CS207489B2 - Method of making new ergoline derivates - Google Patents

Method of making new ergoline derivates Download PDF

Info

Publication number: CS207489B2
Authority: CS; Czechoslovakia
Prior art keywords: alkyl; methyl; carbon atoms; title compound; yield
Prior art date: 1976-12-06

Application number

CS778087A

Other languages

Czech (cs)

English (en)

Inventor

Enzo Beacco

Luigi Bernardi

Salle Enrico Di

Giovanni Falconi

Bianca Patelli

Original Assignee

Farmaceutici Italia

Priority date (The priority date 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 date listed.)

1976-12-06

Filing date

1977-12-05

Publication date

1981-07-31

1977-12-05 Application filed by Farmaceutici Italia filed Critical Farmaceutici Italia

1981-07-31 Publication of CS207489B2 publication Critical patent/CS207489B2/cs

Links

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 compound 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 title claims abstract description 11
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 38
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052794 bromium Inorganic materials 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
239000000460 chlorine Substances 0.000 claims abstract description 4
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
239000012434 nucleophilic reagent Substances 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
150000008064 anhydrides Chemical class 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
-1 substituted-phenyl Chemical group 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
229910052736 halogen Inorganic materials 0.000 abstract description 2
150000002367 halogens Chemical group 0.000 abstract description 2
125000005842 heteroatom Chemical group 0.000 abstract description 2
125000000896 monocarboxylic acid group Chemical group 0.000 abstract description 2
229910052760 oxygen Inorganic materials 0.000 abstract description 2
239000001301 oxygen Substances 0.000 abstract description 2
229920006395 saturated elastomer Polymers 0.000 abstract description 2
239000005864 Sulphur Substances 0.000 abstract 1
125000001424 substituent group Chemical group 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
241000700159 Rattus Species 0.000 description 8
OULXAFABNHTZLI-SKNXHYNKSA-N 1-[(6ar,10ar)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-yl]ethanone Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)C(=O)C)C2)=C3C2=CNC3=C1 OULXAFABNHTZLI-SKNXHYNKSA-N 0.000 description 6
WDLVDQMIHSOUPY-IIWDCPNDSA-N 1-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-bromoethanone Chemical compound C1=CC([C@H]2CC(CN([C@@H]2C2)C)C(=O)CBr)=C3C2=CNC3=C1 WDLVDQMIHSOUPY-IIWDCPNDSA-N 0.000 description 5
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 description 5
229960002802 bromocriptine Drugs 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000001263 anti-prolactin effect Effects 0.000 description 3
239000002895 emetic Substances 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
HTKHLVIOITZWSN-PXFYRTPJSA-N 1-[(6ar,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]-2-bromoethanone Chemical compound C1=CC([C@H]2CC(CN([C@@H]2C2)C)C(=O)CBr)=C3C2=CN(C)C3=C1 HTKHLVIOITZWSN-PXFYRTPJSA-N 0.000 description 2
CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
102000003946 Prolactin Human genes 0.000 description 2
108010057464 Prolactin Proteins 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000002513 implantation Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
229940097325 prolactin Drugs 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
230000001629 suppression Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
MCCXTHKWNDYNKL-HUFXEGEASA-N (6ar,9r)-4,7-dimethyl-5,5a,6,6a,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C([C@H](CN(C)[C@@H]1C2)C(O)=O)=C1C1=CC=CC3=C1C2CN3C MCCXTHKWNDYNKL-HUFXEGEASA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
RRVBCOGQWXLOIF-RMNMTYGKSA-N 1-[(6ar,10ar)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-yl]-2-morpholin-4-ylethanone Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3N(C)C=C(C=23)C1)C1)CC1C(=O)CN1CCOCC1 RRVBCOGQWXLOIF-RMNMTYGKSA-N 0.000 description 1
ZWTDLHNMTMBVEV-GERZZCHPSA-N 1-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-(diethylamino)ethanone Chemical compound C1=CC([C@H]2CC(CN(C)[C@@H]2C2)C(=O)CN(CC)CC)=C3C2=CNC3=C1 ZWTDLHNMTMBVEV-GERZZCHPSA-N 0.000 description 1
WICFOCORUNSCHI-IIWDCPNDSA-N 1-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-hydroxyethanone Chemical compound C1=CC([C@H]2CC(CN([C@@H]2C2)C)C(=O)CO)=C3C2=CNC3=C1 WICFOCORUNSCHI-IIWDCPNDSA-N 0.000 description 1
FUSRBCOOWOTXCG-GERZZCHPSA-N 1-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-morpholin-4-ylethanone Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3NC=C(C=23)C1)C1)CC1C(=O)CN1CCOCC1 FUSRBCOOWOTXCG-GERZZCHPSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
208000001287 Galactorrhea Diseases 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 1
VSHCYSYLUCDUAQ-KXBOQVSUSA-N [2-[(6aR,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2-oxoethyl] 2,6-dimethylbenzoate Chemical compound CC1=C(C(=O)OCC(=O)C2CN([C@@H]3CC4=CNC5=CC=CC([C@H]3C2)=C45)C)C(=CC=C1)C VSHCYSYLUCDUAQ-KXBOQVSUSA-N 0.000 description 1
229940008309 acetone / ethanol Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
208000007502 anemia Diseases 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
210000003756 cervix mucus Anatomy 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
230000004720 fertilization Effects 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000000960 hypophysis hormone Substances 0.000 description 1
230000036512 infertility Effects 0.000 description 1
208000000509 infertility Diseases 0.000 description 1
231100000535 infertility Toxicity 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000001990 intravenous 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
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical compound C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 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
229940103091 potassium benzoate Drugs 0.000 description 1
235000010235 potassium benzoate Nutrition 0.000 description 1
239000004300 potassium benzoate Substances 0.000 description 1
YQFJGGDKUUOQFA-UHFFFAOYSA-M potassium;1h-pyrrole-2-carboxylate Chemical compound [K+].[O-]C(=O)C1=CC=CN1 YQFJGGDKUUOQFA-UHFFFAOYSA-M 0.000 description 1
WFMNHCSATCWAAQ-UHFFFAOYSA-M potassium;2,2-dimethylpropanoate Chemical compound [K+].CC(C)(C)C([O-])=O WFMNHCSATCWAAQ-UHFFFAOYSA-M 0.000 description 1
MRFNZGPGVYIEFP-UHFFFAOYSA-M potassium;2,6-dimethoxybenzoate Chemical compound [K+].COC1=CC=CC(OC)=C1C([O-])=O MRFNZGPGVYIEFP-UHFFFAOYSA-M 0.000 description 1
MISVOFAYXMKGCO-UHFFFAOYSA-M potassium;2,6-dimethylbenzoate Chemical compound [K+].CC1=CC=CC(C)=C1C([O-])=O MISVOFAYXMKGCO-UHFFFAOYSA-M 0.000 description 1
VWQYYVHMLGMRSQ-UHFFFAOYSA-M potassium;5-bromopyridine-3-carboxylate Chemical compound [K+].[O-]C(=O)C1=CN=CC(Br)=C1 VWQYYVHMLGMRSQ-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002250 progressing effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
QNRDAHPABVDRHI-UHFFFAOYSA-M sodium;5-methylpyrimidine-2-thiolate Chemical compound [Na+].CC1=CN=C([S-])N=C1 QNRDAHPABVDRHI-UHFFFAOYSA-M 0.000 description 1
KFLRWGSAMLBHBV-UHFFFAOYSA-M sodium;pyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CN=C1 KFLRWGSAMLBHBV-UHFFFAOYSA-M 0.000 description 1
PVXCGWNPDFFPOV-UHFFFAOYSA-M sodium;pyridine-4-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=NC=C1 PVXCGWNPDFFPOV-UHFFFAOYSA-M 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
238000005303 weighing 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
- C07D457/02—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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CS778087A 1976-12-06 1977-12-05 Method of making new ergoline derivates CS207489B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB50746/76A GB1580448A (en)	1976-12-06	1976-12-06	8 -acetyl-6-methyl-ergoline i derivatives

Publications (1)

Publication Number	Publication Date
CS207489B2 true CS207489B2 (en)	1981-07-31

Family

ID=10457193

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS778087A CS207489B2 (en)	1976-12-06	1977-12-05	Method of making new ergoline derivates

Country Status (19)

Country	Link
US (1)	US4196288A (fr)
JP (1)	JPS5371099A (fr)
AT (1)	AT361138B (fr)
AU (1)	AU3111277A (fr)
BE (1)	BE861480A (fr)
CA (1)	CA1101848A (fr)
CS (1)	CS207489B2 (fr)
DE (1)	DE2754028A1 (fr)
DK (1)	DK535777A (fr)
FR (1)	FR2372834A1 (fr)
GB (1)	GB1580448A (fr)
HU (1)	HU177143B (fr)
NL (1)	NL7713226A (fr)
NO (1)	NO774133L (fr)
NZ (1)	NZ185837A (fr)
SE (1)	SE7713720L (fr)
SU (1)	SU736872A3 (fr)
YU (1)	YU283177A (fr)
ZA (1)	ZA777174B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE879822A (fr) *	1979-02-20	1980-03-03	Erba Farmitalia	Derives de l'ergoline
GB9711043D0 (en) *	1997-05-29	1997-07-23	Ciba Geigy Ag	Organic compounds
CN101481405A (zh) *	2001-06-08	2009-07-15	研究及应用科学协会股份有限公司	生长激素释放抑制因子-多巴胺嵌合类似物

1976
- 1976-12-06 GB GB50746/76A patent/GB1580448A/en not_active Expired
1977
- 1977-11-30 NL NL7713226A patent/NL7713226A/xx not_active Application Discontinuation
- 1977-12-01 AU AU31112/77A patent/AU3111277A/en active Pending
- 1977-12-01 AT AT860477A patent/AT361138B/de not_active IP Right Cessation
- 1977-12-01 US US05/856,536 patent/US4196288A/en not_active Expired - Lifetime
- 1977-12-01 YU YU02831/77A patent/YU283177A/xx unknown
- 1977-12-02 ZA ZA00777174A patent/ZA777174B/xx unknown
- 1977-12-02 DK DK535777A patent/DK535777A/da unknown
- 1977-12-02 NZ NZ185837A patent/NZ185837A/xx unknown
- 1977-12-02 CA CA292,311A patent/CA1101848A/fr not_active Expired
- 1977-12-02 HU HU77SO1204A patent/HU177143B/hu unknown
- 1977-12-02 NO NO774133A patent/NO774133L/no unknown
- 1977-12-02 SE SE7713720A patent/SE7713720L/xx unknown
- 1977-12-05 JP JP14599077A patent/JPS5371099A/ja active Pending
- 1977-12-05 BE BE183147A patent/BE861480A/fr unknown
- 1977-12-05 SU SU772548999A patent/SU736872A3/ru active
- 1977-12-05 CS CS778087A patent/CS207489B2/cs unknown
- 1977-12-05 DE DE19772754028 patent/DE2754028A1/de not_active Withdrawn
- 1977-12-05 FR FR7736504A patent/FR2372834A1/fr active Granted

Also Published As

Publication number	Publication date
NZ185837A (en)	1979-11-01
HU177143B (en)	1981-07-28
NO774133L (no)	1978-06-07
DK535777A (da)	1978-06-07
AU3111277A (en)	1979-06-07
US4196288A (en)	1980-04-01
SE7713720L (sv)	1978-06-07
FR2372834A1 (fr)	1978-06-30
GB1580448A (en)	1980-12-03
ATA860477A (de)	1980-07-15
AT361138B (de)	1981-02-25
BE861480A (fr)	1978-03-31
YU283177A (en)	1983-12-31
CA1101848A (fr)	1981-05-26
JPS5371099A (en)	1978-06-24
FR2372834B1 (fr)	1981-11-27
DE2754028A1 (de)	1978-06-08
SU736872A3 (ru)	1980-05-25
NL7713226A (nl)	1978-06-08
ZA777174B (en)	1978-08-30

Publication	Publication Date	Title
US3920664A (en)	1975-11-18	D-2-halo-6-alkyl-8-substituted ergolines and related compounds
US4348391A (en)	1982-09-07	Sulfonamido and sulfamoylamino-ergoline-I derivatives
US4649200A (en)	1987-03-10	Substituted pyrroles with opioid receptor activity
US3922347A (en)	1975-11-25	Method of inhibiting prolactin secretion with 8-acylaminoergolenes
EP0070562B1 (fr)	1985-06-12	Dérivés d'ergoline, leur procédé de préparation et compositions pharmaceutiques les contenant
EP0125607A2 (fr)	1984-11-21	Dérivés de pyrido (1,5) benzodiazépinones à activité pharmacologique
US4180581A (en)	1979-12-25	N-9,10-dihydrolysergyl-m-aminobenzoic acid amide derivative
Johnson et al.	1973	Emetic activity of reduced lysergamides
HU192052B (en)	1987-05-28	Process for preparing new beta-carboline derivatives and pharmaceutical compositions containing them
CA1064918A (fr)	1979-10-23	Les 6-methylergolines disubstituees en 8,8 et composes semblables
US3238211A (en)	1966-03-01	Derhvatives of g-methyl and i,g-dimethyl ergolhne
CS207489B2 (en)	1981-07-31	Method of making new ergoline derivates
US3814765A (en)	1974-06-04	8,9-didehydro-10-alkoxy-ergolenes and process of preparation thereof
US3646046A (en)	1972-02-29	1 6-dimethyl-10alpha-ergoline derivatives
CA1062253A (fr)	1979-09-11	Methode pour la preparation des 6-methyl-8-(substituant) methylergolines
US4299836A (en)	1981-11-10	Novel ergol-8-ene and ergolin compounds and process for preparing same
IL42730A (en)	1976-06-30	D-6-methyl-2,8-disubstituted ergolines,their preparation and pharmaceutical compositions containing them
CA1142176B (fr)	1983-03-01	2-azaergolines et 2-aza-8 (ou 9)-ergolenes
US4176182A (en)	1979-11-27	Sulfamoyl derivatives of 8-β-aminomethylergoline
EP0082712A2 (fr)	1983-06-29	Composés 2-phénylimidazo (2,1-b)benzothiazoliques, leurs sels, procédé pour leur préparation et compositions pharmaceutiques les contenant
CZ129693A3 (en)	1994-01-19	Novel thienothiazine derivatives, process of their preparation and pharmaceutical preparations in which they are comprised
AU631228B2 (en)	1992-11-19	Pyrido (2,3-g) quinolines
US3968112A (en)	1976-07-06	Synthesis of penniclavine and elymoclavine
US4001242A (en)	1977-01-04	D-6-methyl-8-formyl-10α-alkoxy-8-ergolene
US3684805A (en)	1972-08-15	2,3,4,4a-TETRAHYDRO-10H-1,2-OXAZINO {8 3,2-b{9 (1,3)BENZOXAZIN-10-ONES