GB1449861A - Benzodiazepine and benzodiazocine derivatives - Google Patents
Benzodiazepine and benzodiazocine derivativesInfo
- Publication number
- GB1449861A GB1449861A GB4838973A GB4838973A GB1449861A GB 1449861 A GB1449861 A GB 1449861A GB 4838973 A GB4838973 A GB 4838973A GB 4838973 A GB4838973 A GB 4838973A GB 1449861 A GB1449861 A GB 1449861A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- bromo
- prepared
- alkyl
- alkoxy
- 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
- KZNXKMJGYSECTN-UHFFFAOYSA-N 1,2-benzodiazocine Chemical class N1=NC=CC=CC2=CC=CC=C21 KZNXKMJGYSECTN-UHFFFAOYSA-N 0.000 title abstract 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 title abstract 2
- 229940049706 benzodiazepine Drugs 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 12
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229910052731 fluorine Inorganic materials 0.000 abstract 4
- -1 mono-substituted phenyl Chemical group 0.000 abstract 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 229910052740 iodine Inorganic materials 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- RUGOFYNHMCFJFD-UHFFFAOYSA-N 1-bromo-2-(2-bromoethyl)benzene Chemical compound BrCCC1=CC=CC=C1Br RUGOFYNHMCFJFD-UHFFFAOYSA-N 0.000 abstract 2
- IOAZJPZJOSGBBZ-UHFFFAOYSA-N 1-bromo-2-(3-bromopropyl)benzene Chemical compound BrCCCC1=CC=CC=C1Br IOAZJPZJOSGBBZ-UHFFFAOYSA-N 0.000 abstract 2
- LZSYGJNFCREHMD-UHFFFAOYSA-N 1-bromo-2-(bromomethyl)benzene Chemical compound BrCC1=CC=CC=C1Br LZSYGJNFCREHMD-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 230000031709 bromination Effects 0.000 abstract 2
- 238000005893 bromination reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- CLCULGYHGFFZFI-UHFFFAOYSA-N (2-bromo-4-methylsulfanylphenyl)methanol Chemical compound BrC1=C(CO)C=CC(=C1)SC CLCULGYHGFFZFI-UHFFFAOYSA-N 0.000 abstract 1
- IOWGHQGLUMEZKG-UHFFFAOYSA-N (2-bromophenyl)methanol Chemical compound OCC1=CC=CC=C1Br IOWGHQGLUMEZKG-UHFFFAOYSA-N 0.000 abstract 1
- BWAQWLHENYXBOQ-UHFFFAOYSA-N 2-(2-bromo-4-chlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(Cl)C=C1Br BWAQWLHENYXBOQ-UHFFFAOYSA-N 0.000 abstract 1
- BVCOJESIQPNOIF-UHFFFAOYSA-N 2-(2-bromophenyl)acetonitrile Chemical compound BrC1=CC=CC=C1CC#N BVCOJESIQPNOIF-UHFFFAOYSA-N 0.000 abstract 1
- VKNQVQNYJKKCAR-UHFFFAOYSA-N 2-bromo-1-(bromomethyl)-4-methylsulfanylbenzene Chemical compound BrC1=C(CBr)C=CC(=C1)SC VKNQVQNYJKKCAR-UHFFFAOYSA-N 0.000 abstract 1
- ARQXHROFPARSPI-UHFFFAOYSA-N 2-bromo-4-methylbenzenecarbothioic S-acid Chemical compound BrC1=C(C(=S)O)C=CC(=C1)C ARQXHROFPARSPI-UHFFFAOYSA-N 0.000 abstract 1
- CEXGTXNIIFSPSF-UHFFFAOYSA-N 2-bromo-4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Br CEXGTXNIIFSPSF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- TZINKMQNKGKMHU-UHFFFAOYSA-N 3-(2-bromo-4-methylsulfanylphenyl)propan-1-ol Chemical compound BrC1=C(C=CC(=C1)SC)CCCO TZINKMQNKGKMHU-UHFFFAOYSA-N 0.000 abstract 1
- VODAJGPTULSNSU-UHFFFAOYSA-N 3-(2-bromophenyl)propan-1-ol Chemical compound OCCCC1=CC=CC=C1Br VODAJGPTULSNSU-UHFFFAOYSA-N 0.000 abstract 1
- AQBXIOGPHBWBFP-UHFFFAOYSA-N 4-amino-2-bromobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(Br)=C1 AQBXIOGPHBWBFP-UHFFFAOYSA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000010932 ethanolysis reaction Methods 0.000 abstract 1
- MZQXAVZPEZUJIJ-UHFFFAOYSA-N ethyl 2-(2-bromophenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1Br MZQXAVZPEZUJIJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29998672A | 1972-10-24 | 1972-10-24 | |
US00339258A US3825549A (en) | 1972-10-24 | 1973-03-08 | Certain dihydropyrido(2,1-b)(1,3)benzodi-azepines and benzodiazocines |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1449861A true GB1449861A (en) | 1976-09-15 |
Family
ID=26971513
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB4838973A Expired GB1449861A (en) | 1972-10-24 | 1973-10-17 | Benzodiazepine and benzodiazocine derivatives |
Country Status (6)
Country | Link |
---|---|
US (1) | US3825549A (enrdf_load_stackoverflow) |
JP (1) | JPS4975595A (enrdf_load_stackoverflow) |
CA (1) | CA1016167A (enrdf_load_stackoverflow) |
DE (2) | DE2352918A1 (enrdf_load_stackoverflow) |
FR (1) | FR2203640B1 (enrdf_load_stackoverflow) |
GB (1) | GB1449861A (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3150522A1 (de) * | 1981-09-24 | 1983-04-07 | A. H. Robins Co. Inc., 23220 Richmond, Va. | Phenyl-substituierte pyrido (1,4) benzodiazepine, zwischenstufen und verfahren zu ihrer herstellung, und ihre verwendung als antidepressiva |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ZA86171B (en) * | 1985-01-16 | 1986-08-27 | Hoffmann La Roche | Polycyclic salts |
US4990648A (en) * | 1988-12-22 | 1991-02-05 | Ici Americas Inc. | Process for producing an alkylthiobenzoate |
US4925970A (en) * | 1988-12-22 | 1990-05-15 | Brown Richard W | Process for producing cyclohexadiene thioether |
-
1973
- 1973-03-08 US US00339258A patent/US3825549A/en not_active Expired - Lifetime
- 1973-10-09 CA CA182,816A patent/CA1016167A/en not_active Expired
- 1973-10-17 GB GB4838973A patent/GB1449861A/en not_active Expired
- 1973-10-22 DE DE19732352918 patent/DE2352918A1/de active Pending
- 1973-10-22 DE DE2365309*A patent/DE2365309A1/de active Pending
- 1973-10-24 JP JP48119816A patent/JPS4975595A/ja active Pending
- 1973-10-24 FR FR7337914A patent/FR2203640B1/fr not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3150522A1 (de) * | 1981-09-24 | 1983-04-07 | A. H. Robins Co. Inc., 23220 Richmond, Va. | Phenyl-substituierte pyrido (1,4) benzodiazepine, zwischenstufen und verfahren zu ihrer herstellung, und ihre verwendung als antidepressiva |
Also Published As
Publication number | Publication date |
---|---|
CA1016167A (en) | 1977-08-23 |
FR2203640A1 (enrdf_load_stackoverflow) | 1974-05-17 |
JPS4975595A (enrdf_load_stackoverflow) | 1974-07-20 |
DE2365309A1 (de) | 1974-05-30 |
FR2203640B1 (enrdf_load_stackoverflow) | 1978-07-28 |
DE2352918A1 (de) | 1974-05-02 |
US3825549A (en) | 1974-07-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |