Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – 9,10-seco- cyclopentanohydrophenanthrene ring system doai
Reexamination Certificate
2000-12-18
2002-04-23
Pryor, Alton (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
9,10-seco- cyclopentanohydrophenanthrene ring system doai
C552S653000
Reexamination Certificate
active
06376480
ABSTRACT:
This invention relates to vitamin D derivatives with substituents at C-25 of general formula I
in which
Y
1
means a hydrogen atom, a hydroxyl group, an alkanoyloxy group with 1 to 12 C atoms or an aroyloxy group,
Y
2
means a hydrogen atom or an alkanoyl group with 1 to 12 C atoms or an aroyl group,
R
1
and R
2
each mean a hydrogen atom or together an exocyclic methylene group,
R
3
and R
4
, 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 quaternary carbon atom 20 a 3- to 7-membered, saturated or unsaturated carbocyclic ring,
A and B together mean a keto group or A means a group OR′ and B means a hydrogen atom or B means a group OR′ and A means a hydrogen atom, whereby R′ is a hydrogen atom or a straight-chain or branched-chain, saturated alkanoyl group with up to 9 carbon atoms or an aroyl group,
R
5
and R
6
at the same time each mean a hydrogen atom, a chlorine or fluorine atom, a trifluoromethyl group, a straight-chain or branched-chain, saturated or unsaturated hydrocarbon radical with up to 4 carbon atoms or R
5
and R
6
together with carbon atom 25 mean a 3- to 7-membered, saturated or unsaturated carbocyclic ring and
Z means a straight-chain or branched-chain, saturated or unsaturated hydrocarbon radical with up to 12 carbon atoms, which can also have a carbocyclic or heterocyclic partial structure and at any positions can exhibit keto groups, hydroxy groups (in &agr;- or &bgr;-position) that in turn can be etherified or esterified, amino groups, halogen atoms or carboxylic acid ester or amide units and is linked by a carbonyl group, a hydroxymethylene group or an ethenediyl unit C—CH═CH—, E- or Z-geometry) with carbon atom 25,
and processes for their production, intermediate products for these processes, pharmaceutical preparations that contain these compounds as well as their use for the production of pharmaceutical agents.
The alkanoyl or alkanoyloxy groups with 1 to 12 C atoms that are possible for radicals Y
1
and Y
2
are derived especially from saturated carboxylic acids. These radicals can be cyclic, acyclic, carbocyclic or heterocyclic. The preferred radicals are derived from C
1
to C
9
, especially C
2
to C
5
alkanecarboxylic acids, such as, for example, acetyl(oxy), propionyl(oxy), butyryl(oxy).
As aroyl(oxy) groups, the benzoyl(oxy) groups and substituted benzoyl(oxy) groups are preferred.
For R
3
and R
4
, the following preferred combinations apply: R
3
=H, R
4
=methyl or R
3
=methyl, R
4
=H; R
3
=F, R
4
=methyl or R
3
=methyl, R
4
=F; R
3
, R
4
=methyl; R
3
and R
4
together form a methylene group or together with tertiary carbon atom 20 form a cyclopropyl ring.
For A and B, the following preferred combinations apply:
A=OH, B=H or A=H, B=OH and A and B form a carbonyl group.
For R
5
and R
6
, the following preferred combinations apply:
R
5
, R
6
=methyl or ethyl; R
5
and R
6
together with carbon atom form a cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl ring.
Especially preferred are the cases R
5
, R
6
=methyl, and R
5
and R
6
together with carbon atom 25 form a cyclopropyl ring.
For Z, the following preferences apply:
Z=—C(O)—R
9
or Z=—CH(OH)—R
9
(&agr;- or &bgr;-hydroxy), whereby R
9
is a straight-chain or branched-chain, saturated or unsaturated hydrocarbon radical with up to 12 carbon atoms or else R
9
can be carbocyclic or heterocyclic or can exhibit such partial structures and can also be perfluorinated.
For R
9
, the following special preferences apply:
R
9
=methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, i-propyl, i-butyl, t-butyl, 1-butenyl, 1-pentenyl, 1-butinyl, 1-pentinyl, phenyl, furanyl, pyridinyl, trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluorobutyl, perfluoropentyl or perfluorohexyl.
Also, for Z, the following preference applies:
with R
12
=C
1
-C
10
alkyl or alkoxy (straight-chain, branched, saturated, unsaturated, cyclic) or
with R
13
=C
1
-C
10
alkyl (straight-chain, branched, saturated, unsaturated, cyclic), whereby R
13
can also have substituents (keto groups, hydroxy groups, carboxylic acid esters, carboxylic acid amides, halogens).
Especially preferred according to this invention are the following compounds:
(5Z,7E,22E)-(1S,3R,24R)-25-(1-Oxopentyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxopentyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-acetyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-acetyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(1-oxopropyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxopropyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(1-oxobutyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxobutyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(1-oxohexyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxohexyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(1-oxoheptyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxoheptyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(1-oxooctyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxooctyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(1-oxononyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxononyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-benzoyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-benzoyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(2-furanylcarbonyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(2-furanylcarbonyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(2,2-dimethyl-1-oxopropyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(2,2-dimethyl-1-oxopropyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(2-pyridinylcarbonyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(2-pyridinylcarbonyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
[5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(1-oxo-2-hexenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
[5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(1-oxo-2-hexenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3, -24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(1-oxo-2-hexinyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(1-oxo-2-hexinyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24R)-25-(cyclopropylcarbonyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
(5Z,7E,22E)-(1S,3R,24S)-25-(cyclopropylcarbonyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
[5Z,7E,22E,25(E)]-(1S,3R,24R)-25-(3-ethoxy-3-oxo-1-propenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
[5Z,7E,22E,25(E)]-(1S,3R,24S)-25-(3-ethoxy-3-oxo-1-propenyl)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1,3,24-triol
[5Z,7E,22E,25(E)]-(1S,3R,24R)-25-[3-(1,1-dimethylethoxy)-3-oxo-1-propenyl]-26,27-
Haberey Martin
Kirsch Gerald
Menrad Andreas
Neef Günter
Schwarz Katica
Pryor Alton
Schering Aktiengesellschaft
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