Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-09-25
2004-06-08
McKane, Joseph K. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S378000, C514S407000, C546S275700, C548S236000, C548S360100
Reexamination Certificate
active
06747046
ABSTRACT:
The invention relates to substituted N-(1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl) derivatives, their production and use as pharmaceutical agents for treating various diseases.
Known from DE 198 54 081 A1 or WO 00/31066 are substituted N-pyrazolyl-phenoxynicotinic acid-(thio)amides that are used as herbicides. These compounds clearly differ structurally from the compounds according to the invention, however.
From WO 01/12189, 3(5)-amino-pyrazole derivatives and their use as pharmaceutical agents, especially for treating cancer and cell-proliferative diseases, are known. These compounds also differ from the compounds according to the invention by their structure, especially on the pyrazole ring.
There is still a great need for effective pharmaceutical agents for treating cancer and other cell-proliferative diseases.
It has now been found that compounds of general formula I
in which
R
1
stands for linear or branched C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkinyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio or C
3
-C
12
-cycloalkyl, C
3
-C
12
-cycloalkenyl, C
3
-C
12
-heterocycloalkyl, C
3
-C
12
-heterocycloalkenyl, aryl or heteroaryl, which optionally can be substituted in one or more places in the same way or differently,
R
2
and R
3
are the same or different and stand for hydrogen, linear or branched C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkinyl or C
1
-C
6
-alkoxy, which optionally can be substituted in one or more places in the same way or differently,
R
4
and R
5
are the same or different and stand for hydrogen, halogen, linear or branched C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkinyl or C
1
-C
6
-alkoxy, which optionally can be substituted in one or more places in the same way or differently, or together stand for a carbonyl group, or together form a cyclic five- or six-ring-acetal with O,O; N,O; O,S; or S,S, which optionally can be substituted with C
1
-C
6
-alkyl, or
R
2
and R
4
together form a C
3
-C
12
-cycloalkyl ring or a C
3
-C
12
-cycloalkenyl ring, which optionally can be substituted in one or more places in the same way or differently,
R
6
and R
7
are the same or different and stand for hydrogen, linear or branched C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkinyl, which optionally can be substituted in one or more places in the same way or differently, or together form a C
3
-C
12
-cycloalkyl ring or a C
3
-C
12
-cycloalkenyl ring, which optionally can be substituted in one or more places in the same way or differently, or
R
5
and R
6
optionally together form a double bond, or
R
5
and R
6
together form a C
3
-C
12
-cycloalkyl ring or a C
3
-C
12
-cycloalkenyl ring, which optionally can be substituted in one or more places in the same way or differently,
T stands for —CH
2
—, —O—, —CH
2
═CH
2
—, —CH≡CH—, —CH
2
—O—CH
2
—, —CH
2
—O—, —O—CH
2
— or ═CO, and
n stands for 0-6, as well as tautomers, isomers and salts thereof.
Alkyl is defined in each case as a straight-chain or branched alkyl radical, such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl or hexyl.
Alkoxy is defined in each case as a straight-chain or branched alkoxy radical, such as, for example, methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, isopentyloxy or hexyloxy.
Alkythio is defined in each case as a straight-chain or branched alkylthio radical, such as, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, isopentylthio or hexylthio.
Cycloalkyls are defined as monocyclic alkyl rings, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl, but also bicyclic rings or tricyclic rings, such as, for example, norbornyl, adamantanyl, etc.
Cycloalkenyl is defined in each case as cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclononenyl or cyclodecenyl, whereby the linkage can be carried out both to the double bond and to the single bonds.
Halogen is defined in each case as fluorine, chlorine, bromine or iodine.
Alkenyl is defined in each case as a straight-chain or branched alkenyl radical that contains 2-6, preferably 2-4, C atoms. For example, the following radicals can be mentioned: vinyl, propen-1-yl, propen-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, 2-methyl-prop-2-en-1-yl, 2-methyl-prop-1-en-1-yl, but-1-en-3-yl, but-3-en-1-yl, and allyl.
Alkinyl is defined in each case as a straight-chain or branched alkinyl radical that contains 2-6, preferably 2-4, C atoms. For example, the following radicals can be mentioned: acetylene, propin-1-yl, propin-3-yl, but-1-in-1-yl, but-1-in-4-yl, but-2-in-1-yl, but-1-in-3-yl, etc.
The aryl radical in each case comprises 3-12 carbon atoms, and can be benzocondensed in each case.
For example, there can be mentioned: cyclopropenyl, cyclopentadienyl, phenyl, tropyl, cyclooctadienyl, indenyl, naphthyl, azulenyl, biphenyl, fluorenyl, anthracenyl, etc.
The heteroaryl radical in each case comprises 3-16 ring atoms, and instead of carbon, the radical can contain one or more heteroatoms that are the same or different, such as oxygen, nitrogen or sulfur in the ring, and can be monocyclic, bicyclic or tricyclic, and in addition in each case can be benzocondensed.
For example, there can be mentioned:
Thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, etc. and benzo derivatives thereof, such as, e.g., benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, indazolyl, indolyl, isoindolyl, etc.; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, etc. and benzo derivatives thereof, such as, e.g., quinolyl, isoquinolyl, etc.; or oxepinyl, azocinyl, indolizinyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, purinyl, etc. and benzo derivatives thereof; or quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, etc.
Heterocycloalkyl stands for an alkyl ring that comprises 3-12 carbon atoms and that instead of carbon contains one or more heteoratoms that are the same or different, such as, e.g., oxygen, sulfur or nitrogen.
As heterocycloalkyls, there can be mentioned, e.g.: oxiranyl, oxethanyl, aziridinyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, dioxolanyl, imidazolidinyl, pyrazolidinyl, dioxanyl, piperidinyl, morpholinyl, dithianyl, thiomorpholinyl, piperazinyl, trithianyl, quinuclidinyl, etc.
Heterocycloalkenyl stands for an alkyl ring that comprises 3-12 carbon atoms and that instead of carbon contains one or more heteroatoms that are the same or different, such as, e.g., oxygen, sulfur or nitrogen, and that is partially saturated.
As heterocycloalkenyls, there can be mentioned, e.g.: pyran, thiine, dihydroazete, etc.
Cyclic acetal stands for a ring, such as, e.g.,
which optionally can be substituted with a C
1
-C
6
-alkyl group.
The aryl radical and the heteroaryl radical can be substituted in each case in one or more places in the same way or differently with hydroxy, halogen, amino, C
1-6
-alkyl, C
1-6
-alkoxy, C
1-6
-alkylthio, halo-C
1-6
-alkyl, halo-C
1-6
-alkoxy, C
1-6
-alkoxycarbonyl, cyano, nitro, C
1-6
-alkylsulfanyl, C
1-6
-alkylsulfinyl, C
1-6
-alkylsulfonyl, or with the group —C(O) C
1-6
-alkyl, —NHC
1-6
-alkyl, —N-di-C
1-6
-alkyl, —CONH
2
, —CONHC
1-6
-alkyl or —CON-di-C
1-6
-alkyl, or can be substituted with another aryl or heteroaryl radical, which optionally itself can be substituted in one or more places in the same way or differently with hydroxy, halogen, amino, C
1-6
-alkyl, C
1-6
-alkoxy, C
1-6
-alkylthio, halo-C
1-6
-alkyl, halo-C
1-6
-alkoxy, C
1-6
-alkoxycarbonyl, cyano, nitro, C
1-6
-alkylcarbonyl, C
1-6
-alkylsulfanyl, C
1-6
-alkylsulfinyl, C
1-6
-alkylsulfonyl, or with the group —C(O)C
1-6
-alkyl, —NHC
1-6
-alkyl, —N-di-C
1-6
-alkyl, —CONH
2
, —CONHC
1-6
-alkyl or —CON-di-C
1-6
Ernst Alexander
Haberey Martin
Hoffmann Jens
Kroll Jörg
Krüger Martin
McKane Joseph K.
Millen White Zelano & Branigan P.C.
Schering Aktiengesellschaft
Small Andrea D
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