NO128995B - - Google Patents

Download PDF

Info

Publication number: NO128995B
Authority: NO; Norway
Prior art keywords: acid; solution; general formula; compound; methyl
Prior art date: 1969-06-20

Application number

NO02386/70A

Other languages

English (en)

Norwegian (no)

Inventor

S Guttmann

Original Assignee

Sandoz Ag

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.)

1969-06-20

Filing date

1970-06-19

Publication date

1974-02-11

1970-06-19 Application filed by Sandoz Ag filed Critical Sandoz Ag

1974-02-11 Publication of NO128995B publication Critical patent/NO128995B/no

Links

150000001875 compounds Chemical class 0.000 claims description 38
239000002253 acid Substances 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
-1 (2R Chemical class 0.000 claims description 9
ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
239000011877 solvent mixture Substances 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
ZAGRKAFMISFKIO-IINYFYTJSA-N (6ar,9s)-7-methyl-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=CNC3=C1 ZAGRKAFMISFKIO-IINYFYTJSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
WGZBEDCLEXJQGW-XHDPSFHLSA-N (6aR,9S)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound CN1C=C2C[C@H]3N(C[C@@H](C(O)=O)C=C3C=3C=CC=C1C32)C WGZBEDCLEXJQGW-XHDPSFHLSA-N 0.000 claims description 2
WGZBEDCLEXJQGW-IAQYHMDHSA-N (6ar,9r)-4,7-dimethyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CN(C)C3=C1 WGZBEDCLEXJQGW-IAQYHMDHSA-N 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
239000000243 solution Substances 0.000 description 58
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 22
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 10
239000012071 phase Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
102000003946 Prolactin Human genes 0.000 description 8
108010057464 Prolactin Proteins 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
229940097325 prolactin Drugs 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
150000008064 anhydrides Chemical class 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000011734 sodium Substances 0.000 description 6
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 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
239000002585 base Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
UJYGDMFEEDNVBF-UHFFFAOYSA-N ergocornin Chemical compound C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 description 4
150000007530 organic bases Chemical group 0.000 description 4
239000000047 product Substances 0.000 description 4
230000028327 secretion Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical class IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IVIUCVPWPODFER-UHFFFAOYSA-N 2-ethoxycarbonyl-3-methyl-2-phenylmethoxybutanoic acid Chemical compound CCOC(=O)C(C(O)=O)(C(C)C)OCC1=CC=CC=C1 IVIUCVPWPODFER-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
LRMLTYOJCFBKLZ-UHFFFAOYSA-N diethyl 2-phenylmethoxy-2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)(C(C)C)OCC1=CC=CC=C1 LRMLTYOJCFBKLZ-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
230000011987 methylation Effects 0.000 description 2
238000007069 methylation reaction Methods 0.000 description 2
229960003908 pseudoephedrine Drugs 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
JXGVXCZADZNAMJ-NSHDSACASA-N (2s)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 JXGVXCZADZNAMJ-NSHDSACASA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000124224 Claviceps paspali Species 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
HWBLTYHIEYOAOL-UHFFFAOYSA-N Diisopropyl sulfate Chemical compound CC(C)OS(=O)(=O)OC(C)C HWBLTYHIEYOAOL-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
208000037273 Pathologic Processes Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002908 adrenolytic effect Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
YNLVMCVYVLXNGG-UHFFFAOYSA-N diethyl 2-phenylmethoxypropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)OCC1=CC=CC=C1 YNLVMCVYVLXNGG-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000001294 luteotrophic effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
VXGRMCZTYDXKQW-YFKPBYRVSA-N methyl (2s)-2-aminopentanoate Chemical compound CCC[C@H](N)C(=O)OC VXGRMCZTYDXKQW-YFKPBYRVSA-N 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000009054 pathological process Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO02386/70A 1969-06-20 1970-06-19 NO128995B (ko)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH946269A CH517099A (de)	1969-06-20	1969-06-20	Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide

Publications (1)

Publication Number	Publication Date
NO128995B true NO128995B (ko)	1974-02-11

Family

ID=4352231

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO02386/70A NO128995B (ko)	1969-06-20	1970-06-19

Country Status (18)

Country	Link
US (1)	US3681355A (ko)
AT (1)	AT317447B (ko)
BE (1)	BE752197A (ko)
CA (1)	CA947292A (ko)
CH (1)	CH517099A (ko)
CS (1)	CS163213B2 (ko)
DE (1)	DE2029447A1 (ko)
DK (1)	DK129454B (ko)
ES (2)	ES380883A1 (ko)
FR (1)	FR2052994B1 (ko)
GB (1)	GB1309283A (ko)
HU (1)	HU162311B (ko)
IL (1)	IL34747A (ko)
NL (1)	NL7008409A (ko)
NO (1)	NO128995B (ko)
PL (1)	PL83620B1 (ko)
SU (1)	SU417944A3 (ko)
ZA (1)	ZA704193B (ko)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3846433A (en) *	1969-05-06	1974-11-05	Sandoz Ltd	Process for preparing ergot alkaloids
EP2515654A4 (en) *	2009-12-23	2013-04-24	Map Pharmaceuticals Inc	NEW ERGOLINANALOGA
MX2013015373A (es)	2011-06-23	2014-02-11	Map Pharmaceuticals Inc	Nuevos analogos de fluoroergolina.
WO2013095707A1 (en)	2011-12-19	2013-06-27	Map Pharmaceuticals, Inc.	Novel iso-ergoline derivatives
SG11201403433PA (en)	2011-12-21	2014-07-30	Map Pharmaceuticals Inc	Novel neuromodulatory compounds
US9012640B2 (en)	2012-06-22	2015-04-21	Map Pharmaceuticals, Inc.	Cabergoline derivatives

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2997470A (en) *	1956-03-05	1961-08-22	Lilly Co Eli	Lysergic acid amides
CH344731A (de) *	1956-05-18	1960-02-29	Sandoz Ag	Verfahren zur Herstellung von neuen, am Indolstickstoff alkylierten Derivaten der Lysergsäure-Reihe
GB1011112A (en) *	1961-05-10	1965-11-24	Sandoz Ag	Improvements in or relating to ergot alkaloids
CH469006A (de) *	1965-07-07	1969-02-28	Sandoz Ag	Verfahren zur Herstellung neuer synthetischer Alkaloide
CH469735A (de) *	1965-11-02	1969-03-15	Sandoz Ag	Verfahren zur Herstellung heterocyclischer Verbindungen
FR1583797A (ko) *	1967-04-12	1969-12-05

1969
- 1969-06-20 CH CH946269A patent/CH517099A/de not_active IP Right Cessation
1970
- 1970-06-05 GB GB2714370A patent/GB1309283A/en not_active Expired
- 1970-06-10 NL NL7008409A patent/NL7008409A/xx unknown
- 1970-06-15 US US46480A patent/US3681355A/en not_active Expired - Lifetime
- 1970-06-15 DE DE19702029447 patent/DE2029447A1/de active Pending
- 1970-06-17 SU SU1451383A patent/SU417944A3/ru active
- 1970-06-18 BE BE752197D patent/BE752197A/xx unknown
- 1970-06-18 FR FR7022467A patent/FR2052994B1/fr not_active Expired
- 1970-06-18 CA CA85861A patent/CA947292A/en not_active Expired
- 1970-06-18 ES ES380883A patent/ES380883A1/es not_active Expired
- 1970-06-18 IL IL34747A patent/IL34747A/en unknown
- 1970-06-19 DK DK317370AA patent/DK129454B/da unknown
- 1970-06-19 ZA ZA704193A patent/ZA704193B/xx unknown
- 1970-06-19 CS CS4317A patent/CS163213B2/cs unknown
- 1970-06-19 PL PL1970141454A patent/PL83620B1/pl unknown
- 1970-06-19 NO NO02386/70A patent/NO128995B/no unknown
- 1970-06-19 HU HUSA2105A patent/HU162311B/hu unknown
- 1970-06-19 AT AT554170A patent/AT317447B/de not_active IP Right Cessation
1971
- 1971-01-28 ES ES387714A patent/ES387714A1/es not_active Expired

Also Published As

Publication number	Publication date
DK129454B (da)	1974-10-14
US3681355A (en)	1972-08-01
ZA704193B (en)	1972-01-26
GB1309283A (en)	1973-03-07
IL34747A (en)	1973-07-30
NL7008409A (ko)	1970-12-22
DK129454C (ko)	1975-03-03
SU417944A3 (ru)	1974-02-28
CS163213B2 (ko)	1975-08-29
ES387714A1 (es)	1974-01-01
CA947292A (en)	1974-05-14
PL83620B1 (ko)	1975-12-31
HU162311B (ko)	1973-01-29
IL34747A0 (en)	1970-08-19
BE752197A (fr)	1970-12-18
DE2029447A1 (de)	1971-01-07
AT317447B (de)	1974-08-26
ES380883A1 (es)	1973-04-01
FR2052994B1 (ko)	1974-05-24
CH517099A (de)	1971-12-31
FR2052994A1 (ko)	1971-04-16

Publication	Publication Date	Title
US4031098A (en)	1977-06-21	Camptothecin analogues
JPS582946B2 (ja)	1983-01-19	８− チオメチルエルゴリンルイノセイホウ
RU2387656C2 (ru)	2010-04-27	Способ получения гидробромида галантамина
NO128995B (ko)	1974-02-11
FI59254C (fi)	1981-07-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara ergopeptinderivat
NO128533B (ko)	1973-12-03
IL32462A (en)	1973-07-30	N-substituted lysergamide derivatives
CS208164B2 (en)	1981-08-31	Method of making the d-2-halogene-6-methyl-8-kyan/carboxamido/methylergolines
US3190884A (en)	1965-06-22	Chz-chz-cn
US3583991A (en)	1971-06-08	6-methyl-8-piperazinyl-methylergalene (ergoline) derivatives
US3772299A (en)	1973-11-13	P'-alkoxy-ergotamines
FI68841C (fi)	1985-11-11	Foerfarande foer framstaellning av terapeutiskt anvaendbara erotpeptidalkaloidderivat
US3592816A (en)	1971-07-13	N-substituted piperazides of lysergic acid
NO138850B (no)	1978-08-14	Analogifremgangsmaater for fremstilling av nye terapeutisk aktive derivater av ditiino(1,4)(2,3-c)pyrrol
NO139441B (no)	1978-12-04	Fremgangsmaate ved fremstilling av nye leurosinderivater og deres salter
KR800000558B1 (ko)	1980-06-23	6-메틸-8-(치환) 메틸에르골린류의 제조방법
KR800000413B1 (ko)	1980-05-20	6-메틸-8-(치환)메틸 에르골린류의 제조방법
NO132478B (ko)	1975-08-11
SU420175A3 (ko)	1974-03-15
Labriola et al.	1951	Studies in argentine plants. XI. The partial structure of erysovine, erysodine, and erysopine
US3232943A (en)	1966-02-01	Cyanoethyl ergolene and ergoline derivatives
SAIGA et al.	1987	Synthesis of 1, 2, 3, 4-Tetrahydro-β-carboline Derivatives as Hepatoprotective Agents. II. Alkyl 1, 2, 3, 4-Tetrahydro-β-carboline-2-carbodithioates
KR800000414B1 (ko)	1980-05-20	6-메티-8-(치환)메틸에르골린류의 제조방법
US4596830A (en)	1986-06-24	Novel derivatives of 2-(2-thienyl)-imidazo[4,5-b]-pyridines and their pharmaceutically acceptable salts
CS236782B2 (en)	1985-05-15	Processing of 5 s-(2r-butyl)peptidergotalkaloid