We claim:
1. A method for plasma etching a silicon nitride layer comprising:
(a) forming a plasma from a gaseous mixture consisting essentially of an etchant gas in a sputtering gas; and
(b) etching a silicon nitride layer at more than two microns per minute
2. A method according to claim 1 wherein the thickness of said silicon nitride layer is at least five microns before etching.
3. A method according to claim 1 wherein the thickness of said silicon nitride layer is between about 10 microns to about 50 microns before etching.
4. A method according to claim 1 wherein said plasma is formed by exposing said gaseous mixture to energy provided by separately controllable power sources.
5. The method according to claim for wherein at least one of said power sources is inductively coupled to said plasma.
6. A method according to claim 1 wherein said etchant gas is fluorine containing compound.
7. A method according to claim 1 wherein said etchant gas is SF6.
8. A method according to claim 1 wherein said sputtering gas is an inert gas.
9. A method according to claim 8 wherein said inert gas is selected from the group consisting of: Ar, N2, He, Kr, Xe and Ne.
10. A method for plasma etching a material comprising:
(a) forming a first plasma from a first gaseous mixture consisting essentially of an etchant gas and a sputtering gas;
(b) etching a first portion of said material with said first plasma at an etch rate of about two microns per minute;
(c) forming a second plasma from a second gaseous mixture different from said first gaseous mixture, said second gaseous mixture consisting essentially of an etchant gas and a sputtering gas;
(d) etching a second portion of said material with said second plasma at an etch rate less than said first plasma etch rate.
11. A method according to claim 10 wherein said etchant gas makes up most of said first and said second gaseous mixtures.
12. A method according to claim 10 wherein the flow rate of said etchant gas in said first gaseous mixture is greater than the flow rate of said etchant gas in said second mixture.
13. A method according to claim 12 wherein the flow rate of the etchant gas in said second gaseous mixture is about 66 percent of said etchant flow rate in said first gaseous mixture.
14. A method according to claim 12 wherein the flow rate of the etchant gas in said second gaseous mixture is about 78 percent of said etchant flow rate in said first gaseous mixture.
15. A method according to claim 12 wherein the flow rate of the sputtering gas in said second gaseous mixture is less than the flow rate of the sputtering gas in said first gaseous mixture.
16. A method according to claim 15 wherein the flow rate of said sputtering gas in said second gaseous mixture is about 60 percent of the flow rate of the sputtering gas in said first gaseous mixture.
17. A method according to claim 15 wherein the flow rate of said sputtering gas in said second gaseous mixture is about 65 percent of the flow rate of the sputtering gas in said first gaseous mixture.
18. A method according to claim 12 wherein the percentage of sputtering gas in said second gaseous mixture is greater than the percentage of sputtering gas in said first gaseous mixture.
19. A method according to claim 10 wherein said etching of a second portion is conducted at a second pressure lower than a first pressure used for etching said first portion.
20. A method according to claim 19 wherein said first pressure in said second pressure are less than 50 mT.
21. A method according claim 19 wherein said second pressure is about one-half of said first pressure.
22. A method according to claim 19 wherein said second pressure is about one quarter of said first pressure.
23. A method according claim 10 wherein said first portion is substantially all of said material.
24. A method according claim 10 wherein said first portion is greater than said second portion.
25. A method for plasma etching a material comprising:
(a) forming a first plasma from a first gaseous mixture consisting essentially of an etchant gas and a sputtering gas, a first energy provided from a first power source added first power level and a second energy provided from a second power source of a second power level;
(b) etching a first portion of said material with said first plasma at an etch rate of about two microns per minute;
(c) forming a second plasma from a second gaseous mixture different from said first gaseous mixture, said second gaseous mixture consisting essentially of an etchant gas and a sputtering gas, said first energy provided from said first power source at a third power level and said second energy provided from said second power source of a third power level;
(d) etching a second portion of said material with said second plasma at an etch rate less than said first plasma etch rate.
26. A method according to claim 25 wherein the total power provided by said first power level and said second power level is greater than the total power provided by said third power level and said fourth power level.
27. A method according to claim 25 wherein the total power provided by said first power level and said second power level is about the same as a total power provided by said third power level and said forth power level.
28. A method according to claim 25 wherein said first and said third power levels are the same and said fourth power level is less than said second power level.
29. The method of claim 28 wherein said fourth power level is about 15 percent of said second power level.
30. The method according claim 25 wherein said first power source is inductively coupled to said first plasma and said second plasma.
31. The method according to claim 25 wherein the third power level is a greater percentage of the total power provided by said third and said fourth power levels than said first power level is as a percentage of the total power provided by said first power level and said second power level.
32. The method according to claim 31 wherein said third power level is about 98 percent of the total power provided by said first power source and said third power level and said second power source and said fourth power level.
33. A method according to claim 25 wherein said first power level is about 90 percent of the total power provided by said first power level and said second power level.
34. The method according to claim 25 wherein said third power level is about 98 percent of total power provided by said third power level and said fourth power level.
35. A computer readable storage medium having program code embodied therein, said program code for controlling a processing system, wherein said processing system includes a chamber, two power supplies coupled to said chamber, and a gas supply wherein said program code controls the processing system to etch a layer of material formed on a workpiece in accordance with the following:
(a) flowing a gaseous composition consisting of an etchant gas and a sputtering gas from said gas supply into said chamber;
(b) providing energy from each of said power supplies to said chamber to form a plasma from said gaseous composition; and
(c) etching substantially all of the layer of material at a rate of at least about two microns per minute.
36. An apparatus for plasma etching a workpiece in a processing chamber, comprising:
a gas panel coupled to said processing chamber;
an antenna proximate to said processing chamber
a first power supply coupled to said antenna;
a second power supply coupled to said chamber; and
a controller, coupled to said first and said second power supplies and said gas panel, said controller containing a computer readable storage medium having program code embodied therein, said program code for controlling the apparatus in accordance with the following:
(a) loading into the processing chamber a workpiece having a layer of material formed thereon;
(b) flowing from the gas panel to the processing chamber a gaseous composition consisting of an etchant gas and a sputtering gas;
(c) controlling said first power supply to provide energy to said antenna and said second power supply to provide energy to set chamber thereby forming a plasma in set chamber from said gaseous composition; and
(d) controlling said plasma to etch substantially all of said layer of material at more than two microns per minute.
The claims below are in addition to those above.
All refrences to claim(s) which appear below refer to the numbering after this setence.
1. A compound of formula 1
wherein:
X is O, S, SO, or SO2;
R1 is H, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C6-10-aryl, C6-10-aryl-C1-6-alkylene, or C5-10-heteroaryl-C1-6-alkylene,
R2 is H or an optionally mono- or polysubstituted group selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, an optionally mono- or poly-bridged mono- or bicyclic C3-10-cycloalkyl, C6-10-aryl, an aromatic or non-aromatic, heterocyclic C3-10 ring, a bicyclic ring, and a C6-10-aryl fused to a C3-10 heterocycle, or
NR1R2 together is a heterocyclic ring optionally substituted by one or more groups selected from C1-4-alkyl, C2-6-alkenyl, C2-6-alkynyl, straight-chain or branched C1-6-alkanol, and oxo;
R3 is a mono- or polysubstituted group selected from a heterocyclic C6-10 ring, C3-7-cycloalkyl, C6-10-aryl-C1-6-alkylene, C5-10-heteroaryl-C1-6-alkylene, a fused, bicyclic ring optionally containing 1 to 4 heteroatoms independently selected from N, O, and S, or
R3 is optionally substituted phenyl, or
R3 is COR3.7, COCH2R3.8, CONHR3.8, or SO2R3.8, wherein:
R3.7 is H, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, or C6-10-aryl;
R3.8 is C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C3-7-cycloalkyl, or a group selected from C6-10-aryl, a heterocyclic C3-10 ring, and a bicyclic ring optionally substituted by one or more groups selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, halogen, NR3.8.1R3.8.2, C6-10-aryl, and a heterocyclic C3-10 ring, wherein:
R3.8.1 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl, and
R3.8.2 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl;
R4 is H, C1-4-alkyl, C2-4-alkenyl, C2-4-alkynyl, or oxo;
R5 is H, C2-4-alkenyl, or C2-4-alkynyl;
R6 is H, C2-4-alkenyl, or C2-4-alkynyl;
R7 is H, C1-4-alkyl, C2-4-alkenyl, C2-4-alkynyl, C6-10-aryl, or OH; and
R8 is H, C2-4-alkenyl, C2-4-alkynyl, C6-10-aryl, or OH; or
R7 and R8 together form oxo;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
2. The compound of formula 1 according to claim 1, wherein:
X is O, S, SO, or SO2;
R1 is H, C1-6-alkyl, C6-10-aryl, C6-10-aryl-C1-6-alkylene, or C5-10-heteroaryl-C1-6-alkylene,
R2 is H or C1-6-alkyl optionally substituted by one or more groups selected from C1-6-haloalkyl, CN, OR2.1, NR2.1R2.2, COOR2.1, CONR2.1R2.2, C3-7-cycloalkyl optionally substituted by C1-4-alkyl or oxo, an aromatic or non-aromatic heterocycle optionally substituted by oxo, OH, or halogen, C6-10-aryl optionally substituted by C1-4-alkyl or oxo, and C6-10-aryl fused to a C5-6 heterocycle, wherein this fused ring system is optionally substituted by C1-4-alkyl or oxo, wherein:
R2.1 is H or C1-6-alkyl optionally substituted by a C3-7-cycloalkyl, C3-10 heterocycle, or C6-10-aryl, each optionally substituted and
R2.2 is H or C1-6-alkyl; or
R2 is an optionally mono- or poly-bridged C3-10-cycloalkyl or a C3-10-cycloalkyl, each optionally fused to a C6-10-aryl ring optionally substituted by one or more groups selected from C1-6-alkyl, OH, CH2OR2.3, COOR2.3, COR2.3, CONR2.3R2.4, O\u2014C1-6-alkyl, O\u2014C7-11-aralkyl, NR2.3R2.4, and NHCOR2.5, wherein:
R2.3 is H or a heterocycle or a C1-6-alkyl, optionally substituted by a group selected from C3-7-cycloalkyl, C3-10 heterocycle, and C6-10-aryl, wherein this group is optionally substituted by one or more groups selected from C1-6-alkyl, halogen, OH, and O\u2014C1-6-alkyl,
R2.4 is H or C1-6-alkyl;
R2.5 is selected from the group consisting of C3-7-cycloalkyl, a heterocyclic C3-10 ring, and C1-6-alkyl optionally substituted by OH; or
R2 is a group of formula 1a
\u2003wherein:
Y is C1-6-alkylene optionally substituted by one or two R2.7, wherein R2.7 are independently C1-6-alkyl, COOH, CONH2, OR2.1, or COOR2.1, or R2.7 together with one or two carbon atoms of Y forms a carbocyclic ring with 3 carbon atoms, or
R2 is C6-10-aryl optionally independently substituted by one or more groups selected from C1-6-alkyl, C1-6-haloalkyl, C2-6-alkenyl, C2-6-alkynyl, CN, halogen, OR2.8, COOR2.8, COR2.10, NHCOMe, CONR2.3R2.4, a C1-4 alkylene group substituted by NR2.1R2.2, or NR2.1R2.2, or
R2 is C6-10-aryl optionally independently substituted by one or more groups selected from C6-10-aryl-C1-6-alkylene, C5-10-heteroaryl-C1-6-alkylene, C3-7-cycloalkyl, a C3-7-cycloalkyl-C1-4-alkylene, C6-10-aryl, and a heterocyclic C3-10 ring, wherein these groups are each optionally substituted by one or more groups selected from C1-6-alkyl, C1-6-haloalkyl, COOR2.8, CN, halogen, OR2.8, NHCOR2.8, oxo, a C3-10 heterocycle, a C3-7-cycloalkyl-C1-4 alkylene, a C5-10 heterocycle-C1-4-alkylene, and a NR2.1R2.2\u2014C1-4 alkylene, wherein:
R2.8 is H, C1-6-alkyl, C6-10-aryl, or a NR2.1R2.2\u2014C1-4 alkylene group, and
R2.10 is NHR2.10.1 or a heterocyclic C3-10 ring optionally substituted by C1-4-alkyl, wherein R2.10.1 is H, C3-7-cycloalkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-alkyl, or C1-6-alkyl-O\u2014C1-4-alkyl, or
R2 is C6-10-aryl to which an aromatic or non-aromatic C3-10 heterocycle is fused, or
R2 is an aromatic or non-aromatic heterocyclic C3-10 ring optionally substituted by one or more groups selected from halogen, OH, oxo, CN, C1-6-alkyl, C1-6-alkanol, C6-10-aryl-C1-6-alkylene, C5-10-heteroaryl-C1-6-alkylene, COR2.11, C3-7-cycloalkyl-C1-4-alkylene, and C3-10 heterocycle-C1-4-alkylene, wherein R2.11 is a group selected from C3-10 heterocycle-C1-4-alkylene, C3-7-cycloalkyl, and a heterocyclic aromatic or non-aromatic C3-10 ring, optionally substituted by C1-6-alkyl optionally substituted by OH, CH2OH, OMe, NH2, a C3-10 heterocycle, or NHCOO-tBu, or
R2 is C2-6-alkenyl or a bicyclic ring, each optionally substituted by methyl, or
NR1R2 is a heterocyclic ring optionally substituted by one or more groups selected from C1-4-alkyl, OH, and C1-4-alkanol;
R3 is a group selected from a heterocyclic C3-10 ring, a C3-7-cycloalkyl, a bicyclic, fused aromatic or non-aromatic ring system, which optionally contains 1 to 4 heteroatoms selected from S, N, O, or it is C6-10-aryl-C1-6-alkylene, C5-10-heteroaryl-C1-6-alkylene, and CH2-benzo1,3dioxolyl, optionally substituted by one or more groups selected from OH, halogen, C1-6-alkyl, O\u2014C1-6-alkyl, C1-6-haloalkyl, and CO\u2014R3.1, or
R3 is phenyl optionally substituted by one or more groups selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-4-haloalkyl, C1-6-alkylene-NR3.1R3.2, CN, COOR3.1, CONR3.1R3.2, NR3.1R3.2, NHCOR3.1, CF3, OR3.1, halogen, NHCOR3.1, NO2, SO2NR3.1R3.2, and C1-6-alkylene-NHCOR3.1, wherein:
R3.1 is H, C1-6-alkyl; C2-6-alkenyl, or C2-6-alkynyl, optionally bridged, mono- or bicyclic C3-10 heterocycle, or C3-10 heterocycle-C1-4-alkylene group, and
R3.2 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl, or
R3 is a group of formula 1b
\u2003wherein:
R3.3 is a heterocyclic C3-10 ring optionally substituted by one or more groups selected from C1-6-alkyl, oxo, COR3.3.1, COR3.3.2, C1-6-alkylene-R3.3.2, CH2CO-pyrrolidine, and a heterocyclic C3-10 ring, wherein a sulfur atom optionally contained in the heterocyclic ring is optionally in the form of the oxide or dioxide, wherein: R3.3.1 is C1-6-alkyl, and R3.3.2 is NH2, NH(C1-6-alkyl), or N(C1-6-alkyl)2, or
R3.3 is a bicyclic ring or heterocyclic spiro ring, or
R3 is a group of formula 1c
\u2003wherein:
A is a bond or C1-6-alkyl optionally substituted by oxo or NMe2;
R3.4 is H or C1-6-alkyl;
R3.5 is C1-6-alkyl optionally substituted by one or more groups selected from C3-7-cycloalkyl, C6-10-aryl, and a C3-10 heterocycle, while this group is optionally substituted in each case by a group selected from OH, oxo, C1-6-alkyl, O\u2014C1-6-alkyl, and C1-6-haloalkyl, or a group selected from a heterocyclic C3-10 ring and a bicyclic ring, optionally substituted by one or more groups selected independently of one another from oxo, C1-6-alkyl, OH, C6-10-aryl, a heterocyclic C3-10 ring, C1-6-alkylene-R3.5.1, O\u2014C1-6-alkylene-R3.5.1, and NH\u2014C1-6-alkylene-R3.5.1, wherein R3.5.1 is a group selected from C6-10-aryl and a heterocyclic C3-10 ring optionally substituted by C1-6-alkyl; or
R3 is a group of formula Id
\u2003wherein:
D is C2-4-alkynyl or an optionally bridged, bicyclic C3-10-cycloalkyl group, each optionally substituted by one or more groups selected from C1-6-alkyl, halogen, OH, C1-6-haloalkyl, and O\u2014C1-6-alkyl,
R3.6 is pyridinyl, or
R3 is COR3.7, COCH2R3.8, CONHR3.8, SO2R3.8, or a heterocyclic group fused to a C6-10-aryl group, each optionally substituted by methyl, or
R3 is a group of formula 1e
\u2003wherein:
R3.7 is H, C1-6-alkyl, or C6-10-aryl;
R3.8 is a group selected from C1-6-alkyl, C3-7-cycloalkyl, or a group selected from C6-10-aryl, a heterocyclic C3-10 ring, and a bicyclic ring, optionally substituted by one or more groups selected from C1-6-alkyl, halogen, NR3.8.1R3.8.2, C6-10-aryl, and a heterocyclic C3-10 ring, wherein: R3.8.1 is H or C1-6-alkyl, and R3.8.2 is H or C1-6-alkyl;
R4 is H, C1-4-alkyl, or oxo;
R5 is H or C1-4-alkyl;
R6 is H or C1-4-alkyl;
R7 is H, C6-10-aryl, or OH;
R8 is H, C6-10-aryl, or OH; or
R7 and R8 together form oxo;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
3. The compound of formula 1 according to claim 1, wherein:
X is O, S, SO, or SO2;
R1 is H, methyl, ethyl, or propyl;
R2 is H or C1-6-alkyl optionally substituted by one or more groups selected from CF3, CN, OH, NMe2, OMe, COOH, and CONMe2, or
R2 is C1-6-alkyl optionally substituted by one or more groups selected from cyclopropyl, cyclopentyl, cyclohexyl, phenyl, pyrrolidinyl, imidazolidinyl, pyrazolyl, imidazolyl, and pyridinyl, each optionally substituted by methyl or oxo; or
R2 is C3-7-cycloalkyl optionally substituted by a group selected from methyl, OR2.3, CH2OR2.3, COOH, CONR2.3R2.4, CONH-tBu, O-benzyl, NR2.3R2.4, and NHCOR2.5, wherein:
R2.3 is H, methyl, or
R2.4 is H or methyl, and
R2.5 is CH2C(CH3)3, CH2C(CH3)2(CH2OH), cyclopentyl, tetrahydrofuranyl, pyrrolyl, pyrazolyl, imidazolyl, or isoxazolyl; or
R2 is a group of formula 1a
\u2003wherein:
Y is C1-4-alkylene optionally substituted by one or two R2.7, and
R2.7 are each independently C1-4-alkyl, COOH, or CONH2, or R2.7 together with one or two carbon atoms of Y forms a carbocyclic ring with 3 carbon atoms; or
R2 is C6-10-aryl optionally substituted by one or more groups independently selected from methyl, tert-butyl, CN, F, Cl, Br, OH, OMe, OEt, O-phenyl, COOH, COOMe, COR2.10, NHCOMe, and morpholine-substituted C1-4-alkylene, wherein R2.10 is NH2, NHMe, NH-iPr, NH-cyclopropyl, NHCH2CH2OMe, or a heterocyclic, non-aromatic C3-10 ring containing one, two, or three heteroatoms selected from oxygen and nitrogen; or
R2 is C6-10-aryl optionally substituted by phenyl or a heterocyclic C3-10 ring, each optionally substituted by one or more groups selected from methyl, tert-butyl, COOH, COOMe, CN, F, Cl, Br, OH, OMe, OEt, and NHCOMe, and oxo; or
R2 is a heterocyclic non-aromatic C3-10 ring optionally substituted by benzyl or COR2.11, wherein R2.11 is a group selected from cyclopentyl, tetrahydrofuranyl, furan, pyridyl, pyrrolyl, pyrazolyl, or imidazolyl, each optionally substituted by one or two methyl groups or by one or more groups selected from CH2C(CH3)3, C(CH3)2(CH2OH), CH2OMe, C(CH3)2NH2, and C(CH3)2NHCOO-tBu; or
R2 is C2-6-alkenyl, indanyl, 1,2,3,4-tetrahydronaphthalyl, or 8-methyl-8-azabicyclo3.2.1octane; or
NR1R2 is pyrrolidinyl, piperidinyl, piperazinyl, or morpholinyl, each optionally substituted by methyl;
R3 is pyridinyl, pyrimidine, benzyl, or CH2-benzo1,3dioxolyl; or
R3 is phenyl optionally substituted by one, two, or three groups selected from methyl, CH2NH2, CN, COOH, CONH2, CF3, OH, F, Cl, Br, OMe, NHCOMe, NR3.1COR3.2, CONR3.1R3.2, NO2, SONMe2, and CH2NHCOMe, wherein:
R3.1 is H, C1-6-alkyl, or an optionally bridged, mono- or bicyclic C3-10 heterocycle, and
R3.2 is H or C1-6-alkyl; or
R3 is a group of formula 1b
\u2003wherein:
R3.3 is piperidinyl, piperazinyl, or azepanyl, each optionally independently substituted by one or more groups selected from methyl, oxo, COCH3, CONH2, CH2NEt2, CH2CH2NMe2, CH2COpyrrolidine, pyridinyl, isothiazolidinyl-1,1-dioxide, and thiazolidinyl-1,1-dioxide, or
R3.3 is a group of formula
R3 is a group of formula 1c
\u2003wherein:
A is a bond or C1-4-alkyl optionally substituted by oxo or NMe2,
R3.4 is H or methyl, and
R3.5 is pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, cyclohexyl, imidazolyl, pyrazolyl, phenyl, pyridinyl, benzimidazolyl, imidazolidin-2-one, pyrrolidin-2-one, pyrrolidin-3-one, tetrahydrothiophene-1,1-dioxide, or 1-azabicyclo2.2.2octane, each optionally independently substituted by one or more groups selected from methyl, ethyl, OH, phenyl, pyridinyl, pyrazolyl, pyrrolidinyl, (CH2)o\u2014R3.5.1, O\u2014(CH2)o\u2014R3.5.1, and NH\u2014(CH2)o\u2014R3.5.1, wherein: o is 0, 1, or 2, and R3.5.1 is phenyl, pyrrolidinyl, piperidinyl, or imidazolidin-2-one, each optionally substituted by methyl; or
R3 is a group of formula 1d
\u2003wherein:
D is C2-4-alkynyl;
R3.6 is pyridinyl; or
R3 is COR3.7, COCH2R3.8, CONHR3.8, SO2R3.8, or a group of formula 1e
\u2003wherein:
R3.7 is H, methyl, or phenyl, and
R3.8 is isopropyl, cyclopropyl, cyclopentyl, cyclohexyl, pyrrolidinyl, pyrrolidin-2-one, furanyl, azabicyclo2.2.2octanyl, or a group selected from piperidinyl, pyrazolyl, imidazolyl, isoxazolyl, pyridinyl, phenyl, or benzyl, each optionally independently substituted by one or more groups selected from methyl, chlorine, NH2, NMe2, phenyl, and morpholinyl;
R4 is H, methyl, or oxo;
R5 is H or methyl;
R6 is H or methyl;
R7 is H, methyl, or OH;
R8 is H, methyl, or OH;
or R7 and R8 together form oxo;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
4. The compound of formula 1 according to one of claims 1 to 3, wherein R1 is H, or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
5. The compound of formula 1 according to one of claims 1 to 3, wherein X is SO, or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
6. The compound of formula 1 according to one of claims 1 to 3, wherein R5, R6, R7, and R8 are each H, or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
7. The compound of formula 1 according to claims 1 to 3, wherein R4 is H, or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
8. The compound of formula 1 according to claim 1, wherein:
R2 is C6-10-aryl optionally independently substituted by one or more groups selected from C1-6-alkyl, C1-4-haloalkyl, C2-6-alkenyl, C2-6-alkynyl, CN, halogen, OR2.8, COOR2.8, COR2.16, NR2.8R2.9, NHCOR2.8, SR2.8, SOR2.8, SO2R2.8, and SO2NR2.8R2.9; or
R2 is C6-10-aryl optionally independently substituted by one or more groups selected from C6-10-aryl-C1-6-alkylene, C5-10-heteroaryl-C1-6-alkylene, C6-10-aryl, and a heterocyclic C3-10 ring, each optionally substituted by a group selected from C1-6-alkyl, C1-6-haloalkyl, COOR2.8, CN, halogen, OR2.8, NHCOR2.8, oxo, a C3-7-cycloalkyl-C1-4 alkylene, a heterocycle-C1-4 alkylene, and a NR2.1R2.2\u2014C1-4-alkylene, wherein:
R2.8 is H, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, a NR2.1R2.2\u2014C1-4-alkylene, or C6-10-aryl, R2.9 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl, and
R2.10 is NHR2.10.1, C1-6-alkylene-O\u2014C1-4-alkyl, or a heterocyclic C3-10 ring optionally substituted by C1-4-alkyl, wherein R2.10.1 is H, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, or C3-7-cycloalkyl; or
R2 is C6-10-aryl to which an aromatic or non-aromatic C3-10 heterocycle is fused; or
R2 is C6-10-aryl optionally substituted by a group selected from C6-10-aryl and a heterocyclic C3-10 ring, each optionally substituted by one or more groups selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-4-haloalkyl, CN, halogen, OR2.8, COOR2.8, COR2.10 NR2.8R2.9, NHCOR2.8, SR2.8, SOR2.8, SO2R2.8, SO2NR2.8R2.9, and oxo;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
9. The compound of formula 1 according to claim 1, wherein:
R2 is C6-10-aryl optionally substituted by one or more groups selected from C1-4-alkyl, CN, halogen, OR2.8, COOR2.8, COR2.10, and NHCOMe, wherein:
R2.8 is C1-4-alkyl or C6-10-aryl;
R2.10 is NHR2.10.1, morpholinyl, or methylpiperazinyl; and
R2.10.1 is H, cyclopropyl, or C1-4-alkyl optionally substituted by one or more groups selected from O\u2014C1-4-alkyl, OH, or C6-10-aryl; or
R2 is C6-10-aryl optionally substituted by a group selected from phenyl and a heterocyclic C3-10 ring, each optionally substituted by C1-4-alkyl, COOR2.8, CN, halogen, OR2.8, NHCOMe, or oxo;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
10. The compound of formula 1 according to claim 1, wherein:
R2 is C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl, each optionally substituted by C1-6-haloalkyl, CN, OR2.1, NR2.1R2.2, NHCOR2.1, SR2.1, SOR2.1, SO2R2.1, SO2NR2.1R2.2, COOR2.1, or CONR2.1R2.2, each optionally substituted by C3-7-cycloalkyl, C6-10-aryl, or a heterocyclic C3-10 ring, each optionally substituted by one or more groups selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, and oxo, wherein:
R2.1 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl, and
R2.2 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl,
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
11. The compound of formula 1 according to claim 1, wherein:
R2 is C1-6-alkyl optionally substituted by C1-4-haloalkyl, CN, OR2.1, NR2.1R2.2, COOR2.1, or CONR2.1R2.2, or optionally substituted by C3-7-cycloalkyl, C6-10-aryl, or a heterocyclic, aromatic C3-10 ring, each optionally substituted by methyl or oxo, wherein:
R2.1 is H or C1-4-alkyl; and
R2.2 is H or C1-4-alkyl,
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
12. The compound of formula 1 according to claim 1, wherein:
R2 is C6-10-aryl optionally independently substituted in the meta position by one or more groups selected from C1-4-alkyl, CN, halogen, OR2.8, COOR2.8, COR2.10, and NHCOMe, wherein:
R2.8 is C1-4-alkyl or C6-10-aryl,
R2.10 is NHR2.10.1, morpholinyl, or methylpiperazinyl, and
R2.10.1 is H, cyclopropyl, or C1-4-alkyl, wherein the C1-4-alkyl is optionally independently substituted by one or more groups selected from O\u2014C1-4-alkyl, OH, and C6-10-aryl; or
R2 is NH(R2.10.1) or cyclohexyl; or
NR1R2 is pyrrolidine and piperazine, each optionally substituted by one or more groups selected from C1-4-alkyl, OH, and C1-4-alkanol
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
13. The compound of formula 1 according to claim 1, wherein:
R3 is phenyl optionally substituted by one or more groups selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-4-haloalkyl, C1-6-alkylene-NR3.1R3.2, CN, halogen, OR3.1, COOR3.1, CONR3.1R3.2, NR3.1R3.2, NHCOR3.1, NO2, SR3.1, SOR3.1, SO2R3.1, SO2NR3.1R3.2, and C1-6-alkylene-NHCOR3.1, wherein:
R3.1 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl, and
R3.2 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
14. The compound of formula 1 according to claim 1, wherein:
R3 is phenyl optionally substituted in the para position by C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-4-haloalkyl, C1-6-alkylene-NR3.1R3.2, CN, halogen, OR3.1, COOR3.1, CONR3.1R3.2, NR3.1R3.2, NHCOR3.1, NO2, SR3.1, SOR3.1, SO2R3.1, SO2NR3.1R3.2, or C1-6-alkylene-NHCOR3.1, wherein:
R3.1 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl, and
R3.2 is H, C1-6-alkyl, C2-6-alkenyl, or C2-6-alkynyl;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
15. The compound of formula 1 according to claim 1, wherein:
R3 is a group of formula 1b
\u2003wherein:
R3.3 is a heterocyclic C3-10 ring optionally independently substituted by one or more groups selected from C1-6-alkyl, oxo, COR3.3.1, COR3.3.2, C1-6-alkylene-R3.3.2, CH2COpyrrolidine, and a heterocyclic C3-10 ring, wherein a sulfur atom optionally contained in the heterocyclic C3-10 ring is optionally present as the oxide or dioxide, wherein: R3.3.1 is C1-6-alkyl, and R3.3.2 is NH2, NH(C1-6-alkyl), or N(C1-6-alkyl)2; or
R3.3 is a bicyclic ring or a heterocyclic spiro ring;
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
16. The compound of formula 1 according to claim 1, wherein:
R3 is a group of formula 1c
\u2003wherein:
A is a bond or C1-6-alkyl optionally substituted by oxo or NMe2;
R3.4 is H or C1-6-alkyl;
R3.5 is C1-6-alkyl optionally substituted by a group selected from C3-7-cycloalkyl, C6-10-aryl, and a C5-10 heterocycle, each optionally substituted by one or more groups selected from halogen, OH, oxo, C1-6-alkyl, O\u2014C1-6-alkyl, C1-6-haloalkyl, a heterocyclic C3-10 ring, and a bicyclic ring, wherein each of these groups is optionally independently substituted by one or more groups selected from oxo, C1-6-alkyl, OH, C6-10-aryl, a heterocyclic ring, C1-6-alkylene-R3.5.1, O\u2014C1-6-alkylene-R3.5.1, and NH\u2014C1-6-alkylene-R3.5.1, wherein R3.5.1 is C6-10-aryl or a heterocyclic C3-10 ring, each optionally substituted by C1-6-alkyl,
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
17. The compound of formula 1 according to claim 1, wherein:
R3 is a group of formula 1d
\u2003wherein:
D is C2-4-alkynyl; and
R3.6 is pyridinyl,
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
18. The compound of formula 1 according to claim 1, wherein:
R3 is a group of formula 1e
\u2003wherein:
R3.7 is H, halogen, C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, or C1-6-haloalkyl;
R3.8 is H, OH, halogen or a group selected from C1-6-alkyl, C2-6-alkenyl, C2-6-alkynyl, C1-6-haloalkyl, O\u2014C1-6-alkyl, C6-10-aryl, a heterocyclic C3-10 ring, and a bicyclic ring, each optionally independently substituted by one or more groups selected from halogen, C1-6-alkyl, OH, C1-6-haloalkyl, and O\u2014C1-6-alkyl,
or a pharmacologically acceptable salt, enantiomer, hydrate, or solvate thereof.
19. A pharmaceutical formulation comprising a compound of formula 1 according to one of claims 1 to 18 and a pharmaceutically acceptable excipient.