DE2265617C3 - 5-Chlor-2- [3-(aminomethyl)-5-methyl-4H-1.2.4-triazol-4-yl]-benzophenone - Google Patents
5-Chlor-2- [3-(aminomethyl)-5-methyl-4H-1.2.4-triazol-4-yl]-benzophenoneInfo
- Publication number
- DE2265617C3 DE2265617C3 DE2265617A DE2265617A DE2265617C3 DE 2265617 C3 DE2265617 C3 DE 2265617C3 DE 2265617 A DE2265617 A DE 2265617A DE 2265617 A DE2265617 A DE 2265617A DE 2265617 C3 DE2265617 C3 DE 2265617C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- chloro
- triazol
- benzophenone
- mixture
- 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
- WWADXOXMCNJJKR-UHFFFAOYSA-N [2-[3-(aminomethyl)-5-methyl-1,2,4-triazol-4-yl]-5-chlorophenyl]-phenylmethanone Chemical class CC1=NN=C(CN)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WWADXOXMCNJJKR-UHFFFAOYSA-N 0.000 title 1
- 239000012965 benzophenone Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- -1 phosphorus halides Chemical class 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
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- 238000000605 extraction Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 3
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 3
- YTBXDJDBTGZLRK-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-[1,2,4]triazolo[4,3-a]quinoline Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2C=C1C1=CC=CC=C1 YTBXDJDBTGZLRK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- BQSATKGBRPOQTI-UHFFFAOYSA-N [2-[3-(bromomethyl)-5-methyl-1,2,4-triazol-4-yl]-5-chlorophenyl]-phenylmethanone Chemical compound CC1=NN=C(CBr)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BQSATKGBRPOQTI-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 229960002715 nicotine Drugs 0.000 description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- 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 description 2
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
- FSVNVFMEUXPATP-UHFFFAOYSA-N 2,6-dichloro-4-phenylquinoline Chemical class C12=CC(Cl)=CC=C2N=C(Cl)C=C1C1=CC=CC=C1 FSVNVFMEUXPATP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- VUIFLGOWWHHEKJ-UHFFFAOYSA-N [5-chloro-2-(3-methyl-1,2,4-triazol-4-yl)phenyl]-phenylmethanone Chemical compound CC1=NN=CN1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 VUIFLGOWWHHEKJ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
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- 125000004970 halomethyl group Chemical group 0.000 description 2
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
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- 238000000034 method Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 2
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- HDPNBNXLBDFELL-UHFFFAOYSA-N 1,1,1-trimethoxyethane Chemical group COC(C)(OC)OC HDPNBNXLBDFELL-UHFFFAOYSA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000048 toxicity data Toxicity 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
- 239000002023 wood Substances 0.000 description 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
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11404971A | 1971-02-09 | 1971-02-09 | |
| US24075672A | 1972-04-03 | 1972-04-03 | |
| US00372313A US3856792A (en) | 1971-02-09 | 1973-06-21 | 2-{8 2-(substituted aminomethyl)-4h-1,2,4-triazol-4-yl{9 benzophenones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2265617B2 DE2265617B2 (de) | 1981-07-16 |
| DE2265617C3 true DE2265617C3 (de) | 1982-05-06 |
Family
ID=27381433
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2203782A Expired DE2203782C2 (de) | 1971-02-09 | 1972-01-27 | 5-Chlor-2[3-(hydroxymethyl) -5-methyl-1,2,4-triazol-4-yl]-benzophenone sowie ein Verfahren zu deren Hersellung |
| DE2265617A Expired DE2265617C3 (de) | 1971-02-09 | 1972-01-27 | 5-Chlor-2- [3-(aminomethyl)-5-methyl-4H-1.2.4-triazol-4-yl]-benzophenone |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2203782A Expired DE2203782C2 (de) | 1971-02-09 | 1972-01-27 | 5-Chlor-2[3-(hydroxymethyl) -5-methyl-1,2,4-triazol-4-yl]-benzophenone sowie ein Verfahren zu deren Hersellung |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3709898A (OSRAM) |
| JP (1) | JPS4966679A (OSRAM) |
| BE (1) | BE779144A (OSRAM) |
| BR (1) | BR7200590D0 (OSRAM) |
| CA (1) | CA966123A (OSRAM) |
| CH (2) | CH569736A5 (OSRAM) |
| DE (2) | DE2203782C2 (OSRAM) |
| DK (1) | DK513578A (OSRAM) |
| FR (1) | FR2124559B1 (OSRAM) |
| GB (4) | GB1374823A (OSRAM) |
| HK (1) | HK2580A (OSRAM) |
| NL (1) | NL151709B (OSRAM) |
| SE (1) | SE414928B (OSRAM) |
| ZA (1) | ZA7251B (OSRAM) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK139943B (da) * | 1971-06-05 | 1979-05-21 | Takeda Chemical Industries Ltd | Fremgangsmåde til fremstilling af triazolo(4,3a)(1,4)benzodiazepin-5N-oxydderivater eller syreadditionssalte deraf. |
| US3904641A (en) * | 1971-06-18 | 1975-09-09 | Yoshitomi Pharmaceutical | Triazolothienodiazepine compounds |
| BE790838A (fr) * | 1971-11-02 | 1973-04-30 | Upjohn Co | Nouvelles 1-aminophenyl-6-phenyl-s-triazolo (4,3-a) (1,4)- benzodiazepines, leur procede de preparation et medicament les contenant |
| US3842090A (en) * | 1973-02-14 | 1974-10-15 | Upjohn Co | Certain 1-aminomethyl-6-phenyl 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
| US3879413A (en) * | 1973-02-14 | 1975-04-22 | Upjohn Co | Process for the production of 6-phenyl-4-H-s-triazolo {8 4,3-a{9 {8 1,4{9 benzodiazepines |
| CA999000A (en) * | 1973-02-14 | 1976-10-26 | Jackson B. Hester (Jr.) | Process for new benzodiazepines and intermediates |
| US4263310A (en) * | 1974-03-02 | 1981-04-21 | Boehringer Ingelheim Gmbh | 8-Bromo-6-(o-chloro-phenyl)-4H-S-triazolo-[3,4,-c]-thieno-[2,3-e]-1,4-diazepines and salts thereof |
| GB1517164A (en) * | 1974-08-20 | 1978-07-12 | Roche Products Ltd | Substituted-phenyl ketones and a process for the manufacture thereof |
| US4000151A (en) * | 1974-09-11 | 1976-12-28 | The Upjohn Company | Triazolyl benzophenone compounds |
| US4000153A (en) * | 1974-09-26 | 1976-12-28 | The Upjohn Company | Triazolobenzodiazepine intermediates |
| NL7512983A (nl) * | 1974-11-06 | 1976-05-10 | Parke Davis & Co | Werkwijze voor het bereiden van diazepineverbin- dingen, werkwijze voor het bereiden van een far- maceutisch preparaat met toepassing daarvan als- mede een zo gevormd preparaat. |
| CH601267A5 (OSRAM) * | 1975-12-12 | 1978-06-30 | Ciba Geigy Ag | |
| US4075408A (en) * | 1975-09-08 | 1978-02-21 | Parke, Davis & Company | Imidazopyrazolodiazepine compounds |
| US4009175A (en) * | 1976-03-15 | 1977-02-22 | The Upjohn Company | 1-[(Aminooxy)-methyl]-6-substituted-4H-s-triazolo[4,3-a][1,4] benzodiazepines |
| US4409390A (en) * | 1981-07-23 | 1983-10-11 | Hoffmann-La Roche Inc. | Pyrrolo[3,4-D][2]Benzazepines |
| US4405518A (en) * | 1981-07-23 | 1983-09-20 | Hoffmann-La Roche Inc. | Pyrrolo[3,4-d] [2] benzazepines |
| US4375473A (en) * | 1982-01-04 | 1983-03-01 | The Upjohn Company | Method |
| US4501698A (en) * | 1983-03-31 | 1985-02-26 | The Upjohn Company | Preparing 1-(hydroxymethyl)-triazolobenzodiazepines and 1-(aminomethyl)-triazolobenzodiazepines |
| AU2015201727B2 (en) * | 2010-05-14 | 2018-03-08 | Dana-Farber Cancer Institute, Inc. | Compositions and methods for treating neoplasia, inflammatory disease and other disorders |
| CN104311562B (zh) | 2010-05-14 | 2017-07-04 | 达那-法伯癌症研究所 | 用于治疗瘤形成、炎性疾病和其他失调的组合物和方法 |
| JP6022442B2 (ja) | 2010-05-14 | 2016-11-09 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | 男性用避妊組成物および使用方法 |
| EP2569434B1 (en) | 2010-05-14 | 2019-09-04 | Dana-Farber Cancer Institute, Inc. | Compositions and methods for treating leukemia and related disorders |
| US9249161B2 (en) | 2010-12-02 | 2016-02-02 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| AR084070A1 (es) | 2010-12-02 | 2013-04-17 | Constellation Pharmaceuticals Inc | Inhibidores del bromodominio y usos de los mismos |
| US9422292B2 (en) | 2011-05-04 | 2016-08-23 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| WO2012174487A2 (en) | 2011-06-17 | 2012-12-20 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| TWI602820B (zh) | 2012-06-06 | 2017-10-21 | 星宿藥物公司 | 溴域抑制劑及其用途 |
| US9624244B2 (en) | 2012-06-06 | 2017-04-18 | Constellation Pharmaceuticals, Inc. | Benzo [B] isoxazoloazepine bromodomain inhibitors and uses thereof |
| JP2016531113A (ja) | 2013-07-25 | 2016-10-06 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | 転写因子の阻害剤およびその使用 |
| MX379463B (es) | 2013-11-08 | 2025-03-10 | Dana Farber Cancer Inst Inc | Terapia de combinación para el cáncer usando inhibidores de la proteína bromodominio y extra-terminal. |
| EP3099693A4 (en) | 2014-01-31 | 2017-08-16 | Dana-Farber Cancer Institute, Inc. | Uses of diazepane derivatives |
| CA2936865A1 (en) | 2014-01-31 | 2015-08-06 | Dana-Farber Cancer Institute, Inc. | Diaminopyrimidine benzenesulfone derivatives and uses thereof |
| WO2015131113A1 (en) | 2014-02-28 | 2015-09-03 | Tensha Therapeutics, Inc. | Treatment of conditions associated with hyperinsulinaemia |
| SI3157928T1 (sl) | 2014-06-20 | 2019-06-28 | Constellation Pharmaceuticals, Inc. | Kristalinične oblike 2-((4S)-6-(4-klorofenil)-1-metil-4H-benzo(C)izoksazolo(4,5-E)azepin-4-il acetamida |
| BR112017002369A2 (pt) | 2014-08-08 | 2017-12-05 | Dana Farber Cancer Inst Inc | derivados de diazepana e usos dos mesmos |
| CA2955077A1 (en) | 2014-08-08 | 2016-02-11 | Dana-Farber Cancer Institute, Inc. | Dihydropteridinone derivatives and uses thereof |
| MX376748B (es) | 2014-10-27 | 2025-03-07 | Tensha Therapeutics Inc | Inhibidores del bromodominio. |
| AU2016276963C1 (en) | 2015-06-12 | 2021-08-05 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
| JP2018526421A (ja) | 2015-09-11 | 2018-09-13 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | シアノチエノトリアゾロジアゼピンおよびこれらの使用 |
| BR112018004617A2 (pt) | 2015-09-11 | 2018-09-25 | Dana Farber Cancer Inst Inc | acetamida tienotriazoldiazepinas e usos das mesmas |
| CN108472295B (zh) | 2015-11-25 | 2022-04-15 | 达纳-法伯癌症研究所股份有限公司 | 二价溴结构域抑制剂及其用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3413346A (en) * | 1966-01-19 | 1968-11-26 | Hoffmann La Roche | 2-(2-haloethylamino)-5-halo-benzophenones |
| US3987052A (en) * | 1969-03-17 | 1976-10-19 | The Upjohn Company | 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
| DE1955349C2 (de) * | 1969-11-04 | 1982-01-28 | Takeda Chemical Industries, Ltd., Osaka | s-Triazolo [4,3-a] [1,4] benzodiazepine |
| YU34997B (en) * | 1970-03-27 | 1980-06-30 | Hiroyuki Tawada | Process for preparing benzodiazepine derivatives |
-
1971
- 1971-02-09 US US00114049A patent/US3709898A/en not_active Expired - Lifetime
-
1972
- 1972-01-04 ZA ZA720051A patent/ZA7251B/xx unknown
- 1972-01-05 CA CA131,732A patent/CA966123A/en not_active Expired
- 1972-01-07 GB GB82374A patent/GB1374823A/en not_active Expired
- 1972-01-07 GB GB82474A patent/GB1374824A/en not_active Expired
- 1972-01-07 GB GB82574A patent/GB1374825A/en not_active Expired
- 1972-01-07 GB GB87572A patent/GB1374822A/en not_active Expired
- 1972-01-19 CH CH78472A patent/CH569736A5/xx not_active IP Right Cessation
- 1972-01-19 CH CH1039775A patent/CH570404A5/xx not_active IP Right Cessation
- 1972-01-27 DE DE2203782A patent/DE2203782C2/de not_active Expired
- 1972-01-27 DE DE2265617A patent/DE2265617C3/de not_active Expired
- 1972-02-02 BR BR590/72*[A patent/BR7200590D0/pt unknown
- 1972-02-07 SE SE7301375A patent/SE414928B/xx unknown
- 1972-02-08 FR FR7204137A patent/FR2124559B1/fr not_active Expired
- 1972-02-09 BE BE779144A patent/BE779144A/xx not_active IP Right Cessation
- 1972-02-09 NL NL727201692A patent/NL151709B/xx not_active IP Right Cessation
-
1973
- 1973-03-28 JP JP48034757A patent/JPS4966679A/ja active Pending
-
1978
- 1978-11-17 DK DK513578A patent/DK513578A/da not_active Application Discontinuation
-
1980
- 1980-01-17 HK HK25/80A patent/HK2580A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4966679A (OSRAM) | 1974-06-27 |
| NL151709B (nl) | 1976-12-15 |
| GB1374823A (en) | 1974-11-20 |
| CA966123A (en) | 1975-04-15 |
| GB1374825A (en) | 1974-11-20 |
| SE414928B (sv) | 1980-08-25 |
| DE2203782C2 (de) | 1982-05-13 |
| HK2580A (en) | 1980-01-25 |
| GB1374822A (en) | 1974-11-20 |
| US3709898A (en) | 1973-01-09 |
| NL7201692A (OSRAM) | 1972-08-11 |
| AU3772572A (en) | 1973-07-12 |
| DE2265617B2 (de) | 1981-07-16 |
| CH569736A5 (OSRAM) | 1975-11-28 |
| DK513578A (da) | 1978-11-17 |
| CH570404A5 (OSRAM) | 1975-12-15 |
| BR7200590D0 (pt) | 1973-07-17 |
| GB1374824A (en) | 1974-11-20 |
| BE779144A (fr) | 1972-08-09 |
| FR2124559B1 (OSRAM) | 1975-08-01 |
| ZA7251B (en) | 1972-09-27 |
| FR2124559A1 (OSRAM) | 1972-09-22 |
| DE2203782A1 (de) | 1972-08-24 |
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