FI109686B - Menetelmä uusien D-vitamiinianalogien valmistamiseksi - Google Patents
Menetelmä uusien D-vitamiinianalogien valmistamiseksi Download PDFInfo
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- FI109686B FI109686B FI951447A FI951447A FI109686B FI 109686 B FI109686 B FI 109686B FI 951447 A FI951447 A FI 951447A FI 951447 A FI951447 A FI 951447A FI 109686 B FI109686 B FI 109686B
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- ether
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- 238000000034 method Methods 0.000 title claims description 162
- 238000002360 preparation method Methods 0.000 title claims description 103
- 230000008569 process Effects 0.000 title claims description 10
- 150000003710 vitamin D derivatives Chemical class 0.000 title description 15
- 229930003316 Vitamin D Natural products 0.000 title description 14
- 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 description 14
- 235000019166 vitamin D Nutrition 0.000 title description 14
- 239000011710 vitamin D Substances 0.000 title description 14
- 229940046008 vitamin d Drugs 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
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- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 7
- 150000001450 anions Chemical class 0.000 claims abstract description 4
- 238000007699 photoisomerization reaction Methods 0.000 claims abstract description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- -1 p-toluenesulfonyloxy Chemical group 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
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- QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 206010028537 myelofibrosis Diseases 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 230000031990 negative regulation of inflammatory response Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008085 renal dysfunction Effects 0.000 description 1
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000004927 skin cell Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 102000009310 vitamin D receptors Human genes 0.000 description 1
- 108050000156 vitamin D receptors Proteins 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical class 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-YRZJJWOYSA-N 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB929220439A GB9220439D0 (en) | 1992-09-28 | 1992-09-28 | Chemical compounds |
| GB9220439 | 1992-09-28 | ||
| DK9300311 | 1993-09-27 | ||
| PCT/DK1993/000311 WO1994007852A1 (en) | 1992-09-28 | 1993-09-27 | Novel vitamin d analogues |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI951447L FI951447L (fi) | 1995-03-27 |
| FI951447A0 FI951447A0 (fi) | 1995-03-27 |
| FI109686B true FI109686B (fi) | 2002-09-30 |
Family
ID=10722627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI951447A FI109686B (fi) | 1992-09-28 | 1995-03-27 | Menetelmä uusien D-vitamiinianalogien valmistamiseksi |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5589471A (de) |
| EP (1) | EP0662954B1 (de) |
| JP (1) | JPH08501572A (de) |
| KR (1) | KR100295976B1 (de) |
| AT (1) | ATE157085T1 (de) |
| AU (1) | AU668774B2 (de) |
| CA (1) | CA2140247C (de) |
| DE (1) | DE69313295T2 (de) |
| DK (1) | DK0662954T3 (de) |
| ES (1) | ES2107682T3 (de) |
| FI (1) | FI109686B (de) |
| GB (1) | GB9220439D0 (de) |
| GR (1) | GR3025280T3 (de) |
| NZ (1) | NZ256390A (de) |
| RU (1) | RU2165923C2 (de) |
| WO (1) | WO1994007852A1 (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6242434B1 (en) | 1997-08-08 | 2001-06-05 | Bone Care International, Inc. | 24-hydroxyvitamin D, analogs and uses thereof |
| GB9526208D0 (en) * | 1995-12-21 | 1996-02-21 | Res Inst Medicine Chem | Chemical compounds |
| US20030220234A1 (en) | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| US5972917A (en) * | 1998-05-29 | 1999-10-26 | Bone Care Int Inc | 1 α-hydroxy-25-ene-vitamin D, analogs and uses thereof |
| ES2204165T3 (es) | 1998-05-29 | 2004-04-16 | Bone Care International, Inc. | Procedimiento para la preparacion de compuestos 25-eno-vitamina d hidroxilo. |
| US6359012B1 (en) | 1999-12-22 | 2002-03-19 | Bone Care International, Inc. | Method for making 24(S)-hydroxyvitamin D2 |
| WO2003033526A2 (en) | 2001-10-19 | 2003-04-24 | Isotechnika Inc. | Synthesis of cyclosporin analogs |
| KR20060058134A (ko) * | 2003-09-19 | 2006-05-29 | 화이자 프로덕츠 인코포레이티드 | 2-알킬리덴-19-노르-비타민 디 유도체 및비스포스포네이트의 조합을 포함하는 약학 조성물 및 방법 |
| US7094775B2 (en) | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
| EP1812011A1 (de) | 2004-11-12 | 2007-08-01 | Bioxell S.p.a. | Kombinierte verwendung von vitamin-d-derivaten und antiproliferativen mitteln zur behandlung von blasenkrebs |
| GB2473782B (en) | 2008-07-10 | 2012-09-26 | Peter M Breining | Luminescent cycle regulator and fertility indicator |
| AU2010208323B2 (en) | 2009-01-27 | 2016-03-10 | Berg Llc | Vitamin D3 and analogs thereof for alleviating side effects associated with chemotherapy |
| EP2464357B1 (de) | 2009-08-14 | 2019-05-22 | Berg LLC | Vitamin d3 und analoge davon zur behandlung von alopezie |
| SG10201709894RA (en) | 2013-05-29 | 2018-01-30 | Berg Llc | Preventing or mitigating chemotherapy induced alopecia using vitamin d |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8904154D0 (en) * | 1989-02-23 | 1989-04-05 | Leo Pharm Prod Ltd | Chemical compounds |
| ES2093180T3 (es) * | 1991-07-05 | 1996-12-16 | Duphar Int Res | Compuesto de vitamina d, metodo de preparar este compuesto y producto intermedio de dicho metodo. |
-
1992
- 1992-09-28 GB GB929220439A patent/GB9220439D0/en active Pending
-
1993
- 1993-09-27 RU RU94046458/04A patent/RU2165923C2/ru not_active IP Right Cessation
- 1993-09-27 NZ NZ256390A patent/NZ256390A/en unknown
- 1993-09-27 EP EP93921832A patent/EP0662954B1/de not_active Expired - Lifetime
- 1993-09-27 WO PCT/DK1993/000311 patent/WO1994007852A1/en not_active Ceased
- 1993-09-27 JP JP6508597A patent/JPH08501572A/ja not_active Ceased
- 1993-09-27 KR KR1019950700151A patent/KR100295976B1/ko not_active Expired - Fee Related
- 1993-09-27 DK DK93921832.7T patent/DK0662954T3/da active
- 1993-09-27 ES ES93921832T patent/ES2107682T3/es not_active Expired - Lifetime
- 1993-09-27 DE DE69313295T patent/DE69313295T2/de not_active Expired - Fee Related
- 1993-09-27 AT AT93921832T patent/ATE157085T1/de not_active IP Right Cessation
- 1993-09-27 AU AU51080/93A patent/AU668774B2/en not_active Ceased
- 1993-09-27 CA CA002140247A patent/CA2140247C/en not_active Expired - Fee Related
- 1993-09-27 US US08/362,550 patent/US5589471A/en not_active Expired - Fee Related
-
1995
- 1995-03-27 FI FI951447A patent/FI109686B/fi active
-
1997
- 1997-11-05 GR GR970402918T patent/GR3025280T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2140247A1 (en) | 1994-04-14 |
| US5589471A (en) | 1996-12-31 |
| RU2165923C2 (ru) | 2001-04-27 |
| JPH08501572A (ja) | 1996-02-20 |
| GR3025280T3 (en) | 1998-02-27 |
| NZ256390A (en) | 1997-06-24 |
| EP0662954B1 (de) | 1997-08-20 |
| ES2107682T3 (es) | 1997-12-01 |
| WO1994007852A1 (en) | 1994-04-14 |
| DK0662954T3 (da) | 1997-12-08 |
| DE69313295D1 (de) | 1997-09-25 |
| CA2140247C (en) | 2003-12-09 |
| ATE157085T1 (de) | 1997-09-15 |
| KR950702529A (ko) | 1995-07-29 |
| RU94046458A (ru) | 1997-01-10 |
| DE69313295T2 (de) | 1998-03-19 |
| GB9220439D0 (en) | 1992-11-11 |
| EP0662954A1 (de) | 1995-07-19 |
| FI951447L (fi) | 1995-03-27 |
| AU5108093A (en) | 1994-04-26 |
| KR100295976B1 (ko) | 2001-11-14 |
| FI951447A0 (fi) | 1995-03-27 |
| AU668774B2 (en) | 1996-05-16 |
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