PL83145B1 - - Google Patents
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- Publication number
- PL83145B1 PL83145B1 PL14707071A PL14707071A PL83145B1 PL 83145 B1 PL83145 B1 PL 83145B1 PL 14707071 A PL14707071 A PL 14707071A PL 14707071 A PL14707071 A PL 14707071A PL 83145 B1 PL83145 B1 PL 83145B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- addition salts
- indole
- acid addition
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 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 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 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 description 2
- 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 2
- DJAVTUKKYQWOAP-UHFFFAOYSA-N [1-(1H-indol-4-yloxy)-4-phenyl-3-(propan-2-ylamino)butan-2-yl] 2,2-dimethylpropanoate Chemical compound C(C1=CC=CC=C1)C(C(COC1=C2C=CNC2=CC=C1)OC(C(C)(C)C)=O)NC(C)C DJAVTUKKYQWOAP-UHFFFAOYSA-N 0.000 claims 1
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003814 drug Substances 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002904 solvent 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
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005902 aminomethylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 230000003533 narcotic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940124597 therapeutic agent Drugs 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
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH437970A CH532040A (de) | 1970-03-24 | 1970-03-24 | Verfahren zur Herstellung neuer Indolderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL83145B1 true PL83145B1 (enExample) | 1975-12-31 |
Family
ID=4275012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL14707071A PL83145B1 (enExample) | 1970-03-24 | 1971-03-22 |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5442979B1 (enExample) |
| CH (1) | CH532041A (enExample) |
| ES (2) | ES389422A1 (enExample) |
| HU (1) | HU164315B (enExample) |
| IE (1) | IE35285B1 (enExample) |
| IL (1) | IL36456A (enExample) |
| PL (1) | PL83145B1 (enExample) |
| SU (1) | SU378006A3 (enExample) |
| ZA (1) | ZA711917B (enExample) |
-
1970
- 1970-03-24 CH CH1087972A patent/CH532041A/de not_active IP Right Cessation
-
1971
- 1971-03-22 PL PL14707071A patent/PL83145B1/pl unknown
- 1971-03-22 HU HUSA2180A patent/HU164315B/hu unknown
- 1971-03-22 IE IE359/71A patent/IE35285B1/xx unknown
- 1971-03-22 ES ES389422A patent/ES389422A1/es not_active Expired
- 1971-03-22 IL IL36456A patent/IL36456A/xx unknown
- 1971-03-23 JP JP1681971A patent/JPS5442979B1/ja active Pending
- 1971-03-24 ZA ZA711917A patent/ZA711917B/xx unknown
- 1971-03-24 SU SU1636301A patent/SU378006A3/ru active
-
1973
- 1973-07-16 ES ES416951A patent/ES416951A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH532041A (de) | 1972-12-31 |
| IL36456A (en) | 1974-03-14 |
| IL36456A0 (en) | 1971-05-26 |
| ZA711917B (en) | 1972-10-25 |
| HU164315B (enExample) | 1974-01-28 |
| ES389422A1 (es) | 1974-12-16 |
| ES416951A1 (es) | 1976-05-01 |
| SU378006A3 (enExample) | 1973-04-17 |
| IE35285B1 (en) | 1976-01-07 |
| JPS5442979B1 (enExample) | 1979-12-17 |
| IE35285L (en) | 1971-09-24 |
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