CH555835A - Verfahren zur herstellung von benzodiazepinderivaten. - Google Patents
Verfahren zur herstellung von benzodiazepinderivaten.Info
- Publication number
- CH555835A CH555835A CH1566471A CH1566471A CH555835A CH 555835 A CH555835 A CH 555835A CH 1566471 A CH1566471 A CH 1566471A CH 1566471 A CH1566471 A CH 1566471A CH 555835 A CH555835 A CH 555835A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- tetrahydro
- benzodiazepin
- phenyl
- theory
- Prior art date
Links
- 230000001773 anti-convulsant effect Effects 0.000 title claims description 7
- 239000001961 anticonvulsive agent Substances 0.000 title claims description 5
- 239000000932 sedative agent Substances 0.000 title description 3
- 210000003205 muscle Anatomy 0.000 title description 2
- 229940125681 anticonvulsant agent Drugs 0.000 title 1
- 229940125723 sedative agent Drugs 0.000 title 1
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 241000699670 Mus sp. Species 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 206010010904 Convulsion Diseases 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 claims description 4
- 206010043994 Tonic convulsion Diseases 0.000 claims description 4
- 229960003965 antiepileptics Drugs 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- IUJQOUHDFKALCY-UHFFFAOYSA-N lofendazam Chemical compound C12=CC(Cl)=CC=C2NCCC(=O)N1C1=CC=CC=C1 IUJQOUHDFKALCY-UHFFFAOYSA-N 0.000 claims description 4
- 238000002844 melting Methods 0.000 claims description 4
- 230000008018 melting Effects 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- 230000002936 tranquilizing effect Effects 0.000 claims description 3
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 claims description 2
- DDBZKODCYYGHAD-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(2-hydroxyethyl)-2,3-dihydro-1,5-benzodiazepin-4-one Chemical compound ClC=1C=CC2=C(N(C(CCN2CCO)=O)C2=C(C=CC=C2)Cl)C1 DDBZKODCYYGHAD-UHFFFAOYSA-N 0.000 claims description 2
- JOKIIDQPDSUWKD-UHFFFAOYSA-N ClC=1C=CC2=C(N(C(CCN2CCCl)=O)C2=CC=CC=C2)C1 Chemical compound ClC=1C=CC2=C(N(C(CCN2CCCl)=O)C2=CC=CC=C2)C1 JOKIIDQPDSUWKD-UHFFFAOYSA-N 0.000 claims description 2
- HMHXKHWCLGAHFB-UHFFFAOYSA-N ClC=1C=CC2=C(N(C(CCN2CCO)=O)C2=CC=CC=C2)C1 Chemical compound ClC=1C=CC2=C(N(C(CCN2CCO)=O)C2=CC=CC=C2)C1 HMHXKHWCLGAHFB-UHFFFAOYSA-N 0.000 claims description 2
- LJKZJQHHHJEBKQ-UHFFFAOYSA-N ClC=1C=CC2=C(N(C(CCN2CCOC(C)=O)=O)C2=CC=CC=C2)C1 Chemical compound ClC=1C=CC2=C(N(C(CCN2CCOC(C)=O)=O)C2=CC=CC=C2)C1 LJKZJQHHHJEBKQ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 241000699673 Mesocricetus auratus Species 0.000 claims description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 230000007123 defense Effects 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000005457 ice water Substances 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 231100000518 lethal Toxicity 0.000 claims description 2
- 231100000636 lethal dose Toxicity 0.000 claims description 2
- 230000001665 lethal effect Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- 235000011152 sodium sulphate Nutrition 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims 1
- -1 succinyloxy Chemical group 0.000 abstract description 3
- 125000004423 acyloxy group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 abstract 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702052841 DE2052841A1 (de) | 1970-10-28 | 1970-10-28 | Benzodiazepinderivate |
| DE19712133065 DE2133065A1 (de) | 1971-07-02 | 1971-07-02 | Benzodiazepinderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH555835A true CH555835A (de) | 1974-11-15 |
Family
ID=25759978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1566471A CH555835A (de) | 1970-10-28 | 1971-10-27 | Verfahren zur herstellung von benzodiazepinderivaten. |
Country Status (11)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6022359U (ja) * | 1983-07-20 | 1985-02-15 | 株式会社 ほういち | ヘツド移行式印字機の印字スケ−ル |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5031158A (enrdf_load_stackoverflow) * | 1973-07-21 | 1975-03-27 |
-
1971
- 1971-10-13 AR AR23844971A patent/AR193978A1/es active
- 1971-10-13 YU YU260371A patent/YU34478B/xx unknown
- 1971-10-22 CS CS743671A patent/CS161139B2/cs unknown
- 1971-10-26 ES ES396392A patent/ES396392A1/es not_active Expired
- 1971-10-27 CA CA126275A patent/CA918661A/en not_active Expired
- 1971-10-27 JP JP8546271A patent/JPS5619347B1/ja active Pending
- 1971-10-27 AT AT928771A patent/AT313280B/de active
- 1971-10-27 SE SE1364471A patent/SE389111B/xx unknown
- 1971-10-27 NL NL7114819A patent/NL7114819A/xx not_active Application Discontinuation
- 1971-10-27 CH CH1566471A patent/CH555835A/de not_active IP Right Cessation
-
1974
- 1974-07-18 SU SU2046326A patent/SU503520A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AR193978A1 (es) | 1973-06-12 |
| SU503520A3 (ru) | 1976-02-15 |
| AT313280B (de) | 1974-02-11 |
| CS161139B2 (enrdf_load_stackoverflow) | 1975-05-04 |
| YU260371A (en) | 1979-02-28 |
| SE389111B (sv) | 1976-10-25 |
| JPS5619347B1 (enrdf_load_stackoverflow) | 1981-05-07 |
| NL7114819A (enrdf_load_stackoverflow) | 1972-05-03 |
| ES396392A1 (es) | 1974-11-01 |
| YU34478B (en) | 1979-09-10 |
| CA918661A (en) | 1973-01-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |