DE2552563A1 - Organische verbindungen, ihre verwendung und herstellung - Google Patents
Organische verbindungen, ihre verwendung und herstellungInfo
- Publication number
- DE2552563A1 DE2552563A1 DE19752552563 DE2552563A DE2552563A1 DE 2552563 A1 DE2552563 A1 DE 2552563A1 DE 19752552563 DE19752552563 DE 19752552563 DE 2552563 A DE2552563 A DE 2552563A DE 2552563 A1 DE2552563 A1 DE 2552563A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- group
- formula
- alkyl
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims 3
- 150000002894 organic compounds Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 150000001875 compounds Chemical group 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- -1 benzylcarbonyl group Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- VLLZJYVDYDUFRT-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,2,3,3a,5,6,7,7a-octahydroindol-4-ol Chemical group C1CCC2NCCC2C1(O)C1=CC=C(Cl)C=C1 VLLZJYVDYDUFRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- CYBNYHPBDUGRPA-UHFFFAOYSA-N 4-phenyl-1,2,3,3a,5,6,7,7a-octahydroindol-4-ol Chemical group C1CCC2NCCC2C1(O)C1=CC=CC=C1 CYBNYHPBDUGRPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- XOSDCNHITZTNDJ-UHFFFAOYSA-N 4-phenyl-1-(1-phenylethyl)-3,3a,5,6,7,7a-hexahydro-2H-indol-4-ol Chemical compound C=1C=CC=CC=1C(C)N1CCC2C1CCCC2(O)C1=CC=CC=C1 XOSDCNHITZTNDJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 229910052987 metal hydride Inorganic materials 0.000 description 4
- 150000004681 metal hydrides Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-M malonate(1-) Chemical compound OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000005932 reductive alkylation reaction Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 2
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RCMLKQSZCSYLLS-UHFFFAOYSA-N 1-hydroxy-2,3-dihydroindole Chemical compound C1=CC=C2N(O)CCC2=C1 RCMLKQSZCSYLLS-UHFFFAOYSA-N 0.000 description 1
- OWWAUBQOFLVUMS-UHFFFAOYSA-N 2,3-dihydro-1h-indol-4-ol Chemical compound OC1=CC=CC2=C1CCN2 OWWAUBQOFLVUMS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FXFDJSQOCVDXBX-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane Chemical compound C1=CC(F)=CC=C1C1(CCCCl)OCCO1 FXFDJSQOCVDXBX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical group OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- CEBWQYAQWISILJ-UHFFFAOYSA-N [4-(4-chlorophenyl)-4-hydroxy-3,3a,5,6,7,7a-hexahydro-2h-indol-1-yl]-cyclopropylmethanone Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCCC2C1CCN2C(=O)C1CC1 CEBWQYAQWISILJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- WNOPHAJGNSIJTM-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-4-hydroxy-3,3a,5,6,7,7a-hexahydro-2h-indole-1-carboxylate Chemical compound CCOC(=O)N1CCC2C1CCCC2(O)C1=CC=C(Cl)C=C1 WNOPHAJGNSIJTM-UHFFFAOYSA-N 0.000 description 1
- JDMFRZCXBYJYJM-UHFFFAOYSA-N ethyl 4-hydroxy-4-phenyl-3,3a,5,6,7,7a-hexahydro-2H-indole-1-carboxylate Chemical compound CCOC(=O)N1CCC2C1CCCC2(O)C1=CC=CC=C1 JDMFRZCXBYJYJM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1623674A CH601226A5 (enrdf_load_stackoverflow) | 1974-12-06 | 1974-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2552563A1 true DE2552563A1 (de) | 1976-06-10 |
Family
ID=4415551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752552563 Withdrawn DE2552563A1 (de) | 1974-12-06 | 1975-11-24 | Organische verbindungen, ihre verwendung und herstellung |
Country Status (20)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2365557A1 (fr) * | 1976-09-22 | 1978-04-21 | Sandoz Sa | Nouveaux perhydro-indolinols, leur preparation et leur application comme medicaments |
| US4124719A (en) * | 1974-12-06 | 1978-11-07 | Sandoz Ltd. | -4-Phenylhexahydro-4-indolinol derivatives |
-
1974
- 1974-12-06 CH CH1623674A patent/CH601226A5/xx not_active IP Right Cessation
-
1975
- 1975-11-24 DE DE19752552563 patent/DE2552563A1/de not_active Withdrawn
- 1975-11-27 DK DK537175AA patent/DK140723B/da unknown
- 1975-11-27 FI FI753351A patent/FI753351A7/fi not_active Application Discontinuation
- 1975-11-28 NO NO754028A patent/NO754028L/no unknown
- 1975-11-28 SE SE7513457A patent/SE408895B/xx unknown
- 1975-12-02 NL NL7514007A patent/NL7514007A/xx not_active Application Discontinuation
- 1975-12-03 FR FR7537014A patent/FR2313048A1/fr active Granted
- 1975-12-03 GB GB49614/75A patent/GB1526309A/en not_active Expired
- 1975-12-04 NZ NZ179445A patent/NZ179445A/xx unknown
- 1975-12-04 CA CA241,104A patent/CA1065326A/en not_active Expired
- 1975-12-04 ES ES443200A patent/ES443200A1/es not_active Expired
- 1975-12-04 AU AU87277/75A patent/AU504180B2/en not_active Expired
- 1975-12-04 BE BE162462A patent/BE836290A/xx unknown
- 1975-12-04 DD DD189887A patent/DD123458A5/xx unknown
- 1975-12-04 SU SU752194153A patent/SU625603A3/ru active
- 1975-12-04 IL IL48603A patent/IL48603A/xx unknown
- 1975-12-05 JP JP50144080A patent/JPS5182262A/ja active Pending
- 1975-12-05 AT AT924775A patent/AT357147B/de not_active IP Right Cessation
- 1975-12-05 ZA ZA757653A patent/ZA757653B/xx unknown
-
1976
- 1976-08-12 FR FR7624662A patent/FR2308622A1/fr not_active Withdrawn
-
1977
- 1977-02-07 SU SU772448706A patent/SU613720A3/ru active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124719A (en) * | 1974-12-06 | 1978-11-07 | Sandoz Ltd. | -4-Phenylhexahydro-4-indolinol derivatives |
| FR2365557A1 (fr) * | 1976-09-22 | 1978-04-21 | Sandoz Sa | Nouveaux perhydro-indolinols, leur preparation et leur application comme medicaments |
Also Published As
| Publication number | Publication date |
|---|---|
| AT357147B (de) | 1980-06-25 |
| NZ179445A (en) | 1978-03-06 |
| FR2313048B1 (enrdf_load_stackoverflow) | 1979-09-21 |
| DK537175A (enrdf_load_stackoverflow) | 1976-06-07 |
| AU8727775A (en) | 1977-06-09 |
| BE836290A (fr) | 1976-06-04 |
| CA1065326A (en) | 1979-10-30 |
| SU625603A3 (ru) | 1978-09-25 |
| AU504180B2 (en) | 1979-10-04 |
| SU613720A3 (ru) | 1978-06-30 |
| SE7513457L (sv) | 1976-06-08 |
| IL48603A0 (en) | 1976-02-29 |
| FR2308622A1 (fr) | 1976-11-19 |
| DK140723B (da) | 1979-11-05 |
| ES443200A1 (es) | 1978-03-01 |
| JPS5182262A (enrdf_load_stackoverflow) | 1976-07-19 |
| FI753351A7 (enrdf_load_stackoverflow) | 1976-06-07 |
| DK140723C (enrdf_load_stackoverflow) | 1980-03-31 |
| DD123458A5 (enrdf_load_stackoverflow) | 1976-12-20 |
| NL7514007A (nl) | 1976-06-09 |
| GB1526309A (en) | 1978-09-27 |
| IL48603A (en) | 1978-08-31 |
| SE408895B (sv) | 1979-07-16 |
| FR2313048A1 (fr) | 1976-12-31 |
| CH601226A5 (enrdf_load_stackoverflow) | 1978-06-30 |
| ATA924775A (de) | 1979-11-15 |
| NO754028L (enrdf_load_stackoverflow) | 1976-06-09 |
| ZA757653B (en) | 1977-07-27 |
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