FI59100C - Foerbaettring foer foerfarande foer framstaellning av 12b-fenyl-8,12b-dihydro 4h-(1,3)oksatsino(3,2 d)(1,4)bentsodiazepin-4,7(6h)-dioner - Google Patents
Foerbaettring foer foerfarande foer framstaellning av 12b-fenyl-8,12b-dihydro 4h-(1,3)oksatsino(3,2 d)(1,4)bentsodiazepin-4,7(6h)-dioner Download PDFInfo
- Publication number
- FI59100C FI59100C FI750794A FI750794A FI59100C FI 59100 C FI59100 C FI 59100C FI 750794 A FI750794 A FI 750794A FI 750794 A FI750794 A FI 750794A FI 59100 C FI59100 C FI 59100C
- Authority
- FI
- Finland
- Prior art keywords
- phenyl
- diketene
- dihydro
- benzodiazepin
- foer
- Prior art date
Links
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 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
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 241000551547 Dione <red algae> Species 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000047 product Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- LLPNBWNKPILNSX-UHFFFAOYSA-N 4-methylideneoxetan-2-one propan-2-one Chemical compound CC(C)=O.C=C1CC(=O)O1 LLPNBWNKPILNSX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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
- 229960000583 acetic acid Drugs 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- -1 oxygen halides Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 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
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-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
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000002716 ataractic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling 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
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 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
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 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 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux 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
- 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12068/74A GB1479202A (en) | 1974-03-19 | 1974-03-19 | Processes for preparing oxazinobenzodiazepines |
| GB1206874 | 1974-03-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI750794A7 FI750794A7 (en, 2012) | 1975-09-20 |
| FI59100B FI59100B (fi) | 1981-02-27 |
| FI59100C true FI59100C (fi) | 1981-06-10 |
Family
ID=9997861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI750794A FI59100C (fi) | 1974-03-19 | 1975-03-18 | Foerbaettring foer foerfarande foer framstaellning av 12b-fenyl-8,12b-dihydro 4h-(1,3)oksatsino(3,2 d)(1,4)bentsodiazepin-4,7(6h)-dioner |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS50131997A (en, 2012) |
| CA (1) | CA1042429A (en, 2012) |
| CH (1) | CH592669A5 (en, 2012) |
| DE (1) | DE2512092A1 (en, 2012) |
| DK (1) | DK137648B (en, 2012) |
| FI (1) | FI59100C (en, 2012) |
| FR (1) | FR2264544B1 (en, 2012) |
| GB (1) | GB1479202A (en, 2012) |
| IE (1) | IE40884B1 (en, 2012) |
| NO (1) | NO750909L (en, 2012) |
| SE (1) | SE419756B (en, 2012) |
-
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 (en, 2012) | 1978-09-18 |
| FI59100B (fi) | 1981-02-27 |
| GB1479202A (en) | 1977-07-06 |
| FR2264544A1 (en, 2012) | 1975-10-17 |
| DK137648B (da) | 1978-04-10 |
| IE40884L (en) | 1975-09-19 |
| DE2512092A1 (de) | 1975-09-25 |
| CH592669A5 (en, 2012) | 1977-10-31 |
| IE40884B1 (en) | 1979-09-12 |
| FR2264544B1 (en, 2012) | 1978-12-01 |
| JPS50131997A (en, 2012) | 1975-10-18 |
| FI750794A7 (en, 2012) | 1975-09-20 |
| CA1042429A (en) | 1978-11-14 |
| NO750909L (en, 2012) | 1975-09-22 |
| SE7503023L (en, 2012) | 1975-09-22 |
| SE419756B (sv) | 1981-08-24 |
| DK109075A (en, 2012) | 1975-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DELMAR CHEMICALS LIMITED |