DE2220615A1 - Neue 1-substituierte 6-Phenyl-4H-s-triazolo-[4,3-a][1,4]-benzodiazepine und Verfahren zu deren Herstellung - Google Patents
Neue 1-substituierte 6-Phenyl-4H-s-triazolo-[4,3-a][1,4]-benzodiazepine und Verfahren zu deren HerstellungInfo
- Publication number
- DE2220615A1 DE2220615A1 DE19722220615 DE2220615A DE2220615A1 DE 2220615 A1 DE2220615 A1 DE 2220615A1 DE 19722220615 DE19722220615 DE 19722220615 DE 2220615 A DE2220615 A DE 2220615A DE 2220615 A1 DE2220615 A1 DE 2220615A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- triazolo
- chloro
- benzodiazepine
- radical
- 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.)
- Withdrawn
Links
- -1 1-substituted 6-phenyl-4H-s-triazolo- [4,3-a] [1,4] -benzodiazepines Chemical class 0.000 title claims description 51
- 238000000034 method Methods 0.000 title claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 19
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 13
- 229940049706 benzodiazepine Drugs 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000004248 saffron Substances 0.000 description 1
- 235000013974 saffron Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical class OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13827871A | 1971-04-28 | 1971-04-28 | |
| US20120771A | 1971-11-22 | 1971-11-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2220615A1 true DE2220615A1 (de) | 1972-11-16 |
Family
ID=26836045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722220615 Withdrawn DE2220615A1 (de) | 1971-04-28 | 1972-04-27 | Neue 1-substituierte 6-Phenyl-4H-s-triazolo-[4,3-a][1,4]-benzodiazepine und Verfahren zu deren Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5541235B1 (enrdf_load_stackoverflow) |
| BE (1) | BE782680A (enrdf_load_stackoverflow) |
| CH (1) | CH571518A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2220615A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2134625B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1331015A (enrdf_load_stackoverflow) |
| NL (2) | NL7205705A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4427590A (en) | 1970-11-23 | 1984-01-24 | Ciba-Geigy Corporation | Triazolobenzodiazepine derivatives |
| US4902794A (en) * | 1971-04-28 | 1990-02-20 | The Upjohn Company | Triazolo-benzodiazepines |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54119499A (en) * | 1978-03-09 | 1979-09-17 | Shionogi & Co Ltd | Triazolobenzodiazepin derivative |
| US4455307A (en) * | 1982-01-04 | 1984-06-19 | The Upjohn Company | Antihypertensive use of triazolobenzodiazepines |
| DE3332830A1 (de) * | 1982-09-16 | 1984-03-22 | The Upjohn Co., 49001 Kalamazoo, Mich. | Verwendung von benzodiazepinen zur bekaempfung oder bei der behandlung von panikzustaenden |
| US4476134A (en) * | 1983-08-01 | 1984-10-09 | The Upjohn Company | Process for treating panic disorders |
| US4588721A (en) * | 1983-09-12 | 1986-05-13 | The Upjohn Company | Treatment of negative symptoms of schizophrenia |
| JPS6144523A (ja) * | 1984-08-06 | 1986-03-04 | Nippon Steel Corp | 鋼片の切断装置 |
| JPS61100311A (ja) * | 1984-10-18 | 1986-05-19 | Kawasaki Steel Corp | 溶接機における切断装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987052A (en) * | 1969-03-17 | 1976-10-19 | The Upjohn Company | 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| JPS4932874B1 (enrdf_load_stackoverflow) * | 1970-12-11 | 1974-09-03 |
-
1972
- 1972-03-29 GB GB1487972A patent/GB1331015A/en not_active Expired
- 1972-04-20 JP JP3919072A patent/JPS5541235B1/ja active Pending
- 1972-04-21 CH CH596372A patent/CH571518A5/xx not_active IP Right Cessation
- 1972-04-26 BE BE782680A patent/BE782680A/xx not_active IP Right Cessation
- 1972-04-27 DE DE19722220615 patent/DE2220615A1/de not_active Withdrawn
- 1972-04-27 NL NL7205705A patent/NL7205705A/xx unknown
- 1972-04-27 FR FR7215118A patent/FR2134625B1/fr not_active Expired
-
1981
- 1981-12-23 NL NL8105804A patent/NL8105804A/nl not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| In Betracht gezogene ältere Anmeldung: DE-OS 22 01 210 DE-OS 21 59 242 DE-OS 21 56 472 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4427590A (en) | 1970-11-23 | 1984-01-24 | Ciba-Geigy Corporation | Triazolobenzodiazepine derivatives |
| US4902794A (en) * | 1971-04-28 | 1990-02-20 | The Upjohn Company | Triazolo-benzodiazepines |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2134625B1 (enrdf_load_stackoverflow) | 1975-10-17 |
| BE782680A (fr) | 1972-10-26 |
| JPS5541235B1 (enrdf_load_stackoverflow) | 1980-10-22 |
| NL8105804A (nl) | 1982-04-01 |
| GB1331015A (en) | 1973-09-19 |
| NL7205705A (enrdf_load_stackoverflow) | 1972-10-31 |
| FR2134625A1 (enrdf_load_stackoverflow) | 1972-12-08 |
| CH571518A5 (enrdf_load_stackoverflow) | 1976-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal | ||
| 8178 | Suspension cancelled |