GB1476712A - Production of triazolobenzodiazepines and intermediates therefor - Google Patents
Production of triazolobenzodiazepines and intermediates thereforInfo
- Publication number
- GB1476712A GB1476712A GB2473975A GB2473975A GB1476712A GB 1476712 A GB1476712 A GB 1476712A GB 2473975 A GB2473975 A GB 2473975A GB 2473975 A GB2473975 A GB 2473975A GB 1476712 A GB1476712 A GB 1476712A
- Authority
- GB
- United Kingdom
- Prior art keywords
- triazol
- benzophenone
- aminomethyl
- bis
- reacting
- 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.)
- Expired
Links
- 239000000543 intermediate Substances 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- -1 1-aminomethyl compounds Chemical class 0.000 abstract 2
- FKPVGMYRGFQUND-UHFFFAOYSA-N [2-[3,5-bis(hydroxymethyl)-1,2,4-triazol-4-yl]phenyl]-phenylmethanone Chemical compound OCC1=NN=C(CO)N1C1=CC=CC=C1C(=O)C1=CC=CC=C1 FKPVGMYRGFQUND-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- QHYNXXQYSDCYJU-UHFFFAOYSA-N (6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine Chemical class C12=CC=CC=C2N2C(CN)=NN=C2CN=C1C1=CC=CC=C1 QHYNXXQYSDCYJU-UHFFFAOYSA-N 0.000 abstract 1
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 abstract 1
- OTWAMAJHHAGCGR-UHFFFAOYSA-N 2-[[4-(2-benzoylphenyl)-5-[(1,3-dioxoisoindol-2-yl)methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound C=1C=CC=C(N2C(=NN=C2CN2C(C3=CC=CC=C3C2=O)=O)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 OTWAMAJHHAGCGR-UHFFFAOYSA-N 0.000 abstract 1
- BXBSDHSVTCGOFC-UHFFFAOYSA-N 3-amino-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=CC=C2C1(O)C1=CC=CC=C1 BXBSDHSVTCGOFC-UHFFFAOYSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 229930040373 Paraformaldehyde Natural products 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Chemical group 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229920002866 paraformaldehyde Polymers 0.000 abstract 1
- HYYFATVGUNWPOG-UHFFFAOYSA-N phenyl-[2-(1,2,4-triazol-4-yl)phenyl]methanone Chemical compound C=1C=CC=C(N2C=NN=C2)C=1C(=O)C1=CC=CC=C1 HYYFATVGUNWPOG-UHFFFAOYSA-N 0.000 abstract 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/480,980 US3947466A (en) | 1973-02-14 | 1974-06-19 | Intermediates and process for the production of certain triazolobenzodiazepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1476712A true GB1476712A (en) | 1977-06-16 |
Family
ID=23910098
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2473975A Expired GB1476712A (en) | 1974-06-19 | 1975-06-10 | Production of triazolobenzodiazepines and intermediates therefor |
| GB4635576A Expired GB1476713A (en) | 1974-06-19 | 1975-06-10 | Triazolyl benzophenones |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4635576A Expired GB1476713A (en) | 1974-06-19 | 1975-06-10 | Triazolyl benzophenones |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS518294A (https=) |
| BE (1) | BE830429A (https=) |
| CA (1) | CA1043785A (https=) |
| CH (1) | CH612435A5 (https=) |
| DE (1) | DE2526465A1 (https=) |
| FR (1) | FR2275468A1 (https=) |
| GB (2) | GB1476712A (https=) |
| NL (1) | NL7507248A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4501698A (en) * | 1983-03-31 | 1985-02-26 | The Upjohn Company | Preparing 1-(hydroxymethyl)-triazolobenzodiazepines and 1-(aminomethyl)-triazolobenzodiazepines |
-
1975
- 1975-05-22 CA CA227,603A patent/CA1043785A/en not_active Expired
- 1975-06-06 JP JP6769875A patent/JPS518294A/ja active Pending
- 1975-06-09 CH CH743275A patent/CH612435A5/xx not_active IP Right Cessation
- 1975-06-10 GB GB2473975A patent/GB1476712A/en not_active Expired
- 1975-06-10 GB GB4635576A patent/GB1476713A/en not_active Expired
- 1975-06-13 DE DE19752526465 patent/DE2526465A1/de not_active Withdrawn
- 1975-06-18 NL NL7507248A patent/NL7507248A/xx not_active Application Discontinuation
- 1975-06-18 FR FR7519140A patent/FR2275468A1/fr active Granted
- 1975-06-19 BE BE157497A patent/BE830429A/xx not_active IP Right Cessation
- 1975-09-10 JP JP10906275A patent/JPS5154598A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA1043785A (en) | 1978-12-05 |
| FR2275468B1 (https=) | 1978-09-22 |
| GB1476713A (en) | 1977-06-16 |
| FR2275468A1 (fr) | 1976-01-16 |
| JPS5154598A (ja) | 1976-05-13 |
| NL7507248A (nl) | 1975-12-23 |
| JPS518294A (en) | 1976-01-23 |
| CH612435A5 (en) | 1979-07-31 |
| AU8159575A (en) | 1976-12-02 |
| DE2526465A1 (de) | 1976-01-08 |
| BE830429A (fr) | 1975-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |