FI94625B - Förfarande för framställning av derivat av trans-1,1,2-trifenyl-but-1-en - Google Patents
Förfarande för framställning av derivat av trans-1,1,2-trifenyl-but-1-en Download PDFInfo
- Publication number
- FI94625B FI94625B FI884461A FI884461A FI94625B FI 94625 B FI94625 B FI 94625B FI 884461 A FI884461 A FI 884461A FI 884461 A FI884461 A FI 884461A FI 94625 B FI94625 B FI 94625B
- Authority
- FI
- Finland
- Prior art keywords
- trans
- preparation
- parts
- triphenylbut
- hydrochloric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000002360 preparation method Methods 0.000 title claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 238000007796 conventional method Methods 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 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 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 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
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- JQKMNNYZQUQIJJ-UHFFFAOYSA-N 1,1-diphenylbut-1-en-2-ylbenzene Chemical class C=1C=CC=CC=1C(CC)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JQKMNNYZQUQIJJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method 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
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(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)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- -1 2- (N, N-dimethylamino) ethoxy Chemical group 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 compound 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 compound 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
- MPMAKJDYHJDJDO-UHFFFAOYSA-N 3-[1-[4-[2-(diethylamino)ethoxy]phenyl]-1-hydroxy-2-phenylbutyl]phenol Chemical compound C=1C=C(OCCN(CC)CC)C=CC=1C(O)(C=1C=C(O)C=CC=1)C(CC)C1=CC=CC=C1 MPMAKJDYHJDJDO-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 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
- 239000002244 precipitate Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 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
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)
Claims (4)
1. Förfarande för framställning av trans-1,1,2-trifenyl-but-l-en-derivat enligt den allmänna formeIn (1): R1 • o-ch2ch2h' , ό n crj^ R2 där R1 är CH3 eller CH2CH3 och R2 är H eller OH, k ä n n e -tecknat av, att man upphettar karbinoler enligt den allmänna formeln (2): 1 , * B 94625 y JWh2\i O <2> R2 där R1 och R2 betecknar detsamma som ovan, under minst 10 tim-mar vid en temperatur av 50 - 60 °C i ett medium som inte inne-häller organiskt lösningsmedel men innehäller ätminstone 25 vikt-% saltsyra eller ätminstone 40 volym-% svavelsyra , och behandlar den erhällna produkten enligt sedvanliga metoder.
2. Förfarande enligt patentkravet 1, kännetecknat av, att man upphettar under 12-16 timmar vid 50 - 60 °C.
3. Förfarande enligt patentkravet 1 eller 2, kännetecknat av, att saltsyrakoncentrationen är mellan 32 -37 vikt-%.
4. Förfarande enligt patentkravet 1 eller 2, känne- :. t e c k n a t av, att svavelsyrakoncentrationen är mellan 45 -50 volym-%. It
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19873736682 DE3736682A1 (de) | 1987-10-29 | 1987-10-29 | Verfahren zur herstellung von trans-1,1,2-triphenyl-but-1-en-derivaten |
| DE3736682 | 1987-10-29 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI884461A0 FI884461A0 (sv) | 1988-09-28 |
| FI884461A FI884461A (sv) | 1989-04-30 |
| FI94625B true FI94625B (sv) | 1995-06-30 |
| FI94625C FI94625C (sv) | 1995-10-10 |
Family
ID=6339363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI884461A FI94625C (sv) | 1987-10-29 | 1988-09-28 | Förfarande för framställning av derivat av trans-1,1,2-trifenyl-but-1-en |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4960937A (sv) |
| EP (1) | EP0313799B1 (sv) |
| AT (1) | ATE85605T1 (sv) |
| DE (2) | DE3736682A1 (sv) |
| DK (1) | DK170300B1 (sv) |
| ES (1) | ES2038263T3 (sv) |
| FI (1) | FI94625C (sv) |
| GR (1) | GR3007027T3 (sv) |
| HU (1) | HU202824B (sv) |
| NO (1) | NO169120C (sv) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0169186B1 (ko) * | 1993-10-25 | 1999-03-20 | 고바야시 유끼오 | 트리페닐에틸렌 화합물의 z이성체 산부가염의 제조방법 |
| DE69409835T2 (de) * | 1994-01-03 | 1998-10-01 | Klinge Co Chem Pharm Fab | Verfahren zur herstellung von e-1-[4'-(2-dimethylaminoethoxy)-phenyl]-1-(3'hydroxyphenyl)-2-phenyl-1-buten |
| US5681835A (en) * | 1994-04-25 | 1997-10-28 | Glaxo Wellcome Inc. | Non-steroidal ligands for the estrogen receptor |
| HUP9900951A3 (en) | 1996-01-20 | 2000-02-28 | Bradford University Bradford | Process for producing tamoxifen and analogues thereof |
| GB9715479D0 (en) * | 1997-07-23 | 1997-10-01 | Univ Bradford | Tamoxifen and analogues thereof |
| HUP0002852A3 (en) | 1997-08-15 | 2001-11-28 | Univ Durham | A method of preventing or treating estrogen-dependent diseases and disorders using triphenil-ethylene derivatives |
| CN114133334A (zh) * | 2021-11-09 | 2022-03-04 | 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 (sv) * | 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 |
| EP0127128B1 (en) * | 1983-05-24 | 1987-02-25 | Bristol-Myers Company | Process for the conversion of the e isomer of 1,2-diphenyl-1-(4-(2-dimethylaminoethoxy)-phenyl)-1-butene to tamoxifen hcl |
| 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 EP EP88115306A patent/EP0313799B1/de not_active Expired - Lifetime
- 1988-09-19 ES ES198888115306T patent/ES2038263T3/es not_active Expired - Lifetime
- 1988-09-19 AT AT88115306T patent/ATE85605T1/de not_active IP Right Cessation
- 1988-09-19 DE DE8888115306T patent/DE3878394D1/de not_active Expired - Fee Related
- 1988-09-28 FI FI884461A patent/FI94625C/sv 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 |
|---|---|
| DK604288D0 (da) | 1988-10-28 |
| HUT51592A (en) | 1990-05-28 |
| DE3878394D1 (de) | 1993-03-25 |
| EP0313799A3 (en) | 1990-05-30 |
| ATE85605T1 (de) | 1993-02-15 |
| NO884800D0 (no) | 1988-10-27 |
| EP0313799A2 (de) | 1989-05-03 |
| ES2038263T3 (es) | 1993-07-16 |
| FI94625C (sv) | 1995-10-10 |
| FI884461A0 (sv) | 1988-09-28 |
| DK170300B1 (da) | 1995-07-31 |
| NO169120C (no) | 1992-05-13 |
| HU202824B (en) | 1991-04-29 |
| NO169120B (no) | 1992-02-03 |
| DK604288A (da) | 1989-04-30 |
| FI884461A (sv) | 1989-04-30 |
| US4960937A (en) | 1990-10-02 |
| GR3007027T3 (sv) | 1993-07-30 |
| EP0313799B1 (de) | 1993-02-10 |
| DE3736682A1 (de) | 1989-05-11 |
| NO884800L (no) | 1989-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed |
Owner name: KLINGE PHARMA GMBH |