCSAJCRH-UHFFFAOYSA-N 0.000 description 5
229960002212 hexobendine Drugs 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
IFFPICMESYHZPQ-UHFFFAOYSA-N Prenylamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCNC(C)CC1=CC=CC=C1 IFFPICMESYHZPQ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
230000002107 myocardial effect Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
229960001989 prenylamine Drugs 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KBRAFCMQLHSOQL-UHFFFAOYSA-N 5,7-dimethyl-1,4-diazepane Chemical compound CC1CC(C)NCCN1 KBRAFCMQLHSOQL-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
206010002091 Anaesthesia Diseases 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000007514 bases Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000013065 commercial product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
238000010992 reflux Methods 0.000 description 2
150000003512 tertiary amines Chemical class 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
238000005406 washing Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
COWPTMLRSANSMQ-OLQVQODUSA-N (2r,3s)-2,3-dimethylpiperazine Chemical compound C[C@H]1NCCN[C@H]1C COWPTMLRSANSMQ-OLQVQODUSA-N 0.000 description 1
NSMWYRLQHIXVAP-OLQVQODUSA-N (2r,5s)-2,5-dimethylpiperazine Chemical compound C[C@H]1CN[C@H](C)CN1 NSMWYRLQHIXVAP-OLQVQODUSA-N 0.000 description 1
NSMWYRLQHIXVAP-WDSKDSINSA-N (2s,5s)-2,5-dimethylpiperazine Chemical compound C[C@H]1CN[C@@H](C)CN1 NSMWYRLQHIXVAP-WDSKDSINSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
AILFRWRYZZVJTL-UHFFFAOYSA-N 1-methylpiperazin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.CN1CCNCC1 AILFRWRYZZVJTL-UHFFFAOYSA-N 0.000 description 1
GOTVEDVYURXGPS-UHFFFAOYSA-N 2,5-dimethylpiperazine;dihydrochloride Chemical compound Cl.Cl.CC1CNC(C)CN1 GOTVEDVYURXGPS-UHFFFAOYSA-N 0.000 description 1
YKJDSXDRDCDOHB-UHFFFAOYSA-N 2-chloroethyl 3,4,5-trimethoxybenzoate Chemical compound COC1=CC(C(=O)OCCCl)=CC(OC)=C1OC YKJDSXDRDCDOHB-UHFFFAOYSA-N 0.000 description 1
DXOHZOPKNFZZAD-UHFFFAOYSA-N 2-ethylpiperazine Chemical compound CCC1CNCCN1 DXOHZOPKNFZZAD-UHFFFAOYSA-N 0.000 description 1
VCKAKBROIJTVJI-UHFFFAOYSA-N 2-ethylpiperazine;dihydrochloride Chemical compound Cl.Cl.CCC1CNCCN1 VCKAKBROIJTVJI-UHFFFAOYSA-N 0.000 description 1
WLHZTLVYOKJNLF-UHFFFAOYSA-N 3-bromopropyl 3,4,5-trimethoxybenzoate Chemical compound COC1=CC(C(=O)OCCCBr)=CC(OC)=C1OC WLHZTLVYOKJNLF-UHFFFAOYSA-N 0.000 description 1
LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical class NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 1
229950009941 chloralose Drugs 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000003218 coronary vasodilator agent Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
229940072033 potash Drugs 0.000 description 1
238000011158 quantitative evaluation Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings

Landscapes

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

CH1725968A 1967-12-06 1968-11-19 Verfahren zur Herstellung von am Kohlenstoff des Heterocyclus alkylierten N,N'-disubstituierten Diazacycloalkanen CH509327A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1670011		1967-12-06

Publications (1)

Publication Number	Publication Date
CH509327A true CH509327A (de)	1971-06-30

Family

ID=5686274

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1725968A CH509327A (de)	1967-12-06	1968-11-19	Verfahren zur Herstellung von am Kohlenstoff des Heterocyclus alkylierten N,N'-disubstituierten Diazacycloalkanen

Country Status (12)

Country	Link
AT (1)	AT284130B (cs)
BR (1)	BR6804642D0 (cs)
CH (1)	CH509327A (cs)
CS (1)	CS159237B2 (cs)
DK (1)	DK122609B (cs)
FI (1)	FI49717C (cs)
FR (1)	FR8139M (cs)
GB (1)	GB1184408A (cs)
IL (1)	IL31079A (cs)
RO (1)	RO55756A (cs)
SE (1)	SE345854B (cs)
YU (1)	YU32624B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS632986A (ja) *	1986-06-23	1988-01-07	Kanebo Ltd	新規なピペラジン誘導体および該化合物を有効成分とする抗潰瘍薬

1968
- 1968-11-14 AT AT1108168A patent/AT284130B/de not_active IP Right Cessation
- 1968-11-17 IL IL31079A patent/IL31079A/en unknown
- 1968-11-19 CH CH1725968A patent/CH509327A/de not_active IP Right Cessation
- 1968-11-21 GB GB55228/68A patent/GB1184408A/en not_active Expired
- 1968-12-03 CS CS824668A patent/CS159237B2/cs unknown
- 1968-12-03 YU YU2841/68A patent/YU32624B/xx unknown
- 1968-12-05 BR BR204642/68A patent/BR6804642D0/pt unknown
- 1968-12-05 SE SE16636/68A patent/SE345854B/xx unknown
- 1968-12-05 FI FI683498A patent/FI49717C/fi active
- 1968-12-05 DK DK594168AA patent/DK122609B/da not_active IP Right Cessation
- 1968-12-06 RO RO58416A patent/RO55756A/ro unknown
1969
- 1969-02-25 FR FR176771A patent/FR8139M/fr not_active Expired

Also Published As

Publication number	Publication date
SE345854B (cs)	1972-06-12
YU32624B (en)	1975-04-30
BR6804642D0 (pt)	1973-08-16
IL31079A0 (en)	1969-01-29
AT284130B (de)	1970-09-10
GB1184408A (en)	1970-03-18
FI49717B (cs)	1975-06-02
IL31079A (en)	1972-01-27
YU284168A (en)	1974-10-31
CS159237B2 (cs)	1974-12-27
RO55756A (cs)	1974-02-01
FR8139M (cs)	1970-08-10
FI49717C (fi)	1975-09-10
DK122609B (da)	1972-03-20

Legal Events

Date	Code	Title	Description
1989-01-31	PL	Patent ceased

Publication	Publication Date	Title
DE1695556C3 (de)	1981-06-25	3-Alkyl-1,2,3,4,4a,9-hexahydropyrazino[1,2-f]morphanthridinderivate
EP0726899B1 (de)	2000-01-19	Neue pyrazincarboxamidderivate, ihre herstellung und ihre verwendung in arzneimitteln
DE1670849C3 (de)	1978-07-20	Verfahren zur Herstellung von 8-Acylamino-1,23,4-tetrahydroisochinolinen
CH494766A (de)	1970-08-15	Verfahren zur Herstellung von Azaspiroalkandionen
EP0047923B1 (de)	1984-05-09	Isochinolinderivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
EP0005828B1 (de)	1981-03-11	Neue substituierte Phenylpiperazinderivate, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung
EP0000220A1 (de)	1979-01-10	Dihydrouracile, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE3309596A1 (de)	1984-04-05	2-substituierte 1-(3'-aminoalkyl)-1,2,3,4-tetrahydro-ss-carboline, ihre herstellung und verwendung als arzneimittel
EP0005232A1 (de)	1979-11-14	Isochinolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
EP0105210B1 (de)	1987-03-04	Isochinolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
DE2434951A1 (de)	1975-02-13	3-substituierte diphenylhydantoine
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