Benzocycloheptenes, process for their production,...

Details Benzocycloheptenes, process for their production,... Benzocycloheptenes, process for their production,...

1999-07-19

2002-12-17

Rotman, Alan L. (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Sulfur, selenium or tellurium compound

C514S708000, C514S759000, C514S741000, C564S139000, C568S027000, C568S028000, C568S030000

Reexamination Certificate

active

06495607

ABSTRACT:

This invention relates to benzocycloheptenes of general formula I
in which
R
1
and R
2
, independently of one another, stand for a hydrogen atom, a hydroxy group, an optionally substituted C
1
-C
10
alkoxy group, an optionally substituted C
1
-C
10
alkanoyloxy group or an optionally substituted C
7
-C
15
aroyloxy group, and
Y stands for a side chain —A—B—Z,
whereby
A means a direct bond or an oxygen atom,
B means a straight-chain or branched-chain, optionally substituted alkylene, alkenylene or alkinylene group with up to 10 carbon atoms,
Z means a group —D—SO
x
—E—G, an amino group —NR
7
R
8
or a substituent G, in which
D means a direct bond or a group —NR
3
(R
4
—), R
3
means a straight-chain or branched-chain alkyl, alkenyl or alkinyl group with up to 10 carbon atoms and R
4
means a straight-chain or branched-chain, optionally substituted alkylene, alkenylene or alkinylene group with up to 10 carbon atoms, whereby the nitrogen atom also can be incorporated in a 4- to 7-membered ring system,
the nitrogen atom can also be incorporated into a 4- to 7-membered ring system,
x means 0, 1 or 2,
E means a straight-chain or branched-chain, optionally substituted alkylene, alkenylene or alkinylene group with up to 10 carbon atoms,
G means a partially or completely fluorinated, straight-chain or branched-chain alkyl group with up to 5 carbon atoms, an optionally substituted aryl or heteroaryl radical, a carbamoyl radical —C(O)—NR
5
R
6
with R
5
and R
6
in the meaning of R
7
and R
8
, a halogen atom or a hydrogen atom,
R
7
and R
8
, independently of one another, mean a hydrogen atom, a straight-chain or branched-chain, optionally partially fluorinated alkyl, alkenyl or alkinyl radical with up to 14 carbon atoms, which can be interrupted by one to three heteroatoms —O— and —S— and groupings —NR
9
—, in which R
9
means a hydrogen atom or a C
1
-C
3
alkyl radical, an aryl or heteroaryl radical that is optionally substituted in one or two places, a C
3
-C
10
cycloalkyl radical that is optionally substituted in one or two places, a C
4
-C
15
cycloalkylalkyl radical that is optionally substituted in one or two places, a C
7
-C
20
aralkyl radical that is optionally substituted in one or two places, a heteroaryl-C
1
-C
8
alkyl radical that is optionally substituted in one or two places or an optionally substituted aminoalkyl radical, a biphenylene radical or a radical of formula —C(O)R
10
, in which R
10
can have the meanings that are indicated above for R
7
or R
8
,
R
7
and R
8
with the nitrogen atom, to which they are bonded, form a saturated or unsaturated heterocycle with 5 or 6 chain links, which optionally contains one or two additional heteroatoms, selected from nitrogen, oxygen and sulfur, and optionally is substituted, and in —A—B—Z, if A stands for an oxygen atom and Z stands for G, G cannot be a hydrogen atom or a halogen atom, or if A stands for an oxygen atom and Z stands for an amino group —NR
7
R
8
, in which R
7
and R
8
in each case mean a methyl group or together with the nitrogen atom form a pyrrolidine ring, B has at least 3 carbon atoms.
As a C
1
-C
10
alkoxy group R
1
or R
2
, for example, a methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, pentoxy, isopentoxy, neopentoxy, heptyloxy, hexyloxy or decyloxy group is suitable.
The alkanoyl groups that are contained in R
1
and R
2
of general formula I are to contain 1 to 20 carbon atoms in each case, whereby formyl, acetyl, propionyl and isopropionyl groups are preferred.
Aroyl radicals R
1
or R
2
are primarily benzoates and benzoates that are substituted in the phenyl radical; they can also be the other aroyl and heteroaroyl radicals that are derived from the aryl radicals that are explained in more detail below.
For B, primarily a straight-chain alkylene group with 1 to 6 carbon atoms is suitable.
As alkyl groups R
3
, R
7
and R
8
, straight-chain or branched-chain alkyl groups with up to 10 carbon atoms can be considered, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, isopentyl, neopentyl, heptyl, hexyl, decyl.
The latter can have up to 3 unsaturations (double bonds and/or triple bonds).
Alkyl groups R
3
, R
7
and R
8
can be partially or completely fluorinated or substituted.
As a partially or completely fluorinated straight-chain or branched C
1
-C
10
alkyl group, for example, the trifluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, 4,4,4-trifluorobutyl group, 3,3,4,4,4-pentafluorobutyl group, 4,4,5,5,5-pentafluoropentyl group or nonafluorobutyl group can be mentioned.
The latter can also have up to 3 unsaturations (double bonds and/or triple bonds).
The C
1
-C
3
alkyl radical that stands for R
9
is a methyl, ethyl, propyl or isopropyl radical; the methyl radical is preferred.
For aryl radical R
3
or R
4
and G and the aryl radical within arylalkyl radical R
3
or R
4
, the following radicals that are optionally substituted in one or more places can stand for:
a monocyclic, carbocyclic radical, for example the phenyl radical;
a monocyclic, heterocyclic radical, for example the thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, oxazolyl, furazanyl, pyrrolinyl, imidazolinyl, pyrazolinyl, thiazolinyl, triazolyl, tetrazolyl radical, specifically all possible isomers relative to the positions of the heteroatoms as well as the interface sites to the sulfur atom in the side chain;
a condensed carbocyclic radical, for example the naphthyl or phenanthrenyl radical;
a condensed radical, which consists of carbocyclic and heterocyclic radicals, for example the benzofuranyl, benzothienyl, benzimidazolyl, benzothiazolyl, naphtho[2,3-b]thienyl, thianthrenyl, isobenzofuranyl, chromenyl, xanthenyl, phenoxathiinyl, indolizinyl, isoindolyl, 3H-indolyl, indolyl, indazolyl, purinyl, quinolizinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, carbazolyl, &bgr;-carbolinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, indolinyl, isoindolinyl, imidazopyridyl, imidazopyrimidinyl or a condensed polyheterocyclic system, for example furo[2,3-b]pyrrole or thieno[2,3-b]furan.
As substituents to radicals B, G, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
and R
10
as well as R
3
together with R
4
, the substituents below are suitable, whereby the radicals can be substituted in one or more places, identically or differently, with these substituents:
Halogen atoms: fluorine, chlorine, bromine, iodine;
amino-, mono(C
1-8
alkyl)- or di(C
1-8
alkyl)amino, whereby both alkyl groups are identical or different, especially methylamino or ethylamino, dimethylamino, diethylamino or methylethylamino; di(aralkyl)amino, whereby both aralkyl groups are identical or different;
hydroxyl groups;
free, esterified carboxyl groups or carboxyl groups that are present in the form of a salt: esterified with a carboxycarbonyl group, for example methoxycarbonyl or ethoxycarbonyl; as salt, for example in the form of sodium or potassium salt;
alkyl groups with 1 to 8 carbon atoms, such as, for example, the methyl, ethyl, n- or iso-propyl, n-, iso- or tert-butyl group, optionally substituted with one or more halogen atoms, for example with fluorine, such as the trifluoromethyl or pentafluoroethyl group;
oxo, azido, cyano, nitro or formyl groups;
acyl groups such as acetyl, propionyl, butyryl, benzoyl;
acyloxy groups such as acetoxy, radicals of formula —O—CO—(CH
2
)
n
—COOH with n=1 to 5;
C
1
-C
4
alkoxy groups, such as, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy;
alkylthio groups, for example methylthio, ethylthio, propylthio, isopropylthio, butylthio, all optionally fluorinated,
carbamoyl groups;
alkenyl groups, for example vinyl, propenyl;
alkinyl groups, for example ethinyl, propinyl;
C
6
-C
12
aryl groups, such as phenyl, furyl, thienyl, which in turn can be substituted in one to three places.
As a cycloalkyl group for substituents R
7
and R
8
, substituted and unsubstituted radicals wit

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