Vitamin D derivatives with phosphorus atoms in the side chains
First Claim
Patent Images
1. A Vitamin D derivative compound of formula I:
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in whichY1 means a hydrogen atom, a hydroxyl group, a fluorine, chlorine or bromine atom or a group —
O(CO)R5, in which R5 is an aliphatic or aromatic radical with 1 to 12 C atoms, Y2 means a hydrogen atom or a group —
(CO)R6, in which R6 is an aliphatic or aromatic radical with 1 to 12 C atoms, and group Y2O can be present both in the naturally occurring situation (3β
) and in the epimeric situation (3α
), R1 and R2 each mean a hydrogen atom or together an exocyclic methylene group, R3 and R4 independently of one another, mean a hydrogen atom, a chlorine or fluorine atom, an alkyl group with 1 to 4 carbon atoms, together a methylene group or together with the quaternary carbon atom to which they are bonded, a 3- to 7-membered, saturated or unsaturated carbocyclic ring, V and W together mean an E-double bond X1 and X2, independently of one another, mean a hydrogen atom, a hydroxyl group, a group —
OR7 or —
O(CO)R7, in which R7 is an aliphatic or aromatic radical with 1 to 12 C atoms, or a group PO(OR8)2, a group PO(N(R8)2)2, a group PO(R8)2, a group OPO(OR8)2, a group OPO(N(R8)2)2, a group OPO(R8)2, a group CH2—
PO(OR8)2, a group CH2—
PO(N(R8)2)2 or a group CH2—
PO(R8)2, in which R8, independently of one another, are a hydrogen atom or an aliphatic or aromatic radical with 1 to 12 C atoms,
or X1 and X2 together stand for a carbonyl group, p means the number 1 or 0, E1 means a group PO(OR9)2, a group PO(N(R9)2)2, or a group PO(R9)2, in which R9 independently of one another, are a hydrogen atom or an aliphatic or aromatic radical with 1 to 12 C atoms, E2 means a group PO(OR9)2, a group PO(N(R9)2)2, a group PO(R9)2, a halogen atom (fluorine, chlorine, bromine), an aliphatic or aromatic radical with 1 to 12 C atoms or a hydrogen atom, Q means a hydrogen atom, an aliphatic or aromatic radical with 1 to 12 C atoms, a hydroxyl group, a group —
O(CO)R10, a fluorine, chlorine, or bromine atom, an amino group or an NHR10 or N(R10)2 group, in which R10 is an aliphatic or aromatic radical with 1 to 12 C atoms,
or X1 and E2 together mean a double bond and at the same time X2 means a hydrogen atom or group O—
Z, in which Z means an aliphatic or aromatic radical with 1 to 12 C atoms, an aliphatic or aromatic acyl group with 1 to 12 C atoms or a group E2,
or X1, X2, E2 and Q together mean a triple bond.
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Abstract
Described are new vitamin D derivatives such as of the formula (I) detailed in this disclosure. Also described are methods for preparing these derivatives, inter mediates used to prepare the derivatives and use of the derivatives as pharmaceutical agents.
19 Citations
16 Claims
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1. A Vitamin D derivative compound of formula I:
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in which Y1 means a hydrogen atom, a hydroxyl group, a fluorine, chlorine or bromine atom or a group —
O(CO)R5, in which R5 is an aliphatic or aromatic radical with 1 to 12 C atoms,Y2 means a hydrogen atom or a group —
(CO)R6, in which R6 is an aliphatic or aromatic radical with 1 to 12 C atoms,and group Y2O can be present both in the naturally occurring situation (3β
) and in the epimeric situation (3α
),R1 and R2 each mean a hydrogen atom or together an exocyclic methylene group, R3 and R4 independently of one another, mean a hydrogen atom, a chlorine or fluorine atom, an alkyl group with 1 to 4 carbon atoms, together a methylene group or together with the quaternary carbon atom to which they are bonded, a 3- to 7-membered, saturated or unsaturated carbocyclic ring, V and W together mean an E-double bond X1 and X2, independently of one another, mean a hydrogen atom, a hydroxyl group, a group —
OR7 or —
O(CO)R7, in which R7 is an aliphatic or aromatic radical with 1 to 12 C atoms, or a group PO(OR8)2, a group PO(N(R8)2)2, a group PO(R8)2, a group OPO(OR8)2, a group OPO(N(R8)2)2, a group OPO(R8)2, a group CH2—
PO(OR8)2, a group CH2—
PO(N(R8)2)2 or a group CH2—
PO(R8)2, in whichR8, independently of one another, are a hydrogen atom or an aliphatic or aromatic radical with 1 to 12 C atoms,
orX1 and X2 together stand for a carbonyl group, p means the number 1 or 0, E1 means a group PO(OR9)2, a group PO(N(R9)2)2, or a group PO(R9)2, in which R9 independently of one another, are a hydrogen atom or an aliphatic or aromatic radical with 1 to 12 C atoms, E2 means a group PO(OR9)2, a group PO(N(R9)2)2, a group PO(R9)2, a halogen atom (fluorine, chlorine, bromine), an aliphatic or aromatic radical with 1 to 12 C atoms or a hydrogen atom, Q means a hydrogen atom, an aliphatic or aromatic radical with 1 to 12 C atoms, a hydroxyl group, a group —
O(CO)R10, a fluorine, chlorine, or bromine atom, an amino group or an NHR10 or N(R10)2 group, in whichR10 is an aliphatic or aromatic radical with 1 to 12 C atoms,
orX1 and E2 together mean a double bond and at the same time X2 means a hydrogen atom or group O—
Z, in whichZ means an aliphatic or aromatic radical with 1 to 12 C atoms, an aliphatic or aromatic acyl group with 1 to 12 C atoms or a group E2,
orX1, X2, E2 and Q together mean a triple bond. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16)
R3=H and R4=methyl or R3=methyl and R4=H or R3=F and R4=methyl or R3=methyl and R4=F or R3=methyl and R4=methyl or R3 and R4 together form a methylene group or R3 and R4 together with tertiary carbon atom 20 form a cyclopropyl ring.
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6. Compound of general formula I according to claim 1, wherein V and W and X1 and E2 in each case mean an E-double bond, and X2 and Q are hydrogen atoms.
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7. Compound of general formula I according to claim 1, wherein V and W together mean an E-double bond, X1 and E2 form an E- or Z-double bond, X2 is a group —
- OZ, and Q means a hydrogen atom.
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8. Compound of general formula I according to claim 1, wherein X1, X2, E2, and Q together mean a triple bond.
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9. Compound of general formula I according to claim 1, wherein E2 and Q mean halogen atoms.
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10. Compounds of general formula I according to claim 1, wherein Y1 means a hydroxyl group or —
- O(CO)R5, and Y2 means a hydrogen atom or —
(CO)R6.
- O(CO)R5, and Y2 means a hydrogen atom or —
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12. A compound of claim 1, wherein R1 and R2 together mean an exocyclic methylene group.
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13. A method for producing a pharmaceutical agent which comprises incorporating at least one compound of the formula I of claim 1 together with at least one pharmaceutically acceptable vehicle.
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14. A method for therapy of or prophylaxis against osteoporosis which comprises administering to a patient in need thereof a pharmaceutical composition comprising a compound of the formula I of claim 1.
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15. A method for generating new bone material in a patient which comprises administering to a patient in need thereof a pharmaceutical composition comprising a compound of the formula I of claim 1.
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16. A method for treating a disease characterized by hyperproliferation and deficient cell differentiation which comprises administering to a patient in need thereof a pharmaceutical composition comprising a compound of the formula I of claim 1.
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11. Compounds of general formula I, namely:
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(5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipentyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipentyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipentyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diphenyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diphenyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diphenyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24a,24a-diyl)bis[phosphonic acid dinethyl ester] (5Z,7E 22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24a,24a-diyl)bis[phosphonic acid diethyl ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24a,24a-diyl)bis[phosphonic acid dipropyl ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24a,24a-diyl)bis[phosphonic acid dibutyl ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a,24a-diyl)bis[phosphonic acid bis(1-methylethyl)ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24a,24a-diyl)bis[phosphonic acid diphenyl ester] (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy -24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-24-(Diphenylphosphinyl)-9,10-secochola-5,7,10(19),22-tetraene-1,3-diol (5Z,7E,22E)-(1S,3R)-24-(Dimethylphosphinyl)-9,10-secochola-5,7,10(19),22-tetraene-1,3-diol (5Z,7E,22E)-(1S,3R)-24-(Diethylphosphinyl)-9,10-secochola-5,7,10(19),22-tetraene-1,3-diol (5Z,7E,22E)-(1S,3R)-24-(Dipropylphosphinyl)-9,10-secochola-5,7,10(19),22-tetraene-1,3-diol (5Z,7E,22E)-(1S,3R)-24-(Dibutylphosphinyl)-9,10-secochola-5,7,10(19),22-tetraene-1,3-diol (5Z,7E,22E,24E)-(1S,3R)-Phosphoric acid[1,3-dihydroxy-24a-(dimethoxy)phosphinyl-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24-yl]dimethyl ester (5Z,7E,22E,24Z)-(1S,3R)-Phosphoric acid[1,3-dihydroxy-24a-(dimethoxy)phosphinyl-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24-yl]dimethyl ester (5Z,7E,22E,24E)-(1S,3R)-Phosphoric acid[24a-(diethoxy)phosphinyl-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24-yl]diethyl ester (5Z,7E,22E,24Z)-(1S,3R)-Phosphoric acid[24a-(diethoxy)phosphinyl-1,3-dihydroxy-24a-homo-9,10secochola-5,7,10(19),22,24-pentaen-24-yl]diethyl ester (5Z,7E,22E,24E)-(1S,3R)-Phosphoric acid[1,3-dihydroxy-24a-(dipropoxy)phosphinyl-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24-yl]dipropyl ester (5Z,7E,22E,24Z)-(1S,3R)-Phosphoric acid[1,3-dihydroxy-24a-(dipropoxy)phosphinyl-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24-yl]dipropyl ester (5Z,7E,22E,24E)-(1S,3R)-Phosphoric acid[24a-(dibutoxy)phosphinyl-1,3-dihydroxy-24a-homo-9,10secochola-5,7,10(19),22,24-pentaen-24-yl]dibutyl ester (5Z,7E,22E,24Z)-(1S,3R)-Phosphoric acid[24a-(dibutoxy)phosphinyl-1,3-dihydroxy-24a-homo-9,10secochola-5,7,10(19),22,24-pentaen-24-yl]dibutyl ester (5Z,7E,22E,24E)-(1S,3R)-Phosphoric acid[24a-[bis(1-methylethoxy)phosphinyl]-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24-yl]bis(1-methylethyl)ester (5Z,7E,22E,24Z)-(1S,3R)-Phosphoric acid[24a-[bis(1-methylethoxy)phosphinyl]-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24-yl]bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-monomethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-monoethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-mono(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-monopropyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-monobutyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid-monomethyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid-monoethyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid-mono(1-methylethyl)ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid-monopropyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid-monobutyl ester (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24,24a-diyl)bis[phosphonic acid dimethyl ester](5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24,24a-diyl)bis[phosphonic acid diethyl ester](5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24,24a-diyl)bis[phosphonic acid-bis(1-methylethyl)ester](5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24,24a-diyl)bis[phosphonic acid dipropyl ester](5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraene-24,24a-diyl)bis[phosphonic acid dibutyl ester](5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl)bis[phosphonic acid dimethyl ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl)bis[phosphonic acid diethyl ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl)bis[phosphonic acid-bis(1-methylethyl)ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl)bis[phosphonic acid dipropyl ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl]bis[phosphonic acid dibutyl ester] (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-nor-9,10-secocholesta-5,7,10(19),22-tetraene-26,27-diyl)bis[phosphonic acid] (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaene-24a,24a-diyl)bis[phosphonic acid dimethyl ester] (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaene-24a,24a-diyl)bis[phosphonic acid diethyl ester] (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaene-24a,24a-diyl)bis[phosphonic acid-bis(1-methylethyl)ester] (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaene-24a,24a-diyl)bis[phosphonic acid dipropyl ester] (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaene-24a,24a-diyl)bis[phosphonic acid dibutyl ester] (5Z,7E,22E,24E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaene-24a,24a-diyl)bis[phosphonic acid] (5Z,7E,22E,24Z)-(1S,3R)-(24a-Chloro-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E,24Z)-(1S,3R)-(24a-Chloro-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E,24Z)-(1S,3R)-(24a-Chloro-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E,24Z)-(1S,3R)-(24a-Chloro-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E,24Z)-(1S,3R)-(24a-Chloro-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E,24Z)-(1S,3R)-(24a-Chloro-1,3-dihydroxy-24a-homo-9,10-secochola-5,7,10(19),22,24-pentaen-24a-yl)phosphonic acid (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid-monomethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid-monoethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid-mono-(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid-monopropyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid-monobutyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24a-homo-9,10secochola-5,7,10(19),22-tetraen-24-in-24a-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24S)-24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9, 10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Dichloro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24R)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24S)-(24a,24a-Difluoro-1,3,24-trihydroxy-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid (5Z,7E,22E)-(1S,3R)-(24a,24a-Difluoro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Difluoro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Difluoro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Difluoro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Difluoro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Dichloro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Dichloro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Dichloro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Dichloro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R)-(24a,24a-Dichloro-1,3-dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R)-(26,27-Diethenyl-1,3-dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(26,27-Diethenyl-1,3-dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(26,27-Diethenyl-1,3-dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(26,27-Diethenyl-1,3-dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid propyl ester (5Z,7E,22E)-(1S,3R)-(26,27-Diethenyl-1,3-dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid butyl ester (5Z,7E,22E)-(1S,3R)-(26,27-Diethenyl-1,3-dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-26-ethenyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dimethyl ester(5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-26-ethenyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid diethyl ester(5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-26-ethenyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid-bis(1-methylethyl)ester(5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-26-ethenyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dipropyl ester(5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-26-ethenyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dibutyl ester(5Z,7E,22E)-(1S,3R,24ξ
)-(1,3-Dihydroxy-26-ethenyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid(5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-26,27-dimethyl-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-26,27-dimethyl-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-26,27-dimethyl-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-26,27-dimethyl-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-26,27-dimethyl-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-26,27-dimethyl-24-oxo-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,25R)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,25S)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,25R)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,25S)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,25R)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,25S)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,25R)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,25S)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,25R)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,25S)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,25R)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,25S)-(1,3-Dihydroxy-26-methyl-24-oxo-27-nor-9,10-secocholesta-5,7,10(19),22-tetraen-25-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R,24S)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid (5Z,7E,22E)-(1S,3R,24R)-(1,3,24-Trihydroxy-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid propyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3R)-(1,3-Dihydroxy-24-oxo-9,10-secochola-5,7,10(19),22-tetraen-24-yl)phosphonic acid (5Z,7E,22E)-(1S,3S)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dimethyl ester (5Z,7E,22E)-(1S,3S)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid diethyl ester (5Z,7E,22E)-(1S,3S)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid-bis(1-methylethyl)ester (5Z,7E,22E)-(1S,3S)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dipropyl ester (5Z,7E,22E)-(1S,3S)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid dibutyl ester (5Z,7E,22E)-(1S,3S)-(1,3-Dihydroxy-24-oxo-24a-homo-9,10-secochola-5,7,10(19),22-tetraen-24a-yl)phosphonic acid.
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Specification