NO750748L - - Google Patents

Info

Publication number: NO750748L
Authority: NO; Norway
Prior art keywords: formula; compound; compounds; methyl; stands
Prior art date: 1974-03-14

Application number

NO75750748A

Other languages

English (en)

Norwegian (no)

Inventor

P Stuetz

P Stadler

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.)

1974-03-14

Filing date

1975-03-06

Publication date

1975-09-16

1974-03-14 Priority claimed from CH356374A external-priority patent/CH593972A5/xx

1975-03-06 Application filed by Sandoz Ag filed Critical Sandoz Ag

1975-09-16 Publication of NO750748L publication Critical patent/NO750748L/no

Links

150000001875 compounds Chemical class 0.000 claims description 54
238000000034 method Methods 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000000623 heterocyclic group Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
239000002585 base Substances 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims 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 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Substances 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000002571 phosphodiesterase inhibitor Substances 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 12
-1 heterocyclic radical Chemical class 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000000825 pharmaceutical preparation Substances 0.000 description 6
239000000126 substance Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000003291 dopaminomimetic effect Effects 0.000 description 4
230000004936 stimulating effect Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229960001948 caffeine Drugs 0.000 description 3
VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 3
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
208000009132 Catalepsy Diseases 0.000 description 2
206010008120 Cerebral ischaemia Diseases 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
208000018737 Parkinson disease Diseases 0.000 description 2
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
206010047853 Waxy flexibility Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
150000002391 heterocyclic compounds Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
230000003285 pharmacodynamic effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
229960003147 reserpine Drugs 0.000 description 2
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
229960000278 theophylline Drugs 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
YNZFUWZUGRBMHL-UHFFFAOYSA-N 2-[4-[3-(11-benzo[b][1]benzazepinyl)propyl]-1-piperazinyl]ethanol Chemical compound C1CN(CCO)CCN1CCCN1C2=CC=CC=C2C=CC2=CC=CC=C21 YNZFUWZUGRBMHL-UHFFFAOYSA-N 0.000 description 1
DFBTUSRLMAAUHX-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)methyl]imidazolidin-2-one Chemical class C1=C(OC)C(OC)=CC=C1CC1NC(=O)NC1 DFBTUSRLMAAUHX-UHFFFAOYSA-N 0.000 description 1
PDMUULPVBYQBBK-UHFFFAOYSA-N 4-[(3-butoxy-4-methoxyphenyl)methyl]-2-imidazolidinone Chemical compound C1=C(OC)C(OCCCC)=CC(CC2NC(=O)NC2)=C1 PDMUULPVBYQBBK-UHFFFAOYSA-N 0.000 description 1
ULBZRLXAMNKBPM-UHFFFAOYSA-N 4-amino-1h-pyrazolo[3,4-b]pyridine-5-carboxylic acid Chemical class NC1=C(C(O)=O)C=NC2=C1C=NN2 ULBZRLXAMNKBPM-UHFFFAOYSA-N 0.000 description 1
BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical compound C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-UHFFFAOYSA-N 0.000 description 1
PFWLFWPASULGAN-UHFFFAOYSA-N 7-methylxanthine Chemical compound N1C(=O)NC(=O)C2=C1N=CN2C PFWLFWPASULGAN-UHFFFAOYSA-N 0.000 description 1
RTAPDZBZLSXHQQ-UHFFFAOYSA-N 8-methyl-3,7-dihydropurine-2,6-dione Chemical class N1C(=O)NC(=O)C2=C1N=C(C)N2 RTAPDZBZLSXHQQ-UHFFFAOYSA-N 0.000 description 1
229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical class [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
229940123445 Tricyclic antidepressant Drugs 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
229940005482 dopamine injection Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
229960001789 papaverine Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000002990 phenothiazines Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
210000003523 substantia nigra Anatomy 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
239000003029 tricyclic antidepressant agent Substances 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
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Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
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NO75750748A 1974-03-14 1975-03-06 NO750748L (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH356374A CH593972A5 (fr)	1974-03-14	1974-03-14
CH1013874		1974-07-23

Publications (1)

Publication Number	Publication Date
NO750748L true NO750748L (fr)	1975-09-16

Family

ID=25693324

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO75750748A NO750748L (fr)	1974-03-14	1975-03-06

Country Status (18)

Country	Link
JP (1)	JPS589111B2 (fr)
AU (1)	AU500890B2 (fr)
CA (1)	CA1071192A (fr)
DD (1)	DD118428A5 (fr)
DE (1)	DE2509471A1 (fr)
DK (1)	DK141701B (fr)
ES (1)	ES435538A1 (fr)
FI (1)	FI60865C (fr)
FR (1)	FR2263774B1 (fr)
GB (1)	GB1497681A (fr)
HK (1)	HK8481A (fr)
IE (1)	IE41533B1 (fr)
IL (1)	IL46809A (fr)
MY (1)	MY8100331A (fr)
NL (1)	NL7502807A (fr)
NO (1)	NO750748L (fr)
PH (1)	PH12966A (fr)
SE (1)	SE420094B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4147789A (en) *	1974-03-14	1979-04-03	Sandoz Ltd.	6-Methyl-8-thiomethyl-ergolene derivatives
JPS5293797A (en) *	1976-01-30	1977-08-06	Sandoz Ag	Improvement in organic compound
GB1555751A (en) *	1977-02-02	1979-11-14	Farmaceutici Italia	Ergoline deritatives
US4166182A (en) *	1978-02-08	1979-08-28	Eli Lilly And Company	6-n-propyl-8-methoxymethyl or methylmercaptomethylergolines and related compounds
US4382940A (en) *	1979-12-06	1983-05-10	Farmitalia Carlo Erba S.P.A.	Ercoline derivatives and therapeutic compositions having CNS affecting activity
GB2120242A (en) *	1982-04-30	1983-11-30	Erba Farmitalia	Ergoline derivatives
CH649998A5 (de) *	1982-08-09	1985-06-28	Sandoz Ag	Ergolinderivate, ein verfahren zu ihrer herstellung und heilmittel, enthaltend diese ergolinderivate als wirkstoff.
IT1215261B (it) *	1985-04-05	1990-01-31	Poli Ind Chimica Spa	Composizioni farmaceutiche adattivita' antigalattopoietica.
US4798834A (en) *	1987-08-31	1989-01-17	Eli Lilly And Company	Optionally substituted (3β-9,10-didehydro-2,3-dihydro ergoline as serotonergic function enhancement

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6818658A (fr) *	1968-01-18	1969-07-22

1975
- 1975-02-12 IE IE542/75A patent/IE41533B1/en unknown
- 1975-03-05 DE DE19752509471 patent/DE2509471A1/de not_active Ceased
- 1975-03-05 DK DK89375AA patent/DK141701B/da not_active IP Right Cessation
- 1975-03-05 SE SE7502469A patent/SE420094B/xx unknown
- 1975-03-06 NO NO75750748A patent/NO750748L/no unknown
- 1975-03-06 FI FI750644A patent/FI60865C/fi not_active IP Right Cessation
- 1975-03-10 NL NL7502807A patent/NL7502807A/xx not_active Application Discontinuation
- 1975-03-10 GB GB9807/75A patent/GB1497681A/en not_active Expired
- 1975-03-11 FR FR7507472A patent/FR2263774B1/fr not_active Expired
- 1975-03-12 ES ES435538A patent/ES435538A1/es not_active Expired
- 1975-03-12 DD DD184721A patent/DD118428A5/xx unknown
- 1975-03-12 PH PH16903A patent/PH12966A/en unknown
- 1975-03-12 IL IL46809A patent/IL46809A/xx unknown
- 1975-03-13 AU AU79057/75A patent/AU500890B2/en not_active Ceased
- 1975-03-13 CA CA221,971A patent/CA1071192A/fr not_active Expired
- 1975-03-13 JP JP50029600A patent/JPS589111B2/ja not_active Expired
1981
- 1981-03-12 HK HK84/81A patent/HK8481A/xx unknown
- 1981-12-30 MY MY331/81A patent/MY8100331A/xx unknown

Also Published As

Publication number	Publication date
DK89375A (fr)	1975-09-15
DK141701C (fr)	1980-10-20
FR2263774A1 (fr)	1975-10-10
SE420094B (sv)	1981-09-14
DE2509471A1 (de)	1975-09-18
FI60865B (fi)	1981-12-31
IE41533L (en)	1975-09-14
CA1071192A (fr)	1980-02-05
JPS589111B2 (ja)	1983-02-18
FR2263774B1 (fr)	1978-08-04
DK141701B (da)	1980-05-27
MY8100331A (en)	1981-12-31
SE7502469L (fr)	1975-09-15
IE41533B1 (en)	1980-01-30
GB1497681A (en)	1978-01-12
IL46809A (en)	1978-04-30
ES435538A1 (es)	1977-03-16
NL7502807A (nl)	1975-09-16
DD118428A5 (fr)	1976-03-05
PH12966A (en)	1979-10-19
AU500890B2 (en)	1979-06-07
HK8481A (en)	1981-03-20
FI60865C (fi)	1982-04-13
FI750644A7 (fr)	1975-09-15
JPS50123698A (fr)	1975-09-29
IL46809A0 (en)	1975-07-28
AU7905775A (en)	1976-09-16

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US4147789A (en)	1979-04-03	6-Methyl-8-thiomethyl-ergolene derivatives
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DE69413112T2 (de)	1999-05-12	5-HT3 Pyrrolopyrazinderivate
NO158422B (no)	1988-05-30	Analogifremgangsmaate ved fremstilling av nye oksadiazolopyrimidin-derivater.
KR790000927B1 (ko)	1979-07-31	복소환 화합물의 제조방법
TW202317577A (zh)	2023-05-01	新穎化合物
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