SU585814A3 - Способ получени производных бензодиазепина - Google Patents
Способ получени производных бензодиазепинаInfo
- Publication number
- SU585814A3 SU585814A3 SU711692354A SU1692354A SU585814A3 SU 585814 A3 SU585814 A3 SU 585814A3 SU 711692354 A SU711692354 A SU 711692354A SU 1692354 A SU1692354 A SU 1692354A SU 585814 A3 SU585814 A3 SU 585814A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formula
- group
- alkali metal
- mixture
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- -1 trifluoromethyl- Chemical group 0.000 claims 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- 229910052783 alkali metal Inorganic materials 0.000 claims 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000001340 alkali metals Chemical class 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- 238000010521 absorption reaction Methods 0.000 claims 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052751 metal Inorganic materials 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 239000012047 saturated solution Substances 0.000 claims 2
- 239000000741 silica gel Substances 0.000 claims 2
- 229910002027 silica gel Inorganic materials 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims 2
- 239000012312 sodium hydride Substances 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 claims 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000002026 chloroform extract Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229940113088 dimethylacetamide Drugs 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000284 extract Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000002480 mineral oil Substances 0.000 claims 1
- 235000010446 mineral oil Nutrition 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000000725 suspension Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45074410A JPS4835273B1 (https=) | 1970-08-24 | 1970-08-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU585814A3 true SU585814A3 (ru) | 1977-12-25 |
Family
ID=13546376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU711692354A SU585814A3 (ru) | 1970-08-24 | 1971-08-22 | Способ получени производных бензодиазепина |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3752806A (https=) |
| JP (1) | JPS4835273B1 (https=) |
| AT (1) | AT311359B (https=) |
| BE (1) | BE771644A (https=) |
| CA (1) | CA1005442A (https=) |
| CH (1) | CH562241A5 (https=) |
| CS (1) | CS174163B2 (https=) |
| DK (1) | DK129456B (https=) |
| ES (1) | ES394452A1 (https=) |
| FI (1) | FI51483C (https=) |
| FR (1) | FR2103463B1 (https=) |
| GB (1) | GB1307475A (https=) |
| HU (1) | HU163047B (https=) |
| IL (1) | IL37548A (https=) |
| NL (1) | NL7111574A (https=) |
| NO (1) | NO132235C (https=) |
| PL (1) | PL81799B1 (https=) |
| SE (1) | SE386170B (https=) |
| SU (1) | SU585814A3 (https=) |
| ZA (1) | ZA715600B (https=) |
-
1970
- 1970-08-24 JP JP45074410A patent/JPS4835273B1/ja active Pending
-
1971
- 1971-08-16 FR FR7129852A patent/FR2103463B1/fr not_active Expired
- 1971-08-16 US US00172298A patent/US3752806A/en not_active Expired - Lifetime
- 1971-08-17 CA CA120,750A patent/CA1005442A/en not_active Expired
- 1971-08-18 GB GB3879671A patent/GB1307475A/en not_active Expired
- 1971-08-18 HU HUSU664A patent/HU163047B/hu unknown
- 1971-08-19 NO NO3092/71A patent/NO132235C/no unknown
- 1971-08-19 CH CH1218271A patent/CH562241A5/xx not_active IP Right Cessation
- 1971-08-20 ZA ZA715600A patent/ZA715600B/xx unknown
- 1971-08-20 AT AT730471A patent/AT311359B/de not_active IP Right Cessation
- 1971-08-20 FI FI712328A patent/FI51483C/fi active
- 1971-08-22 SU SU711692354A patent/SU585814A3/ru active
- 1971-08-22 IL IL37548A patent/IL37548A/en unknown
- 1971-08-23 DK DK412871AA patent/DK129456B/da unknown
- 1971-08-23 NL NL7111574A patent/NL7111574A/xx not_active Application Discontinuation
- 1971-08-23 BE BE771644A patent/BE771644A/xx unknown
- 1971-08-23 CS CS6029A patent/CS174163B2/cs unknown
- 1971-08-23 PL PL1971150145A patent/PL81799B1/pl unknown
- 1971-08-23 SE SE7110688A patent/SE386170B/xx unknown
- 1971-08-23 ES ES394452A patent/ES394452A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI51483B (https=) | 1976-09-30 |
| DK129456C (https=) | 1975-03-03 |
| ES394452A1 (es) | 1974-03-01 |
| FR2103463A1 (https=) | 1972-04-14 |
| US3752806A (en) | 1973-08-14 |
| FR2103463B1 (https=) | 1975-04-18 |
| AT311359B (de) | 1973-11-12 |
| DK129456B (da) | 1974-10-14 |
| JPS4835273B1 (https=) | 1973-10-26 |
| ZA715600B (en) | 1972-05-31 |
| NL7111574A (https=) | 1972-02-28 |
| IL37548A (en) | 1974-10-22 |
| GB1307475A (en) | 1973-02-21 |
| CA1005442A (en) | 1977-02-15 |
| IL37548A0 (en) | 1971-11-29 |
| DE2141443B2 (de) | 1977-01-13 |
| BE771644A (fr) | 1971-12-31 |
| NO132235B (https=) | 1975-06-30 |
| CH562241A5 (https=) | 1975-05-30 |
| DE2141443A1 (de) | 1972-03-02 |
| SE386170B (sv) | 1976-08-02 |
| PL81799B1 (https=) | 1975-08-30 |
| NO132235C (https=) | 1975-10-08 |
| CS174163B2 (https=) | 1977-03-31 |
| FI51483C (fi) | 1977-01-10 |
| HU163047B (https=) | 1973-05-28 |
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