NO754028L - - Google Patents
Info
- Publication number
- NO754028L NO754028L NO754028A NO754028A NO754028L NO 754028 L NO754028 L NO 754028L NO 754028 A NO754028 A NO 754028A NO 754028 A NO754028 A NO 754028A NO 754028 L NO754028 L NO 754028L
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- group
- alkyl
- formula
- 7ars
- Prior art date
Links
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- -1 tyr hydrogen Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- 150000001721 carbon Chemical group 0.000 claims 2
- 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 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 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 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 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
- 238000010992 reflux Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- 239000002585 base Substances 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
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052987 metal hydride Inorganic materials 0.000 description 3
- 150000004681 metal hydrides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 238000005932 reductive alkylation reaction 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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 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
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-M malonate(1-) Chemical compound OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000007017 scission Effects 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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- 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
- 208000020401 Depressive disease Diseases 0.000 description 1
- 238000003747 Grignard reaction Methods 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
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-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
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 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
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 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
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 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 1
- 150000002894 organic compounds Chemical class 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000033764 rhythmic process 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
- 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
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 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 (es) | 1974-12-06 | 1974-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO754028L true NO754028L (es) | 1976-06-09 |
Family
ID=4415551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO754028A NO754028L (es) | 1974-12-06 | 1975-11-28 |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5182262A (es) |
| AT (1) | AT357147B (es) |
| AU (1) | AU504180B2 (es) |
| BE (1) | BE836290A (es) |
| CA (1) | CA1065326A (es) |
| CH (1) | CH601226A5 (es) |
| DD (1) | DD123458A5 (es) |
| DE (1) | DE2552563A1 (es) |
| DK (1) | DK140723B (es) |
| ES (1) | ES443200A1 (es) |
| FI (1) | FI753351A (es) |
| FR (2) | FR2313048A1 (es) |
| GB (1) | GB1526309A (es) |
| IL (1) | IL48603A (es) |
| NL (1) | NL7514007A (es) |
| NO (1) | NO754028L (es) |
| NZ (1) | NZ179445A (es) |
| SE (1) | SE408895B (es) |
| SU (2) | SU625603A3 (es) |
| ZA (1) | ZA757653B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4124719A (en) * | 1974-12-06 | 1978-11-07 | Sandoz Ltd. | -4-Phenylhexahydro-4-indolinol derivatives |
| DE2741009A1 (de) | 1976-09-22 | 1978-03-23 | Sandoz Ag | 4-styryl-4-indolinol-derivate, ihre verwendung und herstellung |
-
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/FI753351A/fi not_active Application Discontinuation
- 1975-11-28 SE SE7513457A patent/SE408895B/xx unknown
- 1975-11-28 NO NO754028A patent/NO754028L/no unknown
- 1975-12-02 NL NL7514007A patent/NL7514007A/xx not_active Application Discontinuation
- 1975-12-03 GB GB49614/75A patent/GB1526309A/en not_active Expired
- 1975-12-03 FR FR7537014A patent/FR2313048A1/fr active Granted
- 1975-12-04 CA CA241,104A patent/CA1065326A/en not_active Expired
- 1975-12-04 IL IL48603A patent/IL48603A/xx unknown
- 1975-12-04 SU SU752194153A patent/SU625603A3/ru active
- 1975-12-04 ES ES443200A patent/ES443200A1/es not_active Expired
- 1975-12-04 NZ NZ179445A patent/NZ179445A/xx unknown
- 1975-12-04 BE BE162462A patent/BE836290A/xx unknown
- 1975-12-04 DD DD189887A patent/DD123458A5/xx unknown
- 1975-12-04 AU AU87277/75A patent/AU504180B2/en not_active Expired
- 1975-12-05 ZA ZA757653A patent/ZA757653B/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
-
1976
- 1976-08-12 FR FR7624662A patent/FR2308622A1/fr not_active Withdrawn
-
1977
- 1977-02-07 SU SU772448706A patent/SU613720A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| NZ179445A (en) | 1978-03-06 |
| CH601226A5 (es) | 1978-06-30 |
| FR2313048B1 (es) | 1979-09-21 |
| DK140723C (es) | 1980-03-31 |
| SU625603A3 (ru) | 1978-09-25 |
| DK140723B (da) | 1979-11-05 |
| FI753351A (es) | 1976-06-07 |
| CA1065326A (en) | 1979-10-30 |
| SU613720A3 (ru) | 1978-06-30 |
| AU8727775A (en) | 1977-06-09 |
| ATA924775A (de) | 1979-11-15 |
| AT357147B (de) | 1980-06-25 |
| FR2313048A1 (fr) | 1976-12-31 |
| SE7513457L (sv) | 1976-06-08 |
| JPS5182262A (es) | 1976-07-19 |
| SE408895B (sv) | 1979-07-16 |
| IL48603A0 (en) | 1976-02-29 |
| DE2552563A1 (de) | 1976-06-10 |
| DD123458A5 (es) | 1976-12-20 |
| NL7514007A (nl) | 1976-06-09 |
| ES443200A1 (es) | 1978-03-01 |
| GB1526309A (en) | 1978-09-27 |
| DK537175A (es) | 1976-06-07 |
| AU504180B2 (en) | 1979-10-04 |
| FR2308622A1 (fr) | 1976-11-19 |
| IL48603A (en) | 1978-08-31 |
| BE836290A (fr) | 1976-06-04 |
| ZA757653B (en) | 1977-07-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Louis et al. | Asymmetric nitrone-vinyl sulfoxide cycloadditions | |
| DE2817593A1 (de) | Mercaptoalkylsulfonylprolin-derivate und verwandte verbindungen | |
| US4361562A (en) | 3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them | |
| EP1421062A1 (en) | Novel cyclohexyl sulphones | |
| WO1995030675A1 (en) | Biphenylcarboxamides useful as 5-ht1d antagonists | |
| Bowman et al. | Ring expansion of benzocyclic ketones via transient alkoxyl radicals: The side chain incorporation approach | |
| WO1998031677A1 (fr) | Nouvelles amines aromatiques derivees d'amines cycliques utiles comme medicaments | |
| CS205087B2 (en) | Method of producing hydroxy-and oxoderivatives of aryloxy-and arylthio-perhydro-aza heterocycles | |
| CA2213815C (en) | Pyrrolidinyl hydroxamic acid compounds and their production process | |
| NO754028L (es) | ||
| CA1039731A (en) | Process for preparing new 2-methoxy-benzamide derivatives | |
| DE2230426A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| FR2662442A1 (fr) | Trifluoromethylphenyltetrahydropyridines n-substituees procede pour leur preparation, intermediaires du procede et compositions pharmaceutiques les contenant. | |
| NL7809120A (nl) | Werkwijze voor de bereiding van proline-derivaten. | |
| IE913964A1 (en) | New imidazole compounds, process for the preparation thereof, and pharmaceutical compositions containing them | |
| US4307110A (en) | Mercaptoacyl derivatives of 3-substituted proline derivatives | |
| US3539579A (en) | 1 - (3 - cyano - 3,3 - diphenyl - propyl) - 4- phenyl - piperidine - 4 - carboxylic acid esters | |
| Axelsson et al. | The nucleophilic ring‐opening of N‐benzylquinuclidinium bromide | |
| US2551152A (en) | 4-aryl-piperidyl-(4)-ketones | |
| Johnson et al. | 2-(3-Aryl-5-pyrazolyl) benzoic acid chemistry | |
| IE50816B1 (en) | Novel indane derivatives,process for their preparation,their use as pharmaceuticals and pharmaceutical compositions containing said derivatives | |
| DK150541B (da) | Analogifremgangsmaade til fremstilling af 1-(3-bromisoxazol-5-yl)-2-tert.-butyl-aminoethanol eller farmaceutisk acceptable syreadditionssalte heraf | |
| IE45436B1 (en) | 12-azaprostanoic acid derivatives | |
| US4124719A (en) | -4-Phenylhexahydro-4-indolinol derivatives | |
| GB1575852A (en) | Hexahydro-4-indolinol derivatives |