IL22721A - Benzodiazepine derivatives and process for the manufacture thereof - Google Patents
Benzodiazepine derivatives and process for the manufacture thereofInfo
- Publication number
- IL22721A IL22721A IL22721A IL2272165A IL22721A IL 22721 A IL22721 A IL 22721A IL 22721 A IL22721 A IL 22721A IL 2272165 A IL2272165 A IL 2272165A IL 22721 A IL22721 A IL 22721A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- amino
- solution
- benzodiazepin
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title claims 7
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 239000001961 anticonvulsive agent Substances 0.000 claims description 2
- 239000003158 myorelaxant agent Substances 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 31
- 239000000203 mixture Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 239000003708 ampul Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 9
- -1 hydrobroiaie Chemical class 0.000 description 9
- 239000008101 lactose Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 8
- 239000008120 corn starch Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- 239000000829 suppository Substances 0.000 description 8
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
- 239000008116 calcium stearate Substances 0.000 description 4
- 235000013539 calcium stearate Nutrition 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000011976 maleic acid Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000237858 Gastropoda Species 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005059 halophenyl group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 102220169347 rs201929423 Human genes 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F27—FURNACES; KILNS; OVENS; RETORTS
- F27D—DETAILS OR ACCESSORIES OF FURNACES, KILNS, OVENS OR RETORTS, IN SO FAR AS THEY ARE OF KINDS OCCURRING IN MORE THAN ONE KIND OF FURNACE
- F27D11/00—Arrangement of elements for electric heating in or on furnaces
- F27D11/08—Heating by electric discharge, e.g. arc discharge
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P10/00—Technologies related to metal processing
- Y02P10/10—Reduction of greenhouse gas [GHG] emissions
- Y02P10/143—Reduction of greenhouse gas [GHG] emissions of methane [CH4]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8828561A | 1961-02-10 | 1961-02-10 | |
| US11530961A | 1961-06-07 | 1961-06-07 | |
| US33986164A | 1964-01-24 | 1964-01-24 | |
| US412335A US3262938A (en) | 1961-02-10 | 1964-11-19 | Carbocyclic substituted piperidyl dioxolanes |
| US412325A US3215688A (en) | 1961-02-10 | 1964-11-19 | Certain benzodiazepine compounds |
| US416602A US3256289A (en) | 1961-02-10 | 1964-12-07 | Carbocyclic substituted piperidyl dioxanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL22721A true IL22721A (en) | 1968-09-26 |
Family
ID=27557343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL22721A IL22721A (en) | 1961-02-10 | 1965-01-04 | Benzodiazepine derivatives and process for the manufacture thereof |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US3262938A (en, 2012) |
| BE (2) | BE658797A (en, 2012) |
| CH (5) | CH405310A (en, 2012) |
| DE (3) | DE1545929A1 (en, 2012) |
| FR (3) | FR1812M (en, 2012) |
| GB (3) | GB971661A (en, 2012) |
| IL (1) | IL22721A (en, 2012) |
| NL (1) | NL141780B (en, 2012) |
| NO (1) | NO117366B (en, 2012) |
| SE (3) | SE315595B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE661945A (en, 2012) * | 1964-04-01 | |||
| US3464997A (en) * | 1966-03-17 | 1969-09-02 | Us Army | Synthesis of 3-quinuclidinol |
| US3760077A (en) * | 1969-02-18 | 1973-09-18 | Cutter Lab | Injectable compositions of the (plus)-optical isomer of the alpha racemate of 2-(2-ethyl-2-phenyl-1, -dioxolan-4-yl)piperidine and their use |
| US3856963A (en) * | 1971-10-15 | 1974-12-24 | Cutter Lab | Use of injectable compositions of the ({30 )-optional isomer of the alpha racemate of 2-(2-ethyl-2-phenyl-1,3-dioxolan-4-yl) piperidine to control pain |
| US3879406A (en) * | 1972-07-13 | 1975-04-22 | Hoffmann La Roche | Preparation of triazolobenzodiazepines |
| US4044016A (en) * | 1975-01-13 | 1977-08-23 | Hoffmann-La Roche Inc. | Preparation of triazolo benzodiazepines and novel compounds |
| DE19714041A1 (de) * | 1997-04-05 | 1998-10-08 | Henkel Kgaa | Phenonenketale |
| WO2006015683A1 (en) * | 2004-08-10 | 2006-02-16 | Merck Patent Gmbh | Liquid crystal compounds, liquid crystal medium and liquid crystal display |
| JP2008510742A (ja) * | 2004-08-24 | 2008-04-10 | ビーエーエスエフ ソシエタス・ヨーロピア | 高純度の第４級アンモニウム化合物の製造方法 |
| JP2008001596A (ja) * | 2004-09-03 | 2008-01-10 | Astellas Pharma Inc | ナトリウムチャネル阻害剤 |
| RU2334740C1 (ru) * | 2007-07-09 | 2008-09-27 | Государственное образовательное учреждение высшего профессионального образования Волгоградский государственный технический университет (ВолгГТУ) | Способ получения альфа-рацемата 1-(2-пиперидил)-1,2-этандиола |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2606909A (en) * | 1947-08-01 | 1952-08-12 | Univ Michigan | Basic dioxolanes |
| US2606907A (en) * | 1949-08-04 | 1952-08-12 | Univ Michigan | Basic dioxanes |
| DE1099540B (de) * | 1954-09-10 | 1961-02-16 | Bayer Ag | Verfahren zur Herstellung von Kondensationsprodukten |
| FR1186192A (fr) * | 1957-02-26 | 1959-08-17 | Rhone Poulenc Sa | Nouveaux pipéridyl-2 dioxolannes et leur préparation |
| US3070596A (en) * | 1959-03-23 | 1962-12-25 | Aerojet General Co | 1, 1'-biaziridine compounds and the process of preparation |
| US3121103A (en) * | 1961-10-20 | 1964-02-11 | Hoffmann La Roche | Aminobenzophenones |
-
0
- BE BE412325D patent/BE412325A/xx unknown
-
1962
- 1962-01-23 GB GB2462/62A patent/GB971661A/en not_active Expired
- 1962-02-07 FR FR887227A patent/FR1812M/fr not_active Expired
- 1962-02-10 CH CH166162A patent/CH405310A/de unknown
- 1962-04-27 FR FR895864A patent/FR1818M/fr active Active
-
1964
- 1964-11-19 US US412335A patent/US3262938A/en not_active Expired - Lifetime
- 1964-11-19 US US412325A patent/US3215688A/en not_active Expired - Lifetime
- 1964-12-07 US US416602A patent/US3256289A/en not_active Expired - Lifetime
- 1964-12-30 CH CH1330467A patent/CH460792A/de unknown
- 1964-12-30 CH CH962768A patent/CH460794A/de unknown
- 1964-12-30 CH CH1687064A patent/CH446360A/de unknown
-
1965
- 1965-01-04 IL IL22721A patent/IL22721A/en unknown
- 1965-01-04 DE DE19651545929 patent/DE1545929A1/de active Pending
- 1965-01-18 NL NL656500594A patent/NL141780B/xx unknown
- 1965-01-21 GB GB2614/65A patent/GB1043049A/en not_active Expired
- 1965-01-22 SE SE857/65A patent/SE315595B/xx unknown
- 1965-01-22 FR FR2857A patent/FR4166M/fr not_active Expired
- 1965-01-22 SE SE18131/67A patent/SE335135B/xx unknown
- 1965-01-22 SE SE18130/67A patent/SE335134B/xx unknown
- 1965-01-23 NO NO65156482A patent/NO117366B/no unknown
- 1965-01-25 BE BE658797D patent/BE658797A/xx unknown
- 1965-11-11 GB GB47936/65A patent/GB1077800A/en not_active Expired
- 1965-11-17 DE DE19651545714 patent/DE1545714A1/de active Pending
- 1965-11-17 CH CH1585965A patent/CH460774A/de unknown
- 1965-11-17 DE DE19651545713 patent/DE1545713A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR4166M (en, 2012) | 1966-05-16 |
| DE1545713A1 (de) | 1969-12-18 |
| DE1545929A1 (de) | 1969-12-18 |
| FR1818M (en, 2012) | 1963-05-13 |
| GB971661A (en) | 1964-09-30 |
| SE335134B (en, 2012) | 1971-05-17 |
| DE1445558A1 (de) | 1972-04-20 |
| BE658797A (en, 2012) | 1965-07-26 |
| CH460792A (de) | 1968-08-15 |
| NL141780B (nl) | 1974-04-16 |
| CH405310A (de) | 1966-01-15 |
| GB1077800A (en) | 1967-08-02 |
| FR1812M (en, 2012) | 1963-05-13 |
| SE315595B (en, 2012) | 1969-10-06 |
| US3215688A (en) | 1965-11-02 |
| BE412325A (en, 2012) | 1900-01-01 |
| DE1545714A1 (de) | 1969-06-26 |
| NL6500594A (en, 2012) | 1965-07-26 |
| CH460774A (de) | 1968-08-15 |
| CH446360A (de) | 1967-11-15 |
| US3262938A (en) | 1966-07-26 |
| CH460794A (de) | 1968-08-15 |
| SE335135B (en, 2012) | 1971-05-17 |
| US3256289A (en) | 1966-06-14 |
| NO117366B (en, 2012) | 1969-08-04 |
| GB1043049A (en) | 1966-09-21 |
| DE1445558B2 (de) | 1975-06-05 |
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