Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-02-19
2001-01-30
Kifle, Bruck (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S280000
Reexamination Certificate
active
06180636
ABSTRACT:
The invention relates to 7H-pyrrolo[2,3-d]pyrimidine derivatives and to processes and novel intermediates for their preparation, to pharmaceutical formulations comprising such derivatives and to the use of these derivatives as medicaments.
The invention relates to 7H-pyrrolo[2,3-d]pyrimidine derivatives of the formula I
in which n is 0 to 3,
q is 0 or 1,
R is halogen, lower alkyl, hydroxymethyl, aminomethyl, hydroxyl, lower alkanoyloxy, lower alkoxy, carboxyl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl, N,N-di-lower alkylcarbamoyl, cyano, amino, lower alkanoylamino, lower alkylamino, N,N-di-lower alkylamino or trifluoromethyl, it being possible, if two or more radicals R are present in the molecule, for these to be identical to or different from one another,
one of the radicals R
1
and R
2
is hydrogen or lower alkyl,
and the other of the radicals R
1
and R
2
is
a) a radical of the formula II
in which u is 1 to 3 and
at least one radical R
4
is amidino, guanidino, ureido, N
3
-lower alkylureido, N
3
,N
3
-di-lower alkylureido, N
3
-phenylureido, N
3
,N
3
-diphenylureido, thiocarbamoyl, thioureido, N
3
-lower alkylthioureido, N
3
,N
3
-di-lower alkylthioureido, lower alkoxycarbonylamino, benzyloxycarbonylamino, morpholine-4-carbonyl, piperazine-1-carbonyl, 4-lower alkylpiperazine-1-carbonyl, lower alkylsulfonylamino, benzenesulfonylamino, toluenesulfonylamino, thiophene-2-carbonylamino, furan-2-carbonylamino, benzylamino, hydroxymethyl, aminomethyl or a radical of the formula —N═C(R
5
)—R
6
, in which R
5
is hydrogen or lower alkyl and R
6
is di-lower alkylamino, piperidino, 4-lower alkylpiperazino or morpholino, and the other radical(s) R
4
is (are) halogen, lower alkyl, hydroxyl, lower alkanoyloxy, lower alkoxy, carboxyl, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl, N,N-di-lower alkylcarbamoyl, cyano, amino, lower alkanoylamino, lower alkylamino, N,N-di-lower alkylamino or trifluoromethyl, it being possible, if two or more radicals R
4
are present in the molecule, for these to be identical to or different from one another, or is
b) a radical of the formula III
in which R
7
is lower alkoxy or benzyloxy and R
8
is hydroxyl or benzyloxy, or is
c) amino-lower alkyl, in which the amino group is substituted by one or two hydroxy-lower alkyl, amino-lower alkyl, carboxy-lower alkyl, lower alkoxycarbonyl-lower alkyl, benzyloxycarbonyl-lower alkyl or benzyl radicals, which in the phenyl moiety are unsubstituted or substituted by halogen, lower alkyl, hydroxymethyl, aminomethyl, hydroxyl, lower alkanoyloxy, lower alkoxy, carboxyl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl, N,N-di-lower alkylcarbamoyl, cyano, amino, lower alkanoylamino, lower alkylamino, N,N-di-lower alkylamino or trifluoromethyl, or is
d) piperidine-1-carbonyl, piperazine-1-carbonyl, 4-lower alkylpiperazine-1-carbonyl, morpholine-4-carbonyl, thiocarbamoyl, a heterocyclic radical bonded via a ring carbon atom and having five ring members and 1-4 ring heteroatoms, selected from oxygen, nitrogen and sulfur, or is
e) 4-lower alkylpiperazinomethyl or a lower alkyl radical which is substituted by a heterocyclic radical other than piperazinyl and having five or six ring members and 1-4 ring heteroatoms, selected from oxygen, nitrogen and sulfur, or is
f) a radical of the formula —CH═N—OR
9
in which R
9
is hydrogen or lower alkyl, or
g) if q is 1, additionally to the definitions given above in the sections a) to f) can also be phenyl which is substituted by halogen, lower alkyl, trifluoromethyl or lower alkoxy, and R
3
is hydrogen, lower alkyl, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl or N,N-di-lower alkylcarbamoyl,
and their salts.
The prefix “lower” used hereinbefore and hereinafter denotes a radical having up to and including a maximum of 7, especially up to and including a maximum of 4, and in particular having 1 or 2, carbon atoms.
Preferably, n is 0 or especially 1. When there is only one substituent R, this substituent is preferably in the 3-position on the phenyl ring. When two substituents R are present, these substituents are preferably in the 3- and 4-positions.
Halogen R is bromine, iodine or preferably fluorine or chlorine. When n is 1, R is preferably chlorine.
Lower alkyl is, for example, methyl.
Lower alkanoyloxy is, for example, acetoxy.
Lower alkoxy is, for example, methoxy.
Lower alkanoyl is, for example, acetyl.
Lower alkoxycarbonyl is, for example, methoxycarbonyl.
N-Lower alkylcarbamoyl is, for example, N-methylcarbamoyl, N-(n-butyl)carbamoyl or N-(3-methylbut-1-yl)carbamoyl. N,N-Di-lower alkylcarbamoyl is, for example, N,N-di-methylcarbamoyl.
Lower alkanoylamino is, for example, acetylamino.
Lower alkylamino is, for example, methylamino.
N,N-Di-lower alkylamino is, for example, dimethylamino.
Lower alkoxycarbonylmethoxy is, for example, methoxycarbonylmethoxy.
The radical R
1
is preferably hydrogen.
The symbol u is preferably 1. In this case, the radical R
4
is preferably in the 3- or 4-position of the phenyl ring.
Amidino is a radical of the formula —C(═NH)—NH
2
.
Guanidino is a radical of the formula —NH—C(═NH)—NH
2
.
Ureido is a radical of the formula —NH—C(═O)—NH
2
.
N
3
-Lower alkyl ureido is a radical of the formula —NH—C(═O)—NH-lower alkyl, preferably N
3
-ethylureido.
N
3
, N
3
-Di-lower alkylureido is a radical of the formula —NH—C(═O)—N(lower alkyl)
2
.
N
3
-Phenylureido is a radical of the formula —NH—C(═O)—NH-phenyl.
N
3
, N
3
-Diphenylureido is a radical of the formula —NH—C(═O)—N(phenyl)
2
.
Thioureido is a radical of the formula —NH—C(═S)—NH
2
.
N
3
-Lower alkylthioureido is a radical of the formula —NH—C(═S)—NH-lower alkyl, preferably N
3
-methylthioureido.
N
3
,N
3
-Di-lower alkylthioureido is a radical of the formula —NH—C(═S)—N(lower alkyl)
2
.
Lower alkoxycarbonylamino is, for example, methoxycarbonylamino, ethoxycarbonylamino, isopropyloxycarbonylamino or 2-methylpropyloxycarbonylamino.
Morpholine-4-carbonyl is also called morpholinocarbonyl.
4-Lower alkylpiperazine-1-carbonyl is preferably 4-methylpiperazine-1-carbonyl.
Lower alkylsulfonylamino is preferably methylsulfonylamino, ethylsulfonylamino or isopropylsulfonylamino.
The radical of the formula —N═C(R
5
)—R
6
, in which R
5
is hydrogen and R
6
is di-lower alkylamino, is called di-lower alkylaminomethylenamino. Corresponding radicals in which R
6
is piperidino, 4-lower alkylpiperazino or morpholino are called R
6
-methylenamino radicals, in which R
6
is defined as above, e.g. as piperidinomethylamino.
R
5
is preferably hydrogen.
Di-lower alkylamino R
6
is preferably dimethylamino or diethylamino.
4-Lower alkylpiperazino is 4-lower alkylpiperazin-1-yl, preferably 4-methylpiperazin-1-yl.
Morpholino is 4-morphotinyl.
Lower alkoxy R
7
is preferably methoxy.
Amino-lower alkyl R
1
or R
2
in which the amino group is substituted by one or two hydroxy-lower alkyl, amino-lower alkyl, carboxy-lower alkyl, lower alkoxycarbonyl-lower alkyl, benzyloxycarbonyl-lower alkyl or benzyl radicals which in the phenyl moiety are unsubstituted or substituted by halogen, lower alkyl, hydroxymethyl, aminomethyl, hydroxyl, lower alkanoyloxy, lower alkoxy, carboxyl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, carbamoyl, N-lower alkylcarbamoyl, N,N-di-lower alkylcarbamoyl, cyano, amino, lower alkanoylamino, lower alkylamino, N,N-di-lower alkylamino or trifluoromethyl, is preferably appropriately substituted aminomethyl.
Amino-lower alkyl R
1
or R
2
in which the amino group is substituted by one or two hydroxy-lower alkyl radicals is preferably, for example, a radical of the formula —CH
2
—NH(CH
2
—CH
2
)
2
.
Amino-lower alkyl R
1
or R
2
in which the amino group is substituted by one or two benzyl radicals which in the phenyl moiety are unsubstituted or substituted by halogen, lower alkyl, hydroxymethyl, aminomethyl, hydroxyl, lower alkanoyloxy, lower alkoxy, carboxyl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, carbamoyl,
Bold Guido
Frei Jorg
Lang Marc
Traxler Peter
Borovian Joseph J.
Kifle Bruck
Novartis AG
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