DE1139503B - Verfahren zur Herstellung neuer substituierter 2,6-Diketopiperazine. - Google Patents
Verfahren zur Herstellung neuer substituierter 2,6-Diketopiperazine.Info
- Publication number
- DE1139503B DE1139503B DE1960N0019200 DEN0019200A DE1139503B DE 1139503 B DE1139503 B DE 1139503B DE 1960N0019200 DE1960N0019200 DE 1960N0019200 DE N0019200 A DEN0019200 A DE N0019200A DE 1139503 B DE1139503 B DE 1139503B
- Authority
- DE
- Germany
- Prior art keywords
- acid
- mixture
- dimethoxyphenyl
- diketopiperazines
- methylethyl
- 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 11
- CYJAWBVQRMVFEO-UHFFFAOYSA-N piperazine-2,6-dione Chemical class O=C1CNCC(=O)N1 CYJAWBVQRMVFEO-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 11
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000011514 reflex Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 4- [2 '- (3 ", 4" -dimethoxyphenyl) -r-methylethyl] -2,6-diketopiperazine Chemical compound 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- MSQACBWWAIBWIC-UHFFFAOYSA-N hydron;piperazine;chloride Chemical compound Cl.C1CNCCN1 MSQACBWWAIBWIC-UHFFFAOYSA-N 0.000 description 2
- PRECVFCPUGFXKR-UHFFFAOYSA-N piperazine-2,6-dione;hydrochloride Chemical compound Cl.O=C1CNCC(=O)N1 PRECVFCPUGFXKR-UHFFFAOYSA-N 0.000 description 2
- UHLWHDLVXGMXGR-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)ethyl]piperazine-2,6-dione;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCN1CC(=O)NC(=O)C1 UHLWHDLVXGMXGR-UHFFFAOYSA-N 0.000 description 1
- LZSQXIOPVMMZNH-UHFFFAOYSA-N Cl.COC=1C=C(C=CC1OC)CC(C)N1CC(NC(C1)=O)=O Chemical compound Cl.COC=1C=C(C=CC1OC)CC(C)N1CC(NC(C1)=O)=O LZSQXIOPVMMZNH-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL245892 | 1959-11-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1139503B true DE1139503B (de) | 1962-11-15 |
Family
ID=19752057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1960N0019200 Pending DE1139503B (de) | 1959-11-28 | 1960-11-16 | Verfahren zur Herstellung neuer substituierter 2,6-Diketopiperazine. |
Country Status (6)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2520740A1 (fr) * | 1982-01-29 | 1983-08-05 | Sanofi Sa | Procede pour la preparation d'acyl-2-hexahydro-1,3,4,6,7,11b-2h-pyrazino (2,1-a) isoquinoleinones-4 et intermediaires |
-
1960
- 1960-11-16 DE DE1960N0019200 patent/DE1139503B/de active Pending
- 1960-11-16 GB GB39296/60A patent/GB912946A/en not_active Expired
- 1960-11-17 ES ES0262531A patent/ES262531A1/es not_active Expired
- 1960-11-22 LU LU39445D patent/LU39445A1/xx unknown
- 1960-11-25 BE BE597492A patent/BE597492A/fr unknown
-
1961
- 1961-02-15 FR FR852856A patent/FR943M/fr active Active
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| LU39445A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1961-01-24 |
| FR943M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1961-11-20 |
| ES262531A1 (es) | 1961-05-01 |
| BE597492A (fr) | 1961-03-15 |
| GB912946A (en) | 1962-12-12 |
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