DE2512092A1 - Verfahren zur herstellung von oxazinobenzodiazepin-verbindungen - Google Patents
Verfahren zur herstellung von oxazinobenzodiazepin-verbindungenInfo
- Publication number
- DE2512092A1 DE2512092A1 DE19752512092 DE2512092A DE2512092A1 DE 2512092 A1 DE2512092 A1 DE 2512092A1 DE 19752512092 DE19752512092 DE 19752512092 DE 2512092 A DE2512092 A DE 2512092A DE 2512092 A1 DE2512092 A1 DE 2512092A1
- Authority
- DE
- Germany
- Prior art keywords
- benzodiazepine
- phenyl
- solvent
- diketene
- condensation catalyst
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 26
- AAVXHXYXRFVOQX-UHFFFAOYSA-N oxazino[3,4-i][1,2]benzodiazepine Chemical class N1=NC=CC=C2C=CC3=NOC=CC3=C21 AAVXHXYXRFVOQX-UHFFFAOYSA-N 0.000 title claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 11
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 7
- 229940049706 benzodiazepine Drugs 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical group C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ILAGJZZRKJFJNQ-UHFFFAOYSA-N 6H-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7-dione Chemical compound O1C=CC(N2CC(N=C3C(=C21)C=CC=C3)=O)=O ILAGJZZRKJFJNQ-UHFFFAOYSA-N 0.000 description 4
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- PWAJCNITSBZRBL-UHFFFAOYSA-N ketazolam Chemical compound O1C(C)=CC(=O)N2CC(=O)N(C)C3=CC=C(Cl)C=C3C21C1=CC=CC=C1 PWAJCNITSBZRBL-UHFFFAOYSA-N 0.000 description 3
- 229960004423 ketazolam Drugs 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BBQGORZUWCUBPB-UHFFFAOYSA-N 6H-1,2-benzodiazepine-4,7-dione Chemical compound N=1N=CC(C=C2C1C=CC(C2)=O)=O BBQGORZUWCUBPB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- -1 Pyridine Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12068/74A GB1479202A (en) | 1974-03-19 | 1974-03-19 | Processes for preparing oxazinobenzodiazepines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2512092A1 true DE2512092A1 (de) | 1975-09-25 |
Family
ID=9997861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752512092 Ceased DE2512092A1 (de) | 1974-03-19 | 1975-03-19 | Verfahren zur herstellung von oxazinobenzodiazepin-verbindungen |
Country Status (11)
-
1974
- 1974-03-19 GB GB12068/74A patent/GB1479202A/en not_active Expired
-
1975
- 1975-03-18 FR FR7508434A patent/FR2264544B1/fr not_active Expired
- 1975-03-18 IE IE574/75A patent/IE40884B1/xx unknown
- 1975-03-18 NO NO750909A patent/NO750909L/no unknown
- 1975-03-18 FI FI750794A patent/FI59100C/fi not_active IP Right Cessation
- 1975-03-18 SE SE7503023A patent/SE419756B/xx unknown
- 1975-03-18 DK DK109075AA patent/DK137648B/da unknown
- 1975-03-18 CA CA222,432A patent/CA1042429A/en not_active Expired
- 1975-03-19 DE DE19752512092 patent/DE2512092A1/de not_active Ceased
- 1975-03-19 JP JP50035994A patent/JPS50131997A/ja active Pending
- 1975-03-19 CH CH348475A patent/CH592669A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK137648C (enrdf_load_html_response) | 1978-09-18 |
| FI59100B (fi) | 1981-02-27 |
| GB1479202A (en) | 1977-07-06 |
| FR2264544A1 (enrdf_load_html_response) | 1975-10-17 |
| DK137648B (da) | 1978-04-10 |
| FI59100C (fi) | 1981-06-10 |
| IE40884L (en) | 1975-09-19 |
| CH592669A5 (enrdf_load_html_response) | 1977-10-31 |
| IE40884B1 (en) | 1979-09-12 |
| FR2264544B1 (enrdf_load_html_response) | 1978-12-01 |
| JPS50131997A (enrdf_load_html_response) | 1975-10-18 |
| FI750794A7 (enrdf_load_html_response) | 1975-09-20 |
| CA1042429A (en) | 1978-11-14 |
| NO750909L (enrdf_load_html_response) | 1975-09-22 |
| SE7503023L (enrdf_load_html_response) | 1975-09-22 |
| SE419756B (sv) | 1981-08-24 |
| DK109075A (enrdf_load_html_response) | 1975-09-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2919823A1 (de) | N-azidosulfonylaryl-maleinimide sowie deren verwendung | |
| DE2147023A1 (de) | Verfahren zur herstellung von 1htetrazol-verbindungen | |
| DE2453326A1 (de) | Halogensubstituierte benzimidazolonverbindungen und verfahren zu ihrer herstellung | |
| DE3782183T2 (de) | Herstellung von aromatischen polyketonen. | |
| DE69703780T2 (de) | Verfahren zur Herstellung eines eine Succinimidylgruppe enthaltenden Polyoxyalkylenderivat | |
| DE2512092A1 (de) | Verfahren zur herstellung von oxazinobenzodiazepin-verbindungen | |
| DE2321075A1 (de) | Verfahren zur herstellung von aminoverbindungen | |
| DE2855279C2 (de) | Cheliertes 1,8-Naphthyridinderivat, Verfahren zu seiner Herstellung und Verfahren zur Herstellung von 1,8-Naphthyridinderivaten | |
| DE3004700C2 (de) | Verfahren zur Herstellung von Tryptaminderivaten | |
| DE2527235A1 (de) | Verfahren zur herstellung von phenylglycinderivaten | |
| EP0198795B1 (de) | Verfahren zur Herstellung von 1,4-Diaminoanthrachinonen | |
| DE2521088A1 (de) | Diterpensaeureanilide und verfahren zu ihrer herstellung | |
| DE2240442A1 (de) | Verfahren zur herstellung von aminopenicillinen | |
| DE2252323C3 (de) | 3,6-Dialkyl-23-dihydro-2,9-dioxo-6H,9H-thiazolo [5,4-fj chinolin-e-carbonyl- Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Bakterizide | |
| DE932675C (de) | Verfahren zur Herstellung von Estern des Penicillins mit eine sekundaere Aminogruppe aufweisenden Alkoholen und von Salzen dieser Ester | |
| DE1493489C (de) | Phenyltoxolaminsalze und Verfahren zu ihrer Herstellung | |
| DE3102984A1 (de) | Verfahren zur herstellung von cysteamin-s-substituierten verbindungen und deren derivaten | |
| DE1931097C3 (de) | Verfahren zur Herstellung von 6-Isocyana to- penicillansäure derivaten | |
| DE2046848C3 (de) | Benzodiazepine und Verfahren zu ihrer Herstellung | |
| DE2119724B2 (de) | Verfahren zur herstellung einer halogensubstituierten benzoesaeure | |
| DE3410102A1 (de) | Herstellung von azinomethyl-rifamycinen | |
| AT338288B (de) | Verfahren zur herstellung neuer 7,7'-verbruckter bis-theophylline | |
| DE1940081A1 (de) | delta?-Cephem-4-carbonsaeureester | |
| EP1339697A1 (de) | Verfahren zur herstellung von phenylen-bis-benzimidazol-tetrasulfonsäure-dinatriumsalz | |
| DE2022503B2 (de) | Benzodiazepine und Verfahren zu ihrer Herste,Jung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8131 | Rejection |