NO301003B1 - Fremgangsmåte for fremstilling av E-1-£4'-(2-dimetyl-aminoetoksy)-fenyl|-1-(3'-hydroksyfenyl)-2-fenyl-1-buten - Google Patents
Fremgangsmåte for fremstilling av E-1-£4'-(2-dimetyl-aminoetoksy)-fenyl|-1-(3'-hydroksyfenyl)-2-fenyl-1-buten Download PDFInfo
- Publication number
- NO301003B1 NO301003B1 NO945077A NO945077A NO301003B1 NO 301003 B1 NO301003 B1 NO 301003B1 NO 945077 A NO945077 A NO 945077A NO 945077 A NO945077 A NO 945077A NO 301003 B1 NO301003 B1 NO 301003B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- reaction mixture
- formula
- hours
- hydroxyphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000002360 preparation method Methods 0.000 title description 3
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 claims description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000011541 reaction mixture Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- ZQZFYGIXNQKOAV-QPLCGJKRSA-N 3-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]phenol Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)/C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-QPLCGJKRSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- PDUNTJGTEXGYSN-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-[3-(oxan-2-yloxy)phenyl]-2-phenylbutan-1-ol Chemical compound C=1C=C(OCCN(C)C)C=CC=1C(O)(C=1C=C(OC2OCCCC2)C=CC=1)C(CC)C1=CC=CC=C1 PDUNTJGTEXGYSN-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008187 granular material 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
- 238000002156 mixing Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- 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
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP1994/000001 WO1995018786A1 (en) | 1994-01-03 | 1994-01-03 | Method for the production of e-1-[4'-(2-dimethylaminoethoxy)-phenyl]-1-(3'-hydroxyphenyl)-2-phenyl-1-butene |
| CN94194961A CN1142815A (zh) | 1994-01-03 | 1994-01-03 | E-1-[4'-(2-二甲氨基乙氧基)-苯基]-1-(3'羟苯基)-2-苯基-1-丁烯的制备方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO945077D0 NO945077D0 (no) | 1994-12-29 |
| NO945077L NO945077L (no) | 1995-07-04 |
| NO301003B1 true NO301003B1 (no) | 1997-09-01 |
Family
ID=37708199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO945077A NO301003B1 (no) | 1994-01-03 | 1994-12-29 | Fremgangsmåte for fremstilling av E-1-£4'-(2-dimetyl-aminoetoksy)-fenyl|-1-(3'-hydroksyfenyl)-2-fenyl-1-buten |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5693863A (zh) |
| EP (1) | EP0738256B1 (zh) |
| JP (1) | JPH09507240A (zh) |
| CN (1) | CN1142815A (zh) |
| AU (1) | AU691113B2 (zh) |
| CZ (1) | CZ330994A3 (zh) |
| DE (1) | DE69409835T2 (zh) |
| EE (1) | EE03191B1 (zh) |
| ES (1) | ES2115207T3 (zh) |
| FI (1) | FI950011A (zh) |
| IL (1) | IL112166A0 (zh) |
| NO (1) | NO301003B1 (zh) |
| PL (1) | PL177916B1 (zh) |
| RU (1) | RU2124499C1 (zh) |
| WO (1) | WO1995018786A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2243330A1 (en) * | 1996-01-20 | 1997-07-24 | Ioana Popa | Tamoxifen and analogues thereof |
| GB9601167D0 (en) * | 1996-01-20 | 1996-03-20 | Univ Bradford | Tamoxifen and analogues thereof |
| GB9715479D0 (en) * | 1997-07-23 | 1997-10-01 | Univ Bradford | Tamoxifen and analogues thereof |
| JP4572407B2 (ja) * | 2005-03-04 | 2010-11-04 | 学校法人東京理科大学 | ドロロキシフェンの製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3046719C2 (de) * | 1980-12-11 | 1983-02-17 | Klinge Pharma GmbH, 8000 München | 1,1,2-Triphenyl-but-1-en-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel |
| EP0260066B1 (en) * | 1986-09-11 | 1990-05-09 | National Research Development Corporation | Tamoxifen derivatives |
| DE3736682A1 (de) * | 1987-10-29 | 1989-05-11 | Klinge Co Chem Pharm Fab | Verfahren zur herstellung von trans-1,1,2-triphenyl-but-1-en-derivaten |
-
1994
- 1994-01-03 JP JP7518286A patent/JPH09507240A/ja active Pending
- 1994-01-03 ES ES94903888T patent/ES2115207T3/es not_active Expired - Lifetime
- 1994-01-03 RU RU96116153A patent/RU2124499C1/ru active
- 1994-01-03 AU AU58158/94A patent/AU691113B2/en not_active Ceased
- 1994-01-03 US US08/669,350 patent/US5693863A/en not_active Expired - Fee Related
- 1994-01-03 EP EP94903888A patent/EP0738256B1/en not_active Expired - Lifetime
- 1994-01-03 CN CN94194961A patent/CN1142815A/zh active Pending
- 1994-01-03 DE DE69409835T patent/DE69409835T2/de not_active Expired - Fee Related
- 1994-01-03 WO PCT/EP1994/000001 patent/WO1995018786A1/en active IP Right Grant
- 1994-11-16 EE EE9400200A patent/EE03191B1/xx unknown
- 1994-12-27 CZ CZ943309A patent/CZ330994A3/cs unknown
- 1994-12-27 IL IL11216694A patent/IL112166A0/xx unknown
- 1994-12-29 NO NO945077A patent/NO301003B1/no not_active IP Right Cessation
-
1995
- 1995-01-02 PL PL95306666A patent/PL177916B1/pl unknown
- 1995-01-02 FI FI950011A patent/FI950011A/fi unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CZ330994A3 (en) | 1995-07-12 |
| FI950011A0 (fi) | 1995-01-02 |
| EP0738256A1 (en) | 1996-10-23 |
| PL177916B1 (pl) | 2000-01-31 |
| WO1995018786A1 (en) | 1995-07-13 |
| EE03191B1 (et) | 1999-06-15 |
| RU2124499C1 (ru) | 1999-01-10 |
| PL306666A1 (en) | 1995-07-10 |
| AU5815894A (en) | 1995-08-01 |
| US5693863A (en) | 1997-12-02 |
| JPH09507240A (ja) | 1997-07-22 |
| NO945077D0 (no) | 1994-12-29 |
| NO945077L (no) | 1995-07-04 |
| DE69409835D1 (de) | 1998-05-28 |
| ES2115207T3 (es) | 1998-06-16 |
| CN1142815A (zh) | 1997-02-12 |
| EP0738256B1 (en) | 1998-04-22 |
| IL112166A0 (en) | 1995-03-15 |
| FI950011A (fi) | 1995-07-04 |
| AU691113B2 (en) | 1998-05-07 |
| DE69409835T2 (de) | 1998-10-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |
Free format text: LAPSED IN JUNE 2001 |