DE1445429C3 - S-Hemisuccinoyloxy-S-phenyl- und -S-o-chlorphenyl-U-dihydro^H-Mbenzodiazepin-2-on und Verfahren zu ihrer Herstellung - Google Patents
S-Hemisuccinoyloxy-S-phenyl- und -S-o-chlorphenyl-U-dihydro^H-Mbenzodiazepin-2-on und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1445429C3 DE1445429C3 DE1445429A DEA0044280A DE1445429C3 DE 1445429 C3 DE1445429 C3 DE 1445429C3 DE 1445429 A DE1445429 A DE 1445429A DE A0044280 A DEA0044280 A DE A0044280A DE 1445429 C3 DE1445429 C3 DE 1445429C3
- Authority
- DE
- Germany
- Prior art keywords
- benzodiazepin
- dihydro
- chloro
- hemisuccinoyloxy
- phenyl
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 241000699670 Mus sp. Species 0.000 claims description 5
- 206010010904 Convulsion Diseases 0.000 claims description 4
- 230000034994 death Effects 0.000 claims description 4
- 231100000517 death Toxicity 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 claims description 3
- 239000001384 succinic acid Substances 0.000 claims description 3
- -1 amine salts Chemical class 0.000 claims description 2
- 230000001977 ataxic effect Effects 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 241000906446 Theraps Species 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000001256 tonic effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 3
- 229960004782 chlordiazepoxide Drugs 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 229960003529 diazepam Drugs 0.000 description 2
- 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 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960005181 morphine Drugs 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UPCDRADNFUWGIY-UHFFFAOYSA-N 5-methylidenetetrazole Chemical compound C=C1N=NN=N1 UPCDRADNFUWGIY-UHFFFAOYSA-N 0.000 description 1
- BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical compound C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 206010053398 Clonic convulsion Diseases 0.000 description 1
- 206010021118 Hypotonia Diseases 0.000 description 1
- DIWRORZWFLOCLC-UHFFFAOYSA-N Lorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-UHFFFAOYSA-N 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 206010043994 Tonic convulsion Diseases 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000002566 clonic effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229960004715 morphine sulfate Drugs 0.000 description 1
- GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229960004535 oxazepam Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23028362A | 1962-10-12 | 1962-10-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1445429A1 DE1445429A1 (de) | 1968-12-19 |
| DE1445429B2 DE1445429B2 (de) | 1978-04-20 |
| DE1445429C3 true DE1445429C3 (de) | 1979-02-01 |
Family
ID=22864606
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1445429A Expired DE1445429C3 (de) | 1962-10-12 | 1963-10-10 | S-Hemisuccinoyloxy-S-phenyl- und -S-o-chlorphenyl-U-dihydro^H-Mbenzodiazepin-2-on und Verfahren zu ihrer Herstellung |
| DE19631795598 Pending DE1795598A1 (de) | 1962-10-12 | 1963-10-10 | Verfahren zur Herstellung von 3-Carboxyacyloxy-5-aryl-1,2-dihydro-3H-1,4-benzodiazepin-2-on |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631795598 Pending DE1795598A1 (de) | 1962-10-12 | 1963-10-10 | Verfahren zur Herstellung von 3-Carboxyacyloxy-5-aryl-1,2-dihydro-3H-1,4-benzodiazepin-2-on |
Country Status (4)
| Country | Link |
|---|---|
| DE (2) | DE1445429C3 (OSRAM) |
| FR (1) | FR3314M (OSRAM) |
| GB (1) | GB1060463A (OSRAM) |
| SE (1) | SE310686B (OSRAM) |
-
1963
- 1963-10-10 DE DE1445429A patent/DE1445429C3/de not_active Expired
- 1963-10-10 GB GB39915/63A patent/GB1060463A/en not_active Expired
- 1963-10-10 DE DE19631795598 patent/DE1795598A1/de active Pending
- 1963-10-11 SE SE1117063A patent/SE310686B/xx unknown
-
1965
- 1965-05-17 FR FR956060A patent/FR3314M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1445429B2 (de) | 1978-04-20 |
| FR3314M (fr) | 1965-05-17 |
| GB1060463A (en) | 1967-03-01 |
| SE310686B (OSRAM) | 1969-05-12 |
| DE1795598A1 (de) | 1972-01-27 |
| DE1445429A1 (de) | 1968-12-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |