NO751210L - - Google Patents

Info

Publication number: NO751210L
Authority: NO; Norway
Prior art keywords: formula; methyl; lower alkyl; optionally; acid addition
Prior art date: 1974-04-16

Application number

NO751210*[A

Other languages

English (en)

Norwegian (no)

Inventor

H Hauth

H Tascherter

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.)

1974-04-16

Filing date

1975-10-08

Publication date

1975-10-17

1975-10-08 Application filed by Sandoz Ag filed Critical Sandoz Ag

1975-10-17 Publication of NO751210L publication Critical patent/NO751210L/no

Links

150000001875 compounds Chemical class 0.000 claims description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
-1 phenoxy, hydroxy Chemical group 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000002391 heterocyclic compounds Chemical class 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 3
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
102000003946 Prolactin Human genes 0.000 description 13
108010057464 Prolactin Proteins 0.000 description 13
229940097325 prolactin Drugs 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
WZWHHCYTJDBJPY-TZMCWYRMSA-N (6ar,10ar)-7-methyl-4,6,6a,8,10,10a-hexahydroindolo[4,3-fg]quinoline-9-one Chemical compound C1=CC([C@H]2CC(=O)CN([C@@H]2C2)C)=C3C2=CNC3=C1 WZWHHCYTJDBJPY-TZMCWYRMSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
238000007792 addition Methods 0.000 description 9
229910052763 palladium Inorganic materials 0.000 description 9
241000700159 Rattus Species 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
230000028327 secretion Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
238000010828 elution Methods 0.000 description 4
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
YTFYAKJCTLIUKC-GERZZCHPSA-N (6ar,10ar)-7-methyl-n-pyridin-3-yl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-amine Chemical compound CN([C@H]1[C@@H](C=2C=CC=C3NC=C(C=23)C1)C1)CC1NC1=CC=CN=C1 YTFYAKJCTLIUKC-GERZZCHPSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
150000001540 azides Chemical class 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
229940095064 tartrate Drugs 0.000 description 3
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 description 3
238000012360 testing method Methods 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000001358 L(+)-tartaric acid Substances 0.000 description 2
235000011002 L(+)-tartaric acid Nutrition 0.000 description 2
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 2
239000002262 Schiff base Substances 0.000 description 2
150000004753 Schiff bases Chemical class 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
238000010171 animal model Methods 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
208000017169 kidney disease Diseases 0.000 description 2
230000006651 lactation Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
VGOXYEVIOFBLQY-ZFJSRUIDSA-N (6aR,9R,10aR)-7-methyl-N-(6-phenoxypyridin-3-yl)-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-amine Chemical compound CN1C[C@@H](C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C=34)NC=1C=CC(=NC=1)OC1=CC=CC=C1 VGOXYEVIOFBLQY-ZFJSRUIDSA-N 0.000 description 1
LAASAAVOUUBUBD-SZVBFZGTSA-N (6aR,9R,10aR)-N-(6-methoxypyridin-3-yl)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-amine Chemical compound CN1C[C@@H](C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C=34)NC=1C=CC(=NC=1)OC LAASAAVOUUBUBD-SZVBFZGTSA-N 0.000 description 1
HAFWELDDNUXLCK-ODZAUARKSA-N (z)-but-2-enedioic acid;hydrate Chemical compound O.OC(=O)\C=C/C(O)=O HAFWELDDNUXLCK-ODZAUARKSA-N 0.000 description 1
VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-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
HRLHJWKMOMDDND-UHFFFAOYSA-N 6-[(2-methylpropan-2-yl)oxy]pyridin-3-amine Chemical compound CC(C)(C)OC1=CC=C(N)C=N1 HRLHJWKMOMDDND-UHFFFAOYSA-N 0.000 description 1
DAFKCYYRSZSMAJ-UHFFFAOYSA-N 6-butoxypyridin-3-amine Chemical compound CCCCOC1=CC=C(N)C=N1 DAFKCYYRSZSMAJ-UHFFFAOYSA-N 0.000 description 1
UXIPFCIFZLFXNC-UHFFFAOYSA-N 6-ethoxypyridin-3-amine Chemical compound CCOC1=CC=C(N)C=N1 UXIPFCIFZLFXNC-UHFFFAOYSA-N 0.000 description 1
UUVDJIWRSIJEBS-UHFFFAOYSA-N 6-methoxypyridin-3-amine Chemical compound COC1=CC=C(N)C=N1 UUVDJIWRSIJEBS-UHFFFAOYSA-N 0.000 description 1
DETKIRMPBJPJRQ-UHFFFAOYSA-N 6-phenoxypyridin-3-amine Chemical compound N1=CC(N)=CC=C1OC1=CC=CC=C1 DETKIRMPBJPJRQ-UHFFFAOYSA-N 0.000 description 1
ZHOGVKFSKSGQRC-UHFFFAOYSA-N 6-propan-2-yloxypyridin-3-amine Chemical compound CC(C)OC1=CC=C(N)C=N1 ZHOGVKFSKSGQRC-UHFFFAOYSA-N 0.000 description 1
ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000009132 Catalepsy Diseases 0.000 description 1
VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 1
206010017600 Galactorrhoea Diseases 0.000 description 1
206010020852 Hypertonia Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
206010036618 Premenstrual syndrome Diseases 0.000 description 1
206010047853 Waxy flexibility Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
201000008275 breast carcinoma Diseases 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
230000004992 fission Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000005984 hydrogenation reaction 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
201000006370 kidney failure Diseases 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
150000007522 mineralic acids Chemical group 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
230000001817 pituitary effect Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000010998 test method Methods 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
238000011282 treatment Methods 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000010626 work up procedure 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
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- 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
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms

Landscapes

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

NO751210*[A 1974-04-16 1975-10-08 NO751210L (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH523274		1974-04-16
CH189375		1975-02-14
CH189475		1975-02-14

Publications (1)

Publication Number	Publication Date
NO751210L true NO751210L (ja)	1975-10-17

Family

ID=27173325

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO751210*[A NO751210L (ja)	1974-04-16	1975-10-08

Country Status (12)

Country	Link
JP (1)	JPS50137998A (ja)
AU (1)	AU8011475A (ja)
DD (1)	DD121638A5 (ja)
DE (1)	DE2515100A1 (ja)
DK (1)	DK147775A (ja)
ES (1)	ES436569A1 (ja)
FI (1)	FI751031A7 (ja)
FR (1)	FR2267781A1 (ja)
IL (1)	IL47085A0 (ja)
NL (1)	NL7504330A (ja)
NO (1)	NO751210L (ja)
SE (1)	SE7504036L (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1573621A (en) *	1976-01-02	1980-08-28	Sandoz Ltd	Acylated 6-methyl-8a-amino-ergoline i compounds
JPS5448880A (en) *	1977-09-02	1979-04-17	Tetra Pak Int	Method of designing packaging laminate and packaging laminate
DE3227122A1 (de) *	1982-07-20	1984-01-26	Dr. Rentschler Arzneimittel Gmbh & Co, 7958 Laupheim	Stabile loesungen von mutterkornalkaloiden

1975
- 1975-04-07 DE DE19752515100 patent/DE2515100A1/de active Pending
- 1975-04-07 FI FI751031A patent/FI751031A7/fi not_active Application Discontinuation
- 1975-04-07 DK DK147775A patent/DK147775A/da not_active IP Right Cessation
- 1975-04-08 SE SE7504036A patent/SE7504036L/xx unknown
- 1975-04-11 NL NL7504330A patent/NL7504330A/xx unknown
- 1975-04-14 ES ES436569A patent/ES436569A1/es not_active Expired
- 1975-04-14 AU AU80114/75A patent/AU8011475A/en not_active Expired
- 1975-04-14 IL IL47085A patent/IL47085A0/xx unknown
- 1975-04-15 DD DD185464A patent/DD121638A5/xx unknown
- 1975-04-15 JP JP50044910A patent/JPS50137998A/ja active Pending
- 1975-04-16 FR FR7511771A patent/FR2267781A1/fr active Granted
- 1975-10-08 NO NO751210*[A patent/NO751210L/no unknown

Also Published As

Publication number	Publication date
FR2267781B1 (ja)	1978-08-04
DE2515100A1 (de)	1975-11-06
FI751031A7 (ja)	1975-10-17
ES436569A1 (es)	1977-04-01
AU8011475A (en)	1976-10-21
FR2267781A1 (en)	1975-11-14
NL7504330A (nl)	1975-10-20
DK147775A (ja)	1975-10-17
SE7504036L (sv)	1975-10-17
DD121638A5 (ja)	1976-08-12
JPS50137998A (ja)	1975-11-01
IL47085A0 (en)	1975-08-31

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