DE2311714A1 - Neue 1,4-benzodiazepine - Google Patents
Neue 1,4-benzodiazepineInfo
- Publication number
- DE2311714A1 DE2311714A1 DE2311714A DE2311714A DE2311714A1 DE 2311714 A1 DE2311714 A1 DE 2311714A1 DE 2311714 A DE2311714 A DE 2311714A DE 2311714 A DE2311714 A DE 2311714A DE 2311714 A1 DE2311714 A1 DE 2311714A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- chloro
- dihydro
- benzodiazepin
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 29
- 150000001875 compounds Chemical group 0.000 claims description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 12
- 239000012279 sodium borohydride Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- -1 Acetoxymethyl Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229940049706 benzodiazepine Drugs 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
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- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 241000251730 Chondrichthyes Species 0.000 claims 1
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- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
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- 238000005658 halogenation reaction Methods 0.000 claims 1
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- 238000002844 melting Methods 0.000 description 23
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- 238000004519 manufacturing process Methods 0.000 description 7
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
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- 239000008120 corn starch Substances 0.000 description 5
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- 238000000354 decomposition reaction Methods 0.000 description 5
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- 159000000000 sodium salts Chemical class 0.000 description 4
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- ZXULLMNFMIZZCF-UHFFFAOYSA-N 3-methyl-1,4-benzodiazepin-2-one Chemical compound O=C1C(C)=NC=C2C=CC=CC2=N1 ZXULLMNFMIZZCF-UHFFFAOYSA-N 0.000 description 3
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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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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)
Priority Applications (15)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2311714A DE2311714A1 (de) | 1973-03-09 | 1973-03-09 | Neue 1,4-benzodiazepine |
NL7401546A NL7401546A (fr) | 1973-03-09 | 1974-02-05 | |
AT112574A AT347860B (de) | 1973-03-09 | 1974-02-13 | Verfahren und vorrichtung zur herstellung von mit oeffnungsfaeden versehenen eindosenbehaeltern, gefertigt aus flexiblen folienhaelften |
ES423226A ES423226A1 (es) | 1973-03-09 | 1974-02-14 | Procedimiento para la preparacion de nuevas 1,4-benzodiaze-pinas. |
RO7400077932A RO63578A (fr) | 1973-03-09 | 1974-03-06 | Procede pour la preparation des derives du 1,4-benzodia zepines |
IL44366A IL44366A0 (en) | 1973-03-09 | 1974-03-07 | New 1,4-benzodiazepines,their preparation and pharmaceutical compositions containing them |
DD177031A DD112264A5 (fr) | 1973-03-09 | 1974-03-07 | |
AU66416/74A AU6641674A (en) | 1973-03-09 | 1974-03-07 | Benzodiazepines |
JP49026747A JPS49125383A (fr) | 1973-03-09 | 1974-03-07 | |
HUTO955A HU166787B (fr) | 1973-03-09 | 1974-03-07 | |
BE141829A BE812087A (fr) | 1973-03-09 | 1974-03-08 | Nouvelles 1 |
FR7407993A FR2220269A1 (en) | 1973-03-09 | 1974-03-08 | 3-Hydroxymethyl 5-phenyl 1,4-benzodiazepin-2-ones - with CNS depressant activity, e.g. sedative props. |
SE7403160A SE7403160L (fr) | 1973-03-09 | 1974-03-08 | |
ES426948A ES426948A1 (es) | 1973-03-09 | 1974-06-04 | Procedimiento para la preparacion de nuevas 1,4-benzodiaze-pinas. |
ES426949A ES426949A1 (es) | 1973-03-09 | 1974-06-04 | Procedimiento para la preparacion de nuevas 1,4-benzodia- zepinas. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2311714A DE2311714A1 (de) | 1973-03-09 | 1973-03-09 | Neue 1,4-benzodiazepine |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2311714A1 true DE2311714A1 (de) | 1974-09-19 |
Family
ID=5874264
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2311714A Pending DE2311714A1 (de) | 1973-03-09 | 1973-03-09 | Neue 1,4-benzodiazepine |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS49125383A (fr) |
AT (1) | AT347860B (fr) |
AU (1) | AU6641674A (fr) |
BE (1) | BE812087A (fr) |
DD (1) | DD112264A5 (fr) |
DE (1) | DE2311714A1 (fr) |
ES (3) | ES423226A1 (fr) |
FR (1) | FR2220269A1 (fr) |
HU (1) | HU166787B (fr) |
IL (1) | IL44366A0 (fr) |
NL (1) | NL7401546A (fr) |
RO (1) | RO63578A (fr) |
SE (1) | SE7403160L (fr) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1332410C (fr) * | 1984-06-26 | 1994-10-11 | Roger M. Freidinger | Analogues de benzodiazepines |
US4820834A (en) * | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
-
1973
- 1973-03-09 DE DE2311714A patent/DE2311714A1/de active Pending
-
1974
- 1974-02-05 NL NL7401546A patent/NL7401546A/xx unknown
- 1974-02-13 AT AT112574A patent/AT347860B/de not_active IP Right Cessation
- 1974-02-14 ES ES423226A patent/ES423226A1/es not_active Expired
- 1974-03-06 RO RO7400077932A patent/RO63578A/fr unknown
- 1974-03-07 DD DD177031A patent/DD112264A5/xx unknown
- 1974-03-07 IL IL44366A patent/IL44366A0/xx unknown
- 1974-03-07 JP JP49026747A patent/JPS49125383A/ja active Pending
- 1974-03-07 AU AU66416/74A patent/AU6641674A/en not_active Expired
- 1974-03-07 HU HUTO955A patent/HU166787B/hu unknown
- 1974-03-08 SE SE7403160A patent/SE7403160L/xx not_active Application Discontinuation
- 1974-03-08 BE BE141829A patent/BE812087A/fr unknown
- 1974-03-08 FR FR7407993A patent/FR2220269A1/fr not_active Withdrawn
- 1974-06-04 ES ES426949A patent/ES426949A1/es not_active Expired
- 1974-06-04 ES ES426948A patent/ES426948A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AU6641674A (en) | 1975-09-11 |
HU166787B (fr) | 1975-05-28 |
JPS49125383A (fr) | 1974-11-30 |
AT347860B (de) | 1979-01-25 |
RO63578A (fr) | 1978-08-15 |
ES426948A1 (es) | 1976-07-16 |
ATA112574A (de) | 1978-05-15 |
ES423226A1 (es) | 1976-05-01 |
SE7403160L (fr) | 1974-09-10 |
ES426949A1 (es) | 1976-07-16 |
NL7401546A (fr) | 1974-09-11 |
DD112264A5 (fr) | 1975-04-05 |
IL44366A0 (en) | 1974-06-30 |
FR2220269A1 (en) | 1974-10-04 |
BE812087A (fr) | 1974-09-09 |
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