NO314142B1 - Nye strukturelle analoger av vitamin D - Google Patents
Nye strukturelle analoger av vitamin D Download PDFInfo
- Publication number
- NO314142B1 NO314142B1 NO19960099A NO960099A NO314142B1 NO 314142 B1 NO314142 B1 NO 314142B1 NO 19960099 A NO19960099 A NO 19960099A NO 960099 A NO960099 A NO 960099A NO 314142 B1 NO314142 B1 NO 314142B1
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- Norway
- Prior art keywords
- mmol
- solution
- hexane
- synthesis
- compound
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- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 title abstract description 72
- 229930003316 Vitamin D Natural products 0.000 title abstract description 69
- 235000019166 vitamin D Nutrition 0.000 title abstract description 69
- 239000011710 vitamin D Substances 0.000 title abstract description 69
- 150000003710 vitamin D derivatives Chemical class 0.000 title abstract description 69
- 229940046008 vitamin d Drugs 0.000 title abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 122
- 239000003814 drug Substances 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 8
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- 210000004027 cell Anatomy 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
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- 150000001450 anions Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 15
- 239000011575 calcium Substances 0.000 claims description 15
- 229910052791 calcium Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
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- 239000005556 hormone Substances 0.000 claims description 11
- 229940088597 hormone Drugs 0.000 claims description 11
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 8
- 230000006698 induction Effects 0.000 claims description 8
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- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
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- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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- 239000013543 active substance Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 566
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 57
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 54
- 238000001704 evaporation Methods 0.000 description 50
- 230000008020 evaporation Effects 0.000 description 50
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 48
- 239000002244 precipitate Substances 0.000 description 46
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- 238000001914 filtration Methods 0.000 description 41
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 38
- 229920006395 saturated elastomer Polymers 0.000 description 38
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- 238000001035 drying Methods 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
- -1 (4-hydroxy-4-methyl)-pentyl Chemical group 0.000 description 31
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 31
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 26
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 20
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 20
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 18
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 17
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
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- Organic Chemistry (AREA)
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP93202037 | 1993-07-09 | ||
PCT/EP1994/002294 WO1995001960A1 (fr) | 1993-07-09 | 1994-07-07 | Nouveaux analogues structuraux de la vitamine d |
Publications (3)
Publication Number | Publication Date |
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NO960099D0 NO960099D0 (no) | 1996-01-09 |
NO960099L NO960099L (no) | 1996-03-08 |
NO314142B1 true NO314142B1 (no) | 2003-02-03 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19960099A NO314142B1 (no) | 1993-07-09 | 1996-01-09 | Nye strukturelle analoger av vitamin D |
Country Status (16)
Country | Link |
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US (2) | US6017907A (fr) |
EP (2) | EP0972762B1 (fr) |
JP (2) | JP4235256B2 (fr) |
CN (1) | CN1103755C (fr) |
AT (2) | ATE191712T1 (fr) |
AU (1) | AU699200B2 (fr) |
CA (1) | CA2166898C (fr) |
DE (2) | DE69433220T2 (fr) |
DK (2) | DK0972762T3 (fr) |
ES (2) | ES2209327T3 (fr) |
GR (1) | GR3033856T3 (fr) |
NO (1) | NO314142B1 (fr) |
NZ (1) | NZ271332A (fr) |
PT (2) | PT972762E (fr) |
RU (1) | RU2153491C2 (fr) |
WO (1) | WO1995001960A1 (fr) |
Families Citing this family (58)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1995001960A1 (fr) * | 1993-07-09 | 1995-01-19 | Laboratoire Theramex S.A. | Nouveaux analogues structuraux de la vitamine d |
US5661140A (en) * | 1994-11-21 | 1997-08-26 | Wisconsin Alumni Research Foundation | 18-nor-vitamin D compounds |
AU4235696A (en) * | 1994-11-21 | 1996-06-17 | Wisconsin Alumni Research Foundation | 18,19-dinor-vitamin d compounds |
ATE189812T1 (de) * | 1995-10-30 | 2000-03-15 | Hoffmann La Roche | 1-alpha, 26-dihydroxy-d-homo-vitamin d3 |
CN1201452A (zh) * | 1995-10-31 | 1998-12-09 | 弗·哈夫曼-拉罗切有限公司 | 24-高-26,27-六氟-胆钙化甾醇 |
US5716946A (en) * | 1996-02-13 | 1998-02-10 | Wisconsin Alumni Research Foundation | Multiple sclerosis treatment |
DE19619036A1 (de) | 1996-04-30 | 1997-11-13 | Schering Ag | Neue Vitamin D-Derivate mit carbo- oder heterocyclischen Substituenten an C-25, Verfahren zu ihrer Herstellung und die Verwendung zur Herstellung von Arzneimitteln |
ES2173586T3 (es) * | 1997-05-23 | 2002-10-16 | Basilea Pharmaceutica Ag | Derivados de ciclohexandiol. |
AU735676B2 (en) * | 1997-06-10 | 2001-07-12 | Mrc Holdings Pty Limited | Method of treatment of liver tumours and pharmaceutical compositions for use therein |
AUPO727097A0 (en) | 1997-06-10 | 1997-07-03 | Unisearch Limited | Method of treatment of hepatoma and pharmaceutical compositions for use therein |
AU1022999A (en) | 1997-09-08 | 1999-03-29 | F. Hoffmann-La Roche Ag | 1,3-dihydroxy-20,20-dialkyl-vitamin d3 analogs |
US5919986A (en) * | 1997-10-17 | 1999-07-06 | Hoffmann-La Roche Inc. | D-homo vitamin D3 derivatives |
AU2549099A (en) * | 1998-02-24 | 1999-09-15 | Chugai Seiyaku Kabushiki Kaisha | 24-hydroxyvitamin d derivatives |
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1994
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