DK170300B1 - Fremgangsmåde til fremstilling af trans-1,1,2-tri phenyl-but-1-en-derivater - Google Patents
Fremgangsmåde til fremstilling af trans-1,1,2-tri phenyl-but-1-en-derivater Download PDFInfo
- Publication number
- DK170300B1 DK170300B1 DK604288A DK604288A DK170300B1 DK 170300 B1 DK170300 B1 DK 170300B1 DK 604288 A DK604288 A DK 604288A DK 604288 A DK604288 A DK 604288A DK 170300 B1 DK170300 B1 DK 170300B1
- Authority
- DK
- Denmark
- Prior art keywords
- trans
- phenyl
- parts
- preparation
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims 1
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 description 3
- 239000000203 mixture Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- HFHRSBKYURPWRU-UHFFFAOYSA-N 1,1-diphenylbut-3-enylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(CC=C)C1=CC=CC=C1 HFHRSBKYURPWRU-UHFFFAOYSA-N 0.000 description 1
- VFFBJZCCXOYRNN-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]-1,2-diphenylbutan-1-ol Chemical compound C=1C=CC=CC=1C(O)(C=1C=CC(OCCN(C)C)=CC=1)C(CC)C1=CC=CC=C1 VFFBJZCCXOYRNN-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- -1 2-di methylaminoethoxy Chemical group 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3736682 | 1987-10-29 | ||
| DE19873736682 DE3736682A1 (de) | 1987-10-29 | 1987-10-29 | Verfahren zur herstellung von trans-1,1,2-triphenyl-but-1-en-derivaten |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK604288D0 DK604288D0 (da) | 1988-10-28 |
| DK604288A DK604288A (da) | 1989-04-30 |
| DK170300B1 true DK170300B1 (da) | 1995-07-31 |
Family
ID=6339363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK604288A DK170300B1 (da) | 1987-10-29 | 1988-10-28 | Fremgangsmåde til fremstilling af trans-1,1,2-tri phenyl-but-1-en-derivater |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4960937A (no) |
| EP (1) | EP0313799B1 (no) |
| AT (1) | ATE85605T1 (no) |
| DE (2) | DE3736682A1 (no) |
| DK (1) | DK170300B1 (no) |
| ES (1) | ES2038263T3 (no) |
| FI (1) | FI94625C (no) |
| GR (1) | GR3007027T3 (no) |
| HU (1) | HU202824B (no) |
| NO (1) | NO169120C (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69409502T2 (de) * | 1993-10-25 | 1998-11-12 | Taiho Pharmaceutical Co Ltd | Verfahren zur herstellung von säure-additions-salzen des z-isomers von triphenylethylen-derivaten |
| JPH09507240A (ja) * | 1994-01-03 | 1997-07-22 | クリンゲ・ファルマ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Ｅ−１−［４’−（２−ジメチルアミノエトキシ）−フェニル］−１−（３’−ヒドロキシフェニル）−２−フェニル−１−ブテンの製造方法 |
| US5681835A (en) * | 1994-04-25 | 1997-10-28 | Glaxo Wellcome Inc. | Non-steroidal ligands for the estrogen receptor |
| CA2243330A1 (en) | 1996-01-20 | 1997-07-24 | Ioana Popa | Tamoxifen and analogues thereof |
| GB9715479D0 (en) * | 1997-07-23 | 1997-10-01 | Univ Bradford | Tamoxifen and analogues thereof |
| CA2301032C (en) | 1997-08-15 | 2009-01-13 | Duke University | A method of preventing or treating estrogen-dependent diseases and disorders |
| CN114133334B (zh) * | 2021-11-09 | 2024-07-19 | 北京京丰制药(山东)有限公司 | 枸橼酸他莫昔芬的工业化制备工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637389A (no) * | 1962-09-13 | |||
| GB1013907A (en) * | 1962-09-13 | 1965-12-22 | Ici Ltd | Alkene derivatives |
| 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 |
| ATE25515T1 (de) * | 1983-05-24 | 1987-03-15 | Bristol Myers Co | Verfahren zur umwandlung von 1,2-diphenyl-1-(4-(2-dimethylamino-ethoxy)-phen l>-1-buten-e-isomeren zu tamoxifen-hydrochlorid. |
| EP0168175B1 (en) * | 1984-06-12 | 1987-11-19 | National Research Development Corporation | Preparation of tamoxifen |
| CN1013859B (zh) * | 1986-11-21 | 1991-09-11 | 中国人民解放军防化研究院第四所 | 枸橼酸三苯氧胺合成方法的改进 |
-
1987
- 1987-10-29 DE DE19873736682 patent/DE3736682A1/de not_active Withdrawn
-
1988
- 1988-09-19 ES ES198888115306T patent/ES2038263T3/es not_active Expired - Lifetime
- 1988-09-19 DE DE8888115306T patent/DE3878394D1/de not_active Expired - Fee Related
- 1988-09-19 EP EP88115306A patent/EP0313799B1/de not_active Expired - Lifetime
- 1988-09-19 AT AT88115306T patent/ATE85605T1/de not_active IP Right Cessation
- 1988-09-28 FI FI884461A patent/FI94625C/fi not_active IP Right Cessation
- 1988-10-27 NO NO884800A patent/NO169120C/no not_active IP Right Cessation
- 1988-10-27 US US07/263,209 patent/US4960937A/en not_active Expired - Fee Related
- 1988-10-28 HU HU885630A patent/HU202824B/hu not_active IP Right Cessation
- 1988-10-28 DK DK604288A patent/DK170300B1/da not_active IP Right Cessation
-
1993
- 1993-02-11 GR GR920402546T patent/GR3007027T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0313799A3 (en) | 1990-05-30 |
| NO884800D0 (no) | 1988-10-27 |
| FI884461A0 (fi) | 1988-09-28 |
| ES2038263T3 (es) | 1993-07-16 |
| NO169120C (no) | 1992-05-13 |
| GR3007027T3 (no) | 1993-07-30 |
| NO169120B (no) | 1992-02-03 |
| FI94625B (fi) | 1995-06-30 |
| DE3736682A1 (de) | 1989-05-11 |
| NO884800L (no) | 1989-05-02 |
| EP0313799B1 (de) | 1993-02-10 |
| FI884461A (fi) | 1989-04-30 |
| HU202824B (en) | 1991-04-29 |
| ATE85605T1 (de) | 1993-02-15 |
| DK604288D0 (da) | 1988-10-28 |
| US4960937A (en) | 1990-10-02 |
| EP0313799A2 (de) | 1989-05-03 |
| FI94625C (fi) | 1995-10-10 |
| DK604288A (da) | 1989-04-30 |
| HUT51592A (en) | 1990-05-28 |
| DE3878394D1 (de) | 1993-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |