DD148517A5 - Verfahren zur herstellung von 6-oxodecahydrochinolinen - Google Patents
Verfahren zur herstellung von 6-oxodecahydrochinolinen Download PDFInfo
- Publication number
- DD148517A5 DD148517A5 DD79218310A DD21831079A DD148517A5 DD 148517 A5 DD148517 A5 DD 148517A5 DD 79218310 A DD79218310 A DD 79218310A DD 21831079 A DD21831079 A DD 21831079A DD 148517 A5 DD148517 A5 DD 148517A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- mixture
- preparation
- ethoxycarbonyl
- cooz
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 229940117975 chromium trioxide Drugs 0.000 claims abstract description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims abstract description 5
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- QFTAAIXFZNESMI-UHFFFAOYSA-N 2,3,4,4a,5,7,8,8a-octahydro-1h-quinolin-6-one Chemical class N1CCCC2CC(=O)CCC21 QFTAAIXFZNESMI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 2
- QMQARUHERXCTNJ-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinolin-6-ol Chemical class N1CCCC2CC(O)CCC21 QMQARUHERXCTNJ-UHFFFAOYSA-N 0.000 abstract 1
- 101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
- 239000000391 magnesium silicate Substances 0.000 description 2
- 229910052919 magnesium silicate Inorganic materials 0.000 description 2
- 235000019792 magnesium silicate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 2
- VFICJPDIBDJAGL-UHFFFAOYSA-N (4-oxocyclohexyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCC(=O)CC1 VFICJPDIBDJAGL-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WCGXSRQZZSJEBP-UHFFFAOYSA-N ethyl 6-benzoyloxy-1-propyl-3,4,5,6,7,8-hexahydro-2h-quinoline-3-carboxylate Chemical compound CCCN1CC(C(=O)OCC)CC(C2)=C1CCC2OC(=O)C1=CC=CC=C1 WCGXSRQZZSJEBP-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- -1 p-methoxybenzyl Chemical group 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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 to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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 to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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 to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US506179A | 1979-01-22 | 1979-01-22 | |
| US06/031,641 US4198415A (en) | 1979-01-22 | 1979-04-19 | Prolactin inhibiting octahydro pyrazolo[3,4-g]quinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD148517A5 true DD148517A5 (de) | 1981-05-27 |
Family
ID=26673868
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79218311A DD148518A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von octahydropyrazolo eckige klammer auf 3,4-g eckige klammer zu chinolinen |
| DD79218313A DD148340A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von 6-oxo-7-(dimethylaminomethylen)decahydrochinolinen |
| DD79213992A DD144670A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von octahydropyrazolo eckige klammer auf 3,4-g eckige klammer zu chinolinen |
| DD79218312A DD148339A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von 6-hydroxydecahydrochinolinen |
| DD79218310A DD148517A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von 6-oxodecahydrochinolinen |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD79218311A DD148518A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von octahydropyrazolo eckige klammer auf 3,4-g eckige klammer zu chinolinen |
| DD79218313A DD148340A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von 6-oxo-7-(dimethylaminomethylen)decahydrochinolinen |
| DD79213992A DD144670A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von octahydropyrazolo eckige klammer auf 3,4-g eckige klammer zu chinolinen |
| DD79218312A DD148339A5 (de) | 1979-01-22 | 1979-06-29 | Verfahren zur herstellung von 6-hydroxydecahydrochinolinen |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4198415A (enExample) |
| EP (2) | EP0013787B1 (enExample) |
| AT (1) | AT371819B (enExample) |
| AU (1) | AU528076B2 (enExample) |
| CA (1) | CA1136140A (enExample) |
| CH (3) | CH644377A5 (enExample) |
| DD (5) | DD148518A5 (enExample) |
| DE (2) | DE2966945D1 (enExample) |
| DK (1) | DK268879A (enExample) |
| EG (1) | EG14696A (enExample) |
| ES (4) | ES482089A1 (enExample) |
| FI (1) | FI65247C (enExample) |
| FR (5) | FR2446832A1 (enExample) |
| GB (4) | GB2092580B (enExample) |
| GR (1) | GR72516B (enExample) |
| IE (1) | IE48394B1 (enExample) |
| IL (1) | IL57668A (enExample) |
| LU (1) | LU81439A1 (enExample) |
| MY (1) | MY8500683A (enExample) |
| NZ (2) | NZ201279A (enExample) |
| PH (3) | PH14909A (enExample) |
| PL (4) | PL122153B1 (enExample) |
| PT (1) | PT69829A (enExample) |
| RO (2) | RO82159A (enExample) |
| ZA (1) | ZA793243B (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL65269A0 (en) * | 1981-03-24 | 1982-05-31 | Lilly Co Eli | 6-substituted hexahydroindazolo or hexahydroisoindolo isoquinolines |
| US4540787A (en) * | 1982-06-03 | 1985-09-10 | Eli Lilly And Company | Method of preparing trans-D1-1-alkyl-6-oxodecahydroquinolines |
| US4471121A (en) * | 1982-11-03 | 1984-09-11 | Eli Lilly And Company | Method of resolving trans-d alpha-1-n-propyl-6-oxodecahydroquinoline and di-p-toluoyltartaric acid salts thereof |
| US4567266A (en) * | 1982-11-03 | 1986-01-28 | Eli Lilly And Company | Method of preparing octahydro-1H(and 2H)-pyrazolo[3,4-g]quinolines |
| US4468401A (en) * | 1982-11-03 | 1984-08-28 | Eli Lilly And Company | Method of blocking peripheral norepinephrine release |
| US4647667A (en) * | 1982-11-03 | 1987-03-03 | Eli Lilly And Company | Octa- and deca-hydroquinoline intermediates |
| ES524452A0 (es) * | 1982-11-03 | 1985-04-16 | Lilly Co Eli | Un procedimiento para la preparacion de derivados de pirazolo-quinolinas. |
| DE3373468D1 (de) * | 1983-06-03 | 1987-10-15 | Lilly Co Eli | Trans-dl-1-alkyl-6-alkoxyoctahydroquinolines |
| US4626591A (en) * | 1983-08-10 | 1986-12-02 | Eli Lilly And Company | Trans-dl-1-alkyl-6-alkoxy-1,2,3,4,4a,5,8,8a octa-hydroquinolines |
| US4528290A (en) * | 1984-01-30 | 1985-07-09 | Eli Lilly And Company | Stimulating dopamine D-1 receptors |
| US4501890A (en) * | 1983-09-26 | 1985-02-26 | Eli Lilly And Company | Trans-(±)-2,4,6-substituted-5,5a,6,7,8,9,9a,10-octahydro-pyrimido[4,5-g]quinolines |
| IL73001A0 (en) * | 1983-09-26 | 1984-12-31 | Lilly Co Eli | Improvements in and relating to 6-oxodecahydroquinolines |
| US4521421A (en) * | 1983-09-26 | 1985-06-04 | Eli Lilly And Company | Treatment of sexual dysfunction |
| US4507478A (en) * | 1983-09-26 | 1985-03-26 | Eli Lilly And Company | 2-Mercaptopyrimidohexahydroquinolines and related compounds |
| FI78091C (fi) * | 1983-09-26 | 1989-06-12 | Lilly Co Eli | Analogifoerfarande foer framstaellning av saosom dopaminoagonister anvaendbara pyrimido/4,5-g/kinolinderivat. |
| CA1270488A (en) * | 1983-09-26 | 1990-06-19 | John M. Schaus | Pyrazole-ring alkylated pyrazoloquinolines and intermediates |
| US4587351A (en) * | 1984-04-18 | 1986-05-06 | Eli Lilly And Company | Synthesis of ketones with calcium hypochlorite |
| US4689415A (en) * | 1984-04-18 | 1987-08-25 | Eli Lilly And Company | Trans octahydroquinoline intermediate |
| US4537893A (en) * | 1984-04-27 | 1985-08-27 | Eli Lilly And Company | Octahydrothiazolo[4,5-g]quinolines and use as prolactin secretion inhibitors |
| IE58695B1 (en) * | 1984-08-02 | 1993-11-03 | Lilly Co Eli | Octahydro-oxazolo [4,5-g] quinolines |
| US4600777A (en) * | 1984-08-02 | 1986-07-15 | Eli Lilly And Company | Method of preparing 1-alkyl-7-oxodecahydroquinolines, and cis(±) and tran(±)isomers so prepared |
| US4537965A (en) * | 1984-08-03 | 1985-08-27 | Eli Lilly And Company | Method of preparing 4aR,8aR-5-permissibly substituted-6-oxo-octahydro-1H(and 2H)-pyrazolo[3,4-g]quinolines, useful as intermediates |
| US4537964A (en) * | 1984-08-03 | 1985-08-27 | Eli Lilly And Company | Method of preparing permissibly-substituted 1H(and 2H)pyrazolo[3,4-g]quinolines; pyrimido[4,5,g]quinolines; thiazolo[4,5,g]quinolines and intermediates therefore |
| DK349385A (da) * | 1984-08-03 | 1986-02-04 | Lilly Co Eli | Fremgangsmaade til fremstilling af tricycliske quinolin-derivater og mellemprodukt til brug ved fremgangsmaaden |
| US4552956A (en) * | 1984-08-15 | 1985-11-12 | Eli Lilly And Company | Partially hydrogenated pyrazolo, pyrimido and thiazolo[1,4]benzoxazines |
| US4587336A (en) * | 1984-08-15 | 1986-05-06 | Eli Lilly And Company | Partially hydrogenated intermediate pyrazolo, pyrimido and thiazolo[1,4]benzoxazines |
| FR2578254B1 (fr) * | 1985-03-01 | 1987-03-06 | Roussel Uclaf | Nouveaux derives de la pyrazolobenzoxazine, leurs sels, procede de preparation, application a titre de medicaments, compositions les renfermant, et des intermediaires |
| US4595754A (en) * | 1985-03-04 | 1986-06-17 | Eli Lilly And Company | Process for preparing cis N-alkylperhydroquinolines |
| US4927828A (en) * | 1985-03-08 | 1990-05-22 | The Trustees Of Princeton University | Diastereoisomeric tetrahydropyrido-(2,3,d) pyrimidine derivatives |
| US4622398A (en) * | 1985-06-24 | 1986-11-11 | Eli Lilly And Company | Dialkylaminotetrahydroquinazoline |
| US5134143A (en) * | 1986-06-16 | 1992-07-28 | Eli Lilly And Company | BCD tricyclic ergoline part-structure analogues |
| US4977160A (en) * | 1986-06-16 | 1990-12-11 | Eli Lilly And Company | BCD tricyclic ergoline part-structure analogues |
| US4826986A (en) * | 1986-06-16 | 1989-05-02 | Eli Lilly And Company | 6-Oxo-trans-octa- and decahydroquinolines |
| US4762843A (en) * | 1986-09-15 | 1988-08-09 | Warner-Lambert Company | Hetero [f] fused carbocyclic pyridines as dopaminergic agents |
| US4939259A (en) * | 1989-07-24 | 1990-07-03 | Eli Lilly And Company | 2-oxo-pyrido[2,3-g]quinoline derivatives |
| US4977149A (en) * | 1989-07-24 | 1990-12-11 | Eli Lilly And Company | Pyridoquinoline dopamine agonists, compositions and use |
| US5006525A (en) * | 1989-07-24 | 1991-04-09 | Eli Lilly And Company | Dopamine agonists method |
| US5057515A (en) * | 1989-07-24 | 1991-10-15 | Eli Lilly And Company | Method for agonizing a dopamine receptor |
| ES2071334T3 (es) * | 1990-09-28 | 1995-06-16 | Pfizer | Analogos de anillos fusionados de nitrogeno conteniendo heterociclos no aromaticos. |
| US5416090A (en) * | 1991-01-31 | 1995-05-16 | Eli Lilly And Company | Method of treating inflammation |
| US20030212085A1 (en) * | 2001-04-17 | 2003-11-13 | Mccall Robert B. | Treatment of fibromyalgia and chronic fatigue syndrome |
| MY148644A (en) * | 2005-07-18 | 2013-05-15 | Orion Corp | New pharmaceutical compounds |
| US11884672B2 (en) | 2019-05-14 | 2024-01-30 | Vertex Pharmaceuticals Incorporated | Modulators of alpha-1 antitrypsin |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3084165A (en) * | 1959-05-21 | 1963-04-02 | Bayer Ag | Quinone derivatives and processes for producing the same |
| US3600393A (en) * | 1969-03-03 | 1971-08-17 | Aldrich Chem Co Inc | Dialkylamino alkylamino pyrazolo (3,4b) quinolines |
| US3859291A (en) * | 1973-10-01 | 1975-01-07 | Morton Norwich Products Inc | 9-(p-anisidino)-7-methyl-(1h)-pyrazolo(3,4-f)quinoline |
| US4028381A (en) * | 1975-05-05 | 1977-06-07 | Ciba-Geigy Corporation | Pyrazolobenzazepines |
-
1979
- 1979-04-19 US US06/031,641 patent/US4198415A/en not_active Expired - Lifetime
- 1979-06-26 PT PT69829A patent/PT69829A/pt unknown
- 1979-06-26 CA CA000330552A patent/CA1136140A/en not_active Expired
- 1979-06-26 NZ NZ201279A patent/NZ201279A/en unknown
- 1979-06-26 IL IL57668A patent/IL57668A/xx unknown
- 1979-06-26 NZ NZ190835A patent/NZ190835A/en unknown
- 1979-06-26 DK DK268879A patent/DK268879A/da not_active Application Discontinuation
- 1979-06-27 FR FR7916571A patent/FR2446832A1/fr active Granted
- 1979-06-27 LU LU81439A patent/LU81439A1/xx unknown
- 1979-06-27 RO RO79104044A patent/RO82159A/ro unknown
- 1979-06-27 RO RO7997973A patent/RO77563A/ro unknown
- 1979-06-27 AU AU48445/79A patent/AU528076B2/en not_active Ceased
- 1979-06-27 PH PH22704A patent/PH14909A/en unknown
- 1979-06-28 CH CH606079A patent/CH644377A5/fr not_active IP Right Cessation
- 1979-06-28 DE DE8181110640T patent/DE2966945D1/de not_active Expired
- 1979-06-28 GR GR59466A patent/GR72516B/el unknown
- 1979-06-28 EP EP79301250A patent/EP0013787B1/en not_active Expired
- 1979-06-28 GB GB8203157A patent/GB2092580B/en not_active Expired
- 1979-06-28 DE DE7979301250T patent/DE2966951D1/de not_active Expired
- 1979-06-28 GB GB7922530A patent/GB2040915B/en not_active Expired
- 1979-06-28 EP EP81110640A patent/EP0050881B1/en not_active Expired
- 1979-06-28 GB GB8203158A patent/GB2092581A/en not_active Withdrawn
- 1979-06-28 FI FI792046A patent/FI65247C/fi not_active IP Right Cessation
- 1979-06-28 AT AT0452479A patent/AT371819B/de not_active IP Right Cessation
- 1979-06-28 GB GB8203156A patent/GB2092579A/en not_active Withdrawn
- 1979-06-29 DD DD79218311A patent/DD148518A5/de unknown
- 1979-06-29 DD DD79218313A patent/DD148340A5/de unknown
- 1979-06-29 PL PL1979216719A patent/PL122153B1/pl unknown
- 1979-06-29 ZA ZA793243A patent/ZA793243B/xx unknown
- 1979-06-29 ES ES482089A patent/ES482089A1/es not_active Expired
- 1979-06-29 ES ES482090A patent/ES482090A1/es not_active Expired
- 1979-06-29 ES ES482087A patent/ES482087A1/es not_active Expired
- 1979-06-29 DD DD79213992A patent/DD144670A5/de unknown
- 1979-06-29 PL PL1979225533A patent/PL119785B1/pl unknown
- 1979-06-29 DD DD79218312A patent/DD148339A5/de unknown
- 1979-06-29 ES ES482091A patent/ES482091A1/es not_active Expired
- 1979-06-29 PL PL1979225531A patent/PL119715B1/pl unknown
- 1979-06-29 PL PL1979225532A patent/PL120037B1/pl unknown
- 1979-06-29 DD DD79218310A patent/DD148517A5/de unknown
- 1979-06-30 EG EG393/79A patent/EG14696A/xx active
- 1979-08-08 IE IE1209/79A patent/IE48394B1/en unknown
- 1979-11-06 FR FR7927311A patent/FR2446820A1/fr active Pending
- 1979-11-06 FR FR7927310A patent/FR2446822A1/fr active Granted
- 1979-11-06 FR FR7927308A patent/FR2446834A1/fr active Granted
- 1979-11-06 FR FR7927309A patent/FR2446821A1/fr not_active Withdrawn
-
1980
- 1980-03-12 PH PH23757A patent/PH14991A/en unknown
- 1980-03-12 PH PH23756A patent/PH14908A/en unknown
-
1983
- 1983-06-20 CH CH336783A patent/CH644607A5/fr not_active IP Right Cessation
- 1983-06-20 CH CH336883A patent/CH644365A5/fr not_active IP Right Cessation
-
1985
- 1985-12-30 MY MY683/85A patent/MY8500683A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD148517A5 (de) | Verfahren zur herstellung von 6-oxodecahydrochinolinen | |
| DE2227739C2 (de) | Pseudomonsäuren, deren Natriumsalze und Methylester und Verfahren zu ihrer Herstellung | |
| DE2229223C3 (de) | 2-Nitro-S-imidazol-Derivate und Verfahren zu deren Herstellung | |
| DE2514673C2 (de) | Benzo[b]bicyclo[3.3.1]nona-3,6a(10a)diene, Verfahren zu ihrer Herstellung und diese enthaltende anorektische Mittel | |
| CH630391A5 (en) | Process for preparing derivatives of rosaramicin | |
| CH639390A5 (de) | Verfahren zur herstellung von alkaloiden vom leurosin-typ. | |
| DE2948116A1 (de) | Verfahren zur herstellung von apovincaminsaeureester-derivaten | |
| DE2757281C3 (de) | Verfahren zur Herstellung von 1 -Hydroxy-Aporphinderivaten | |
| DE2700234A1 (de) | Organische verbindungen und verfahren zu deren herstellung | |
| DE69907101T2 (de) | Neue Hydroxyderivate von Tylosin und Verfahren zu deren Herstellung | |
| DE2902292C2 (de) | Verfahren zur Herstellung von 2,4-Diaminobuttersäure oder 4-Amino-2-hydroxybuttersäure | |
| DE2338838A1 (de) | 9h-pyrido eckige klammer auf 3,4 eckige klammer zu indol-derivate, verfahren zu deren herstellung und deren verwendung | |
| EP0159640A1 (de) | 4-Methoxy-2,2'-bipyridyl-6-aldoxime, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| DE1493323B2 (de) | 1-(p-hydroxyphenyl)-2-phenyl-6methoxy- 3,4-dihydronaphthalin, dessen pharmakologisch geeignete salze und verfahren zur herstellung dieser verbindungen | |
| DE2200259C3 (de) | 1,2,3,4,6,7,12,12b-E-Octahydroindolo eckige Klammer auf 2,3a eckige Klammer zu chinolizyliden-essigsäureäthylester, Verfahren zu seiner Herstellung und seine Verwendung zur Herstellung von (+-)-Ebumamonin | |
| DE1097999B (de) | Verfahren zur Herstellung von 1, 2, 3, 4, 6, 7, 12, 12b-Octahydroindolo[2, 3-a]chinolizinen | |
| DE1804392A1 (de) | 9-0-Kalamycinderivate und Verfahren zu ihrer Herstellung | |
| DE825686C (de) | Verfahren zur UEberfuehrung von í¸-20-Cyanpregnenen mit einer oder mehreren kerngebundenen Hydroxylgruppen in 17 alpha-Oxy-20-ketopregnane | |
| DE2812569C2 (enExample) | ||
| DE1693026C3 (de) | Antibiotisch wirkende Delta hoch 13(17) - und Delta hoch 13(17);20(22) - Fusidinsäurederivate und Verfahren zu ihrer Herstellung | |
| DE1593299C (de) | Verfahren zur Herstellung von optisch aktiven Hydroxycycloalkan-3-onen | |
| DE2248793C3 (de) | Verfahren zur Herstellung von Macrolid-Antibiotika | |
| DE2707404A1 (de) | 5,6-dehydropenicilline und verfahren zu deren herstellung und mittel zur durchfuehrung des verfahrens | |
| CH683099A5 (de) | Verfahren zur Herstellung von 1-(3-Mercapto-(2S)-methyl-1-oxo-propyl)-L-prolin. | |
| AT371464B (de) | Verfahren zur herstellung von neuen trans-dl-4,4a,5,6,7,8,8a,9-octahydro-2h-pyrrolo 3,4-g)chinolin- verbindungen und ihren salzen |