DE2214474A1 - In 1-Stellung benzylsubstituierte Tetrahydro-2(lH>pyrimidone und Verfahren zu ihrer Herstellung - Google Patents
In 1-Stellung benzylsubstituierte Tetrahydro-2(lH>pyrimidone und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2214474A1 DE2214474A1 DE19722214474 DE2214474A DE2214474A1 DE 2214474 A1 DE2214474 A1 DE 2214474A1 DE 19722214474 DE19722214474 DE 19722214474 DE 2214474 A DE2214474 A DE 2214474A DE 2214474 A1 DE2214474 A1 DE 2214474A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- group
- mol
- yield
- methanol
- 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
- 238000002360 preparation method Methods 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 150000008318 pyrimidones Chemical class 0.000 title 1
- -1 carbomethoxy Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical class [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 3
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- IAJINJSFYTZPEJ-UHFFFAOYSA-N 1h-pyrimidin-3-ium-2-one;chloride Chemical compound Cl.O=C1N=CC=CN1 IAJINJSFYTZPEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 5
- 239000002026 chloroform extract Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 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
- 241000699670 Mus sp. Species 0.000 description 3
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229960005152 pentetrazol Drugs 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ZVHWQQPJHLSYKL-UHFFFAOYSA-N 1-(chloromethyl)-4-octylbenzene Chemical compound CCCCCCCCC1=CC=C(CCl)C=C1 ZVHWQQPJHLSYKL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 2
- 230000002920 convulsive effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
- DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
- XAKRTOIHMJCULO-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]-1,3-diazinan-2-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)NCCC1 XAKRTOIHMJCULO-UHFFFAOYSA-N 0.000 description 1
- VORNGBNHDONIJP-UHFFFAOYSA-N 4-(chloromethyl)-n,n-dimethylaniline;hydrochloride Chemical compound Cl.CN(C)C1=CC=C(CCl)C=C1 VORNGBNHDONIJP-UHFFFAOYSA-N 0.000 description 1
- ZQLDNJKHLQOJGE-UHFFFAOYSA-N 4-octylbenzoic acid Chemical compound CCCCCCCCC1=CC=C(C(O)=O)C=C1 ZQLDNJKHLQOJGE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 241001417527 Pempheridae Species 0.000 description 1
- ZDVDCDLBOLSVGM-UHFFFAOYSA-N [chloro(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)C1=CC=CC=C1 ZDVDCDLBOLSVGM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000000160 carbon, hydrogen and nitrogen elemental analysis Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12814371A | 1971-03-25 | 1971-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2214474A1 true DE2214474A1 (de) | 1972-10-05 |
Family
ID=22433854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722214474 Pending DE2214474A1 (de) | 1971-03-25 | 1972-03-24 | In 1-Stellung benzylsubstituierte Tetrahydro-2(lH>pyrimidone und Verfahren zu ihrer Herstellung |
Country Status (15)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19962923A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Benzoylcyclohexandione |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE562987A (enrdf_load_stackoverflow) * | 1956-12-05 | |||
| US3681349A (en) * | 1970-03-05 | 1972-08-01 | Morton Norwich Products Inc | 1-(substituted benzyl) tetrahydro-2-(1h) pyrimidones |
-
1972
- 1972-03-16 IL IL39003A patent/IL39003A/xx unknown
- 1972-03-17 ZA ZA721832A patent/ZA721832B/xx unknown
- 1972-03-20 AR AR241030A patent/AR196986A1/es active
- 1972-03-20 ES ES400964A patent/ES400964A1/es not_active Expired
- 1972-03-21 GB GB1324872A patent/GB1327552A/en not_active Expired
- 1972-03-21 AU AU40226/72A patent/AU458346B2/en not_active Expired
- 1972-03-22 DK DK133972AA patent/DK129523B/da unknown
- 1972-03-23 AT AT254172A patent/AT315184B/de active
- 1972-03-23 CH CH434772A patent/CH568299A5/xx not_active IP Right Cessation
- 1972-03-23 NL NL7203883A patent/NL7203883A/xx unknown
- 1972-03-23 BE BE781158A patent/BE781158A/xx unknown
- 1972-03-24 DE DE19722214474 patent/DE2214474A1/de active Pending
- 1972-03-24 CA CA138,099A patent/CA965416A/en not_active Expired
- 1972-03-24 FR FR7210486A patent/FR2130686B1/fr not_active Expired
-
1974
- 1974-04-22 PH PH15764*UA patent/PH9703A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4022672A (en) | 1973-09-27 |
| CH568299A5 (enrdf_load_stackoverflow) | 1975-10-31 |
| AT315184B (de) | 1974-05-10 |
| ZA721832B (en) | 1973-10-31 |
| NL7203883A (enrdf_load_stackoverflow) | 1972-09-27 |
| DK129523B (da) | 1974-10-21 |
| FR2130686B1 (enrdf_load_stackoverflow) | 1975-06-20 |
| IL39003A (en) | 1975-02-10 |
| BE781158A (fr) | 1972-09-25 |
| GB1327552A (en) | 1973-08-22 |
| AR196986A1 (es) | 1974-03-08 |
| DK129523C (enrdf_load_stackoverflow) | 1975-03-24 |
| CA965416A (en) | 1975-04-01 |
| AU458346B2 (en) | 1975-02-07 |
| ES400964A1 (es) | 1975-09-01 |
| FR2130686A1 (enrdf_load_stackoverflow) | 1972-11-03 |
| PH9703A (en) | 1976-02-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2660606C2 (de) | Verfahren zur Herstellung von Phenylacrylsäureestern, Phenyloxaloacetat-Enolatsalze | |
| DE1545551A1 (de) | Neue Chinazolinonderivate und ihre Herstellung | |
| EP0068261B1 (de) | N-Oxacyclyl-Alkylpiperidin-Derivate, Verfahren zu ihrer Herstellung, sie enthaltende pharmazeutische Präparate und deren Verwendung | |
| DD148055A5 (de) | Verfahren zur herstellung von o-substituierten derivaten des(+)-cyanidan-3-ols | |
| DE3105330A1 (de) | "4-amino-6,7-dimethoxy-2-piperazinylchinazolin-derivate, ihre herstellung und ihre verwendung" | |
| DD140040A5 (de) | Verfahren zur herstellung von 5-alkylthio-pyrimidinen | |
| DD150602A5 (de) | Verfahren zur herstellung 6-substituierter 11-alkylen-morphantridine | |
| EP0000074B1 (de) | Neue Bispidinderivate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten | |
| DE3011809A1 (de) | Pyrimidyl-chinazoline, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische praeparate und ihre verwendung | |
| DE2214474A1 (de) | In 1-Stellung benzylsubstituierte Tetrahydro-2(lH>pyrimidone und Verfahren zu ihrer Herstellung | |
| DE2313506A1 (de) | Oktansaeure-derivate | |
| DE2725992A1 (de) | Benzylcyanoacetale, verfahren zu ihrer herstellung und ihre verwendung | |
| DE1468466A1 (de) | Verfahren zur Herstellung substituierter cyclischer Carboxamidoverbindungen | |
| DE2218221C3 (de) | Verfahren zur Herstellung von 2,4-Diamino-5-(3,43-trimethoxybenzyO-pyrimidin | |
| EP0552758A1 (de) | N-5-geschützte 2,5-Diamino-4,6-dichlorpyrimidine und Verfahren zu deren Herstellung | |
| DE1695554C3 (de) | Verfahren zur Herstellung kondensierter Piperazinonderivate | |
| DE671787C (de) | Verfahren zur Darstellung von Pyrimidinverbindungen | |
| EP0152598A1 (de) | Cyanomethyl-(2-cyano-ethyl)-(3-hydroxy-propyl)-amin, seine Verwendung zur Herstellung von 1-(3-Hydroxy-propyl)-1,4-diazepan und 1,4 Bis-[3-(3,4,5-trimethoxy-benzoyloxy)-propyl]-diazepan | |
| DE2020762A1 (de) | Azainden-3-niedrigaliphatische-Saeuren und Verfahren zu deren Herstellung | |
| DE2025819A1 (de) | alpha-Aminopenicillinverbindungen und Verfahren zu ihrer Herstellung | |
| AT363950B (de) | Verfahren zur herstellung von 2,4-diamino-5-benzylpyrimidinen | |
| AT258915B (de) | Verfahren zur Herstellung von neuen 4-Amino-7-alkylamino-6-pteridin-N-alkyl-carboxamiden | |
| AT249672B (de) | Verfahren zur Herstellung von neuen Imidazolderivaten | |
| AT263790B (de) | Verfahren zur Herstellung von neuen 2,3,4,5-Tetrahydro-1,4-benzoxazepinen, von deren Salzen und optisch isomeren Formen | |
| AT258919B (de) | Verfahren zur Herstellung neuer 2-Methyl-3-phenyl-3H-4-chinazolone |