DE1238479B - Verfahren zur Herstellung von 5, 6-Dihydro-5-oxo-11H-pyrido-[2, 3-b] [1, 5]-benzodiazepinen - Google Patents
Verfahren zur Herstellung von 5, 6-Dihydro-5-oxo-11H-pyrido-[2, 3-b] [1, 5]-benzodiazepinenInfo
- Publication number
- DE1238479B DE1238479B DET25507A DET0025507A DE1238479B DE 1238479 B DE1238479 B DE 1238479B DE T25507 A DET25507 A DE T25507A DE T0025507 A DET0025507 A DE T0025507A DE 1238479 B DE1238479 B DE 1238479B
- Authority
- DE
- Germany
- Prior art keywords
- pyrido
- dihydro
- oxo
- general formula
- benzodiazepines
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- SFRAVXBSPHJEBZ-UHFFFAOYSA-N 6,11-dihydropyrido[3,2-c][1,5]benzodiazepin-5-one Chemical class O=C1NC2=CC=CC=C2NC2=NC=CC=C12 SFRAVXBSPHJEBZ-UHFFFAOYSA-N 0.000 title 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 claims description 4
- 229940049706 benzodiazepine Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001557 benzodiazepines Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- NJVCEFNGEYMKSL-UHFFFAOYSA-N 11h-pyrido[2,3-b][1,5]benzodiazepine Chemical compound N1=CC2=CC=CN=C2NC2=CC=CC=C21 NJVCEFNGEYMKSL-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
- MHQULXYNBKWNDF-UHFFFAOYSA-N 3,4-dimethylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1C MHQULXYNBKWNDF-UHFFFAOYSA-N 0.000 description 1
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LCSCTFTVNQPHTC-UHFFFAOYSA-N n-(2-aminophenyl)-2-chloropyridine-3-carboxamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl LCSCTFTVNQPHTC-UHFFFAOYSA-N 0.000 description 1
- 150000004987 o-phenylenediamines Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET25507A DE1238479B (de) | 1964-01-28 | 1964-01-28 | Verfahren zur Herstellung von 5, 6-Dihydro-5-oxo-11H-pyrido-[2, 3-b] [1, 5]-benzodiazepinen |
| FR1618A FR1434202A (fr) | 1964-01-28 | 1965-01-12 | Procédé pour obtenir des nouvelles 5, 6-dihydro-5-oxo-11eta-pyrido [2, 3-b] [1, 5] benzodiazépines |
| US427503A US3316251A (en) | 1964-01-28 | 1965-01-22 | 5, 6-dihydro-5-oxo-11h-pyrido-[2, 3-b][1, 5]-benzodiazepine derivatives and process |
| CH109465A CH438346A (de) | 1964-01-28 | 1965-01-26 | Verfahren zur Herstellung von neuen 5,6-Dihydro-5-oxo-11H-pyrido (2,3-b) (1,5) benzodiazepinen |
| GB361265A GB1050554A (en, 2012) | 1964-01-28 | 1965-01-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET25507A DE1238479B (de) | 1964-01-28 | 1964-01-28 | Verfahren zur Herstellung von 5, 6-Dihydro-5-oxo-11H-pyrido-[2, 3-b] [1, 5]-benzodiazepinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1238479B true DE1238479B (de) | 1967-04-13 |
Family
ID=7552122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DET25507A Pending DE1238479B (de) | 1964-01-28 | 1964-01-28 | Verfahren zur Herstellung von 5, 6-Dihydro-5-oxo-11H-pyrido-[2, 3-b] [1, 5]-benzodiazepinen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3316251A (en, 2012) |
| CH (1) | CH438346A (en, 2012) |
| DE (1) | DE1238479B (en, 2012) |
| FR (1) | FR1434202A (en, 2012) |
| GB (1) | GB1050554A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1156781A (en) * | 1965-04-07 | 1969-07-02 | Lab U P S A | New Heterocyclic Compounds |
| US3530116A (en) * | 1967-08-21 | 1970-09-22 | Merck & Co Inc | 3(4h)-oxo-2h-thiaxantheno (9,9alpha,1-ef)-1,4-diazepin-8,8-dioxides |
| US3518254A (en) * | 1967-11-09 | 1970-06-30 | American Home Prod | Synthesis of 1,3-diazepino(1,2-a)indolin-1(2h)-ones |
| FI50242C (fi) * | 1969-07-18 | 1976-01-12 | Thomae Gmbh Dr K | Menetelmä valmistaa farmakologisesti aktiivisia uusia diallyyliaminoal kanoyylidibenso- tai pyridobenso-diatsepiineja ja niiden happoadditios uoloja. |
| IT1212039B (it) * | 1987-10-30 | 1989-11-08 | Dompe Farmaceutici | Procedimento di preparazione di priridobenzodiazepinone |
| FR2850654A1 (fr) * | 2003-02-03 | 2004-08-06 | Servier Lab | Nouveaux derives d'azepines tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
-
1964
- 1964-01-28 DE DET25507A patent/DE1238479B/de active Pending
-
1965
- 1965-01-12 FR FR1618A patent/FR1434202A/fr not_active Expired
- 1965-01-22 US US427503A patent/US3316251A/en not_active Expired - Lifetime
- 1965-01-26 CH CH109465A patent/CH438346A/de unknown
- 1965-01-27 GB GB361265A patent/GB1050554A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| CH438346A (de) | 1967-06-30 |
| GB1050554A (en, 2012) | 1966-12-07 |
| FR1434202A (fr) | 1966-04-08 |
| US3316251A (en) | 1967-04-25 |
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