DK168438B1 - 12- og 13-bromergolinderivater, fremgangsmåde til fremstilling heraf samt mellemprodukt til brug ved deres fremstilling - Google Patents

12- og 13-bromergolinderivater, fremgangsmåde til fremstilling heraf samt mellemprodukt til brug ved deres fremstilling Download PDF

Info

Publication number: DK168438B1
Authority: DK; Denmark
Prior art keywords: bromo; methyl; compounds; preparation; diethylurea
Prior art date: 1985-09-19

Application number

DK450086A

Other languages

Danish (da)

English (en)

Other versions

DK450086D0 (da

DK450086A (da

Inventor

Gerhard Sauer

Josef Heindl

Gertrud Schroeder

Helmut Wachtel

Original Assignee

Schering 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.)

1985-09-19

Filing date

1986-09-19

Publication date

1994-03-28

1986-09-19 Application filed by Schering Ag filed Critical Schering Ag

1986-09-19 Publication of DK450086D0 publication Critical patent/DK450086D0/da

1987-03-20 Publication of DK450086A publication Critical patent/DK450086A/da

1994-03-28 Application granted granted Critical

1994-03-28 Publication of DK168438B1 publication Critical patent/DK168438B1/da

Links

238000002360 preparation method Methods 0.000 title claims description 10
238000000034 method Methods 0.000 title claims description 9
239000000543 intermediate Substances 0.000 title abstract description 5
PFDOIIKNUZUWCE-ZYHUDNBSSA-N (6ar,10ar)-2-bromo-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline Chemical class C([C@@H]12)CCN[C@@H]1CC1=CNC3=CC(Br)=CC2=C31 PFDOIIKNUZUWCE-ZYHUDNBSSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims description 3
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
239000007858 starting material Substances 0.000 claims description 3
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 2
ORLXWYWZAITENH-HDMKZQKVSA-N 3-[(6ar,9s,10ar)-2-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound BrC1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 ORLXWYWZAITENH-HDMKZQKVSA-N 0.000 claims description 2
239000004202 carbamide Substances 0.000 claims description 2
238000005984 hydrogenation reaction Methods 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 3
229940079593 drug Drugs 0.000 abstract description 2
208000020016 psychiatric disease Diseases 0.000 abstract description 2
208000024891 symptom Diseases 0.000 abstract description 2
230000003001 depressive effect Effects 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
-1 aliphatic mono- Chemical class 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229960001701 chloroform Drugs 0.000 description 7
239000000126 substance Substances 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 6
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
229960002896 clonidine Drugs 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
JOAHPSVPXZTVEP-UHFFFAOYSA-N 1,1-diethyl-3-(7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl)urea Chemical compound C1=CC(C2CC(CN(C)C2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
239000012043 crude product Substances 0.000 description 4
150000002168 ethanoic acid esters Chemical class 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
JOAHPSVPXZTVEP-YXJHDRRASA-N Terguride Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 JOAHPSVPXZTVEP-YXJHDRRASA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
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 3
229960004046 apomorphine Drugs 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
235000013405 beer Nutrition 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
230000002631 hypothermal effect Effects 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
230000007017 scission Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
UMYIAENJMRDGQL-PMUMKWKESA-N 3-[(6ar,9s,10ar)-2-bromo-7-methyl-5-methylsulfanyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound BrC1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=C(SC)NC3=C1 UMYIAENJMRDGQL-PMUMKWKESA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
230000001430 anti-depressive effect Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000013078 crystal Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000003993 interaction Effects 0.000 description 2
239000007788 liquid Substances 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
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
239000000047 product Substances 0.000 description 2
239000003586 protic polar solvent Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
229960004558 terguride Drugs 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
TUMNHQRORINJKE-UHFFFAOYSA-N 1,1-diethylurea Chemical compound CCN(CC)C(N)=O TUMNHQRORINJKE-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
IIEJGTQVBJHMDL-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-[2-oxo-2-[3-(sulfamoylamino)pyrrolidin-1-yl]ethyl]-1,3,4-oxadiazole Chemical compound C1CN(CC1NS(=O)(=O)N)C(=O)CC2=NN=C(O2)C3=CN=C(N=C3)NC4CC5=CC=CC=C5C4 IIEJGTQVBJHMDL-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
QCNGAMOXYCNYKP-IUVQAAGXSA-N 3-[(5ar,6ar,9s,10ar)-4-acetyl-1-bromo-7-methyl-5,5a,6,6a,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound C1N(C(C)=O)C2=CC=C(Br)C3=C2[C@H]1C[C@@H]1[C@@H]3C[C@H](NC(=O)N(CC)CC)CN1C QCNGAMOXYCNYKP-IUVQAAGXSA-N 0.000 description 1
ODORZRSDJPRZED-GRDNDAEWSA-N 3-[(6ar,9s,10ar)-1-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-1,1-diethylurea Chemical compound C1=C(Br)C([C@H]2C[C@@H](CN(C)[C@@H]2C2)NC(=O)N(CC)CC)=C3C2=CNC3=C1 ODORZRSDJPRZED-GRDNDAEWSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
SJZRECIVHVDYJC-UHFFFAOYSA-M 4-hydroxybutyrate Chemical compound OCCCC([O-])=O SJZRECIVHVDYJC-UHFFFAOYSA-M 0.000 description 1
OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
229940098778 Dopamine receptor agonist Drugs 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
TXQGSQGEEXNHOS-HRBVQNPCSA-N [(6ar,10ar)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-yl]urea Chemical class C1=CC([C@@H]2[C@H](NCC(C2)NC(=O)N)C2)=C3C2=CNC3=C1 TXQGSQGEEXNHOS-HRBVQNPCSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
230000001090 anti-dopaminergic effect Effects 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
JOYKCMAPFCSKNO-UHFFFAOYSA-N chloro benzenesulfonate Chemical compound ClOS(=O)(=O)C1=CC=CC=C1 JOYKCMAPFCSKNO-UHFFFAOYSA-N 0.000 description 1
KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
229940044175 cobalt sulfate Drugs 0.000 description 1
229910000361 cobalt sulfate Inorganic materials 0.000 description 1
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
RHGUXDUPXYFCTE-ZWNOBZJWSA-N ergoline Chemical class C1=CC([C@@H]2[C@H](NCCC2)C2)=C3C2=CNC3=C1 RHGUXDUPXYFCTE-ZWNOBZJWSA-N 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
KKLGDUSGQMHBPB-UHFFFAOYSA-N hex-2-ynedioic acid Chemical compound OC(=O)CCC#CC(O)=O KKLGDUSGQMHBPB-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
239000000523 sample Substances 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000028016 temperature homeostasis Effects 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229940071104 xylenesulfonate Drugs 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
- C07D457/12—Nitrogen atoms
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/24—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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

DK450086A 1985-09-19 1986-09-19 12- og 13-bromergolinderivater, fremgangsmåde til fremstilling heraf samt mellemprodukt til brug ved deres fremstilling DK168438B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19853533675 DE3533675A1 (de)	1985-09-19	1985-09-19	Neue 12- und 13-brom-ergolinderivate
DE3533675		1985-09-19

Publications (3)

Publication Number	Publication Date
DK450086D0 DK450086D0 (da)	1986-09-19
DK450086A DK450086A (da)	1987-03-20
DK168438B1 true DK168438B1 (da)	1994-03-28

Family

ID=6281551

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK450086A DK168438B1 (da)	1985-09-19	1986-09-19	12- og 13-bromergolinderivater, fremgangsmåde til fremstilling heraf samt mellemprodukt til brug ved deres fremstilling

Country Status (10)

Country	Link
US (1)	US4740509A (cs)
EP (1)	EP0217734B1 (cs)
JP (1)	JPH0670050B2 (cs)
AT (1)	ATE69816T1 (cs)
CA (1)	CA1291121C (cs)
CS (1)	CS256364B2 (cs)
DE (2)	DE3533675A1 (cs)
DK (1)	DK168438B1 (cs)
HU (1)	HU196599B (cs)
IE (1)	IE58894B1 (cs)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3151912A1 (de) *	1981-12-23	1983-06-30	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue ergolin-aminoderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
ATE107647T1 (de) *	1984-04-09	1994-07-15	Schering Ag	2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.
DE3528576A1 (de) *	1985-08-06	1987-02-19	Schering Ag	Verfahren zur herstellung von ergolin-thioharnstoffen
DE3533672A1 (de) *	1985-09-19	1987-03-26	Schering Ag	Neue 12- und 13-substituierte ergolinderivate
DE3535929A1 (de) *	1985-10-04	1987-04-09	Schering Ag	1,2-disubstituierte ergolinderivate
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
DE3931819A1 (de) *	1989-09-20	1991-03-28	Schering Ag	13-brom und 13, 14-dibrom-ergoline, ihre herstellung und verwendung in arzneimitteln
DE4001323A1 (de) *	1990-01-15	1991-07-18	Schering Ag	2,13-disubstituierte ergoline, deren herstellung und verwendung in arzneimitteln
EP4423084A4 (en) *	2021-10-26	2025-12-10	Diamond Therapeutics Inc	5-HT2A RECEPTOR ERGOLINE-DERIVED AGONISTS

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE309493C (cs) *
DE330912C (de) *	1918-02-07	1920-12-22	Reinhold Braeuer	Geschuetz mit verstellbarer Bettung
DE445784C (de) *	1925-12-13	1927-06-17	Siemens Schuckertwerke G M B H	Als blanke Schiene verlegte Stromleitung, insbesondere Verstaerkungsleitung, fuer Strom-zufuehrung durch dritte Schiene, bestehend aus mehreren duennen Flachkupferschienen
CH573936A5 (cs) *	1971-08-05	1976-03-31	Spofa Vereinigte Pharma Werke
GB1413068A (en) *	1972-06-22	1975-11-05	Farmaceutici Italia	Bromoergolines
CH584220A5 (en) *	1972-09-26	1977-01-31	Sandoz Ag	13-Bromo-lysergic acid derivs - with vigilance-increasing activity
DE2924102A1 (de) *	1979-06-13	1980-12-18	Schering Ag	Neue (ergolin-yl)-n'.n'-diaethylharnstoffderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
DE3063869D1 (en) *	1979-06-13	1983-07-28	Schering Ag	(ergolin-yl)-n', n'-diethyl urea derivatives, their preparation and pharmaceutical compositions containing them
DE3001752A1 (de) *	1980-01-16	1981-07-30	Schering Ag Berlin Und Bergkamen, 1000 Berlin	Verfahren zur herstellung von 8(alpha)-substituierten 6-methylergolinen
CH644606A5 (de) *	1980-09-23	1984-08-15	Sandoz Ag	Verfahren zur isomerisierung von 9,10-dihydrolysergsaeurederivaten.
DE3101535A1 (de) *	1981-01-14	1982-08-12	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue (2-halogen-ergolinyl)-n'.n'-diethyl-harnstoffderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
DE3151912A1 (de) *	1981-12-23	1983-06-30	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue ergolin-aminoderivate, verfahren zu ihrer herstellung und deren verwendung als arzneimittel
DE3309493A1 (de) *	1983-03-14	1984-09-20	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue ergolin-derivate, verfahren zu ihrer herstellung sowie verwendung als arzneimittel
ATE107647T1 (de) *	1984-04-09	1994-07-15	Schering Ag	2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel.
DE3413657A1 (de) *	1984-04-09	1985-10-17	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue ergoline
DE3445784A1 (de) *	1984-12-13	1986-06-26	Schering AG, Berlin und Bergkamen, 1000 Berlin	Verfahren zur herstellung von ergolin-derivaten

1985
- 1985-09-19 DE DE19853533675 patent/DE3533675A1/de not_active Withdrawn
1986
- 1986-09-18 HU HU863991A patent/HU196599B/hu not_active IP Right Cessation
- 1986-09-18 CA CA000518528A patent/CA1291121C/en not_active Expired - Lifetime
- 1986-09-18 DE DE8686730146T patent/DE3682645D1/de not_active Expired - Lifetime
- 1986-09-18 EP EP86730146A patent/EP0217734B1/de not_active Expired - Lifetime
- 1986-09-18 AT AT86730146T patent/ATE69816T1/de not_active IP Right Cessation
- 1986-09-18 IE IE248586A patent/IE58894B1/en not_active IP Right Cessation
- 1986-09-19 US US06/909,837 patent/US4740509A/en not_active Expired - Fee Related
- 1986-09-19 JP JP61219891A patent/JPH0670050B2/ja not_active Expired - Lifetime
- 1986-09-19 DK DK450086A patent/DK168438B1/da not_active IP Right Cessation
- 1986-09-19 CS CS866750A patent/CS256364B2/cs unknown

Also Published As

Publication number	Publication date
HUT41783A (en)	1987-05-28
DK450086D0 (da)	1986-09-19
HU196599B (en)	1988-12-28
CS675086A2 (en)	1987-08-13
JPS62111983A (ja)	1987-05-22
DK450086A (da)	1987-03-20
DE3682645D1 (de)	1992-01-09
IE58894B1 (en)	1993-12-01
JPH0670050B2 (ja)	1994-09-07
EP0217734A1 (de)	1987-04-08
IE862485L (en)	1987-03-19
US4740509A (en)	1988-04-26
EP0217734B1 (de)	1991-11-27
ATE69816T1 (de)	1991-12-15
CA1291121C (en)	1991-10-22
CS256364B2 (en)	1988-04-15
DE3533675A1 (de)	1987-03-26

Legal Events

Date	Code	Title	Description
1994-03-28	B1	Patent granted (law 1993)
1997-05-20	PBP	Patent lapsed

Publication	Publication Date	Title
US4353827A (en)	1982-10-12	Diazepine derivatives
DK142498B (da)	1980-11-10	Analogifremgangsmåde til fremstilling af benzopyridoazepinderivater.
CS273193B2 (en)	1991-03-12	Method of new tetrahydrofuro- and -thienol (2,3-c) pyridine production
NO175259B (no)	1994-06-13	Analogifremgangsmåte for fremstilling av terapeutisk aktive triazolo-1,4-diazepinforbindelser
CA2863259A1 (en)	2013-07-18	Irak inhibitors and uses thereof
NO329559B1 (no)	2010-11-15	Fremgangsmate for a fremstille modafinil
WO2009015828A1 (en)	2009-02-05	Paliperidone derivatives
AU716008B2 (en)	2000-02-17	Bicyclic benzazepine derivatives as vasopressin antagonists
IE57057B1 (en)	1992-04-08	Carboxamides,process for their preparation and pharmaceutical preparations containing them
DK153844B (da)	1988-09-12	Analogifremgangsmaade til fremstilling af 1,2,3,5-tetrahydroimidazothienopyrimidin-2-oner
NO129043B (cs)	1974-02-18
CA2895829A1 (en)	2014-06-26	Novel methysergide derivatives
US5084454A (en)	1992-01-28	2-(piperidinylmethyl)-4-phenyl-2,3-dihydro-4h-1,4-benzoxazines useful as antipsychotics
EP2513118A1 (en)	2012-10-24	Bicyclic thiazoles as allosteric modulators of mglur5 receptors
IE58894B1 (en)	1993-12-01	12- and 13-bromoergoline derivatives
AU650792B2 (en)	1994-06-30	Triazaspirodecanone-methylchromans
CS248739B2 (en)	1987-02-12	Production method of the new 2-substituted derivatives of ergoline
NO142260B (no)	1980-04-14	Analogifremgangsmaate ved fremstilling av terapeutisk aktive tienotriazolodiazepinderivater
EP1509530B1 (en)	2006-03-15	2-thia-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof
GB2185743A (en)	1987-07-29	8 alpha -Acylaminoergoline's
RU2496769C2 (ru)	2013-10-27	Производные бензоциклогептана и бензоксепина
EP1506204A2 (en)	2005-02-16	1-oxa-dibenzoazulenes as inhibitors of tumor necrosis factor production and intermediates for the preparation thereof
Löfås et al.	1984	Spiro‐and bicyclic azalactams by hydrolysis of α‐chlorinated bicyclic amidines
NO160203B (no)	1988-12-12	Analogifremgangsmaate for fremstilling av terapeutisk virksomme fenotiazin-forbindelser.
TWI619697B (zh)	2018-04-01	亞碸化合物及其用於製造苯並噻吩衍生物之方法