DE1805948A1 - Neue heterocyclische Verbindungen und Verfahren zu deren Herstellung - Google Patents
Neue heterocyclische Verbindungen und Verfahren zu deren HerstellungInfo
- Publication number
- DE1805948A1 DE1805948A1 DE19681805948 DE1805948A DE1805948A1 DE 1805948 A1 DE1805948 A1 DE 1805948A1 DE 19681805948 DE19681805948 DE 19681805948 DE 1805948 A DE1805948 A DE 1805948A DE 1805948 A1 DE1805948 A1 DE 1805948A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrimidine
- thiazolo
- optionally
- free base
- hydroxy
- 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 44
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 59
- 239000002253 acid Substances 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 47
- 239000012458 free base Substances 0.000 claims description 45
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 22
- NVHNGVXBCWYLFA-UHFFFAOYSA-N 1,3-diazinane-2-thione Chemical compound S=C1NCCCN1 NVHNGVXBCWYLFA-UHFFFAOYSA-N 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- LVCJAONJIWANJQ-UHFFFAOYSA-N 3-(2-phenylphenyl)-2,5,6,7-tetrahydro-[1,3]thiazolo[3,2-a]pyrimidin-3-ol Chemical compound C1(=C(C=CC=C1)C1(CSC=2N1CCCN2)O)C2=CC=CC=C2 LVCJAONJIWANJQ-UHFFFAOYSA-N 0.000 claims description 3
- YUBLSCRPHWJZPZ-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1(CSC=2N1CCCN2)O Chemical compound ClC1=CC=C(C=C1)C1(CSC=2N1CCCN2)O YUBLSCRPHWJZPZ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 claims description 2
- ZJFWCELATJMDNO-UHFFFAOYSA-N 2-bromo-1-(4-fluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CBr)C=C1 ZJFWCELATJMDNO-UHFFFAOYSA-N 0.000 claims description 2
- KGHGZRVXCKCJGX-UHFFFAOYSA-N 2-bromo-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CBr)=CC=C1C1=CC=CC=C1 KGHGZRVXCKCJGX-UHFFFAOYSA-N 0.000 claims description 2
- TZIYNLSEBAYCBZ-UHFFFAOYSA-N 2-bromo-1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)CBr)=C1 TZIYNLSEBAYCBZ-UHFFFAOYSA-N 0.000 claims description 2
- RXDYOLRABMJTEF-UHFFFAOYSA-N 2-chloro-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Cl)C(=O)C1=CC=CC=C1 RXDYOLRABMJTEF-UHFFFAOYSA-N 0.000 claims description 2
- QWCBMLYPXNRUCT-UHFFFAOYSA-N 3-(2-phenylphenyl)-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound C1(=C(C=CC=C1)C1=CSC=2N1CCCN=2)C1=CC=CC=C1 QWCBMLYPXNRUCT-UHFFFAOYSA-N 0.000 claims description 2
- HHDXPWXFJVUVLL-UHFFFAOYSA-N 3-phenyl-2,5,6,7-tetrahydro-[1,3]thiazolo[3,2-a]pyrimidin-3-ol Chemical compound C1SC2=NCCCN2C1(O)C1=CC=CC=C1 HHDXPWXFJVUVLL-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 3
- CXWMCLXWVWQPMJ-UHFFFAOYSA-N 2,3-diphenyl-2,5,6,7-tetrahydro-[1,3]thiazolo[3,2-a]pyrimidin-3-ol Chemical compound C1(=CC=CC=C1)C1C(N2C(=NCCC2)S1)(O)C1=CC=CC=C1 CXWMCLXWVWQPMJ-UHFFFAOYSA-N 0.000 claims 2
- CDUYCVWBLGEWSY-UHFFFAOYSA-N 5h-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound C1C=CN=C2SC=CN12 CDUYCVWBLGEWSY-UHFFFAOYSA-N 0.000 claims 2
- XQJAHBHCLXUGEP-UHFFFAOYSA-N 2-bromo-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CBr)C=C1 XQJAHBHCLXUGEP-UHFFFAOYSA-N 0.000 claims 1
- UZXKWLDYUXFLFO-UHFFFAOYSA-N 3,5,6,7-tetrahydro-2h-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound C1CCN=C2SCCN21 UZXKWLDYUXFLFO-UHFFFAOYSA-N 0.000 claims 1
- IZZLXHIJSOOTDI-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2,5,6,7-tetrahydro-[1,3]thiazolo[3,2-a]pyrimidin-3-ol Chemical compound ClC=1C=C(C=CC=1Cl)C1(CSC=2N1CCCN=2)O IZZLXHIJSOOTDI-UHFFFAOYSA-N 0.000 claims 1
- QHYFWZXUCDNLIZ-UHFFFAOYSA-N 3-(4-methoxyphenyl)-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound COC1=CC=C(C=C1)C1=CSC=2N1CCCN2 QHYFWZXUCDNLIZ-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000001914 filtration Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PAKFHEFMTRCFAU-UHFFFAOYSA-N 2-bromo-1-(3,4-dichlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1Cl PAKFHEFMTRCFAU-UHFFFAOYSA-N 0.000 description 1
- MCRINSAETDOKDE-UHFFFAOYSA-N 2-chloro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CCl)C=C1 MCRINSAETDOKDE-UHFFFAOYSA-N 0.000 description 1
- BDDBSZJFQNJLTH-UHFFFAOYSA-N 3-(4-chlorophenyl)-6,7-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine hydrochloride Chemical compound Cl.ClC1=CC=C(C=C1)C1=CSC=2N1CCCN2 BDDBSZJFQNJLTH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- -1 3-p-fluorophenyl-6,7-dihydro-5H-thiazolo [3,2-a] pyrimidine hydrochloride Chemical compound 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- 244000089409 Erythrina poeppigiana Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 235000009776 Rathbunia alamosensis Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- IDXKTTNFXPPXJY-UHFFFAOYSA-N pyrimidin-1-ium;chloride Chemical compound Cl.C1=CN=CN=C1 IDXKTTNFXPPXJY-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68030767A | 1967-11-03 | 1967-11-03 | |
| US74185668A | 1968-07-02 | 1968-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1805948A1 true DE1805948A1 (de) | 1969-06-26 |
Family
ID=27102429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681805948 Pending DE1805948A1 (de) | 1967-11-03 | 1968-10-30 | Neue heterocyclische Verbindungen und Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE723289A (enrdf_load_stackoverflow) |
| CH (2) | CH498139A (enrdf_load_stackoverflow) |
| DE (1) | DE1805948A1 (enrdf_load_stackoverflow) |
| ES (1) | ES359831A1 (enrdf_load_stackoverflow) |
| FR (2) | FR1595659A (enrdf_load_stackoverflow) |
| GB (1) | GB1220896A (enrdf_load_stackoverflow) |
| SE (1) | SE352088B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2195426B1 (enrdf_load_stackoverflow) * | 1972-08-09 | 1975-10-17 | Lipha |
-
1968
- 1968-10-02 CH CH1475268A patent/CH498139A/de not_active IP Right Cessation
- 1968-10-02 CH CH1079670A patent/CH498140A/de not_active IP Right Cessation
- 1968-10-04 GB GB4716068A patent/GB1220896A/en not_active Expired
- 1968-10-14 SE SE1381868A patent/SE352088B/xx unknown
- 1968-10-30 DE DE19681805948 patent/DE1805948A1/de active Pending
- 1968-10-31 FR FR1595659D patent/FR1595659A/fr not_active Expired
- 1968-10-31 BE BE723289D patent/BE723289A/xx unknown
- 1968-11-02 ES ES359831A patent/ES359831A1/es not_active Expired
-
1969
- 1969-01-28 FR FR183235A patent/FR8194M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE723289A (enrdf_load_stackoverflow) | 1969-04-30 |
| CH498139A (de) | 1970-10-31 |
| ES359831A1 (es) | 1970-10-01 |
| SE352088B (enrdf_load_stackoverflow) | 1972-12-18 |
| GB1220896A (en) | 1971-01-27 |
| FR1595659A (enrdf_load_stackoverflow) | 1970-06-15 |
| FR8194M (enrdf_load_stackoverflow) | 1970-09-07 |
| CH498140A (de) | 1970-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1956384B2 (de) | 1 -Isopropyl-4 phenyl-2-( 1 H)-chinazolinonderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| DE1695133A1 (de) | Verfahren zur Herstellung von Imidazolderivaten | |
| DE1695189A1 (de) | Verfahren zur Herstellung von Imidazolderivaten | |
| DE2534962C3 (de) | cis-3,4-Ureylenthiophan-l,l-dioxid und Verfahren zu seiner Herstellung | |
| DE2242454A1 (de) | 1-aethyl-imidazole, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE1805948A1 (de) | Neue heterocyclische Verbindungen und Verfahren zu deren Herstellung | |
| AT394558B (de) | Verfahren zur herstellung neuer 6-phenaethylaminoalkyl-7-hydroxy-furo-(3,4-c)pyridinderivate | |
| DE2424572A1 (de) | Triazolo-isochinolin-derivate enthaltende pharmazeutika | |
| DE3438244C2 (enrdf_load_stackoverflow) | ||
| DE2841644A1 (de) | 3(tetrazol-5-yl)-1-azaxanthone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE1620654C3 (de) | 1,2-Dihydro-1 -hydroxy-2-imino-4piperidino-pyrimidine sowie Verfahren zu deren Herstellung | |
| DE2321786C2 (de) | S↑IV↑ -Benzo-1,2,4-thiadiazine | |
| EP0012725B1 (de) | Chinoxalin-Di-N-oxid-Derivate, Verfahren zu ihrer Herstellung, Mittel diese enthaltend und ihre Verwendung | |
| AT281818B (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| DE2650231A1 (de) | Neue imidazolverbindungen, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE2114563A1 (de) | Substituierte 6 Phenyl imidazo eckige Klammer auf 2,1 b eckige Klammer zu thiazole | |
| DE1770030A1 (de) | 5-Hydroxy-5-phenyl-2,3-dihydro-5H-imidazo[2,1-a]-isoindole und Verfahren zu ihrer Herstellung | |
| DE1955682C3 (de) | 2- [(MethylsulfinylVacetyl] -pyridin und Verfahren zu seiner Herstellung | |
| DE2147103A1 (de) | Neue Imidazo eckige Klammer auf 4,5 b eckige Klammer zu pyridinderivate, ihre Herstellung und die Zusammensetzun gen, die sie enthalten | |
| AT236389B (de) | Verfahren zur Herstellung von neuen N-substituierten heterocyclischen Verbindungen | |
| DE2005296A1 (de) | Verfahren zur Herstellung von 2-eckige Klammer auf (Methylsulfinyl)-acetyl eckige Klammer zu pyridin | |
| DE1962149A1 (de) | Organische Verbindungen und Verfahren zu ihrer Herstellung | |
| AT394046B (de) | Neue thieno(3',4'-4,5)imidazo(2,1-b)thiazolderivate, verfahren zu ihrer herstellung und ihre verwendung | |
| AT346342B (de) | Verfahren zur herstellung von neuen 2- piperazinyl-thiazol-derivaten und ihren salzen | |
| AT304540B (de) | Verfahren zur Herstellung neuer 2-n-Alkyl-3-hydroxy-3-phenyl-2,3,6,7-tetrahydro-5H-thiazolo[3,2-a]pyrimidine bzw. 2-n-Alkyl-3-hydroxy-3-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole und ihrer Salze |