LU86743A1 - Nouvelles 8a-acylamino-ergolines,leur preparation et leur utilisation comme medicaments - Google Patents

Nouvelles 8a-acylamino-ergolines,leur preparation et leur utilisation comme medicaments Download PDF

Info

Publication number: LU86743A1
Authority: LU; Luxembourg
Prior art keywords: group; formula; compound; alkyl; alkyl group
Prior art date: 1986-01-24

Application number

LU86743A

Other languages

English (en)

French (fr)

Original Assignee

Sandoz Sa

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.)

1986-01-24

Filing date

1987-01-22

Publication date

1987-09-03

1987-01-22 Application filed by Sandoz Sa filed Critical Sandoz Sa

1987-09-03 Publication of LU86743A1 publication Critical patent/LU86743A1/fr

Links

239000003814 drug Substances 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 94
238000000034 method Methods 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
101100440695 Dictyostelium discoideum corB gene Proteins 0.000 claims description 14
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 12
-1 COOR5 Chemical group 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
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 12
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
101100533874 Hypocrea jecorina (strain QM6a) sor5 gene Proteins 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 9
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 8
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 8
239000011630 iodine Substances 0.000 claims description 8
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
239000013543 active substance Substances 0.000 claims description 4
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
239000003176 neuroleptic agent Substances 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
239000002841 Lewis acid Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
230000000701 neuroleptic effect Effects 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
ZIIMQMYFQHBXEN-ZBQZNYHESA-N N-[(6aR,9S,10aR)-5-ethynyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound CN1C[C@H](C[C@@H]2C=3C=CC=C4NC(=C(C[C@@H]12)C=34)C#C)NC(C(C)(C)C)=O ZIIMQMYFQHBXEN-ZBQZNYHESA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
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239000000203 mixture Substances 0.000 description 46
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239000000243 solution Substances 0.000 description 29
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238000006243 chemical reaction Methods 0.000 description 15
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
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239000012074 organic phase Substances 0.000 description 11
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238000002425 crystallisation Methods 0.000 description 10
230000008025 crystallization Effects 0.000 description 10
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229910002027 silica gel Inorganic materials 0.000 description 10
229910052938 sodium sulfate Inorganic materials 0.000 description 10
235000011152 sodium sulphate Nutrition 0.000 description 10
238000003756 stirring Methods 0.000 description 10
230000009466 transformation Effects 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
NUVLGIVUSHTJSS-YSVLISHTSA-N CN1C[C@H](C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)NC(C(C)(C)C)=O Chemical compound CN1C[C@H](C[C@@H]2C=3C=CC=C4NC=C(C[C@@H]12)C34)NC(C(C)(C)C)=O NUVLGIVUSHTJSS-YSVLISHTSA-N 0.000 description 9
102000003946 Prolactin Human genes 0.000 description 9
108010057464 Prolactin Proteins 0.000 description 9
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229940097325 prolactin Drugs 0.000 description 9
230000028327 secretion Effects 0.000 description 9
238000007796 conventional method Methods 0.000 description 8
230000000694 effects Effects 0.000 description 7
239000003480 eluent Substances 0.000 description 7
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
JHWDWUPYEQIICX-HRBVQNPCSA-N (6ar,10ar)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-amine Chemical compound C1=CC([C@@H]2[C@H](NCC(C2)N)C2)=C3C2=CNC3=C1 JHWDWUPYEQIICX-HRBVQNPCSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000003136 dopamine receptor stimulating agent Substances 0.000 description 5
235000017550 sodium carbonate Nutrition 0.000 description 5
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239000002904 solvent Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 4
229960004046 apomorphine Drugs 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229940052760 dopamine agonists Drugs 0.000 description 4
239000000284 extract Substances 0.000 description 4
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238000010992 reflux Methods 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
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WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
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241000699670 Mus sp. Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
WNDMNAVMWRQBBQ-WPKBUWHJSA-N N-[(6aR,9S,10aR)-5-formyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]-2,2-dimethylpropanamide Chemical compound C(=O)C1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C WNDMNAVMWRQBBQ-WPKBUWHJSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
206010036832 Prolactinoma Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
206010042008 Stereotypy Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 1
206010047853 Waxy flexibility Diseases 0.000 description 1
206010000210 abortion Diseases 0.000 description 1
231100000176 abortion Toxicity 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
231100000540 amenorrhea Toxicity 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
238000006477 desulfuration reaction Methods 0.000 description 1
230000023556 desulfurization Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003210 dopamine receptor blocking agent Substances 0.000 description 1
230000003291 dopaminomimetic effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000035929 gnawing Effects 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000026045 iodination Effects 0.000 description 1
238000006192 iodination reaction Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
RSEAASAWECJNTP-DXCKQFNASA-N methyl (6aR,9S,10aR)-9-(2,2-dimethylpropanoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-5-carboxylate Chemical compound C(=O)(OC)C1=C2C[C@H]3N(C[C@H](C[C@@H]3C=3C=CC=C(N1)C32)NC(C(C)(C)C)=O)C RSEAASAWECJNTP-DXCKQFNASA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
208000030153 prolactin-producing pituitary gland adenoma Diseases 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
JUDXOKKZTISQDJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 JUDXOKKZTISQDJ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LU86743A 1986-01-24 1987-01-22 Nouvelles 8a-acylamino-ergolines,leur preparation et leur utilisation comme medicaments LU86743A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3602058		1986-01-24
DE3602058		1986-01-24

Publications (1)

Publication Number	Publication Date
LU86743A1 true LU86743A1 (fr)	1987-09-03

Family

ID=6292510

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86743A LU86743A1 (fr)	1986-01-24	1987-01-22	Nouvelles 8a-acylamino-ergolines,leur preparation et leur utilisation comme medicaments

Country Status (18)

Country	Link
JP (1)	JPS62190184A (da)
KR (1)	KR870007175A (da)
AU (1)	AU6791487A (da)
BE (1)	BE1000039A4 (da)
DK (1)	DK35787A (da)
ES (1)	ES2003774A6 (da)
FI (1)	FI870293A7 (da)
FR (1)	FR2595699A1 (da)
GB (1)	GB2185743A (da)
GR (1)	GR870093B (da)
HU (1)	HUT45248A (da)
IL (1)	IL81355A0 (da)
IT (1)	IT1216783B (da)
LU (1)	LU86743A1 (da)
NL (1)	NL8700046A (da)
PT (1)	PT84184A (da)
SE (1)	SE8700250L (da)
ZA (1)	ZA87520B (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8714767D0 (en) *	1987-06-24	1987-07-29	Erba Farmitalia	Egoline derivatives
DE3587860D1 (de) *	1984-04-09	1994-07-28	Schering Ag	2-substituierte Ergolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel.
DK338789A (da) *	1988-07-15	1990-01-16	Schering Ag	2-substituerede ergolinylurinstofderivater og fremgangsmaade til fremstilling deraf, deres anvendelse som laegemidler samt mellemprodukter til fremstilling deraf
DE3915950A1 (de) *	1989-05-12	1990-11-15	Schering Ag	8(alpha)-acylamino-ergoline, ihre herstellung und verwendung als arzneimittel
KR20140042868A (ko) *	2011-06-23	2014-04-07	맵 파마슈티컬스, 인코포레이티드	신규한 플루오로에르골린 유사체
SG10201509139QA (en) *	2011-12-19	2015-12-30	Map Pharmaceuticals Inc	Novel iso-ergoline derivatives
MX2017009405A (es)	2015-01-20	2018-01-18	Xoc Pharmaceuticals Inc	Compuestos de tipo ergolina y usos de estos.
EP3247357A4 (en) *	2015-01-20	2018-07-11	Xoc Pharmaceuticals, Inc	Isoergoline compounds and uses thereof
WO2018223065A1 (en)	2017-06-01	2018-12-06	Xoc Pharmaceuticals, Inc.	Ergoline derivatives for use in medicine

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1517973A (en) *	1974-07-19	1978-07-19	Sandoz Ltd	6-methyl-8alpha-n,n-dimethylsulphamoylaminoergoline i
CH615929A5 (en) *	1975-06-02	1980-02-29	Sandoz Ag	Process for the preparation of novel ergoline compounds
HU197569B (en) *	1984-01-12	1989-04-28	Sandoz Ag	Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds

1987
- 1987-01-12 NL NL8700046A patent/NL8700046A/nl not_active Application Discontinuation
- 1987-01-12 HU HU8792A patent/HUT45248A/hu unknown
- 1987-01-21 GB GB08701274A patent/GB2185743A/en not_active Withdrawn
- 1987-01-22 SE SE8700250A patent/SE8700250L/xx not_active Application Discontinuation
- 1987-01-22 DK DK035787A patent/DK35787A/da not_active Application Discontinuation
- 1987-01-22 ES ES8700163A patent/ES2003774A6/es not_active Expired
- 1987-01-22 IL IL81355A patent/IL81355A0/xx unknown
- 1987-01-22 IT IT8747551A patent/IT1216783B/it active
- 1987-01-22 PT PT84184A patent/PT84184A/pt unknown
- 1987-01-22 KR KR870000556A patent/KR870007175A/ko not_active Ceased
- 1987-01-22 LU LU86743A patent/LU86743A1/fr unknown
- 1987-01-22 FR FR8700834A patent/FR2595699A1/fr active Pending
- 1987-01-22 GR GR870093A patent/GR870093B/el unknown
- 1987-01-22 AU AU67914/87A patent/AU6791487A/en not_active Abandoned
- 1987-01-23 ZA ZA87520A patent/ZA87520B/xx unknown
- 1987-01-23 BE BE8700046A patent/BE1000039A4/fr not_active IP Right Cessation
- 1987-01-23 JP JP62015028A patent/JPS62190184A/ja active Pending
- 1987-01-23 FI FI870293A patent/FI870293A7/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI870293A7 (fi)	1987-07-25
AU6791487A (en)	1987-07-30
FI870293A0 (fi)	1987-01-23
HUT45248A (en)	1988-06-28
DK35787A (da)	1987-07-25
GR870093B (en)	1987-05-25
SE8700250L (sv)	1987-07-25
FR2595699A1 (fr)	1987-09-18
KR870007175A (ko)	1987-08-17
BE1000039A4 (fr)	1987-12-15
SE8700250D0 (sv)	1987-01-22
IT1216783B (it)	1990-03-14
PT84184A (pt)	1987-02-01
ES2003774A6 (es)	1988-11-16
NL8700046A (nl)	1987-08-17
DK35787D0 (da)	1987-01-22
IT8747551A0 (it)	1987-01-22
JPS62190184A (ja)	1987-08-20
IL81355A0 (en)	1987-08-31
GB8701274D0 (en)	1987-02-25
GB2185743A (en)	1987-07-29
ZA87520B (en)	1988-09-28

Publication	Publication Date	Title
EP0202164B1 (fr)	1989-02-08	Dérivés de (benzoyl-4 pipéridino)-2 phenyl-1 alcanols, leur préparation et leur application en thérapeutique
FR2557110A1 (fr)	1985-06-28	Nouveaux derives d'amines cycliques, leur preparation et leur utilisation comme medicaments
FR2501686A1 (fr)	1982-09-17	Nouveaux derives de 3,4-dihydro-5h-2,3-benzodiazepine, procede pour les preparer et medicaments les contenant
FR2531707A1 (fr)	1984-02-17	Trifluoromethylphenyltetrahydropyridines substituees a activite anorexigene, un procede de preparation et compositions pharmaceutiques
FR2601015A1 (fr)	1988-01-08	Nouveaux derives du 1h,3h-pyrrolo (1,2-c) thiazole, leur preparation et les compositions pharmaceutiques qui les contiennent
LU85191A1 (fr)	1984-10-24	Nouveaux derives de la benzo(g)quinoleine,leur preparation et leur utilisation comme medicaments
LU86743A1 (fr)	1987-09-03	Nouvelles 8a-acylamino-ergolines,leur preparation et leur utilisation comme medicaments
EP0004494B1 (fr)	1982-02-17	Nouveaux dérivés de 1,3-dihydro 3-(1-(2-(2,3-dihydro 1,4-benzo-dioxin-2-yl)2-hydroxy éthyl)pipéridin-4-yl)2H-indol 2-one, leur procédé de préparation, leur application comme médicaments et les compositions pharmaceutiques les renfermant
CA1095047A (fr)	1981-02-03	Procede de preparation de nouveaux derives du 1,4- benzodioxane
FR2560196A1 (fr)	1985-08-30	Nouvelles 8a-acylaminoergolines, leur preparation et leur utilisation comme medicaments
FR2662695A1 (fr)	1991-12-06	Amino-2 polyfluoroalcoxy-6 benzoselenazoles, leur preparation et les medicaments les contenant.
CA1117944A (fr)	1982-02-09	Procedes de preparation de nouvelles piperazines disubstituees
FR2643634A1 (fr)	1990-08-31	Nouveaux derives benzoxazolinoniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
FR2753970A1 (fr)	1998-04-03	Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique
CH633010A5 (fr)	1982-11-15	Derives de l'isoquinoleine, leur preparation et medicament qui les contient.
EP1960387B1 (fr)	2011-11-02	Derives de isoquinoline et benzo[h]isoquinoline, leur preparation et leur utilisation en therapeutique en tant qu antagonistes du recepteur de l histamine h3
CA1167444A (fr)	1984-05-15	Derives de la chloro-3 quinoleine, procedes pour leur preparation, et leur utilisation comme medicaments
LU86226A1 (fr)	1986-06-25	Nouvelles 8-acylaminoergolines,leur preparation,leur utilisation comme medicaments et les compositions pharmaceutiques les contenant
MC1562A1 (fr)	1984-11-12	Phenothiazines,leur procede de preparation et produits en contenant
FR2531433A1 (fr)	1984-02-10	Nouveaux alcaloides de l'ergot de seigle, leur preparation et leur utilisation comme medicaments
EP1560825A1 (fr)	2005-08-10	Nouveaux derives de 2,3-dihydro-4(1h)-pyridinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2751332A1 (fr)	1998-01-23	Derives d'oxopyrrolopyrrole, procede pour leur preparation, compositions pharmaceutiques les contenant et leur utilisation
FR2510996A1 (fr)	1983-02-11	Nouveaux derives du dibenz(cd,f)indole et leur preparation
CH635590A5 (fr)	1983-04-15	Derives de l'isoquinoleine, leur preparation et compositions pharmaceutiques qui les contiennent.
FR2692895A1 (fr)	1993-12-31	Nouveaux 1-oxo 2,4,5,6-tétrahydro 2,3,7-triazaphénalènes leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent.