NO774133L - Ergolinderivater og fremgangsmaate til fremstilling derav - Google Patents
Ergolinderivater og fremgangsmaate til fremstilling deravInfo
- Publication number
- NO774133L NO774133L NO774133A NO774133A NO774133L NO 774133 L NO774133 L NO 774133L NO 774133 A NO774133 A NO 774133A NO 774133 A NO774133 A NO 774133A NO 774133 L NO774133 L NO 774133L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- methylergoline
- carbon atoms
- ergoline
- general formula
- Prior art date
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 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 title claims description 8
- 238000000034 method Methods 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- QRCPTNOHWBJXPI-PUGIBVIZSA-N 1-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-piperidin-1-ylethanone Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3NC=C(C=23)C1)C1)CC1C(=O)CN1CCCCC1 QRCPTNOHWBJXPI-PUGIBVIZSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- IFNTVCLRZCQLIA-RMNMTYGKSA-N CN1CC(C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)C(COC(C3=CN=CC(=C3)Br)=O)=O Chemical compound CN1CC(C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)C(COC(C3=CN=CC(=C3)Br)=O)=O IFNTVCLRZCQLIA-RMNMTYGKSA-N 0.000 claims description 2
- SSTSENUGLHSCRE-PUGIBVIZSA-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-dimethoxybenzoate Chemical compound COC1=C(C(=O)OCC(=O)C2CN([C@@H]3CC4=CNC5=CC=CC([C@H]3C2)=C45)C)C(=CC=C1)OC SSTSENUGLHSCRE-PUGIBVIZSA-N 0.000 claims description 2
- AIUSMSGJBCMSEV-RJPUVWTNSA-N [2-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-oxoethyl] acetate Chemical compound C1=CC([C@H]2CC(CN([C@@H]2C2)C)C(=O)COC(C)=O)=C3C2=CNC3=C1 AIUSMSGJBCMSEV-RJPUVWTNSA-N 0.000 claims description 2
- MYCDAPGRFOPWAO-PUGIBVIZSA-N [2-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-oxoethyl] hexanoate Chemical compound C1=CC([C@H]2CC(CN(C)[C@@H]2C2)C(=O)COC(=O)CCCCC)=C3C2=CNC3=C1 MYCDAPGRFOPWAO-PUGIBVIZSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 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 claims 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims 1
- WNHISOLLRJYEDH-AIEAQGLASA-N CN([C@H]1[C@@H](C=2C=CC=C3N(C)C=C(C=23)C1)C1)CC1C(=O)COC(=O)C1=CN=CC(Br)=C1 Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3N(C)C=C(C=23)C1)C1)CC1C(=O)COC(=O)C1=CN=CC(Br)=C1 WNHISOLLRJYEDH-AIEAQGLASA-N 0.000 claims 1
- CQGHQZOMAPJKJF-NBSGVIAVSA-N [2-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-oxoethyl] 2,2-dimethylpropanoate Chemical compound C1=CC([C@H]2CC(CN([C@@H]2C2)C)C(=O)COC(=O)C(C)(C)C)=C3C2=CNC3=C1 CQGHQZOMAPJKJF-NBSGVIAVSA-N 0.000 claims 1
- YUYSWVQUVIRDHU-FIALGKLESA-N [2-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-oxoethyl] benzoate Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3NC=C(C=23)C1)C1)CC1C(=O)COC(=O)C1=CC=CC=C1 YUYSWVQUVIRDHU-FIALGKLESA-N 0.000 claims 1
- SMMWMBAPJOZWQS-PUGIBVIZSA-N [2-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-oxoethyl] pyridine-3-carboxylate Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3NC=C(C=23)C1)C1)CC1C(=O)COC(=O)C1=CC=CN=C1 SMMWMBAPJOZWQS-PUGIBVIZSA-N 0.000 claims 1
- VJFSQTCAGAIWJP-PUGIBVIZSA-N [2-[(6ar,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2-oxoethyl] pyridine-4-carboxylate Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3NC=C(C=23)C1)C1)CC1C(=O)COC(=O)C1=CC=NC=C1 VJFSQTCAGAIWJP-PUGIBVIZSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000008018 melting Effects 0.000 description 20
- 238000002844 melting Methods 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 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 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 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
- 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 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 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
- -1 hydroxy, nitro, amino Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 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 2
- TZLSHEXDQCEPPG-YZCZPWFXSA-N 1-[(6ar,10as)-10a-methoxy-7-methyl-4,6,6a,8,9,10-hexahydroindolo[4,3-fg]quinoline-9-yl]-2-bromoethanone Chemical compound C1=CC([C@]2(OC)[C@H](N(C)CC(C2)C(=O)CBr)C2)=C3C2=CNC3=C1 TZLSHEXDQCEPPG-YZCZPWFXSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 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
- 230000000095 emetic effect Effects 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 230000035935 pregnancy Effects 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 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
- ZOFRHEKPCMMKHR-XGENFCTJSA-N 1-[(6ar,10as)-10a-methoxy-4,7-dimethyl-6a,8,9,10-tetrahydro-6h-indolo[4,3-fg]quinoline-9-yl]-2-bromoethanone Chemical compound C1=CC([C@]2(OC)[C@H](N(C)CC(C2)C(=O)CBr)C2)=C3C2=CN(C)C3=C1 ZOFRHEKPCMMKHR-XGENFCTJSA-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
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 206010000599 Acromegaly Diseases 0.000 description 1
- YCBRZHMOSVKVLE-CTDNXKOOSA-N CO[C@@]12C=3C=CC=C4NC=C(C[C@H]1N(CC(C2)C(COC(C2=CN=CC(=C2)Br)=O)=O)C)C34 Chemical compound CO[C@@]12C=3C=CC=C4NC=C(C[C@H]1N(CC(C2)C(COC(C2=CN=CC(=C2)Br)=O)=O)C)C34 YCBRZHMOSVKVLE-CTDNXKOOSA-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
- 239000004280 Sodium formate Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000085 anti-nidation effect Effects 0.000 description 1
- 230000009286 beneficial 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
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 208000031424 hyperprolactinemia Diseases 0.000 description 1
- 239000000960 hypophysis hormone Substances 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 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
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 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
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 229940103091 potassium benzoate Drugs 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 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
- 239000007858 starting material Substances 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
- 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)
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 |
|---|---|
| NO774133L true NO774133L (no) | 1978-06-07 |
Family
ID=10457193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO774133A NO774133L (no) | 1976-12-06 | 1977-12-02 | Ergolinderivater og fremgangsmaate til fremstilling derav |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4196288A (xx) |
| JP (1) | JPS5371099A (xx) |
| AT (1) | AT361138B (xx) |
| AU (1) | AU3111277A (xx) |
| BE (1) | BE861480A (xx) |
| CA (1) | CA1101848A (xx) |
| CS (1) | CS207489B2 (xx) |
| DE (1) | DE2754028A1 (xx) |
| DK (1) | DK535777A (xx) |
| FR (1) | FR2372834A1 (xx) |
| GB (1) | GB1580448A (xx) |
| HU (1) | HU177143B (xx) |
| NL (1) | NL7713226A (xx) |
| NO (1) | NO774133L (xx) |
| NZ (1) | NZ185837A (xx) |
| SE (1) | SE7713720L (xx) |
| SU (1) | SU736872A3 (xx) |
| YU (1) | YU283177A (xx) |
| ZA (1) | ZA777174B (xx) |
Families Citing this family (2)
| 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 |
-
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 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
- 1977-12-01 AU AU31112/77A patent/AU3111277A/en active Pending
- 1977-12-02 DK DK535777A patent/DK535777A/da unknown
- 1977-12-02 CA CA292,311A patent/CA1101848A/en not_active Expired
- 1977-12-02 NO NO774133A patent/NO774133L/no unknown
- 1977-12-02 HU HU77SO1204A patent/HU177143B/hu unknown
- 1977-12-02 ZA ZA00777174A patent/ZA777174B/xx unknown
- 1977-12-02 SE SE7713720A patent/SE7713720L/xx unknown
- 1977-12-02 NZ NZ185837A patent/NZ185837A/xx unknown
- 1977-12-05 DE DE19772754028 patent/DE2754028A1/de not_active Withdrawn
- 1977-12-05 BE BE183147A patent/BE861480A/xx unknown
- 1977-12-05 FR FR7736504A patent/FR2372834A1/fr active Granted
- 1977-12-05 CS CS778087A patent/CS207489B2/cs unknown
- 1977-12-05 SU SU772548999A patent/SU736872A3/ru active
- 1977-12-05 JP JP14599077A patent/JPS5371099A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2372834A1 (fr) | 1978-06-30 |
| FR2372834B1 (xx) | 1981-11-27 |
| HU177143B (en) | 1981-07-28 |
| GB1580448A (en) | 1980-12-03 |
| AT361138B (de) | 1981-02-25 |
| SU736872A3 (ru) | 1980-05-25 |
| SE7713720L (sv) | 1978-06-07 |
| US4196288A (en) | 1980-04-01 |
| NL7713226A (nl) | 1978-06-08 |
| DK535777A (da) | 1978-06-07 |
| ATA860477A (de) | 1980-07-15 |
| CS207489B2 (en) | 1981-07-31 |
| AU3111277A (en) | 1979-06-07 |
| YU283177A (en) | 1983-12-31 |
| DE2754028A1 (de) | 1978-06-08 |
| JPS5371099A (en) | 1978-06-24 |
| ZA777174B (en) | 1978-08-30 |
| NZ185837A (en) | 1979-11-01 |
| BE861480A (fr) | 1978-03-31 |
| CA1101848A (en) | 1981-05-26 |
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