CH520681A - Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide - Google Patents
Verfahren zur Herstellung neuer MutterkornpeptidalkaloideInfo
- Publication number
- CH520681A CH520681A CH1936270A CH1936270A CH520681A CH 520681 A CH520681 A CH 520681A CH 1936270 A CH1936270 A CH 1936270A CH 1936270 A CH1936270 A CH 1936270A CH 520681 A CH520681 A CH 520681A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethyl
- general formula
- acid
- compounds
- dioxo
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 40
- -1 alkali metal amides Chemical class 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 230000001419 dependent effect Effects 0.000 claims description 5
- 230000011987 methylation Effects 0.000 claims description 3
- 238000007069 methylation reaction Methods 0.000 claims description 3
- 239000011877 solvent mixture Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- 229930015720 peptide alkaloid Natural products 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 94
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000284 extract Substances 0.000 abstract description 3
- ORBSYPFBZQJNJE-MPKXVKKWSA-N (6ar,9r,10ar)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carboxylic acid Chemical compound C1=CC([C@H]2C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ORBSYPFBZQJNJE-MPKXVKKWSA-N 0.000 abstract 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 230000002908 adrenolytic effect Effects 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 230000000794 anti-serotonin Effects 0.000 abstract 1
- 239000003420 antiserotonin agent Substances 0.000 abstract 1
- 239000012267 brine Substances 0.000 abstract 1
- 229910052593 corundum Inorganic materials 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 abstract 1
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- UNEBJJHVFQWTSI-UHFFFAOYSA-N 2-ethoxycarbonyl-2-phenylmethoxybutanoic acid Chemical compound C(C)OC(C(C(=O)O)(OCC1=CC=CC=C1)CC)=O UNEBJJHVFQWTSI-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- XHDFBEYQTOGJLR-UHFFFAOYSA-N diethyl 2-ethyl-2-phenylmethoxypropanedioate Chemical compound CCOC(=O)C(CC)(OCC1=CC=CC=C1)C(=O)OCC XHDFBEYQTOGJLR-UHFFFAOYSA-N 0.000 description 7
- QSLLFYVBWXWUQT-UHFFFAOYSA-N 7-Azaindolizine Chemical compound C1=NC=CN2C=CC=C21 QSLLFYVBWXWUQT-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 235000019445 benzyl alcohol Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 229940093915 gynecological organic acid Drugs 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- XWTYUTWHTOOWSS-WTDBAMAISA-N Ergonine Chemical compound CC[C@@]1(NC(=O)[C@H]2CN(C)C3CC4=CNC5=CC=CC(=C45)C3=C2)O[C@@]2(O)C3CCCN3C(=O)[C@H](C(C)C)N2C1=O XWTYUTWHTOOWSS-WTDBAMAISA-N 0.000 description 4
- XWTYUTWHTOOWSS-MWBPXRJMSA-N Ergonine Natural products O=C(N[C@@]1(CC)C(=O)N2[C@H](C(C)C)C(=O)N3[C@@H]([C@]2(O)O1)CCC3)[C@@H]1C=C2[C@H](N(C)C1)Cc1c3c([nH]c1)cccc23 XWTYUTWHTOOWSS-MWBPXRJMSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000001540 azides Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 150000007530 organic bases Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- TUNQTZDLMCRIIZ-UHFFFAOYSA-N pyrrolo[1,2-a]pyrazine hydrochloride Chemical compound Cl.C1=NC=CN2C=CC=C21 TUNQTZDLMCRIIZ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- RPKOYZRTFDKLRF-QPAOKJHLSA-N benzyl N-[(1S,2S,4R,7S)-4-ethyl-2-hydroxy-5,8-dioxo-7-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]carbamate Chemical compound C(C1=CC=CC=C1)OC(N[C@]1(C(N2[C@]([C@H]3N(C([C@@H]2C(C)C)=O)CCC3)(O1)O)=O)CC)=O RPKOYZRTFDKLRF-QPAOKJHLSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 3
- BHGHHZIMRWHYEO-UHFFFAOYSA-N diethyl 2-ethyl-2-hydroxypropanedioate Chemical compound CCOC(=O)C(O)(CC)C(=O)OCC BHGHHZIMRWHYEO-UHFFFAOYSA-N 0.000 description 3
- YNLVMCVYVLXNGG-UHFFFAOYSA-N diethyl 2-phenylmethoxypropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)OCC1=CC=CC=C1 YNLVMCVYVLXNGG-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 238000006748 scratching Methods 0.000 description 3
- 230000002393 scratching effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FXHKTXNWXVKCCJ-BWTUWSSMSA-N (6ar,9r)-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl chloride;hydrochloride Chemical compound Cl.C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(Cl)=O)=C3C2=CNC3=C1 FXHKTXNWXVKCCJ-BWTUWSSMSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000006418 Brown reaction Methods 0.000 description 2
- BGBHIGFGNMMHSB-JRSMBCBASA-N CC[C@@](C(N1[C@@H](CC(C)C)C(N2[C@H]3CCC2)=O)=O)(NC(OCC2=CC=CC=C2)=O)O[C@]13O Chemical compound CC[C@@](C(N1[C@@H](CC(C)C)C(N2[C@H]3CCC2)=O)=O)(NC(OCC2=CC=CC=C2)=O)O[C@]13O BGBHIGFGNMMHSB-JRSMBCBASA-N 0.000 description 2
- DQYNRDTZLGYFGF-CHPZLBCBSA-N CC[C@](C(Cl)=O)(C(N1[C@@H](C(C)C)C(N2[C@H]3CCC2)=O)=O)O[C@]13O Chemical compound CC[C@](C(Cl)=O)(C(N1[C@@H](C(C)C)C(N2[C@H]3CCC2)=O)=O)O[C@]13O DQYNRDTZLGYFGF-CHPZLBCBSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JFRCRHHCXKEHBW-UHFFFAOYSA-N Ergoptin Natural products O1C2(O)C3CCCN3C(=O)C(CC(C)C)N2C(=O)C1(CC)NC(=O)C(CN(C)C1C2)C=C1C1=C3C2=CNC3=CC=C1 JFRCRHHCXKEHBW-UHFFFAOYSA-N 0.000 description 2
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical class CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- JFRCRHHCXKEHBW-YKAZNSBZSA-N ergoptin Chemical compound C([C@H]1[C@]2(O)O3)CCN1C(=O)[C@@H](CC(C)C)N2C(=O)[C@]3(CC)NC(=O)[C@@H](CN(C)[C@@H]1C2)C=C1C1=C3C2=CNC3=CC=C1 JFRCRHHCXKEHBW-YKAZNSBZSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 229960003975 potassium Drugs 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 230000000707 stereoselective effect Effects 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- VUICQSAEJDXUEH-UHFFFAOYSA-N 2-ethyl-2-phenylmethoxypropanedioic acid Chemical compound C(C)C(C(=O)O)(C(=O)O)OCC1=CC=CC=C1 VUICQSAEJDXUEH-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- GXWNSJYVSIJRLS-UHFFFAOYSA-N 6-bromo-8-methylimidazo[1,2-a]pyrazine Chemical compound CC1=NC(Br)=CN2C=CN=C12 GXWNSJYVSIJRLS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000005574 benzylation reaction Methods 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- XLUAWXQORJEMBD-YUMQZZPRSA-N cyclo(L-Pro-L-Val) Chemical compound O=C1[C@H](C(C)C)NC(=O)[C@@H]2CCCN21 XLUAWXQORJEMBD-YUMQZZPRSA-N 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 229960003133 ergot alkaloid Drugs 0.000 description 1
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 description 1
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007788 liquid Substances 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
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
- HYHBKLWDTGTBME-UHFFFAOYSA-N pyrazin-1-ium;chloride Chemical compound Cl.C1=CN=CC=N1 HYHBKLWDTGTBME-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1936270A CH520681A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1090067A CH520679A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
| CH1936270A CH520681A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH520681A true CH520681A (de) | 1972-03-31 |
Family
ID=4368003
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1936270A CH520681A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
| CH1090067A CH520679A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
| CH1090067A CH563393A5 (en) | 1967-08-02 | 1967-08-02 | Ergot derivs andrenolytics |
| CH1936170A CH520680A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1090067A CH520679A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
| CH1090067A CH563393A5 (en) | 1967-08-02 | 1967-08-02 | Ergot derivs andrenolytics |
| CH1936170A CH520680A (de) | 1967-08-02 | 1967-08-02 | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3652569A (en, 2012) |
| AT (1) | AT297008B (en, 2012) |
| BE (1) | BE718859A (en, 2012) |
| CA (1) | CA952107A (en, 2012) |
| CH (4) | CH520681A (en, 2012) |
| CY (1) | CY769A (en, 2012) |
| DE (1) | DE1795022C3 (en, 2012) |
| DK (1) | DK123482B (en, 2012) |
| ES (5) | ES356676A1 (en, 2012) |
| FI (1) | FI48274C (en, 2012) |
| FR (2) | FR1604602A (en, 2012) |
| GB (2) | GB1240420A (en, 2012) |
| MY (1) | MY7400292A (en, 2012) |
| NL (1) | NL157906B (en, 2012) |
| PL (2) | PL78658B1 (en, 2012) |
| SE (2) | SE392903B (en, 2012) |
| SU (1) | SU392624A3 (en, 2012) |
| YU (1) | YU34084B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846433A (en) * | 1969-05-06 | 1974-11-05 | Sandoz Ltd | Process for preparing ergot alkaloids |
| US4195086A (en) * | 1974-06-21 | 1980-03-25 | Sandoz Ltd. | 6-Branched chain alkyl sustituted ergot alkaloids |
| CH601321A5 (en, 2012) * | 1975-01-06 | 1978-07-14 | Sandoz Ag | |
| US4138565A (en) * | 1975-05-31 | 1979-02-06 | Sandoz Ltd. | Stable solutions and processes for their preparation |
| IT1157365B (it) * | 1977-10-24 | 1987-02-11 | Sandoz Ag | Medicamenti per trattare l'obesita' o ridurre il peso del corpo |
| YU41110B (en) * | 1978-07-19 | 1986-12-31 | Lek Tovarna Farmacevtskih | Process for preparing dextrorotatory ergot alcaloids acid addition salts |
| DE3303616A1 (de) * | 1982-02-12 | 1983-08-25 | Sandoz-Patent-GmbH, 7850 Lörrach | Mutterkornalkaloide, verfahren zu deren herstellung sowie diese verbindungen enthaltende pharmazeutische zubereitungen |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| 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 |
| WO2013095707A1 (en) | 2011-12-19 | 2013-06-27 | 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 |
-
1967
- 1967-08-02 CH CH1936270A patent/CH520681A/de not_active IP Right Cessation
- 1967-08-02 CH CH1090067A patent/CH520679A/de not_active IP Right Cessation
- 1967-08-02 CH CH1090067A patent/CH563393A5/xx not_active IP Right Cessation
- 1967-08-02 CH CH1936170A patent/CH520680A/de not_active IP Right Cessation
-
1968
- 1968-07-17 GB GB56746/70A patent/GB1240420A/en not_active Expired
- 1968-07-17 GB GB1238348D patent/GB1238348A/en not_active Expired
- 1968-07-23 NL NL6810435.A patent/NL157906B/xx not_active IP Right Cessation
- 1968-07-26 FI FI682123A patent/FI48274C/fi active
- 1968-07-26 DK DK362968AA patent/DK123482B/da unknown
- 1968-07-29 SE SE7112754A patent/SE392903B/xx unknown
- 1968-07-29 SE SE10291/68A patent/SE351643B/xx unknown
- 1968-07-30 DE DE1795022A patent/DE1795022C3/de not_active Expired
- 1968-07-31 ES ES356676A patent/ES356676A1/es not_active Expired
- 1968-07-31 AT AT745768A patent/AT297008B/de not_active IP Right Cessation
- 1968-07-31 PL PL1968158941A patent/PL78658B1/pl unknown
- 1968-07-31 PL PL1968128394A patent/PL72567B1/pl unknown
- 1968-07-31 CA CA026,340A patent/CA952107A/en not_active Expired
- 1968-07-31 BE BE718859D patent/BE718859A/xx unknown
- 1968-08-01 FR FR1604602D patent/FR1604602A/fr not_active Expired
- 1968-08-01 SU SU1370603A patent/SU392624A3/ru active
- 1968-08-01 YU YU1839/68A patent/YU34084B/xx unknown
- 1968-10-29 FR FR171753A patent/FR8150M/fr not_active Expired
-
1969
- 1969-09-12 ES ES371455A patent/ES371455A1/es not_active Expired
- 1969-09-12 ES ES371452A patent/ES371452A1/es not_active Expired
- 1969-09-12 ES ES371454A patent/ES371454A1/es not_active Expired
- 1969-09-12 ES ES371453A patent/ES371453A1/es not_active Expired
-
1971
- 1971-01-21 US US108641A patent/US3652569A/en not_active Expired - Lifetime
-
1974
- 1974-11-08 CY CY76974A patent/CY769A/xx unknown
- 1974-12-30 MY MY292/74A patent/MY7400292A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR8150M (en, 2012) | 1970-08-17 |
| DE1795022A1 (de) | 1971-12-30 |
| ES371454A1 (es) | 1972-03-16 |
| DK123482B (da) | 1972-06-26 |
| SE392903B (sv) | 1977-04-25 |
| FI48274C (fi) | 1974-08-12 |
| CA952107A (en) | 1974-07-30 |
| YU34084B (en) | 1978-12-31 |
| CH520680A (de) | 1972-03-31 |
| GB1240420A (en) | 1971-07-21 |
| MY7400292A (en) | 1974-12-31 |
| DE1795022C3 (de) | 1981-06-19 |
| AT297008B (de) | 1972-03-10 |
| GB1238348A (en, 2012) | 1971-07-07 |
| ES371452A1 (es) | 1972-03-16 |
| PL78658B1 (en, 2012) | 1975-06-30 |
| NL6810435A (en, 2012) | 1969-02-04 |
| ES371453A1 (es) | 1972-03-16 |
| ES371455A1 (es) | 1972-04-01 |
| YU183968A (en) | 1978-06-30 |
| CH563393A5 (en) | 1975-06-30 |
| FI48274B (en, 2012) | 1974-04-30 |
| FR1604602A (en, 2012) | 1972-01-03 |
| CH520679A (de) | 1972-03-31 |
| NL157906B (nl) | 1978-09-15 |
| BE718859A (en, 2012) | 1969-01-31 |
| SU392624A3 (en, 2012) | 1973-07-27 |
| PL72567B1 (en, 2012) | 1974-08-30 |
| US3652569A (en) | 1972-03-28 |
| DE1795022B2 (en, 2012) | 1980-08-07 |
| SE351643B (en, 2012) | 1972-12-04 |
| ES356676A1 (es) | 1970-05-01 |
| CY769A (en) | 1974-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2901181C2 (de) | N-(1-Alkyl- bzw. Allyl-2-pyrrolidinylmethyl)-2-methoxy-4-amino-5-alkylsulfonylbenzamide, deren Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| CH520681A (de) | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide | |
| EP0271795A2 (de) | Octahydro-10-oxo-6H-pyridazo [1,2-a] [1,2] diazepin-Derivate, Zwischenprodukte und Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel | |
| DE2851028A1 (de) | Neue indolo eckige klammer auf 2.3-a eckige klammer zu chinolizidine, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitung | |
| DE69318563T2 (de) | 5H,10H-IMIDAZO[1,2-a]INDENO[1,2-e]PYRAZIN-4-ONE DERIVATE, IHRE HERSTELLUNG UND DIE SIE ENTHALTENDEN ARZNEIMITTEL | |
| DE2118261A1 (de) | Neue N-haltige Bicyclen, deren Säureadditionssalze sowie Verfahren zu deren Herstellung | |
| CH649295A5 (de) | Optisch aktive oder razemische brom-e-homo-eburanderivate. | |
| EP0266308B1 (de) | Indolo-pyrazino-benzodiazepin-Derivate | |
| EP0003286B1 (de) | Ergopeptidalkaloid-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| CH610330A5 (en) | Process for the preparation of novel ergopeptins | |
| DE69426581T2 (de) | Isatinoxim-Derivate, ihre Herstellung und Verwendung | |
| DE2259471C2 (de) | 2-Halogen-9-phenyl-5,6-dihydro-7H-pyrido [2,3-f] [1,4] diazepinderivate | |
| CH494762A (de) | Verfahren zur Herstellung neuer Mutterkornpeptidalkaloide | |
| DE2540334C2 (de) | Benzylaminoalkansäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen | |
| DE2122070A1 (de) | 1 Veratryl 4 methyl 5 athyl 7,8 dimethoxy 2,3 diazabicyclo eckige Klam mer auf 5,4,0 eckige Klammer zu undeca pentaen (1,3,6,8,10) und seine Verwendung | |
| WO1983002775A1 (en) | Ergot alkaloids, manufacturing process thereof and pharmaceutical preparations containing them | |
| DE3813416A1 (de) | 3,4-dihydroxypyrrolidin-2-on-derivate, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte | |
| CH658656A5 (de) | Neue eburnamenin-14-carbonsaeure-derivate, verfahren zu ihrer herstellung und die neuen verbindungen enthaltende arzneimittelpraeparate. | |
| EP0056616B1 (de) | Cycloheptenderivate, Verfahren zu ihrer Herstellung, sowie diese enthaltende Arzneimittel | |
| DE2710807C2 (de) | Benzylamino-alkancarboxamide, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1904585C3 (de) | Ester der 7-(a-Amino-a- phenylacetamido)cephalosporansaure und ihre Herstellung | |
| CH518932A (de) | Verfahren zur Herstellung neuer Guanidin-Derivate | |
| CH561724A5 (en) | Ergot derivs andrenolytics | |
| CH550801A (de) | Verfahren zur herstellung heterocyclischer verbindungen. | |
| CH541564A (de) | Verfahren zur Herstellung von bisher unbekannten heterocyclischen Verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |