SU527135A3 - Способ получени производных индола или их солей - Google Patents
Способ получени производных индола или их солейInfo
- Publication number
- SU527135A3 SU527135A3 SU1843832A SU1843832A SU527135A3 SU 527135 A3 SU527135 A3 SU 527135A3 SU 1843832 A SU1843832 A SU 1843832A SU 1843832 A SU1843832 A SU 1843832A SU 527135 A3 SU527135 A3 SU 527135A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- hydrochloride
- acetic acid
- chloroquinazolin
- acid
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 10
- 238000000034 method Methods 0.000 title description 5
- 150000002475 indoles Chemical class 0.000 title description 2
- 239000000203 mixture Substances 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- -1 (2,6-dichloropyrimidin-4-yl) -2-methylindole-3-acetic acid Chemical compound 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000010992 reflux Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229940040102 levulinic acid Drugs 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LGLDKACKTJEXAG-UHFFFAOYSA-N 2-[1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound ClC1=CC=C2C(N3C4=CC=C(C=C4C(CC(O)=O)=C3C)OC)=NC=NC2=C1 LGLDKACKTJEXAG-UHFFFAOYSA-N 0.000 description 2
- FDPHWQSGEWRZOL-UHFFFAOYSA-N 4,7-dichloroquinazoline Chemical compound ClC1=NC=NC2=CC(Cl)=CC=C21 FDPHWQSGEWRZOL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 229910000503 Na-aluminosilicate Inorganic materials 0.000 description 2
- ZVDDJPSHRNMSKV-UHFFFAOYSA-N acetaldehyde;hydrochloride Chemical compound Cl.CC=O ZVDDJPSHRNMSKV-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000429 sodium aluminium silicate Substances 0.000 description 2
- 235000012217 sodium aluminium silicate Nutrition 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
- 239000011780 sodium chloride Substances 0.000 description 2
- UBVFWLHAMDUGCM-UHFFFAOYSA-N 2-(1h-indol-3-yl)-2-methylbutanoic acid Chemical compound C1=CC=C2C(C(C)(C(O)=O)CC)=CNC2=C1 UBVFWLHAMDUGCM-UHFFFAOYSA-N 0.000 description 1
- HOBMYIAZZQYRPU-UHFFFAOYSA-N 2-[1-(2,6-dimethoxypyrimidin-4-yl)-2,5-dimethylindol-3-yl]acetic acid Chemical compound COC1=NC(OC)=CC(N2C3=CC=C(C)C=C3C(CC(O)=O)=C2C)=N1 HOBMYIAZZQYRPU-UHFFFAOYSA-N 0.000 description 1
- JUBXUCPLAXHEKJ-UHFFFAOYSA-N 2-[1-(2-amino-6-methylpyrimidin-4-yl)-2-methylindol-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CC=C2N1C1=CC(C)=NC(N)=N1 JUBXUCPLAXHEKJ-UHFFFAOYSA-N 0.000 description 1
- UYPXJZIRFRPDMO-UHFFFAOYSA-N 2-[1-(7-bromoquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound BrC1=CC=C2C(N3C4=CC=C(C=C4C(CC(O)=O)=C3C)OC)=NC=NC2=C1 UYPXJZIRFRPDMO-UHFFFAOYSA-N 0.000 description 1
- KWOZWIAPRITLSW-UHFFFAOYSA-N 2-[1-(7-chlorocinnolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound ClC1=CC=C2C(N3C4=CC=C(C=C4C(CC(O)=O)=C3C)OC)=CN=NC2=C1 KWOZWIAPRITLSW-UHFFFAOYSA-N 0.000 description 1
- ZDUKAIQCTXBWHR-UHFFFAOYSA-N 2-[1-(7-chloroquinazolin-4-yl)-2,5-dimethylindol-3-yl]acetic acid Chemical compound ClC1=CC=C2C(N3C4=CC=C(C)C=C4C(CC(O)=O)=C3C)=NC=NC2=C1 ZDUKAIQCTXBWHR-UHFFFAOYSA-N 0.000 description 1
- POSALHQVEGDCEE-UHFFFAOYSA-N 2-[1-(7-chloroquinazolin-4-yl)-5-fluoro-2-methylindol-3-yl]acetic acid Chemical compound ClC1=CC=C2C(N3C4=CC=C(F)C=C4C(CC(O)=O)=C3C)=NC=NC2=C1 POSALHQVEGDCEE-UHFFFAOYSA-N 0.000 description 1
- SZUKHHUIJLVIEG-UHFFFAOYSA-N 2-[1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]ethanol Chemical compound ClC1=CC=C2C(N3C4=CC=C(C=C4C(CCO)=C3C)OC)=NC=NC2=C1 SZUKHHUIJLVIEG-UHFFFAOYSA-N 0.000 description 1
- VJXYIASUBZUHMU-UHFFFAOYSA-N 2-[1-(7-chloroquinolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound ClC1=CC=C2C(N3C4=CC=C(C=C4C(CC(O)=O)=C3C)OC)=CC=NC2=C1 VJXYIASUBZUHMU-UHFFFAOYSA-N 0.000 description 1
- MGUVHKVIZNRKDV-UHFFFAOYSA-N 2-[1-(7-fluoroquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound FC1=CC=C2C(N3C4=CC=C(C=C4C(CC(O)=O)=C3C)OC)=NC=NC2=C1 MGUVHKVIZNRKDV-UHFFFAOYSA-N 0.000 description 1
- RRYYRZJNFZGTGZ-UHFFFAOYSA-N 2-[5-methoxy-2-methyl-1-(2-methylquinazolin-4-yl)indol-3-yl]acetic acid Chemical compound C1=CC=C2C(N3C4=CC=C(C=C4C(CC(O)=O)=C3C)OC)=NC(C)=NC2=C1 RRYYRZJNFZGTGZ-UHFFFAOYSA-N 0.000 description 1
- NPTGVVKPLWFPPX-UHFFFAOYSA-N 2-amino-4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC(N)=N1 NPTGVVKPLWFPPX-UHFFFAOYSA-N 0.000 description 1
- UZTJTTKEYGHTNM-UHFFFAOYSA-N 2-methyl-4-oxopentanoic acid Chemical compound OC(=O)C(C)CC(C)=O UZTJTTKEYGHTNM-UHFFFAOYSA-N 0.000 description 1
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- TXWGINUZLBAKDF-UHFFFAOYSA-N N-Deschlorobenzoyl indomethacin Chemical compound COC1=CC=C2NC(C)=C(CC(O)=O)C2=C1 TXWGINUZLBAKDF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- OXCKDZVJHZSKOE-UHFFFAOYSA-N [1-(7-chloroquinazolin-4-yl)-4-methoxycyclohexa-2,4-dien-1-yl]hydrazine Chemical compound C1=CC(OC)=CCC1(NN)C1=NC=NC2=CC(Cl)=CC=C12 OXCKDZVJHZSKOE-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- NIUCWLBRRWENPN-UHFFFAOYSA-N methyl 2-[1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OC)=C(C)N1C1=NC=NC2=CC(Cl)=CC=C12 NIUCWLBRRWENPN-UHFFFAOYSA-N 0.000 description 1
- WCKGKJATLHBHCC-UHFFFAOYSA-N methyl 2-[1-(7-chloroquinolin-4-yl)-5-methoxy-2-methylindol-3-yl]acetate Chemical compound C12=CC=C(OC)C=C2C(CC(=O)OC)=C(C)N1C1=CC=NC2=CC(Cl)=CC=C12 WCKGKJATLHBHCC-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HPOKESDSMZRZLC-UHFFFAOYSA-N propan-2-one;hydrochloride Chemical compound Cl.CC(C)=O HPOKESDSMZRZLC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 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 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1811672A GB1356834A (en) | 1971-11-03 | 1971-11-03 | Indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU527135A3 true SU527135A3 (ru) | 1976-08-30 |
Family
ID=10458604
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1843832A SU527135A3 (ru) | 1971-11-03 | 1972-10-20 | Способ получени производных индола или их солей |
| SU7402043161A SU577980A3 (ru) | 1971-11-03 | 1974-07-11 | Способ получени производных индола или их солей |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7402043161A SU577980A3 (ru) | 1971-11-03 | 1974-07-11 | Способ получени производных индола или их солей |
Country Status (6)
| Country | Link |
|---|---|
| AT (2) | AT320633B (enExample) |
| AU (1) | AU464145B2 (enExample) |
| CS (1) | CS178120B2 (enExample) |
| PH (1) | PH10303A (enExample) |
| SU (2) | SU527135A3 (enExample) |
| ZA (1) | ZA727007B (enExample) |
-
1972
- 1972-10-02 ZA ZA727007A patent/ZA727007B/xx unknown
- 1972-10-04 AU AU47381/72A patent/AU464145B2/en not_active Expired
- 1972-10-20 SU SU1843832A patent/SU527135A3/ru active
- 1972-10-23 PH PH14034A patent/PH10303A/en unknown
- 1972-11-03 CS CS743772A patent/CS178120B2/cs unknown
- 1972-11-03 AT AT934272A patent/AT320633B/de not_active IP Right Cessation
- 1972-11-03 AT AT100274A patent/AT328432B/de not_active IP Right Cessation
-
1974
- 1974-07-11 SU SU7402043161A patent/SU577980A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AU4738172A (en) | 1974-04-11 |
| CS178120B2 (enExample) | 1977-08-31 |
| AU464145B2 (en) | 1975-08-14 |
| ATA100274A (de) | 1975-06-15 |
| AT320633B (de) | 1975-02-25 |
| SU577980A3 (ru) | 1977-10-25 |
| ZA727007B (en) | 1973-06-27 |
| PH10303A (en) | 1976-11-10 |
| AT328432B (de) | 1976-03-25 |
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