CH558370A - Verfahren zur herstellung von 1,3,4,5-tetrahydro-2h-1, 4-benzodiazepin-2-on-derivaten. - Google Patents
Verfahren zur herstellung von 1,3,4,5-tetrahydro-2h-1, 4-benzodiazepin-2-on-derivaten.Info
- Publication number
- CH558370A CH558370A CH1068871A CH1068871A CH558370A CH 558370 A CH558370 A CH 558370A CH 1068871 A CH1068871 A CH 1068871A CH 1068871 A CH1068871 A CH 1068871A CH 558370 A CH558370 A CH 558370A
- Authority
- CH
- Switzerland
- Prior art keywords
- general formula
- tetrahydro
- benzodiazepin
- group
- phenyl
- Prior art date
Links
- 238000006476 reductive cyclization reaction Methods 0.000 title description 3
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical class O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 title description 2
- 239000012965 benzophenone Substances 0.000 title description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 230000002829 reductive effect Effects 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 5
- 230000007935 neutral effect Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- ROXAFEIDZVHGFX-UHFFFAOYSA-N 1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Chemical class N1C(=O)CNCC2=CC=CC=C21 ROXAFEIDZVHGFX-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- HSEOUVJQONSBDC-UHFFFAOYSA-N 7-amino-5-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Chemical class C12=CC(N)=CC=C2NC(=O)CNC1C1=CC=CC=C1 HSEOUVJQONSBDC-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Chemical class 0.000 claims description 4
- 239000011707 mineral Chemical class 0.000 claims description 4
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- SREVNOABLVPRHG-UHFFFAOYSA-N 5-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Chemical class C12=CC=CC=C2NC(=O)CNC1C1=CC=CC=C1 SREVNOABLVPRHG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000002243 precursor Substances 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- -1 carbobenzoxy-amino Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- MLXBHOCKBUILHN-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1,4-benzodiazepine Chemical class C1NCCNC2=CC=CC=C21 MLXBHOCKBUILHN-UHFFFAOYSA-N 0.000 description 1
- SRJQBBLGTWTOEB-UHFFFAOYSA-N 2-(benzhydrylazaniumyl)acetate Chemical class C=1C=CC=CC=1C(NCC(=O)O)C1=CC=CC=C1 SRJQBBLGTWTOEB-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZYOLWAPZVQXTTM-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-4,5-dihydro-3h-1,4-benzodiazepin-2-one Chemical compound N1CC(=O)N(C)C2=CC=C(Cl)C=C2C1C1=CC=CC=C1 ZYOLWAPZVQXTTM-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- KORRYLOKFXJFBG-UHFFFAOYSA-N benzyl 2-amino-3-(2-benzoylanilino)-3-oxopropanoate Chemical compound C(=O)(OCC1=CC=CC=C1)C(N)C(=O)NC1=C(C(=O)C2=CC=CC=C2)C=CC=C1 KORRYLOKFXJFBG-UHFFFAOYSA-N 0.000 description 1
- KUJASAIRFDLOGZ-UHFFFAOYSA-N benzyl N-[2-(2-amino-6-benzoyl-4-nitrophenyl)-2-oxoethyl]carbamate Chemical compound C(=O)(OCC1=CC=CC=C1)NCC(=O)C1=C(C(=O)C2=CC=CC=C2)C=C(C=C1N)[N+](=O)[O-] KUJASAIRFDLOGZ-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical class C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 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
-
- 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
- C07D243/28—Preparation including building-up the benzodiazepine skeleton from compounds containing no hetero rings
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HURI000403 | 1970-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH558370A true CH558370A (de) | 1975-01-31 |
Family
ID=11000846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1068871A CH558370A (de) | 1970-07-30 | 1971-07-20 | Verfahren zur herstellung von 1,3,4,5-tetrahydro-2h-1, 4-benzodiazepin-2-on-derivaten. |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5432792B1 (cs) |
| AT (1) | AT311356B (cs) |
| CH (1) | CH558370A (cs) |
| CS (1) | CS171708B2 (cs) |
| DK (1) | DK141604B (cs) |
| ES (1) | ES393521A1 (cs) |
| NL (1) | NL7110356A (cs) |
| PL (1) | PL70872B1 (cs) |
| SE (1) | SE385888B (cs) |
| SU (1) | SU461503A3 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU187262B (en) * | 1979-08-16 | 1985-12-28 | Richter Gedeon Vegyeszet | Process for preparing new tetrahydro-1,4-benzodiazepin-2-ones |
-
1971
- 1971-07-20 CH CH1068871A patent/CH558370A/de not_active IP Right Cessation
- 1971-07-22 ES ES393521A patent/ES393521A1/es not_active Expired
- 1971-07-26 CS CS5453A patent/CS171708B2/cs unknown
- 1971-07-27 AT AT654571A patent/AT311356B/de not_active IP Right Cessation
- 1971-07-27 NL NL7110356A patent/NL7110356A/xx unknown
- 1971-07-28 SE SE7109699A patent/SE385888B/xx unknown
- 1971-07-28 PL PL1971149707A patent/PL70872B1/pl unknown
- 1971-07-29 DK DK372871AA patent/DK141604B/da unknown
- 1971-07-29 SU SU1688515A patent/SU461503A3/ru active
- 1971-07-29 JP JP5711071A patent/JPS5432792B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK141604B (da) | 1980-05-05 |
| ES393521A1 (es) | 1973-08-16 |
| NL7110356A (cs) | 1972-02-01 |
| DK141604C (cs) | 1980-10-06 |
| JPS5432792B1 (cs) | 1979-10-16 |
| PL70872B1 (cs) | 1974-04-30 |
| SE385888B (sv) | 1976-07-26 |
| AT311356B (de) | 1973-11-12 |
| SU461503A3 (ru) | 1975-02-25 |
| CS171708B2 (cs) | 1976-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |