CA2620534C

CA2620534C - Substituted imidazo[1,2b]pyridazines as kinase inhibitors, their preparation and use as medicaments

Info

Publication number: CA2620534C
Application number: CA2620534A
Authority: CA
Inventors: Olaf Prien; Benjamin Bader; Ulrich Zuegel; Stuart James Ince; Christoph Huwe; Karina Schuck; Knut Eis; Ulrich Luecking; Rolf Jautelat; Judith Guenther; Manfred Husemann
Original assignee: Bayer Intellectual Property GmbH
Current assignee: Bayer Intellectual Property GmbH
Priority date: 2005-09-02
Filing date: 2006-09-01
Publication date: 2014-05-27
Anticipated expiration: 2026-09-01
Also published as: EP2176266A2; WO2007025540A2; JP2009506993A; DE102005042742A1; WO2007025540A3; CA2620534A1; JP5680824B2

Abstract

The invention relates to novel inhibitors of kinases, methods for preparing such inhibitors, intermediates for the preparation of such inhibitors and uses of such inhibitors.

Description

ALJ/TDS
Substituted imidazo[1,2131pyridazines as kinase inhibitors, their preparation =
and use as medicaments The present invention relates to novel substituted imidazo[1,2b]pyridazines, their preparation and use as medicament for the treatment of various disorders.
The compounds described in this invention are suitable for inhibiting kinases, preferably kinases of the protein kinase (PK) family and, in this connection, to especially for inhibiting kinases of the PKC subfamily, very particularly for inhibiting the PKC theta kinase. The present compounds are suitable as kinase inhibitors for the treatment of a large number of disorders which are attributable to a dysfunction of a kinase, including immunological and general inflammatory processes, and oncological processes, but also disorders such as, for example, type II
diabetes is and asthma, and transplants; preferably inflammatory processes and immune = responses which exhibit the clinical appearance of acute dermatitis, of contact dermatitis but also of psoriasis.
A single publication (Bioorg. Med. Chem. Lett. 2004, 14, 2249-2252.) discloses pyrimidine derivatives with an attached imidazo[1,2b]pyridazine residue as kinase 20 inhibitors. These compounds differ from the compounds of the invention through their structure, in particular on the imidazo[1,2b]pyridazine ring. The patent application WO 02/066481 (AstraZeneca) describes pyridazine-substituted pyrimidines as antiproliferative substances. Further prior art is mentioned hereinafter.

.SRG/US/53343 - 2 -ALJ/TDS
There is a continuing great need for effective medicaments for the treatment of immunological and also cell-proliferative disorders, in particular in dermatological indications.
It has now been found that substituted imidazo[1,2b]pyridazines of the general formula I in which R1, N N

Formula I
to where is aryl or heteroaryl ¨ with the exception of pyrimidine;
A and B are identical or different and are selected from the group consisting of i) H, Hal, -OH, -NR3R4, -CN, or -NO2, ii) optionally mono- or poly-Hal-, -OH-, C3-C6-heterocycloalkyl-, -NR3R4-, -SO2NR3R4- , -S02R3- or -(C0)-NR3-L-substituted Cl-C6-alkyl, Cl -C6-haloalkyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl, where the C3-C6-heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or =
one or more -(CO)- or -(SO2)- groups and/or one or more double bonds, and iii) -NR3(C0)-L, -NR3(C0)-NR3-L, -(C0)-R6, -0-(CH2)p-R6, -(C0)-(NR3)-L, -NR3(CS)-NR3R4, -NR3(S02)-L, -(S02)-NR3R4, -NR3(CO)NR3R4, -(CO)NR3R4, -0O2R7, -NR3(S02)R4 or -0-(CH2)p-aryl, where the substituents in the case of polysubstitution may be identical or different, A and B in addition to the aforementioned definition together form a 0-fused C5-C7-cycloalkyl or C5-C7-heterocycloalkyl ring, where the latter ALJ/TDS
comprises at least one oxygen or one nitrogen atom in the ring, and may optionally comprise additionally in the ring one or more oxygen, nitrogen or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or optionally one or more double bonds, p is 0 to 4, is optionally mono- or poly-hydroxy-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-haloalkyl-, C1-C6-hydroxyalkoxy-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-alkoxyalkoxy-, C3-C6-heterocycloalkyl-, or -NR3R4-substituted C1-C6-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl or C3-C6-heterocycloalkyl, io where the C3-C6 heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or one or more double bonds;
R1 and R2 are identical or different and are selected from the group consisting of j) -H and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6-heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R8-, -NR3R4-, -NR3(C0)-L-, -NR3COOR7-, -COOR7-, -NR3CONR3R4-, -NR3S02R4-, -SO2NR3R4- , -CONR3R4- or -SO2R3-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl or with -(CH2)rR8 radical, where r is a number 0-3, and R8 is a radical H
0 11 or ALJ/TDS
where aryl, heteroaryl, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl groups optionally present in R1 or R2 may be substituted one or more times by -Hal, -CN, - OH, -C1-C6-alkyl, C1-C6-haloalkyl, -C1-C6-alkoxy, C1-C6-haloalkoxy, -C1-C6-hydroxyalkyl, -C3-C6-cycloalkyl, -NO2, -N H2, -C1-C6-haloalkyl, -NR3R4, -CONR3R4, -NR3COR4, NR3S02R4, -COR6, CO2R7, -SO2NR3R4, -SR3, SOR3, -S02R3, -0R3, -0(CH2)pR6, where the substituents in the case of polysubstitution may be identical or different;
where two or more aryl or heteroaryl groups may not be substituents on the same carbon atom in R1 or R2;
po R1 and R2 in addition to the aforementioned definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally comprise additionally in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(C0)- or -(SO2)- groups and/or optionally one or more double bonds, where the ring formed by R1 and R2 may be optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, C1-C6-haloalkoxy-, Cl -C6-haloalkoxyalkyl, -NR3R4, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
R3 and R4 are identical or different and are selected from the group consisting of j) -H, and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or one or ALJ/TDS
more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
R3 and R4 in addition to the aforementioned definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally comprise additionally in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or ¨(SO2)- groups and/or optionally one or more double bonds, where the ring formed by R3 and R4 may be optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, Cl -C6-hydroxyalkyl, Cl -C6-haloalkoxy, Cl -C6-haloalkoxyalkyl, C1-C6-alkoxyalkyl, or by -NR6R7, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
R6 and R7 are identical or different and are selected from the group consisting of j) -H and jj) optionally mono- or poly-Hal-, -OH-, -CN- substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)-or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different, and the isomers, diastereomers, enantiomers and salts thereof, represent effective compounds for inhibiting kinases (defined hereinafter) and therefore can be employed for a number of disorders (defined hereinafter).

ALJ/TDS
Alkyl means in each case a straight-chain or branched alkyl radical such as, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl and decyl.
Alkoxy means in each case a straight-chain or branched alkoxy radical such as, for example, methyloxy, ethyloxy, propyloxy, isoproplyloxy, butyloxy, isobutyloxy, sec butyloxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy or decyloxy.
The alkenyl substituents are in each case straight-chain or branched, with the following radicals being meant for example: 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-methylprop-2-en-1-yl, methylprop-1-en-1-yl, but-1-en-3-yl, but-3-en-1-yl, ally!.
Alkynyl means in each case a straight-chain or branched alkynyl radical which comprises 2-6, preferably 2-4, C atoms. Examples of suitable radicals are the following: ethynyl, propyn-1-yl, propyn-3-y1 (propargyl), but-1-yn-1-yl, but-1-yn-4-yl, is but-2-yn-1-yl, but-1-yn-3-yl, 3-nnethylbut-1-yn-3-yl.
C1-C6-Haloalkyl stands for a straight-chain or branched alkyl radical in which at least one hydrogen atom is replaced by a halogen atom (fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine), such as, for example fluoromethyl, trichloromethyl, 1,2-difluoroethyl, perfluoropropyl, 3,3,3-trifluoropropyl, 1-fluoroisopropyl, perfluorobutyl, etc. Perfluoromethyl and perfluoroethyl groups are very particularly preferred.
C1-C6-Haloalkoxy stands for a straight-chain or branched alkoxy radical in which at least one hydrogen atom is replaced by a halogen atom (fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine), such as, for example, fluoromethoxy, trichloromethoxy, 1,2-difluoroethoxy, perfluoropropoxy, 3,3,3-trifluoropropoxy, 1-fluoroisopropoxy, perfluorobutoxy, etc. Perfluoromethoxy and perfluoroethoxy groups are very particularly preferred.

ALJ/TDS
C3-C6-Heterocycloalkyl stands for an alkyl ring including 3-6 carbon atoms, where the heterocycloalkyl comprises in the ring at least one atom, identical or different, from the following group oxygen, sulfur or nitrogen, and may optionally be interrupted by one or more -(CO)-, -(CS)- or -SO2- groups in the ring, and may optionally comprise one or more double bonds in the ring, and the ring itself may optionally be substituted one or more times, identically or differently.
Examples of heterocycloalkyl which may be mentioned are: oxiranyl, oxethanyl, dioxolanyl, dithianyl, dioxanyl, aziridinyl, azetidinyl, tetrahydrofuranyl, tetrahydropyranyl, dihydrooxazolyl, tetrahydrooxazolyl, tetrahydrothiazolyl, tetrahydroisoquinolinyl, octahydroisoquinolinyl, tetrahydroquinolinyl, octahydroquinolinyl, tetrahydroimidazolonyl, pyrazolidinyl, pyrrolidinyl, pyrrolidonyl, piperidinyl, piperidonyl, piperazinyl, piperazinonyl, N-methylpyrolidinyl, 2-hydroxy-methylpyrolidinyl, 3-hydroxypyrolidinyl, N-methylpiperazinyl, N-benzylpiperazinyl, N-acetylpiperazinyl, N-methylsulfonylpiperazinyl, 4-hydroxypiperidinyl, 4-amino-carbonylpiperidinyl, 2-hydroxyethylpiperidinyl, 4-hydroxymethylpiperidinyl, imidazolidinyl, tetrahydroimidazolonyl, nnorpholinyl, thiomorpholinyl, 1,1-dioxothio-morpholinyl, trithianyl, tetrahydrotriazinthionyl, triazinthionyl, quinuclidinyl, nortropinyl, pydridonyl.
Preferred heterocycloalkyl groups which may be mentioned are:
tetrahydropyranyl, pyrrolidinyl, piperidinyl, N-methylpiperidinyl, piperazinonyl, N-methylpiperazinyl, morpholinyl, pyrridonyl.
Substituents on the heterocycloalkyl ring may be for example: cyano, halogen, hydroxy, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkoxyalkyl, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, aryl or optionally identically or differently mono- or poly-halogen-, hydroxyl- or C1-C6-alkylthio-substituted alkyl, C1-C6-haloalkyl or a substituent from the group ¨(C0)-C1-C6-alkyl, ¨(CO)-O-C1 -C6-alkyl, ¨(S02)-phenyl, -NH2, -N(Ci-C6-alky1)2, -NH(C1-alkyl) etc.

ALJ/TDS
Cycloalkyl means monocyclic alkyl rings such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, but also bicyclic rings or tricyclic rings such as, for example, adamantanyl. The cycloalkyl may also optionally be benzo-fused, such as, for example, (tetralin)yl etc.
Preferred cycloalkyl groups are cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Halogen means in each case fluorine, chlorine, bromine or iodine.
The aryl radical in Q and the aryl radical optionally present in R1 and R2 includes in each case 3-12 carbon atoms and may in each case be benzo-fused. Examples which may be mentioned are: cyclopropenyl, cyclopentadienyl, phenyl, tropyl, cyclooctadienyl, indenyl, naphthyl, azulenyl, biphenyl, fluorenyl, anthracenyl, tetralinyl etc.
The heteroaryl radical Q includes in each case 5-16 ring atoms and may comprise in place of the carbon one or more identical or different heteroatoms such as oxygen, nitrogen or sulfur in the ring, and may be mono-, bi- or tricyclic, and may is additionally be in each case benzo-fused. Pyrinnidine is not included as group Q in the definition of heteroaryl.
Examples which may be mentioned are: thienyl, furanyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, etc. and benzo derivatives thereof, such as, for example, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, indazolyl, indolyl, isoindolyl, etc.; or pyridyl, pyridazinyl, pyrazinyl, triazinyl, etc. and benzo derivatives thereof, such as, for example, quinolyl, isoquinolyl, etc.; or oxepinyl, azocinyl, indolizinyl, indolyl, indolinyl, isoindolyl, indazolyl, benzimidazolyl, purinyl, etc. and benzo derivatives thereof; or quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, tetralinyl, etc.
Preferred heteroaryl radicals are for example 5-membered heteroaromatic rings such as thienyl, furanyl, oxazolyl, thiazolyl, pyrazolyl, imidazolyl and benzo ALJ/IDS
derivatives of the 5-membered heteroaromatic rings, and 6-membered heteroaromatic rings, such as pyridinyl, triazinyl, and benzo derivatives of the 5-membered heteroaromatic rings, such as quinolinyl, isoquinolinyl.
The heteroaryl radical optionally present in R1 or R2 includes in each case 5-16 ring atoms and may comprise instead of the carbon one or more identical or different heteroatoms such as oxygen, nitrogen or sulfur in the ring, and may be mono-, bi-or tricyclic, and may additionally in each case be benzo-fused.
Examples of the heteroaryl radical in R1 or R2 which may be mentioned are:
thienyl, furanyl, pyrroidinylyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, to isothiazolyl, oxadiazolyl, triazolyl, thiadiazolyl, etc. and benzo derivatives thereof, such as, for example, benzofuranyl, benzothienyl, benzoxazolyl, benzimidazolyl, indazolyl, indolyl, isoindolyl, etc.; or pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, etc. and benzo derivatives thereof, such as, for example, quinolyl, isoquinolyl, etc.; or oxepinyl, azocinyl, indolizinyl, indolyl, indolinyl, isoindolyl, is indazolyl, benzimidazolyl, purinyl, etc. and benzo derivatives thereof;
or quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, xanthenyl, tetralinyl, etc.
Examples of preferred heteroaryl radicals in R1 or R2 are 5-membered 20 heteroaromatic rings such as thienyl, pyrazolyl, furanyl, oxazolyl, thiazolyl, triazolyl, imidazolyl and benzo derivatives thereof and 6-membered heteroaromatic rings such as pyridinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl and benzo derivatives thereof.
Particularly preferred heteroaryl radicals in R1 or R2 are thienyl, pyrazolyl, furanyl, 25 oxazolyl, thiazolyl, triazolyl, imidazolyl, pyridinyl, pyrazinyl, triazinyl, quinolinyl, isoquinolinyl.
If a plurality of aryl or heteroaryl groups are present in R1 or R2, two or more aryl or heteroaryl groups may not be substituents on the same carbon atom.

ALJ/TDS
Thus, for example, a group C,51-1 -CH

is precluded as group R1 or R2.
Should aryl, heteroaryl, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl groups be present in R1 or R2, these may be substituted one or more times by -Hal, -CN, -OH, -Cl -C6-alkyl, Cl -C6-haloalkyl, -Cl -C6-alkoxy, Cl -C6-haloalkoxy, -Cl -C6-hydroxyalkyl, -C3-C6-cycloalkyl, -NO2, -NH2, -C1-C6-haloalkyl, -NR3R4, -CONR3R4, -NR3COR4, NR3S02R4, -COR6, CO2R7, -SO2NR3R4, -SR3, SOR3, --S02R3, -0R3, -0(CH2)pR6, where the substituents in the case of polysubstitution may be identical or different. In a preferred embodiment, the aryl, heteroaryl, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl groups present in R1 or R2 have not more than 3 of the abovementioned substituents.
Isomers mean chemical compounds of the same molecular formula but different is chemical structure. A distinction is made in general between constitutional isomers and stereoisomers.
Constitutional isomers have the same molecular formula but differ through the manner of attachment of their atoms or atomic groups. These include functional isomers, positional isomers, tautomers or valence isomers.
Stereoisomers have in principle the same structure (constitution) ¨ and thus also the same molecular formula ¨ but differ through the spatial arrangement of the atoms.
A distinction is made in general between configurational isomers and conformational isomers. Configurational isomers are stereoisomers which can be converted into one another only by breaking a bond. These include enantiomers, diastereomers and E/Z (cis/trans) isomers.

ALJ/TDS
Enantiomers are stereoisomers which are related to one another as image and mirror image and have no plane of symmetry. All stereoisomers which are not enantiomers are referred to as diastereomers. E/Z (cis/trans) isomers at double bonds are a special case.
Conformational isomers are stereoisomers which can be converted into one another by rotation of single bonds.
See also the IUPAC rules section E (Pure App!. Chem. 1976, 45, 11-30.) concerning the categorization of the type of isomerism.
The compounds of the invention of the general formula I also encompass the to possible tautomeric forms and include the E or Z isomers or, if a chiral center is present, also the racemates and enantiomers. Double-bond isomers are also to be understood thereby.
The compounds of the invention may also exist in the form of solvates, in particular of hydrates, in which case the compounds according to the invention accordingly comprise polar solvents, in particular water, as structural element of the crystal lattice of the compounds according to the invention. The proportion of polar solvent, in particular water, may be in a stoichiometric or else non-stoichiometric ratio. Terms used in connection with stoichiometric solvates, hydrates are also hemi-, (semi-), mono-, sesqui-, di-, tri-, tetra-, penta-, etc. solvates or hydrates.
If an acidic function is present, suitable salts are the physiologically tolerated salts of organic and inorganic bases such as, for example, the readily soluble alkali metal and alkaline earth metal salts, and salts of N-methylglucamine, dimethylglucamine, ethylglucamine, lysine, 1,6-hexanediamine, ethanolamine, glucosamine, sarcosine, serinol, trishydroxymethylaminomethane, aminopropanediol, Sovak base, 1-amino-2,3,4-butanetriol.
If a basic function is present, the physiologically tolerated salts of organic and inorganic acids are suitable, such as hydrochloric acid, sulfuric acid, phosphoric acid, citric acid, tartaric acid, fumaric acid, maleic acid, malic acid and others.

ALJ/TDS
Preferred compounds of the general formula I are those compounds in which R1 and R2 are identical or different and are selected from the group consisting of j) -H and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3R4-, -NR3(C0)-L-, or -NR3COOR7-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen io and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different. Q, A, B, R3, R4, R6, R7, p and L may in this case be varied as defined above.
Further preferred compounds of the general formula I are those in which R1 and is are identical or different and are selected from the group consisting of j) -H and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryloxy-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3R4-, -NR3(C0)-L-, or -NR3COOR7-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, 20 Cl -C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, where the group aryl or heteroaryl defined in jj) may be substituted as long as alkyl is not 25 involved, and where the substituents in the case of polysubstitution may be identical or different. Q, A, B, R3, R4, R6, R7, p and L may in this case be varied as defined above.
Further preferred compounds of the general formula I are those in which Q is:
-OH-, -Hal-, -CN-, alkyl-, -0R6-, or -NR3R4-substituted phenyl, pyridyl, thiophenyl, 30 furyl, imidazolyl or pyrazolyl, where R1 and R2 are identical or different and are ALJ/TDS
selected from the group consisting of j) -H and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryloxy-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3R4-, -NR3(C0)-L- or -NR3COOR7-substituted C1-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, where the group aryl or heteroaryl defined in jj) may be io substituted as long as alkyl is not involved, and where the substituents in the case of polysubstitution may be identical or different. R3, R4, R6, R7, p and L may in this case be varied as defined above.
Further preferred compounds of the general formula I are those in which R1 and R2 are identical or different and are selected from the group consisting of -H, NR3R4-substituted C1-C4 alkyl, optionally additionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3(C0)-L- or -NR3COOR7-substituted, optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -(C0)-R6-, -NR3(C0)-L-, -NR3R4- or -NR3COOR7-substituted C5-C6-cycloalkyl, C5-heterocycloalkyl, where R3 and R4 may optionally be identically or differently C1-C6-alkyl, C1-C6-haloalkyl, where R3 and R4 may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(C0)- or -(SO2)- groups and/or optionally one or more double bonds, and where R6 and R7 is identically or differently -H, -OH, C1-C6-alkoxy, C1-C6-haloalkoxy, or C1-C3 alkyl.

ALJ/TDS
Particularly preferred compounds of the general formula I are those in which R1 is selected from the group consisting of ¨H and C1-C3-alkyl, where R2 is selected from the group consisting of NR3R4-substituted C3-C4 alkyl, optionally additionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3(C0)-L- or -NR3COOR7-substituted, where R3 and R4 are identically or differently optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, C1-C6-haloalkyl, where R3 and R4 may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(C0)- or -(SO2)- groups and/or optionally one or more double bonds, and where R6 and R7 is identically or differently -H, -OH, C1-C6-alkoxy, C1-C6-haloalkoxy, or C1-C3 alkyl.
In a further preferred embodiment, R1 or R2 is a hydrogen atom.
The following compounds mentioned in the examples are particularly preferred:
= 2.0 ¨ 2.21 = 3.0 ¨ 3.80 = 4.0 ¨ 4.11 = 5.0 ¨ 5.389 = 6.0 ¨ 6.2 = 7.0 ¨ 7.1 = 8.0 ¨ 8.1 A further aspect of the present invention is represented by a compound of the general formula ha and the use thereof for preparing a compound according to formula I, in which ALYTDS
R1, NfN r:Ni ,N

General formula ha is a halogen atom (preferably chlorine or bromine), R1 and R2 are identical or different and selected from the group consisting of j) ¨H and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3R4-, -NR3(C0)-L- or -NR3COOR7-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
R1 and R2 in addition to the preceding definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or -(S02)-groups and/or optionally one or more double bonds, where the ring formed via R1 and R2 may be optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-haloalkoxyalkyl, C1-C6-haloalkoxy, C1-C6-alkoxyalkyl, -NR3R4, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or ALJ/TDS
-(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
where three or more nitrogen atoms in the ring may not be linked directly to one another;
where aryl, heteroaryl, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl groups optionally present in R1 or R2 may be substituted one or more times by -Hal, -CN, - OH, -C1-C6-alkyl, C1-C6-haloalkyl, -C1-C6-alkoxy, C1-C6-haloalkoxy, -C1-C6-hydroxyalkyl, -C3-C6-cycloalkyl, -NO2, -NH2, -C1-C6-haloalkyl, -NR3R4, -CONR3R4, -NR3COR4, NR3S02R4, -COR6, CO2R7, -SO2NR3R4, -SR3, SOR3, --SO2R3, -0R3, -0(CH2)pR6, where the substituents in the case of polysubstitution may be identical or different;
R3 and R4 are identical or different and selected from the group consisting of j)-H
and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
R3 and R4 in addition to the preceding definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or -(SO2)-groups and/or optionally one or more double bonds, where the ring formed by R3 and R4 may optionally be substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, ALJ/TDS
Cl-C6-hydroxya I kyl, C1-C6-alkoxyalkyl C1-C6-haloalkoxyalkyl, C1-C6-haloalkyl or -NR6R7, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
R6 and R7 are identical or different and selected from the group consisting of j)¨H
and jj) optionally mono- or poly-Hal-, -OH-, -CN-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-er5,N
X N

alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionallyt comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different, and the isomers, diastereomers, enantiomers and salts thereof.
is A further aspect of the present invention is represented by a compound of the general formula lib and the use thereof for preparing a compound according to formula I, in which general formula lib X is chlorine, bromine, 0-S02-CF3 or 0-S02-C4F9;
Q is aryl or heteroaryl ¨ with the exception of pyrimidine;
A and B are identical or different and selected from the group consisting of i) H, Hal, -OH, -NR3R4, -CN or -NO2, ALJ/TDS
ii) optionally mono- or poly-Hal-, -OH-, C3-C6-heterocycloalkyl-, -NR3R4-, -SO2NR3R4-, -S02R3- or -(C0)-NR3-L-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or one or more double bonds, and iii) -NR3(C0)-L, -NR3(C0)-NR3-L, -(C0)-R6, -0-(CH2)p-R6, -(C0)-(NR3)-L, -NR3(CS)-NR3R4, -NR3(S02)-L, -(S02)-NR3R4, -NR3(CO)NR3R4, -(CO)NR3R4, -CO2R7, -NR3(S02)NR4 or -0-(CH2)p-aryl, where the substituents in the case of polysubstitution may be identical or different, A and B in addition to the preceding definition together form a Q-fused C5-C7-cycloalkyl or C5-C7-heterocycloalkyl ring, where the latter comprises at least one oxygen or nitrogen atom in the ring and may optionally additionally comprise in the ring one or more oxygen, nitrogen or sulfur atoms and/or one or more -(C0)- or -(SO2)- groups and/or optionally one or more double bonds, isOto4, L is optionally mono- or poly-hydroxy-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-hydroxyalkoxy-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-alkoxyalkoxy-, C3-C6-heterocycloalkyl- or -NR3R4-substituted C1-C6-alkyl, C1-C6-haloalkyl or C3-C6-cycloalkyl or C3-C6-heterocycloalkyl, where the C3-C6 heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(C0)- or -(SO2)-groups and/or one or more double bonds;
R3 and R4 are identical or different and selected from the group consisting of j) -H, and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-hydroxyalkyl-, C3-C6-ALJ/TDS
cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
lo R3 and R4 may in addition to the preceding definition together form a C3-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or -(SO2)-groups and/or optionally one or more double bonds, where the ring formed via R3 and R4 may optionally be substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, Cl -C6-hydroxyalkyl, Cl -C6-alkoxyalkyl, Cl -C6-haloalkoxyalkyl, C1-C6-haloalkoxy or by -NR6R7, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents may in the case of polysubstitution be identical or different;
R6 and R7 are identical or different and selected from the group consisting of j)¨H
and jj) optionally mono- or poly-Hal-, -OH-, -CN-substituted C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different ALJ/TDS
and the isomers, diastereomers, enantiomers and salts thereof.
These compounds of the general formulae ha and lib represent advantageous intermediates and can be employed in the synthesis of the abovennentioned compounds of the general formula I.
The explanations made above for the compounds of the formula I, including the preferred embodiments of the radicals, apply in principle analogously to the compounds of the formulae Ila and Ilb. It is particularly preferred for 0 to be an optionally mono- or poly-OH-, -Hal-, -ON-, alkyl-, -0R6- or -NR3R4-substituted phenyl, pyridyl, thiophenyl, furyl, imidazolyl or pyrazolyl. It is further preferred for X
to be ¨CI or ¨Br.
The following intermediates of the invention are particularly preferred: 3-bromo-6-chloroimidazo[1,2-b]pyridazines, imidazo[1,2-b]pyridazin-6-y1-(3-pyrrolidin-1-ylpropyl)amines, 6-chloro-3-phenylimidazo[1,2-b]pyridazines, 6-chloro-3-(3-chlorophenyl)imidazo[1,2-13]pyridazines, 6-chloro-3-(1 -methyl-1 H-pyrazol-4-yl)imidazo[1,2-b]pyridazines, 6-chloro-3-thiophen-3-ylimidazo[1,2-b]pyridazines.
The intermediates 1.0-1.28 described in the examples are very particularly preferred.

ALSTDS
Synthesis scheme:
A N/_ X N
AL A

General formula Ilb NH ey-14 N N
X N X N X N

B
VII
General formula I
R1, 121, A -1;1-.?
N N

VI
IV
General formula ha The invention accordingly also relates to a method for preparing a compound of the invention with the following stages of the method:
Al) 3-amino-6-halopyrazine is converted into 6-haloimidazo[1,2-b]pyridazine II, A2) the product from stage Al is converted into a 3-halo-6-haloimidazo[1,2-b]pyridazine III, A3) the product from stage A2 is converted by reaction with a compound NHR1R2 io into the compound according to the general formula Ila, A4) the product from stage A3 is converted into the compound according to the general formula I, or B1) 3-amino-6-halopyrazine is converted into 6-haloimidazo[1,2-b]pyridazine II, is B2) the product from stage B1 is converted into a 3-halo-6-haloimidazo[1,2-b]pyridazine III, ALJ/TDS
=
B3) the product from stage B2 is converted into the compound according to the general formula lib, B4) the product from stage B3 is converted into the compound according to the general formula I, or Cl) 3-amino-6-halopyrazine is converted into 6-haloimidazo[1,2-14yridazine II, CZ) the product from stage Cl is converted by reaction with a compound NHR1R2 into an imidazo[1,2-b]pyridazin-6-yI)-(R1)-(R2)-amine IV, C3) the product from stage C2 is converted into the compound according to the general formula Ila, C4) the product from stage 03 is converted into the compound according to the general formula I.
Said reactions are preferably carried out as follows:
is Al) 3-amino-6-halopyrazine is reacted with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, A2) the product from stage Al is reacted with N-bromosuccinimide to give a 3-bromo-6-haloimidazo[l ,2-b]pyridazine, A3) the product from stage A2 is converted by reaction with a compound NHR1 R2 in a Buchwald-Hartwig cross-coupling reaction into a (3-bromoimidazo[1,2-b]pyridazin-6-yI)-(R1)-(R2)-amine, A4) the product from stage A3 is reacted for example with a boronic acid which is optionally substituted by the radicals A and B to give the compound according to the general formula I, ALJ/TDS
or B1) 3-amino-6-halopyrazine is reacted with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, B2) the product from stage B1 is reacted with N-bromosuccinimide to give a 3-bromo-6-haloimidazo[1,2-b]pyridazine, B3) the product from stage B2 is reacted for example with a boronic acid which is optionally substituted by the radicals A and B to give the compound according to the general formula II, B4) the product from stage B3 is converted by reacting with a compound NHR1R2 io in a Buchwald-Hartwig cross-coupling reaction into the compound according to the general formula I, or Cl) 3-amino-6-halopyrazine is reacted with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, in a Buchwald-Hartwig cross-coupling reaction into an imidazo[1,2-b]pyridazin-6-y1)-(R1)-(R2)-amine, C3) the product from stage C2 is reacted with N-bromosuccinimide to give a (3-bromoimidazo[1,2-b]pyridazin-6-yI)-(R1)-(R2)-amine, optionally substituted by the radicals A and B to give the compound according to the general formula I.
The compounds of the invention are particularly preferably prepared by synthesis route Al-A4.

ALJ/TDS
To protect sensitive side groups, said synthesis routes can also be prepared with use of protective groups. Such protective group techniques are known to the skilled worker, e.g. from T.W. Greene, P.G.M. Wuts õProtective Groups in Organic Synthesis", 2nd edition, John Wiley and Sons, 1991.
Stages Al, B1 and Cl can be carried out for example by heating with, for example, chloracetaldehyde at 60 to 130 C, in particular 100 to 130 C, in n-butanol as solvent and for a period of from 1 hour to 10 days, in particular 3 to 6 days.
The amination (stages A3, B4 and C2 respectively) can be carried out for example by heating with the appropriate amine at 90-180 C, in particular 90 C, for a period of from 1 hour to 24 hours, in particular 1 hour to 16 hours. The heating can take place by means of conventional heating or else by means of microwave radiation through a suitable apparatus. The use of an auxiliary base such as, for example, K2CO3 or Et3N is not always necessary. The use of a solvent such as, for example, acetonitrile, Et0H, n-BuOH or NMP is not always necessary. It is possible to use for the amination for example the so-called Buchwald-Hartwig cross-coupling reaction. The Buchwald-Hartwig cross-coupling reaction can be carried out for example in accordance with one of the references D. Zim, S.L. Buchwald, Org. Lett., 5:2413-2415 (2003) or S. Urgaonkar, M.
Nagarajan, J.G. Verkade, J. Org. Chem., 68:452-459 (2003).
The reaction to give the 3-bromo intermediate (stages A2, B2 and C3) can take place by introducing the precursor compound into chloroform and adding the N-bromosuccinimide at ¨5 to 30 C, in particular at 0 to 10 C, followed by reaction for 1 hour to 2 days, in particular 5 to 15 hours, at 0 to 30 C, in particular at 15 to 25 C. However, alternative synthesis routes for preparing the 3-halo intermediates of the invention are also known to the skilled worker.
Stages A4, B3 and C4 can be carried out for example by introducing the precursor compound into dimethoxyethane and adding a boronic acid in the presence of a palladium(0) source, for example bis(dibenzylidene-acetone)palladium(0), of a ligand, for example tri-o-tolylphosphine and of a base, for example sodium bicarbonate, and by heating under reflux for 5 to 40 hours, in particular 10 to 20 hours.
Where the preparation of the starting compounds is not described, they are known or can be prepared in analogy to known compounds or methods described herein.
The isomer mixtures can be fractionated by conventional methods such as, for example, crystallization, chromatography or salt formation into the isomers such as, for example, into the enantiomers, diastereomers or E/Z isomers, as long as the isomers are not in equilibrium with one another.
The salts are prepared in a conventional way by adding the equivalent amount or an excess of a base or acid, which is in solution where appropriate, to a solution of the compound of the formula I, and removing the precipitate or working up the solution in a conventional way.
Additional reference is made to the examples for merely exemplary details of the synthesis.
The invention further relates also to intermediates of the invention as described herein.
Compounds of the invention are suitable as kinase inhibitors, in particular of tyrosine and serine/threonine kinases. The compounds of the invention of the general formula I are inter alia inhibitors of the protein kinase C family, such as, for example, PKC theta, delta, iota, alpha and zeta.
An inhibitor of a kinase can therefore be employed on the one hand for investigating the mechanisms of functioning of the kinase, in particular research into a disorder which derives from a dysfunction of the kinase. However, it is also possible for a disorder derived from the dysfunction of the kinase to be treated or prevented using the kinase inhibitor.

ALJ/TDS
The invention therefore further relates to the use of a compound of the invention of the general formula I for producing a pharmaceutical composition, in particular for inhibiting a cellular kinase, preferably kinases of the protein kinase (PK) family and in this connection in particular for inhibiting kinases of the PKC
subfamily, very especially for inhibiting the PKC theta kinase, and for the treatment or for the prophylaxis of a disorder which is associated with overexpression or mutation of a cellular kinase, in particular of such a cellular kinase.
It has additionally been found that, surprisingly, the compounds of the invention are also inhibitors of kinases of the ALK family. ALK means "activin receptor-like io kinase" or "activin-like kinase". In this connection, the compounds of the invention act on ALK1, ALK2, ALK4 and ALK5, in particular on ALK1 and ALK5. The compounds of the invention are therefore also suitable for the treatment or prophylaxis of disorders which are associated with overexpression or mutation of a kinase of the ALK family, in particular ALK1 and ALK5.
is In one embodiment of the invention, the disorder is a disorder from the group consisting of epidermal hyperproliferation such as psoriasis, Alzheimer's, autoinflammatory disorders, fibroses, impaired wound healing, diabetic retinopathy, nephropathy, age-related macular degeneration, Crohn's disease, exaggerated immune response, contact dermatitis, atopic dermatitis, multiple 20 sclerosis, ALS, diabetes, asthma.
In another embodiment of the invention, the disorder is a disorder from the group consisting of benign tumors, malignant tumors, leukemia such as myeloblastic leukemia, lymphoma, sarcoma such as osteosarcoma or chondrosarcoma, neuroblastoma, Wilm's tumor, malignant neoplasms of the bladder, breast, lung, 25 pancreas, prostate, kidney, neoplasms of epithelial origin such as carcinoma of the breast or metastases thereof.
In a further embodiment of the invention, compounds of the invention are used for modulating, in particular reducing, an immune response, for example after a transplantation has taken place to prevent rejection of an organ.

ALJITDS
A pharmaceutical composition of the invention can be produced by mixing a physiologically effective dose of a compound of the invention with at least one pharmaceutical excipient and manufacturing a desired dosage form.
A suitable physiologically effective dose is for example an amount of from 1 to 1000 mg, in particular from 50 to 500 mg, per dose unit per day for a person weighing 75 kg, it being possible to give the dose as a single dose to be administered once or divided into 2 or more daily doses.
The pharmaceutical manufacture of a pharmaceutical composition of the invention can take place in a manner customary in the art. Examples of suitable counter ions for ionic compounds are Na+, K+, Li+ or cyclohexylammonium, or Cl, Br, acetate, trifluoroacetate, propionate, lactate, oxalate, malonate, maleate, citrate, benzoate, salicylate etc. Examples of suitable solid or liquid pharmaceutical presentations are granules, powders, coated tablets, tablets, (micro)capsules, suppositories, syrups, solutions, ointments, suspensions, emulsions, drops or solutions for injection (i.v., i.p., i.m., s.c.) or atomization (aerosols), transdermal systems, and products with protracted release of active ingredient which are produced by using conventional aids such as carriers, disintegrants, binders, coating agents, swelling agents, glidants or lubricants, and preservatives, stabilizers, wetting agents or emulsifiers;
salts to alter the osmotic pressure or buffers, flavorings, sweeteners and solubilizers. Carrier systems which can also be used are surface-active excipients such as salts of bile acids or animal or vegetable phospholipids, but also mixtures thereof, and liposomes or constituents thereof. Excipients which may be mentioned are magnesium carbonate, magnesium stearate, gum Arabic, titanium dioxide, lactose, mannitol and other sugars, talc, milk protein, gelatin, starch, cellulose and its derivatives, animal and vegetable oils such as fish liver oil, sunflower, peanut or sesame oil, polyethylene glycols and solvents such as, for example, sterile water and monohydric or polyhydric alcohols, for example glycerol. Preferred dosage forms are for topical application (ointments, transdermal systems, patches, dressings), for oral administration (tablets, coated tablets, solutions, powders) or for parenteral use (suspension, injection).

A pharmaceutical composition of the invention can be produced by mixing at least one inhibitor used according to the invention in defined dose with a pharmaceutically suitable and physiologically tolerated carrier and, where appropriate, further suitable active ingredients, additives or excipients with a defined dose of inhibitor and manufacturing the desired dosage form. These pharmaceutical products are likewise an aspect of the present invention.
Finally, the invention also relates to a method for the treatment or prophylaxis of a disorder which is associated with overexpression of a cellulose kinase, where a pharmaceutical composition comprising a physiologically effective dose of a lo compound as described herein is administered to a person suffering from or under threat of suffering from the disorder.
The invention is explained in more detail below by means of examples which represent merely exemplary embodiments.
Preparation of the starting materials:
6-Chloroimidazo[1,2-b]pyridazine (Example 1.0 OP 3055) .7nr.NH2 CIN
5.0 g (38.6 mmol) of 3-amino-6-chloropyridazine were heated together with 4.7 ml (40 mmol) of chloracetaldehyde (55% strength in water) in 15 ml of n-butanol at 120 C for a period of 5 days. After the reaction was complete, the reaction mixture was added to saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were then washed with sat. sodium chloride solution and dried over sodium sulfate, and the solvent was removed in vacuo. In the final purification by chromatography on silica gel, 4.17 g (70%) of the desired product were isolated in the form of an amorphous white solid.

1H-NMR (CDCI3, stored over molecular sieves): 6 = 7.06 (d, 1H); 7.79 (d, 1H);
7.92, (d, 1H); 7.96 (d, 1H) ppm.
3-Bromo-6-chloroimidazot1,2-13]pyridazine (Example 1.1 OP 3056) cr Br 478 mg (3.11 mmol) of 6-chloroimidazo[1,2-b]pyridazine were introduced into 10 ml of chloroform under argon and, while cooling in ice, 664 mg (3.73 mmol) of N-bromo-succuinimide were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The reaction mixture was then mixed with io water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with sat.
sodium chloride solution and dried over sodium sulfate. In the final removal of the solvent in vacuo, the desired product was isolated in quantitative yield in the form of is an amorphous white solid which was employed without further chromatographic purification in subsequent reactions.
1H-NMR (CDCI3, stored over molecular sieves): 6 = 7.12 (d, 1H); 7.79 (s, 1H);
7.90, (d, 1H) ppm.
20 6-Chloro-3-iodoimidazo[1,2-b]pyridazine (Example 1.2) CI CI N

ALJ/TDS
14 g of 6-chloroimidazo[1,2-b]pyridazine (Example 1.0) were suspended in 364 ml of acetonitrile, and 20.51 g of N-iodosuccinimide were added. The mixture was stirred at RT for 19 hours. A further 4.31 g of N-iodosuccinimide were added, and the mixture was stirred for 24 hours. The reaction was cooled and the precipitated solid was filtered off with suction, washed with acetonitrile and dried. 17.67 g of the desired product are obtained.
1H-NMR (300 MHz, d6-DMS0): 8 = 7.40 (d, 1H); 7.95 (s, 1H); 8.19 (d, 1H) ppm.
Preparation of the intermediates of the invention:
Imidazot1,2-14pyridazin-6-yl-(3-pyrrolidin-1-ylpropyl)amine (Example 1.3) N
Cl,rJNA() ____________________________ CriN
100 mg (0.65 mmol) of 6-chloroimidazo[1,2-b]pyridazine were introduced into 9 ml of tetrahydrofuran and 3 ml of dimethylformamide under argon. 83 mg (0.65 mmol, 1.0 eq.) of 1-(3-aminopropyl)pyrrolidine, 60 mg (0.065 mmol, 0.1 eq.) of (dibenzylideneacetone)palladium(0), 41 mg (0.065 mmol, 0.1 eq.) of rac. 2,2`-bis(diphenylphosphino)-1,1`binaphthyl and 125 mg (1.3 mmol, 2.0 eq) of sodium tort-butoxide were successively added, and the mixture was then heated at 80 C for 4 h.
The reaction mixture was then mixed with water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with sat. sodium chloride solution and dried over sodium sulfate. In the final purification by chromatography on silica gel, 53 mg (39%) of the desired product were isolated in the form of an amorphous white solid.

ALJ/TDS
1H-NMR (CDCI3, stored over molecular sieves): 6 = 1.77-1.89 (m, 6H); 2.54 (m, 4H); 2.66 (m, 2H); 3.43 (m, 2H); 6.18 (s. br, 1H); 6.31 (d, 1H); 7.44(d, 1H);
7.57, (d, 1H); 7.61 (d, 1H) ppm.
LC-MS (ACN/H20 0.01% HCOOH; 33x4.6x1.5p ODSII, Gradient: 100% H20 90% ACN in 4.5 min): t = 0.41 min; m/z = 246 [M+H] 38%; 123 [M+H]+ 100%;
6-Chloro-3-phenylimidazot1,2-Npyridazine (Example 1.4) Br 500 mg (2.15 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine were introduced into 25 ml of dimethoxyethane under argon. 290 mg (2.4 mmol, 1.1 eq.) of phenyl io boronic acid, 250 mg (0.43 mmol, 0.2 eq.) of bis(dibenzylideneacetone)palladium(0) and 130 mg (0.43 mmol, 0.2 eq.) of tri-o-tolylphosphine, 2.2 ml of saturated sodium bicarbonate solution, were successively added, and the reaction mixture was heated under reflux for 15 hours.
The reaction mixture was then mixed with ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with sat. sodium chloride solution and dried over sodium sulfate. In the final purification by chromatography on silica gel, 239 mg (48%) of the desired product were isolated.
1H-NMR (CDCI3, stored over molecular sieves): 6 = 7.02 (d, 1H); 7.35 (m, 1H);
7.43 (m, 2H); 7.89 (d, 1H); 7.95 ¨ 8.0 (m, 3H) ppm.
MS (ES+): m/z = 230 (100%)([M+H]; 232 (45%).

ALJ/TDS
2-(3-Bromoimidazo[1,2-b]pyridazin-6-ylamino)ethanol (Example 1.5) ________________________________________________________________ HONAN,14-.?
Br Br 400 mg (1.72 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine and 2.0 ml (33.4 mmol) of ethanolamine were stirred at 90 C for 16 h. After cooling, the mixture was concentrated. The resulting residue was purified by chromatography (DCM/Et0H 9:1). 282 mg of the product were obtained.
1H-NMR (300 MHz; d6-DMS0): = 3.28 ¨ 3.34 (m, 2H, covered by solvent); 3.56 ¨
3.61 (m, 2H); 4.74 (t, 1H); 6.71 (d, 1H); 7.13 (t, 1H); 7.43 (s, 1H); 7.64 (d, 1H) ppm.
MS (El+): m/z = 256; 258 (M+H)+. [mol. weight = 257.09].
2-(3-lodoimidazo(1,2-14pyridazin-6-ylamino)ethanol (Example 1.6) Hos,N
N
562 mg (2.0 mmol) of 6-chloro-3-iodoimidazo[1,2-b]pyridazine and 2.35 ml (39.2 mmol) of ethanolamine were stirred at 90 C for 16 h. After cooling, the mixture was concentrated. The resulting residue was purified by chromatography (DCM/Et0H 9:1). 224 mg of the product were obtained.
1H-NMR (300 MHz; d6-DMS0): 8 = 3.27 ¨ 3.35 (m, 2H, covered by solvent); 3.58 ¨

3.63 (m, 2H); 4.72 (t, 1H); 6.67 (d, 1H); 7.06 (t, 1H); 7.42 (s, 1H); 7.59 (d, 1H) ppm.
MS (ESI+): m/z = 305 (M+H)+. [mol. weight = 304.09].

The following are prepared in an analogous manner:
Table 1:
Mol. weight Example/
Structure and name of the main isomer 1H-NMR
No. MS (ES+) 358 1.7 r'rN (CDCI3, stored over MW:
846 molecular sieves): 264.12 /
CI - 6 = 7.12 (d, 1H); 7.38 (m, NN
1H); 7.46 (m, 1H); 7.94 (m, MS (ES+) 42H); 8.07 (m, 1H); 8.09 (s, [M+1] +:
CI 1H) ppm. 264 6-Chloro-3-(3-chloro-phenyI)-imidazo[1,2-13]pyridazine .
358 1.8 r\rN (CDCI3, stored over MW:
860 molecular sieves): 233.66 CIN-N---1...1 6 = 4.04 (s, 3H); 7.04 (d, 1H);
7.92 (d, 2H); 7.96 (s, 1H); MS (ES+) / I 8.03 (s, 1H); 8.25 (s, 1H) [M+1] +:
N-N ppm. 234 /
6-Chloro-3-(1-methy1-1H-pyrazol-4-yI)-imidazo[1,2-b]pyridazine 358 1.9 N (CDCI3, stored over MW:
rf.---...
861 molecular sieves): 235.70 /
CIN-N 6 = 7.14 (d, 1H); 7.48 (m, \ S
---1 1H); 7.64 (m, 1H); 8.02 (d, MS
(ES+) 1H); 8.07 (s, 1H); 8.34 (m, [M+1] +:
1H) ppm. 236 =
6-Chloro-3-thiophen-3-yl-imidazo [1,2-b]pyridazine 601 1.10 . e\r:-,N MW:
352 244.69 CI
MS (CI+) 3-(6-Chloro-imidazo[1,2-b]pyridazin -3-yI)-phenylamine 601 1.11 MW:
373 286.72 Cl NMS (CI+) N-(3-(6-Chloro-imidazo[1,2-13]pyrida zin-3-y1)-phenyl]acetamide 602 1.12 e"Nr..1.1.N MW:
147 274.67 Cl N
MS (CI+) _ 6-Chloro-3-(3-nitro-phenyl)-imidazo [1,2-b]pyridazine 602 1.13 MW:
564 278.14 2 2N _11%1 /
CI N
MS (CI+) * CI
6-Chloro-3-(3-chloro-4-methyl-pheny I)-imidazo[1,2-b]pyridazine 603 1.14 (400 MHz, d6-DMS0): MW:
262 8 = 3.87 (s, 3H); 7.49 (d, 1H);
260.68 1 7.62 (m, 1H); 7.66¨ 7.67 (m, ci N 1H); 8.24 ¨ 8.26 (m, 1H); MS
(ES+) ---- = 8.32 (d, 1H); 8.55 (s, 1H) 261; 263 (Cl / 0 ppm. Isotopes) N
6-Chloro-3-(2-methoxy-pyridin-4-yI)-imidazo[1,2-b]pyridazine 603 1.15 (300 MHz, d6-DMS0): MW:
frN
013 8 = 3.89 (s, 3H); 6.96 ¨ TOO
260.68 CI .N=N (m, 1H); 7.38 (d, 1H); 8.24 ¨
8.28 (m, 2H); 8.28 ¨ 8.32 (m, MS (ES+) 1H); 8.82 ¨ 8.83 (m, 1H) 261; 263 (CI
,,r ppm. Isotopes) 6-Chloro-3-(6-methoxy-pyridin-3-yI)-imidazo[1,2-b]pyridazine 602 1.16 (300 MHz, d6-DMS0): MW:
976 6 = 3.84 (s, 6H); 6.58 (t, 1H);
289.72 8 7.32 (d, 2H); 7.43 (d, 1H);
01' 8.30 (d, 1H); 8.40 (s, 1H) MS
(ES+) ppm. 290; 292 (CI
Isotopes) 0\
6-Chloro-3-(3,5-dimethoxy-phenyI)-imidazo[1,2-b]pyridazine 601 1.17 (300 MHz, d6-DMS0):
957 8 = 3.69 (s, 3H); 3.83 (s, 6H);
6 7.38 (d, 1H); 7.40 (s, 2H);
CI -N 8.25 (d, 1H); 8.33 (s, 1H) ppm.
0\
6-Chloro-3-(3,4,5-trimethoxy-phenyI)-imidazo[1,2-b]pyridazine 601 1.18 (400 MHz, d6-DMS0):
957 8 = 7.45 (d, 1H); 7.73 - 7.78 CI (m, 2H); 8.31 (d, 1H); 8.36 -8.39 (m, 1H); 8.46 (m, 2H) F PPm=
F F
6-Chloro-3-(3-trifluoromethyl-phenyI)-imidazo[1,2-blpyridazine 601 1.19 (300 MHz, d6-DMS0):
957 6 = 7.36 - 7.40 (m, 2H); 7.46 0 A )1 / (d, 1H); 7.90- 7.93 (m, 1H);
N
8.02 - 8.05 (m, 1H); 8.18 (s, S 1H); 8.32 (d, 1H); 8.43 (s, 1H) ppm.
' *
3-Benzo[b]thiophen-2-y1-6-chloro-imidazo[1,2-Npyridazine e 601 1.20 (300 MHz, d6-DMS0): MW: \r--N
370 6 = 3.80 (s, 3H); 6.94 - 6.98 259.70 (m, 1H); 7.37 - 7.45 (m, 2H);
CI N 7.63 - 7.66 (m, 2H); 8.26 (d, MS
(ES+) 1H); 8.32 (s, 1H) ppm. 260; 262 (CI
Isotopes) 0\
6-Chloro-3-(3-methoxy-phenyI)-imidazo[1,2-b]pyridazine 601 1.21 (400 MHz, d6-DMS0):
979 8 = 7.36 - 7.38 (m, 1H); 7.43 6CIN ,.N (d, 1H); 7.62 - 7.66 (m, 1H);
8.09 - 8.11 (m, 1H); 8.13 (m, 1H); 8.29 (d, 1H); 8.41 (s, io 0 F 1H) ppm.
6-Chloro-3-(3-trifluoromethoxy-phenyI)-imidazo[1,2-b]pyridazine 602 1.22 (300 MHz, d6-DMS0): MW:
059 5 = 7.45 (d, 1H); 7.77 (d, 1H);
298.56 8.09 (dd, 1H); 8.29 (d, 1H);
-1µ1 8.36 (d, 1H); 8.43 (s, 1H) MS
(ES+) ppm. 298; 300;
302 (Cl II CI Isotopes) CI
6-Chloro-3-(3,4-dichloro-phenyI)-imidazo[1,2-b]pyridazine 602 1.23 (300 MHz, d6-DMS0):
059 8 = 7.42 (d, 1H); 7.55 - 7.61 7 (M, 1H); 8.08 - 8.13 (m, 1H);
Cr 1\1 8.27 - 8.31 (m, 2H); 8.36 (s, 1H) ppm.
lip CI
6-Chloro-3-(3-chloro-4-fluoro-phenyI)-imidazo[1,2-b]pyridazine 602 1.24 (300 MHz, d6-DMS0):
059 8 = 7.45 (d, 1H); 7.70 - 7.75 6 (m, 1H); 7.82 - 7.85 (m, 1H);
CI N 8.31 (d, 1H); 8.41 - 8.45 (m, 2H); 8.51 (m, 1H) ppm.

3-(6-Chloro-imidazo[1,2-b]pyridazin-3-yI)-benzonitrile 603 1.25 (400 MHz, d6-DMS0): MW:
336 = 7.05 - 7.10 (m, 1H); 7.36 263.66 CI (d, 1H); 7.72 - 7.74 (m, 1H);
7.87 - 7.91 (m, 1H); 8.22 - MS (ES+) 8.25 (m, 2H); 10.24 (br s, 1H) 264; 266 (Cl F ppm. Isotopes) OH
4-(6-Chloro-imidazo[1,2-b]pyridazin-3-yI)-2-fluoro-phenol ALJ/TDS
1.26 N MW:
307.76 ) CI N
MS (ES+) Ia 308; 310 (CI
s=o Isotopes) 6-Chloro-3-(3-methanesulfonyl-phenyl)-imidazo[1,2-1Apyridazine 600 1.27 e\ r-ts1/ MW:
073 324.23 4 , \ MS
(El+) Br (3-Bromo-imidazo[1,2-b]pyridazin-6-yl)-(3-pyrrolidin-1-yl-propy1)-amine 6-Chloro-3-naphthalen-2-ylimidazo[1,2-b]pyridazine (Example 1.28) CI
1111*
1.03 g of 6-chloro-3-naphthalen-2-ylimidazo[1,2-b]pyridazine were prepared from 3.5 g (12.52 mmol) of 6-chloro-3-iodoimidazo[1,2-b]pyridazine (Example 1.2) and 2.37 g (13.78 mmol) of 2-naphthylboronic acid (CAS No. 32316-92-0) in analogy to Example 1.4.
1H-NMR (400 MHz, d6-DMS0): 8 = 7.43 (d, 1H); 7.51 ¨ 7.57 (m, 2H); 7.92 ¨ 7.98 (m, 2H); 8.02 ¨ 8.05 (m, 1H); 8.13 ¨ 8.16 (m, 1H); 8.31 (d, 1H); 8.43 (s, 1H);
8.69 (s, 1H) ppm.

ALJ/TDS
Preparation of the final products of the invention:
Method A: (3-phenylimidazor 1,2-14pyridazin-6-y1)-(3-pyrrolidin-1-ylpropy1)-amine (Example 2.0) "N N-CI N
100 mg (0.435 mmol) of 6-chloro-3-phenylimidazo[1,2-b]pyridazine were dissolved in a mixture of 6 ml of tetrahydrofuran and 2 ml of dimethylformamide under argon.
56 mg (0.435 mmol, 1.0 eq.) of 1-(3-aminopropyl)pyrrolidine, 40 mg (0.07 mmol, 0.16 eq.) of bis(dibenzylideneacetone)palladium(0) (Pd2dba3), 27 mg (0.0435 mmol, 0.1 eq.) of rac. 2,2`-bis(diphenylphosphino)-1,1`-binaphthyl (rac-BINAP) and 84 mg io (0.87 mmol, 2 eq.) of sodium tert-butoxide (NaOtBu) were successively added, and the reaction mixture was heated at 80 C for 4 hours.
The reaction mixture was then mixed with ethyl acetate and, after addition of water, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with sat.
is sodium chloride solution and dried over sodium sulfate. After multiple purification on silica gel in the final chromatographic fractionation, 9 mg (6%) of the desired product were isolated in pure form.
1H-NMR (CDCI3, stored over molecular sieves): 6 = 1.8 (m, 4H); 1.88 (m, 2H);
2,55 (m, 4H); 2.68 (t, 2H); 3.51 (m, 2H); 6.19 (s, br. 1H); 6.38 (d, 1H); 7.33 (m, 1H); 7.46 20 (m, 2H); 7.63 (d, 1H); 7.79 (s, 1H); 8.12 (d, 2H) ppm.
MS (ES+): m/z = 322 (100%)([M+Hr.

ALJ/TDS
The following are prepared in an analogous manner:
Table 2:
Mol. weight Example Structure and name of the main isomer 1H-NMR MS (ES+) No. [M+1]
2.1 (CDCI3, stored over molecular sieves): 6 = 1.86 (m, 2H); 2.50 (m, 4H); 2.54 0) (m, 2H); 3.50 (m, 2H); 3.75 (m, 4H); 6.02 (s, br. 1H); 6.41 (d, 1H); 7.46 (m, 2H); 7.67 (3-Morpholin-4-yl-propyI)-(3-phenyl- (d, 1H); 7.80 (s, 1H); 8.12 (d, imidazo[1,2-b]pyridazin-6-yI)-amine 2H) ppm.
2.2 (CDCI3, stored over MW:
molecular sieves): 6 = 1.81 CNNN-N 355.87 (m, 4H); 1.89 (m, 2H); 2.56 (m, 4H); 2.68 (m, 2H); 3.53 MS (ES+) CI (m, 2H); 6.34 (s, br. 1H); 6.39 +:
[3-(3-Chloro-phenyl)-imidazo[1,2-b] (d, 1H); 7.29(m, 1H); 7.38 [M+1]
pyridazin-6-yI]-(3-pyrrolidin-1-yl- (dd, 1H); 7.64 (d, 1H); 7.81 propyI)-amine (s, 1H); 7.95 (m, 1 H); 8.30 (s, 1H) ppm.
2.3 \r.N (CDCI3, stored over MW:
molecular sieves): 6 =1.88 rNNN-N 371.87 (m, 2H); 2.50 (m, 4H); 2.57 oJ
(m, 2H); 3.53 (m, 2H); 3.75 MS (ES+) ci (m, 4H); 6.08 (m, 1H); 6.45 (d, 1H); 7.29(m, 1H); 7.38 [M+1]+:
[3-(3-Chloro-phenyI)-imidazo[1,2-b]
pyridazin-6-y11-(3-morpholin-4-yl- (dd, 1H); 7.67 (d, 1H); 7.82 propyI)-amine (s, 1H); 7.94 (dd, 1H); 8.32 (d, 2H) ppm.
2.4 MW:
-/N 385.90 MS (Cl+) CI

[3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-yI]-methyl-(3-morpholin -4-yl-propyI)-amine ALJ/TDS
2.5(CDCI3, stored over 4,1,õ molecular sieves): = 1.45 y HN N (s, 9H); 2.04 (m, 1H); 2.34 (m, 1H); 3.45-3.60 (m, 3H);
ci 3.77 (m, 1H); 4.46 (m, 1H);
4.65(m, 1H); 6.48 (d, 1H);
3-[3-(3-Chloro-phenyI)-imidazo[1,2- 7.28 (m, 1H); 7.37 (m, 1H);
blpyridazin-6-ylamino]-pyrrolidine- 7.70 (m, 1H); 7.84 (m, 2H);
1-carboxylic acid tert-butyl ester 8.32 (m, 1H) ppm.
2.6N MW:
394.48 NN
NN
MS (ES+) IP [Iv 395 N-{346-(3-Morpholin-4-yl-propylami no)-imidazo[1,2-b]pyridazin-3-y1Fp henyI}-acetamide 2.7 MW:
385.94 MS (ES+) CI
(S)-N*4*-[3-(3-Chloro-phenyh-imida zo[1,2-b]pyridazin-6-yI]-N*1*,N*1*-diethyl-pentane-1,4-diamine 2.8 MW:
385.94 N N
MS (ES+) (R)-N*4*-13-(3-Chloro-pheny1)-imida zo[1,2-b]pyridazin-6-y1]N*1*,N*1*-diethyl-pentane-1,4-diamine 2.9 MW:
413.91 N
ms(c,+) .1,0TNJ 414 * CI

4-[3-(3-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-y11-piperazine-1-carb oxylic acid tert-butyl ester All/TDS
2.10 MW:
0õ0 379.87 -1"s1 N N N
MS (C1+) CI
243-(3-Chloro-pheny1)-imidazo[1,2-lApyridazin-6-ylaminoFethanesulfon ic acid dimethylamide 2.11 rrN(CDCI3, stored over molecular sieves): 6 = 1.09 (t, 6H); 1.85 (m, 2H); 2.43 (s, 3H); 2.53-2.69 (m, 6H); 3.49 CI (m, 2H); 6.40 (d, 1H); 6.76 (m, 1H); 7.39 (d, 1H); 7.62 (d, 2H); 7.75 (s, 1H); 7.93 (m, N'-[3-(3-Chloro-4-methyl-phenyl)-im 1H); 8.01 (m, 1H) ppm.
idazo[1,2-b]pyridazin-6-yli-N,N-die thyl-propane-1,3-diamine / (300 MHz, d6-DMS0): =
2.12 3.03 -3.08 (m, 2H); 3.63 -H 3.70 (m, 5H); 3.73 (s, 6H);
11 1/ 6.65 (d, 1H); 7.15- 7.26 (m, 3H); 7.54 (s, 2H); 7.64 - 7.71 ck (m, 2H); 7.92 (s, 1H); 8.46 -8.48 (m, 1H) ppm.
(2-Pyridin-2-yl-ethyl)13-(3,4,5-trinnethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-y11-amine 2.13 (400 MHz, d6-DMS0): 6 =
N2.58 (s, 3H); 4.58 - 4.60 (m, 2H); 6.86 (d, 1H); 7.39 - 7.40 II H
0 OM 2H); 7.47 - 7.50 (m, 1H);
7.79- 7.86 (m, 3H); 7.99 (s, 1H); 8.09 - 8.12 (m, 1H);
1-(3-{6-[(Pyridin-4-ylmethyp-amino]- 8.49 - 8.50 (m, 2H); 8.67 -imidazo[1,2-b]pyridazin-3-yll-phenyl)- 8.68 (m, 1H) ppm.
ethanone 2.14 (400 MHz, d6-DMS0): 6 =
0.93 (t, 3H); 1.58 - 1.67 (m, 2H); (m, 2H, covered by solvent); 2.61 (s, 3H); 6.70 (d, 1H); 7.09 - 7.11 (m, 1H);
1-[3-(6-Propylamino-imidazo[1,2- 7.55 - 7.59 (m, 1H); 7.73 (d, blpyridazin-3-y1)-phenyl]ethanone 1H); 7.83 - 7.86 (m, 1H);
7.97 (s, 1H); 8.28 -8.31 (m, 1H)_; 8.96 - 8.97 (m, 1H) ALJ/TDS
PPm=
2.15 o . (300 MHz, d6-DMS0): = MW:
1.40- 1.52 (m, 2H); 1.98- 354.41 2.03 (m, 2H); 3.34 - 3.42 (m, MS (ES+) 411 0 2H); 3.78 - 3.90 (m, 9H); 355 6.43 (t, 1H); 6.65 (d, 1H);

[3-(3,5-Dimethoxy-phenyI)-imidazo[1,2- 7.02 - 7.05 (m, 1H); 7.36 (d, b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)- 2H); 7.71 (d, 1H); 7.90 (s, amine 1H) ppm.
2.16 o (300 MHz, d6-DMS0): 8 = MW:
1.38 - 1.52 (m, 2H); 1.98- 310.36 N
2.03 (m, 2H); 3.38 - 3.46 (m, MS (ES+) 2H); 3.73 - 3.91 (m, 3H); 311 6.60 (d, 1H); 6.79- 6.82 (m, OH
4[6-(Tetrahydro-pyran-4-ylannino)-2H); 6.95 - 6.97 (m, 1H);
imidazo[1,2-b]pyridazin-3-y1]-phenol 7.66 - 7.69 (m, 2H); 7.91 -7.94 (m, 2H); 9.54 (s, 1H) ppm.
2.17 o (400 MHz, d6-DMS0): 8 =
1.42 - 1.52 (m, 2H); 1.96 -N
2.01 (m, 2H); 3.34- 3.40 (m, F
2H); 3.78 - 3.90 (m, 3H);
F F 6.70(d, 1H); 7.13 - 7.15 (m, (Tetrahydro-pyran-4-yI)-[3-(3- 1H); 7.60 - 7.67 (m, 2H);
trifluoromethyl-phenyl)-imidazo[1,2- 7.77 (d, 1H); 8.02 (s, 1H);
b]pyridazin-6-y1Famine 8.24 - 8.27 (m, 1H); 8.77 (br s, 1H) ppm.
2.18 o (300 MHz, d6-DMS0): ö =
1.44 - 1.57 (m, 2H); 2.10 -N
2.16 (m, 2H); 3.53- 3.61 (m, 2H); 3.92 - 4.05 (m, 3H);
6.71 (d, 1H); 7.23- 7.25 (m, 1H); 7.28 - 7.39 (m, 2H);
7.76 - 7.81 (m, 2H); 7.94 -(3-Benzo[b]thiophen-2-yl-imidazo[1,2-7.97 (m, 1H); 8.00 (s, 1H);
b]pyridazin-6-y1)-(tetrahydro-pyran-4-y1)-8.05 (br s, 1H) ppm.
amine 2.19 o (400 MHz, d6-DMS0): 8 = MW:
1.40 - 1.50 (m, 2H); 1.96- 325.37 2.00 (m, 2H); 3.39 - 3.45 (m, MS (ES+) /
2H); 3.73- 3.83 (m, 1H); 326 3.85 - 3.89 (m, 5H); 6.66 (d, 1H); 6.90 (d, 1H); 7.06 - 7.07 [3-(6-Methoxy-pyridin-3-y1)-imidazo[1,2- (m, 1H); 7.73 (d, 1H); 7.81 (s, b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)- 1H); 8.37 - 8.39 (dd, 1H) amine ALJ/TDS
8.86(m, 1H) ppm.
2.20 (300 MHz, d6-DMS0): 8 = MW:
1.41 - 1.53 (m, 2H); 2.02 - 325.37 2.06 (m, 2H); 3.41 - 3.49 (m, MS (ES+) /
2H); 3.75 - 3.93 (m, 6H); 326 6.73(d, 1H); 7.20 - 7.22 (m, [3-(2-Methoxy-pyridin-4-yI)-imidazo[1,2- 1H); 7.61 -7.63 (m, 1H);
b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)-7.77 (d, 1H); 7.82 (s, 1H);
amine 8.12 - 8.15 (m, 2H) ppm.
2.21 (400 MHz, d6-DMS0): =
1.39 - 1.48 (m, 2H); 1.97 -H 1.99 (m, 2H); 3.23 (s, 3H);
to 3.48 - 3.53 (m, 2H); 3.82 -s\--3.84 (m, 2H); 3.96 -4.01 (m, [3-(3-Methanesulfonyl-pheny1)-imidazo[1,2- 1H); 6.70 (d, 1H); 7.10 - 7.11 b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)-. (m, 1H); 7.67 - 7.71 (m, 1H);
amine 7.76(d, 1H); 7.81 - 7.83 (m, 1H); 8.02 (s, 1H); 8.29 - 8.31 (m, 1H); 9.00 (m, 1H) ppm.
Method B: [3-(1-methyl-1H-pyrazol-4-yl)imidazotl,2-b]pyridazin-6-ylipyridin-3-ylmethylamine (Example 3.0) cIcN
(rH
ejl /
N-N
N-N
35 mg (0.15 mmol) of 6-chloro-3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-13]pyridazine were introduced into a mixture of 0.67 ml of tetrahydrofuran and 0.33 ml of dimethylformamide under argon. Then 0.5 ml of a 0.45 M solution of pyridin-3-ylmethylamine (0.225 mmol) in toluene was added. Addition of solutions of 1.72 mg of Pd2dba3 (18.8 pmol) and 3.5 mg of rac-BINAP (56.3 pmol) in 0.91 ml of THF
and 31.7 mg of NaOtBu (0.3 mmol) in 0.91 ml of THF was followed by shaking of the reaction mixture at 80 C for 12 h.

ALJ/TDS
The reaction mixture was then mixed with 1 ml of water and 3 ml of ethyl acetate.
The organic phase was separated off and freed of solvent. The crude product obtained in this way was purified by HPLC. 8.7 mg (19%) of the desired product were isolated.
HPLC-MS (analytical) of the purified product Detection: UV = 254 nm; column: Purospher STAR RP18e, 125x4mm, 5 pm (Merck KGaA, Darmstadt); eluent: A: H20/0.1% TFA, B: CH3CN/0.1% TEA, gradient: 5 to 95% B in 10 min; flow rate: 1 ml/min:
Retention time of the product = 3.85 min; MS of the product: m/z = 301 ([M+H]) =
The following are prepared in analogous manner:
Table 3:
HPLC-MSMol. weight/
Retention time Example method MS
(HPLC-Prot. No. Structure and Name of the main isomer (HPLC, UV 254 No. (see MS) nm) [min]
below) [M+11-KE1322- 3.1 A 4.59 001-a 1%11 N
(3-Phenyl-imidazo[1,2-b]pyridazin-6 -yI)-pyridin-3-ylmethyl-amine KE1322- 3.2 A 4.85 002-a 320 N.j.
(3-Imidazol-1-yl-propy1)-(3-phenyl-imidazo[1,2-b]pyridazin-6-y1)-amine KE1322- 3.3 A .7.37 003-a FH
I*
(4-Fluoro-benzyI)-(3-phenyl-imidazo [1,2-b]pyridazin-6-yI)-amine KE1322- 3.4 A 8.36 004-a 307 (r Cyclohexylmethyl-(3-phenyl-imidazo [1,2-b]pyridazin-6-yI)-amine ALJ/TDS
KE1322- 3.5 JZX A 7.49 005-a /
H"
(2,4-Difluoro-benzyI)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yI)-amine KE1322- 3.6 A 5.42 006-a iriT'' NN
.N
[3-(5-Methyl-1 H-pyrazol-4-y1)-propyl]-(3-phenyl-imidazo[1,2-b]pyridazin-6-y1) -amine KE1322- 3.7 H 0 A 4.84 322/
007-a /N--f N
142-(3-Phenyl-imidazo[1,2-13]
pyridazin-6-ylamino)-ethylF
imidazolidin-2-one KE1322- 3.8 A 4.71 009-a 0 1 LN
,1=114/
N N
(2-Morpholin-4-yl-ethyl)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yI)-amine KE1322- 3.9 N A 5.51 010-a Ns1 Al N*1*,N*1*-Diethyl-N*4*-(3-phenyl-imidazo[1,2-b]pyridazin-6-y1)-pentane -1,4-diamine ALJ/TDS
KE1322- 3.10 011-a 324 N,N-Diethyl-N'-(3-phenyl-imidazo [1,2-b]pyridazin-6-yI)-propane-1,3-diamine KE1322- 3.11 A 4.84 012-a 308 NUN
1%11 N
(3-Phenyl-imidazo[1,2-13jpyridazin-6-y1)-(2-pyrrolidin-1-yl-ethyl)-amine KE1322- 3.12 A 5.09 013-a Ii /
1%11 N
CI
[3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-y1Fpyridin-3-ylmethyl-amine KE1322- 3.13 A 5.36 014-a NN /
Nj IP CI
[3-(3-Chloro-phenyI)-imidazo[1,2-b]
pyridazin-6-y1]-(3-imidazol-1-yl-propyI)-amine KE1322- 3.14 A 7.73 015-a /
N N
*
* CI
[3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-y1]-(4-fluoro-benzy1)-amine ALJ/TDS
KE1322- 3.15 016-a fr-N A 8.87 N N.NN
H
* CI
[3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-yl]-cyclohexylmethyl-amine KE1322- 3.16 A 7.93 017-a N N
I. 4 # CI
[3-(3-Chloro-phenyl)-imidazo[1 ,2-h]
pyridazin-6-y1]-(2,4-difluoro-benzy1)-amine KE1322- 3.17 H 0 A 5.25 357/
019-a /NI

N
CI
1-{243-(3-Chloro-pheny1)-imidazo [1,2-14pyridazin-6-ylaminol-ethyl}-imidazolidin-2-one KE1322- 3.18 A 5.87 022-a N.v( N N
* CI
N*4*-[3-(3-Chloro-phenyI)-imidazo [1,2-blpyridazin-6-A-N*1*,N*1*-diethyl-pentane-1,4-diamine KE1322- 3.19 A 5.53 023-a 359 1N., * CI
N'-13-(3-Chloro-phenyl)-imidazo [1,2-b]pyridazin-6-yli-N,N-diethyl-propane-1,3-diamine ALJ/TDS
KE1322- 3.20 A 5.29 024-a CIN

N
N N
* CI
[3-(3-Chloro-phenyl)-imidazo [1,2-b]pyridazin-6-y1]-(2-pyrrolidin-1-yl-ethyl)-amine KE1322- 3.21 N A 4.21 026-a N-N
(3-Imidazol-1-yl-propy1)43-(1-methyl-1H-pyrazol-4-y1)-imidazo [1,2-13]pyridazin-6-y1Famine KE1322- 3.22 A 6.19 027-a N
/
N-N
(4-Fluoro-benzy1)-13-(1-methyl-1H-pyrazol-4-y1)-imidazo[1,2-13]-pyridazin-6-y1Famine KE1322- 3.23 N A 6.97 028-a N-N
Cyclohexylmethy1-13-(1-methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-y1Famine LJ/TDS
KE1322- 3.24 N A 6.17 029-a H"

N-N
(2,4-Difluoro-benzy1)-[3-(1-methy1-1H-pyrazol-4-y1)-imidazo[1,2-13]-pyridazin-6-y1Famine KE1322- 3.25 A 4.64 030-a337 ,114ki [3-(1-Methy1-1H-pyrazol-4-y1)-imidazo-[I,2-13]pyridazin-6-y1H3-(5-methyl-1H-pyrazol-4-y1)-propylFamine KE1322- 3.26 H 0 A 4.09 326/
031-a //4--r N-N
14243-(I -Methyl-I H-pyrazol-4-y1)-imidazo[I ,2-b]pyridazin-6-ylam ino]-ethyll-im idazolidin-2-one KE1322- 3.27 A 3.91 033-a 0 1 =
=
/ I
N-N
[3-(1-Methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-y1]-(2-morpholin-4-yl-ethyl)-amine ALJ/TDS
KE1322- 3.28A 4.6 034-a ===)N,,..,/-,J,ilf- 3 Is NN( / I
N-N
N*1*,N*1*-Diethyl-N*4*-[3-(1-methyl -1H-pyrazol-4-y1)-imidazo[1,2-13]-pyridazin-6-01-pentane-1,4-diamine KE1322- 3.29 A 4.29 035-a / I
14-1µ1 N,N-Diethyl-N'-[3-(1-methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-yli-propane-1,3-diamine KE1322- 3.30 A 4.11 036-a 312 /
N-N
[3-(1-Methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-y1F
(2-nvrrolidin-1-1/1-ethyll-amine KE1322- 3.31 A 4.55 037-a N
ti N
S
Pyridin-3-ylmethyl-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yI)-amine KE1322- 3.32 N A 4.8 038-a 325 S
(3-Imidazol-1-yl-propy1)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yI)-amine ALJ/TDS
' KE1322- 3.33 -,r..,-.N A 7.29 039-a A, ,t:Iti = HI'll N --.._ F \ S
(4-Fluoro-benzyI)-(3-thiophen-3-yl-imidazo[1,2-131pyridazin-6-y1)-amine KE1322- 3.34 ,,Cr.N A 8.26 312/
040-a N....t . O'N Isl-i H .....
\ S
Cyclohexylmethyl-(3-thiophen-3-yl-imidazo(1,2-131pyridazin-6-y1)-amine KE1322- 3.35N A 7.37 ) F fr-041-a N N..Ntl F \ S
(2,4-Difluoro-benzyI)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yI)-amine KE1322- 3.36 i.....1,N A 5.31 042-a ,1?%Iti N N
isl-- ' H \ S
[345-Methy1-1H-pyrazol-4-y1)-propyl]-(3-thiophen-3-yl-imidazo-, [1,2-b]pyridazin-6-yI)-amine , ' KE1322- 3.37 H 0 . A 4.71 328/
043-a /N--f \.....N.) r-Th...- ..,N
NN"Isi".ti A, \ s 1-[2-(3-Thiophen-3-yl-imidazo-[1,2-1Apyridazin-6-ylamino)-ethyl]-imidazolidin-2-one ALJ/TDS
' KE1322- 3.38A 4.64 045-a 0-Th 1õN.)r....N
CNN-N...t H-...._ \ S
(2-Morpholin-4-yl-ethyl)-(3-thiophen-3-yl-imidazo[1,2-13]
pyridazin-6-yI)-amine KE1322- 3.39A 5.42 046-a .%) Kr-,,,. ,N

.N.,^J., A- A4-1 N NN( H -, \ S
N*1*,N*1*-Diethyl-N*4*-(34hiophen-3-yl-imidazo[1,2-13]pyridazin-6-y1)-pentane-1,4-diamine KE1322- 3.40N rj A 4.92 047-a N r.:.,...-11-..t -=N N-) 1 H ...., \ S
N,N-Diethyl-W-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yI)-propane-1,3-diamine KE1322- 3.41 A 4.74 048-a c-IN riy...N
Cfsl-N-Nti , 1 \ S
(2-Pyrrolidin-1-yl-ethyl)-(3-thiophen-3-yl-imidazo[1,2-13]-, pyridazin-6-yI)-amine HU6083- 3.42ri...,,.. N B 7.99 359.43 /

N -N,N / 360.06/
I
*9 [3-(3-Methoxy-phenyl)-imidazo[1,2-b ]pyridazin-6-y1j-methyl-(2-pyridin-2-yl-etbyI)-amine ALJTIDS
=
HU6083- 3.43 9.42 413.40 /

413.99 '*O
r F
Methyl-(2-pyridin-2-yl-ethyl)-[3-(3 -trifluoromethoxy-phenyl)-imidazo[1 ,2-1Apyridazin-6-01-amine HU6083- 3.44 N B 10.03 398.30 /

397.94 CI
CI
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-1Apyridazin-6-yli-methyl-(2-pyrid in-2-yl-ethyl)-amine HU6083- 3.45 9.16 381.84 /

N NN381.95 CI
[3-(3-Chloro-4-fluoro-phenyl)-imida zo[1,2-1Apyridazin-6-y1Fmethyl-(2-pyridin-2-yl-ethyl)-amine HU6083- 3.46 9.32 379.46 /

380.02 AIL
Methyl-(3-naphthalen-2-yl-imidazo[1 ,2-13]pyridazin-6-y1)-(2-pyridin-2-y 1-ethyl)-amine ALJ/TDS
HU6083- 3.47 7.47 345.40 / 346.

141 N N"

[3-(3-Methoxy-phenyI)-imidazo[1,2-b ]pyridazin-6-yI]-(2-pyridin-2-yl-et hyl)-amine HU6083- 3.48N B 9.21 384.27 /
N NNN 012 ONõ/- f:Nr-/
383.94 CI
CI
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-14pyridazin-6-y1]-(2-pyridin-2-y1 -ethyl)-amine HU6083- 3.49 7.30 340.39 /

N NN341.06 3-[6-(2-Pyridin-2-yl-ethylamino)-im idazo[1,2-b]pyridazin-3-yq-benzoni bile HU6083- 3.50f r N 8.84 363.85 /
) N
363.97 [3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-y1]-(2-(6-methyl-pyridi n-2-y1)-ethyl]-amine ALJ/TDS
=
HU6083- 3.51 knõ:õ.-N 9.24 413.40/

413.99 = 0 A-F
F F
[2-(6-Methyl-pyridin-2-y1)-ethyl]-[
3-(3-trifluoromethoxy-phenyl)-imida zo[1,2-131pyridazin-6-y1Famine HU6083- 3.529.15 379.46/
I n N

N
380.02 [2-(6-Methyl-pyridin-2-y1)-ethyl]-( 3-naphthalen-2-yl-imidazo[1,2-b]pyr idazin-6-yI)-amine HU6083- 3.53 B 9.76 398.30 /
036 397.94 ,N
N N N
= CI
CI
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-b]pyridazin-6-yI]-[2-(4-methyl-py ridin-2-y1)-ethyl]amine HU6083- 3.54 B 9.15 379.46 /

380.02 N N
[2-(4-Methyl-pyridin-2-y1)-ethyl]-( 3-naphthalen-2-yl-imidazo[1,2-13]pyr idazin-6-yI)-amine ALJ/TDS
HU6083- 3.55 9.36 413.40I

N 14,N 413.93 F F
[2-(3-Methyl-pyridin-2-y1)-ethyl]-[
3-(3-trifluoromethoxy-phenyl)-imida zo(1,2-b]pyridazin-6-y1]-amine HU6108- 3.56 N B 8.13 359.43 /
I

N
N NN359.17 [3-(3-Methoxy-pheny1)-imidazo[1,2-b jpyridazin-6-y1]-[2-(5-methyl-pyrid in-2-y1)-ethyl]-amine HU6108- 3.57 9.49 413.40/

413.15 F
[2-(5-Methyl-pyridin-2-y1)-ethyl]-[
3-(3-trifluoromethoxy-phenyl)-imida zo[1,2-b]pyridazin-6-y1Famine HU6108- 3.58 10.11 398.30/

397.94 CI
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-b]pyridazin-6-y1]-(2-(5-methyl-py ridin-2-y1)-ethyl]amine ALJ/TDS
=
HU6108- 3.59 9.24 381.84/

C)\/ /
381.12 HU6108- 3.60 N B 10.16 398.30I
068cCX 397.09 =I
NN""
= CI
CI
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-b]pyridazin-6-y1H2-(3-methyl-py ridin-2-y1)-ethyl]amine HU6083- 3.61 N B 9.79 398.30 /

397.94 ci CI
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-1Apyridazin-6-y1H2-(6-methyl-py ridin-2-y1)-ethyl]amine HU6083- 3.62 7.62 350.81 /

C:NLN N..N351.01 =
CI
[3-(3-Chloro-phenyI)-imidazo[1,2-b]
pyridazin-6-yI]-(2-pyrazin-2-yl-eth yI)-amine ALJ/TDS
=
HU6083- 3.63 6.88 346.39 /

347.03 N

[3-(3-Methoxy-phenyI)-imidazo[1,2-b ]pyridazin-6-yI]-(2-pyrazin-2-yl-et hyl)-amine HU6083- 3.64 7.79 368.80 /

368.92 CI
(3-(3-Chloro-4-fluoro-phenyl)-imida zo(1,2-b]pyridazin-6-yI]-(2-pyrazin -2-yl-ethyl)-amine HU6083- 3.65 8.01 366.43 /
031N N N4 ,11 /
366.99 (3-Naphthalen-2-yl-imidazo[1,2-b]py ridazin-6-yI)-(2-pyrazin-2-yl-ethyl )-amine HU6083- 3.66 B 8.78 363.85 /
! 033 363.97 N
CI
[3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-yIH2-(4-methyl-pyridi n-2-y1)-ethylFamine SRG/US/53343 ¨ 60 ¨
ALJ/TDS
HU6083¨ 3.67 B 9.19 413.40/
035 rreN
413.99 N N
=0 FF
[2-(4-Methyl-pyridin-2-y1)-ethyl]
3-(3-trifluoromethoxy-phenyl)-imida zo[1,2-b]pyridazin-6-y1Famine r HU6083¨ 3.68 B 8.92 381.84/

381.95 .14 /
N N
'CI
[3-(3-Chloro-4-fluoro-phenyl)-imida zo[1,2-b]pyridazin-6-y1]-(2-(4-meth yl-pyridin-2-yI)-ethyl]-amine HU6083¨ 3.69 7.90 338.80 /

NN N / 339.00 CI
[3-(3-Chloro-phenyI)-imidazo[1,2-b]
pyridazin-6-y1]-(2-pyrazol-1-yl-eth yI)-amine HU6083- 3.70 N B 7.15 334.38/
r 050 335.02 [3-(3-Methoxy-phenyI)-imidazo[1,2-b ]pyridazin-6-y1]-(2-pyrazol-1-yl-et hyl)-amine ALJ/TDS
HU6083- 3.71 8.37 388.35 /

338.95 N N
*0 A¨F
F F
(2-Pyrazol-1-yl-ethyl)-(3-(3-triflu oromethoxy-phenyI)-imidazo[1,2-b]py ridazin-6-yI]-amine HU6083- 3.72 8.66 373.25 /
052 N" 114 /
372.90 N N
= CI
CI
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-13]pyridazin-6-y1]-(2-pyrazol-1-y1 -ethyl)-amine HU6083- 3.73 6.86 329.37/

330.02 N
3-[6-(2-Pyrazol-1-yl-ethylamino)-im idazo[1,2-13]pyridazin-3-0]-benzoni trile HU6083- 3.74 8.04 356.79 /

N N N"
356.98 'CI
[3-(3-Chloro-4-fluoro-phenyl)-imida zo[1,2-1Apyridazin-6-y1]-(2-pyrazol -1-yl-ethyl)-amine ALJ/TDS
HU6083- 3.75 8.22 354.42 /

N
335.05 N N
V14-1, (3-Naphthalen-2-yl-imidazo[1,2-b]py ridazin-6-y1)-(2-pyrazol-1-yl-ethyl )-amine HU6108- 3.76 B 7.98 402.38/

N N N
402.14 A¨F
F F
[2-(I -Methyl-1 H-imidazol-4-y1)-ethy 1]-[3-(3-trifluoromethoxy-phenyl) midazo[1,2-1Apyridazin-6-yli-amine HU6108- 3.77 B 6.65 343.39/

343.15 N
= N
34642-(I -Methyl-1 H-imidazol-4-y1) -ethylaminoi-imidazo[1,2-b]pyridazi n-3-y1}-benzonitrile HU6108- 3.78 B 7.75 368.44 /

N
368.18 [2-(I -Methyl-I H-imidazol-4-y1)-ethy 1]-(3-naphthalen-2-yl-imidazo[1,2-b ]pyridazin-6-y1)-amine SG26724- 3.79Nf-2: e\r.N 6.89 339.79 /
N

339.10 CI
[3-(3-Chloro-phenyI)-imidazo[1,2-b]
pyridazin-6-y1]-(241,2,41triazol-1 -yl-ethyl)-amine SG26724- 3.80 9.38 363.85 /

363.13 CI
[3-(3-Chloro-pheny1)-imidazo[1,2-b]
pyridazin-611]-methyl-(2-pyridin-2 -yl-ethyl)-amine Description of the HPLC-MS analysis conditions for the examples listed in Table 3:
HPLC-MS method A: detection: UV = 254 nm; column: Purospher STAR RP18e, 125x4nrim, 5 pm (Merck KGaA, Darmstadt); eluent: A: H20/0.1 /0 TFA, B:
CH3CN/0.1% TFA, gradient: 5 to 95% B in 10 min; flow rate: 1 ml/min:
HPLC-MS method B: detection: UV = 254 nm; column XBridge C18, RP18e, 150x4.8 mm, 5 pm (Waters); gradient 5-95% acetonitrile (0.1% NH4OH) in water (0.1% NH4OH/NH4HCO3) (10 min.); flow rate 1.0 ml/min.
Method C: (416-(2-hydroxyethylamino)imidazo[1,244pyridazin-3-yliphenol (Example 4.0) fN
,.N
HON N N
Br OH

ALJ/TDS
85 mg (0.33 mmol) of 2-(3-bromoimidazo[1,2-b]pyridazin-6-ylamino)ethanol (Example 1.5), 69 mg (0.5 mmol) of 4-hydroxybenzene boronic acid and 76 mg (0.066 mmol) of tetrakis(triphenylphosphine)palladium(0) were mixed under argon with 3.4 ml of dimethyl glycol and 2 ml of an aqueous NaOH solution (a stock solution of 190 mg of NaOH in 10 ml of water). The mixture was stirred at 90 C
for 19 hours. After cooling, the mixture was diluted with sat. NaCI solution and extracted 2x with ethyl acetate. The combined organic phases were washed with sat. NaCI
solution, filtered through a silicone filter (from Whatman) and concentrated.
The resulting crude product was recrystallized from methanol. 40 mg of the desired 113 product are obtained.
1H-NMR (400 MHz; d6-DMS0): 6 = 3.30 - 3.31 (m, 2H, covered by solvent); 3.61 ¨

3.62 (m, 2H); 4.74 (m, 1H); 6.66 (d, 1H); 6.81 (d, 2H); 6.94 ¨ 6.96 (m, 1H);
7.64 ¨
7.67 (m, 2H); 7.93 (d, 2H); 9.57 (br s, 1H) ppm.
MS (ESI+): m/z = 271 ([M-FH]+). [mol. weight = 270.29].

ALJ/TDS
The following are prepared in an analogous manner:
Table 4 Mol. weight Example Structure and Name of the main isomers 1H-NMR
No. MS (ES+) 4.1 'NMW 284.32 õN

HN N MS (ES+):
[M+1]+ 285 OH
OH
4164(R)-2-Hydroxy-1-methyl-ethylamino)-imidazo[1,2-b]pyridazin-3-y11-phenol 4.2 MW 314.35 ,.1s1 HN N MS (ES+):
104 0 [M+1]4 315 OH
OH
4464(R)-2-Hydroxy-1-methyl-ethylannino)-imidazo[1,2-b]pyridazin-3-yI]-2-methoxy-phenol 4.3 rN

MW:
332.38 MS (ES+) ''s:21 2-[3-(4-Methanesuffonyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylaminol-ethanol 4.4 NN MW:
HO
N N 389.48 MS (ES+) /
HN
N-tert-Butyl-416-(2-hydroxy-ethylamino)-imidazo[1,2-1D]pyridazin-3-y11-ALJ/TDS
benzenesulfonamide 4.5 er-N MW:
347.40 MS (ES+) .%
,..,, NH 348 1.1 S

N-1446-(2-Hydroxy-ethylamino)-imidazo[1,2-b]pyridazin-3-y1]-pheny1}-methanesulfonamide 4.6 MW:
389.48 =MS (ES+) S--N
H

N-tert-Buty1-3-[6-(2-hydroxy-ethylamino)-imidazo[1,2-b]pyridazin-3-y1]-benzenesulfonamide 4.7 MW:
332.38 MS (ESI+) iho 2-[3-(3-Methanesulfonyl-phenyI)-imidazo[1,2-b]pyridazin-6-ylaminoFethanol _ 4.8 MW:
/ 300.38 MS (ESI+) s 243-(3-Methylsulfanyl-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFethanol 4.9 (300 MHz; 1:16-DMS0): 6 = MW:
2.93 - 2.98 (m, 2H); 3.49 -N 354.42 N N 3.56 (m, 2H); 6.39 - 6.40 (m, 1H); 6.61 (d, 1H); 7.15 - 7.19 (m, 1H); 7.24 - 7.28 (m, 1H);
7.34 - 7.36 (m, 1H); 7.43 (d, 1H); 7.64 - 7.68 (m, 1H);
[3-(1H-Indo1-5-y1)-imidazo[1,2-b]pyridazin-7.70 (d, 1H); 7.74 (s, 1H);
7.76 - 7.79 (m, 1H); 8.39 -6-y1]-(2-pyridin-3-yl-ethyl)-amine 8.41 (m, 2H); 8.50 - 8.51 (m, 1H); 11.16(s, 1H) ppm.

ALJ/TDS
4.10 (400 MHz; d6-DMS0): = MW:
2.94 - 2.98 (m, 2H); 3.55 N N 3.60 (m, 2H); 6.65 (d, 1H); 321.41 7.19 - 7.22 (m, 1H); 7.28 S 7.31 (m, 1H); 7.63 - 7.65 (m, 1H); 7.67 - 7.68 (m, 1H);
(2-Pyridin-3-yl-ethyl)-(3-thiophen-3-yl- 7.70 - 7.74 (m, 2H); 7.85 (s, imidazo[1,2-Npyridazin-6-y1)-amine 1H); 8.32 - 8.33 (m, 1H);
8.39 - 8.40 (m, 1H); 8.48 -8.49(m, 1H) ppm.
4.11(400 MHz; d6-DMS0): 5 = MW:
XN/ 2.92 - 2.96 (m, 2H); 3.50 -N = 333.37 N N 3.55 (m, 2H); 6.69 (d, 1H);
7.09 - 7.13 (m, 1H); 7.27 -7.30 (m 2H). 7.42 - 7.48 (m, 1H); 7.65 - 7.68 (m, 1H);
[3-(3-Fluoro-pheny1)-imidazo[1,2-7.75 (d, 1H); 7.96 (s, 1H);
, b]pyridazin-6-y1]-(2-pyridin-3-yl-ethyl)-7.97 - 7.99 (m 1H); 8.09 -8.13 (m, 1H); 8.38 - 8.40 (m, amine 1H); 8.47 - 8.48 (m, 1H) ppm.
The following are prepared in an analogous manner:
Table 5:
Retention time Mol. weight/
Char Example (HPLC, UV MS (HPLC-, No. No. Structure and Name of the main isomer 254 nm) [min]. MS) , 229_0 5.0 _________________ r:rri 11 5_0 N N N

IPAL
365.44 1114, (3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-pyridin-2-yl-ethyl)-amine ALJ/TDS
229_0 5.1 115_0 /
N N N

349.82 Cl [3-(4-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-yI]-(2-pyridin-2-yl-eth yI)-amine 229_0 5.2 115_0 N N N

343.43 [3-(3,4-Dimethyl-phenyl)-imidazo[1, 2-b]pyridazin-6-y1]-(2-pyridin-2-y1 -ethyl)-amine 229_0 5.3 115_0 FXF
399.37 . F
(2-Pyridin-2-yl-ethyl)3-(3-trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-y1]-amine 229_0 5.4 231_0 367.81 [3-(3-Chloro-4-fluoro-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-(2-pyridin-3-yl-ethyl)-amine 229_0 5.5 115_0 349.82 It CI
[3-(3-Chloro-pheny1)-imidazo[1,2-13]pyridazin-6-y1]-(2-pyridin-211-ethyl)-amine ALJ/TDS
229_0 5.6 231_0 349.82 [3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yI]-(2-pyridin-3-yl-eth yI)-amine 229_0 5.7 115_0 = F
383.38 (2-Pyridin-2-yl-ethy1)13-(3-trifluoromethyl-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-amine 229_0 5.8 i 115_0 333.37 F
[3-(3-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-2-yl-ethyl)-amine 229_0 5.9 115_0 = 333.37 [3-(4-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(2-1 pyridin-2-yl-ethyl)-amine ! 229_0 5.10 115_0 0111*

335.43 [3-(4-Methyl-thiophen-2-yI)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-2-yl-ethyl)-amine ALJ/TDS
229_0 5.11 240_0 360.82 443-(3-Chloro-4-fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol 229_0 5.12 115_4 110 o 357.42 1-{3-[6-(2-Pyridin-2-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenylyethanone 229_0 5.13 115_6 488 H0, /
408.48 N-{3-[6-(2-Pyridin-2-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-ylypheny1}-methanesulfonannide 229_0 5.14 115_0 /

340.39 \\
4-[6-(2-Pyridin-2-yl-ethylarnino)-imidazo[1,2-Npyridazin-3-A-benzonitrile 229_0 5.15 115_4 329.41 (2-Pyridin-2-yl-ethyl)-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-yI)-amine ALJ/TDS
229_0 5.16 115_0 1 315.38 (3-Phenyl-imidazo[1,2-b]pyridazin-6-0)-(2-pyridin-2-ykethyl)-amine 229_0 5.17 115_0 I /

365.44 (3-Naphthalen-1-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-pyridin-2-yl-ethyl)-amine 229_0 5.18 115_0 I /

/ =
355.40 (3-Benzofuran-2-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-pyridin-2-yl-ethyl)-amine 229_0 5.19 115_0 367.81 =F
[3-(3-Chloro-4-fluoro-phenyI)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-2-ykethyl)-amine 229_0 5.20 115_0 371.47 (3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-, y1)-(2-pyridin-2-0-ethyl)-arnine ALSTDS
229_0 5.21 115_0 359.39 oJ
(3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-pyridin-2-yl-ethyl)-amine 229_0 5.22 115_0 Ii I
WNVN

345.40 /o [3-(4-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-2-yl-ethyl)-amine 229_0 5.23 2310_ ,1\1 N N

405.46 o /o (2-Pyridin-3-yl-ethy1)13-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.24 N
231_0 H =
333.37 [3-(4-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-3-yl-ethyl)-amine 229_0 5.25 ¨

359.39 o (3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-blpyridazin-6-y1)-ALJ/TDS
(2-pyridin-3-yl-ethyl)-amine 229_0 5.26 N
231_0 345.40 [3-(4-Methoxy-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-(2-pyridin-3-yl-ethyl)-amine 229_0 5.27 231_0 S 335.43 [3-(4-Methyl-thiophen-2-y1)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-3-yl-ethyl)-amine 229_0 5.28 231_0 355.40 41Ik (3-Benzofuran-2-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-.
pyridin-3-yl-ethyl)-amine i 229_0 5.29 ' 231 0 N
N N
.057 111, 365.44 (3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-pyridin-3-yl-ethyl)-amine ALJ/TDS
229_0 5.30 N

S
371.47 (3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-pyridin-3-yl-ethyl)-amine 229_0 5.31 r/. N
231_0 N

= 315.38 (3-Phenyl-imidazo[1,2-b]pyridazin-6-y1)-(2-pyridin-3-yl-ethyl)-amine 229_0 5.32 N
231_0 Na N

349.82 [3-(4-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-3-yl-ethyl)-amine 229_0 5.33 231_0 N N

= 340.39 4-[6-(2-Pyridin-3-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-y1Fbenzonitrile 229_0 5.34 231_0 F
383.38 F F
(2-Pyridin-3-yl-ethy1)43-(3-trifluoromethyl-pheny1)-imidazo[1,2-b]pyridazin-6-01-amine ALUTDS
229_0 5.35 231_7 319.37 fl\IN
[3-(1-Methy1-1H-pyrazol-3-y1)-imidazo[1,2-b]pyridazin-6-y1]-(2-pyridin-3-yl-ethyl)-amine 229_0 5.36 Ntj 231_4 = 321.41/320 0.67 (negative S
mode) (2-Pyridin-3-yl-ethyl)-(3-thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yI)-am me 229_0 5.37 231_6 =====, N N

= 11 408.48 N-(3-[6-(2-Pyridin-3-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenylymethanesulfonamide 229_0 5.38 144_0 ,1=1 0:)HN N
308.32 111\
[3-(4-Fluoro-pheny1)-imidazo[1,2-1Apyridazin-6-y11-furan-2-ylmethyl-amine 229_0 5.39 144_0 290.33 Furan-2-ylmethyl-(3-phenyl-imidazo[1,2-1Apyridazin-6-y1)-amine ALJ/TDS
229_0 5.40 144_0 0:HN N
320.35 Furan-2-ylmethy143-(4-methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-yll-amine 229_0 5.41 144_0 ,N

329.36 Furan-2-ylmethyl-[3-(1H-indol-5-y1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.42 144_0 \CrNH N-333.39 N/
[3-(3-Dimethylamino-phenyI)-imidazo[1,2-b]pyridazin-6-yll-furan-2-ylmethyl-amine , 229_0 5.43 1144_4 /

\ H
320.35 411P 0\
Furan-2-ylmethyl-[3-(3-methoxy-phenyI)-imidazo[1,2-bipyridazin-6-y1]-amine 229_0 5.44 144_0 ji CrN
081 o H
347.38 o N-(3-{6-[(Furan-2-y1methyl)-amino]-imidazo[1,2-LJ/TDS
b]pyridazin-3-y1}-phenyl)-acetamide 229_0 5.45 144_0 N-291 \ 0 H
320.35 OH
(3-{61(Furan-2-ylmethyl)-aminoHmidazo[1,2-Npyridazin-3-y1}-pheny1)-methanol 229_0 5.46 1144_0 306.32 OH
4-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yI}-phenol 229_0 5.47 144_0 \ 0 H 306.32 = OH
3-{6-[(Furan-2-ylmethyl)-aminoHmidazo[1,2-b]pyridazin-3-yI}-phenol 229_0 5.48 e\r--N
144_0 Cr N N-1347 o H
o 333.35 3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yI}-benzamide ! 229_0 5.49 ' 144_6 488 \ 0 H
383.43 o--7/
N-(3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-blpyridazin-3-yI}-phenyl)-methanesulfonamide ALJ/TDS
229_0 5.50 144_0 \ 0 H
336.35 o\
OH
4-{6-[(Furan-2-ylmethyl)-aminol-imidazo[1,2-b]pyridazin-3-y1}-2-methoxy-phenol 229_0 5.51 rj\r-N
144_4 Cr-N N-145 o H
332.36 1-(3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-y1}-pheny1)-ethanone 229_0 5.52 144_0 OrHN N
321.34 Furan-2-ylmethy143-(6-methoxy-pyridin-3-y1)-imidazo[1,2-blpyridazin-6-y1]-amine 229_0 5.53 1144_0 291.31 Furan-2-ylmethyl-(3-pyridin-3-yl-imidazo[1,2-b]pyridazin-6-yI)-amine 229_0 5.54 144_0 321.34 ALJ/TDS
Furan-2-yInnethy143-(5-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-yli-amine 229_0 5.55 144_0 OrHN N
291.31 Furan-2-ylmethyl-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yI)-amine 229_0 5.56 N
146_0 S
366.44 [3-(3,4-Dimethoxy-phenyI)-imidazo[1,2-b]pyridazin-6-ylFthiophen-2-ylmethyl-amine 229_0 5.57 146_0 S
396.47 '0 Thiophen-2-ylmethy143-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.58 146_4 N
INJ"
145 s H o 348.43 =
1-(3-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-01-phenyl)-ethanone ALJ/TDS
229_0 5.59 146_0 N

322.39 = OH
3-(6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yI}-phenol 229_0 5.60 146_0 ,N
Cy.N N-337.41 [3-(5-Methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y1]-thiophen-2-ylmethyl-amine 229_0 5.61 146_0 S
336.42 HO
(4-(6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yll-pheny1)-methanol 229_0 5.62 146_0 192 s H
o 393.47 OH
N-(2-Hydroxy-ethyl)-3-{6-[(thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-y1}-benzamide 229_0 5.63 146_0 \S H
S
326.45 [3-(4-Methyl-thiophen-2-yI)-imidazo[1,2-b]pyridazin-6-ALJ/TDS
ylj-thiophen-2-ylmethyl-amine 229_0 5.64 146_4 S 1.02 312.42/314 S
(3-Thiophen-2-yl-im idazo[1,2-b]pyridazin-6-yI)-thiophen-2-ylm ethyl-am ine 229_0 5.65 146_0 \S H 312.42 S
(3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-y1)-thiophen-2-ylmethyl-amine 229_0 5.66 146_0 CisHN N
337.41 [3-(6-Methoxy-pyridin-3-y1)-imidazo[1,2-1Apyridazin-6-ylphiophen-2-ylmethyl-amine 229_U 5.67 146_0 N
. 204 = a 345.43 [3-(1H-Indo1-5-y9-imidazo[1,2-13]pyridazin-6-yli-thiophen-2-ylmethyl-amine ALJ/TDS
229_0 5.68 146_0 N
135 s H
349.46 N/
[3-(3-Dinnethylamino-phenyl)-innidazo[1,2-b]pyridazin-6-yli-thiophen-2-ylmethyl-amine 229_0 5.69 146_0 324.38 [3-(4-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y11-thiophen-2-ylmethyl-amine 229_0 5.70 146_7 H
310.38 \N,NN
[3-(1-Methy1-1H-pyrazol-4-y1)-innidazo[1,2-13]pyridazin-6-y11-thiophen-2-ylmethyl-amine 229_0 5.71 146_0 CH
307.38 (3-Pyridin-3-yl-imidazo[1,2-b]pyridazin-6-y1)-thiophen-2-ylmethyl-amine 229_0 5.72 363.44 o N-(346-[(Thiophen-2-ylmethy1)-amino]-imidazo[1,2-b]pyridazin-3-y1}-pheny1)-acetannide ALJ/TDS
229_0 5.73 146_4 N

s H 1.01 336.42/338 = o\
[3-(3-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-thiophen-2-ylmethyl-amine 229_0 5.74 146_0 S
322.39 OH
4-{6-[(Thiophen-2-yInnethyl)-amino]-imidazo[1,2-b]pyridazin-3-yI}-phenol 229_0 5.75 146_0 OSN N
307.38 (3-Pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yI)-thiophen-2-ylmethyl-amine 229_0 5.76 146_0 s =
0\
352.42 OH
2-Methoxy-4-{6-Rthiophen-2-ylmethyl)-aminol-imidazo[1,2-b]pyridazin-3-y1}-phenol 229_0 5.77 146_0 s H
o 349.42 3-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-1Apyridazin-3-y1}-benzamide 229_0 5.78 146_6 N N
488 s H
399.50 o=s--_.
//
N-(3-{6-[(Thiophen-2-ylmethyl)--amino]-imidazo[1,2-Npyridazin-3-y1}-phenyl)-methanesulfonamide 229_0 5.79 146_0 N

350.40 OH

4-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yI}-benzoic acid 229_0 5.80 fr-N
237_4 ,N
N

N2 0.62 331.38/332 IF 0\
[3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-y1F
pyridin-4-ylmethyl-amine 229_0 5.81 237_0 tN /
/%1 168 ii I H
N

4111p 85.35.
Pyridin-4-ylmethy143-(3-trifluoromethoxy-phenyl)-imidazo[1,2-1Apyridazin-6-y11-amine 229_0 5.82 frN
237_0 ,N
N-N 335.80 = a [3-(3-Chloro-pheny1)-imidazo[1,2-13]pyridazin-6-y1]-pyridin-4-ylmethyl-amine ALJ/TDS
229_0 5.83 237_0 õN

F
369.35 F F
Pyridin-4-ylmethyl-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-13]pyridazin-6-y1Famine 229_0 5.84 237_0 164 1jNN

H
N
353.79 CI
[3-(3-Chloro-4-fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-pyridin-4-ylmethyl-amine 229_0 5.85 237_0 N N

341.37 (3-Benzofuran-2-yl-im idazo[1,2-b]pyridazin-6-yI)-pyriden-4-ylmethyl-am me 229_0 5.86 237_0 õ.4 N

N
41, 329.41 [3-(3,4-Dimethyl-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-pyridin-4-ylmethyl-amine 229_0 5.87 = 237_4 , 139 N N-H
N
0.66 315.38/316 Pyridin-4-ylmethyl-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-yI)-amine 229_0 5.88 237_4 0.61 307.38/308 S
Pyridin-4-ylmethyl-(3-thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yI)-amine 229_0 5.89 237_0 N

301.35 (3-Phenyl-imidazo[1,2-lo]pyridazin-6-y1)-pyridin-4-ylmethyl-amine 229_0 5.90 ,N
N N-345.36 = 0 (3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-y1)-pyridin-4-ylmethyl-amine 229_0 5.91 237_0 057 µ11 N
351.41' (3-Naphthalen-2-yl-imidazo[1,2-1Apyridazin-6-y1)-pyridin-4-ylmethyl-amine 229_0 5.92 N
237_0 076 rN N
357.44 S

LJ/TD S
(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yI)-pyridin-4-ylmethyl-amine 229_0 5.93 237_0 N
160 rN N
335.80 CI
[3-(4-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-pyridin-4-ylmethyl-amine 229_0 5.94 237_0 N

NJ
380.25 = Br [3-(3-Bromo-pheny1)-imidazo[1,2-1Apyridazin-6-yll-pyridin-4-ylmethyl-amine 229_0 5.95 237_6 N

}N%
488 r N
FN
394.46 ¨s, N-(3-{6-[(Pyridin-4-ylmethyp-amino]-imidazo[1,2-Npyridazin-3-y1}-phenylymethanesulfonamide 229_0 5.96 237_4 319.34 [3-(2-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-pyridin-4-ylmethyl-amine 229_4 5.97 007_0 391.43 411 \

ALJ/TDS
Pyridin-2-ylmethyl-[3-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y11-annine 229_4 5.98 ji 007_0 = 319.34 [3-(4-Fluoro-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-pyridin-2-ylmethyl-amine 229_4 5.99 N
007_0 N N

341.37 (3-Benzofuran-2-yl-im idazo[1,2-b]pyridazin-6-yI)-pyridin-2-ylm ethyl-am ine 229_4 5.100 007_0 N

351.41 (3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yI)-pyridin-2-ylmethyl-amine 229_4 5.101 007_0 332.37 [3-(6-Methoxy-pyridin-3-yI)-imidazo[1,2-b]pyridazin-6-ylf-pyridin-2-ylmethyl-amine ALJ/TDS
229_4 5.102 007_0 N N
S
357.44 =
(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-y1)-pyridin-2-ylmethyl-amine 229_4 5.103 007_0 õN

385.35 it 0 F
Pyridin-2-ylmethyl-[3-(3-trifluoromethoxy-phenyI)-imidazo[1,2-b]pyridazin-6-yI]-amine 229_4 5.104 007_0 307.38 S
Pyridin-2-ylmethyl-(3-thiophen-3-yl-imidazo[1,2-13]pyridazin-6-y1)-amine 229_4 5.105 007_0 csNrN.N..,g1 I H
F
369.35 F F
Pyridin-2-ylmethy143-(3-trifluoromethyl-pheny1)-imidazo[1,2-1D]pyridazin-6-y1]-amine 229_4 5.106 007_U

344.42 N/
[3-(3-Dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-pyridin-2-ylmethyl-amine 229_4 5.107 007_0 N

353.79 CI
[3-(3-Chloro-4-fluoro-phenyl)-im idazo[l ,2-b]pyridazin-, 6-y1Fpyridin-2-ylm ethyl-amine 229_4 5.108 N
007_0 331.38 [3-(4-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y11-pyridin-2-ylmethyl-amine 229_4 5.109 007_0 361.40 o\
[3-(3,4-Dimethoxy-phenyI)-imidazo[1,2-b]pyridazin-6-, y1}-pyridin-2-ylmethyl-amine 1229_0 5.110 223_0 .õN

380.83/380 0.93 (negative o mode) OH
416-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-y11-2-methoxy-phenol ALJ/TDS
229_0 5.111 N
223_0 Cl 364.83 HO
{446-(3-Chloro-benzylannino)-imidazo[1,2-b]pyridazin-3-y0-phenylymethanol 229_0 5.112 223_0 ci 196 = N
365.82 (3-Chloro-benzy1)-[3-(5-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y0-amine 229_0 5.113 223_0 ci 284 (00 [\11 N
=OH 350.81 316-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-y0-phenol 229_0 5.114 223_0 CI

335.80 \

(3-Chloro-benzy1)-(3-pyridin-3-yl-imidazo[1,2-blpyridazin-6-y1)-amine 229_U 5.115 223_0 349.82/349 0.92 (negative NH, mode) [3-(3-Amino-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(3-chloro-benzyl)-amine ALJ/TDS
229_0 5.116 223_0 365.82 (3-Chloro-benzy1)13-(6-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.117 223_0 CI

350.81/350 0.89 (negative mode) OH
416-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenol 229_0 5.118 223_0 CI

335.80 /
(3-Chloro-benzy1)-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-y1)-amine 229_0 5.119 223_0 ci . 347N
* o 377.83 346-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yI]-benzamide 229_0 5.120 223_0 ci 140 N"
378.82 O
416-(3-Chloro-benzylam ino)-im idazo[01,2-b]pHyridazin-3-y1i-benzoic acid 229_0 5.121 224_0 N

0.77 319.34/320 (4-Fluoro-benzy1)-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-y1)-amine 229_0 5.122 224_0 0.86 334.35/335 OH
4-[6-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-y11-phenol 229_0 5.123 224_0 N

0.92 349.37/350 \
(4-Fluoro-benzy1)43-(5-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y11-amine 229_0 5.124 224_0 /
N

334.35 OH
346-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-y11-phenol 229_0 5.125 224_0 1.14 338.41/340 (4-Fluoro-benzy1)-[3-(4-methyl-thiophen-2-y1)-imidazo[1,2-blpyridazin-6-y11-amine ALJ/TDS
229_0 5.126 224_0 .õr1,1 N
1.02 362.36/363 o o¨j (3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-y1)-(4-fluoro-benzyl)-amine 229_0 5.127 , 224_0 N

0.96 357.39/358 (4-Fluoro-benzy1)43-(1H-indo1-5-y1)-imidazo[1,2-13]pyridazin-6-y1]-amine , 229_0 5.128 224_0 110 1.04 348.38/349 1 (4-Fluoro-benzy1)-[3-(4-methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.129 224_0 Fl N N-311 =
1.00 349.37/350 (4-Fluoro-benzy1)43-(6-methoxy-pyridin-3-y1)-i imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.130 224_0 ,N
N-0.89 375.41/376 = t N-{3-(6-(4-Fluoro-benzylamino)-imidazo[1,2-_ ALJ/TDS
b]pyridazin-3-y11-phenylyacetamide 229_0 5.131 224_0 H
0.83 319.34/320 (4-Fluoro-benzy1)-(3-pyridin-3-yl-imidazo[1,2-b]pyridazin-6-y1)-amine 229_0 5.132 224_0 0.85 348.38/349 HO
(416-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-y11-phenylymethanol 229_0 5.133 224_0 0 361.38 346-(4-Fluoro-benzylamino)-inn idazo[1,2-b]pyridazin-3-yl]-benzamide 229_0 5.134 ry-N
224_0 =
362.36 HO
4-[6-(4-Fluoro-benzylam ino)-im idazo[1,2-b]pyridazin-3-y1j-benzoic acid 229_0 5.135 e\r--N
244_4 õ.t1.1 139 hi NI
o 1.06 344.42/345 (4-Methoxy-benzy1)-(3-p-tolyl-imidazo[1,2-13]pyridazin-ALJ/TDS
6-yI)-amine 229_0 5.136 244_0 364.83/364 0 1.13 (negative mode) CI
[3-(4-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(4-methoxy-benzy1)-amine 229_0 5.137 244_0 =

350.44/349 0 s 1.09 (negative mode) (4-Methoxy-benzy1)13-(4-methyl-thiophen-2-y1)-imidazo[1,2-blpyridazin-6-y1]-amine 229_0 5.138 244_0 õN
N

o It 0.93 369.43/370 [3-(1H-Indo1-5-y1)-imidazo[1,2-blpyridazin-6-y1]-(4-nnethoxy-benzyl)-amine 229_0 5.139 244_0 N
280 [16 N

360.42 (4-Methoxy-benzy1)43-(4-methoxy-pheny1)-innidazo[1,2-b]pyridazin-6-y11-amine 229_0 5.140 244_0 o 1.04 348.38/349 [3-(4-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(4-methoxy-benzyI)-amine 229_0 5.141 -!%\rõ-N
244_ NN
N

o 0.85 346.39/347 OH
416-(4-Methoxy-benzylannino)-imidazo[1,2-b]pyridazin-3-yli-phenol 229_0 5.142 xjyt2.1 244_7 N

o 0.72 320.35/321 õ..NH
(4-Methoxy-benzy1)-[3-(1H-pyrazol-4-y1)-imidazo[1,2-13]pyridazin-6-y11-arnine 229 0 5.143 o 0.82 334.38/335 ,N
N
(4-Methoxy-benzy1)43-(1-methyl-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-y1]-amine 229_0 5.144 X\r-N
244_0 (110 N 1\1-'1\j \o 374.40 Flo 446-(4-Methoxy-benzylamino)-imidazo[1,2-b]pyridazin-3-yli-benzoic acid ;229_6 5.145 307_0 N
0 \ID Ck 469.52 44[3-(3,4,5-Trimethoxy-pheny1)-imidazo[1,2-blpyridazin-6-ylamino]-methyl}-benzenesulfonamide ALJ/TDS
229_6 5.146 307_0 H ts1 A
* =
425.47 OH
44[3-(4-Hydroxy-3-methoxy-phenyl)-imidazo[1,2-Npyridazin-6-ylaminoFmethylybenzenesulfonamide 229_6 5.147 307_0 395.44 A H

4-{[3-(3-Hydroxy-pheny1)-imidazo[1,2-1Apyridazin-6-ylaminoFmethyl}-benzenesulfonamide 229_6 5.148 307_0 0 \0 4116 429.50 4-[(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-methyll-benzenesulfonamide 229_6 5.149 307_4 H2N,,s 393.47 4-[(3-p-Tolyl-imidazo[1,2-b]pyridazin-6-ylamino)-methylFbenzenesulfonamide ' 229_6 5.150 307_0 116711¨
H2N>
407.50 44[3-(3,4-Dimethyl-pheny1)-imidazo[1,2-1D]pyridazin-6-ylaminoFmethyl}-benzenesulfonamide 229_6 5.151 307_0 o 404.45 4-{[3-(4-Cyano-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminopnethylybenzenesulfonamide 229_6 5.152 307_0 H

//
447.44 o \\0 4-{[3-(3-Trifluoromethyl-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoi-methylybenzenesulfonamide 229_6 5.153 307_0 H2N,,s \\
418.48 O o 4-{[3-(1H-Indo1-5-y1)-imidazo[1,2-1Apyridazin-6-ylaminol-methylybenzenesulfonamide 229_6 5.154 307_0 068 H2Nõ, H
/7\\
? 423.45 o 0 4-[(3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-1Apyridazin-6-ylamino)-methylFbenzenesulfonamide 229 6 5.155 307_0 431.88 O 0 it a 4-{[3-(3-Chloro-4-fluoro-pheny1)-imidazo[1,2-19]pyridazin-6-ylaminoFmethyll-benzenesulfonamide ALJ/TDS
229_6 5.156 307_0 110 463.44 4-{[3-(3-Trifluoromethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminol-methylybenzenesulfonamide 229_6 5.157 307_0 411 409.47 4-{[3-(4-Methoxy-phenyI)-imidazo[1,2-b]pyridazin-6-ylaminoFmethylybenzenesulfonamide 229_6 5.158 307_0 H2N'A 1111 H
0 0 395.44 OH
4-{[3-(4-Hydroxy-phenyl)-imidazo[1, 2-1Apyridazin-6-ylanninoFmethyl)-be nzenesulfonamide 229_6 5.159 307_0 H
291 H,Nõ_ 409.47 OH
4-0-(3-Hydroxymethyl-pheny1)-im id azo[1,2-b]pyridazin-6-ylaminoi-meth y1}-benzenesulfonamide 229_6 5.160 307_4 H
145 H2 1\1::A\

421.48 4-{[3-(3-Acetyl-pheny1)-imidazo[1,2-13]pyridazin-6-ylaminopnethylybenzenesulfonamide ALJ/TDS
229_6 5.161 307_7 383.43 4-{[3-(1-Methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-ylaminoRnethylybenzenesulfonamide 229_0 5.162 227_0 a 40 001.

ck 1.14 459.33 / 461 (3,4-Dichloro-benzy1)43-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-amine 229_0 5.163 227_0 a /
io N
080 Ci 385.25 OH
446-(3,4-Dichloro-benzylamino)-innidazo[1,2-b]pyridazin-3-yll-phenol 229_0 5.164 227_0 c, 399.28 (3,4-Dichloro-benzy1)43-(4-methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.165 227_0 400.27 (3,4-Dichloro-benzy1)13-(6-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-yll-amine 229_0 5.166 227_0 ciio CI
408.29 (3,4-Dichloro-benzy1)-[3-(1H-indo1-5-y1)-imidazo[1,2-b]pyridazin-6-y1Famine ALJ/TDS
229_U 5.167 40.
227_0 c 413.26 =
HO
416-(3,4-Dichloro-benzylamino)-im idazo[1,2-bjpyridazin-3-y11-benzoic acid 229_0 5.168 236_0 =
069 <
=
0.74 345.36/346 Benzo[1,3]dioxo1-5-ylmethyl-(3-pyridin-4-yl-imiclazo[1,2-b]pyridazin-6-y1)-amine 229_0 5.169 236_0 314AI< , = 390.40 =
OH
4-{6-[(Benzo[1,3]dioxo1-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-y1}-2-nnethoxy-phenol 229_0 5.170 236_0 280 <6 1. H
=
0.97 374.40/375 Benzo[1,3]dioxo1-5-ylmethy143-(4-methoxy-pheny1)-imidazo[1,2-Npyridazin-6-yli-amine 229 0 5.171 236_0 H
=

0.95 375.39/376 Benzo[1,3]dioxo1-5-yInnethy143-(6-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.172 =
236_0 41040 080< H
=
0.83 360.37/361 = H
4-{6-[(Benzo[1,3]clioxol-5-ylmethyl)-aminol-imidazo[1,2-b]pyridazin-3-y1)-phenol ALJ/TDS
229_0 5.173 236_0 = 40.
284< H
0 4 OH 0.87 360.37/361 11 3-{6-[(Benzo[1,3]dioxo1-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-y1}-phenol 229_0 5.174 1236_7 =
! 468 <

0.79 348.36/349 Benzo[1,3]clioxo1-5-ylmethyl-[3-(1-methyl-1H-pyrazol-4-y0-imidazo[1,2-1Apyridazin-6-y1Famine 229_0 5.175 236_0 =
140 <

388.38 HO
4-{6-[(Benzo[1,3]dioxo1-5-ylmethyl)-aminoj-imidazo[1,2-b]pyridazin-3-y1}-benzoic acid 229_0 5.176 236_6 =
488 < H
411, H
437.48 N-(3-{61(Benzo[1,3]dioxo1-5-ylmethyl)-aminot-imidazo[1,2-b]pyridazin-3-y1)-phenyly methanesulfonamide 229_0 5.177 236_0 = 40.
347 <
=
= o 387.40 NH, 3-{61(Benzo[1,3]dioxo1-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-ylybenzamide 229 0 5.178 1033_0 *
0.84 358.40/359 ¨0 0 (2-Methoxy-ethy1)13-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-Npyridazin-6-y11-amine ALJ/TDS
229_0 5.179 033_0 N /

o 284.32 (2-Methoxy-ethyl)-[3-(3-methoxy-pheny1)-im idazo[1,2-b]pyridazin-6-y1Fam ine 229_0 5.180 033_0 * o 314.34 OH
2-Methoxy-446-(2-methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol 229_U 5.181 033_0 299.33 0\
(2-Methoxy-ethy1)-[3-(5-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-yli-amine 229_0 5.182 033_0 *AL 1.00 318.38/319 (2-Methoxy-ethyl)-(3-naphthalen-2-yl-imidazo[1,2-13]pyridazin-6-y1)-amine , 229_0 5.183 00.

1311 =
/
299.33 (2-Methoxy-ethy1)13-(6-methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.184 033_0 110.
324.41/323 1.07 (negative mode) (3-Benzo[b]thiophen-2-yl-im idazo[1,2-b]pyridazin-6-y1)-(2-methoxy-ethyl)-amine ALJ/TDS
=
229_0 5.185 033_0 302.76 [3-(4-Chloro-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-(2-methoxy-ethyl)-amine 229_0 5.186 033_0 /

0.84 298.34/299 (2-Methoxy-ethyl)-[3-(4-methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.187 033_0 401.

? 312.33 (3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-y1)-(2-methoxy-ethyl)-amine 229_0 5.188 033_0 312 411 F 1.02 336.32/337 F F
(2-Methoxy-ethy1)13-(3-trifluoromethyl-phenyl)-imidazo[1,2-Npyridazin-6-yli-amine , 229_0 5.189 033_0 00. =
081 * 0.71 325.37/326 N-{346-(2-Methoxy-ethylamino)-imidazo[1,2-Npyridazin-3-y1]-phenylyacetamide 229_0 5.190 033_0 0 F 1.05 352.32/353 (2-Methoxy-ethyl)-13-(3-trifluoromethoxy-pheny1)-imidazo[1,2-Npyridazin-6-y1Famine ALJ/TDS
229_0 5.191 033_0 410.

0.78 307.36/308 \ NH
[3-(1H-Indo1-5-y1)-imidazo[1,2-b]pyridazin-6-y1]-(2-methoxy-ethyl)-amine 229_0 5.192 033_0 /
279 302.76 a [3-(3-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(2-methoxy-ethyl)-amine 229_0 5.193 033_0 /
345 0.92 288.37/289 (2-Methoxy-ethy1)43-(4-methyl-thiophen-2-0)-imidazo[1,2-b]pyridazin-6-y1Famine 229_0 5.194 033_0 /

0.68 284.32/285 OH
4-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenol 229_0 5.195 033_0 0.67 298.34/299 HO
(416-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yll-phenylymethanol 229_0 5.196 033_4 1411111t 1110, 0 0.86 298.34/299 (2-Methoxy-ethy1)43-(3-methoxy-pheny1)-imidazo[1,2-1D]pyridazin-6-y1Famine 229_0 5.197 033_0 277 Br 347.22 [3-(3-Bromo-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(2-methoxy-ethyl)-amine 229_0 5.198 033_0 /

312.33 HO
4-[6-(2-Methoxy-ethylamino)-imidazo[1,2-1Apyridazin-3-yq-benzoic acid 229_0 5.199 , 033_0 311.34 NH, 346-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yll-benzamide 229_0 5.200 033_6 *
361.42 N-{346-(2-Methoxy-ethylamino)-imidazo[1,2-1Apyridazin-3-yli-phenylymethanesulfonamide 229_0 5.201 033_7 =

N
348.41 [3-(1-Benzy1-1H-pyrazol-4-y1)-imidazo[1,2-1Apyridazin-6-y1]-(2-methoxy-ethyl)-amine 229_0 5.202 033_0 N /

It 0 328.37 [3-(3,4-Dirnethoxy-pheny1)-imidazo[1,2-1Apyridazin-6-, y1]-(2-methoxy-ethyl)-amine 229_0 5.203 033_4 310.36 1-{346-(2-Methoxy-ethylamino)-imidazo[1,2-, b]pyridazin-3-y1)-phenylyethanone 229_0 5.204 248_0 HO

di. 0 0.76 358.40/359 ¨0 0 3-[3-(3,4,5-Trimethoxy-phenyI)-imidazo[1,2-b]pyridazin-6-ylaminoj-propan-1-ol 229_0 5.205 õ 248_0 HO

it 0 314.34 OH
446-(3-Hydroxy-propylamino)-imidazo[1,2-lApyridazin-3-y11-2-methoxy-phenol 1229_0 5.206 I 248 0 40*
I ¨ HO
! 277 = Br 347.22 343-(3-Bronno-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFpropan-1-ol 229_0 5.207 248_0 HO \

it 0 0.73 328.37/329 343-(3,4-Dimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFpropan-1-ol ALJ/TDS
229_0 5.208 248_0 HON

F
336.32 F F
313-(3-Trifluoromethyl-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoi-propan-1-ol 229_0 5.209 248_7 HO

272.31 N
3-[3-(1-Methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-ylaminoypropan-1-ol 229_0 5.210 248_0 HO

41 0 F 352.32 Y"--F
3-[3-(3-Trifluoromethoxy-phenyl)-im idazo[1,2-b]pyridazin-6-ylaminoypropan-1-ol 229_0 5.211 248_0 HO
345 s 288.37 343-(4-Methyl-thiophen-2-y1)-imidazo[1,2-b]pyridazin-6-ylaminol-propan-1-ol 229_0 5.212 248_0 HO

=
*AL 0.90 318.38/319 3-(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol 229_0 5.213 248_4 HO

0.79 282.35/283 3-(3-p-Tolyl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol ALJ/TDS
229_0 5.214 248_0 HO
074 0.72 274.35/275 \ s 3-(3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-l-ol 229_0 5.215 248_0 HO
076 i 0.94 324.41/325 3-(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol 229_0 5.216 248_0 HO 4sj 0.69 299.33/300 3-[3-(6-Methoxy-pyridin-3-y1)-imidazo[1,2-1Apyridazin-6-ylaminoFpropan-1-ol 229_0 5.217 248_0 HO

.
307.36/308 \ NH
3-[3-(1H-Indo1-5-y1)-imidazo[1,2-1Apyridazin-6-ylamino]-propan-1-ol 229_0 5.218 248_0 , 280 0.75 298.34/299 3-[3-(4-Methoxy-phenyI)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol 229_0 5.219 248_0 HO

c, 320.75 3-[3-(3-Chloro-4-fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFpropan-1-ol ALJ/TDS
229_0 5.220 248_0 HO

302.76 3-[3-(3-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFpropan-1-ol 229_0 5.221 ' 248_6 361.42 N-{316-(3-Hydroxy-propylamino)-imidazo[1,2-1Apyridazin-3-yli-phenylymethanesulfonamide 229_0 5.222 ' 248_7 HO

\rsr¨N
348.41 3-[3-(1-Benzy1-1H-pyrazol-4-y1)-imidazo[1,2-131pyridazin-6-ylamino]-propan-1-01 229_0 5.223 248_0 HO
135 = N/ 311.39 313-(3-Dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol 229_0 5.224 1248_0 HO

318.38 3-(3-Naphthalen-1-yl-irnidazo[1,2-Npyridazin-6-ylamino)-propan-1-ol 229_0 5.225 1226_0 /

0 0.94 342.40/343 Propyl-[3-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-' __ b]pyridazin-6-y1Famine ALJ/TDS
229_0 5.226 226_0 0 0.81 298.34/299 OH
2-Methoxy-4-(6-propylarnino-imidazo[1,2-b]pyridazin-3-y1)-phenol 229_0 5.227 226_0 40.

411 0 0.91 312.37/313 0¨

, [3-(3,4-Dimethoxy-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-propyl-amine 229_0 5.228 226_0 etik 291.36 \ NH
[3-(1H-Indo1-5-y1)-imidazo[1,2-1Apyridazin-6-y1Fpropyl-amine ' 229_0 5.229 226_4 01.

o 282.35 [3-(3-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y11-, propyl-amine 1229_0 5.230 226_0 .

0.80 309.37/310 N-[3-(6-Propylamino-imidazo[1,2-Npyridazin-3-y1)-phenylFacetamide 229_0 5.231 226_0 o 1.18 336.32/337 FF
Propyl-[3-(3-trifluoromethoxy-phenyI)-imidazo[1,2-b]pyridazin-6-yI]-amine LJ/TDS
229_0 5.232 226_0 0.96 282.35/283 [3-(4-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y11-propyl-amine 229_0 5.233 226_0 074 0.95 258.35/259 \ s Propyl-(3-th iophen-3-yl-im idazo[1,2-b]pyridazin-6-y1)-amine 229_U 5.234 226_0 345 1.06 272.37/273 [3-(4-Methyl-thiophen-2-y1)-imidazo[1,2-1Apyridazin-6-y1Fpropyl-amine 229_0 5.235 226_0 071 / 0.73 253.31/254 Propyl-(3-pyridin-3-yl-im idazo[1,2-b]pyridazin-6-yI)-amine 229_0 5.236 226_0 \N
0.91 283.33/284 [3-(6-Methoxy-pyridin-3-yI)-imidazo [1,2-1Apyridazin-6-y1Fpropyl-amine 229_0 5.237 226_0 411 0.78 268.32/269 OH
4-(6-Propylamino-imidazo[1,2-Npyridazin-3-y1)-phenol ALJ/TDS
229_0 5.238 226_0 ? 0.94 296.33/297 (3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-y1)-propyl-amine 229_0 5.239 226_0 0.81 282.35/283 OH
[3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-y1)-pheny1]-methanol 229_0 5.240 226_0 296.33 HO
4-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yI)-benzoic acid 229_0 5.241 226_0 347 * 0 295.34 3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yI)-benzamide 229_0 5.242 226_0 Orik 135 * N/ 295.39 [3-(3-Dimethylamino-phenyl)-innidazo[1,2-b]pyridazin-6-y1Fpropyl-amine 229_0 5.243 226_0 268.32 OH
3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yI)-phenol ALJ/TDS
229_0 5.244 226_0 Orak 267.33 [3-(3-Amino-pheny1)-imidazo[1,2-b]pyridazin-6-y11-propyl-amine 229_0 5.245 226_0 11111*

267.33 [3-(4-Amino-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-propyl-amine 229_0 5.246 226_0 Alt 295.39 N
[3-(4-Dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-y11-propyl-amine 229_0 5.247 226_0 282.35 HO
[4-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yI)-phenyTmethanol 229_0 5.248 226_0 283.33 [3-(5-Methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y1]-propyl-amine 229_4 5.249 016_4 295.39 N,N-Dimethyl-N'-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-, yl)-ethane-1,2-diamine ALJ/TDS
229_4 5.250 016_0 0.78 321.38/322 N'-(3-Benzofuran-2-yl-imidazo[1,2-b]pyridazin-6-yI)-N,N-dimethyl-ethane-1,2-diamine 229_4 5.251 016_0 287.39 \ s N,N-Dimethyl-N'-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yI)-ethane-1,2-diamine 1229_4 5.252 016_0 *At 331.42 N,N-Dimethyl-N-(3-naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-y1)-ethane-1,2-diannine 229_4 5.253 016_0 076 s 337.45 N'-(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-' 6-yI)-N,N-dimethyl-ethane-1,2-diamine 229_4 5.254 410*

, 079 341.41 N'-[3-(3,4-Dimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-N,N-dimethyl-ethane-1,2-diamine 229_4 5.255 016_0 299.35 N'43-(4-Fluoro-pheny1)-imidazo[1,2-1Apyridazin-6-y11-N,N-dimethyl-ethane-1,2-diamine ALJ/TDS
229_4 5.256 016_0 315.81 ci N'43-(3-Chloro-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-N,N-dimethyl-ethane-1,2-diamine 229_0 5.257 254_0 HN
087 Li =0/
386.45 0\
(S)-3-Methy1-243-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-1Apyridazin-6-ylaminol-butan-1-ol 229_0 5.258 254_0 HN

342.40 H 'W' OH
4464(S)-1-Hydroxymethy1-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-y1]-2-methoxy-phenol 229_0 5.259 254_0 HN
079 Li IP 0/
356.42 (S)-213-(3,4-Dimethoxy-pheny1)-imidazo[1,2-1Apyridazin-6-ylamino]-3-methyl-butan-1-ol 229 0 5.260 1254_0 HN
! 284Y 312.37 OH
3-[6-((S)-1-Hydroxymethy1-2-nnethyl-propylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenol 229_0 5.261 254_0 HN

312.37 OH
4-[6-((S)-1-Hydroxymethy1-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-01-phenol ALJ/TDS
229_0 5.262 254_0 /
HN
285 \.)) 326.40 OH
HO
(S)-2-[3-(4-Hydroxymethyl-pheny1)-imidazo[1,2-131pyridazin-6-ylamino]-3-methyl-butan-1-ol 229_0 5.263 254_0 HN
135 ))fi /
339.44 N\
(S)-243-(3-Dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoF3-methyl-butan-1-ol 229_0 5.264 254_0 .0*
HN
057 Yi."1 .411-346.43 Aar/
(S)-3-Methy1-2-(3-naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-butan-1-ol 229_0 5.265 254_0 HN

364.37 OH
F F
(S)-3-Methy1-213-(3-trifluoromethyl-pheny1)-imidazo[1,2-b]pyridazin-6-ylanninoFbutan-1-ol 229_0 5.266 ; 254_0 40.
HN
068 YI) = ?
340.38 (S)-2-(3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-ylamino)-3-methyl-butan-1-ol 229_0 5.267 254_0 40.
HN

OH
316.43 (S)-3-Methy1-2-[3-(4-methyl-thiophen-2-y1)-imidazo[1,2-b]pyridazin-6-ylaminoFbutan-1-ol 229_0 5.268 254_0 /
HN

302.40 S
OH
(S)-3-Methy1-2-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylarnino)-butan-1-01 229_0 5.269 254_0 FIN
168 Y."1 = ol 380.37 )4-"F
(S)-3-Methy1-213-(3-trifluoromethoxy-phenyl)-imidazo[1,2-to]pyridazin-6-ylaminoFbutan-1-ol 229_0 5.270 254_0 HN

YE)H a 330.82 (S)-2-[3-(3-Chloro-phenyI)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-01 229_0 5.271 254_0 FIN
339 *".1H =
314.36 (S)-2-[3-(4-Fluoro-pheny1)-imidazo[1,2-13]pyridazin-6-ylamino]-3-methyl-butan-1-ol 229_0 5.272 254_0 Ole HN

335.41 (S)-2-[3-(1H-Indo1-5-y1)-imidazo[1,2-b]pyridazin-6-ylaminol-3-methyl-butan-1-ol 229_0 5.273 = 254_0 Or.
HN

o 339.40 3164(S)-1-Hydroxymethy1-2-methyl-propylamino)-imidazo[1,2-bipyridazin-3-yl]-benzamide ALJ/TDS
229_0 5.274 254_4 HN

338.41 1-{3-[6-((S)-1-Hydroxymethy1-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-y11-phenylyethanone 229_0 5.275 254_0 Or.
HN
196327.39 N
(S)-2-[3-(5-Methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol 229_0 5.276 153_0 40*
HN

--A IP
372.42 ¨0 243-(3,4,5-Trimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol 229_0 5.277 153_0 ci 334.78 2-[3-(3-Chloro-4-fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-ylam ino]-butan-1-o1 229_0 5.278 1153_0 41*
HN
, 057 0.99 332.41/333 oti .10 2-(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-butan-1-ol 229_0 5.279 153_0 HN

1.02 366.34/367 213-(3-Trifluoromethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol 229_0 5.280 153_0 HN

s 0.82 288.37/289 OH
2-(3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylamino)-butan-1-ol 229_0 5.281 153_0 40.

-1s) OH 1110 0.86 312.37/313 243-(4-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFbutan-1-ol 229_U 5.282 153_0 S 0.90 302.40/303 OH
243-(4-Methyl-thiophen-2-y1)-imidazo[1,2-b]pyridazin-6-ylaminoFbutan-1-ol 229_0 5.283 153_0 FIN
279 =ci 316.79 OH
213-(3-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFbutan-1-ol ' 229_0 5.284 , 153_0 1410.

\ N 0.79 313.36/314 OH

2-[3-(6-Methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-ylaminol-butan-1-ol 229_0 5.285 153_7 FIN

0.67 286.34/287 oH N
213-(1 -Methyl-1 H-pyrazol-4-y1)-imidazo[1,2-, b]pyridazin-6-ylaminoi-butan-1-ol ALJ/TDS
229_0 5.286 153_0 `.:TI lip Br 361.24 OH
243-(3-Bromo-phenyl)-im idazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol 229_0 5.287 153_0 HN
312 F F 1.00 350.34/351 OH IP
243-(3-Trifluoromethyl-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoFbutan-1-ol 229_0 5.288 153_4 140 0.86 312.37/313 OH 0\
243-(3-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol 229_0 5.289 153_0 347= o 325.37 oH
3-[6-(1-Hydroxymethyl-propylamino)-imidazo[1,2-b]pyridazin-3-y1]-benzamide 229_0 5.290 153_0 HN

OH *
326.35 OH

4-[6-(1-Hydroxymethyl-propylamino)-imidazo[1,2-b]pyridazin-3-y1Fbenzoic acid 229_0 5.291 153_7 HN

OH N
362.44 2-[3-(1-Benzy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-ylaminoFbutan-1-ol LJ/TDS
229_0 5.292 153_6 *

375.45 OH
N-{3-[6-(1-Hydroxymethyl-propylamino)-imidazo[1,2-1Apyridazin-3-y1]-phenylymethanesulfonamide 229_0 5.293 153_4 324.38 1434641 -Hydroxymethyl-propylamino)-imidazo[1,2-b]pyridazin-3-y1J-phenylyethanone 229_0 5.294 153_0 HN

OH # (3\ 342.40 2-[3-(3,4-Dimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoi-butan-1-01 229_0 5.295 153_0 HN

/
313.36 OH N (3\
2-[3-(5-Methoxy-pyridin-3-yI)-imidazo[1,2-b]pyridazin-6-ylaminol-butan-1-ol 229_0 5.296 242_0 41.* =

384.43 (Tetrahydro-pyran-4-y1)-(3-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-yI]-amine 229_0 5.297 242_4 324.38 [3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-y1F
(tetrahydro-pyran-4-yI)-amine ALJ/TDS
229 0 5.298 242_0 "

362.35 F F
(Tetrahydro-pyran-4-y1)43-(3-trifluoromethyl-phenyl)-imidazo[1,2-1Apyridazin-6-y1Famine 229_0 5.299 ' 242_0 324.38 HO
{446-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-1Apyridazin-3-y11-phenylymethanol 229_0 5.300 242_0 4.*

314.41 [3-(4-Methyl-thiophen-2-y1)-imidazo[1,2-b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.301 242_0 346.79 [3-(3-Chloro-4-fluoro-phenyI)-imidazo[1,2-b]pyridazin-i 6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.302 1242_0 aN ere =
; 277 373.25 Br [3-(3-Bromo-pheny1)-imidazo[1,2-131pyridazin-6-y1]-(tetrahydro-pyran-4-yI)-amine 229_0 5.303 242_7 298.35 --N
N
[3-(1-Methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-. 6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.304 242_0 324.38 OH
{3-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenylymethanol 229_0 5.305 242_0 325.37 N
[3-(5-Methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.306 242_0 N or.

324.38 [3-(4-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y11-(tetrahydro-pyran-4-yI)-amine 229_0 5.307 242_0 312.35 [3-(4-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(tetrahydro-pyran-4-yI)-amine 1229_0 5.308 242_0 api =

333.39 [3-(1H-Indo1-5-y1)-imidazo[1,2-b]pyridazin-6-yI]-' (tetrahydro-pyran-4-yI)-amine 229_0 5.309 242_0 N
1135 =
337.43 N/
1 [3-(3-Dimethylamino-pheny1)-imidazo[1,2-1Apyridazin-6-y11-(tetrahydro-pyran-4-y1)-amine _ _ ALJ/TDS
229_0 5.310 242_0 1.01 344.42/345 = (3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-y1)-(tetrahydro-pyran-4-y1)-amine 229_0 5.311 242_0 N

0.95 322.41/323 [3-(3,4-Dimethyl-phenyl)-imidazo[1,2-1Apyridazin-6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.312 242_0 N N /
142 / 0.81 284.32/285 (3-Furan-2-yl-imidazo[1,2-1Apyridazin-6-y1)-(tetrahydro-pyran-4-yI)-amine 229_0 5.313 242_0 N

0.67 381.43/382 H
N-(2-Hydroxy-ethyl)-316-(tetrahydro-pyran-4-ylamino)-imidazo[1,2-1Apyridazin-3-ylybenzamide 229_0 5.314 1242_2 =
! 175 0.90 352.39/353 0 \
416-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-blpyridazin-3-y1]-benzoic acid methyl ester 229_0 5.315 242_4 /

0.90 308.38/309 (Tetrahydro-pyran-4-y1)-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-y1)-amine ALJ/TDS
229_0 5.316 eft 242_0 0.68 309.37/310 NH, [3-(4-Amino-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.317 242_0 337.43 N--_ [3-(4-Dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-y11-(tetrahydro-pyran-4-y1)-amine 229_0 5.318 242_0 4s1 081 t 0.73 351.41/352 /7 ¨0 N-{316-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenylyacetamide 229_0 5.319 242_0 309.37 [3-(3-Amino-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-(tetrahydro-pyran-4-yI)-amine 229_0 5.320 1242_4 erik.

411 0.85 312.35/313 [3-(2-Fluoro-pheny1)-imidazo[1,2-1Apyridazin-6-y1]-(tetrahydro-pyran-4-yI)-amine 229_0 5.321 242_0 344.42 (3-Naphthalen-1-yl-imidazo[1,2-1Apyridazin-6-y1)-L_. (tetrahydro-pyran-4-yI)-amine Ulf-DS
229_0 5.322 242_0 -. 24 /
071 \N 0.65 295.34/296 (3-Pyridin-3-yl-imidazo[1,2-b]pyridazin-6-y1)-(tetrahydro-pyran-4-y1)-amine 229_0 5.323 242_0 328.80 CI
[3-(4-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.324 242_0 , 338.37 (3-Benzo[1,3]dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-y1)-(tetrahydro-pyran-4-y1)-annine 229_0 5.325 242_0 oa 40e 284 # 0.74 310.36/311 OH
346-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yI]-phenol 229_0 5.326 1242_0 aN
074 0.84 300.38/301 \ s (Tetrahydro-pyran-4-yI)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yI)-amine 229_0 5.327 242_0 a 079 0/ 0.81 354.41/355 [3-(3,4-Dimethoxy-phenyI)-imidazo[1,2-b]pyridazin-6-yI]-(tetrahydro-pyran-4-y1)-amine ALJ/TDS
229_0 5.328 242_0 41 0 1.06 378.35/379 FF
(Tetrahydro-pyran-4-y1)13-(3-trifluoromethoxy-pheny1)-imidazo[1,2-b]pyridazin-6-yli-amine 229_0 5.329 242_0 F 312.35 [3-(3-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-, (tetrahydro-pyran-4-yI)-amine 229_0 5.330 242_0 * 0 340.38 OH
2-Methoxy-4-[6-(tetrahydro-pyran-4-ylamino)-imidazo[1,2-1Apyridazin-3-y1Fphenol 229_0 5.331 242_4 147 0.83 300.38/301 (Tetrahydro-pyran-4-yI)-(3-thiophen-2-yl-im idazo[1, 2-b]pyridazin-6-yI)-am ine 229_0 5.332 242_7 41*
I 467 0.59 284.32/285 =
[3-(1H-Pyrazol-4-y1)-imidazo[1,2-1Apyridazin-6-A-(tetrahydro-pyran-4-yI)-amine 229_0 5.333 242_0 aN 40*
347 At 0 337.38 NH, 3-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-, b]pyridazin-3-y1]-benzamide ALJ/TDS
229_0 5.334 242_7 rs,C3 374.45 [3-(1-Benzy1-1H-pyrazol-4-y1)-imidazo[1,2-1Apyridazin-6-y1]-(tetrahydro-pyran-4-y1)-amine 229_0 5.335 242_0 338.37 HO
446-(Tetrahydro-pyran-4-ylarnino)-imidazo[1,2-b]pyridazin-3-y1]-benzoic acid 229_0 5.336 242_6 488 = "I
387.46 N-{3-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-1Apyridazin-3-y1]-pheny1}-methanesulfonamide 229_0 5.337 242_0 N
1279 328.80 [3-(3-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-. (tetrahydro-pyran-4-y1)-amine 1229_0 5.338 HO..

-354.41/353 0 0.70 (negative mode) OH
4-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-y1]-2-methoxy-phenol ALJ/IDS
229_0 5.339 HO a l 240_0 /

392.38 f 443-(3-Trifluoromethoxy-phenyl)-innidazo[1, 2-b]pyridazin-6-ylamino]-cyclohexanol 229_0 5.340 HOTa 240_4 it 0 0.79 338.41/339 413-(3-Methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminol-cyclohexanol 229_0 5.341 HOla 240_0 /

314.41 \ s 4-(3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol 229_0 5.342 HOlia 240_0 076 / s 364.47 4-(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-ylaminoycyclohexanol 229_0 5.343 HO
I 240_0 40.
1135 * tl/
351.45 4-[3-(3-Dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminol-cyclohexanol 229_0 5.344 HO , 240_0 /

F
326.37 413-(3-Fluoro-pheny1)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol 229_0 5.345 HO
240_0 140*
062 0.83 358.44/359 4-(3-Naphthalen-1-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol 229_0 5.346 HO
240_0 40.

= rslc,_ 365.44 N-{316-(4-Hydroxy-cyclohexylam ino)-im idazo[1, 2-b]pyridazin-3-A-phenylyacetamide 229_0 5.347 HOõ.ra 240_0 324.38 OH
4-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-1Apyridazin-3-yll-phenol 229_0 5.348 HOla 240_0 /

358.44 4-(3-Naphthalen-2-yl-imidazo[1,2-1Apyridazin-6-ylaminoycyclohexanol 229_0 5.349 HOia 240_0 =
i 061 308.38 4-(3-Phenyl-imidazo[1,2-13]pyridazin-6-ylamino)-cyclohexanol 229_0 5.350 HOla 240_0 347.42 \ NH
4-[3-(1H-Indo1-5-y1)-imidazo[1,2-b]pyridazin-6-_ylaminol-cyclohexanol ALSTDS
229_0 5.351 HOI:a 240_0 /

351.45 4-[3-(4-Dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminoRyclohexanol 229_0 5.352 HO-.
240_0 /

338.41 413-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylaminol-cyclohexanol 229_0 5.353 H00, 240_0 Nlk 078 359.43 4-(3-Quinolin-8-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol 229_0 5.354 240_0 142 = / 0 298.34 4-(3-Furan-2-yl-imidazo[1,2-19]pyridazin-6-ylamino)-cyclohexanol ' 229_0 5.355 HO
1240_2 366.42/365 0.82 (negative mode) 0 (:\
446-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-yll-benzoic acid methyl ester 229_0 5.356 H01, 240_0 3 /

392.38 FfF
4-[3-(4-Trifluoromethoxy-phenyI)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol ALJTIDS
229_0 5.357 240_0 336.44 443-(3,4-Dimethyl-pheny1)-imidazo[1,2-1D]pyridazin-6-ylannino]-cyclohexanol 229_0 5.358 HOra 240_0 338.41 HO
1 443-(4-Hydroxymethyl-pheny1)-imidazo[1,2-1Apyridazin-6-ylaminol-cyclohexanol 229_0 5.359 HOla 240_0 342.83 443-(4-Chloro-pheny1)-imidazo[1,2-b]pyridazin-6-ylaminol-cyclohexanol 229_0 5.360 240_0 339.40 443-(6-Methoxy-pyridin-3-y1)-imidazo[1,2-b]pyridazin-i 6-ylamino]cyclohexanol ' 229 0 5.361 H00, I ¨
240_0 , 196 /
339.40 443-(5-Methoxy-pyridin-3-y1)-imidazo[1,2-1Apyridazin-6-ylaminol-cyclohexanol 229_0 5.362 HO
240_0 284 it 324.38 OH
3-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-, Npyridazin-3-yl1-phenol ALJ/TDS
229_0 5.363 HOla 240_0 352.39 OH

4-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-y11-benzoic acid 229_4 5.364 051_0 it 0 354.41 ¨0 0 Cyclopropylmethy143-(3,4,5-trimethoxy-pheny1)-imidazo[1,2-13]pyridazin-6-yll-amine 229_4 5.365 051_0 \7/N

o 310.36 OH
446-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-y11-2-methoxy-phenol 229_4 5.366 051_0 V)\-1 o 324.38 0¨

, Cyclopropylmethyl-[3-(3,4-dimethoxy-phenyI)-imidazo[1,2-Npyridazin-6-y0-amine 229_4 5.367 051_0 V1-1 135 is( 307.40 Cyclopropylmethy143-(3-dimethylamino-pheny1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_4 5.368 , 051_0 \71N-1 265.32 Cyclopropylmethyl-(3-pyridin-4-yl-irnidazo[1,2-blpyridazin-6-y1)-amine ALJ/TDS
229_4 5.369 051_0 N /

294.36 OH
{346-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-y1J-pheny1}-methanol 229_4 5.370 051_4 sN
40*

* 0 294.36 Cyclopropylmethy113-(3-methoxy-pheny1)-imidazo[1,2-1Apyridazin-6-y11-amine 229_4 5.371 051_7 268.32 N N
Cyclopropylmethyl-[3-(1-methy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-01-amine 229_4 5.372 051_7 NH

254.30 Cyclopropylmethyl-[3-(1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-y1Famine 229_4 5.373 051_0 308.34 (3-Benzo[1,3]clioxol-5-yl-imidazo[1,2-b]pyridazin-6-y1)-cyclopropylmethyl-amine 229_4 5.374 051_0 294.36 Cyclopropylmethy143-(4-methoxy-pheny1)-imidazo[1,2-b]pyridazin-6-y1]-amine 229_4 5.375 051_0 \Kts, 270.36 \ s Cyclopropylmethyl-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-y1)-amine 229_4 5.376 051_0 295.34 Cyclopropylmethyl-[3-(6-methoxy-pyridin-3-yI)-imidazo[1,2-b]pyridazin-6-y1Famine 229_4 5.377 051_0 4s1 284.39 Cyclopropylmethyl-[3-(4-methyl-thiophen-2-yI)-imidazo[1,2-b]pyridazin-6-y1Famine 229_4 5.378 051_0 40.
\Y-N
081 = 1"1\__ 321.38 O
N-{346-(Cyclopropylmethyl-amino)-imidazo[1,2-1Apyridazin-3-ylj-phenylyacetamide 229_4 5.379 051_0 vN

351.41 HN-Th OH
316-(Cyclopropylmethyl-amino)-imidazo[1,2-1Apyridazin-3-A-N-(2-hydroxy-ethyl)-benzamide 229_4 5.380 051_0 40.

294.36 HO
(4-[6-(Cyclopropylmethy4-amino)-im idazo[1,2-b]pyridazin-3-yli-phenylymethanol ALJ/TDS
229_4 5.381 051_0 280.33 OH
446-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-01-phenol 229_4 5.382 051_0 .V)1 280.33 OH
3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-1D]pyridazin-311]-phenol 229_4 5.383 051_6 488 =
357.44 o-N-{346-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-y11-pheny1}-methanesulfonamide 229_4 5.384 051_0 '711 308.34 OH
3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-1Apyridazin-3-yli-benzoic acid 229_4 5.385 ; 051_7 00*
= V711 ,N

344.42 [3-(1-Benzy1-1H-pyrazol-4-y1)-imidazo[1,2-b]pyridazin-6-A-cyclopropylmethyl-amine 229_4 5.386 051_U

308.34 HO
446-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-y11-benzoic acid ALJ/TDS
229_4 5.387 051_0 01*
\7.
347 11 o 307.36 NH, 3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-y11-benzamide 229_4 5.388 051_4 306.37 1-{346-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-y1]-pheny1}-ethanone , 229_4 5.389 051_4 \7."

270.36 Cyclopropylmethyl-(3-thiophen-2-yl-imidazo[1,2-b]pyridazin-6-y1)-amine Description of the HPLC-MS analysis conditions for the examples listed in Table 5:
Detection: UV = 200 ¨ 350 nm (Waters Acquity HPLC)/ MS 100-800 Daltons; 20 V
(Micromass / Waters ZQ 4000); column: X Bridge (Waters), 2.1 x 50 mm, BEH
1.7 pm; eluent: A: H20/0.05% HCOOH, B: CH3CN/0.05% HCOOH.
Gradient: 10-90% B in 1.7 min, 90% B for 0.2 min, 98-2% B in 0.6 min; flow rate:
1.3 ml/min.
P-(2-Methoxypyridin-4-y0imidazo[1,2-13.1pyridazin-6-Apiperidin-4-ylamine (Example 6.0) FiNa N

ALJ/TDS
Stage A: 443-(2-methoxypyridin-4-yl)imidazo[1,2-Npyridazin-6-ylamino]piperidine-1-carboxylic acid tert-butyl ester (Example 6.1) .4,0ANo, CI
292 mg of 443-(2-methoxypyridin-4-yl)imidazo[1,2-b]pyridazin-6-ylamino]piperidine-1-carboxylic acid tert-butyl ester were prepared from 300 mg (1.15 mmol) of 6-chloro-3-(2-methoxypyridin-4-y0imidazo[1,2-b]pyridazine (Example 1.14) and 230 mg (1.15 mmol) of 4-aminopiperidine-1-carboxylic acid tert-butyl ester (CAS
No. 87120-72-7) by method A.
1H-NMR (300 MHz, d6-DMS0): 8 = 1.32 ¨ 1.38 (m, 11H); 2.02 ¨ 2.08 (m, 2H);
2.92 ¨ 3.00 (m, 2H); 3.72 ¨ 3.92 (m, 6H); 6.73 (d, 1H); 7.17 ¨ 7.19 (m, 1H);
7.64 ¨
7.66 (m, 1H); 7.76 ¨7.79 (m, 2H); 8.11 ¨8.16 (m, 2H) ppm.
MS (ES+): m/z = 425 (M+H)+ [mol. weight = 424.51].
Stage 13: (3-(2-methoxypyridin-4-y0imidazo[1,2-13.1pyridazin-6-yllpiperidin-4-ylamine (Example 6.0) 0)LN HNia 280 mg (0.66 mmol) of 443-(2-methoxypyridin-4-yl)imidazo[1,2-b]pyridazin-6-ylamino]piperidine-1-carboxylic acid tert-butyl ester were introduced into 3 ml of THF

ALJ/TDS
and, after addition of 0.8 ml of HCI in dioxane (4M), stirred at RT overnight.
HCI
(conc.) was added, and the mixture was heated at 70 C for 4 hours. The reaction was diluted with water, adjusted to pH 11 with Et3N and extracted three times with ethyl acetate. The combined organic phases were filtered through a silicone filter (from Whatman) and concentrated. In the final fractionation by chromatography on silica gel, 92 mg of the desired product were isolated.
1H-NMR (300 MHz, d6-DMS0): 6 = 1.30 - 1.43 (m, 2H); 2.03 - 2.08 (m, 2H); 2.59 -2.67 (m, 2H); 2.99 - 3.06 (m, 2H); 3.66 - 3.75 (m, 1H), 3.89 (s, 3H); 6.77 (d, 1H);
7.15 - 7.18 (m, 1H); 7.66 - 7.69 (m, 1H); 7.80 (d, 1H); 8.87 (s, 1H); 8.15 -8.19 (m, 2H) ppm.
MS (ES+): m/z = 325 (M+H)+ [mol. weight = 324.39].
The following example was prepared analogously:
Example Structure and name of the main isomer 11-1-NMR Mol. weight/
No. MS (ES+) [M+1]+
6.2 HN (300 MHz, d6-DMS0): 324.39/325 Cr/ 8 = 1.22 - 1.35 (m, 2H); 1.92 - 1.97 (m, / \ 2H); 2.49 - 2.57 (m, =
2H, partly covered by solvent); 2.90 - 2.97 (m, 2H); 3.55 - 3.67 (m, 1H); 3.86 (s, 3H);
[3-(6-Methoxy-pyridin-3-y1)-imidazo[1,2-6.64 (d, 1H); 6.96 -b]pyridazin-6-yli-piperidin-4-yl-amine 6.98 (m, 1H); 7.70 (d, 1H); 7.80 (s, 1H); 8.38 (dd, 1H) ppm.

ALJ/TDS
346-(2-Hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yllbenzenesulfonamide (Example 7.0) FION
it )7 S.-NH
H it 82 mg (0.21 mmol) of N-tert-butyl-346-(2-hydroxyethylamino)imidazo[1,2-b]pyridazin-3-yl]benzenesulfonamide were mixed under argon with 1.7 ml of trifluoroacetic acid and stirred at 50 C for 5 hours. After cooling, the mixture was concentrated in vacuo, and the residue was taken up in ethyl acetate. The organic phase was washed with saturated NaHCO3 solution and saturated NaCI solution, filtered through a Whatman filter and concentrated. The resulting residue was purified by chromatography (DCM/Et0H 6:4). 47 mg of the product were obtained.
1H-NMR (400 MHz, d6-DMS0): 6 = 3.36 ¨ 3.40 (m, 2H); 3.61 ¨ 3.65 (m, 2H); 4.77 (t, 1H); 6.78 (d, 1H); 7.17 (t, 1H); 7.35 (s, 2H); 7.59 ¨ 7.63 (m, 1H); 7.70 -7.76 (m, 2H);
7.95 (s, 1H); 8.25 (d, 1H); 8.87 (m, 1H) ppm.
The following example was prepared analogously:
Example Structure and name of the main isomer 'H-NMR Mol. weight!
No. MS
(ESI) [M+1]+

ALJ/TDS
MW:
HN N 333.37 =

7.1Se H2Ni '0 416-(2-Hydroxy-ethylamino)-innidazo [1,2-1Apyridazin-3-y11-benzenesulfon amide The following examples were prepared from 4-(6-chloroimidazo[1,2-1Apyridazin-3-yl)phenol and the appropriate amine in analogy to Example 1.5:
Example Structure and name of the main isomer 11-I-NMR Mol. weight /
No. MS (ES+) MW 311.39 HN N
,f4 MS (ES+):
[M+11+ 312 8.0 NY
OH
446-(3-Dimethylamino-propylamino)-imidazo[1,2-b]pyridazin-3-y1]-phenol ALJ/TDS
(DMSO-d6, stored over molecular HN N
sieves): 8 = 2.40 (m, 4H); 2.54 (m, 2H);
8.1 3.37 (m, 2H); 3.56 (m, OH 4H); 6.63 (d, 1H); 6.80 0 (d, 1H); 6.92 (m, 1H);
446-(2-Morpholin-4-yl-ethylam ino)-7.66 (m, 2H); 7.94 (d, 1H) ppm .
imidazo[1,2-b]pyridazin-3-y11-phenol Biological effects The following examples describe the biological effect of the compounds of the invention:
It is clear to the skilled worker that there is a number of disorders in which the cause of the disorder derives from a dysfunction of one or more kinases.
Dysfunctions of kinases can be induced by a large number of mechanisms, e.g. a kinase may be overexpressed, leading to a faulty cellular activity, or a mutated kinase may be overexpressed, likewise leading to a faulty cellular activity.
The faulty cellular activity may be for example a faulty cellular proliferation, especially an increased cellular proliferation (cellular hyperproliferation). The result of such dysfunctions may be for example a disorder which is characterized by overexpression or mutation of the kinase.
Appropriate assays for testing the efficacy of the compounds of the invention for the ability to modulate kinase activity are known. Also known are assays in order to investigate the efficacy of the compounds of the invention in modulating cellular proliferation.

ALJ/TDS
The following biological examples therefore serve merely to describe by way of example the uses according to the invention of the claimed compounds and are therefore not to be understood as limiting in any way.
Significance of IL-2 in the T cell immune response The extent to which test substance influence antibody-induced interleukin 2 (IL-2) secretion was investigated in the following test system. IL-2 represents a central cytokine which is produced and released by activated T cells. IL-2 synthesis in the T cells is regulated by a plurality of kinases. An inhibitory effect of substances on kinases leads inter alia to inhibition of IL-2 synthesis and inhibition of the T cell io immune response. The cytokine determinations were carried out using an ELISA
kit.
Description of the test system Peripheral blood mononuclear cells (PBMC) were isolated from heparinized human is whole blood by gradient centrifugation using Histopaque 1077 (Sigma) at room temperature, and the erythrocytes were lyzed hypotonically and, after washing twice in PBS, taken up in cell culture medium (10% fetal inactivated calf serum in RPMI-1640 + Glutamax-I [Gibco]).
The 96 well culture plates (Costar) were previously incubated with 100 pl of 20 antibody solution in PBS 0.1 pg/ml in PBS [Gibco]) per well at 4 C for 18 hours.
The antibodies used were anti-CD3 and anti-CD28 monoclonal antibodies (PharMingen). After washing with PBS three times, the plates were charged with 200 pl of the cell suspension (40 000 cells/well). In addition, the test substances were added in concentrations such that they were present in concentrations of 25 1 X 106_ 1X10-12 M.

ALJ/TDS
The cultures were incubated in an incubator at 37 C for 20 hours. After this incubation, the plates were briefly shaken and centrifuged, and 250 pl of supernatant were removed, and the supernatants were then frozen at -20 C.
Interleukin-2 was determined using an ELISA kit (Bioscience), and the absorption of the color change was analyzed in a SpectraMax 340 PC (wavelength 450 nm).
Active substances brought about a reduction in the absorption.
Table 1: Assay data Example Structure Inhibition IC50 [mo1/1]
(concentration No. of PKC for 50% inhibition of IL-2) theta inhibition at 10 pM

[mo1/1]
OP 3070 6.1 x 10-6 1.4x10-6, >95%
inhibition N N at 10 pM
(3-Phenyl-imidazo[1,2-b]pyridazin-6 -y1)-(3-pyrrolidin-1-yl-propy1)-amine OP 3071 1.7 x 10-5 2.5x106, >95% inhibition ,4 /
N N at 10 pM
(3-Morpholin-4-yl-propyI)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yI)-amine OP 3073 2.5 x 10-7 2.1x10-7, >95%
inhibition N at 10 pM
11' CI
[3-(3-Chloro-phenyI)-imidazo[1,2-b]
pyridazin-6-yI]-(3-pyrrolidin-1-yl-propyI)-amine ALJ/TDS

4.1 x10-' 9.2x10-7, >95% inhibition at 10 pM
CI
[3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-y1]-(3-morpholin-4-yl-propyI)-amine 1.29 x 10-5 1.7 x 10-6 002-a Nj (3-Imidazol-1-yl-propy1)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yI)-amine fµl 1.13 x 10-5 2.0 x 10-6 006-a /k.
N.N
=
[345-Methy1-1H-pyrazol-4-y1)-propyl]
(3-phenyl-imidazo[1,2-b]pyridazin-6-:
-amine KEI322-5.4 x 10-6 1.1 x 10-6 010-a NI
N N
N*1*,N*1*-Diethyl-N*4*-(3-phenyl-imidazo[1,2-b]pyridazin-6-y1)-pentane -1,4-diamine KE1322- 5.5 x 10-6 2.6 x 10-6 011-a N

N,N-Diethyl-N'-(3-phenyl-imidazo [1,2-13]pyridazin-6-y1)-propane-1,3-diamine ALJ/TDS
KE1322- 7.2 x 10-6 1.1 x 10-6 014-a .."(-=/
NNj "
* CI
[3-(3-Chloro-pheny1)-imidazo[1,2-13]
pyridazin-6-yI]-(3-imidazol-1-yl-propyI)-amine 2.2 x 10-7 2.9 x 10-7 022-a ==N
N N
# CI
N*4*-[3-(3-Chloro-phenyI)-imidazo [1,2-b]pyridazin-6-y1J-N*1*,N*1*-diethyl-pentane-1,4-diamine KE1322- 2.5 x 10-7 2.1 x 10-7 023-a A- -1;1 /
N N N
* CI
N'-[3-(3-Chloro-phenyl)-imidazo [1,2-b]pyridazin-6-y1FN,N-diethyl-propane-1,3-diamine KE1322- 1.7 x 10-6 1.0 x 10-6 024-a ON
N
* CI
[3-(3-Chloro-phenyl)-imidazo [1,2-13]pyridazin-6-yI]-(2-pyrrolidin-1-yl-ethyl)-amine ALJ/TDS
KEI322- 7.0 x 10-6 028-a (r1 / I
N-N
Cyclohexylmethy143-(I-methyl-1H-pyrazol-4-y1)-imidazo[1,2-13]pyridazin 6-y1Famine KE1322- N 7.2 x 10-6 0.7 x 10-6 030-a N-N
[341-Methy1-1H-pyrazol-4-y1)-imidazc [1,2-b]pyridazin-6-y1H3-(5-methyl-1H-pyrazol-4-y1)-propylFamine 1.3 x 10-5 0.4 x 10-6 042-a NN /
S
[3-(5-Methyl-1 H-pyrazol-4-y1)-propy1]-(3-thiophen-3-yl-imidazo-[1,2-13]pyridazin-6-y1)-amine ALK1 Kinase flashplate assay In order to examine the activity of compounds, an ALK1 kinase flashplate assay was established and used.
ALK1 phosphorylates serine/threonine residues of the biotinylated substrate bovine a-casein in the presence of [7-3313]ATP. The radiolabeled product is detected through binding to streptavidin-coated flashplates. The biotin residues of the biotinylated casein bind with high affinity to the streptavidin. Radiolabeled ALJ/TDS
biotinylated casein resulting from the ALK1 kinase reaction causes a chemiluminescence signal after the streptavidin-mediated binding to the scintillator-containing surface of the flashplate has taken place. This signal derives from the closeness of the radioactive label to the scintillator in the surface of the well of the flashplate. Unphosphorylated substrate causes no signal because it contains no radiolabeled phosphate groups. Free [y-33P]ATP remaining unbound in the solution (supernatant) is washed out of the wells of the flashplates and therefore makes no significant contribution to a background signal. The measured signals are therefore a measure of the ALK1 kinase activity. Measurement takes place in a Perkin-Elmer io top count apparatus or a Perkin-Elmer ViewLux instrument.
Material:
Enzyme: purified human recombinant ALK1 kinase (GST fused to the intracellular domain of ALK1 [His142-G1n503]); self-prepared; aliquots are stored at -80 C;
diluted enzyme working solution: 2.5 ng/pl ALK1 (in assay buffer) is freshly prepared and stored on ice until used.
Substrate: biotinylated bovine a-casein. Unbiotinylated casein from Sigma is biotinylated by standard methods using a biotin-N-hydroxysuccinimide (NHS) ester.
Substrate working solution: 0.83 pM ATP, 1.67 pM biotinylated a-casein, 7.4 nCi of [11-3313]ATP/p1 in assay buffer Assay plates: 384-well plates, small volume, white, Greiner (# 784075) Flashplates: streptavidin-coated flashplates, Perkin Elmer (384-Well #
SPM410A) Assay buffer: 50 mM Tris/HCI pH 8.0, 1 mM MnCl2, 1 mM DTT, 0.01% NP40, 0.5x complete EDTA-free Stop solution: 33.3 pM ATP, 33.3 mM EDTA, 0.07% Triton X-100 in PBS
Saturation solution for flashplates: 100 pM ATP, 0.2% Triton X-100 in PBS
Adhesive film for plates: Greiner (# 676080) Description of assay ALJ/TDS
Protocol for a 5 pl assay (all steps are carried out at 20 C; a CyBi-well pipettor and a multidrop microdispensor is used for pipetting):
1. 50 nl or 250 nl of substance in 100% DMSO
2. addition of 3 pl of substrate working solution using a CyBi-Well pipettor 3. addition of 2 pl of enzyme working solution using a multidrop microdispensor Incubation at room temperature (20 C) for 60 min 4. addition of 15 pi of stop solution using a CyBi-Well pipettor 5. transfer of 18 pl of assay mixture into flashplates** using a CyBi-Well pipettor Incubation at room temperature for at least 3 h or at 4 C overnight in order to allow lo binding to the streptavidin-coated flashplates.

6. washing of the flashplates three times with 50 pl of PBS without Ca ++ and Mg++
each time 7. sealing of the plates with adhesive film 8. measurement in the top count (60 sec/well) **Saturation of the flashplates: the flashplates are preincubated with 50 pl of saturation solution for at least 1 h. 18 pl of this solution are discarded before 18 pl of assay mixture are transferred into the flashplates Final concentrations calculated for a reaction volume of 5 pl: 5 ng of ALK1/well;
1 pM biotinylated a-casein; 0.5 pM ATP; 22 nCi/well [y-331:1ATP; 1 mM MnC12, 1 mM DTT; 50 mM Tris-HCI, pH 8.0; 0.01% NP40; 0.5x complete EDTA-free; 1 (Yo =
or 5% DMSO.
The data are normalized (enzyme reaction without inhibitor = 0% inhibition, enzyme reaction in the presence of 10 mM EDTA = 100% inhibition) and 1050 values are calculated using a 4-parameter fit with the aid of an in-house software.
ALK4 kinase flashplate assay In order to examine the activity of compounds, an ALK4 kinase flashplate assay was established and used.

ALJ/TDS
ALK4 phosphorylates serine/threonine residues of the biotinylated substrate bovine a-casein in the presence of [y-33P]ATP. The radiolabeled product is detected through binding to streptavidin-coated flashplates. The biotin residues of the biotinylated casein bind with high affinity to the streptavidin. Radiolabeled biotinylated casein resulting from the ALK4 kinase reaction causes a chemiluminescence signal after the streptavid in-mediated binding to the scintillator-containing surface of the flashplate has taken place. This signal derives from the closeness of the radioactive label to the scintillator in the surface of the well of the flashplate. Unphosphorylated substrate causes no signal because it contains no radiolabeled phosphate groups. Free [y-33P]ATP remaining unbound in the solution (supernatant) is washed out of the wells of the flashplates and therefore makes no significant contribution to a background signal. The measured signals are therefore a measure of the ALK1 kinase activity. Measurement takes place in a Perkin-Elmer top count apparatus or a Perkin-Elmer ViewLux instrument.
Material:
Enzyme: commercially available recombinant human ALK4 kinase (amino acids, 150-505), fused to GST at the N terminus, expressed by recombinant baculoviruses in Sf21 insect cells (Upstate Biotechnology, Dundee, Scotland;
Cat#14-614MG), Lot#28232U; aliquots are stored at -80 C; diluted enzyme working solution, 2.5 ng/pl ALK1 (in assay buffer) is freshly prepared and stored on ice until used.
Substrate: biotinylated bovine a-casein. Unbiotinylated casein from Sigma is biotinylated by standard methods using a biotin-N-hydroxysuccinimide (NHS) ester.
Substrate working solution: 0.83 pM ATP, 1.67 pM biotinylated a-casein, 7.4 nCi of [y-331=]ATP/p1 in assay buffer Assay plates: 384-well plates, small volume, white, Greiner (# 784075) Flashplates: streptavidin-coated flashplates, Perkin Elmer (384-Well #
SPM410A) ALJ/TDS
=
Assay buffer: 50 mM Tris/HCI pH 8.0, 1 mM MnCl2, 1 mM OTT, 0.01% NP40, 0.5x complete EDTA-free Stop solution: 33.3 pM ATP, 33.3 mM EDTA, 0.07% Triton X-100 in PBS
Saturation solution for flashplates: 100 pM ATP, 0.2% Triton X-100 in PBS
Adhesive film for plates: Greiner (# 676080) Description of assay Protocol for a 5 pl assay (all steps are carried out at 20 C; a CyBi-well pipettor and a multidrop microdispensor is used for pipetting):
1. 50 nl or 250 nlof substance in 100% DMSO
2. addition of 3 pl of substrate working solution using a CyBi-Well pipettor 3. addition of 2 pl of enzyme working solution using a multidrop microdispensor Incubation at room temperature (20 C) for 45 min 4. addition of 15 pl of stop solution using a CyBi-Well pipettor 5. transfer of 18 pl of assay mixture into flashplates** using a CyBi-Well pipettor Incubation at room temperature for at least 3 h or at 4 C overnight in order to allow binding to the streptavidin-coated flashplates.
6. washing of the flashplates three times with 50 pl of PBS without Ca++ and Mg++
each time 7. sealing of the plates with adhesive film 8. measurement in the top count (60 sec/well) **Saturation of the flashplates: the flashplates are preincubated with 50 pl of saturation solution for at least 1 h. 18 pl of this solution are discarded before 18 pl of assay mixture are transferred into the flashplates Final concentrations calculated for a reaction volume of 5 pl: 1 ng of ALK1/well, 1 pM biotinylated oc-casein, 0.5 pM ATP; 22 nCi/well [7-33P]ATP, 1 mM MnC12;
1 mM DTT; 50 mM Tris-HCI, pH 8.0; 0.01% NP40; 0.5x complete EDTA-free; 1%
or 5% DMSO.

ALJ/TDS
The data are normalized (enzyme reaction without inhibitor = 0% inhibition, enzyme reaction in the presence of 10 mM EDTA = 100% inhibition) and IC50 values are calculated using a 4-parameter fit with the aid of an in-house software.
ALK1 transactivation assay In this case, HepG2 cell cultures are transiently transfected with an ALK1 plasnnid (expression vector for the human ALK1 receptor) by known techniques. At the same time, an ID1 reporter plasmid which 1.3 kB (-1370 to +86) of the ID1 promoter upstream of the luciferase gene is cotransfected. ID1 is a known target gene of ALK1 and is therefore transactivated by cotransfection with the ALK1 receptor. The specific transactivation is quantified by ("relative light units", RLU) which are detected depending on the luciferase. A commercially available kit for detecting luciferase, comprising the substrate luciferin, is used for this.
Material:
HepG2 cells (hepatocellular carcinoma), ATCC HB-8065 96 well culture plates 96 white (Packard # 6005680) 96 well plate polypropylene for compound dilution in DMSO
PBS-; PBS++, DMSO
DMEM Ham's F12 (Biochrom #F4815) with 10% FCS after dialysis, 1% PenStrep and 200 mM Glutamine OPTI MEM (Gibco #51985-026) Fugene (Roche #1814443 1mL) steadyliteHTS (Perkin Elmer# 6016981) Experimental procedure:
Day 1: Seeding of the cells on 96-well plates ALJ/TDS
HepG2 cells are seeded on 96-well plates at a density of 7000 cell/well in DMEM/HamsF12 + 5%FCS (+ 1% PIS, +1% Gln).
Day 2: Transfection of the cells 200 ng DNA: 100 ng ID1-luc (in pGL3basic, Promega)+ 5 ng ALK1wt (in pcDNA3.1) + 95 ng pcDNA3.1 (empty vector, Invitogen) 0.4 pl of fugene 6 pl of OptiMEM
Fugene and OptiMEM are incubated at RT for 5 min. This mixture is incubated with the DNA at RT for 15 minutes.
The plate is then incubated under shaking conditions at RT for 1 hour. After 4 hours at 37 C, the supernatant is aspirated off, and medium (100 p1/well) which Day 3: RLU measurement 100 pl of luciferase substrate (steadyliteHTS, Packard) is added per well, and the Calculation of the IC50:
ALK1wt - DMSO control (without ALK1) = 100%

ALJ/TDS
DU-145 proliferation assay Firstly, DU-145 cells were seeded in a concentration of 200 cells per well in a 96-well microtiter plate (CulturPlate-96, flat bottom transparent) (volume of the culture medium: 100 pl; negative control in starvation medium) and grown under culturing conditions for 18 h. Then 100 pl of the culture medium were removed, and 100 pl of substance solution (dilution in culture medium) were added. The cells are incubated under culturing conditions for 72 h. After the end of the substance treatment, 5 pl of an Alamar Blue labeling solution (Biosource cat # DAL 1100, Lot # 143152SA; dissolved in culture medium) were added (in order to produce a 1:20 dilution) and the cells were grown under culturing conditions for a further 3 h.
The proliferation rate was then analyzed by measurement in an FLx800 (fluorescence measuring instrument from BIO-TEK) at 528 nm and 590 nm in each case.
Cell lines and cell culture Human cell culture lines were used: DU-145 (prostate cell line ATCC No. HTB-81).
All cell lines were grown in 175 cm2 culture bottles at 37 C, 5% CO2 and 95%
humidity and split 1:5 to 1:65 at 80% confluence in accordance with the respective rates of division. For this purpose, the cells were initially washed with 10 ml of PBS
and wetted with 2 ml of trypsin (Gibco). Excess trypsin was removed, and the cells were incubated at room temperature for 10 min. Complete detachment of the treated cells was checked under the microscope. The cells were then taken up in culture medium and transferred in the appropriate volumetric ratio into new cell culture bottles.
DU-145 culture medium:
DMEM HAM's F-12 (from Biochrom AG, cat# F4815) + 1% P/S + 1% glutamin.e +
10% FCS (from Biochrom AG, Lot'0218G) DU-145 starvation medium:
DMEM HAM's F-12 (from Biochrom AG, cat# F4815) + 1% P/S + 1% glutamine ALJ/TDS
Further proliferation assays DNA-replicating cells can be labeled using bromodeoxy uiridine (BrdU) and used as measure of the proliferation of eukaryotic cells. In this method, cells which are in the synthesis phase (S phase) incorporate the thymidine analog BrdU instead of thymidine into the growing DNA chain. The replicated DNA is thus labeled with the modified nucleotide BrdU and can subsequently be detected with the aid of a fluorophore-labeled anti-BrdU antibody. The method was used in order to investigate the effect of substances on cellular proliferation.
Firstly, HeLa cells were seeded in a 96-well microtiter plate in a concentration of io 7500 cells per well (volume: 200 pl) and grown under culturing conditions for 18 h.
Then 100 pl of the culture medium were removed, and 100 pl of substance solution (dilution in culture medium) were added. The cells were incubated under culturing conditions for 6 h, 18 h or 48 h. After the end of the substance treatment, the BrdU-labeling solution (dissolved in culture medium) was added (final concentration of is BrdU 10 pM), and the cells were grown under culturing conditions for a further 3 h.
The BrdU-containing supernatant was then removed, and the cells were washed with PBS. The cells were subsequently fixed with 4% strength formalin solution (dissolved in PBS, 0.1% Triton-X-100) at 4 C for 18 h and washed three times with 200 pl of PBS. In order to make the incorporated BrdU accessible for antibody 20 labeling, the DNA of the cells was digested with nuclease (GE/Amersham).
BrdU
was subsequently detected with the aid of a monoclonal anti-BrdU antibody (GE/Amersham). For this purpose, the fixed cells were incubated with an antibody/nuclease solution (50 p1/well) at 37 C for 45 min and then washed three times with 200 pl of PBS. The fluorescence labeling took place with a fluorophore-25 labeled second antibody which binds to the anti-BrdU antibody. The chromatin of the cell nuclei was stained with Hoechst 33342.
In each case 9 image sections per well were recorded in the various fluorescence channels using an automated microscope (Discovery-1, Molecular Devices), and the BrdU incorporation and the proliferation rate were analyzed by means of a 30 high-content analysis (HCA) method.

ALJ/TDS
Cell lines and cell culture Human cell culture lines were used: HeLa (from cervical carcinoma), PC3 (from prostatic carcinoma) and MCF-7 (from carcinoma of the breast). In addition, CHO
cells (from Chinese hamster ovaries) were cultured.
All cell lines were grown in 175 cm2 culture bottles at 37 C, 5% CO2 and 95%
humidity and split 1:5 to 1:65 at 80% confluence in accordance with the respective rates of division. For this purpose, the cells were initially washed with 10 ml of PBS
and wetted with 2 ml of trypsin (Gibco). Excess trypsin was removed, and the cells were incubated at room temperature for 10 min. Complete detachment of the io treated cells was checked under the microscope. The cells were then taken up in culture medium and transferred in the appropriate volumetric ratio into new cell culture bottles.
HeLa culture medium:
Dulbecco's medium (Gibco), 2 mM glutamine (Gibco), 100 Wm! penicillin (Gibco), 100 pg/ml streptomycin (Gibco) and 10% (v/v) fetal calf serum (PAA) PC3 culture medium:
RPM' 1640 medium (Gibco), 2 mM glutamine (Gibco), 100 U/ml penicillin (Gibco), 100 pg/ml streptomycin (Gibco) and 10% (v/v) fetal calf serum (PAA) MCF-7 culture medium:
RPM' 1640 medium (Gibco), 2 mM glutamine (Gibco), 100 U/ml penicillin (Gibco), 100 pg/ml streptomycin (Gibco) and 10% (v/v) fetal calf serum (PAA), 0.1 nM
estradiol (Sigma) and 0.2 Wm! insulin (Sigma) CHO culture medium:
Ham's F12 medium (PAA), 2 mM glutamine (Gibco), 100 U/m1 penicillin (Gibco), 100 pg/ml streptomycin (Gibco) and 3% (v/v) fetal calf serum (PM) ALJffDS
Further prior art Further prior art is formed by the following publications and the literature cited in these publications:

Gorup et al., Tetrahedron 30 (1974), Byth et al. Bioorganic & Medicinal 2251-2256 Chemistry Letters 14 (2004) 2249-2252 Polanc et al., J. Heterocyclic Chemistry Watanabe et al, Synthesis 11 (1977), (1973), 565-567 761-763 Bioorganic & Medicinal Chemistry Bioorganic & Medicinal Chemistry Letters 2006,1353 Letters 2005,1943 Bioorganic & Medicinal Chemistry Journal of Medicinal Chemistry 2005, Letters 2004 ,6095 7604 ALJ/TDS
Priorities of the present application:
The present patent application claims the priority of German patent application DE 10 2005 042 742.1 (date of filing: Sept. 2,2005), and it also claims all the advantages of filing of the US patent application 60/713 333 (date of filing:
Sept. 2, 2005, provisional application).
The independent claims of the priority application read as follows:
1. A compound of the formula I
Formel R1, 14 N N.

where is aryl or heteroaryl;
A and B are identical or different and are selected from the group consisting of i) H, Hal, -OH, -NR3R4, -CN, or -NO2, ii) optionally mono- or poly-Hal-, -OH-, C3-C6-heterocycloalkyl-, -NR3R4-, or -(C0)-NR3-L-substituted C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl, where the C3-C6-heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(00)- or -(SO2)- groups and/or one or more double bonds, and iii) -NR3(C0)-L, -NR3(C0)-NR3-L, -(C0)-R6, -0-(CH2)p-R6, -(C0)-(NR3)-L, -NR3(CS)-NR3R4 or -0-(CH2)p-aryl, where the substituents in the case of polysubstitution may be identical or different, ALJ/TDS
A and B in addition or alternatively to the aforementioned definition together form a Q-fused C5-C7-cycloalkyl or C5-C7-heterocycloalkyl ring, where the latter comprises at least one oxygen or one nitrogen atom in the ring, and may optionally comprise additionally in the ring one or more oxygen, nitrogen or sulfur atoms and/or one or more ¨(CO)- or ¨(SO2)- groups and/or optionally one or more double bonds, is 0 to 4, is optionally mono- or poly-C1-C6-alkyl-, C1-C6-hydroxyalkoxy-, C1-C6-alkoxyalkoxy, C3-C6-heterocycloalkyl-, or -NR3R4-substituted C1-C6-alkyl, or C3-C6-cycloalkyl or C3-C6-heterocycloalkyl, where the C3-C6 heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or one or more double bonds;
R1 and R2 are identical or different and are selected from the group consisting of j) ¨H
and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3R4-, -NR3(C0)-L- or -NR3COOR7-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
R1 and R2 in addition or alternatively to the aforementioned definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally comprise additionally in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or ¨(SO2)- groups and/or optionally one or more double ALJ/TDS
bonds, where the ring formed by R1 and R2 may be optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, -NR3R4, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
R3 and R4 are identical or different and are selected from the group consisting of j) -H, and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(C0)-or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
R3 and R4 in addition to the aforementioned definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally comprise additionally in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(00)- or ¨(SO2)- groups and/or optionally one or more double bonds, where the ring formed by R3 and R4 may be optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, or by -NR6R7, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
R6 and R7 are identical or different and are selected from the group consisting of j) -H and jj) optionally mono- or poly-Hal-, -OH-, -CN-substituted C1-C6-ALJ/TDS
alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may comprise in the ring optionally one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different, and the isomers, diastereomers, enantiomers and salts thereof.
2. The compound as claimed in claim 1, where R1 and R2 are identical or different and selected from the group consisting of j) ¨H and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl, -(C0)-R6-, -NR3R4-, -NR3(C0)-L- or -NR3COOR7-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(C0)- or -SO2- groups and/or one or more double bonds, where the substituents may in the case of polysubstitution be identical or different, and where R1 and R2 in addition or alternatively to the preceding definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or ¨(SO2)- groups and/or optionally one or more double bonds, where the ring formed by R1 and R2 may be optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C3-C6-cycloalkyl, Cl-C6-hydroxyalkyl, Cl -C6-alkoxyalkyl, -NR3R4, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents may in the case of polysubstitution be identical or different.
3. The compound as claimed in claim 1 or 2, wherein R1 and R2 are identical or different and selected from the group consisting of j) ¨H and jj) optionally A L.I/TD S
mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryloxy-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3R4-, -NR3(C0)-L- or -NR3COOR7-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, where the group aryl or heteroaryl defined in jj) may be substituted as long as alkyl is not involved, where the substituents may in the case of polysubstitution be identical or different, and where R1 and R2 in addition or alternatively to the preceding definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(C0)- or -(S02)-groups and/or optionally one or more double bonds, where the ring formed by R1 and R2 is optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, -NR3R4, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents may in the case of polysubstitution be identical or different.
4. The compound as claimed in claim 3, where Q is -OH-, -Hal-, -CN-, alkyl-, -0R6- or -NR3R4-substituted phenyl, pyridyl, pyrimidinyl, thiophenyl, furyl, imidazolyl, or pyrazolyl.
5. The compound as claimed in claim 4, where R1 and R2 are identical or different and selected from the group consisting of -H, NR3R4-substituted C1-C4-alkyl, optionally additionally substituted one or more times by -Hal, -OH, -CN, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, C3-C6 heterocycloalkyl, C2-C6-alkynyl, aryl, aryloxy, heteroaryl, -S-C1-C6-alkyl, -(C0)-R6, -NR3(C0)-L, or -NR3COOR7, where R3 and R4 may optionally, identically or differently, be C1-C6-alkyl, where R3 and R4 may together form a ALJ/TDS
C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(C0)- or -(SO2)- groups and/or optionally one or more double bonds, and where R6 and R7 is identically or differently -H, -OH, C1-C6-alkoxy, or C1-C3-alkyl.
6. The compound as claimed in any of claims 4, where R1 is selected from the group consisting of ¨H and C1-C3-alkyl, where R2 is selected from the group consisting of NR3R4-substituted C3-C4 alkyl, optionally additionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3(C0)-L- or -NR3COOR7-substituted, where R3 and R4 are identically or differently optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, where R3 and R4 may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or optionally one or more double bonds, and where R6 and R7 is identically or differently -H, -OH, C1-C6-alkoxy, or C1-C3 alkyl.
7. The compound as claimed in claim 1, namely:
(3-phenylimidazo[1,2-14yridazin-6-y1)-(3-pyrrolidin-l-ylpropyl)amine (3-morpholin-4-ylpropyI)-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine (3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-y1)-(3-pyrrolidin-1-ylpropyl)amine (3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-y1)-(3-morpholin-4-ylpropyl)amine [3-(1-methyl-1 H-pyrazol-4-yl)imidazo[1 , 2-b]pyridazi n-6-yl]pyrid in-3-ylmethylamine A LJ/TDS
(3-phenylimidazo[1 ,2-1D]pyridazin-6-yl)pyridin-3-ylmethylamine (3-imidazol-1-ylpropy1)-(3-phenylimidazo[1 ,2-1Apyridazin-6-yl)amine (4-fluorobenzyI)-(3-phenylimidazo[1 ,2-1D]pyridazin-6-y0amine cyclohexylmethyl(3-phenylimidazo[1,2-b]pyridazin-6-y1)amine (2,4-difluorobenzy1)-(3-phenylimidazo[1,2-13]pyridazin-6-y1)amine [3-(5-methy1-1H-pyrazol-4-yl)propyl]-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine 142-(3-phenylimidazo[1 ,2-b]pyridazin-6-ylamino)ethyllimidazolidin-2-one (2-morpholin-4-ylethyl))-(3-phenylimidazo[1 ,2-b]pyridazin-6-yl)amine N*1 ,N*1*-diethyl-N*4-(3-phenylimidazo[1,2-b]pyridazin-6-y1)pentane-1,4-diamine N,N-diethyl-N"-(3-phenylimidazo[1,2-Npyridazin-6-y1)propane-1,3-diamine (3-phenylimidazo[1,2-b]pyridazin-6-y1)-(2-pyrrolidin-1-ylethyl)amine [3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yllpyridin-3-ylmethylamine [3-(3-chlorophenyl)imidazo[1 ,2-b]pyridazin-6-y1]-(3-imidazol-1-ylpropyl)amine 3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-y1)-(4-fluorobenzyl)amine 3-(3-chlorophenypimidazo[1,2-Npyridazin-6-yl)cyclohexylmethylamine 3-(3-chlorophenypimidazo[1,2-b]pyridazin-6-y1)-(2,4-difluorobenzyl)amine 1-1243-(3-phenypimidazo[1,2-b]pyridazin-6-ylamino]ethyl}imidazolidin-2-one N*4*-[3-(3-chlorophenypimidazo[1,2-b]pyridazin-6-y1]-N*1*,N*1*-diethylpentane-1,4-diamine N"-[3-(3-chlorophenypimidazo[1 ,2-b]pyridazin-6-y11-N,N-diethylpropane-1 ,3-diamine [3-(3-chlorophenyl)imidazo[1 ,2-b]pyridazin-6-yI]-(2-pyrrolidin-1 -ylethypamine ALJ/TDS
(3-imidazol-1-ylpropy1)43-(1 -methyl-I H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yliamine (4-fluorobenzyl)-[341 -methyl-I H-pyrazol-4-yl)imidazo[1,2-13]pyridazin-6-yljamine cyclohexylmethy11341-methyl-1 H-pyrazol-4-yl)imidazo[1,2-Npyridazin-6-yl]amine (2,4-difluorobenzy1)4341 -methyl-I H-pyrazol-4-yl)imidazo[1,2-1Apyridazin-6-yl]amine [341-methy1-1 H-pyrazol-4-Aimidazo[1,2-1Apyridazin-6-y1H5-methyl-1 H-pyrazol-4-yl)propyljamine 1 421341 -methyl-I H-pyrazol-4-yl)imidazo[1 ,2-b]pyridazin-6-ylaminolethyl}imidazolidin-2-one (341-methy1-1 H-pyrazol-4-yl)imidazo[1,2-13]pyridazin-6-y1)-(2-morpholin-4-ylethypamine N*1 ,N*1*-diethyl-N*44341 -methyl-1 H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]pentane-1 ,4-diamine N,N-diethyl-N '4341-methyl-I H-pyrazol-4-yl)imidazo[1 ,2-b]pyridazin-6-yl]propane-1,3-diamine [3-( 1 -methyl-I H-pyrazol-4-yl)imidazo[1 ,2-b]pyridazin-6-yI]-(2-pyrrolidin-1-ylethyl)amine pyridin-3-ylmethy143-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine (4-fluorobenzy1)-(3-thiophen-3-ylimidazo[1,2-1Apyridazin-6-yl)amine cyclohexylmethy1(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine (2,4-difluorobenzyI)-(3-thiophen-3-ylimidazo[1 ,2-b]pyridazin-6-ypamine [345-methyl-1 H-pyrazol-4-yl)propyl]-(3-thiophen-3-ylimidazo[1 ,2-b]pyridazin-6-yl)amine 1 [243-thiophen-3-ylimidazo[1 ,2-b]pyridazin-6-ylamino)ethyl]imidazolidin-2-one (2-morpholin-4-ylethyl)-(3-thiophen-3-ylimidazo[1,2-1Apyridazin-6-yl)amine ALJ/TDS
N*1 ,N*1*-diethyl-N*443-thiophen-3-ylimidazo[l ,2-b]pyridazin-6-yl]pentane-1,4-diamine N,N-diethyl-N"-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl]propane-1,3-diamine (2-pyrrolidin-l-ylethyl)-(3-thiophen-3-ylimidazo[1,2-14yridazin-6-y1)amine 8. A method for preparing a compound as claimed in any of claims 1 to 7, with the following stages of the method:
Al) 3-amino-6-halopyrazine is reacted with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, pa A2) the product from stage Al is reacted with N-bromosuccinimide to give a 3-bromo-6-haloimidazo[l ,2-b]pyridazine, A3) the product from stage A2 is converted by reaction with a compound NHR1R2 in a Buchwald-Hartwig cross-coupling reaction into a (3-bromoimidazo[1,2-b]pyridazin-6-y1)-(R1)-(R2)-amine, A4) the product from stage A3 is reacted for example with a boronic acid which is optionally substituted by the radicals A and B to give the compound according to the general formula I, or B1) 3-amino-6-halopyrazine is reacted with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, B2) the product from stage B1 is reacted with N-bromosuccinimide to give a 3-bromo-6-haloimidazo[1,2-b]pyridazine, B3) the product from stage B2 is reacted for example with a boronic acid which is optionally substituted by the radicals A and B to give the compound according to the general formula II, ALJ/TDS
B4) the product from stage B3 is converted by reacting with a compound NHR1R2 in a Buchwald-Hartwig cross-coupling reaction into the compound according to the general formula I, or Cl) 3-amino-6-halopyrazine is reacted with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, C2) the product from stage Cl is converted by reacting with a compound NHR1R2 in a Buchwald-Hartwig cross-coupling reaction into an imidazo[1,2-b]pyridazin-6-y1)-(R1)-(R2)-amine, C3) the product from stage C2 is reacted with N-bromosuccinimide to give a (3-bromoimidazo[1,2-b]pyridazin-6-yI)-(R1)-(R2)-amine, C4) the product from stage C3 is reacted for example with a boronic acid which is optionally substituted by the radicals A and B to give the compound according to the general formula I.
9. The use of a compound as claimed in any of claims 1 to 7 for producing a pharmaceutical composition.

10. The use of a compound as claimed in any of claims 1 to 7 for inhibiting a cellular kinase, in particular a kinase from the group of the protein kinase C

family such as, for example, PKC theta, delta, iota, alpha and zeta.

11. The use of a compound as claimed in any of claims 1 to 7 for producing a pharmaceutical composition for the treatment or for the prophylaxis of a disorder which is associated with overexpression or mutation of a cellular kinase, in particular a cellular kinase according to claim 10.

12. The use as claimed in claim 9, where the disorder is a disorder from the group consisting of "epidermal hyperproliferation such as psoriasis, Alzheimer's, autoinflammatory disorders, Crohn's disease, exaggerated ALJ/TDS
immune response, contact dermatitis, atopic dermatitis, multiple sclerosis, ALS, diabetes, asthma".

13. The use as claimed in claim 9 for modulating, in particular reducing, an immune response, for example after a transplantation has taken place to avoid rejection of an organ.

14. A method for producing a pharmaceutical composition, where a physiologically effective dose of a compound as claimed in any of claims 1 to 7 is mixed with at least one pharmaceutical excipient, and a dosage form is manufactured.
io 15. A method for the treatment or prophylaxis of a disorder which is associated with overexpression or mutation of a cellular kinase, in particular a disorder according to claim 12, where a pharmaceutical composition comprising a physiologically effective dose of a compound as claimed in any of claims 1 to 7 is administered to a person suffering from or under threat of suffering from the disorder.
16. An intermediate according to formula I la R1,N,-rf-N-N-.N?

General formula Ila where Y is replaced by -H or -Hal, R1 and R2 are identical or different and selected from the group consisting of j) ¨H and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-ALJ/TDS
alkynyl-, aryl-, aryloxy-, heteroaryl-, -S-C1-C6-alkyl-, -(C0)-R6-, -NR3R4-, -NR3(C0)-L- or -NR3COOR7-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
R1 and R2 in addition or alternatively to the preceding definition may together io form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(00)- or -(SO2)- groups and/or optionally one or more double bonds, where the ring formed via R1 and R2 may be optionally substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, -NR3R4, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
R3 and R4 are identical or different and selected from the group consisting of j)¨H
and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(C0)-or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;

ALJ/TDS
R3 and R4 in addition or alternatively to the preceding definition may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or optionally one or more double bonds, where the ring formed by R3 and R4 may optionally be substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl or by -NR6R7, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents in the case of polysubstitution may be identical or different;
R6 and R7 are identical or different and selected from the group consisting of j)¨H
and jj) optionally mono- or poly-Hal-, -OH-, -CN-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionallyt comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different, and the isomers, diastereomers, enantiorners and salts thereof.
17. An intermediate according to general formula lib ALJ/TDS
X N

General formula Ilb Q is aryl or heteroaryl, A and B are identical or different and selected from the group consisting of i) H, Hal, -OH, -NR3R4, -CN or -NO2, ii) optionally mono- or poly-Hal-, -OH-, C3-C6-heterocycloalkyl-, -NR3R4-, or -(C0)-NR3-L-substituted C1-C6-alkyl, C1-C6-alkoxy, C3-C6-cycloalkyl to or C3-C6-heterocycloalkyl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or one or more double bonds, and iii) -NR3(C0)-L, -NR3(C0)-NR3-L, -(C0)-R6, -0-(CH2)p-R6, -(C0)-(NR3)-L, -NR3(CS)-NR3R4, or -0-(CH2)p-aryl, where the substituents in the case of polysubstitution may be identical or different, A and B in addition or alternatively to the preceding definition together form a Q-fused C5-C7-cycloalkyl or C5-C7-heterocycloalkyl ring, where the latter comprises at least one oxygen or nitrogen atom in the ring and may optionally additionally comprise in the ring one or more oxygen, nitrogen or sulfur atoms and/or one or more ¨(C0)- or ¨(SO2)- groups and/or optionally one or more double bonds, is 0 to 4, is optionally mono- or poly-C1-C6-alkyl-, C1-C6-hydroxyalkoxy-, C1-C6-alkoxyalkoxy-, C3-C6-heterocycloalkyl- or -NR3R4-substituted C1-C6-alkyl or C3-C6-cycloalkyl or C3-C6-heterocycloalkyl, where the C3-C6 ALJ/TDS
heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or one or more double bonds;
X is chlorine, bromine, 0-S02-CF3 or 0-S02-C4F9;
R3 and R4 are identical or different and selected from the group consisting of j) ¨H, and jj) optionally mono- or poly-Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-alkoxy-, C1-C6-hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(C0)-R6- or -COOR7-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one more -(C0)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different;
is R3 and R4 may in addition or alternatively to the preceding definition together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and may optionally additionally comprise in the ring one or more nitrogen, oxygen or sulfur atoms and/or one or more -(CO)- or -(SO2)- groups and/or optionally one or more double bonds, where the ring formed via R3 and R4 may optionally be substituted one or more times by -CN, -Hal, -OH, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, or by -NR6R7, -CONR6R7, -(C0)-R6 or -COOR7 and/or by optionally mono- or poly-Hal-, C1-C6-alkoxy- or -(C0)-R6-substituted aryl or heteroaryl, where the substituents may in the case of polysubstitution be identical or different;
R6 and R7 are identical or different and selected from the group consisting of j)¨H
and jj) optionally mono- or poly-Hal-, -OH-, -CN-substituted C1-C6-alkyl, C1-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-ALJ/TDS
heterocycloalkyl, aryl or heteroaryl, where the C3-C6-heterocycloalkyl may optionally comprise in the ring one or more nitrogen, oxygen and/or sulfur atoms and/or one or more -(CO)- or -SO2- groups and/or one or more double bonds, and where the substituents in the case of polysubstitution may be identical or different and the isomers, diastereomers, enantiomers and salts thereof.

Claims

1. A compound of the formula I
wherein Q is aryl or heteroaryl ¨ with the exception of pyrimidine;
A and B are identical or different and independently of one another are each i) H, Hal, -OH, -NR3R4, -CN, or -NO2, ii) C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl that is optionally substituted with at least one substituent which at each occurrence is Hal-, -OH, C3-C6-heterocycloalkyl-, -NR3R4, -SO2NR3R4, -SO2R3 or -(CO)-NR3-L, wherein the C3-C6-heterocycloalkyl optionally comprises in the ring:
at least one nitrogen, oxygen or sulfur atom or any combination thereof, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, or iii) -NR3(CO)-L, -NR3(CO)-NR3-L, -(CO)-R6, -O-(CH2)p-R6, -(CO)-(NR3)-L, -NR3(CS)-NR3R4, -NR3(SO2)-L, -(SO2)-NR3R4, -NR3(CO)NR3R4, -(CO)NR3R4, -CO2R7, -NR3(SO2)R4 or -O-(CH2)p-aryl, or A and B together form a Q-fused C5-C7-cycloalkyl or C5-C7-heterocycloalkyl ring, wherein the latter comprises at least one oxygen or one nitrogen atom in the ring, and optionally comprises additionally in the ring:
at least one oxygen, nitrogen or sulfur atom, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, P is 0 to 4, L is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl that is optionally substituted with at least one substituent which at each occurrence is OH-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-hydroxyalkoxy-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, C1-C6-alkoxyalkoxy-, C3-C6-heterocycloalkyl-, or -NR3R4, wherein the C3-C6 heterocycloalkyl optionally comprises in the ring:
at least one nitrogen, oxygen or sulfur atom, or any combination thereof, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof;
R1 and R2 are identical or different and independently of one another are each j) -H, or jj) C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal, -OH, -CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C6-hydroxyalkyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, C2-C6-alkynyl, aryl, aryloxy, heteroaryl, -S-C1-C6-alkyl, -(CO)-R6, -NR3R4, -NR3(CO)-L, -NR3COOR7, -COOR7, -NR3CONR3R4, -NR3SO2R4, -SO2NR3R4 , -CONR3R4- or -SO2R3, wherein the C3-C6-heterocycloalkyl optionally comprises in the ring:

at least one nitrogen, oxygen or sulfur atom, or any combination thereof, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, or -(CH2)r-R8 radical, wherein r is a number 0-3, and R8 is a radical wherein the aryl, heteroaryl, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl substituent optionally present in R1 or R2 is optionally substituted with at least one substituent which at each occurrence is -Hal, -CN, - OH, -C1-C6-alkyl, C1-C6-haloalkyl, -alkoxy, C1-C6-haloalkoxy, -C1-C6-hydroxyalkyl, -C3-C6-cycloalkyl, -NO2, -NH2, -NR3R4, -CONR3R4, -NR3COR4, NR3SO2R4, -COR6, CO2R7, -SO2NR3R4, -SR3, SOR3, -SO2R3, -OR3, or -O(CH2)p R6, wherein two or more aryl or heteroaryl groups may not be substituents on the same carbon atom in R1 or R2; or R1 and R2 together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and optionally comprises additionally in the ring, at least one nitrogen, oxygen or sulfur atom, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, wherein the ring formed by R1 and R2 is optionally substituted with at least one substituent which at each occurrence is -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, C1-C6-haloalkoxyalkyl, C1-C6-haloalkoxy-, -NR3R4, -CONR6R7, -(CO)-R6 or -COOR7, or aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or -(CO), or any combination thereof, R3 and R4 are identical or different and independently of one another are each j) -H, or jj) C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal-, -OH-, -CN-, C1-C6-alkyl-, C1-C6-haloalkyl-, C1-C6-alkoxy-, C1-C6-haloalkoxy-, hydroxyalkyl-, C3-C6-cycloalkyl-, C3-C6 heterocycloalkyl-, C2-C6-alkynyl-, aryl-, aryloxy-, heteroaryl-, -NR6R7-, -CONR6R7-, -(CO)-R6- or -COOR7, wherein the C3-C6-heterocycloalkyl optionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, or any combination thereof, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, or R3 and R4 together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and optionally comprises additionally in the ring at least one nitrogen, oxygen or sulfur atom, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, wherein the ring formed by R3 and R4 is optionally substituted with at least one substituent which at each occurrence is (a) -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, C1-C6-haloalkoxyalkyl, or C1-C6-haloalkoxy-, (b) -NR6R7, -CONR6R7, -(CO)-R6 or -COOR7, or (c) aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal, C1-C6-alkoxy, C1-C6-haloalkoxy or -(CO)-R6, or (d) any combination thereof, R6 and R7 are identical or different and independently of one another are each j) ¨H, or jj) C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal, -OH, or -CN, wherein the C3-C6-heterocycloalkyl optionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, or any combination thereof, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, or an isomer, diastereomer, enantiomer or salt thereof.

2. The compound as claimed in claim 1, wherein R1 and R2 are identical or different and independently of one another are each j) ¨H, or jj) C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl that is optionally substituted with at least one substituent which at each occurrence is Hal, -OH, -CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, C3-C6 heterocycloalkyl, C2-C6-alkynyl, aryl, aryloxy, heteroaryl, -S-C1-C6-alkyl, -(CO)-R6, -NR3R4, -NR3(CO)-L- or -NR3COOR7, wherein the C3-C6-heterocycloalkyl optionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, or any combination thereof, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, or R1 and R2 together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and optionally additionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, wherein the ring formed by R1 and R2 is optionally substituted with at least one substituent which at each occurrence is (a) -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, C1-C6-haloalkoxyalkyl, C1-C6-haloalkoxy, -NR3R4, -CONR6R7, -(CO)-R6 or -COOR7, or (b) aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or -(CO)-R6, or (c) any combination thereof.

3. The compound as claimed in claim 1, where R1 and R2 are identical or different and independently of one another are j) -H or jj) C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-cycloalkyl, or C3-C6-heterocycloalkyl that is optionally substituted with at least one substituent which at each occurrence is Hal, -OH, -CN, C1-C6-alkyl, C1-C2-haloalkyl, C1-C6-alkoxy, haloalkoxy, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl, aryloxy, heteroaryl, -S-C1-C6-alkyl, -(CO)-R6, -NR3R4, -NR3(CO)-L, -NR3COOR7, -COOR7, -NR3SO2R4, -SO2NR3R4, -CONR3R4 or -SO2R3 or -(CH2)R8 radical where R8 is a radical wherein the aryl, heteroaryl, C3-C6-cycloalkyl or C3-C6-heterocycloalkyl substituent optionally present in R1 or R2 is optionally substituted with at least one substituent which at each occurrence is -Hal, -CN, - OH, -C1-C6-alkyl, -C1-C2-haloalkyl, -C1-C6-alkoxy, -C1-C2-haloalkoxy, -C1-C6-hydroxyalkyl, -C3-C6-cycloalkyl, -NO2, -NH2, -C1-C6-haloalkyl, -NR3R4, -CONR3R4, -NR3COR4, NR3SO2R4, -COR6, CO2R7, -SO2NR3R4, -SR3, SOR3, --SO2R3, -OR3, or -O(CH2)p R6, wherein two or more aryl or heteroaryl groups in R1 or R2 may not be substituents of the same carbon atom.

4. The compound as claimed in claim 1 or 2, wherein R1 and R2 are identical or different and independently of one another are each j) -H, or jj) C1-C6-alkyl, C1-C6-haloalkyl-, C1-C6-alkoxy, C1-C6-haloalkoxy-, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C3-C6-heterocycloalkyl, aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal, -OH, -CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-hydroxyalkyl, cycloalkyl, C3-C6 heterocycloalkyl, C2-C6-alkynyl, aryloxy, -S-C1-C6-alkyl, -(CO)-R6, -NR3R4, -NR3(CO)-L or -NR3COOR7, wherein the C3-C6-heterocycloalkyl optionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, or any combination thereof, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, wherein the aryl or heteroaryl substituent defined in jj) is optionally substituted with the proviso that alkyl is not the substituent, or R1 and R2 together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and optionally additionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, wherein the ring formed by R1 and R2 is optionally substituted with at least one substituent which at each occurrence is (a) -CN, -Hal, -OH, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-hydroxyalkyl, C1-C6-alkoxyalkyl, C1-C6-haloalkoxyalkyl, C1-C6-haloalkoxy, -NR3R4, -CONR6R7, -(CO)-R6 or -COOR7, or (b) aryl or heteroaryl that is optionally substituted with at least one substituent which at each occurrence is Hal-, C1-C6-alkoxy-, C1-C6-haloalkoxy- or -(CO)-R6, or (c) any combination thereof.

5. The compound as claimed in claim 3 or 4, wherein Q is phenyl, pyridyl, thiophenyl, furyl, imidazolyl, or pyrazolyl that is optionally substituted with at least one substituent which at each occurrence is -OH, Hal, -CN, alkyl, -OR6 or -NR3R4.

6. The compound as claimed in claim 5, where R1 and R2 are identical or different and independently of one another are each -H or NR3R4-substituted C1-C4-alkyl, optionally additionally substituted with at least one substituent which at each occurrence is -Hal, -OH, -CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-haloalkoxy, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, C3-C6 heterocycloalkyl, C2-alkynyl, aryl, aryloxy, heteroaryl, -S-C1-C6-alkyl, -(CO)-R6, -NR3(CO)-L, or -NR3COOR7, wherein R3 and R4 may optionally, identically or differently, be C1-alkyl or C1-C6-haloalkyl, wherein R3 and R4 may together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and optionally additionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, and wherein R6 and R7 are each independently -H, -OH, C1-C6-alkoxy, C1-C6-haloalkoxy or C1-C3-alkyl.

7. The compound as claimed in any one of claims 1 to 4, wherein R1 is -H or alkyl, wherein R2 is NR3R4-substituted C3-C4 alkyl that is optionally additionally substituted with at least one substituent which at each occurrence is Hal, -OH, -CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-hydroxyalkyl, cycloalkyl, C3-C6 heterocycloalkyl, C2-C6-alkynyl, aryl, aryloxy, heteroaryl, -alkyl, -(CO)-R6, -NR3(CO)-L or -NRCOOR7, wherein R3 and R4 are each independently C1-C6-alkyl or C1-C6-haloalkyl that is optionally substituted with at least one substituent which at each occurrence is Hal, -OH, -CN, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-hydroxyalkyl, C3-C6-cycloalkyl, C3-C6 heterocycloalkyl, C2-C6-alkynyl, aryl, aryloxy, heteroaryl, -NR6R7, -CONR6R7, -(CO)-R6 or -COOR7, or R3 and R4 together form a C3-C6-heterocycloalkyl ring which comprises at least one nitrogen atom in the ring and optionally additionally comprises in the ring at least one nitrogen, oxygen or sulfur atom, at least one -(CO)- or -(SO2)- group, or at least one double bond, or any combination thereof, and wherein R6 and R7 are each independently -H, -OH, C1-C6-alkoxy, C1-C6-haloalkoxy, or C1-C3 alkyl.

8. The compound as claimed in any one of claims 1 to 7, wherein R1 or R2 is -H.

9. The compound as claimed in claim 1, which is:
(3-phenylimidazo[1,2-b]pyridazin-6-yl)-(3-pyrrolidin-1-ylpropyl)amine;
(3-morpholin-4-ylpropyl)-(3-phenylimidazo[1,2-b]pyridazin-6-y)amine;
(3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)-(3-pyrrolidin-1-ylpropyl)amine;
(3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)-(3-morpholin-4-ylpropyl)amine;
[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]pyridin-3-ylmethylamine;
(3-phenylimidazo[1,2-b]pyridazin-6-yl)pyridin-3-ylmethylamine;
(3-imidazol-1-ylpropyl)-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine;
(4-fluorobenzyl)-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine;
cyclohexylmethyl-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine;
(2,4-difluorobenzyl)-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine;
[3-(5-methyl-1H-pyrazol-4-yl)propyl]-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine;
1-[2-(3-phenylimidazo[1,2-b]pyridazin-6-ylamino)ethyl]imidazolidin-2-one, (2-morpholin-4-ylethyl))-(3-phenylimidazo[1,2-b]pyridazin-6-yl)amine;
N*1,N*1*-diethyl-N*4-(3-phenylimidazo[1,2-b]pyridazin-6-yl)pentane-1,4-diamine;
N,N-diethyl-N'-(3-phenylimidazo[1,2-b]pyridazin-6-yl)propane-1,3-diamine;
(3-phenylimidazo[1,2-b]pyridazin-6-yl)-(2-pyrrolidin-1-ylethyl)amine;
[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]pyridin-3-ylmethylamine;
[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]-(3-imidazol-1-ylpropyl)amine;

3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)-(4-fluorobenzyl)amine;
3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)cyclohexylmethylamine;
3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl)-(2,4-difluorobenzyl)amine;
1-{2-[3-(3-phenyl)imidazo[1,2-b]pyridazin-6-ylamino]ethyl}imidazolidin-2-one;

- 185a -N*4*-[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]-N*1*,N*1*-diethylpentane-1,4-diamine, N'-[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]-N,N-diethylpropane-1,3-diamine;
[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]-(2-pyrrolidin-1-ylethyl)amine;
(3-imidazol-1-ylpropyl)-[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amine;
(4-fluorobenzyl)-[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amine;
cyclohexylmethyl-[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amine, (2,4-difluorobenzyl)-[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]amine, [3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]-[5-methyl-1H-pyrazol-4-yl)propyl]amine;
1-{2-[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-ylamino]ethyl}imidazolidin-2-one;
(3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl)-(2-morpholin-4-ylethyl)amine;
N*1, N*1*-diethyl-N*4-[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]pentane-1,4-diamine;
N,N-diethyl-N'-[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-b]pyridazin-6-yl]propane-1,3-diamine;
[3-(1-methyl-1H-pyrazol-4-yl)imidazo[1 ,2-b]pyridazin-6-yl]-(2-pyrrolidin-1-ylethyl)amine;
pyridin-3-ylmethyl-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine;
(4-fluorobenzyl)-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine;
cyclohexylmethyl-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine;
(2,4-difluorobenzyl)-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine;
[3-(5-methyl-1H-pyrazol-4-yl)propyl]-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine;
1-[2-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-ylamino)ethyl]imidazolidin-2-one, -185b-(2-morpholin-4-ylethyl)-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine;
N*1,N*1*-diethyl-N*413-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl]pentane-1,4-diamine;
N,N-diethyl-N'-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl]propane-1,3-diamine; or (2-pyrrolidin-1-ylethyl)-(3-thiophen-3-ylimidazo[1,2-b]pyridazin-6-yl)amine.

10. The compound as claimed in claim 1, which is:
(3-Phenyl-imidazo[1,2-b]pyridazin-6-yl)-(3-pyrrolidin-1-yl-propyl)-amine;

(3-Morpholin-4-yl-propyl)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
[3-(3-chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(3-pyrrolidin-1-yl-propyl)-amine ;
(3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(3-morpholin-4-yl-propyl)-amine ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-methyl-(3-morpholin -4-yl-propyl)-amine ;
3-[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-pyrrolidine-1-carboxylic acid tert-butyl ester ;

N-{3-[6-(3-Morpholin-4-yl-propylami no)-imidazo[1,2-b]pyridazin-3-yl]-p henyl}-acetamide ;
(S)-N*4*-[3-(3-Chloro-phenyl)-imida zo[1,2-b]pyridazin-6-yl]-N1*,N*1*-diethyl-pentane-1,4-diamine ;
(R)-N*4*-[3-(3-Chloro-phenyl)-imida zo[1,2-b]pyridazin-6-yl]-N*1*,N*1*-diethyl-pentane-1,4-diamine ;
4-[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-piperazine-1-carb oxylic acid tert-butyl ester ;
2-[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-ethanesulfon ic acid dimethylamide ;

N'-[3-(3-Chloro-4-methyl-phenyl)-im idazo[1,2-b]pyridazin-6-yl]-N,N-die thyl-propane-1,3-diamine ;
(2-Pyridin-2-yl-ethyl)-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl-amine ;
1-(3-{6-[(Pyridin-4-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-ethanone ;
1-[3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-phenyl]-ethanone ;
[3-(3,5-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
4-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;

(Tetrahydro-pyran-4-yl)-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine;
(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(tetrahydro-pyran-4-yl)-amine ;
[3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
[3-(2-Methoxy-pyridin-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine;
[3-(3-Methanesulfonyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
[3-( 1 -Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-3-ylmethyl-amine ;

(3-Phenyl-imidazo[1,2-b]pyridazin-6 -yI)-pyridin-3-ylmethyl-amine;
(3-Imidazol-1-yI-propyl)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yl)-amine;
(4-Fluoro-benzyI)-(3-phenyl-imidazo [1,2-b]pyridazin-6-yI)-amine;
Cyclohexylmethyl-(3-phenyl-imidazo [1,2-b]pyridazin-6-yI)-amine;
(2,4-Difluoro-benzyI)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yI)-amine;

[3-(5-Methyl-1H-pyrazol-4-yl)-propyl]-(3-phenyl-imidazo[1,2-b]pyridazin-6-yl) -amine;
1-[2-(3-Phenyl-imidazo[1,2-b]
pyridazin-6-ylamino)-ethyl]-imidazolidin-2-one;
(2-Morpholin-4-yl-ethyl)-(3-phenyl-imidazo[1,2-b]pyridazin-6-yl)-amine;
N*1*,N*1*-Diethyl-N*4*-(3-phenyl-imidazo[1,2-b]pyridazin-6-yl)-pentane N,N-Diethyl-N'-(3-phenyl-imidazo [1,2-b]pyridazin-6-yl)-propane-1,3-diamine ;
(3-Phenyl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyrrolidin-1-yl-ethyl)-amine ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-pyridin-3-ylmethyl-amine ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(3-imidazol-1-yl-propyl)-amine ;

[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(4-fluoro-benzyl)-amine ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-cyclohexylmethyl-amine ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(2,4-difluoro-benzyl)-amine ;
1-{2-[3-(3-Chloro-phenyl)-imidazo [1,2-b]pyridazin-6-ylamino]-ethyl)-imidazolidin-2-one ;

N*4*-[3-(3-Chloro-phenyI)-imidazo [1 ,2-b]pyridazin-6-yl]-N*1*,N*1*-diethyl-pentane-1,4-diamine N'-[3-(3-Chloro-phenyI)-imidazo [1,2-b]pyridazin-6-yI]-N,N-diethyl-propane-1 ,3-diamine [3-(3-Chloro-phenyl)-imidazo [1 ,2-b] pyridazin-6-yI]-(2-pyrrolidin-1-yI-ethyl)-amine (3-Imidazol-1 -yl-propyI)-[3-(1-methyl-1H -pyrazol-4-yI)-imidazo [1 ,2-b] pyridazin-6-yI)-amine (4-Fluoro-benzyl)-(3-(1 -methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]-pyridazin-6-yl]-amine Cyclohexylmethyl-[3-(1 -methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yI]-amine (2,4-Difluoro-benzyl)-[3-(1 -methyl-1H-pyrazol-4-yl)-imidazo[1 ,2-b]-pyridazin-6-yl]-amine [3-(1 -Methyl-1 H-pyrazol-4-yl)-imidazo-[1,2-b]pyridazin-6-yl]-[3-(5-methyl-1H-pyrazol-4-yl)-propyl]-amine 1-{2-[3-(1 -Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-ethyl}-imidazolidin-2-one [3-(1 -Methyl-1 H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-morpholin-4-yl-ethyl)-amine N*1*,N*1*-Diethyl-N*4*-[3-(1-methyl -1 H-pyrazol-4-yl)-imidazo[1,2-b]-pyridazin-6-yl]-pentane-1,4-diamine N,N-Diethyl-N'-[3-(1 -methyl-1 H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-propane-1,3-diamine [3-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyrrolidin-1-yl-ethyI}-amine Pyridin-3-ylmethyl-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine (3-Imidazol-1-yl-propyl)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine (4-Fluoro-benzyI)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yI)-amine Cyclohexylmethyl-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
(2,4-Difluoro-benzyl)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
[3-(5-Methyl-1H-pyrazol-4-yl)-propyl]-(3-thiophen-3-yl-imidazo-[1,2-b]pyridazin-6-yl)-amine ;
1-[2-(3-Thiophen-3-yl-imidazo-[1,2-b]pyridazin-6-ylamino)-ethyl]-imidazolidin-2-one ;

(2-Morpholin-4-yl-ethyl)-(3-thiophen-3-yl-imidazo[1,2-b]
pyridazin-6-yl)-amine ;
N*1*,N*1*-Diethyl-N*4*-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-pentane-1,4-diamine ;
N,N-Diethyl-N'-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-propane-1,3-diamine ;
(2-Pyrrolidin-1-yl-ethyl)-(3-thiophen-3-yl-imidazo[1,2-b]-pyridazin-6-yl)-amine ;

[3-(3-Methoxy-phenyI)-imidazo[1,2-b ]pyridazin-6-yI]-methyl-(2-pyridin-2-yl-ethyl)-amine Methyl-(2-pyridin-2-yl-ethyl)-[3-(3 -trifluoromethoxy-phenyl)-imidazo[1 ,2-b]pyridazin-6-yI]-amine [3-(3,4-Dichloro-phenyI)-imidazo[1, 2-b]pyridazin-6-yl]--methyl-(2-pyrid in-2-yl-ethyl)-amine [3-(3-Chloro-4-fluoro-phenyl)-imida zo[1,2-b]pyridazin-6-yl]-methyl-(2-pyridin-2-yl-ethyl)-amine Methyl-(3-naphthalen-2-yI-imidazo[1 ,2-b]pyridazin-6-yI)-(2-pyridin-2-y I-ethyl)-amine [3-(3-Methoxy-phenyI)-imidazo[1,2-b ]pyridazin-6-yI)-(2-pyridin-2-yl-et hyl)-amine [3-(3,4-Dichloro-phenyI)-imidazo[1, 2-b]pyridazin-6-yI]-(2-pyridin-2-yl -ethyl)-amine 3-[6-(2-Pyridin-2-yl-ethylamino)-im idazo[1,2-b]pyridazin-3-yI]-benzoni trile (3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(2-(6-methyl-pyridi n-2-yl-ethyl]-amine [2-(6-Methyl-pyridin-2-yl)-ethyl]-[
3-(3-trifluoromethoxy-phenyI)-imida zo[1,2-b)pyridazin-6-yI]-amine [2-(6-Methyl-pyridin-2-yl)-ethyl]-( 3-naphthalen-2-yl-imidazo[1,2-b]pyr idazin-6-yI)-amine (3-(3,4-DichIoro-phenyl)-imidazo[1, 2-b]pyridazin-6-yl]-[2-(4-methyl-py ridin-2-yl)-ethyl]-amine [2-(4-Methyl-pyridin-2-yl)-ethyl]-( 3-naphthalen-2-yl-imidazo[1,2-b]pyr idazin-6-yl)-amine ;
[2-(3-Methyl-pyridin-2-yl)-ethyl]-[
3-(3-trifluoromethoxy-phenyl)-imida zo[1,2-13]pyridazin-6-yl]-amine ;
[3-(3-Methoxy-phenyl)-imidazo[1,2-b ]pyridazin-6-yl]-[2-(5-methyl-pyrid in-2-yl)-ethyl]-amine ;
[2-(5-Methyl-pyridin-2-yl)-ethyl]-[
3-(3-trifluoromethoxy-phenyl)-imida zo[1,2-b]pyridazin-6-yl]-amine ;

[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-b]pyridazin-6-yl]-(2-(5-methyl-py ridin-2-yl)-ethyl]-amine ;
[3-(3-Chloro-4-fluoro-phenyl)-imida zo[1,2-b]pyridazin-6-yl]-[2-(5-meth yl-pyridin-2-yl)-ethyl]-amine ;
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-b]pyridazin-6-yl]-[2-(3-methyl-py ridin-2-yl)-ethyl]-amine ;
[3-(3,4-Dichloro-phenyl)-imidazo[1, 2-b]pyridazin-6-yl]-(2-(6-methyl-py ridin-2-yl)-ethyl]-amine ;

[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yI]-(2-pyrazin-2-yl-eth yI)-amine [3-(3-Methoxy-phenyl)-imidazo[1,2-b ]pyridazin-6-yI]-(2-pyrazin-2-yl-et hyl)-amine [3-(3-Chloro-4-fluoro-phenyl)-imida zo[1,2-b]pyridazin-6-yI]-(2-pyrazin -2-yl-ethyl)-amine (3-Naphthalen-2-yl-imidazo[1,2-b]py ridazin-6-yI)-(2-pyrazin-2-yl-ethyl )-amine (3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yI]-[2-(4-methyl-pyridi n-2-yI)-ethyl]-amine <1MG>
[2-(4-Methyl-pyridin-2-yl)-ethyl]-[
3-(3-trifluoromethoxy-phenyI)-imida zo[1,2-b]pyridazin-6-yl]-amine [3-(3-Chloro-4-fluoro-phenyl)-imida zo[1,2-b]pyridazin-6-yI]-[2-(4-meth yI-pyridin-2-yl)-ethyl]-amine [3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yI]-(2-pyrazol-1-yl-eth yI)-amine [3-(3-Methoxy-phenyI)-imidazo[1,2-b ]pyridazin-6-yI]-(2-pyrazol-1-yl-et hyl)-amine (2-Pyrazol-1-yI-ethyl)-[3-(3-triflu oromethoxy-phenyI)-imidazo[1,2-b]py ridazin-6-yl]-amine (3-(3,4-Dichloro-phenyl)-imidazo[1, 2-b]pyridazin-6-yI]-(2-pyrazol-1-yl -ethyl)-amine 3-[6-(2-Pyrazol-1-yl-ethylamino)-im idazo[1,2-b]pyridazin-3-yl]-benzoni trile ;

[3-(3-Chloro-4-fluoro-phenyI)-imida zo[1,2-b]pyridazin-6-yl]-(2-pyrazol -1-yl-ethyl)-amine (3-Naphthalen-2-yI-imidazo[1,2-b]py ridazin-6-yl)-(2-pyrazol-1-yl-ethyl )-amine [2-(1-Methyl-1H-imidazol-4-yl)-ethy l]-(3-(3-trifluoromethoxy-phenyl)-i midazo[1,2-b]pyridazin-6-yl]-amine 3-{6-[2-(1-Methyl-I H-imidazol-4-yl) -ethylamino]-imidazo[1,2-b]pyridazi n-3-yI)-benzonitrile;

[2-(1-Methyl-1H-imidazol-4-yl)-ethy l]-(3-naphthalen-2-yl-imidazo[1,2-b ]pyridazin-6-yI)-amine [3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(2-[1,2,4]triazol-1 -yl-ethyl)-amine;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-methyl-(2-pyridin-2 -yl-ethyl)-amine (4-[6-(2-Hydroxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol;
4-[6-((R)-2-Hydroxy-1-methyl-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol;

2-[3-(3-Methanesulfonyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-ethanol;
2-[3-(3-Methylsulfanyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-ethanol;
[3-(1H-1ndol-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl]-ethyl)-amine ;
(2-Pyridin-3-yl-ethyl)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine;
[3-(3-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl-ethyl)-amine;

(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-2-yl-ethyl)-amine ;
[3-(4-Chloro-phenyI)-imidazo[1,2-b]
pyridazin-6-yI]-(2-pyridin-2-yl-eth yl)-amine ;
[3-(3,4-Dimethyl-phenyI)-imidazo[1, 2-b]pyridazin-6-yI]-(2-pyridin-2-yI
-ethyl)-amine ;
(2-Pyridin-2-yl-ethyl)-[3-(3-trifluoromethoxy-phenyl)-imidazo[1 ,2-b]]pyridazin-6-yl]-amine ;
[3-(3-Chloro-4-fluoro-phenyl )imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl-ethyl)-amine ;

[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-2-yl-ethyl)-amine ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]
pyridazin-6-yl]-(2-pyridin-3-yl-eth yl)-amine ;
(2-Pyridin-2-yl-ethyl)43-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
[3-(3-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-2-yl-ethyl)-amine ;
[3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-2-yl-ethyl)-amine ;

[3-(4-Methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-2-yl-ethyl)-amine ;
4-[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol ;
1-{3-[6-(2-Pyridin-2-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-ethanone ;
N-{3-[6-(2-Pyridin-2-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanesulfonamide ;
4-[6-(2-Pyridin-2-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzonitrile ;

(2-Pyridin-2-yl-ethyl)-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
(3-Phenyl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-2-yl-ethyl)-amine ;
(3-Naphthalen-1-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-2-yl-ethyl)-amine ;
(3-Benzofuran-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-2-yl-ethyl)-amine ;
[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-2-yl-ethyl)-amine ;

(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-2-yl-ethyl)-amine ;
(3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-2-yl-ethyl)-amine ;
[3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-2-yl-ethyl)-amine ;
(2-Pyridin-3-yl-ethyl)-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
[3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl-ethyl)-amine ;

(3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-3-yl-ethyl)-amine [3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl-ethyl)-amine [3-(4-Methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl-ethyl)-amine;
(3-Benzofuran-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-3-yl-ethyl)-amine (3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-3-yl-ethyl)-amine ;
(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-3-yl-ethyl)-amine ;
(3-Phenyl-imidazo[1,2-b]pyridazin-6-yl)-(2-pyridin-3-ykethyl)-amine ;
[3-(4-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl-ethyl)-amine ;
4-[6-(2-Pyridin-3-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-yI]-benzonitrile ;

(2-Pyridin-3-yl-ethyl)-{3-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine;
[3-(1-Methyl-1H-pyrazol-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-pyridin-3-yl-ethyl)-amine;
(2-Pyridin-3-yl-ethyl)-(3-thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-amine;
N-{3-[6-(2-Pyridin-3-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanesulfonamide [3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-furan-2-ylmethyl-amine;

Furan-2-ylmethyl-(3-phenyl-imidazo[1,2-b]pyridazin-6-yI)-amine ;
Furan-2-ylmethyl-[3-(4-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Furan-2-ylmethyl-[3-(1H-indol-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-furan-2-ylmethyl-amine ;
Furan-2-ylmethyl-[3-(3-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;

N-(3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-acetamide ;
(3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-methanol ;
4-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenol ;
3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenol ;
3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-benzamide ;

N-(3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-methanesulfonamide ;
4-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-2-methoxy-phenol 1-(3-{6-[(Furan-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-ethanone ;
Furan-2-ylmethyl-[3-(6-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Furan-2-ylmethyl-(3-pyridin-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;

Furan-2-ylmethyl-[3-(5-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine Furan-2-ylmethyl-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yI)-amine [3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-thiophen-2-ylmethyl-amine Thiophen-2-ylmethyl-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine 1-(3-{6-[(Thiophen-2-ylmethyl)-amino)-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-ethanone 3 3-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenol ;
[3-(5-Methoxy-pyridin-311)-imidazo[1,2-b)pyridazin-6-yl]-thiophen-2-ylmethyl-amine ;
(4-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl]-phenyl)-methanol -) N-(2-Hydroxy-ethyl)-3-{6-[(thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-benzamide ;

[3-(4-Methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-thiophen-2-ylmethyl-amine (3-Thiophen-2-yl-imidazo[1,2-b]-pyridazin-6-yl)-thiophen-2-ylmethyl-amine (3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-thiophen-2-ylmethyl-amine [3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-thiophen-2-ylmethyl-amine [3-(1H-Indo1-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-thiophen-2-ylmethyl-amine ;
[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-thiophen-2-ylmethyl-amine ;
[3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-thiophen-2-ylmethyl-amine ;
[3-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl}-thiophen-2-ylmethyl-amine ;
(3-Pyridin-3-yl-imidazo[1,2-b]pyridazin-6-yl)-thiophen-2-ylmethyl-amine ;

N-(3-{6-[(Thiophen-2-ylmethyl)-amino}-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-acetamide ;
[3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-thiophen-2-ylmethyl-amine ;
4-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenol ;
(3-Pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-thiophen-2-ylmethyl-amine ;
2-Methoxy-4-{6-[(thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenol ;

3-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-benzamide ;
N-(3-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenyl)-methanesulfonamide ;
4-{6-[(Thiophen-2-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-benzoic acid ;
[3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-4-ylmethyl-amine ;
Pyridin-4-ylmethyl-[3-(3-trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl)-amine ;

[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-4-ylmethyl-amine ;
Pyridin-4-ylmethyl-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl)-pyridin-4-ylmethyl-amine ;
(3-Benzofuran--2-yl-imidazo[1,2-b]pyridazin-6-yl)-pyridin-4-ylmethyl-amine ;
[3-(3,4-Dimethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-4-ylmethyl-amine ;

Pyridin-4-ylmethyl-(3-p-toly-imidazo[1,2-b]pyridazin-6-yl)-amine , Pyridin-4-ylmethyl-(3-thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ) (3-Phenyl-imidazo[1,2-b]pyridazin-6-yl)-pyridin-4-ylmethyl-amine (3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-pyridin-4-ylmethyl-amine ;
(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-pyridin-4-ylmethyl-amine ;

Pyridin-2-ylmethyl-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
[3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]pyridin-2-ylmethyl-amine ;
(3-Benzofuran-2-yl-imidazo[1,2-b]pyridazin-6-yl)-pyridin-2-ylmethyl-amine ;
(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-pyridin-2-ylmethyl-amine ;

[3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-2-ylmethyl-amine ;
(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-pyridin-2-ylmethyl-amine ;
Pyridin-2-ylmethyl-[3-(3-trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Pyridin-2-ylmethyl-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
Pyridin-2-ylmethyl-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;

[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-2-ylmethyl-amine ;
[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-2-ylmethyl-amine ;
[3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-2-ylmethyl-amine ;
[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-pyridin-2-ylmethyl-amine ;
4-[6-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol ;

{4-[6-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanol (3-Chloro-benzyl)-[3-(5-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine;
3-[6-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol (3-Chloro-benzyl)-(3-pyridin-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine;
[3-(3-Amino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(3-chloro-benzyl)-amine;

(3-Chloro-benzyl)-[3-(6-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine 4-[6-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol;
(3-Chloro-benzyl)-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-amine;
3-[6-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide 4-[6-(3-Chloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;

(4-Fluoro-benzyl)-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-amine 4-[6-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol;
(4-Fluoro-benzyl)-[3-(5-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine 3-[6-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-yI]-phenol;
(4-Fluoro-benzyl)-[3-(4-methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine (3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-(4-fluoro-benzyl)-amine;
(4-Fluoro-benzyl)-[3-(1H-indol-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine;
(4-Fluoro-benzyl)-[3-(4-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine;
(4-Fluoro-benzyl)-[3-(6-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl)-amine;
N-{3-[6-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-acetamide;

(4-Fluoro-benzyl)-(3-pyridin-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine {4-[6-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}methanol;
3-[6-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide 4-[6-(4-Fluoro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid (4-Methoxy-benzyl)-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-yl)-amine [3-(4-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(4-methoxy-benzyl)-amine (4-Methoxy-benzyl)-[3-(4-methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
[3-(1H-Indol-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-(4-methoxy-benzyl)-amine (4-Methoxy-benzyl)-[3-(4-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine [3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(4-methoxy-benzyl)-amine 4-[6-(4-Methoxy-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
(4-Methoxy-benzyl)-[3-(1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl)-amine ;
(4-Methoxy-benzyl)-[3-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
4-[6-(4-Methoxy-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;
4-{[3-(3,4,5-Trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide ;

4-{[3-(4-Hydroxy-3-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide ;
4-{(3-(3-Hydroxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide ;
4-[(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-methyl]-benzenesulfonamide ;
4-[(3-p-Tolyl-imidazo[1,2-b]pyridazin-6-ylamino)-methyl]-benzenesulfonamide ;
4-{[3-(3,4-Dimethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide ;

4-{[3-(4-Cyano-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl)-benzenesulfonamide 4-{[3-(3-Trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylaminol-methyl)-benzenesulfonamide 1 4-{(3-(1H-Indol-5-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide ;
4-[(3-Benzo[1,31dioxo1-5-yl-imidazo[1,2-b]pyridazin-6-ylamino)-methyl]-benzenesulfonamide;
4-{[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide;

4-{[3-(3-Trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide , 4-{[3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide , 4-{[3-(4-Hydroxy-phenyI)-imidazo[1, 2-b]-pyridazin-6-ylamino]-methyl)-be Nzenesulfonamide, 4-{[3-(3-Hydroxymethyl-phenyl)-imid azo[1,2-b]pyridazin-6-ylamino]-meth yl}-benzenesulfonamide , 4-{[3-(3-Acetyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-methyl}-benzenesulfonamide ;

4-{[3-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1 ,2-b]pyridazin-6-ylamino]-methyl)-benzenesulfonamide (3,4-Dichloro-benzyl)-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine 4-[6-(3,4-Dichloro-benzylamino)-imidazo[1 ,2-b]pyridazin-3-yl)-phenol, (3,4-Dichloro-benzyl)-[3-(4-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine (3,4-Dichloro-benzyl)-[3-(6-methoxy-pyridin-3-0)--imidazo[1,2-b]pyridazin-6-yl]-amine ;

(3,4-Dichloro-benzyl)-[3-(1H-indol-5-yl)-imidazo[1,2-b]pyridazin-6-yl)-amine ;
4-[6-(3,4-Dichloro-benzylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;
Benzo[1,3]dioxol-5-ylmethyl-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
4-{6-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-2-methoxy-phenol ;
Benzo[1,3]dioxol-5-ylmethyl-[3-(4-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Benzo[1,3]dioxol-5-ylmethyl-[3-(6-methoxy-pyridin-3-yl)-imidazo[1,2-b)pyridazin-6-yl)-amine , 4-{6-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl)-phenol 3-{6-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-phenol Benzo[1,3]dioxol-5-ylmethyl-[3-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl)-amine 4-{6-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-benzoic acid N-(3-{6-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl)-phenyI)-methanesulfonamide ;
3-{6-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-imidazo[1,2-b]pyridazin-3-yl}-benzamide;

(2-Methoxy-ethyl)-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
(2-Methoxy-ethyl)-[3-(3-methoxy-phenyl)imidazo[1,2-b]pyridazin-6-yl]-amine ;
2-Methoxy-4-[6-(2-methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
(2-Methoxy-ethyl)-[3-(5-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
(2-Methoxy-ethyl)-(3-naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
(2-Methoxy-ethyl)-[3-(6-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;

(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-methoxy-ethyl)-amine ;
[3-(4-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-methoxy-ethyl)-amine ;
(2-Methoxy-ethyl)-(3-(4-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl)-amine ;
(3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-(2-methoxy-ethyl)-amine ;
(2-Methoxy-ethyl)-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
N-{3-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-acetamide ;

(2-Methoxy-ethyl)-[3-(3-trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
[3-(1H-Indol-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-methoxy-ethyl)-amine ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-methoxy-ethyl)-amine ;
(2-Methoxy-ethyl)-[3-(4-methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
4-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
{4-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanol ;

(2-Methoxy-ethyl)-[3-(3-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl}-amine ;
[3-(3-Bromo-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(2-methoxy-ethyl)-amine ;
4-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;
3-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide ;
N-{3-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanesulfonamide ;
[3-(1-Benzyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-(2-methoxy-ethyl)-amine ;

[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2b]pyridazin-6-yl]-(2-methoxy-ethyl)-amine ;
1-{3-[6-(2-Methoxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl)-phenyl}-ethanone ;
3-[3-(3,4,5-Trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
4-[6-(3-Hydroxy-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol ;
3-[3-(3-Bromo-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
3-[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;

3-[3-(3-Trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol, 3-[3-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
3-[3-(3-Trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
3-[3-(4-Methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
3-(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol ;
3-(3-p-Tolyl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol ;

3-(3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol; ;
3-(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol ;
3-[3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol;
;
3-[3-(1H-Indol-5-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol;
3-[3-(4-Methoxy-phenyI)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
3-[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-ylaminol-propan-1-ol;

3-[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
N-{3-[6-(3-Hydroxy-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanesulfonamide ;
3-[3-(1-Benzyl-1H-pyrazol-4-yl)-imidazo[1,2-b]-pyridazin-6-ylamino]-propan-1-ol ;
3-[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-propan-1-ol ;
3-(3-Naphthalen-1-yl-imidazo[1,2-b]pyridazin-6-ylamino)-propan-1-ol ;
Propyl-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;

2-Methoxy-4-(6-propylamino-imidazo[1,2-b]pyridazin-3-yl)-phenol ;
[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-propyl-amine ;
[3-(1H-Indol-5-yl)-imidazo[1,2-b]pyridazin-6-yl)-propyl-amine [3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl)-propyl-amine ;
N-[3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-phenyl)-acetamide ;
Propyl-[3-(3-trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine [3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl-propyl-amine ;
Propyl-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
[3-(4-Methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-propyl-amine ;
Propyl-(3-pyridin-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
[3-(6-Methoxy-pyridin-3-yl)-imidazo [1,2-b]pyridazin-6-yl]-propyl-amine ;
4-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-phenol ;

(3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-propyl-amine ;
[3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-phenyl]-methanol ;
4-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-benzoic acid ;
3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-benzamide ;
[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-propyl-amine ;
3-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-phenol ;

(3-(3-Amino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-propyl-amine ;
[3-(4-Amino-phenyl-imidazo[1,2-b]pyridazin-6-yl]-propyl-amine ;
[3-(4-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-propyl-amine [4-(6-Propylamino-imidazo[1,2-b]pyridazin-3-yl)-phenyl]-methanol ;
[3-(5-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-propyl-amine;
N,N-Dimethyl-N'-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-yl)-ethane-1,2-diamine ;

N'-(3-Benzofuran-2-yl-imidazo[1,2-b]pyridazin-6-yl)-N,N-dimethyl-ethane-1,2-diamine ;
N,N-Dimethyl-N'-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-ethane-1,2-diamine ;
N,N-Dimethyl-N'-(3-naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-ethane-1,2-diamine ;
N'-(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-N,N-dimethyl-ethane-1,2-diamine ;
N'-[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-N,N-dimethyl-ethane-1,2-diamine ;
N'-[3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-N,N-dimethyl-ethane-1,2-diamine ;

N'-[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-N,N-dimethyl-ethane-1,2-diamine ;
(S)-3-Methyl-2-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
4-[6-((S)-1-Hydroxymethyl-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol ;
(S)-2-[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol ;
3-[6-((S)-1-Hydroxymethyl-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
4-[6-((S)-1-Hydroxymethyl-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;

(S)-2-[3-(4-Hydroxymethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol ;
(S)-2-[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol ;
(S)-3-Methyl-2-(3-naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-butan-1-ol ;
(S)-3-Methyl-2-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
(S)-2-(3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-ylamino)-3-methyl-butan-1-ol ;
(S)-3-Methyl-2-[3-(4-methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;

(S)-3-Methyl-2-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylamino)-butan-1-ol (S)-3-Methyl-2-[3(3-trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol (S)-2-[3(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol (S)-2-[3(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol;
(S)-2-[3(1H-Indol-5-yl )-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol ;
3-[6-((S)-1-Hydroxymethyl-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide 1-{3-[6-((S)-1-Hydroxymethyl-2-methyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-ethanone ;
(S)-2-[3-(5-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-3-methyl-butan-1-ol ;
2-[3-(3,4,5-Trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-butan-1-ol ;
2-[3-(3-Trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;

2-(3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylamino)-butan-1-ol ;
2-[3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-[3-(4-Methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-[3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-[3-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;

2-[3-(3-Bromo-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-[3-(3-Trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
2-[3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;
3-[6-(1-Hydroxymethyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide ;
4-[6-(1-Hydroxymethyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;
2-[3-(1-Benzyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol ;

N-{3-[6-(1-Hydroxymethyl-propylamino)-Imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanesulfonamide ;
1-{3-[6-(1-Hydroxymethyl-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-ethanone 2-[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol 2-[3-(5-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-butan-1-ol , (Tetrahydro-pyran-4-yl)-(3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine , [3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine (Tetrahydro-pyran-4-yl)-[3-(3-trifluoromethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]amine ;
{4-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanol ;
[3-(4-Methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
[3-(3-Chloro-4-fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
[3-(3-Bromo-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
[3-(1-Methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;

[3-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl)-methanol ;
[3-(5-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine i [3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine 7 [3-(4-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
[3-(1H-Indo1-5-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;

(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(tetrahydro-pyran-4-yl)-amine ;
[3-(3,4-Dimethyl-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine,;
(3-Furan-2-yl-imidazo[1,2-b]pyridazin-6-yl)-(tetrahydro-pyran-4-yl)-amine N-(2-Hydroxy-ethyl)-3-[6-(tetrahydra-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide 4-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid methyl ester ;
(Tetrahydro-pyran-4-yl)-(3-p-tolyl-imidazo[1,2-b]pyridazin-6-yl)-amine [3-(4-Amino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine [3-[4-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine N-{3-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-acetamide [3-(3-Amino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine [3-(2-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine (3-Naphthalen-1-yl-imidazo[1,2-b]pyridazin-6-yl)-(tetrahydro-pyran-4-yl)-amine (3-Pyridin-3-yl-imidazo[1,2-b]pyridazin-6-yl)-(tetrahydro-pyran-4-yl)-amine ;
[3-(4-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
(3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-(tetrahydro-pyran-4-yl)-amine ;
3-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
(Tetrahydro-pyran-4-yl)-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
[3-(3,4-Dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;

(Tetrahydro-pyran-4-yl)-[3-(3-trifluoromethoxy-phenyl)-imidazo[1,2-b[pyridazin-6-yl]-amine;
[3-(3-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine;
2-memory-4-[6-(tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol;
(Tetrahydro-pyran-4-yl)-(3-thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-amine;
(3-(1H-Pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine;
3-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide;

[3-(1-Benzyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine;
4-[6-(Tetrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;
N-{3-[6-(Tretrahydro-pyran-4-ylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanesulfonamide ;
[3-(3-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-(tetrahydro-pyran-4-yl)-amine ;
4-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-yI]-2-methoxy-phenol;

4-[3-(3-Trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol ;
4-[3-(3-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;
4-(3-Thiophen-3-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol;
4-(3-Benzo[b]thiophen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol;
4-[3-(3-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;
4-[3-(3-Fluoro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol ;

4-(3-Naphthalen-1-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol;
N-{3-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-acetamide;
4-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol;
4-(3-Naphthalen-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol;
4-(3-Phenyl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol;
4-[3-(1H-Indol-5-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;

4-[3-(4-Dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;
4-[3-(4-Methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;
4-(3-Quinolin-8-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol;
4-(3-Furan-2-yl-imidazo[1,2-b]pyridazin-6-ylamino)-cyclohexanol;
4-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid methyl ester;
4-[3-(4-Trifluoromethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;

4-[3-(3,4-Dimethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;
4-[3-(4-Hydroxymethyl-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;
4-[3-(4-Chloro-phenyl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol;
4-[3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-ylamino]cyclohexanol;
4-[3-(5-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-cyclohexanol ;
3-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol;

4-[6-(4-Hydroxy-cyclohexylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;
Cyclopropylmethyl-[3-(3,4,5-trimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
4-[6-(Cyclopropylmethyl-amino)imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol ;
Cyclopropylmethyl-[3-(3,4-dimethoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine Cyclopropylmethyl-[3-(3-dimethylamino-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Cyclopropylmethyl-(3-pyridin-4-yl-imidazo[1,2-b]pyridazin-6-yl)-amine {3-(6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}methanol ;
Cyclopropylmethyl-[3-(3-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Cyclopropylmethyl-[3-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Cyclopropylmethyl-[3-(1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
(3-Benzo[1,3]dioxol-5-yl-imidazo[1,2-b]pyridazin-6-yl)-cyclopropylmethyl-amine ;
Cyclopropylmethyl-[3-(4-methoxy-phenyl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;

Cyclopropylmethyl-(3-thiophen-3-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
Cyclopropylmethyl-[3-(6-methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
Cyclopropylmethyl-[3-(4-methyl-thiophen-2-yl)-imidazo[1,2-b]pyridazin-6-yl]-amine ;
N-{3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-acetamide ;
3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-N-(2-hydroxy-ethyl)-benzamide ;
(4-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanol ;

4-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
N-{3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-methanesulfonamide ;
3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;
[3-(1-Benzyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-cyclopropylmethyl-amine ;
4-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-benzoic acid ;

3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-benzamide ;
1-{3-[6-(Cyclopropylmethyl-amino)-imidazo[1,2-b]pyridazin-3-yl]-phenyl}-ethanone ;
Cyclopropylmethyl-(3-thiophen-2-yl-imidazo[1,2-b]pyridazin-6-yl)-amine ;
[3-(2-Methoxy-pyridin-4-yl)-imidazo[1,2-b]pyridazin-6-yl]-piperidin-4-yl-amine ;
4-[3-(2-Methoxy-pyridin-4-yl)-imidazo[1,2-b]pyridazin-6-ylamino]-piperidine-1-carboxylic acid tert-butyl ester ;
(3-(6-Methoxy-pyridin-3-yl)-imidazo[1,2-b]pyridazin-6-yl]-piperidin-4-yl-amine ;
3-[6-(2-Hydroxy-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-benzenesulfonamide ;

4-[6-(2-Hydroxy-ethylamino)-imidazo [1,2-b]pyridazin-3-yl)-benzenesulfo Namide ;
4-[6-(3-Dimethylamino-propylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol ;
or 4-[6-(2-Morpholin-4-yl-ethylamino)-imidazo[1,2-b]pyridazin-3-yl]-phenol.

11. An intermediate according to formula IIa wherein Y is a halogen atom, and R1 and R2 are each as defined in claim 1.

12. An intermediate according to formula lIb wherein Q, A and B are each as defined in claim 1, and X is chlorine, bromine, O-SO2-CF3 or O-SO2-C4F9;
with the proviso that the intermediate is not

13. A method for preparing a compound as defined in any one of claims 1 to 10, comprising the following steps:
A1) converting 3-amino-6-halopyrazine into 6-haloimidazo[1,2-b]pyridazine II, A2) converting the product from stage A1 into a 3-halo-6-haloimidazo[1,2-b]pyridazine III, A3) converting the product from stage A2 by reaction with a compound NHR1R2 into a compound according to formula Ila as defined in claim 11, and A4) converting the product from stage A3 into the compound as defined in any one of claims 1 to 10, or B1) converting 3-amino-6-halopyrazine into 6-haloimidazo[1,2-b]pyridazine II, B2) converting the product from stage B1 into a 3-halo-6-haloimidazo[1,2-b]pyridazine III, B3) converting the product from stage B2 into a compound according to formula lIb as defined in claim 12, and B4) converting the product from stage B3 into the compoundas defined in any one of claims 1 to 10, or C1) converting 3-amino-6-halopyrazine into 6-haloimidazo[1,2-b]pyridazine II, C2) converting the product from stage C1 by reaction with a compound NHR1R2 into an imidazo[1,2-b]pyridazin-6-yl)-(R1)-(R2)-amine IV, C3) converting the product from stage C2 into the compound according to formula Ila, and C4) converting the product from stage C3 into the compoundas defined in any one of claims 1 to 10.

14. The method as claimed in claim 11, comprising the following steps:
A1) reacting 3-amino-6-halopyrazine with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, A2) reacting the product from stage A1 with N-bromosuccinimide to give a 3-bromo-6-haloimidazo[1,2-b]pyridazine, A3) converting the product from stage A2 by reaction with a compound NHR1R2 in a Buchwald-Hartwig cross-coupling reaction into a (3-bromoimidazo[1,2-b]pyridazin-6-yl)-(R1)-(R2)-amine, and A4) reacting the product from stage A3 with a boronic acid which is optionally substituted by the radicals A and B to give the compound as defined in any one of claims 1 to 10, or B1) reacting 3-amino-6-halopyrazine with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, B2) reacting the product from stage B1 with N-bromosuccinimide to give a 3-bromo-6-haloimidazo[1,2-b]pyridazine, B3) reacting the product from stage B2 with a boronic acid which is optionally substituted by the radicals A and B to give the compound according to formula IIb, and B4) converting the product from stage B3 by reacting with a compound NHR1R2 in a Buchwald-Hartwig cross-coupling reaction into the compound as defined in any one of claims 1 to 10, or C1) reacting 3-amino-6-halopyrazine with chloractetaldehyde to give 6-haloimidazo[1,2-b]pyridazine, C2) converting the product from stage C1 by reacting with a compound NHR1R2 in a Buchwald-Hartwig cross-coupling reaction into an imidazo[1,2-b]pyridazin-6-yl)-(R1)-(R2)-amine, C3) reacting the product from stage C2 with N-bromosuccinimide to give a (3-bromoimidazo[1,2-b]pyridazin-6-yl)-(R1)-(R2)-amine, and C4) reacting the product from stage C3 with a boronic acid which is optionally substituted by the radicals A and B to give the compound as defined in any one of claims 1 to 10.

15. Use of a compound as defined in any one of claims 1 to 10 in the manufacture of a medicament for treating a disorder associated with over-expression of a cellular kinase.

16. Use of a compound as defined in any one of claims 1 to 10 in the manufacture of a medicament for inhibiting a cellular kinase.

17. The use as claimed in claim 15 to 16, wherein the kinase belongs to the group of the protein kinase C family.

18. The use as claimed in claim 17, wherein the kinase is PKC theta, delta, iota, alpha or zeta.

19. The useas claimed in claim 15 or 16, wherein the kinase is from the class of the ALK
family.

20. The use as claimed in claim 19, wherein the kinase is ALK1, ALK2, ALK4 or ALK5.

21. The use as claimed in claim 15, wherein the disorder is a benign tumor, a malignant tumor leukemia, lymphoma, sarcoma, neuroblastoma, a Wilm's tumor, a malignant neoplasm of the bladder, breast, lung, pancreas, prostate, or kidney, or a neoplasm of epithelial origin.

22. The use as claimed in claim 15, wherein the disorder is an epidermal hyperproliferation, Alzheimer's disease, an autoinflammatory disorder, fibroses, impaired wound healing, diabetic retinopathy, nephropathy, age-related macular degeneration, Crohn's disease, exaggerated immune response, contact dermatitis, atopic dermatitis, multiple sclerosis, ALS, diabetes, or asthma.

23. A pharmaceutical composition comprising a compound as defined in any one of claims 1 to 10, and a pharmaceutically acceptable carrier, for treating a disorder associated with over-expression of a cellular kinase.

24. The pharmaceutical composition as claimed in claim 23, wherein the disorder is a benign tumor, a malignant tumor leukemia, lymphoma, sarcoma, neuroblastoma, a Wilm's tumor, a malignant neoplasm of the bladder, breast, lung, pancreas, prostate, or kidney, or a neoplasm of epithelial origin.

25. The pharmaceutical composition as claimed in claim 23, wherein the disorder is an epidermal hyperproliferation, Alzheimer's disease, an autoinflammatory disorder, fibroses, impaired wound healing, diabetic retinopathy, nephropathy, age-related macular degeneration, Crohn's disease, exaggerated immune response, contact dermatitis, atopic dermatitis, multiple sclerosis, ALS, diabetes, or asthma.