CA2235584A1 - 24-homo-26,27-hexafluoro-cholecalciferols - Google Patents
24-homo-26,27-hexafluoro-cholecalciferols Download PDFInfo
- Publication number
- CA2235584A1 CA2235584A1 CA002235584A CA2235584A CA2235584A1 CA 2235584 A1 CA2235584 A1 CA 2235584A1 CA 002235584 A CA002235584 A CA 002235584A CA 2235584 A CA2235584 A CA 2235584A CA 2235584 A1 CA2235584 A1 CA 2235584A1
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- Prior art keywords
- compound
- formula
- accordance
- treatment
- homo
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 11
- 208000017520 skin disease Diseases 0.000 claims abstract description 11
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 230000001613 neoplastic effect Effects 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 230000004069 differentiation Effects 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 208000032839 leukemia Diseases 0.000 claims abstract description 7
- 230000035755 proliferation Effects 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
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- 201000011510 cancer Diseases 0.000 claims abstract description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 5
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- 239000000203 mixture Substances 0.000 claims description 24
- 239000011647 vitamin D3 Substances 0.000 claims description 16
- 229940021056 vitamin d3 Drugs 0.000 claims description 16
- 239000000543 intermediate Substances 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
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- -1 alkyl lithium Chemical compound 0.000 description 9
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- JPXMTWWFLBLUCD-UHFFFAOYSA-N nitro blue tetrazolium(2+) Chemical compound COC1=CC(C=2C=C(OC)C(=CC=2)[N+]=2N(N=C(N=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)[N+]([O-])=O)=CC=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=C([N+]([O-])=O)C=C1 JPXMTWWFLBLUCD-UHFFFAOYSA-N 0.000 description 5
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- GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 description 4
- GMRQFYUYWCNGIN-ZVUFCXRFSA-N 1,25-dihydroxy vitamin D3 Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-ZVUFCXRFSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 206010004146 Basal cell carcinoma Diseases 0.000 description 4
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 206010020649 Hyperkeratosis Diseases 0.000 description 4
- 208000001126 Keratosis Diseases 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 4
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 2
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/48—Halogenated derivatives
- C07C35/52—Alcohols with a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US712595P | 1995-10-31 | 1995-10-31 | |
| US60/007,125 | 1995-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2235584A1 true CA2235584A1 (en) | 1997-05-09 |
Family
ID=21724362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002235584A Abandoned CA2235584A1 (en) | 1995-10-31 | 1996-10-23 | 24-homo-26,27-hexafluoro-cholecalciferols |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0874813A1 (ko) |
| JP (1) | JPH10512297A (ko) |
| KR (1) | KR19990067173A (ko) |
| CN (1) | CN1201452A (ko) |
| AU (1) | AU7297496A (ko) |
| CA (1) | CA2235584A1 (ko) |
| MX (1) | MX9803345A (ko) |
| WO (1) | WO1997016423A1 (ko) |
| ZA (1) | ZA968953B (ko) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276284A (zh) * | 2021-12-30 | 2022-04-05 | 正大制药（青岛）有限公司 | 一种氟骨化醇的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8915770D0 (en) * | 1989-07-10 | 1989-08-31 | Leo Pharm Prod Ltd | Chemical compounds |
| US5206230A (en) * | 1991-06-05 | 1993-04-27 | Daikin Industries, Ltd. | Fluorine-containing vitamin D3 analogues and pharmaceutical composition containing the same |
| US6017907A (en) * | 1993-07-09 | 2000-01-25 | Laboratoire Theramex S.A. | Structural analogues of vitamin D |
-
1996
- 1996-10-23 AU AU72974/96A patent/AU7297496A/en not_active Abandoned
- 1996-10-23 CA CA002235584A patent/CA2235584A1/en not_active Abandoned
- 1996-10-23 CN CN96198019A patent/CN1201452A/zh active Pending
- 1996-10-23 JP JP9517038A patent/JPH10512297A/ja active Pending
- 1996-10-23 WO PCT/EP1996/004592 patent/WO1997016423A1/en not_active Application Discontinuation
- 1996-10-23 EP EP96934788A patent/EP0874813A1/en not_active Withdrawn
- 1996-10-23 KR KR1019980703124A patent/KR19990067173A/ko not_active Application Discontinuation
- 1996-10-24 ZA ZA968953A patent/ZA968953B/xx unknown
-
1998
- 1998-04-28 MX MX9803345A patent/MX9803345A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA968953B (en) | 1997-07-30 |
| KR19990067173A (ko) | 1999-08-16 |
| JPH10512297A (ja) | 1998-11-24 |
| EP0874813A1 (en) | 1998-11-04 |
| MX9803345A (es) | 1998-09-30 |
| WO1997016423A1 (en) | 1997-05-09 |
| CN1201452A (zh) | 1998-12-09 |
| AU7297496A (en) | 1997-05-22 |
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