DE1695771C2 - Verfahren zur Herstellung von N-(D-6-Methyl-8-isoergolenyl)-N',N'-diäthylharnstoff - Google Patents
Verfahren zur Herstellung von N-(D-6-Methyl-8-isoergolenyl)-N',N'-diäthylharnstoffInfo
- Publication number
- DE1695771C2 DE1695771C2 DE19671695771 DE1695771A DE1695771C2 DE 1695771 C2 DE1695771 C2 DE 1695771C2 DE 19671695771 DE19671695771 DE 19671695771 DE 1695771 A DE1695771 A DE 1695771A DE 1695771 C2 DE1695771 C2 DE 1695771C2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- isoergolenyl
- diethylurea
- solution
- yield
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000000126 substance Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- UUYMPWWTAQZUQB-IINYFYTJSA-N (6aR,9S)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carbohydrazide Chemical compound C1=CC(C2=C[C@@H](CN([C@@H]2C2)C)C(=O)NN)=C3C2=CNC3=C1 UUYMPWWTAQZUQB-IINYFYTJSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- OWAQXCQNWNJICI-UHFFFAOYSA-N benzene;chloroform Chemical compound ClC(Cl)Cl.C1=CC=CC=C1 OWAQXCQNWNJICI-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
- APRJFNLVTJWEPP-UHFFFAOYSA-N Diethylcarbamic acid Chemical compound CCN(CC)C(O)=O APRJFNLVTJWEPP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- -1 amino compound Chemical class 0.000 description 1
- 230000000794 anti-serotonin Effects 0.000 description 1
- 239000003420 antiserotonin agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- LTZNZBOEBQPMEQ-UHFFFAOYSA-N azide;hydrochloride Chemical compound Cl.[N-]=[N+]=[N-] LTZNZBOEBQPMEQ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007717 exclusion Effects 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
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS595666 | 1966-09-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1695771A1 DE1695771A1 (de) | 1972-03-02 |
| DE1695771C2 true DE1695771C2 (de) | 1984-04-19 |
Family
ID=5405520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671695771 Expired DE1695771C2 (de) | 1966-09-14 | 1967-09-06 | Verfahren zur Herstellung von N-(D-6-Methyl-8-isoergolenyl)-N',N'-diäthylharnstoff |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT277477B (enrdf_load_stackoverflow) |
| BE (1) | BE703487A (enrdf_load_stackoverflow) |
| CH (1) | CH487161A (enrdf_load_stackoverflow) |
| DE (1) | DE1695771C2 (enrdf_load_stackoverflow) |
| DK (1) | DK133876B (enrdf_load_stackoverflow) |
| FI (1) | FI47768C (enrdf_load_stackoverflow) |
| GB (1) | GB1174617A (enrdf_load_stackoverflow) |
| NL (1) | NL6712612A (enrdf_load_stackoverflow) |
| SE (1) | SE356514B (enrdf_load_stackoverflow) |
| YU (1) | YU31995B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2359128A1 (de) * | 1973-11-24 | 1975-06-12 | Schering Ag | Arzneimittel auf basis von lisurid und dessen physiologisch vertraeglichen salzen |
| EP0208417A3 (en) * | 1985-06-12 | 1989-09-06 | SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu | Use of 1-(8-alpha-ergolinyl)-3,3-diethyl urea derivatives in the treatment of endometritis |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE631856A (enrdf_load_stackoverflow) * | 1962-05-04 |
-
1967
- 1967-09-04 CH CH1232767A patent/CH487161A/de not_active IP Right Cessation
- 1967-09-05 BE BE703487D patent/BE703487A/xx not_active IP Right Cessation
- 1967-09-06 DE DE19671695771 patent/DE1695771C2/de not_active Expired
- 1967-09-08 GB GB4124267A patent/GB1174617A/en not_active Expired
- 1967-09-11 FI FI243567A patent/FI47768C/fi active
- 1967-09-13 YU YU178667A patent/YU31995B/xx unknown
- 1967-09-13 SE SE1264667A patent/SE356514B/xx unknown
- 1967-09-13 AT AT837067A patent/AT277477B/de active
- 1967-09-14 DK DK460567A patent/DK133876B/da unknown
- 1967-09-14 NL NL6712612A patent/NL6712612A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE703487A (enrdf_load_stackoverflow) | 1968-02-01 |
| AT277477B (de) | 1969-12-29 |
| NL6712612A (enrdf_load_stackoverflow) | 1968-03-15 |
| DK133876C (enrdf_load_stackoverflow) | 1976-12-27 |
| FI47768B (enrdf_load_stackoverflow) | 1973-11-30 |
| FI47768C (fi) | 1974-03-11 |
| GB1174617A (en) | 1969-12-17 |
| CH487161A (de) | 1970-03-15 |
| DE1695771A1 (de) | 1972-03-02 |
| SE356514B (enrdf_load_stackoverflow) | 1973-05-28 |
| DK133876B (da) | 1976-08-02 |
| YU178667A (en) | 1973-08-31 |
| YU31995B (en) | 1974-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |