HRP20212021T1 - 4-IMIDAZOPIRIDAZIN-1-iL-BENZAMIDI I 4-IMIDAZOTRIAZIN-1-IL-BENZAMIDI KAO INHIBITORI BTK - Google Patents
4-IMIDAZOPIRIDAZIN-1-iL-BENZAMIDI I 4-IMIDAZOTRIAZIN-1-IL-BENZAMIDI KAO INHIBITORI BTK Download PDFInfo
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- HRP20212021T1 HRP20212021T1 HRP20212021TT HRP20212021T HRP20212021T1 HR P20212021 T1 HRP20212021 T1 HR P20212021T1 HR P20212021T T HRP20212021T T HR P20212021TT HR P20212021 T HRP20212021 T HR P20212021T HR P20212021 T1 HRP20212021 T1 HR P20212021T1
- Authority
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- Croatia
- Prior art keywords
- alkyl
- compound
- use according
- optionally substituted
- cycloalkyl
- Prior art date
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- 229940124291 BTK inhibitor Drugs 0.000 title 1
- NBOUQRHNEKKMCI-UHFFFAOYSA-N N1(N=CC=C2C1=NC=N2)C1=CC=C(C(=O)N)C=C1 Chemical class N1(N=CC=C2C1=NC=N2)C1=CC=C(C(=O)N)C=C1 NBOUQRHNEKKMCI-UHFFFAOYSA-N 0.000 title 1
- RFMXXXSWDWZODI-UHFFFAOYSA-N N1(N=NC=C2C1=NC=N2)C1=CC=C(C(=O)N)C=C1 Chemical class N1(N=NC=C2C1=NC=N2)C1=CC=C(C(=O)N)C=C1 RFMXXXSWDWZODI-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 4
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 4
- LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 claims 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 2
- 229940022663 acetate Drugs 0.000 claims 2
- 229940072107 ascorbate Drugs 0.000 claims 2
- 235000010323 ascorbic acid Nutrition 0.000 claims 2
- 239000011668 ascorbic acid Substances 0.000 claims 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims 2
- 229940077388 benzenesulfonate Drugs 0.000 claims 2
- 229940050390 benzoate Drugs 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims 2
- 229960001860 salicylate Drugs 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 2
- 229940095064 tartrate Drugs 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 102200080066 rs122460151 Human genes 0.000 claims 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
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- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Claims (13)
1. Spoj prema formuli I
[image]
ili njegova farmaceutski prihvatljiva sol, pri čemu
X je CH, N, O ili S;
Y je C (R6), N, O ili S;
Z je CH, N ili veza;
A je CH ili N;
B1 je N ili C (R7);
B2 je N ili C (R8);
B3 je N ili C (R9);
B4 je N ili C (R10);
R1 je R1 1C(O), R12S(O), R13SO2 ili (1-6C) alkil izborno supstituiran sa R14;
R2 je H, (1-3C) alkil ili (3-7C) cikloalkil;
R3 je H, (1-6C) alkil ili (3-7C) cikloalkil); ili
R2 i R3 formiraju, zajedno sa atomom N i C za koji su vezani, (3-7C) heterocikloalkil izborno supstituiran sa jednim ili više fluora, hidroksila, (1-3C) alkila, (1-3C) alkoksi ili okso;
R4 je H ili (1-3C) alkil;
R5 je H, halogen, cijano, (1-4C) alkil, (1-3C) alkoksi, (3-6C) cikloalkil, čija je svaka alkil grupa izborno supstituirana sa jednim ili više halogena; ili R5 je (6-10C)aril ili (2-6C)heterocikloalkil;
R6 je H ili (1-3C) alkil; ili
R5 i R6 zajedno mogu formirati (3-7C) cikloalkenil ili (2-6C) heterocikloalkenil; svaki izborno supstituiran sa (1-3C) alkilom, ili jednim ili više halogena;
R7 je H, halogen ili (1-3C) alkoksi;
R8 je H ili (1-3C) alkil; ili
R7 i R8 formiraju, zajedno sa atomom ugljika za koji su vezani za (6-10C)aril ili (1-9C)heteroaril;
R9 je H, halogen ili (1-3C) alkoksi
R10 je H, halogen ili (1-3C) alkoksi
R11 je neovisno izabran iz grupe koja se sastoji od: (1-6C) alkila, (2-6C) alkenila i (2-6C) alkinila, svaki alkil, alkenil ili alkinil izborno supstituiran sa jednom ili više grupa izabranih između hidroksila, (1-4C)alkila, (3-7C) cikloalkila, [(1-4C) alkil] amino, di [(1-4C) alkil] amino, (1-3C) alkoksi, (3-7C) cikloalkoksi, (6-10C) arila ili (3-7C) heterocikloalkila; ili
R11 je (1-3C) alkil-C(O)-S-(1-3C) alkil; ili
R11 je (1-5C) heteroaril izborno supstituiran sa jednom ili više grupa izabranih od halogena ili cijano;
R12 i R13 su neovisno izabrani iz grupe koja se sastoji od (2-6C) alkenila ili (2-6C) alkinila, oba izborno supstituirana sa jednom ili više grupa izabranih između hidroksila, (1-4C) alkila, (3-7C) cikloalkila, [(1-4C) alkil] amino, di [(1-4C) alkil] amino, (1-3C) alkoksi, (3-7C) cikloalkoksi, (6-10C) aril ili (3-7C) heterocikloalkil; ili
(1-5C) heteroaril izborno supstituiran sa jednom ili više grupa izabranih od halogena ili cijano;
R14 je neovisno izabran iz grupe koja se sastoji od: halogena, cijano ili (2-6C) alkenila ili (2-6C) alkinila, oba izborno supstituirana sa jednom ili više grupa izabranih između hidroksila, (1-4C) alkila, (3-7C) cikloalkila, [(1-4C) alkil] amino, di [(1-4C) alkil] amino, (1-3C) alkoksi, (3-7C) cikloalkoksi, (6-10C) arila, (1-5C) heteroarila ili (3-7C) heterocikloalkila;
uz uvjet da
- 0 do 2 atoma X, Y, Z mogu istovremeno biti heteroatom;
- kada je jedan atom izabran od X, Y je O ili S, tada je Z veza, a drugi atom izabran od X, Y ne može biti O ili S;
- kada je Z jednako C ili N tada je Y jednako C (R6) ili N i X je C ili N;
- 0 do 2 atoma B1, B2, B3 i B4 su N.
2. Spoj prema zahtjevu 1, za uporabu u postupku liječenja difuznog krupno staničnog limfoma B-stanica (DLBCL) kod subjekta.
3. Spoj za uporabu prema zahtjevu 2, naznačen time što spoj je spoj formule:
[image]
ili njegova farmaceutski prihvatljiva sol.
4. Spoj za uporabu prema zahtjevu 3, naznačen time što spoj je spoj formule:
[image]
5. Spoj za uporabu prema zahtjevu 3, naznačen time što je spoj farmaceutski prihvatljiva sol spoja formule:
[image]
6. Spoj za uporabu prema bilo kojem od zahtjeva 2, 3 ili 5, naznačen time što je farmaceutski prihvatljiva sol izabrana iz grupe koja se sastoji od acetata, askorbata, benzoata, benzensulfonata, bisulfata, borata, butirata, citrata, kamforata, kamforsulfonata, fumarata, hidroklorida, hidrobromida, hidrojodida, laktata, maleata, metansulfonata, naftalensulfonata, nitrata, oksalata, fosfata, propionata, salicilata, sukcinata, sulfata, tartarata, tiocijanata i toluensulfonata.
7. Farmaceutska kompozicija koja sadrži spoj i farmaceutski prihvatljivo pomoćno sredstvo za uporabu u postupku liječenja difuznog krupno staničnog limfoma B-stanica (DLBCL) kod subjekta, pri čemu spoj je spoj formule:
[image]
ili njegova farmaceutski prihvatljiva sol.
8. Farmaceutska kompozicija za uporabu prema zahtjevu 7, naznačena time što spoj je spoj formule:
[image]
9. Farmaceutska kompozicija za uporabu prema zahtjevu 7, naznačena time što je spoj farmaceutski prihvatljiva sol spoja formule:
[image]
10. Farmaceutska kompozicija za uporabu prema zahtjevu 7 ili 9, naznačena time što je farmaceutski prihvatljiva sol izabrana iz grupe koja se sastoji od acetata, askorbata, benzoata, benzensulfonata, bisulfata, borata, butirata, citrata, kamforata, kamforsulfonata, fumarata, hidroklorida, hidrobromida, hidrojodida, laktata, maleata, metansulfonata, naftalensulfonata, nitrata, oksalata, fosfata, propionata, salicilata, sukcinata, sulfata, tartarata, tiocijanata i toluensulfonata.
11. Spoj za uporabu prema bilo kojem od zahtjeva 2 do 6, naznačen time što se spoj primjenjuje na subjekta oralno.
12. Farmaceutska kompozicija za uporabu prema bilo kojem od zahtjeva 7 do 10, naznačena time što se farmaceutska kompozicija primjenjuje na subjekta oralno.
13. Spoj ili farmaceutska kompozicija za uporabu prema bilo kojem od zahtjeva 2 do 12, naznačena time što je subjekt humani subjekt.
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