DE2004201A1 - Neue 2,6-Bis(dialkanolamino)-pyrimido-[5,4-d]pyrimidine und Verfahren zu ihrer Herstellung - Google Patents
Neue 2,6-Bis(dialkanolamino)-pyrimido-[5,4-d]pyrimidine und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2004201A1 DE2004201A1 DE19702004201 DE2004201A DE2004201A1 DE 2004201 A1 DE2004201 A1 DE 2004201A1 DE 19702004201 DE19702004201 DE 19702004201 DE 2004201 A DE2004201 A DE 2004201A DE 2004201 A1 DE2004201 A1 DE 2004201A1
- Authority
- DE
- Germany
- Prior art keywords
- radicals
- piperidino
- pyrimido
- dialkanolamino
- diethanolamino
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 10
- 150000003230 pyrimidines Chemical class 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 25
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000011630 iodine Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 238000001640 fractional crystallisation Methods 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000011347 resin Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229920001592 potato starch Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 235000010199 sorbic acid Nutrition 0.000 description 2
- 239000004334 sorbic acid Substances 0.000 description 2
- 229940075582 sorbic acid Drugs 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 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
- XWNSFEAWWGGSKJ-UHFFFAOYSA-N 4-acetyl-4-methylheptanedinitrile Chemical compound N#CCCC(C)(C(=O)C)CCC#N XWNSFEAWWGGSKJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000004153 Potassium bromate Substances 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- VJLOFJZWUDZJBX-UHFFFAOYSA-N bis(2-hydroxyethyl)azanium;chloride Chemical compound [Cl-].OCC[NH2+]CCO VJLOFJZWUDZJBX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702004201 DE2004201A1 (de) | 1970-01-30 | 1970-01-30 | Neue 2,6-Bis(dialkanolamino)-pyrimido-[5,4-d]pyrimidine und Verfahren zu ihrer Herstellung |
| RO65570A RO57779A7 (enrdf_load_stackoverflow) | 1970-01-30 | 1971-01-12 | |
| RO68283A RO58069A7 (enrdf_load_stackoverflow) | 1970-01-30 | 1971-01-12 | |
| ES387409A ES387409A1 (es) | 1970-01-30 | 1971-01-19 | Procedimiento para la preparacion de nuevas 2,6-bis (dial- canolamino) - pirimido (5,4-d) pirimidinas. |
| SU1613262A SU379093A1 (ru) | 1971-01-25 | СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ 2,6-бис- (ДИАЛКАНОЛАМИНО)-ПИРИМИДО | |
| AU24767/71A AU2476771A (en) | 1970-01-30 | 1971-01-28 | Chemical compounds |
| BG016681A BG18612A3 (bg) | 1970-01-30 | 1971-01-28 | Метод за получаване на нови 2,6-бис(диалканоламино)-пиримидо (5,4-g)пиримидини |
| NL7101118A NL7101118A (enrdf_load_stackoverflow) | 1970-01-30 | 1971-01-28 | |
| BE762327A BE762327A (fr) | 1970-01-30 | 1971-01-29 | Nouvelles 2,6-bis(dialcanolamino)-pyrimido (5,4-d) pyrimidines et procedes pour les fabriquer |
| IL36097A IL36097A0 (en) | 1970-01-30 | 1971-01-29 | 2,6-bis (dialkanolamino)-pyrimido (5,4-d) pyrimidines,their preparation and pharmaceutical compositions containing them |
| ZA710579A ZA71579B (en) | 1970-01-30 | 1971-01-29 | Improvements relating to 2,6-bis(dialkanolamino)-pyrimido(5,4-d)pyrimidines |
| AT1020971A AT302336B (de) | 1970-01-30 | 1971-01-29 | Verfahren zur Herstellung von neuen 2,6-Bis(dialkanolamino)-pyrimido[5,4-d]pyrimidinen |
| AT76771A AT302313B (de) | 1970-01-30 | 1971-01-29 | Verfahren zur Herstellung vonn neuen 2,6-Bis(dialkanolamino)-pyrimido[5,4-d]pyrimidinen |
| HUTO840A HU163360B (enrdf_load_stackoverflow) | 1970-01-30 | 1971-01-29 | |
| FR7103038A FR2081471B1 (enrdf_load_stackoverflow) | 1970-01-30 | 1971-01-29 | |
| ES388479A ES388479A1 (es) | 1970-01-30 | 1971-02-20 | Procedimiento para la preparacion de nuevas 2,6-bis (dial- canol-amino) - pirimido (5,4-d) pirimidinas. |
| GB2066071A GB1313056A (en) | 1970-01-30 | 1971-04-19 | Pyrimidopyrimidines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702004201 DE2004201A1 (de) | 1970-01-30 | 1970-01-30 | Neue 2,6-Bis(dialkanolamino)-pyrimido-[5,4-d]pyrimidine und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2004201A1 true DE2004201A1 (de) | 1971-08-05 |
Family
ID=5760961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702004201 Pending DE2004201A1 (de) | 1970-01-30 | 1970-01-30 | Neue 2,6-Bis(dialkanolamino)-pyrimido-[5,4-d]pyrimidine und Verfahren zu ihrer Herstellung |
Country Status (13)
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1116676B (de) * | 1955-03-14 | 1961-11-09 | Thomae Gmbh Dr K | Verfahren zur Herstellung von Pyrimido [5, 4-d] pyrimidinen |
| GB1051218A (enrdf_load_stackoverflow) * | 1963-03-09 | |||
| SE351849B (enrdf_load_stackoverflow) * | 1968-07-31 | 1972-12-11 | Thomae Gmbh Dr K |
-
1970
- 1970-01-30 DE DE19702004201 patent/DE2004201A1/de active Pending
-
1971
- 1971-01-12 RO RO65570A patent/RO57779A7/ro unknown
- 1971-01-12 RO RO68283A patent/RO58069A7/ro unknown
- 1971-01-19 ES ES387409A patent/ES387409A1/es not_active Expired
- 1971-01-28 NL NL7101118A patent/NL7101118A/xx unknown
- 1971-01-28 BG BG016681A patent/BG18612A3/xx unknown
- 1971-01-28 AU AU24767/71A patent/AU2476771A/en not_active Expired
- 1971-01-29 AT AT1020971A patent/AT302336B/de not_active IP Right Cessation
- 1971-01-29 FR FR7103038A patent/FR2081471B1/fr not_active Expired
- 1971-01-29 IL IL36097A patent/IL36097A0/xx unknown
- 1971-01-29 HU HUTO840A patent/HU163360B/hu unknown
- 1971-01-29 ZA ZA710579A patent/ZA71579B/xx unknown
- 1971-01-29 BE BE762327A patent/BE762327A/xx unknown
- 1971-01-29 AT AT76771A patent/AT302313B/de not_active IP Right Cessation
- 1971-02-20 ES ES388479A patent/ES388479A1/es not_active Expired
- 1971-04-19 GB GB2066071A patent/GB1313056A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE762327A (fr) | 1971-07-29 |
| ES388479A1 (es) | 1973-05-01 |
| BG18612A3 (bg) | 1975-02-25 |
| AU2476771A (en) | 1972-08-03 |
| SU379093A3 (enrdf_load_stackoverflow) | 1973-04-18 |
| RO57779A7 (enrdf_load_stackoverflow) | 1975-03-15 |
| FR2081471B1 (enrdf_load_stackoverflow) | 1974-09-06 |
| ZA71579B (en) | 1971-11-24 |
| ES387409A1 (es) | 1973-05-16 |
| AT302313B (de) | 1972-10-10 |
| RO58069A7 (enrdf_load_stackoverflow) | 1975-06-15 |
| GB1313056A (en) | 1973-04-11 |
| FR2081471A1 (enrdf_load_stackoverflow) | 1971-12-03 |
| AT302336B (de) | 1972-10-10 |
| IL36097A0 (en) | 1971-03-24 |
| NL7101118A (enrdf_load_stackoverflow) | 1971-08-03 |
| HU163360B (enrdf_load_stackoverflow) | 1973-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2901477C2 (de) | Spirothienohydantoinderivate und diese enthaltende Arzneimittel | |
| EP0063381A1 (de) | Neue Pyrazolo(3,4-d)pyrimidine, Verfahren zu deren Herstellung und sie enthaltende Arzneimittel | |
| DE2710997B2 (de) | 4-Alkoxycarbonylamino-phenyläthanolamine, deren Herstellung und deren Verwendung als Arzneimittel | |
| EP0053767B1 (de) | Tricyclische Cytosinderivate zur Verwendung in Arzneimitteln und Verfahren zu ihrer Herstellung | |
| DE2628189A1 (de) | 3-phenylindoline, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2523103A1 (de) | Neue propargyl-2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben | |
| DE3105285A1 (de) | 2-amino-3-(hydroxy(phenyl)methyl)-phenylessigsaeure und ihre derivate, verfahren zur herstellung dieser verbindungen und therapeutische zubereitungen, welche diese verbindungen enthalten | |
| DE2434693A1 (de) | 1,4-disubstituierte piperidine | |
| DE2845406A1 (de) | 1-arylalkylimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende formulierungen | |
| EP0088250B1 (de) | Neue basisch substituierte 4-Phenyl-4,5,6,7-tetrahydrothieno-(2,3-c)pyridine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2004201A1 (de) | Neue 2,6-Bis(dialkanolamino)-pyrimido-[5,4-d]pyrimidine und Verfahren zu ihrer Herstellung | |
| EP0129153B1 (de) | Neue 1-Acetonyl-2-(phenylimino)-imidazolidine, deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung | |
| DE2246728A1 (de) | Neue substituierte aethylendiamine, verfahren zu ihrer herstellung und solche diamine enthaltende arzneipraeparate | |
| DE68902627T2 (de) | Verwendung von chromanderivaten zur herstellung eines medikamentes zur behandlung von depressiven zustaenden. | |
| DE69824713T2 (de) | Verwendung von halo und/oder nitro-substituierten flavonoiden als angstlöser | |
| DE2004202A1 (de) | Neue 2,6-Dimorpholino-8-alkanolamino-pyrimido[5,4-d]pyrimidine | |
| DE2051961A1 (de) | 6 substituierte Indol eckige Klammer auf 1,2 c eckige Klammer zu chinazoline und Verfahren zu deren Herstellung | |
| DE2004200A1 (de) | Neue basisch trisubstituierte Pyrimido-[5,4] pyrimidine und Verfahren zu ihrer Herstellung | |
| DE1795032A1 (de) | 2,6-Dimorpholino-8-diaethanolamino-pyrimido[5,4-d]pyrimidin | |
| DE69118129T2 (de) | 1,2,3,6-Tetrahydronpyridinderivate | |
| DE1933426A1 (de) | 2,6-Dimorpholino-8-alkanolamino-pyrimido-[5,4-d]pyrimidine | |
| DE3241333C2 (enrdf_load_stackoverflow) | ||
| DE3431195A1 (de) | Neue benzodiazepine, verfahren zu ihrer herstellung sowie ihre verwendung | |
| EP0180889B1 (de) | 3-Amino-2,3-dihydro-1-benzoxepin-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1795030A1 (de) | Neue 2,6-Bis-(diaethanolamino)-pyrimido-[5,4-d]-pyrimidine |