NO123037B - - Google Patents
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- Publication number
- NO123037B NO123037B NO1012/68A NO101268A NO123037B NO 123037 B NO123037 B NO 123037B NO 1012/68 A NO1012/68 A NO 1012/68A NO 101268 A NO101268 A NO 101268A NO 123037 B NO123037 B NO 123037B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- compounds
- compound
- chloro
- reaction
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- -1 chlorobenzene Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- HQMWRXORWPOELC-UHFFFAOYSA-N 2-[amino(phenyl)methyl]-4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1C(N)C1=CC=CC=C1 HQMWRXORWPOELC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229940075930 picrate Drugs 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- HKQCJJOXYWQRFN-UHFFFAOYSA-N 1-bromo-2-iodoethane Chemical compound BrCCI HKQCJJOXYWQRFN-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LZIPBJBQQPZLOR-UHFFFAOYSA-N 2-(4-methylphenyl)sulfonyloxyethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOS(=O)(=O)C1=CC=C(C)C=C1 LZIPBJBQQPZLOR-UHFFFAOYSA-N 0.000 description 1
- YIBUYDHSWMGPBG-UHFFFAOYSA-N 2-(benzenecarboximidoyl)-4-chloro-n-methylaniline Chemical compound CNC1=CC=C(Cl)C=C1C(=N)C1=CC=CC=C1 YIBUYDHSWMGPBG-UHFFFAOYSA-N 0.000 description 1
- QNIUWWCDBYUWGZ-UHFFFAOYSA-N 2-(benzenecarboximidoyl)-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1C(=N)C1=CC=CC=C1 QNIUWWCDBYUWGZ-UHFFFAOYSA-N 0.000 description 1
- LLHMWTOYUSTYGU-UHFFFAOYSA-N 2-(benzenesulfonyloxy)ethyl benzenesulfonate Chemical compound C=1C=CC=CC=1S(=O)(=O)OCCOS(=O)(=O)C1=CC=CC=C1 LLHMWTOYUSTYGU-UHFFFAOYSA-N 0.000 description 1
- TXTPIGYQTSOFKF-UHFFFAOYSA-N 2-[amino(phenyl)methyl]-4-chloroaniline Chemical compound C=1C(Cl)=CC=C(N)C=1C(N)C1=CC=CC=C1 TXTPIGYQTSOFKF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- QSQFARNGNIZGAW-UHFFFAOYSA-N 2-methylsulfonyloxyethyl methanesulfonate Chemical compound CS(=O)(=O)OCCOS(C)(=O)=O QSQFARNGNIZGAW-UHFFFAOYSA-N 0.000 description 1
- JSGMWVLRXAWFMH-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-2,3,4,5-tetrahydro-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N(C)CCNC1C1=CC=CC=C1 JSGMWVLRXAWFMH-UHFFFAOYSA-N 0.000 description 1
- NATUZYQEBYZLOV-UHFFFAOYSA-N 7-chloro-5-phenyl-2,3,4,5-tetrahydro-1h-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2NCCNC1C1=CC=CC=C1 NATUZYQEBYZLOV-UHFFFAOYSA-N 0.000 description 1
- JZWOKDTXYPEJEW-UHFFFAOYSA-N 7-chloro-5-phenyl-2,3-dihydro-1h-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2NCCN=C1C1=CC=CC=C1 JZWOKDTXYPEJEW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YLCXGBZIZBEVPZ-UHFFFAOYSA-N Medazepam Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=CC=CC=C1 YLCXGBZIZBEVPZ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MWSXNVQQPNIIEQ-UHFFFAOYSA-N n-[[5-chloro-2-(methylamino)phenyl]-phenylmethylidene]hydroxylamine Chemical compound CNC1=CC=C(Cl)C=C1C(=NO)C1=CC=CC=C1 MWSXNVQQPNIIEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62383467A | 1967-03-17 | 1967-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123037B true NO123037B (US20100268047A1-20101021-C00003.png) | 1971-09-20 |
Family
ID=24499574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1012/68A NO123037B (US20100268047A1-20101021-C00003.png) | 1967-03-17 | 1968-03-15 |
Country Status (16)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3817984A (en) * | 1969-07-08 | 1974-06-18 | Sumitomo Chemical Co | Process for producing benzodiazepine derivatives |
| FR2054476A1 (en) * | 1969-07-09 | 1971-04-23 | Sumitomo Chemical Co | Dihydro benzodiazpine derivs with tranqui- - lising, muscle-relaxant, antispasmodic and |
| BE785937A (fr) * | 1971-07-08 | 1973-01-08 | Sandoz Sa | Nouveaux derives de la quinazoline, leur preparation et leur application comme medicaments |
| JPS6019753A (ja) * | 1983-07-13 | 1985-01-31 | Shionogi & Co Ltd | オルト−（モノ置換アミノ）フエニルイミン類およびその製造法 |
-
1967
- 1967-03-17 US US623834A patent/US3553199A/en not_active Expired - Lifetime
-
1968
- 1968-02-29 CH CH305168A patent/CH493539A/de not_active IP Right Cessation
- 1968-03-02 DE DE19681695226 patent/DE1695226A1/de active Pending
- 1968-03-06 SE SE02979/68A patent/SE335736B/xx unknown
- 1968-03-14 IL IL29640A patent/IL29640A/en unknown
- 1968-03-14 YU YU583/68A patent/YU34201B/xx unknown
- 1968-03-15 DK DK113168AA patent/DK121125B/da unknown
- 1968-03-15 NO NO1012/68A patent/NO123037B/no unknown
- 1968-03-15 NL NL6803724A patent/NL6803724A/xx unknown
- 1968-03-15 FR FR1556196D patent/FR1556196A/fr not_active Expired
- 1968-03-15 BE BE712207D patent/BE712207A/xx unknown
- 1968-03-15 AT AT256968A patent/AT278820B/de not_active IP Right Cessation
- 1968-03-15 FI FI680717A patent/FI48088C/fi active
- 1968-03-16 ES ES351720A patent/ES351720A1/es not_active Expired
- 1968-03-18 GB GB12651/68A patent/GB1148288A/en not_active Expired
-
1969
- 1969-12-31 MY MY1969399A patent/MY6900399A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT278820B (de) | 1970-02-10 |
| US3553199A (en) | 1971-01-05 |
| IL29640A (en) | 1972-06-28 |
| FR1556196A (US20100268047A1-20101021-C00003.png) | 1969-01-31 |
| YU58368A (en) | 1978-06-30 |
| SE335736B (US20100268047A1-20101021-C00003.png) | 1971-06-07 |
| NL6803724A (US20100268047A1-20101021-C00003.png) | 1968-09-18 |
| FI48088B (US20100268047A1-20101021-C00003.png) | 1974-02-28 |
| MY6900399A (en) | 1969-12-31 |
| DK121125B (da) | 1971-09-13 |
| ES351720A1 (es) | 1969-06-16 |
| GB1148288A (en) | 1969-04-10 |
| DE1695226A1 (de) | 1971-03-18 |
| FI48088C (fi) | 1974-06-10 |
| BE712207A (US20100268047A1-20101021-C00003.png) | 1968-09-16 |
| CH493539A (de) | 1970-07-15 |
| YU34201B (en) | 1979-02-28 |
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