CA1087212A - Triphenylalkene derivatives and process for preparing same - Google Patents
Triphenylalkene derivatives and process for preparing sameInfo
- Publication number
- CA1087212A CA1087212A CA271,086A CA271086A CA1087212A CA 1087212 A CA1087212 A CA 1087212A CA 271086 A CA271086 A CA 271086A CA 1087212 A CA1087212 A CA 1087212A
- Authority
- CA
- Canada
- Prior art keywords
- diphenyl
- butene
- acid
- general formula
- butanol
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- KDKKRJMQCQNZDY-UHFFFAOYSA-N 1-(1,2-diphenylbut-1-enyl)-4-fluorobenzene Chemical compound C=1C=CC=CC=1C(CC)=C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 KDKKRJMQCQNZDY-UHFFFAOYSA-N 0.000 claims description 3
- XWIKPNQTSLCDMC-UHFFFAOYSA-N 1-(4-bromophenyl)-1,2-diphenylbutan-1-ol Chemical compound C1(=CC=CC=C1)C(C(CC)C1=CC=CC=C1)(O)C1=CC=C(C=C1)Br XWIKPNQTSLCDMC-UHFFFAOYSA-N 0.000 claims description 3
- LSZQQLHQPDOPJW-UHFFFAOYSA-N 1-(4-chlorophenyl)-1,2-diphenylbutan-1-ol Chemical compound C1(=CC=CC=C1)C(C(CC)C1=CC=CC=C1)(O)C1=CC=C(C=C1)Cl LSZQQLHQPDOPJW-UHFFFAOYSA-N 0.000 claims description 3
- PKWCGWGPYGPHOQ-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,2-diphenylbutan-1-ol Chemical compound C1(=CC=CC=C1)C(C(CC)C1=CC=CC=C1)(O)C1=CC=C(C=C1)F PKWCGWGPYGPHOQ-UHFFFAOYSA-N 0.000 claims description 3
- NUNRCACEJFCJLA-UHFFFAOYSA-N 1-bromo-4-(1,2-diphenylbut-1-enyl)benzene Chemical compound C=1C=CC=CC=1C(CC)=C(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 NUNRCACEJFCJLA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- VUXXHBSIYVYJDA-UHFFFAOYSA-N 1-chloro-4-(1,2-diphenylbut-1-enyl)benzene Chemical compound C=1C=CC=CC=1C(CC)=C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 VUXXHBSIYVYJDA-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000003791 organic solvent mixture Substances 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000004071 biological effect Effects 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 229960001603 tamoxifen Drugs 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 7
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- NOBLQBKAPAMUAQ-UHFFFAOYSA-N 1-(2-ethylphenyl)-2-phenylethanone Chemical compound CCC1=CC=CC=C1C(=O)CC1=CC=CC=C1 NOBLQBKAPAMUAQ-UHFFFAOYSA-N 0.000 description 1
- MOSIKPSTRPODHQ-UHFFFAOYSA-N 1-(4-bromophenyl)-2-phenylethan-1-one Chemical compound C1=CC(Br)=CC=C1C(=O)CC1=CC=CC=C1 MOSIKPSTRPODHQ-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- KVNQDINBFMRKLP-UHFFFAOYSA-N 1-chloro-4-(1,2-diphenylprop-1-enyl)benzene Chemical compound C1(=CC=CC=C1)C(=C(C)C1=CC=CC=C1)C1=CC=C(C=C1)Cl KVNQDINBFMRKLP-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
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001344 alkene derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical class [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/24—Halogenated aromatic hydrocarbons with unsaturated side chains
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU76GO00001328A HU171269B (hu) | 1976-02-05 | 1976-02-05 | Sposob poluchenija novykh proizvodnykh trifenil-alkenov |
| HUGO-1328 | 1976-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087212A true CA1087212A (en) | 1980-10-07 |
Family
ID=10996802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA271,086A Expired CA1087212A (en) | 1976-02-05 | 1977-02-04 | Triphenylalkene derivatives and process for preparing same |
Country Status (11)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870219A (en) * | 1986-05-23 | 1989-09-26 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US4990703A (en) * | 1987-03-17 | 1991-02-05 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US5030764A (en) * | 1986-05-23 | 1991-07-09 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US5030765A (en) * | 1986-05-23 | 1991-07-09 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011372B1 (en) * | 1978-11-07 | 1983-02-09 | Imperial Chemical Industries Plc | 1-acyloxyphenyl-1,2-diphenylalkene derivatives, processes for their manufacture and a pharmaceutical composition containing these derivatives |
| GB9714310D0 (en) * | 1997-07-07 | 1997-09-10 | Smithkline Beecham Plc | Process |
-
1976
- 1976-02-05 HU HU76GO00001328A patent/HU171269B/hu unknown
-
1977
- 1977-01-28 SU SU772446005A patent/SU856376A3/ru active
- 1977-02-01 NL NL7701025A patent/NL7701025A/xx not_active Application Discontinuation
- 1977-02-01 AT AT59577A patent/AT345804B/de not_active IP Right Cessation
- 1977-02-03 SE SE7701213A patent/SE431324B/xx not_active IP Right Cessation
- 1977-02-04 CH CH136077A patent/CH624655A5/de not_active IP Right Cessation
- 1977-02-04 JP JP1084777A patent/JPS52122352A/ja active Granted
- 1977-02-04 CA CA271,086A patent/CA1087212A/en not_active Expired
- 1977-02-04 YU YU309/77A patent/YU39669B/xx unknown
- 1977-02-04 PL PL1977195823A patent/PL105534B1/pl unknown
- 1977-02-04 DE DE2704690A patent/DE2704690C2/de not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4870219A (en) * | 1986-05-23 | 1989-09-26 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US4935560A (en) * | 1986-05-23 | 1990-06-19 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene & indane derivatives |
| US5001276A (en) * | 1986-05-23 | 1991-03-19 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US5030764A (en) * | 1986-05-23 | 1991-07-09 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US5030765A (en) * | 1986-05-23 | 1991-07-09 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US5055622A (en) * | 1986-05-23 | 1991-10-08 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
| US4990703A (en) * | 1987-03-17 | 1991-02-05 | Hoffmann-La Roche Inc. | Novel tetrahydronaphthalene and indane derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| YU39669B (en) | 1985-03-20 |
| DE2704690A1 (de) | 1977-08-11 |
| SE7701213L (sv) | 1977-08-06 |
| DE2704690C2 (de) | 1987-01-29 |
| JPS6149294B2 (enrdf_load_stackoverflow) | 1986-10-29 |
| NL7701025A (nl) | 1977-08-09 |
| CH624655A5 (en) | 1981-08-14 |
| PL105534B1 (pl) | 1979-10-31 |
| SU856376A3 (ru) | 1981-08-15 |
| HU171269B (hu) | 1977-12-28 |
| YU30977A (en) | 1982-06-30 |
| AT345804B (de) | 1978-10-10 |
| ATA59577A (de) | 1978-02-15 |
| JPS52122352A (en) | 1977-10-14 |
| SE431324B (sv) | 1984-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |