CA1208233A - Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires - Google Patents

Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires

Info

Publication number: CA1208233A
Authority: CA; Canada
Prior art keywords: formula; phenyl; compound; reaction; mol
Prior art date: 1981-12-23
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

Application number

CA000484636A

Other languages

English (en)

Inventor

Thomas B.K. Lee

George E. Lee

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Aventis Pharmaceuticals Inc

Original Assignee

Hoechst Roussel Pharmaceuticals Inc

Priority date (The priority date 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 date listed.)

1981-12-23

Filing date

1985-06-20

Publication date

1986-07-22

1981-12-23 Priority claimed from US06/333,965 external-priority patent/US4374067A/en

1985-06-20 Application filed by Hoechst Roussel Pharmaceuticals Inc filed Critical Hoechst Roussel Pharmaceuticals Inc

1985-06-20 Priority to CA000484636A priority Critical patent/CA1208233A/fr

1986-07-22 Application granted granted Critical

1986-07-22 Publication of CA1208233A publication Critical patent/CA1208233A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title claims abstract description 10
239000000543 intermediate Substances 0.000 title description 15
150000001875 compounds Chemical class 0.000 claims abstract description 44
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims description 17
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 16
-1 methyl sulfonyloxy Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 3
229910000510 noble metal Inorganic materials 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 2
229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
239000001961 anticonvulsive agent Substances 0.000 abstract description 2
239000000935 antidepressant agent Substances 0.000 abstract description 2
229940005513 antidepressants Drugs 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
230000001773 anti-convulsant effect Effects 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
239000000047 product Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
150000003839 salts Chemical class 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
239000012458 free base Substances 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
239000000203 mixture Substances 0.000 description 7
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 6
QWSUPGPRZVRNMD-UHFFFAOYSA-N 2,3-dimethyl-4-phenyl-1,3-benzodiazepine Chemical compound CN1C(C)=NC2=CC=CC=C2C=C1C1=CC=CC=C1 QWSUPGPRZVRNMD-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
125000005228 aryl sulfonate group Chemical group 0.000 description 6
150000004820 halides Chemical class 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
150000002440 hydroxy compounds Chemical class 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
150000002430 hydrocarbons Chemical group 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000004215 Carbon black (E152) Substances 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000004391 aryl sulfonyl group Chemical group 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000010791 quenching Methods 0.000 description 3
230000000171 quenching effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
229910006124 SOCl2 Inorganic materials 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
230000002051 biphasic effect Effects 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
239000012043 crude product Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000008241 heterogeneous mixture Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
LSNHMECUSOIDOP-UHFFFAOYSA-N n-[2-(2-hydroxy-2-phenylethyl)phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC=C1CC(O)C1=CC=CC=C1 LSNHMECUSOIDOP-UHFFFAOYSA-N 0.000 description 2
CPQCSJYYDADLCZ-UHFFFAOYSA-N n-methylhydroxylamine Chemical compound CNO CPQCSJYYDADLCZ-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
229940117803 phenethylamine Drugs 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
CSGRQLUGMVFNON-UHFFFAOYSA-N 2,2-dimethyl-n-(2-methylphenyl)propanamide Chemical compound CC1=CC=CC=C1NC(=O)C(C)(C)C CSGRQLUGMVFNON-UHFFFAOYSA-N 0.000 description 1
STDYWHYUOSSCBO-UHFFFAOYSA-N 2,3-dimethyl-4-phenyl-4,5-dihydro-1,3-benzodiazepine Chemical compound C1C2=CC=CC=C2N=C(C)N(C)C1C1=CC=CC=C1 STDYWHYUOSSCBO-UHFFFAOYSA-N 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
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
XCQPQZZKXKILQA-UHFFFAOYSA-N 4-phenyl-3h-1,3-benzodiazepine Chemical compound C=1C2=CC=CC=C2NC=NC=1C1=CC=CC=C1 XCQPQZZKXKILQA-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
102100038916 Caspase-5 Human genes 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
101100273286 Mus musculus Casp4 gene Proteins 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012039 electrophile Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000006138 lithiation reaction Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
HETCBLDRLDHPTO-UHFFFAOYSA-N n-[2-(2-chloro-2-phenylethyl)phenyl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CC=CC=C1CC(Cl)C1=CC=CC=C1 HETCBLDRLDHPTO-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
QLNJFJADRCOGBJ-LBPDFUHNSA-N propanamide Chemical group CC[13C](N)=O QLNJFJADRCOGBJ-LBPDFUHNSA-N 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
UMDAFUNCFQYMDP-UHFFFAOYSA-N tert-butyl n-(2-methylphenyl)carbamate Chemical compound CC1=CC=CC=C1NC(=O)OC(C)(C)C UMDAFUNCFQYMDP-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000484636A 1981-12-23 1985-06-20 Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires Expired CA1208233A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000484636A CA1208233A (fr)	1981-12-23	1985-06-20	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/333,965 US4374067A (en)	1981-12-23	1981-12-23	Intermediates for the preparation of 4-phenyl-1,3-benzodiazepins and methods for preparing the intermediates
US333,965		1981-12-23
CA000418332A CA1213900A (fr)	1981-12-23	1982-12-22	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et preparation des produits intermediaires
CA000484636A CA1208233A (fr)	1981-12-23	1985-06-20	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000484636A Division CA1208233A (fr)	1981-12-23	1985-06-20	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000484636A Division CA1208233A (fr)	1981-12-23	1985-06-20	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires

Publications (1)

Publication Number	Publication Date
CA1208233A true CA1208233A (fr)	1986-07-22

Family

ID=25669897

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA000484636A Expired CA1208233A (fr)	1981-12-23	1985-06-20	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methodes pour preparer les produits intermediaires
CA000484635A Expired CA1207796A (fr)	1981-12-23	1985-06-20	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methode pour preparer les produits intermediaires

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA000484635A Expired CA1207796A (fr)	1981-12-23	1985-06-20	Produits intermediaires pour la preparation de 4-phenyl-1,3-benzodiazepines et methode pour preparer les produits intermediaires

Country Status (1)

Country	Link
CA (2)	CA1208233A (fr)

1985
- 1985-06-20 CA CA000484636A patent/CA1208233A/fr not_active Expired
- 1985-06-20 CA CA000484635A patent/CA1207796A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1207796A (fr)	1986-07-15

Legal Events

Date	Code	Title	Description
2003-07-22	MKEX	Expiry

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