HU197569B - Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds - Google Patents
Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds Download PDFInfo
- Publication number
- HU197569B HU197569B HU8524A HU2485A HU197569B HU 197569 B HU197569 B HU 197569B HU 8524 A HU8524 A HU 8524A HU 2485 A HU2485 A HU 2485A HU 197569 B HU197569 B HU 197569B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- methyl
- alkyl
- hydrogen
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 238000000034 method Methods 0.000 title claims description 20
- 239000003814 drug Substances 0.000 title description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 239000000460 chlorine Chemical group 0.000 claims abstract description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 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
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- QXOFQMUQMXGKGQ-NORZTCDRSA-N n-[(6ar,9s,10ar)-5-chloro-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2,2-dimethylpropanamide Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)C)NC(=O)C(C)(C)C)=C3C2=C(Cl)NC3=C1 QXOFQMUQMXGKGQ-NORZTCDRSA-N 0.000 claims 2
- NZJCQZHTKZKQFG-IYYTYJHQSA-N (6aR,9S,10aR)-5-chloro-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-amine Chemical compound N[C@@H]1CN([C@@H]2CC3=C(NC4=CC=CC([C@H]2C1)=C34)Cl)C NZJCQZHTKZKQFG-IYYTYJHQSA-N 0.000 claims 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- ZNMWUMGOSWLWOH-FDQGKXFDSA-N n-[(6ar,9s,10ar)-5,7-dimethyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2,2-dimethylpropanamide Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)C)NC(=O)C(C)(C)C)=C3C2=C(C)NC3=C1 ZNMWUMGOSWLWOH-FDQGKXFDSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 9
- 230000000701 neuroleptic effect Effects 0.000 abstract description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- -1 di-substituted phenyl Chemical group 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- 230000000694 effects Effects 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 239000000047 product Substances 0.000 description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000003136 dopamine receptor stimulating agent Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
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- 229940088597 hormone Drugs 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- RKZACOKFBAFYPQ-PSOPSSQASA-N (6ar,9s,10ar)-5,7-dimethyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-amine Chemical compound C1=CC([C@H]2C[C@H](N)CN([C@@H]2C2)C)=C3C2=C(C)NC3=C1 RKZACOKFBAFYPQ-PSOPSSQASA-N 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
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- 206010020880 Hypertrophy Diseases 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000001592 luteinising effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000009245 menopause Effects 0.000 description 1
- 230000005906 menstruation Effects 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- YVINMEPKNAWFQW-JCKWVBRZSA-N n-[(6ar,9s,10ar)-5-bromo-7-propyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2,2-dimethylpropanamide Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)CCC)NC(=O)C(C)(C)C)=C3C2=C(Br)NC3=C1 YVINMEPKNAWFQW-JCKWVBRZSA-N 0.000 description 1
- OYFDEHPPDAQSHE-JCKWVBRZSA-N n-[(6ar,9s,10ar)-5-chloro-7-propyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-yl]-2,2-dimethylpropanamide Chemical compound C1=CC([C@H]2C[C@@H](CN([C@@H]2C2)CCC)NC(=O)C(C)(C)C)=C3C2=C(Cl)NC3=C1 OYFDEHPPDAQSHE-JCKWVBRZSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 210000004681 ovum Anatomy 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XNQULTQRGBXLIA-UHFFFAOYSA-O phosphonic anhydride Chemical compound O[P+](O)=O XNQULTQRGBXLIA-UHFFFAOYSA-O 0.000 description 1
- 230000007180 physiological regulation Effects 0.000 description 1
- 230000026234 pro-estrus Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
-
- 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
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 8
- C07D457/06—Lysergic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/10—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hetero atoms directly attached in position 8
- C07D457/12—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3400853 | 1984-01-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT37148A HUT37148A (en) | 1985-11-28 |
| HU197569B true HU197569B (en) | 1989-04-28 |
Family
ID=6224786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU8524A HU197569B (en) | 1984-01-12 | 1985-01-03 | Process for producing 8alpha-acylaminoergoline derivatives and pharmaceuticals comprising such compounds |
Country Status (28)
| Country | Link |
|---|---|
| US (2) | US4950672A (OSRAM) |
| JP (1) | JPH0655739B2 (OSRAM) |
| AT (1) | AT391317B (OSRAM) |
| AU (3) | AU583489B2 (OSRAM) |
| BE (1) | BE901456A (OSRAM) |
| CA (1) | CA1245640A (OSRAM) |
| CH (1) | CH664568A5 (OSRAM) |
| CY (1) | CY1542A (OSRAM) |
| DE (1) | DE3500251C2 (OSRAM) |
| DK (1) | DK169891B1 (OSRAM) |
| ES (1) | ES8605514A1 (OSRAM) |
| FI (1) | FI82466C (OSRAM) |
| FR (1) | FR2560196B1 (OSRAM) |
| GB (1) | GB2152507B (OSRAM) |
| GR (1) | GR850065B (OSRAM) |
| HK (1) | HK48590A (OSRAM) |
| HU (1) | HU197569B (OSRAM) |
| IE (1) | IE58228B1 (OSRAM) |
| IL (1) | IL74043A (OSRAM) |
| IT (1) | IT1214648B (OSRAM) |
| LU (1) | LU85725A1 (OSRAM) |
| NL (1) | NL193541C (OSRAM) |
| NZ (1) | NZ210818A (OSRAM) |
| PH (1) | PH23286A (OSRAM) |
| PT (1) | PT79818B (OSRAM) |
| SE (1) | SE460420B (OSRAM) |
| SG (1) | SG32390G (OSRAM) |
| ZA (1) | ZA85276B (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL193541C (nl) * | 1984-01-12 | 2000-01-04 | Novartis Ag | 8 Alfa-acylaminoergolinen, werkwijzen voor de bereiding daarvan en preparaten die ze bevatten. |
| ATE107647T1 (de) * | 1984-04-09 | 1994-07-15 | Schering Ag | 2-substituierte ergolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
| NL8700046A (nl) * | 1986-01-24 | 1987-08-17 | Sandoz Ag | 8 alfa-acylaminoergolinen, werkwijzen voor hun bereiding en farmaceutische preparaten die ze bevatten. |
| US4931447A (en) * | 1987-06-15 | 1990-06-05 | Eli Lilly And Company | Cycloalkylamides of (8β)-1-alkyl-6-(substituted) ergolines |
| US4981859A (en) * | 1987-06-15 | 1991-01-01 | Cycloalkylamides of (8 beta )-1-alkyl-6-(substituted)ergolines | |
| IT1219652B (it) * | 1987-06-23 | 1990-05-24 | Sandoz Ag | 8-acilamminoergolina,la sua preparazione e il suo impiego come medicamneto |
| DE3820159A1 (de) * | 1987-06-23 | 1989-01-05 | Sandoz Ag | 8(alpha)-acylaminoergolin, seine herstellung und dieses enthaltende 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 |
| GB8824744D0 (en) * | 1988-10-21 | 1988-11-30 | Erba Carlo Spa | Antiemesis ergoline derivatives |
| DE3915950A1 (de) * | 1989-05-12 | 1990-11-15 | Schering Ag | 8(alpha)-acylamino-ergoline, ihre herstellung und verwendung als arzneimittel |
| CA2974113A1 (en) | 2015-01-20 | 2016-07-28 | Xoc Pharmaceuticals, Inc. | Isoergoline compounds and uses thereof |
| BR112017015487A2 (pt) | 2015-01-20 | 2018-01-30 | Xoc Pharmaceuticals Inc | Composto; composição; método de tratamento e/ou prevenção de enxaqueca, als, doença de alzheimer, doença de parkinson, distúrbios extrapirimidais, depressão, náusea, êmese, síndrome das pernas inquietas, insônia, agressão, doença de huntington, doença cardiopulmonar, fibrogênese, hipertensão arterial pulmonar, ansiedade, dependências a drogas, distonia, parassonia ou hiperlactinemia em um indivíduo; métodos de agonização dos receptores d2, 5-ht1d, 5-ht1a e 5-ht2c, em um indivíduo; método de antagonização do receptor d3 em um indivíduo; métodos de agonização seletiva dos receptores 5 -ht1d, e 5-ht2c, método de fornecimento de atividade de antagonista funcional no receptor 5 -ht2b ou no receptor 5-ht7, ou em ambos, em um indivíduo; método de fornecimento de atividade de antagonista funcional nos receptores adrenérgicos em um indivíduo |
| CA3064274A1 (en) | 2017-06-01 | 2018-12-06 | Xoc Pharmaceuticals, Inc. | Ergoline derivatives for use in medicine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3218323A (en) * | 1965-11-16 | Esters of i,g-dimethyl-b-ergolenyl carbamic acid | ||
| US2864822A (en) * | 1956-10-22 | 1958-12-16 | Lilly Co Eli | 9-amino-7-methyl-belta10-ergolene and derivatives thereof |
| CH622519A5 (en) * | 1974-07-05 | 1981-04-15 | Hoechst Ag | Process for the preparation of hydroxyalkylxanthines |
| US4348392A (en) * | 1974-07-19 | 1982-09-07 | Sandoz Ltd. | 8α-Substituted ergoline-I derivatives |
| GB1517973A (en) * | 1974-07-19 | 1978-07-19 | Sandoz Ltd | 6-methyl-8alpha-n,n-dimethylsulphamoylaminoergoline i |
| US3922347A (en) * | 1974-12-19 | 1975-11-25 | Lilly Co Eli | Method of inhibiting prolactin secretion with 8-acylaminoergolenes |
| CH615929A5 (en) * | 1975-06-02 | 1980-02-29 | Sandoz Ag | Process for the preparation of novel ergoline compounds |
| DE2656344A1 (de) * | 1975-12-23 | 1977-07-07 | Sandoz Ag | Ergolinderivate, ihre verwendung und herstellung |
| CH622518A5 (en) * | 1976-12-14 | 1981-04-15 | Sandoz Ag | Process for the preparation of novel ergoline compounds |
| CH644606A5 (de) * | 1980-09-23 | 1984-08-15 | Sandoz Ag | Verfahren zur isomerisierung von 9,10-dihydrolysergsaeurederivaten. |
| 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 |
| NL193541C (nl) * | 1984-01-12 | 2000-01-04 | Novartis Ag | 8 Alfa-acylaminoergolinen, werkwijzen voor de bereiding daarvan en preparaten die ze bevatten. |
| HU195810B (en) * | 1984-12-24 | 1988-07-28 | Sandoz Ag | Process for preparing new 8alpha-acyl-amino-ergoline derivatives and pharmaceutical compositions containing such compounds |
| IT1219652B (it) * | 1987-06-23 | 1990-05-24 | Sandoz Ag | 8-acilamminoergolina,la sua preparazione e il suo impiego come medicamneto |
-
1985
- 1985-01-03 NL NL8500008A patent/NL193541C/nl not_active IP Right Cessation
- 1985-01-03 CH CH16/85A patent/CH664568A5/de not_active IP Right Cessation
- 1985-01-03 HU HU8524A patent/HU197569B/hu unknown
- 1985-01-05 DE DE3500251A patent/DE3500251C2/de not_active Expired - Fee Related
- 1985-01-07 FR FR8500217A patent/FR2560196B1/fr not_active Expired
- 1985-01-08 BE BE1/11168A patent/BE901456A/fr not_active IP Right Cessation
- 1985-01-08 GB GB08500454A patent/GB2152507B/en not_active Expired
- 1985-01-10 SE SE8500107A patent/SE460420B/sv not_active IP Right Cessation
- 1985-01-10 CA CA000471859A patent/CA1245640A/en not_active Expired
- 1985-01-10 PT PT79818A patent/PT79818B/pt not_active IP Right Cessation
- 1985-01-10 IE IE6485A patent/IE58228B1/en not_active IP Right Cessation
- 1985-01-10 LU LU85725A patent/LU85725A1/fr unknown
- 1985-01-10 GR GR850065A patent/GR850065B/el unknown
- 1985-01-10 DK DK012685A patent/DK169891B1/da active
- 1985-01-11 FI FI850130A patent/FI82466C/fi not_active IP Right Cessation
- 1985-01-11 AU AU37609/85A patent/AU583489B2/en not_active Ceased
- 1985-01-11 ES ES539511A patent/ES8605514A1/es not_active Expired
- 1985-01-11 JP JP60003913A patent/JPH0655739B2/ja not_active Expired - Lifetime
- 1985-01-11 IT IT8547538A patent/IT1214648B/it active
- 1985-01-11 ZA ZA85276A patent/ZA85276B/xx unknown
- 1985-01-11 IL IL74043A patent/IL74043A/xx not_active IP Right Cessation
- 1985-01-11 NZ NZ210818A patent/NZ210818A/xx unknown
- 1985-01-11 AT AT0005985A patent/AT391317B/de not_active IP Right Cessation
- 1985-01-14 PH PH31714A patent/PH23286A/en unknown
-
1988
- 1988-11-11 AU AU25066/88A patent/AU609539B2/en not_active Ceased
- 1988-11-11 AU AU25067/88A patent/AU618290B2/en not_active Ceased
-
1989
- 1989-02-27 US US07/316,363 patent/US4950672A/en not_active Expired - Fee Related
-
1990
- 1990-05-02 SG SG32390A patent/SG32390G/en unknown
- 1990-06-21 HK HK485/90A patent/HK48590A/xx not_active IP Right Cessation
- 1990-07-02 US US07/547,899 patent/US5077298A/en not_active Expired - Lifetime
-
1991
- 1991-03-22 CY CY1542A patent/CY1542A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HPC4 | Succession in title of patentee |
Owner name: NOVARTIS AG., CH |