CA2168728A1 - Vitamin d3 derivative and production process thereof - Google Patents
Vitamin d3 derivative and production process thereofInfo
- Publication number
- CA2168728A1 CA2168728A1 CA002168728A CA2168728A CA2168728A1 CA 2168728 A1 CA2168728 A1 CA 2168728A1 CA 002168728 A CA002168728 A CA 002168728A CA 2168728 A CA2168728 A CA 2168728A CA 2168728 A1 CA2168728 A1 CA 2168728A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- hydrogen atom
- vitamin
- atom
- bond
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003704 vitamin D3 derivatives Chemical class 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 6
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002252 acyl group Chemical group 0.000 claims abstract 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract 3
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000000686 lactone group Chemical group 0.000 claims abstract 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229930003316 Vitamin D Natural products 0.000 abstract 1
- 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 abstract 1
- 235000019166 vitamin D Nutrition 0.000 abstract 1
- 239000011710 vitamin D Substances 0.000 abstract 1
- 150000003710 vitamin D derivatives Chemical class 0.000 abstract 1
- 229940046008 vitamin d Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
A vitamin D, derivative represented by the following formula:
(see formula I) wherein, R is, independently, a hydrogen atom, tri(C1 to C7 hydrocarbon) silyl group, C2 to C8 acyl group, or group forming an acetal bond together with an oxygen atom of a hydroxyl group, A is (see formula II) (see formula III) or (see formula IV) where, R1 is a methyl group or methylene group, and when R1 is a methylene group, the bond between the R1 and the 3-position of the lactone ring is a double bond, R2 is a hydrogen atom or C1 to C3 alkyl group, R3 is a hydrogen atom, or R2 and R3 together indicate a substitutable single methylene group.
(see formula I) wherein, R is, independently, a hydrogen atom, tri(C1 to C7 hydrocarbon) silyl group, C2 to C8 acyl group, or group forming an acetal bond together with an oxygen atom of a hydroxyl group, A is (see formula II) (see formula III) or (see formula IV) where, R1 is a methyl group or methylene group, and when R1 is a methylene group, the bond between the R1 and the 3-position of the lactone ring is a double bond, R2 is a hydrogen atom or C1 to C3 alkyl group, R3 is a hydrogen atom, or R2 and R3 together indicate a substitutable single methylene group.
Claims (3)
1. A vitamin D3 derivative represented by the following formula (I):
wherein, R is, independently, a hydrogen atom, tri(C1 to C7 hydrocarbon) silyl group, C2 to CB acyl group, or a group forming an acetal bond together with an oxygen atom of a hydroxyl group, A is where, R1 is a methyl group or methylene group and when R1 is a methylene group, the bond between the R1 and the 3-position of the lactone ring is a double bond, R2 is a hydrogen atom or C1 to C3 alkyl group, R3 is a hydrogen atom, or R2 and R3 together indicate a single methylene group, which is substitutable with a t-butyl group, phenyl group or methyl group.
wherein, R is, independently, a hydrogen atom, tri(C1 to C7 hydrocarbon) silyl group, C2 to CB acyl group, or a group forming an acetal bond together with an oxygen atom of a hydroxyl group, A is where, R1 is a methyl group or methylene group and when R1 is a methylene group, the bond between the R1 and the 3-position of the lactone ring is a double bond, R2 is a hydrogen atom or C1 to C3 alkyl group, R3 is a hydrogen atom, or R2 and R3 together indicate a single methylene group, which is substitutable with a t-butyl group, phenyl group or methyl group.
2. A vitamin D3 derivative as claimed in claim 1 represented by the following formula (1-1):
wherein the asymmetric center of the C-1 position of the cyclopentene ring of the formula (1-1) is the (S) configuration and the asymmetric center of the C-4 position is the (S) configuration.
wherein the asymmetric center of the C-1 position of the cyclopentene ring of the formula (1-1) is the (S) configuration and the asymmetric center of the C-4 position is the (S) configuration.
3. A cyclopentene derivative represented by the following formula (1-2):
wherein R~ is a hydrogen atom, a tri(C1 to C7 hydrocarbon) silyl group, a C2 to C7 acyl group, or a group forming an acetal bond together with an oxygen atom of a hydroxyl group, and X1 is a bromine atom or iodine atom.
wherein R~ is a hydrogen atom, a tri(C1 to C7 hydrocarbon) silyl group, a C2 to C7 acyl group, or a group forming an acetal bond together with an oxygen atom of a hydroxyl group, and X1 is a bromine atom or iodine atom.
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6/125144 | 1994-06-07 | ||
| JP12514494 | 1994-06-07 | ||
| JP6/220185 | 1994-09-14 | ||
| JP22018594 | 1994-09-14 | ||
| JP22322994 | 1994-09-19 | ||
| JP6/223229 | 1994-09-19 | ||
| PCT/JP1995/001145 WO1995033716A1 (en) | 1994-06-07 | 1995-06-07 | Vitamin d3 derivative and process for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2168728A1 true CA2168728A1 (en) | 1995-12-14 |
| CA2168728C CA2168728C (en) | 2010-07-27 |
Family
ID=42371375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2168728A Expired - Fee Related CA2168728C (en) | 1994-06-07 | 1995-06-07 | Vitamin d3 derivative and production process thereof |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2168728C (en) |
-
1995
- 1995-06-07 CA CA2168728A patent/CA2168728C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2168728C (en) | 2010-07-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS567734A (en) | Preparation of quinone derivative | |
| CA2119261A1 (en) | Novel sidechain-bearing taxanes and intermediates thereof | |
| CA2147883A1 (en) | Cyclohexanol Derivative, Cool Feeling and Cool Feeling Composition Containing the Same, Process for Producing the Derivative and Intermediate Therefor | |
| JPS55164685A (en) | Novel maytansinoid compound and its preparation | |
| CA2412554A1 (en) | 3-substituted morphines | |
| CA2046126A1 (en) | 2-thienylglycidic derivative, process for its preparation and its use as synthesis intermediate | |
| EP0854139A3 (en) | Vitamin D3 derivative and production process thereof | |
| CA2033531A1 (en) | Azaoxindole derivatives | |
| CA2299710A1 (en) | Aryloxyaniline derivatives | |
| EP1437359A3 (en) | Novel 3,6-Hemiketals from the Class of 9a-Azalides | |
| CA2235298A1 (en) | Isoxazole derivatives | |
| CA2168728A1 (en) | Vitamin d3 derivative and production process thereof | |
| CA2445651A1 (en) | Cathartic composition comprising halogenated prostaglandin derivatives | |
| HU9503665D0 (en) | Process for stereoselective reducing alpha, beta-unsaturated ketones | |
| KR840005122A (en) | Method for preparing methyl flavone derivatives | |
| CA2059632A1 (en) | Reveromycin a, method for preparing same, and antitumor agent and antifungal agent comprising the same | |
| CA2021338A1 (en) | Imidazoquinolone derivatives | |
| EP0355689A3 (en) | Pyrano [f] quinoline derivatives and pharmaceutical compositions containing the same | |
| CA2177227A1 (en) | Process for the preparation of optically active piperazine-2-carboxylic acid derivatives | |
| CA2164152A1 (en) | New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof | |
| FR2426697A1 (en) | NEW ANTIBIOTIC SUBSTANCE OBTAINED FROM A MICROORGANISM OF THE GENUS ACTINOPLANES | |
| EP0947514A4 (en) | Novel phenanethridinium derivatives | |
| KR930700412A (en) | Method for preparing α-amino-β, δ-diol derivatives | |
| AU6176586A (en) | Intermediates for the production of chromones and thiochromones | |
| JPS5432448A (en) | Preparation of cyclopentanone derivative |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140609 |
|
| MKLA | Lapsed |
Effective date: 20140609 |