NO314229B1 - Benzotiofenforbindelser, mellomprodukter, sammensetninger, fremgangsmåter og anvendelse av samme - Google Patents
Benzotiofenforbindelser, mellomprodukter, sammensetninger, fremgangsmåter og anvendelse av samme Download PDFInfo
- Publication number
- NO314229B1 NO314229B1 NO19960796A NO960796A NO314229B1 NO 314229 B1 NO314229 B1 NO 314229B1 NO 19960796 A NO19960796 A NO 19960796A NO 960796 A NO960796 A NO 960796A NO 314229 B1 NO314229 B1 NO 314229B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- benzo
- thiophene
- compound
- phenoxy
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 85
- 230000008569 process Effects 0.000 title claims description 15
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title description 460
- 239000000203 mixture Substances 0.000 title description 78
- 239000000543 intermediate Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 236
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 181
- 125000006239 protecting group Chemical group 0.000 claims description 79
- 238000006243 chemical reaction Methods 0.000 claims description 74
- -1 methyl-1-pyrrolidinyl Chemical group 0.000 claims description 62
- 239000000262 estrogen Substances 0.000 claims description 48
- 229940011871 estrogen Drugs 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 34
- 238000004519 manufacturing process Methods 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 206010028980 Neoplasm Diseases 0.000 claims description 21
- 201000010260 leiomyoma Diseases 0.000 claims description 15
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 14
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 239000000583 progesterone congener Substances 0.000 claims description 14
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
- 206010027304 Menopausal symptoms Diseases 0.000 claims description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 9
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- 201000007954 uterine fibroid Diseases 0.000 claims description 9
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- 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 claims description 7
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- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 5
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- 125000004434 sulfur atom Chemical group 0.000 claims description 4
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- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
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- 238000004458 analytical method Methods 0.000 description 84
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- 238000011282 treatment Methods 0.000 description 45
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- 241001465754 Metazoa Species 0.000 description 34
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- 125000005605 benzo group Chemical group 0.000 description 32
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- 125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 27
- 238000012360 testing method Methods 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- 229910052938 sodium sulfate Inorganic materials 0.000 description 25
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- 239000000047 product Substances 0.000 description 23
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/396,401 US5510357A (en) | 1995-02-28 | 1995-02-28 | Benzothiophene compounds as anti-estrogenic agents |
| US55276095A | 1995-11-03 | 1995-11-03 | |
| US08/552,564 US5998441A (en) | 1995-02-28 | 1995-11-03 | Benzothiophene compounds, intermediates, compositions, and methods |
| US08/552,636 US5723474A (en) | 1995-02-28 | 1995-11-03 | Benzothiophene compounds, intermediates, compositions, and methods |
| US08/552,565 US5977093A (en) | 1995-02-28 | 1995-11-03 | Benzothiophene compounds, intermediates, compositions, and methods |
| US08/552,679 US5856339A (en) | 1995-02-28 | 1995-11-03 | Benzothiophene compounds, intermediates, compositions, and methods |
| US08/554,223 US5856340A (en) | 1995-02-28 | 1995-11-03 | Method of treating estrogen dependent cancers |
| US08/552,890 US5919800A (en) | 1995-02-28 | 1995-11-03 | Benzothiophene compounds, intermediates, compositions, and methods |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO960796D0 NO960796D0 (no) | 1996-02-27 |
| NO960796L NO960796L (no) | 1996-08-29 |
| NO314229B1 true NO314229B1 (no) | 2003-02-17 |
Family
ID=27575428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19960796A NO314229B1 (no) | 1995-02-28 | 1996-02-27 | Benzotiofenforbindelser, mellomprodukter, sammensetninger, fremgangsmåter og anvendelse av samme |
Country Status (8)
| Country | Link |
|---|---|
| CN (1) | CN1086700C (hu) |
| BR (1) | BR9600829A (hu) |
| CA (1) | CA2170479C (hu) |
| CZ (1) | CZ290200B6 (hu) |
| FI (1) | FI120345B (hu) |
| HU (1) | HU226326B1 (hu) |
| NO (1) | NO314229B1 (hu) |
| TR (1) | TR199600127A2 (hu) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE535691C2 (sv) * | 2011-03-08 | 2012-11-13 | Kat2Biz Ab | Reduktion av C-O-bindningar via katalytisk transfer hydrogenolys |
| CN102746290B (zh) * | 2012-06-21 | 2014-08-27 | 成都苑东药业有限公司 | 一种噻唑类化合物及其制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4117512A1 (de) * | 1991-05-25 | 1992-11-26 | Schering Ag | 2-phenylbenzo(b)furane und -thiophene, verfahren zu deren herstellung und diese enthaltende pharmazeutische praeparate |
-
1996
- 1996-02-16 TR TR96/00127A patent/TR199600127A2/xx unknown
- 1996-02-27 HU HU9600476A patent/HU226326B1/hu not_active IP Right Cessation
- 1996-02-27 CA CA 2170479 patent/CA2170479C/en not_active Expired - Fee Related
- 1996-02-27 CN CN96105752A patent/CN1086700C/zh not_active Expired - Fee Related
- 1996-02-27 BR BR9600829A patent/BR9600829A/pt not_active IP Right Cessation
- 1996-02-27 CZ CZ1996588A patent/CZ290200B6/cs not_active IP Right Cessation
- 1996-02-27 FI FI960909A patent/FI120345B/fi not_active IP Right Cessation
- 1996-02-27 NO NO19960796A patent/NO314229B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP9600476A2 (hu) | 1999-06-28 |
| CZ58896A3 (en) | 1996-09-11 |
| CN1159448A (zh) | 1997-09-17 |
| NO960796D0 (no) | 1996-02-27 |
| BR9600829A (pt) | 1997-12-30 |
| AU4579796A (en) | 1996-09-05 |
| CZ290200B6 (cs) | 2002-06-12 |
| NO960796L (no) | 1996-08-29 |
| CA2170479A1 (en) | 1996-08-29 |
| FI960909A0 (fi) | 1996-02-27 |
| AU699753B2 (en) | 1998-12-17 |
| HU226326B1 (en) | 2008-08-28 |
| TR199600127A2 (tr) | 1996-10-21 |
| FI120345B (fi) | 2009-09-30 |
| CA2170479C (en) | 2009-04-14 |
| HUP9600476A3 (en) | 1999-07-28 |
| CN1086700C (zh) | 2002-06-26 |
| HU9600476D0 (en) | 1996-04-29 |
| FI960909A (fi) | 1996-08-29 |
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