IE49611B1 - A 2-methyl ergot peptide alkaloid - Google Patents
A 2-methyl ergot peptide alkaloidInfo
- Publication number
- IE49611B1 IE49611B1 IE1388/85A IE138885A IE49611B1 IE 49611 B1 IE49611 B1 IE 49611B1 IE 1388/85 A IE1388/85 A IE 1388/85A IE 138885 A IE138885 A IE 138885A IE 49611 B1 IE49611 B1 IE 49611B1
- Authority
- IE
- Ireland
- Prior art keywords
- compounds
- compound
- indicated
- methyl
- acid
- Prior art date
Links
- 229930015720 peptide alkaloid Natural products 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical group 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 229950001817 alpha-ergocryptine Drugs 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 235000011087 fumaric acid Nutrition 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 102000003946 Prolactin Human genes 0.000 description 2
- 108010057464 Prolactin Proteins 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 206010042008 Stereotypy Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229960001866 silicon dioxide Drugs 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- ZCQPDHIMSLIIDW-MEBBXXQBSA-N (6ar,9r)-5,7-dimethyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=C(C)NC3=C1 ZCQPDHIMSLIIDW-MEBBXXQBSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- KRXAVBPUAIKSFF-UHFFFAOYSA-N 3,4-dihydrodithiine Chemical compound C1CC=CSS1 KRXAVBPUAIKSFF-UHFFFAOYSA-N 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 229940125688 antiparkinson agent Drugs 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 230000002746 orthostatic effect Effects 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
The present invention relates to the ergot peptide alkaloid 2-methyl-a-ergocryptine of formula I The free base form of the compound of formula I may be converted 5 into acid addition salt forms in conventional manner, and vice versa. Suitable salts for acid addition formation include, for example, hydrochloric acid, maleic acid, sulphuric acid, fumaric acid and tartaric acid.
The following examples illustrate the preparation of the compound of formula Ϊ. All temperatures are in degrees Centigrade and are uncorrected.
EXAMPLE 1: 2-methyl-a-ergocryptine 2.82 g (10 mMol) anhydrous 2-methyl lysergic acid are dissolved in 25 ml absolute dimethylformamide on the addition of 2.28 g (20 mMol) trifiuoroacetic acid, and with stirring brought to -1O°C. At this temperature, a mixture of 2.52 g (12 mMol) trifiuoroacetic acid anhydride in 12 ml absolute acetonitrile is added dropwise and the resultant clear solution is stirred for 10 minutes. 12 ml pyridine and 1.81 g (5 mMol) (2R,5S,10aS,10bS)-2-amino-5lo isobutyl-10b-hydroxy-2-isopropyl-octahydro-3,6-dioxo-8Hoxazolo[3,2-a]pyrrolo(2,l-c]pyrazine hydrochloride are added and the reaction mixture is stirred for 1 hour at between -10° and 0°.
To work up, 200 ml methylene chloride is added and the mixture is well shaken with 100 ml 2N sodium carbonate solution. The organic phase is separated and the aqueous phase is washed three times with 100 ml methylene chloride. The combined organic phase are dried over sodium sulphate and concentrated in a vacuum. The residue is chromatographed .20 on silicagel eluted with 2% methanol in methylene chloride to give pure 2-methyl-a-ergocryptinine. M.pt. 225-227° (de20 comp) from methylene chxoride/ether; [a] θ =+ 412° (c = 0.4 in chloroform).
Elution with 3% methanol in methylene chloride yielded 2-methyl-a-ergocryptine. The hydrogen fumarate is obtained by reaction with 1 equivalent of fumaric acid.M. pt. 181-184° (decomp) [a]2° = + 25.0 (c=0.2 in ethanol).
EXAMPLE 2: 2-methyl-g-ergocryptine a) thian^^yl) 2"Ze£9°°£YEtin£ A solution of 11.5 g (20 mMol) of a-ergocryptlne in absolute chloroform - is added dropwise quickly s to a vigorously stirred solution of about 1.2 equivalents of 2-chloro-l,3-dithiane in absolute chloroform ——-cooled to -15°. The reaction mixture is allowed to warm to 5 to 10° resulting in a· black dirty precipitate. The mixture is stirred at 10° and worked up. Working up comprises IO making the mixture alkaline with 2N sodium carbonate solution and extracting with methylene chloride/methanol (9:1). The organic phases are washed with saturated sodium hydrogen carbonate solution, dried over sodium sulphate, filtered and evaporated. 16.7 g of a foam con- 15 taining the heading compound is obtained which can be used further as such or else chromatographed on silicagel using 2» CHjOH in CHjClj as eluant to yield the heading compound. The hydrogen maleate of the heading compound has M.pt 163165* (from ethyl acetate/ether); (aJD^ =· + 111’ (c 20 0.55 in dimethylformamide). 105 ml of an aqueous suspension of Raney Nickel W6 is repeatedly washed with 100 ml amounts of acetone/ dimethylformamide (8:2). Samples of the supernatant liquid are taken as the acetone/dimethylformamide is added. When the sample on treatment with methylene chloride yields no unclarity, then the washing with acetone/dimethylformamide is stopped. 7.5 g of 2-(l,3-dithian-2-yl)-a-ergoeryptine in 150 ml acetone containing 20% dimethylformamide are treated with 105 ml or this treated Raney Nickel W6 in 100 ml of the same solvent. After 15 minutes, the catalyst is filtered off and it is washed several times with about 300 ml of the solvent mixture. The solvent is distilled IS from the combined organic phases to give a brown foam which is taken up in ethanol and reacted with fumaric acid (1 equivalent) to give the hydrogen fumarate of the heading compound. M.pt. 181-184° (decomp); [α]^θ = + 25.1 (c = 0.2 ethanol). 2.0 The compound of formula Γ and its pharmacologically acceptable acid addition salts, hereinafter referred to as compounds of the invention, exhibit pharmacological activity in animals.
The compounds of the invention exhibit a dopaminergic stimulating effect as indicated in standard animal > tests. For example, the compounds when administered at from about 0.03 to about.3 mg/kg inhibit the rotations induced by i.p. injection of 6-hydroxydopamine into the substantia nigra unilaterally into the nigra-neostriat&la dopamine pathway [method according to U. Ungerstaedt Acta physiol, scand. Suppl. 367, 64-93 (1973)1. The compounds also inhibit stereotypy in the apomorphine stereotypy test in i.p. administration ot about 30 mg/kg of the compound.
The compounds are therefore indicated for use as anti-parkinson agents for e.g. for the treatment of Morbus IS Parkinson.
As indicated daily dosage is in the range from about 0.5 to about 100 mg, conveniently given in divided doses 2 to 4 times a day in unit dosage form containing from about 0.1 mg to about 50 mg of the compounds, or in 2.0 sustained release form.
The compounds of the invention furthermore exhibit prolactin secretion inhibitory activity, as indicated by standard tests, e.,g. by inhibition of implanatation in the rat on s.c. administration of from about 0.01 to about 1 mg/ 2.S kg of the compounds and an inhibit'-n of lactation on p.o. administration of from about 1 to about 10 mg/kg of the compounds.
The compounds are therefore indicated for use as prolactin secretion inhibitors .
An indicated daily dosage is in the range from about 0.5 to about 100 mg, conveniently given in divided S doses 2 to 4 times a day in unit dosage form containing from about 0.1 mg to about 50 mg of the compounds, or in sustained release form.
The compounds of the invention additionally exhibit anti-depressant activity, as indicated by an inhibition of IO ptosis and catalepsy induced by reserpine in rats on i.p. administration of 1 to 50 mg/kg of the compounds.
The compounds are therefore indicated for use as anti-depressant agents.
An indicated daily dosage is in the range from about 1·5 0.5 to about 100 mg, conveniently given in divided doses to 4 times a day in unit dosage form containing from about 0.1 mg to about 50 mg of the compounds, or in sustained release form.
The compounds of the invention furthermore exhibit 2.0 vigilance increasing activity as indicated by an increase in the wake phase and a decrease in the paroxodical and classical sleep phases in the sleep/wake cycle test in the rat in p.o. administration of from about 5 to about 20 mg/kg of the compounds.
The compounds are therefore indicated for use as vigilance increasing agents.
The compounds of the invention additionally exhibit 48611 a vasoconstricting effect in standard animal tests, e.g. in the Mellander-cat test [Angiologica 3, 77-99 (1966)] by an arterial vasotonic effect, on i.a. administration of from about 5 to about 45 yug/kg animal body weight.
The compounds are therefore indicated for use in the treatment of migraine and orthostatic disorders.
For the above two indications, an indicated daily dosage is in the range from about 0.5 to about 100 mg , conveniently given in to divided doses 2 to 4 times a day in unit dosage form containing from about 0.1 mg to about 50 mg of the compounds admixed with a solid or liquid pharmaceutical carrier or diluent.
The compounds of the invention may be administered in IS pharmaceutically acceptable acid addition salt form. Such acid addition salt forms exhibit the same order of activity as the free base forms and are readily prepared in conventional manner. The present invention also provides a pharmaceutical composition comprising the compound of formu3.0 la I, in free base form or in pharmaceutically acceptable acid addition salt form, in association with a pharmaceutical carrier or diluent.
Claims (4)
1. The compound of formula I
2. An acid addition salt form of the compound of claim 1.
3. A pharmaceutical composition comprising the compound of
4. 5 claim 1 in free base form or in pharmaceutically acceptable acid addition salt form, in association with a pharmaceutical carrier or diluent.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH547979 | 1979-06-12 | ||
CH547879 | 1979-06-12 | ||
CH547779A CH643560A5 (en) | 1979-06-12 | 1979-06-12 | Ergopeptin derivatives, their preparation and use |
CH547679A CH642082A5 (en) | 1979-06-12 | 1979-06-12 | Ergopeptin derivatives, their preparation and use |
IE1206/80A IE49610B1 (en) | 1979-06-12 | 1980-06-11 | Ergot peptide derivatives,their preparation and pharmaceutical compositions containing them |
Publications (2)
Publication Number | Publication Date |
---|---|
IE851388L IE851388L (en) | 1980-12-12 |
IE49611B1 true IE49611B1 (en) | 1985-10-30 |
Family
ID=27509241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE1388/85A IE49611B1 (en) | 1979-06-12 | 1980-06-11 | A 2-methyl ergot peptide alkaloid |
Country Status (1)
Country | Link |
---|---|
IE (1) | IE49611B1 (en) |
-
1980
- 1980-06-11 IE IE1388/85A patent/IE49611B1/en unknown
Also Published As
Publication number | Publication date |
---|---|
IE851388L (en) | 1980-12-12 |
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