DE2113379A1 - Verfahren zur Herstellung neuer heterocyclischer Verbindungen - Google Patents
Verfahren zur Herstellung neuer heterocyclischer VerbindungenInfo
- Publication number
- DE2113379A1 DE2113379A1 DE19712113379 DE2113379A DE2113379A1 DE 2113379 A1 DE2113379 A1 DE 2113379A1 DE 19712113379 DE19712113379 DE 19712113379 DE 2113379 A DE2113379 A DE 2113379A DE 2113379 A1 DE2113379 A1 DE 2113379A1
- Authority
- DE
- Germany
- Prior art keywords
- indole
- compounds
- pivaloyloxypropoxy
- formula
- addition salts
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 33
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
- -1 3-isopropylaminopropoxy Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- QNCHHSVBIKSEPZ-UHFFFAOYSA-N [1-(1H-indol-4-yloxy)-3-(propan-2-ylamino)propan-2-yl] 2,2-dimethylpropanoate Chemical compound C(C)(C)NCC(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O QNCHHSVBIKSEPZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- RPZJJOMRCZUFEC-UHFFFAOYSA-N 1-(tert-butylamino)-3-(1h-indol-4-yloxy)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=CC2=C1C=CN2 RPZJJOMRCZUFEC-UHFFFAOYSA-N 0.000 description 3
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- YKGJUSKLOHNPIM-UHFFFAOYSA-N 1-(1H-indol-4-yloxy)-4-phenyl-3-(propan-2-ylamino)butan-2-ol Chemical compound C(C1=CC=CC=C1)C(C(COC1=C2C=CNC2=CC=C1)O)NC(C)C YKGJUSKLOHNPIM-UHFFFAOYSA-N 0.000 description 1
- GUKLAUJRBOSKNR-UHFFFAOYSA-N 2,3-dimethyl-1h-indol-4-ol Chemical group C1=CC(O)=C2C(C)=C(C)NC2=C1 GUKLAUJRBOSKNR-UHFFFAOYSA-N 0.000 description 1
- QGWACZFSCSTOCG-UHFFFAOYSA-N 2-methyl-4-phenylmethoxy-1h-indole Chemical compound C1=CC=C2NC(C)=CC2=C1OCC1=CC=CC=C1 QGWACZFSCSTOCG-UHFFFAOYSA-N 0.000 description 1
- CTWQPSSVUYPWOM-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1CO1 CTWQPSSVUYPWOM-UHFFFAOYSA-N 0.000 description 1
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical compound OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- BYGRDLSPZRUONE-UHFFFAOYSA-N C(C(=O)O)(=O)O.C1(=CC=CC=C1)CCCNCC(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O Chemical compound C(C(=O)O)(=O)O.C1(=CC=CC=C1)CCCNCC(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O BYGRDLSPZRUONE-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- SKJFTWMIXZFOBU-BTJKTKAUSA-N OC(=O)\C=C/C(O)=O.c1cccc2[nH]ccc21 Chemical compound OC(=O)\C=C/C(O)=O.c1cccc2[nH]ccc21 SKJFTWMIXZFOBU-BTJKTKAUSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- NTIKRCIQHOXBFS-UHFFFAOYSA-N [1-(tert-butylamino)-3-(1H-indol-4-yloxy)propan-2-yl] 2,2-dimethylpropanoate Chemical compound C(C)(C)(C)NCC(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O NTIKRCIQHOXBFS-UHFFFAOYSA-N 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-M malonate(1-) Chemical compound OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- 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
-
- 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
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/12—Fertilization attaching inhibition
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH437970A CH532040A (de) | 1970-03-24 | 1970-03-24 | Verfahren zur Herstellung neuer Indolderivate |
| CH462070 | 1970-03-25 | ||
| US12310571A | 1971-03-10 | 1971-03-10 | |
| US00247083A US3829577A (en) | 1970-03-24 | 1972-04-24 | Methylenedioxy-phenoxy derivatives as agents for upsetting hormone balance in insects |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2113379A1 true DE2113379A1 (de) | 1971-10-07 |
Family
ID=27428770
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712113379 Pending DE2113379A1 (de) | 1970-03-24 | 1971-03-19 | Verfahren zur Herstellung neuer heterocyclischer Verbindungen |
| DE19712114228 Pending DE2114228A1 (de) | 1970-03-24 | 1971-03-24 | Methylendioxy-Phenylderivate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712114228 Pending DE2114228A1 (de) | 1970-03-24 | 1971-03-24 | Methylendioxy-Phenylderivate |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US3686222A (enExample) |
| AT (2) | AT323152B (enExample) |
| BE (2) | BE763354A (enExample) |
| CA (1) | CA948207A (enExample) |
| CH (2) | CH532040A (enExample) |
| DE (2) | DE2113379A1 (enExample) |
| FR (2) | FR2085733B1 (enExample) |
| GB (2) | GB1343834A (enExample) |
| NL (2) | NL7102450A (enExample) |
| OA (1) | OA03699A (enExample) |
| SE (1) | SE370073B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2635209A1 (de) * | 1975-08-15 | 1977-02-24 | Sandoz Ag | Neue 2- methylindolderivate, ihre herstellung und verwendung |
| EP0014951A3 (en) * | 1979-02-16 | 1981-02-04 | Boehringer Mannheim Gmbh | Heterocyclic oxypropanolamine derivatives, process for their preparation and medicines containing these compounds |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3946040A (en) * | 1971-03-19 | 1976-03-23 | Hoffmann-La Roche Inc. | Propynyl benzyl ethers |
| US3962282A (en) * | 1971-10-08 | 1976-06-08 | Eli Lilly And Company | Juvenile hormone mimics |
| GB1419080A (en) * | 1972-12-29 | 1975-12-24 | Cheminova As | Chemical compounds having juvenile hormone activity |
| US3933837A (en) * | 1973-07-23 | 1976-01-20 | Sterling Drug Inc. | 3,4-Methylenedioxyphenoxy-alkyl diketones and keto-esters |
| US4246284A (en) * | 1973-07-23 | 1981-01-20 | Sterling Drug Inc. | Aminosulfonyl-substituted aryloxyalkyl diketones |
| US4182761A (en) * | 1973-07-23 | 1980-01-08 | Sterling Drug Inc. | Acyloxy-substituted aryloxyalkyl diketones |
| US4171376A (en) * | 1973-07-23 | 1979-10-16 | Sterling Drug Inc. | Aryloxyalkyl keto-esters |
| US4002615A (en) * | 1974-03-13 | 1977-01-11 | A/S Cheminova | Terpenoid compounds of substituted hydroxyalkyl-pyridines having juvenile hormone activity |
| ZA752736B (en) * | 1974-06-17 | 1976-04-28 | Hoffmann La Roche | Phenyl derivatives |
| US3968234A (en) * | 1975-03-05 | 1976-07-06 | The United States Of America As Represented By The Secretary Of Agriculture | Cinnamyl-sesamol derivatives as insect chemosterilants |
| US4206197A (en) * | 1975-11-26 | 1980-06-03 | The United States Of America As Represented By The Secretary Of The Navy | Chemical encapsulation and distribution |
| EP0002792A1 (en) * | 1978-01-03 | 1979-07-11 | Sandoz Ag | 3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them |
| US4788054A (en) * | 1986-07-11 | 1988-11-29 | Stepan Company | N-phenylphthalisomides as ultraviolet radiation absorbers |
| JP4456334B2 (ja) * | 2003-02-14 | 2010-04-28 | 高砂香料工業株式会社 | メラニン生成抑制剤及びそれを含有する皮膚外用剤 |
-
1970
- 1970-03-24 CH CH437970A patent/CH532040A/de not_active IP Right Cessation
- 1970-03-25 CH CH462070A patent/CH542580A/de not_active IP Right Cessation
-
1971
- 1971-02-24 BE BE763354A patent/BE763354A/xx unknown
- 1971-02-24 NL NL7102450A patent/NL7102450A/xx unknown
- 1971-03-10 US US123105A patent/US3686222A/en not_active Expired - Lifetime
- 1971-03-19 DE DE19712113379 patent/DE2113379A1/de active Pending
- 1971-03-22 BE BE764660A patent/BE764660A/xx unknown
- 1971-03-22 CA CA108,321A patent/CA948207A/en not_active Expired
- 1971-03-22 FR FR7109963A patent/FR2085733B1/fr not_active Expired
- 1971-03-23 SE SE03739/71A patent/SE370073B/xx unknown
- 1971-03-23 AT AT959772A patent/AT323152B/de not_active IP Right Cessation
- 1971-03-23 FR FR7110148A patent/FR2093422A5/fr not_active Expired
- 1971-03-23 AT AT249571A patent/AT317885B/de not_active IP Right Cessation
- 1971-03-23 NL NL7103858A patent/NL7103858A/xx not_active Application Discontinuation
- 1971-03-23 OA OA54210A patent/OA03699A/xx unknown
- 1971-03-24 DE DE19712114228 patent/DE2114228A1/de active Pending
- 1971-04-19 GB GB2480871*A patent/GB1343834A/en not_active Expired
- 1971-04-19 GB GB25243/71A patent/GB1293312A/en not_active Expired
-
1972
- 1972-04-24 US US00247083A patent/US3829577A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2635209A1 (de) * | 1975-08-15 | 1977-02-24 | Sandoz Ag | Neue 2- methylindolderivate, ihre herstellung und verwendung |
| EP0014951A3 (en) * | 1979-02-16 | 1981-02-04 | Boehringer Mannheim Gmbh | Heterocyclic oxypropanolamine derivatives, process for their preparation and medicines containing these compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| OA03699A (fr) | 1971-12-24 |
| BE764660A (fr) | 1971-09-22 |
| US3686222A (en) | 1972-08-22 |
| CH542580A (de) | 1973-11-30 |
| CH532040A (de) | 1972-12-31 |
| NL7102450A (enExample) | 1971-09-28 |
| AT323152B (de) | 1975-06-25 |
| FR2093422A5 (enExample) | 1972-01-28 |
| FR2085733B1 (enExample) | 1974-05-24 |
| GB1343834A (en) | 1974-01-16 |
| US3829577A (en) | 1974-08-13 |
| GB1293312A (en) | 1972-10-18 |
| AT317885B (de) | 1974-09-25 |
| BE763354A (fr) | 1971-08-24 |
| FR2085733A1 (enExample) | 1971-12-31 |
| NL7103858A (enExample) | 1971-09-28 |
| DE2114228A1 (de) | 1971-10-14 |
| CA948207A (en) | 1974-05-28 |
| SE370073B (enExample) | 1974-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2113379A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Verbindungen | |
| DE2113733A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Verbindungen | |
| DE2230426A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| DE1815802A1 (de) | Verfahren zur Herstellung von substituierten Phenylessigsaeuren | |
| DE2035419A1 (de) | Neue Arzneimittel mit antineoplasüscher Wirksamkeit | |
| DE2331721A1 (de) | Verfahren zur herstellung neuer heterocyclischer verbindungen | |
| DE2148552A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Verbindungen | |
| DE1470382C (de) | 7 Methyl 3 (2 aminobutyl)indole und deren Saureadditionssalze mit pharmakolo gisch vertraglichen Sauren und Verfahren zu ihrer Herstellung | |
| DE2037319C3 (de) | Amindenvate des 1,4 Athano 1,2,3, 4 tetrahydro 5 naphtols und deren Salze, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate | |
| DE1470275C (de) | Oxazohdon (2)-denvate und Ver fahren zu ihrer Herstellung | |
| DE2148553A1 (de) | Verfahren zur Herstellung neuer heterocyclischer Verbindungen | |
| CH511840A (de) | Verfahren zur Herstellung von neuen Indolderivaten | |
| AT221515B (de) | Verfahren zur Herstellung neuer 4-Oxo-1,2,3,4-tetrahydronaphthalin-carbonsäureamide | |
| DE2200204A1 (de) | Verfahren zur Herstellung neuer heterozyklischer Verbindungen | |
| AT276383B (de) | Verfahren zur Herstellung von neuen Phenylisoindolderivaten und deren Salzen | |
| AT219037B (de) | Verfahren zur Herstellung neuer, basischer Indol-Derivate | |
| CH535764A (de) | Verfahren zur Herstellung neuer Indolderivate | |
| DE913288C (de) | Verfahren zur Herstellung von Benz-(cd)-indolin und Derivaten desselben | |
| CH565740A5 (en) | 4-(3-Amino-2-acyloxy-propoxy)-9-fluorenones - with circulatory and anti-arrhythmic activity | |
| DE1668964A1 (de) | Neue Trimethylhydrochinonderivate und Verfahren zur Herstellung derselben | |
| DE2206961A1 (de) | Verfahren zur Herstellung neuer Phenyläthylamin-Derivate | |
| DE2264903A1 (de) | Piperidinderivate | |
| CH535763A (de) | Verfahren zur Herstellung neuer Indolderivate | |
| DE2810869A1 (de) | 3-amino-2-hydroxypropoxy-derivate, ihre herstellung und verwendung | |
| DE2224792A1 (de) | Verfahren zur Herstellung neuer tricyclischer Verbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHJ | Non-payment of the annual fee |