CS195905B1 - 6-substituted derivatives of d-8-ergolin-i-ylacetic acid amide and process for preparing thereof - Google Patents
6-substituted derivatives of d-8-ergolin-i-ylacetic acid amide and process for preparing thereof Download PDFInfo
- Publication number
- CS195905B1 CS195905B1 CS767932A CS793276A CS195905B1 CS 195905 B1 CS195905 B1 CS 195905B1 CS 767932 A CS767932 A CS 767932A CS 793276 A CS793276 A CS 793276A CS 195905 B1 CS195905 B1 CS 195905B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- ergolin
- ylacetamide
- hydrazides
- boiling point
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 8
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 239000007868 Raney catalyst Substances 0.000 claims description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000000085 anti-nidation effect Effects 0.000 abstract 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 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 230000028327 secretion Effects 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
- QTWZVXVIOJJQTN-WQRMPROISA-N 2-[(6ar,9s,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]acetamide;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1=CC([C@H]2C[C@@H](CC(N)=O)CN([C@@H]2C2)C)=C3C2=CNC3=C1 QTWZVXVIOJJQTN-WQRMPROISA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 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 3
- 239000011976 maleic acid Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 102000003946 Prolactin Human genes 0.000 description 2
- 108010057464 Prolactin Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000000474 nursing effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108010086677 Gonadotropins Proteins 0.000 description 1
- 102000006771 Gonadotropins Human genes 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000004451 Pituitary Gonadotropins Human genes 0.000 description 1
- 108010081865 Pituitary Gonadotropins Proteins 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000002622 gonadotropin Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000009806 oophorectomy Methods 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C07D457/02—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS767932A CS195905B1 (en) | 1976-12-06 | 1976-12-06 | 6-substituted derivatives of d-8-ergolin-i-ylacetic acid amide and process for preparing thereof |
| SE7712611A SE7712611L (sv) | 1976-12-06 | 1977-11-08 | Nya 6-substituerade derivat av d-8-ergolin-i-ylacetamid, salter derav och ett forfarande for framstellning derav samt kompositioner innehallande dessa derivat |
| FI773498A FI773498A7 (fi) | 1976-12-06 | 1977-11-18 | Nya substituerade derivat av d-8-ergolin-1-ylaettiksyraamid deras salter foerfarande foer deras framstaellning och dessa innehaollande farmaceutiska medel |
| GB48536/77A GB1540787A (en) | 1976-12-06 | 1977-11-22 | 6-substituted d-8-ergolin-i-ylacetamides |
| BE182902A BE861161A (fr) | 1976-12-06 | 1977-11-24 | Nouveaux derives de d-8-ergolin-i-ylacetamide substitues en position 6, leurs sels, leur procede de preparation et compositions |
| FR7735948A FR2372833B1 (OSRAM) | 1976-12-06 | 1977-11-29 | |
| JP14333077A JPS5384995A (en) | 1976-12-06 | 1977-12-01 | 66substituted derivative of dd88ergolineeiiylacetamide salts thereof process for preparing same and medicine containing same |
| DE19772753880 DE2753880A1 (de) | 1976-12-06 | 1977-12-02 | Neue 6-substituierte derivate von d-8-ergolin-i-ylessigsaeureamid und ihre salze, verfahren zu ihrer herstellung und pharmazeutische mittel |
| AU31160/77A AU510710B2 (en) | 1976-12-06 | 1977-12-02 | 6-substituted derivatives of d 8-ergolin-1-ylacetamide |
| CA292,418A CA1065860A (en) | 1976-12-06 | 1977-12-05 | 6-substituted derivatives of d-8-ergolin-1-ylacetamide, their salts, a process for the preparation thereof and composition containing same |
| ES464753A ES464753A1 (es) | 1976-12-06 | 1977-12-05 | Procedimiento para producir nuevos derivados 6-sustituidos de d-8-ergolin-i-ilacetamida. |
| AT867977A AT355734B (de) | 1976-12-06 | 1977-12-05 | Verfahren zur herstellung neuer 6-substi- tuierter derivate von d-8-ergolin-i-ylessig- saeureamid und deren salze |
| US05/857,994 US4182883A (en) | 1976-12-06 | 1977-12-06 | D-6-allyl-8-ergol-I-ylacetamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS767932A CS195905B1 (en) | 1976-12-06 | 1976-12-06 | 6-substituted derivatives of d-8-ergolin-i-ylacetic acid amide and process for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195905B1 true CS195905B1 (en) | 1980-02-29 |
Family
ID=5429294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS767932A CS195905B1 (en) | 1976-12-06 | 1976-12-06 | 6-substituted derivatives of d-8-ergolin-i-ylacetic acid amide and process for preparing thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4182883A (OSRAM) |
| JP (1) | JPS5384995A (OSRAM) |
| AT (1) | AT355734B (OSRAM) |
| AU (1) | AU510710B2 (OSRAM) |
| BE (1) | BE861161A (OSRAM) |
| CA (1) | CA1065860A (OSRAM) |
| CS (1) | CS195905B1 (OSRAM) |
| DE (1) | DE2753880A1 (OSRAM) |
| ES (1) | ES464753A1 (OSRAM) |
| FI (1) | FI773498A7 (OSRAM) |
| FR (1) | FR2372833B1 (OSRAM) |
| GB (1) | GB1540787A (OSRAM) |
| SE (1) | SE7712611L (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI76085C (fi) * | 1981-07-21 | 1988-09-09 | Erba Farmitalia | Foerfarande foer framstaellning av ergolinderivat. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1439953A (fr) * | 1965-01-28 | 1966-05-27 | Sandoz Sa | Nouveaux dérivés de l'ergolène et leur préparation |
| US3966941A (en) * | 1970-09-23 | 1976-06-29 | Spofa United Pharmaceutical Works | Composition for preventing lactation or pregnancy in mammals and the method for using the same |
| US3920664A (en) * | 1972-07-21 | 1975-11-18 | Lilly Co Eli | D-2-halo-6-alkyl-8-substituted ergolines and related compounds |
| NL7400790A (OSRAM) * | 1973-02-02 | 1974-08-06 | ||
| CS177530B1 (en) * | 1974-07-19 | 1977-07-29 | Miroslav Semonsky | New nbeta-substituted derivatives of b-beta-aminoethyl-ergoline-i their salts and methods for the production thereof |
| US3959288A (en) * | 1974-12-13 | 1976-05-25 | Eli Lilly And Company | 8-Oxymethylergolines and process therefor |
-
1976
- 1976-12-06 CS CS767932A patent/CS195905B1/cs unknown
-
1977
- 1977-11-08 SE SE7712611A patent/SE7712611L/xx unknown
- 1977-11-18 FI FI773498A patent/FI773498A7/fi not_active Application Discontinuation
- 1977-11-22 GB GB48536/77A patent/GB1540787A/en not_active Expired
- 1977-11-24 BE BE182902A patent/BE861161A/xx unknown
- 1977-11-29 FR FR7735948A patent/FR2372833B1/fr not_active Expired
- 1977-12-01 JP JP14333077A patent/JPS5384995A/ja active Pending
- 1977-12-02 AU AU31160/77A patent/AU510710B2/en not_active Expired
- 1977-12-02 DE DE19772753880 patent/DE2753880A1/de not_active Withdrawn
- 1977-12-05 CA CA292,418A patent/CA1065860A/en not_active Expired
- 1977-12-05 ES ES464753A patent/ES464753A1/es not_active Expired
- 1977-12-05 AT AT867977A patent/AT355734B/de not_active IP Right Cessation
- 1977-12-06 US US05/857,994 patent/US4182883A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE7712611L (sv) | 1978-06-07 |
| US4182883A (en) | 1980-01-08 |
| AU510710B2 (en) | 1980-07-10 |
| FR2372833B1 (OSRAM) | 1980-05-16 |
| CA1065860A (en) | 1979-11-06 |
| DE2753880A1 (de) | 1978-06-08 |
| ES464753A1 (es) | 1978-09-01 |
| FI773498A7 (fi) | 1978-06-07 |
| AU3116077A (en) | 1979-06-07 |
| ATA867977A (de) | 1979-08-15 |
| BE861161A (fr) | 1978-03-16 |
| FR2372833A1 (OSRAM) | 1978-06-30 |
| AT355734B (de) | 1980-03-25 |
| JPS5384995A (en) | 1978-07-26 |
| GB1540787A (en) | 1979-02-14 |
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