JPS58225074A - ジベンゾオキサゼピン誘導体 - Google Patents
ジベンゾオキサゼピン誘導体Info
- Publication number
- JPS58225074A JPS58225074A JP10851682A JP10851682A JPS58225074A JP S58225074 A JPS58225074 A JP S58225074A JP 10851682 A JP10851682 A JP 10851682A JP 10851682 A JP10851682 A JP 10851682A JP S58225074 A JPS58225074 A JP S58225074A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- lower alkyl
- acid
- 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.)
- Granted
Links
- 150000007655 dibenzoazepines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 6
- 150000004820 halides Chemical class 0.000 abstract description 3
- -1 4-methylpiperazinyl Chemical group 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000003699 antiulcer agent Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- HPYONZVIPMACEZ-UHFFFAOYSA-N n-methylpiperazine-1-carboxamide Chemical compound CNC(=O)N1CCNCC1 HPYONZVIPMACEZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 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
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10851682A JPS58225074A (ja) | 1982-06-25 | 1982-06-25 | ジベンゾオキサゼピン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10851682A JPS58225074A (ja) | 1982-06-25 | 1982-06-25 | ジベンゾオキサゼピン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58225074A true JPS58225074A (ja) | 1983-12-27 |
| JPH0359068B2 JPH0359068B2 (enrdf_load_stackoverflow) | 1991-09-09 |
Family
ID=14486768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10851682A Granted JPS58225074A (ja) | 1982-06-25 | 1982-06-25 | ジベンゾオキサゼピン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58225074A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10183936B2 (en) | 2014-03-13 | 2019-01-22 | Indiana University Research And Technology Corporation | Hepatitis B core protein allosteric modulators |
| US10377748B2 (en) | 2015-09-15 | 2019-08-13 | Assembly Biosciences, Inc. | Hepatitis B core protein modulators |
| US10987360B2 (en) | 2016-09-15 | 2021-04-27 | Assembly Biosciences, Inc. | Hepatitis B core protein modulators |
| US11040965B2 (en) | 2017-03-13 | 2021-06-22 | Assembly Biosciences, Inc. | Process for making Hepatitis B core protein modulators |
| US11078170B2 (en) | 2017-03-02 | 2021-08-03 | Assembly Biosciences, Inc. | Cyclic sulfamide compounds and methods of using same |
| US11649218B2 (en) * | 2018-03-09 | 2023-05-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | C-Abl tyrosine kinase inhibitory compound embodiments and methods of making and using the same |
-
1982
- 1982-06-25 JP JP10851682A patent/JPS58225074A/ja active Granted
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10183936B2 (en) | 2014-03-13 | 2019-01-22 | Indiana University Research And Technology Corporation | Hepatitis B core protein allosteric modulators |
| AU2015229174B2 (en) * | 2014-03-13 | 2019-04-11 | Assembly Biosciences, Inc. | Hepatitis B core protein allosteric modulators |
| US10947224B2 (en) | 2014-03-13 | 2021-03-16 | Indiana University Research And Technology Corporation | Hepatitis B core protein allosteric modulators |
| US10377748B2 (en) | 2015-09-15 | 2019-08-13 | Assembly Biosciences, Inc. | Hepatitis B core protein modulators |
| US10392379B2 (en) | 2015-09-15 | 2019-08-27 | Assembly Biosciences, Inc. | Hepatitis B core protein modulators |
| US10766890B2 (en) | 2015-09-15 | 2020-09-08 | Assembly Biosciences, Inc. | Hepatitis B core protein modulators |
| US10968211B2 (en) | 2015-09-15 | 2021-04-06 | Assembly Biosciences, Inc. | Hepatitis B core protein modulators |
| US11814376B2 (en) | 2015-09-15 | 2023-11-14 | Assembly Biosciences, Inc. | Hepatitis b core protein modulators |
| US10987360B2 (en) | 2016-09-15 | 2021-04-27 | Assembly Biosciences, Inc. | Hepatitis B core protein modulators |
| US11078170B2 (en) | 2017-03-02 | 2021-08-03 | Assembly Biosciences, Inc. | Cyclic sulfamide compounds and methods of using same |
| US11040965B2 (en) | 2017-03-13 | 2021-06-22 | Assembly Biosciences, Inc. | Process for making Hepatitis B core protein modulators |
| US11649218B2 (en) * | 2018-03-09 | 2023-05-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | C-Abl tyrosine kinase inhibitory compound embodiments and methods of making and using the same |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0359068B2 (enrdf_load_stackoverflow) | 1991-09-09 |
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