SE452011B - Ergopeptinderivat, forfarande for deras framstellning och farmaceutiska kompositioner innehallande dessa derivat - Google Patents
Ergopeptinderivat, forfarande for deras framstellning och farmaceutiska kompositioner innehallande dessa derivatInfo
- Publication number
- SE452011B SE452011B SE8204585A SE8204585A SE452011B SE 452011 B SE452011 B SE 452011B SE 8204585 A SE8204585 A SE 8204585A SE 8204585 A SE8204585 A SE 8204585A SE 452011 B SE452011 B SE 452011B
- Authority
- SE
- Sweden
- Prior art keywords
- hydrogen
- carbon atoms
- alkyl group
- formula
- acid addition
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 229950001817 alpha-ergocryptine Drugs 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- 102000003946 Prolactin Human genes 0.000 claims description 4
- 108010057464 Prolactin Proteins 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229940097325 prolactin Drugs 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 3
- 206010034010 Parkinsonism Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 230000006651 lactation Effects 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 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
- 239000005526 vasoconstrictor agent Substances 0.000 claims description 3
- 206010000599 Acromegaly Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 102000015554 Dopamine receptor Human genes 0.000 claims description 2
- 108050004812 Dopamine receptor Proteins 0.000 claims description 2
- 208000001287 Galactorrhea Diseases 0.000 claims description 2
- 206010017600 Galactorrhoea Diseases 0.000 claims description 2
- 206010058359 Hypogonadism Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 206010036832 Prolactinoma Diseases 0.000 claims description 2
- 206010039966 Senile dementia Diseases 0.000 claims description 2
- 239000000935 antidepressant agent Substances 0.000 claims description 2
- 229940005513 antidepressants Drugs 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 208000030153 prolactin-producing pituitary gland adenoma Diseases 0.000 claims description 2
- 230000004936 stimulating effect Effects 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 239000012458 free base Substances 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 230000001430 anti-depressive effect Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000000862 serotonergic effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000001540 azides Chemical class 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229960004943 ergotamine Drugs 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003727 cerebral blood flow Effects 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 230000003291 dopaminomimetic effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-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
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 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
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- SZYQPTAROQANMV-UHFFFAOYSA-N ethyl pyrazine-2-carboxylate Chemical compound CCOC(=O)C1=CN=CC=N1 SZYQPTAROQANMV-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000004153 glucose metabolism Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000010365 information processing Effects 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
- 150000002500 ions Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 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
- 239000011976 maleic acid Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000000803 paradoxical effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001007 puffing effect Effects 0.000 description 1
- RLNGGCZBYFRNSV-UHFFFAOYSA-N pyrazine-2-carbonyl azide Chemical compound [N-]=[N+]=NC(=O)C1=CN=CC=N1 RLNGGCZBYFRNSV-UHFFFAOYSA-N 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- -1 thiazolo [4,3-c] pyrazin-2-yl Chemical group 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5104/81A CH649300A5 (de) | 1981-08-07 | 1981-08-07 | Ergopeptinderivate, ihre herstellung und verwendung. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8204585D0 SE8204585D0 (sv) | 1982-08-05 |
| SE8204585L SE8204585L (sv) | 1983-02-08 |
| SE452011B true SE452011B (sv) | 1987-11-09 |
Family
ID=4287999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8204585A SE452011B (sv) | 1981-08-07 | 1982-08-05 | Ergopeptinderivat, forfarande for deras framstellning och farmaceutiska kompositioner innehallande dessa derivat |
Country Status (27)
| Country | Link |
|---|---|
| US (3) | US4542135A (en]) |
| JP (1) | JPS5843982A (en]) |
| AT (1) | AT382156B (en]) |
| AU (1) | AU558414B2 (en]) |
| BE (1) | BE894046A (en]) |
| CA (1) | CA1191802A (en]) |
| CH (1) | CH649300A5 (en]) |
| CS (1) | CS235303B2 (en]) |
| DD (2) | DD211582A5 (en]) |
| DE (1) | DE3228230A1 (en]) |
| DK (1) | DK352082A (en]) |
| ES (2) | ES8402348A1 (en]) |
| FI (1) | FI72979C (en]) |
| FR (1) | FR2511003B1 (en]) |
| GB (1) | GB2109795B (en]) |
| GR (1) | GR77262B (en]) |
| HU (2) | HU193373B (en]) |
| IE (1) | IE53647B1 (en]) |
| IL (1) | IL66471A (en]) |
| IT (1) | IT1152489B (en]) |
| MY (1) | MY8600311A (en]) |
| NL (1) | NL8203067A (en]) |
| NZ (1) | NZ201504A (en]) |
| PH (1) | PH22998A (en]) |
| PT (1) | PT75384B (en]) |
| SE (1) | SE452011B (en]) |
| ZA (1) | ZA825727B (en]) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH649300A5 (de) * | 1981-08-07 | 1985-05-15 | Sandoz Ag | Ergopeptinderivate, ihre herstellung und verwendung. |
| JPS60104129A (ja) * | 1983-11-11 | 1985-06-08 | Hitachi Ltd | フッ素含有ポリアミド酸誘導体及びポリイミドの製造方法 |
| NL8600161A (nl) * | 1985-02-05 | 1986-09-01 | Sandoz Ag | Farmaceutische preparaten die 9,10-dihydroergotalkaloiden bevatten. |
| HU193317B (en) * | 1985-06-12 | 1987-09-28 | Richter Gedeon Vegyeszet | Process for producing 2-bromo-alpha-ergochristin |
| PT628042E (pt) * | 1992-12-24 | 2002-01-30 | Pharmacia & Upjohn Spa | Derivados de ergolina serotoninergicos |
| DE10041478A1 (de) | 2000-08-24 | 2002-03-14 | Sanol Arznei Schwarz Gmbh | Neue pharmazeutische Zusammensetzung |
| DE10334187A1 (de) * | 2003-07-26 | 2005-03-03 | Schwarz Pharma Ag | Substituierte 2-Aminotetraline zur Behandlung von Depressionen |
| DE10334188B4 (de) * | 2003-07-26 | 2007-07-05 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung von Depressionen |
| DE10361258A1 (de) * | 2003-12-24 | 2005-07-28 | Schwarz Pharma Ag | Verwendung von substituierten 2-Aminotetralinen zur vorbeugenden Behandlung von Morbus Parkinson |
| US20050197385A1 (en) * | 2004-02-20 | 2005-09-08 | Schwarz Pharma Ag | Use of rotigotine for treatment or prevention of dopaminergic neuron loss |
| DE102004014841B4 (de) * | 2004-03-24 | 2006-07-06 | Schwarz Pharma Ag | Verwendung von Rotigotin zur Behandlung und Prävention des Parkinson-Plus-Syndroms |
| US20070022720A1 (en) * | 2005-07-27 | 2007-02-01 | The Toro Company | Cleaner for cooling system screen of outdoor power equipment unit |
| WO2011079313A1 (en) * | 2009-12-23 | 2011-06-30 | Map Pharmaceuticals, Inc. | Novel ergoline analogs |
| US8604035B2 (en) | 2011-06-23 | 2013-12-10 | Map Pharmaceuticals, Inc. | Fluoroergoline analogs |
| SG10201509139QA (en) | 2011-12-19 | 2015-12-30 | Map Pharmaceuticals Inc | Novel iso-ergoline derivatives |
| EP2793583A4 (en) | 2011-12-21 | 2015-08-12 | Map Pharmaceuticals Inc | NOVEL NEUROMODULATORY CONNECTIONS |
| US9012640B2 (en) | 2012-06-22 | 2015-04-21 | Map Pharmaceuticals, Inc. | Cabergoline derivatives |
| CZ2013590A3 (cs) * | 2013-07-25 | 2014-09-03 | Teva Czech Industries S.R.O. | Izolovaný kmen houby Claviceps purpurea (Fr.) Tul., CCM 8404 |
| CN113308442B (zh) * | 2021-04-28 | 2023-06-27 | 天津大学 | 重组酿酒酵母菌株及其构建方法 |
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| US3314959A (en) * | 1961-05-10 | 1967-04-18 | Sandoz Ltd | Intermediates for the synthesis of ergot alkaloids |
| FR2292M (fr) * | 1962-06-27 | 1964-01-27 | Sandoz Sa | Médicament a base d'une combinaison de dihydro-ergotamine, de caféine et d'une hydantoine. |
| CH602766A5 (en) * | 1974-09-27 | 1978-07-31 | Sandoz Ag | 10-Alpha-methoxy-di:hydro-beta-ergosine derivs. |
| CH602765A5 (en]) * | 1974-09-27 | 1978-07-31 | Sandoz Ag | |
| DE2750090A1 (de) * | 1976-11-19 | 1978-06-01 | Sandoz Ag | Neue verabreichungsformen fuer organische verbindungen |
| CH626373A5 (en]) * | 1977-02-22 | 1981-11-13 | Sandoz Ag | |
| GB1584464A (en) * | 1977-04-19 | 1981-02-11 | Farmaceutici Italia | Ergot alkaloids |
| DE2717953A1 (de) * | 1977-04-22 | 1978-10-26 | Sandoz Ag | Neue therapeutische mischung und verfahren zu deren herstellung |
| YU216177A (en) * | 1977-09-09 | 1984-02-29 | Rudolf Rucman | Process for preparing 2-bromo ergosine |
| CH636011A5 (en) * | 1978-01-01 | 1983-05-13 | Sandoz Ag | Administration forms for organic compounds |
| DE2962303D1 (en) * | 1978-01-20 | 1982-04-29 | Sandoz Ag | Derivatives of ergopeptide alkaloids, process for their preparation and pharmaceutical compositions containing them |
| DE2803543A1 (de) * | 1978-01-27 | 1979-08-02 | Sandoz Ag | Ergopeptidalkaloidderivate, ihre verwendung und herstellung |
| YU40046B (en) * | 1978-09-04 | 1985-06-30 | Lek Tovarna Farmacevtskih | Process for preparing 2-bromo-9,10-dihydroergosine |
| US4609731A (en) * | 1979-10-10 | 1986-09-02 | Sandoz Ltd. | Process for brominating ergot alkaloids |
| DD200571A1 (de) * | 1981-07-22 | 1983-05-18 | Alfred Baumert | Verfahren zur herstellung von ergopeptinen mit modifiziertem prolinteil |
| CH649300A5 (de) * | 1981-08-07 | 1985-05-15 | Sandoz Ag | Ergopeptinderivate, ihre herstellung und verwendung. |
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1981
- 1981-08-07 CH CH5104/81A patent/CH649300A5/de not_active IP Right Cessation
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1982
- 1982-07-28 DE DE19823228230 patent/DE3228230A1/de not_active Ceased
- 1982-07-30 FI FI822670A patent/FI72979C/fi not_active IP Right Cessation
- 1982-08-02 NL NL8203067A patent/NL8203067A/nl not_active Application Discontinuation
- 1982-08-03 US US06/404,832 patent/US4542135A/en not_active Expired - Fee Related
- 1982-08-04 GB GB08222490A patent/GB2109795B/en not_active Expired
- 1982-08-05 SE SE8204585A patent/SE452011B/sv not_active IP Right Cessation
- 1982-08-05 AU AU86785/82A patent/AU558414B2/en not_active Ceased
- 1982-08-05 JP JP57137147A patent/JPS5843982A/ja active Granted
- 1982-08-05 FR FR8213834A patent/FR2511003B1/fr not_active Expired
- 1982-08-05 NZ NZ201504A patent/NZ201504A/en unknown
- 1982-08-05 IL IL66471A patent/IL66471A/xx unknown
- 1982-08-05 PT PT75384A patent/PT75384B/pt unknown
- 1982-08-05 ES ES514766A patent/ES8402348A1/es not_active Expired
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- 1982-08-05 DK DK352082A patent/DK352082A/da not_active Application Discontinuation
- 1982-08-06 IT IT22768/82A patent/IT1152489B/it active
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- 1982-08-06 DD DD82256213A patent/DD211582A5/de unknown
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- 1982-08-06 HU HU822537A patent/HU190405B/hu not_active IP Right Cessation
- 1982-08-06 PH PH27690A patent/PH22998A/en unknown
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- 1982-08-06 AT AT0302682A patent/AT382156B/de not_active IP Right Cessation
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1983
- 1983-09-29 ES ES526119A patent/ES526119A0/es active Granted
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1985
- 1985-07-02 US US06/751,272 patent/US4681880A/en not_active Expired - Fee Related
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1986
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1987
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