AT367762B - METHOD FOR PRODUCING NEW ERGOL DERIVATIVES - Google Patents
METHOD FOR PRODUCING NEW ERGOL DERIVATIVESInfo
- Publication number
- AT367762B AT367762B AT0947076A AT947076A AT367762B AT 367762 B AT367762 B AT 367762B AT 0947076 A AT0947076 A AT 0947076A AT 947076 A AT947076 A AT 947076A AT 367762 B AT367762 B AT 367762B
- Authority
- AT
- Austria
- Prior art keywords
- formula
- compounds
- addition salts
- producing new
- bromine
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- -1 alkali metal cyanide Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 102000003946 Prolactin Human genes 0.000 description 2
- 108010057464 Prolactin Proteins 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 208000001287 Galactorrhea Diseases 0.000 description 1
- 206010017600 Galactorrhoea Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical compound C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8
-
- 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
- C07D457/06—Lysergic acid amides
-
- 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)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
<Desc/Clms Page number 1>
Die Erfindung betrifft ein Verfahren zur Herstellung neuer Ergolinderivate der Formel
EMI1.1
worin
X Wasserstoff, Chlor oder Brom,
R, Methyl oder Äthyl und R Alkyl mit 1 bis 4 Kohlenstoffatomen oder Allyl bedeuten, in Form der Basen oder ihrer Säureadditionssalze.
X bedeutet vorzugsweise Wasserstoff. Wenn nicht anders angegeben, enthält eine Alkylgruppe vorzugsweise 2, insbesondere 1 Kohlenstoffatom. R, bedeutet vorzugsweise Methyl, R2 vorzugsweise Alkyl. Eine bevorzugte Ausgangsverbindung umfasst Verbindungen der Formel (I), worin X Wasserstoff, R, und R2 je Methyl bedeuten.
EMI1.2
ren handelt. Von den in der DE-OS 2530577 enthaltenen Verbindungen unterscheiden sich die Verbindungen der Formel (I) dadurch, dass sie in Stellung 1 eine Alkyl- oder Allylgruppe aufweisen.
Erfindungsgemäss gelangt man zu den Verbindungen der Formel (I), indem man Verbindungen der Formel
EMI1.3
worin
Z für Chlor, Brom oder einen aliphatischen oder aromatischen Sulfonyloxyrest steht und
X, R, und Ru obige Bedeutung besitzen, mit einem Alkalimetallcyanid umsetzt und die so erhaltenen Verbindungen der Formel (I) in Form der Basen oder von Säureadditionssalzen gewinnt.
Das Verfahren kann analog zu bekannten Methoden erfolgen. Der Rest Z steht in den Verbindungen der Formel (II) vorzugsweise für den Mesyloxy- oder den p-Tosyloxyrest. Man geht beispielsweise so vor, dass man eine Verbindung der Formel (II) mit einem Alkalimetallcyanid, wie Natrium-oder Kaliumcyanid, umsetzt. Man arbeitet mit Vorteil unter Erwärmen, z. B. auf 50 bis 100 C.
Die Verbindungen der Formel (I) können z. B. in freier Form als Base oder in Form ihrer
<Desc/Clms Page number 2>
Additionssalze mit Säuren vorliegen. Aus den freien Basen lassen sich in bekannter Weise Säureadditionssalze herstellen und umgekehrt.
Die Ausgangsprodukte sind bekannt oder nach an sich bekannten Methoden herstellbar.
Die Verbindungen der Formel (I) in freier Form oder in Form von physiologisch verträglichen Additionssalzen mit Säuren zeichnen sich durch interessante pharmakodynamische Eigenschaften aus. Sie können als Heilmittel verwendet werden. Diese Verbindungen können auf Grund ihrer dopaminergen Eigenschaften bei der Behandlung von Morbus Parkinson und depressiven Zuständen Anwendung finden.
Sie besitzen ebenfalls eine Prolactin-sekretionshemmende Wirkung. Prolactin-sekretionshemmende Verbindungen können z. B. zur Prophylaxe und Therapie von physiologischer Lactation und Galactorrhoe Anwendung finden.
Heilmittel können eine Verbindung der Formel (I) in freier Form oder in Form ihrer physiologisch verträglichen Additionssalze mit Säuren enthalten. Diese Heilmittel, beispielsweise eine Lösung oder. eine Tablette, können nach bekannten Methoden, unter Verwendung der üblichen Hilfsund Trägerstoffe, hergestellt werden.
Das nachfolgende Beispiel erläutert die Erfindung.
Die Temperaturangaben erfolgen in Celsiusgraden.
Beispiel 1 : 1, 6-Dimethyl-8a-acetonitril-ergolin I
2,89 g 8 a -Chlormethyl-l, 6-dimethyl-ergolin I werden in 20 ml Dimethylsulfoxyd gelöst, mit einer Lösung von 1,95 g Kaliumcyanid in 10 ml Wasser versetzt und das Reaktionsgemisch 5 h bei 1100 gerührt. Darauf wird zwischen Methylenchlorid und 2 N Ammoniak verteilt, die organischen Phasen mit Natriumsulfat getrocknet und eingeengt und der Rückstand an 100 g Kieselgel mittels Methylenchlorid/Methanol (95 : 5) chromatographiert und die reines l, 6-Dimethyl-8a-aceto- nitril-ergolin I enthaltenden Fraktionen eingedampft und als Hydrogentartrat aus Aceton-Petrol- äther kristallisiert.
Fp. : 115 bis 119
EMI2.1
<Desc / Clms Page number 1>
The invention relates to a process for the preparation of new ergoline derivatives of the formula
EMI1.1
wherein
X is hydrogen, chlorine or bromine,
R, methyl or ethyl and R are alkyl having 1 to 4 carbon atoms or allyl, in the form of the bases or their acid addition salts.
X is preferably hydrogen. Unless otherwise stated, an alkyl group preferably contains 2, in particular 1, carbon atom. R is preferably methyl, R2 is preferably alkyl. A preferred starting compound comprises compounds of the formula (I) in which X is hydrogen, R and R2 are each methyl.
EMI1.2
ren acts. The compounds of the formula (I) differ from the compounds contained in DE-OS 2530577 in that they have an alkyl or allyl group in position 1.
According to the invention, the compounds of the formula (I) are obtained by using compounds of the formula
EMI1.3
wherein
Z represents chlorine, bromine or an aliphatic or aromatic sulfonyloxy radical and
X, R, and Ru have the above meaning, reacted with an alkali metal cyanide and the compounds of the formula (I) thus obtained are obtained in the form of the bases or of acid addition salts.
The method can be carried out analogously to known methods. The radical Z in the compounds of the formula (II) is preferably the mesyloxy or p-tosyloxy radical. The procedure is, for example, to react a compound of the formula (II) with an alkali metal cyanide, such as sodium or potassium cyanide. It is advantageous to work with heating, e.g. B. to 50 to 100 C.
The compounds of formula (I) z. B. in free form as a base or in the form of their
<Desc / Clms Page number 2>
Addition salts with acids are present. Acid addition salts can be prepared from the free bases in a known manner and vice versa.
The starting products are known or can be produced by methods known per se.
The compounds of formula (I) in free form or in the form of physiologically tolerable addition salts with acids are distinguished by interesting pharmacodynamic properties. They can be used as a remedy. Because of their dopaminergic properties, these compounds can be used in the treatment of Parkinson's disease and depressive conditions.
They also have a prolactin secretion-inhibiting effect. Prolactin secretion-inhibiting compounds can e.g. B. for the prophylaxis and therapy of physiological lactation and galactorrhea.
Medicaments can contain a compound of formula (I) in free form or in the form of its physiologically tolerable addition salts with acids. These remedies, for example a solution or. a tablet, can be prepared according to known methods, using the usual auxiliaries and carriers.
The following example explains the invention.
The temperatures are given in degrees Celsius.
Example 1: 1, 6-Dimethyl-8a-acetonitrile-ergoline I
2.89 g of 8 a -chloromethyl-1,6-dimethyl-ergoline I are dissolved in 20 ml of dimethyl sulfoxide, a solution of 1.95 g of potassium cyanide in 10 ml of water is added and the reaction mixture is stirred at 1100 for 5 h. It is then partitioned between methylene chloride and 2 N ammonia, the organic phases are dried with sodium sulfate and concentrated, and the residue is chromatographed on 100 g of silica gel using methylene chloride / methanol (95: 5) and the pure 1,6-dimethyl-8a-aceto-nitrile Fractions containing ergoline I are evaporated and crystallized as hydrogen tartrate from acetone / petroleum ether.
Mp .: 115 to 119
EMI2.1
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0947076A AT367762B (en) | 1976-12-21 | 1976-12-21 | METHOD FOR PRODUCING NEW ERGOL DERIVATIVES |
| AT759579A AT376221B (en) | 1975-12-23 | 1979-11-30 | METHOD FOR PRODUCING NEW ERGOL DERIVATIVES |
| AT759479A AT370102B (en) | 1975-12-23 | 1979-11-30 | METHOD FOR PRODUCING NEW ERGOL DERIVATIVES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0947076A AT367762B (en) | 1976-12-21 | 1976-12-21 | METHOD FOR PRODUCING NEW ERGOL DERIVATIVES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA947076A ATA947076A (en) | 1981-12-15 |
| AT367762B true AT367762B (en) | 1982-07-26 |
Family
ID=3614428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0947076A AT367762B (en) | 1975-12-23 | 1976-12-21 | METHOD FOR PRODUCING NEW ERGOL DERIVATIVES |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT367762B (en) |
-
1976
- 1976-12-21 AT AT0947076A patent/AT367762B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA947076A (en) | 1981-12-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |