JPS6019311B2 - １−〔（ジメチルアミノ）メチル〕−６−置換−４Ｈ−ｓ−トリアゾロ〔４，３−ａ〕〔１，４〕ベンゾジアゼピン類の製造方法 - Google Patents
１−〔（ジメチルアミノ）メチル〕−６−置換−４Ｈ−ｓ−トリアゾロ〔４，３−ａ〕〔１，４〕ベンゾジアゼピン類の製造方法Info
- Publication number
- JPS6019311B2 JPS6019311B2 JP51126018A JP12601876A JPS6019311B2 JP S6019311 B2 JPS6019311 B2 JP S6019311B2 JP 51126018 A JP51126018 A JP 51126018A JP 12601876 A JP12601876 A JP 12601876A JP S6019311 B2 JPS6019311 B2 JP S6019311B2
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- methyl
- dimethylamino
- penzodiazepine
- formula
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- -1 1-[(dimethylamino)methyl]-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepines Chemical class 0.000 title description 4
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 4
- 229940049706 benzodiazepine Drugs 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- FEQAUBVIUZJXKN-UHFFFAOYSA-N propan-2-imine;hydrochloride Chemical compound [Cl-].CC(C)=[NH2+] FEQAUBVIUZJXKN-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- XDAGXZXKTKRFMT-UHFFFAOYSA-N propan-2-imine Chemical compound CC(C)=N XDAGXZXKTKRFMT-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical group C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- HOLLFLKWFBXREI-UHFFFAOYSA-N propan-2-ylideneazanium;iodide Chemical compound [I-].CC(C)=[NH2+] HOLLFLKWFBXREI-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CMTIHEOOVZATEB-UHFFFAOYSA-N 1-n,1-n,1-n',1-n'-tetramethylethane-1,1-diamine Chemical compound CN(C)C(C)N(C)C CMTIHEOOVZATEB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 101150071654 CIN5 gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 229910004713 HPF6 Inorganic materials 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- YCNIBOIOWCTRCL-UHFFFAOYSA-N azane;2,2,2-trifluoroacetic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)F YCNIBOIOWCTRCL-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OXZOLXJZTSUDOM-UHFFFAOYSA-N fluoro 2,2,2-trifluoroacetate Chemical compound FOC(=O)C(F)(F)F OXZOLXJZTSUDOM-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- QGXVVZXXVJDOEM-UHFFFAOYSA-N methanimine;hydrochloride Chemical compound [Cl-].[NH2+]=C QGXVVZXXVJDOEM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- LZTIRMBLYYPMNW-UHFFFAOYSA-N propan-2-ylideneazanium;bromide Chemical compound [Br-].CC(C)=[NH2+] LZTIRMBLYYPMNW-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Classifications
-
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US623972 | 1975-10-20 | ||
| US05/623,972 US4001262A (en) | 1975-10-20 | 1975-10-20 | Process for the production of 1-[(dimethylamino)methyl]-6-phenyl-4H-triazolo[4,3-a][1,4]-benzodiazepine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5251398A JPS5251398A (en) | 1977-04-25 |
| JPS6019311B2 true JPS6019311B2 (ja) | 1985-05-15 |
Family
ID=24500089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51126018A Expired JPS6019311B2 (ja) | 1975-10-20 | 1976-10-20 | １−〔（ジメチルアミノ）メチル〕−６−置換−４Ｈ−ｓ−トリアゾロ〔４，３−ａ〕〔１，４〕ベンゾジアゼピン類の製造方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4001262A (en, 2012) |
| JP (1) | JPS6019311B2 (en, 2012) |
| BE (1) | BE847466A (en, 2012) |
| CA (1) | CA1055023A (en, 2012) |
| CH (1) | CH623314A5 (en, 2012) |
| DE (1) | DE2647177A1 (en, 2012) |
| FR (1) | FR2328708A1 (en, 2012) |
| GB (1) | GB1491667A (en, 2012) |
| MX (1) | MX3719E (en, 2012) |
| NL (1) | NL7610072A (en, 2012) |
| PL (1) | PL105275B1 (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0631404U (ja) * | 1992-09-28 | 1994-04-26 | ヤンマー農機株式会社 | 農用トラクタの作業機横移動装置 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075221A (en) * | 1977-01-24 | 1978-02-21 | The Upjohn Company | Process for preparing triazolobenzodiazepines |
| US4472397A (en) * | 1983-02-18 | 1984-09-18 | The Upjohn Company | Use of certain 1-substituted-triazolo-benzodiazepines to treat psychoses |
| US4501698A (en) * | 1983-03-31 | 1985-02-26 | The Upjohn Company | Preparing 1-(hydroxymethyl)-triazolobenzodiazepines and 1-(aminomethyl)-triazolobenzodiazepines |
| US4474699A (en) * | 1983-05-25 | 1984-10-02 | The Upjohn Company | Preparing 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepines in improved procedures |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3842090A (en) | 1973-02-14 | 1974-10-15 | Upjohn Co | Certain 1-aminomethyl-6-phenyl 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
-
1975
- 1975-10-20 US US05/623,972 patent/US4001262A/en not_active Expired - Lifetime
-
1976
- 1976-09-02 MX MX764878U patent/MX3719E/es unknown
- 1976-09-10 NL NL7610072A patent/NL7610072A/xx not_active Application Discontinuation
- 1976-09-21 CA CA261,702A patent/CA1055023A/en not_active Expired
- 1976-09-29 GB GB40338/76A patent/GB1491667A/en not_active Expired
- 1976-10-18 CH CH1318676A patent/CH623314A5/de not_active IP Right Cessation
- 1976-10-19 PL PL1976193128A patent/PL105275B1/pl unknown
- 1976-10-19 FR FR7631427A patent/FR2328708A1/fr active Granted
- 1976-10-19 DE DE19762647177 patent/DE2647177A1/de not_active Withdrawn
- 1976-10-20 BE BE171657A patent/BE847466A/xx not_active IP Right Cessation
- 1976-10-20 JP JP51126018A patent/JPS6019311B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0631404U (ja) * | 1992-09-28 | 1994-04-26 | ヤンマー農機株式会社 | 農用トラクタの作業機横移動装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH623314A5 (en, 2012) | 1981-05-29 |
| US4001262A (en) | 1977-01-04 |
| CA1055023A (en) | 1979-05-22 |
| FR2328708B3 (en, 2012) | 1980-11-07 |
| DE2647177A1 (de) | 1977-04-28 |
| BE847466A (fr) | 1977-04-20 |
| PL105275B1 (pl) | 1979-10-31 |
| FR2328708A1 (fr) | 1977-05-20 |
| JPS5251398A (en) | 1977-04-25 |
| NL7610072A (nl) | 1977-04-22 |
| MX3719E (es) | 1981-05-21 |
| GB1491667A (en) | 1977-11-09 |
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