DE2228044A1 - 1,6 disubstituierte 4H s Triazolo eckige Klammer auf 4,3 a eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepine, deren N Oxide und deren pharmazeutisch vertraglichen Salze sowie Verfahren zu ihrer Herstellung - Google Patents
1,6 disubstituierte 4H s Triazolo eckige Klammer auf 4,3 a eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepine, deren N Oxide und deren pharmazeutisch vertraglichen Salze sowie Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2228044A1 DE2228044A1 DE19722228044 DE2228044A DE2228044A1 DE 2228044 A1 DE2228044 A1 DE 2228044A1 DE 19722228044 DE19722228044 DE 19722228044 DE 2228044 A DE2228044 A DE 2228044A DE 2228044 A1 DE2228044 A1 DE 2228044A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- formula
- triazolo
- compound
- 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
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- 150000003839 salts Chemical class 0.000 title claims description 16
- 229940049706 benzodiazepine Drugs 0.000 title claims description 11
- 150000001557 benzodiazepines Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 cycloalkyl radical Chemical group 0.000 claims description 44
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
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- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- 125000004076 pyridyl group Chemical group 0.000 claims 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 22
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- HEOUXFGHVMLUNY-UHFFFAOYSA-N 5-phenyl-1,4-benzodiazepine-2-thione Chemical class C1(=CC=CC=C1)C=1N=CC(N=C2C1C=CC=C2)=S HEOUXFGHVMLUNY-UHFFFAOYSA-N 0.000 description 2
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- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004467 fishmeal Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 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
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 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
- 235000013379 molasses Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 229940073020 nitrol Drugs 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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 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
- 239000000843 powder Substances 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 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
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15467471A | 1971-06-18 | 1971-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2228044A1 true DE2228044A1 (de) | 1972-12-21 |
Family
ID=22552280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722228044 Pending DE2228044A1 (de) | 1971-06-18 | 1972-06-09 | 1,6 disubstituierte 4H s Triazolo eckige Klammer auf 4,3 a eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepine, deren N Oxide und deren pharmazeutisch vertraglichen Salze sowie Verfahren zu ihrer Herstellung |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU456537B2 (enExample) |
| BE (1) | BE785023A (enExample) |
| CH (1) | CH579567A5 (enExample) |
| DE (1) | DE2228044A1 (enExample) |
| FR (1) | FR2142053B1 (enExample) |
| GB (1) | GB1332766A (enExample) |
| NL (1) | NL7208036A (enExample) |
| ZA (1) | ZA723636B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199588A (en) * | 1974-03-02 | 1980-04-22 | Boehringer Ingelheim Gmbh | 6-Phenyl-4H-s-triazolo-[3,4c]-thieno-[2,3e]-1,4-diazepines and salts thereof |
| DE3516214A1 (de) * | 1984-05-15 | 1985-11-21 | Hitachi Metals, Ltd., Tokio/Tokyo | Geraet zum pruefen der haerte von eisenteilen |
| EP0255028A3 (de) * | 1986-07-25 | 1990-03-21 | Boehringer Ingelheim Kg | Neue 1,4-Benzodiazepine, ihre Herstellung und Verwendung als PAF Antagonisten |
-
1972
- 1972-05-03 GB GB2065672A patent/GB1332766A/en not_active Expired
- 1972-05-09 AU AU42838/72A patent/AU456537B2/en not_active Expired
- 1972-05-26 ZA ZA723636A patent/ZA723636B/xx unknown
- 1972-06-09 DE DE19722228044 patent/DE2228044A1/de active Pending
- 1972-06-13 NL NL7208036A patent/NL7208036A/xx not_active Application Discontinuation
- 1972-06-16 FR FR7221905A patent/FR2142053B1/fr not_active Expired
- 1972-06-16 BE BE785023A patent/BE785023A/xx not_active IP Right Cessation
- 1972-06-16 CH CH903572A patent/CH579567A5/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4199588A (en) * | 1974-03-02 | 1980-04-22 | Boehringer Ingelheim Gmbh | 6-Phenyl-4H-s-triazolo-[3,4c]-thieno-[2,3e]-1,4-diazepines and salts thereof |
| DE3516214A1 (de) * | 1984-05-15 | 1985-11-21 | Hitachi Metals, Ltd., Tokio/Tokyo | Geraet zum pruefen der haerte von eisenteilen |
| EP0255028A3 (de) * | 1986-07-25 | 1990-03-21 | Boehringer Ingelheim Kg | Neue 1,4-Benzodiazepine, ihre Herstellung und Verwendung als PAF Antagonisten |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2142053B1 (enExample) | 1976-03-05 |
| GB1332766A (en) | 1973-10-03 |
| NL7208036A (enExample) | 1972-12-20 |
| CH579567A5 (enExample) | 1976-09-15 |
| BE785023A (fr) | 1972-12-18 |
| FR2142053A1 (enExample) | 1973-01-26 |
| AU456537B2 (en) | 1974-12-03 |
| ZA723636B (en) | 1973-04-25 |
| AU4283872A (en) | 1973-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |