CH539047A - Verfahren zur Herstellung von 1-Alkyl-4,6-diphenylpyrimidin-2(1H)-onen - Google Patents
Verfahren zur Herstellung von 1-Alkyl-4,6-diphenylpyrimidin-2(1H)-onenInfo
- Publication number
- CH539047A CH539047A CH1646670A CH1646670A CH539047A CH 539047 A CH539047 A CH 539047A CH 1646670 A CH1646670 A CH 1646670A CH 1646670 A CH1646670 A CH 1646670A CH 539047 A CH539047 A CH 539047A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl
- formula
- phenyl
- ethyl
- alkoxy
- Prior art date
Links
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical class C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 235000013877 carbamide Nutrition 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000000411 inducer Substances 0.000 abstract 1
- 230000004799 sedative–hypnotic effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- FJCQSNRTMHICQQ-UHFFFAOYSA-N 1-ethyl-4,6-diphenylpyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 FJCQSNRTMHICQQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- -1 (m-bromophenyl) -pyrimidin-2 (1H) - -one Chemical compound 0.000 description 2
- UCEHZDJROOEPOW-UHFFFAOYSA-N 4,6-bis(3-chlorophenyl)-1-methylpyrimidin-2-one Chemical compound N=1C(=O)N(C)C(C=2C=C(Cl)C=CC=2)=CC=1C1=CC=CC(Cl)=C1 UCEHZDJROOEPOW-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000000147 hypnotic effect Effects 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MGMNGNDIJHTGOF-UHFFFAOYSA-N 1,3-bis(3-chlorophenyl)propane-1,3-dione Chemical compound ClC1=CC=CC(C(=O)CC(=O)C=2C=C(Cl)C=CC=2)=C1 MGMNGNDIJHTGOF-UHFFFAOYSA-N 0.000 description 1
- WQUXFYFIXPSYGK-UHFFFAOYSA-N 1-butyl-4,6-diphenylpyrimidin-2-one Chemical compound N=1C(=O)N(CCCC)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 WQUXFYFIXPSYGK-UHFFFAOYSA-N 0.000 description 1
- JAMITZDZMVAWEO-UHFFFAOYSA-N 1-ethyl-4-(3-methoxyphenyl)-6-(3-nitrophenyl)pyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=C(C=CC=2)[N+]([O-])=O)=CC=1C1=CC=CC(OC)=C1 JAMITZDZMVAWEO-UHFFFAOYSA-N 0.000 description 1
- ULZHFSLOIIOYAP-UHFFFAOYSA-N 1-ethyl-6-(3-methoxyphenyl)-4-(3-nitrophenyl)pyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=C(OC)C=CC=2)=CC=1C1=CC=CC([N+]([O-])=O)=C1 ULZHFSLOIIOYAP-UHFFFAOYSA-N 0.000 description 1
- UOZQLXATNWEWBI-UHFFFAOYSA-N 1-methyl-6-(3-nitrophenyl)-4-phenylpyrimidin-2-one Chemical compound N=1C(=O)N(C)C(C=2C=C(C=CC=2)[N+]([O-])=O)=CC=1C1=CC=CC=C1 UOZQLXATNWEWBI-UHFFFAOYSA-N 0.000 description 1
- JQVIRXYVNFLRTH-UHFFFAOYSA-N 4,6-diphenyl-1-propan-2-ylpyrimidin-2-one Chemical compound N=1C(=O)N(C(C)C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 JQVIRXYVNFLRTH-UHFFFAOYSA-N 0.000 description 1
- GJHYBWSQPJJAAT-UHFFFAOYSA-N 4,6-diphenyl-1-propylpyrimidin-2-one Chemical compound N=1C(=O)N(CCC)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 GJHYBWSQPJJAAT-UHFFFAOYSA-N 0.000 description 1
- XZWVLCGDOUREFE-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-1-ethyl-6-phenylpyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=CC=CC=2)=CC=1C1=CC=C(Cl)C(Cl)=C1 XZWVLCGDOUREFE-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VWPAFKMDEDXOEP-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-1-ethyl-4-phenylpyrimidin-2-one Chemical compound C(C)N1C(N=C(C=C1C1=C(C=CC=C1Cl)Cl)C1=CC=CC=C1)=O VWPAFKMDEDXOEP-UHFFFAOYSA-N 0.000 description 1
- FBPYZQHCDABJGD-UHFFFAOYSA-N 6-(3,4-dichlorophenyl)-1-methyl-4-phenylpyrimidin-2-one Chemical compound N=1C(=O)N(C)C(C=2C=C(Cl)C(Cl)=CC=2)=CC=1C1=CC=CC=C1 FBPYZQHCDABJGD-UHFFFAOYSA-N 0.000 description 1
- ABAJBWJLJWIQJI-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1-ethyl-4-phenylpyrimidin-2-one Chemical compound N=1C(=O)N(CC)C(C=2C=C(OC)C(OC)=CC=2)=CC=1C1=CC=CC=C1 ABAJBWJLJWIQJI-UHFFFAOYSA-N 0.000 description 1
- DSPQUJVQJJZLNA-UHFFFAOYSA-N 6-(3,4-dimethoxyphenyl)-1-methyl-4-phenylpyrimidin-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(C=2C=CC=CC=2)=NC(=O)N1C DSPQUJVQJJZLNA-UHFFFAOYSA-N 0.000 description 1
- VMZVSRLEMFTZTQ-UHFFFAOYSA-N 6-(3-chlorophenyl)-1-methyl-4-phenylpyrimidin-2-one Chemical compound CN1C(N=C(C=C1C1=CC(=CC=C1)Cl)C1=CC=CC=C1)=O VMZVSRLEMFTZTQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- GUHTYFMKNHVDTN-UHFFFAOYSA-N C(C)N1C(N=C(C=C1C1=CC=CC=C1)C1=CC(=CC=C1)C(F)(F)F)=O Chemical compound C(C)N1C(N=C(C=C1C1=CC=CC=C1)C1=CC(=CC=C1)C(F)(F)F)=O GUHTYFMKNHVDTN-UHFFFAOYSA-N 0.000 description 1
- GTPXHNRVDOPRME-UHFFFAOYSA-N CCN(C(C1=CC=CC=C1)=CC(C1=CC(C)=CC=C1)=N1)C1=O Chemical compound CCN(C(C1=CC=CC=C1)=CC(C1=CC(C)=CC=C1)=N1)C1=O GTPXHNRVDOPRME-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 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
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 239000008101 lactose 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
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003672 ureas Chemical class 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
- C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
-
- 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
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/516—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of nitrogen-containing compounds to >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/228—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing six-membered aromatic rings, e.g. phenylacetaldehyde
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
- C07C47/27—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
-
- 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- 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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US87857269A | 1969-11-20 | 1969-11-20 | |
| US3734170A | 1970-05-14 | 1970-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH539047A true CH539047A (de) | 1973-07-15 |
Family
ID=26714053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1646670A CH539047A (de) | 1969-11-20 | 1970-11-06 | Verfahren zur Herstellung von 1-Alkyl-4,6-diphenylpyrimidin-2(1H)-onen |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4911391B1 (da) |
| CH (1) | CH539047A (da) |
| DK (1) | DK126042B (da) |
| ES (1) | ES385691A1 (da) |
| IL (1) | IL35687A0 (da) |
-
1970
- 1970-11-06 CH CH1646670A patent/CH539047A/de not_active IP Right Cessation
- 1970-11-18 IL IL35687A patent/IL35687A0/xx unknown
- 1970-11-19 ES ES385691A patent/ES385691A1/es not_active Expired
- 1970-11-19 JP JP45101866A patent/JPS4911391B1/ja active Pending
- 1970-11-19 DK DK589070AA patent/DK126042B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4911391B1 (da) | 1974-03-16 |
| DK126042B (da) | 1973-06-04 |
| IL35687A0 (en) | 1971-01-28 |
| ES385691A1 (es) | 1973-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |