NO117366B - - Google Patents
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- Publication number
- NO117366B NO117366B NO65156482A NO15648265A NO117366B NO 117366 B NO117366 B NO 117366B NO 65156482 A NO65156482 A NO 65156482A NO 15648265 A NO15648265 A NO 15648265A NO 117366 B NO117366 B NO 117366B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- benzodiazepine
- dihydro
- amino
- chloramine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 18
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- RISAYBIQCQEAKJ-UHFFFAOYSA-N 1-amino-7-chloro-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound NN1C(CN=C(C2=C1C=CC(=C2)Cl)C2=CC=CC=C2)=O RISAYBIQCQEAKJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 2
- 150000001557 benzodiazepines Chemical class 0.000 claims description 2
- CHIFCDOIPRCHCF-UHFFFAOYSA-N delorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl CHIFCDOIPRCHCF-UHFFFAOYSA-N 0.000 claims description 2
- KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 claims description 2
- AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- -1 1,5-disubstituted 1,3-dihydro-2H-1,4-benzodiazepine-2-ones Chemical class 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- MRGGNQYAUKLLPN-UHFFFAOYSA-N 1-amino-7-chloro-5-(2-chlorophenyl)-3H-1,4-benzodiazepin-2-one Chemical compound NN1C(CN=C(C2=C1C=CC(=C2)Cl)C2=C(C=CC=C2)Cl)=O MRGGNQYAUKLLPN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- 238000010828 elution Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- UZPKYYPVIUHYNR-UHFFFAOYSA-N 1-amino-7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(N)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 UZPKYYPVIUHYNR-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- RXBKPDNCXZSXJM-UHFFFAOYSA-N [N+](=O)([O-])C=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1 Chemical compound [N+](=O)([O-])C=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=CC=C2)C1 RXBKPDNCXZSXJM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- GGRWZBVSUZZMKS-UHFFFAOYSA-N demoxepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C[N+]([O-])=C1C1=CC=CC=C1 GGRWZBVSUZZMKS-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (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 |
|---|---|
| NO117366B true NO117366B (ru) | 1969-08-04 |
Family
ID=27557343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO65156482A NO117366B (ru) | 1961-02-10 | 1965-01-23 |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US3262938A (ru) |
| BE (2) | BE658797A (ru) |
| CH (5) | CH405310A (ru) |
| DE (3) | DE1545929A1 (ru) |
| FR (3) | FR1812M (ru) |
| GB (3) | GB971661A (ru) |
| IL (1) | IL22721A (ru) |
| NL (1) | NL141780B (ru) |
| NO (1) | NO117366B (ru) |
| SE (3) | SE335135B (ru) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE661945A (ru) * | 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 |
| ATE410496T1 (de) * | 2004-08-10 | 2008-10-15 | Merck Patent Gmbh | Flüssigkristallverbindungen, flüssigkristallmedium und flüssigkristallanzeige |
| CN101006046A (zh) * | 2004-08-24 | 2007-07-25 | 巴斯福股份公司 | 制备高纯度季铵化合物的方法 |
| JP2008001596A (ja) * | 2004-09-03 | 2008-01-10 | Astellas Pharma Inc | ナトリウムチャネル阻害剤 |
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 |
| US3121075A (en) * | 1961-10-20 | 1964-02-11 | Hoffmann La Roche | Aminobenzodiazepines |
-
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 active Active
- 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 CH962768A patent/CH460794A/de unknown
- 1964-12-30 CH CH1687064A patent/CH446360A/de unknown
- 1964-12-30 CH CH1330467A patent/CH460792A/de unknown
-
1965
- 1965-01-04 DE DE19651545929 patent/DE1545929A1/de active Pending
- 1965-01-04 IL IL22721A patent/IL22721A/en unknown
- 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 SE18131/67A patent/SE335135B/xx unknown
- 1965-01-22 FR FR2857A patent/FR4166M/fr not_active Expired
- 1965-01-22 SE SE18130/67A patent/SE335134B/xx unknown
- 1965-01-22 SE SE857/65A patent/SE315595B/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 |
|---|---|
| BE412325A (ru) | 1900-01-01 |
| IL22721A (en) | 1968-09-26 |
| DE1545713A1 (de) | 1969-12-18 |
| CH460774A (de) | 1968-08-15 |
| US3256289A (en) | 1966-06-14 |
| FR1818M (ru) | 1963-05-13 |
| DE1445558A1 (de) | 1972-04-20 |
| US3262938A (en) | 1966-07-26 |
| GB971661A (en) | 1964-09-30 |
| FR4166M (ru) | 1966-05-16 |
| DE1445558B2 (de) | 1975-06-05 |
| US3215688A (en) | 1965-11-02 |
| FR1812M (ru) | 1963-05-13 |
| SE335134B (ru) | 1971-05-17 |
| SE335135B (ru) | 1971-05-17 |
| DE1545929A1 (de) | 1969-12-18 |
| SE315595B (ru) | 1969-10-06 |
| GB1043049A (en) | 1966-09-21 |
| GB1077800A (en) | 1967-08-02 |
| CH460794A (de) | 1968-08-15 |
| NL141780B (nl) | 1974-04-16 |
| CH460792A (de) | 1968-08-15 |
| CH405310A (de) | 1966-01-15 |
| DE1545714A1 (de) | 1969-06-26 |
| CH446360A (de) | 1967-11-15 |
| BE658797A (ru) | 1965-07-26 |
| NL6500594A (ru) | 1965-07-26 |
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