HRP20192279T1 - Novi spojevi imidazopiridazina i njihova uporaba - Google Patents
Novi spojevi imidazopiridazina i njihova uporaba Download PDFInfo
- Publication number
- HRP20192279T1 HRP20192279T1 HRP20192279TT HRP20192279T HRP20192279T1 HR P20192279 T1 HRP20192279 T1 HR P20192279T1 HR P20192279T T HRP20192279T T HR P20192279TT HR P20192279 T HRP20192279 T HR P20192279T HR P20192279 T1 HRP20192279 T1 HR P20192279T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- heteroaryl
- optionally substituted
- phenyl
- group
- Prior art date
Links
- 150000005233 imidazopyridazines Chemical class 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000005842 heteroatom Chemical group 0.000 claims 13
- 125000004076 pyridyl group Chemical group 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims 11
- -1 pyrrolopyrimidinyl Chemical group 0.000 claims 11
- 125000006413 ring segment Chemical group 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 125000001246 bromo group Chemical group Br* 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 2
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 2
- 108091007960 PI3Ks Proteins 0.000 claims 2
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims 1
- 208000003950 B-cell lymphoma Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 208000002250 Hematologic Neoplasms Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010042971 T-cell lymphoma Diseases 0.000 claims 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229910052805 deuterium Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 201000003444 follicular lymphoma Diseases 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 208000003747 lymphoid leukemia Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 150000003217 pyrazoles Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- 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
Claims (15)
1. Spoj s formulom (I):
i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri, naznačen time što
Ar je aril, navedeni aril je karbociklički ugljikovodični radikal monocikličkog prstena ili kondenziranih prstenova koji sadrže 6-12 ugljikovih atoma u prstenu, pri čemu je najmanje jedan prsten aromatski i niti jedan od ostalih prstenova je heteroaril;
ili heteroaril, navedeni heteroaril je monociklički aromatski radikal ugljikovodika koji ima 5, 6 ili 7 atoma u prstenu, te sadrži 1 ili 2 heteroatoma u prstenu koji su neovisno odabrani od N, O, i S, pri čemu su preostali atomi u prstenu ugljik; ili biciklički aromatski radikal ugljikovodika koji ima 9 ili 10 atoma u prstenu, i sadrži u prstenovima 1, 2, 3 ili 4 heteroatoma koji su neovisno odabrani od N, O, i S, pri čemu su preostali atomi u prstenu ugljik, pri čemu je barem jedan od prstenova aromatski, kada ukupni broj S i O atoma u heteroarilnoj skupini prelazi 1, ti heteroatomi nisu susjedni jedan drugom, i navedena heteroarilna skupina ih također uključuje pri čemu se N heteroatom javlja kao N-oksid;
svaki navedeni aril i heteroaril je proizvoljno supstituiran s jednom ili više skupina odabranih od deuterija, halo, -CN, -OH, -SH, C1-6 alkil, C1-6 haloalkil, -(C1-6alkil)OH, i -S(O)2(C1-6 alkil);
W je odabran od heteroarila i -N(R3)heteroarila, pri čemu je navedeni heteroaril monociklički aromatski radikal ugljikovodika koji sadrži dušik koji ima 5, 6 ili 7 atoma u prstenu, i sadrži 1 ili 2 heteroatoma, pri čemu heteroatom(i) je/su dušikovi atomi, pri čemu su preostali atomi u prstenu ugljik; ili biciklički aromatski radikal ugljikovodika koji sadrži dušik koji ima 9 ili 10 atoma u prstenu, i sadrži 1, 2, 3 ili 4 heteroatoma, pri čemu heteroatom(i) je/su dušikovi atomi, pri čemu su preostali atomi u prstenu ugljik, pri čemu je barem jedan od prstena aromatski; i navedena heteroarilna skupina ih također uključuje pri čemu se N heteroatom javlja kao N-oksid, i navedeni heteroaril je proizvoljno supstituiran s jednom ili više skupina odabranih od halo, -CN, -OH, -SH, C1-6 alkil, -NH2, -NH(C1-6 alkil), -N(C1-6 alkil)(C1-6 alkil), -COOH, -C(O)NH2, -C(O)NH(C1-6 alkil), - C(O)N(C1-6 alkil)(C1-6 alkil), fenil, i 5- ili 6-eročlanog heteroarila; u kojem navedeni 5- ili 6-eročlani heteroaril je monociklički aromatski radikal ugljikovodika koji ima 5 ili 6 atoma u prstenu, te sadrži u prstenu 1, 2 ili 3 heteroatoma koji su neovisno odabrani od N, O, i S, pri čemu su preostali atomi u prstenu ugljik, kada ukupni broj S i O atoma u heteroarilnoj skupini prelazi 1, ti heteroatomi nisu susjedni jedan drugom, i svaki navedeni fenil ili navedeni 5- ili 6-eročlani heteroaril kao supstituent od W je proizvoljno supstituiran s jednom ili više skupina odabranih iz niza koji sadrži halo, -OH, -SH, C1-6 alkil, i -O(C1-6alkil);
R1 je neovisno odabran od H, halo, i C1-6 alkila;
R2 je odabran od C1-6 alkila;
R3 je H ili C1-6 alkil;
m je 1 ili 2.
2. Spoj s formulom (I) prema patentnom zahtjevu 1, i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri, naznačen time što W je odabran od heteroaril koji sadrži dušik ili -N(R3) heteroaril koji sadrži dušik, pri čemu je navedeni heteroaril koji sadrži dušik odabran iz skupine koja sadrži pirimidinil, pirolopirimidinil i purinil, te je proizvoljno supstituiran s jednom ili više skupina odabranih od fluoro, kloro, bromo, -CN, -OH, -SH, C1-6 alkil, -NH2, -NH(C1-6 alkil), -N(C1-6 alkil)(C1-6 alkil), - COOH, -C(O)NH2, fenil, i 5- ili 6-eročlanog heteroarila odabranog iz skupine koja sadrži piridil, pirazolil i tetrazolil; u kojem svaki navedeni fenil ili navedeni 5- ili 6-eročlani heteroaril kao supstituent od W je proizvoljno supstituiran s jednom ili više skupina odabranih iz niza koji sadrži halo, -OH, C1-6 alkil, i -O(C1-6 alkil).
3. Spoj s formulom (I) prema patentnom zahtjevu 1 ili zahtjevu 2, i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri, naznačen time što je W odabran od
svaki od kojih je proizvoljno supstituiran s jednom ili više skupina odabranih od fluoro, kloro, bromo, -CN, -OH, -SH, C1-6 alkil, -NH2, -NH(C1-6 alkil), -N(C1-6 alkil)(C1-6 alkil), -COOH, -C(O)NH2, -C(O)NH(C1-6 alkil), fenil, i 5- ili 6-eročlanog heteroarila odabranog iz skupine koja sadrži piridil, pirazolil i tetrazolil; u kojem svaki navedeni fenil i navedeni 5- ili 6-eročlani heteroaril kao supstituent od W je proizvoljno supstituiran s jednom ili više skupina odabranih iz niza koji sadrži halo, -OH, C1-6 alkil, i -O(C1-C6 alkil),
ili
W je odabran od
svaki od kojih je proizvoljno supstituiran s jednom ili više skupina odabranih od kloro, -CN, -NH2, -NH(C1-6 alkil), - COOH, -C(O)NH2, fenil, piridil, oksadiazolil, pirazolil, i tetrazolil; u kojem je svaki navedeni fenil, piridil, oksadiazolil, pirazolil, i tetrazolil proizvoljno supstituiran s jednom ili više skupina odabranih iz niza koji sadrži halo, -OH, C1-6 alkil, i -O(C1-6alkil);
ili
W je
koji je proizvoljno supstituiran s jednom ili više skupina odabranih od fluoro, kloro, bromo, -CN, -OH, -SH, C1-6 alkil, -NH2, -NH(C1-6 alkil), -N(C1-6 alkil)(C1-6 alkil), -COOH, - C(O)NH2, fenil, i 5- ili 6-eročlanog heteroarila odabranog iz skupine koja sadrži piridil, pirazolil i tetrazolil; u kojem svaki navedeni fenil i navedeni 5- ili 6-eročlani heteroaril kao supstituent od W je proizvoljno supstituiran s jednom ili više skupina odabranih od halo, -OH, C1-6 alkil, i -O(C1-6 alkil),
ili
W je
koji je proizvoljno supstituiran s jednom ili više skupina odabranih od kloro, - CN, -NH2, NH(C1-6 alkil), -COOH, -C(O)NH2, fenil, piridil, oksadiazolil, pirazolil i tetrazolil; u kojem svaki navedeni fenil, piridil, oksadiazolil, pirazolil, i tetrazolil je proizvoljno supstituiran s jednom ili više skupina odabranih iz niza koji sadrži halo, -OH, C1-6 alkil, ili -O(C1-6 alkil).
4. Spoj s formulom (I) prema bilo kojem od patentnih zahtjeva 1-3, i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri, naznačen time što Ar je odabranih iz niza koji sadrži fenil, naftil, piridil, pirazolil, kinolil, tienil, benzotiazolil, indolil, i 2,3-dihidro-1,4-benzodioksinil, svaki od kojih je proizvoljno supstituiran s jednom ili više skupina odabranih iz niza koji sadrži D, halo, -CN, C1-6 alkil, -(C1-6 alkil)OH, C1-6 haloalkil, i - S(O)2(C1-6 alkil), na primjer,
Ar je fenil ili piridil, svaki od kojih je proizvoljno supstituiran s jednom ili više skupina odabranih od halo (npr. fluoro), -CN, i C1-6 haloalkil.
5. Spoj s formulom (I) prema bilo kojem od patentnih zahtjeva 1-4, i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri,
naznačen time što R2 je C1-4 alkil, poželjno metil i etil; i/ili
pri čemu R3 je H; i/ili
pri čemu m je 1.
6. Spoj s formulom (I) prema bilo kojem od patentnih zahtjeva 1-5, i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri, naznačen time što formula (I) je formula (I-1),
pri čemu R1, R2, Ar i W su kao što je definirano u bilo kojem od zahtjeva 1-5.
7. Spoj s formulom (I) prema patentnom zahtjevu 6, i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri, naznačen time što W je odabran od heteroaril koji sadrži dušik i -N(R3) heteroaril koji sadrži dušik, pri čemu navedeni heteroaril koji sadrži dušik je monociklički aromatski radikal ugljikovodika koji ima 6 atoma u prstenu, i koji sadrži 1 ili 2 N heteroatoma u prstenu, pri čemu preostali atomi u prstenu su ugljik, ili biciklički aromatski radikal ugljikovodika koji ima 9 atoma u prstenu, i koji sadrži 3 ili 4 N heteroatoma u prstenu, a preostali atomi u prstenu su ugljik, pri čemu je barem jedan od prstenova aromatski, i navedeni heteroaril koji sadrži dušik je proizvoljno supstituiran s jednom ili više skupina odabranih od fluoro, kloro, bromo, -CN, -OH, -SH, C1-6 alkil, -NH2, -NH(C1-6 alkil), -N(C1-6 alkil)(C1-6 alkil), fenil, i 5- ili 6-eročlanog heteroarila odabranog iz skupine koja sadrži piridil, pirazolil i tetrazolil,
ili
W je odabran od
svaki od kojih je proizvoljno supstituiran s jednom ili više skupina odabranih od fluoro, kloro, bromo, -CN, -OH, -SH, C1-6 alkil, -NH2, -NH(C1-6 alkil), -N(C1-6 alkil)(C1-6 alkil), fenil, i 5- ili 6-eročlanog heteroarila odabranog iz skupine koja sadrži piridil, pirazolil i tetrazolil,
ili
W je odabran od
svaki od kojih je proizvoljno supstituiran s jednom ili više skupina odabranih od -CN, -NH2, i tetrazolil; ili
W je
koji je proizvoljno supstituiran s jednom ili više skupina odabranih od fluoro, kloro, bromo, -CN, -OH, -SH, C1-6 alkil, -NH2, -NH(C1-6 alkil), -N(C1-6 alkil)(C1-6 alkil), fenil, i 5- ili 6-eročlanog heteroarila odabranog iz skupine koja sadrži piridil, pirazolil i tetrazolil,
ili
W je
koji je proizvoljno supstituiran s jednom ili više skupina odabranih od -CN, -NH2, i tetrazolil.
8. Spoj s formulom (I) prema patentnom zahtjevu 6 ili zahtjevu 7, i/ili njegova farmaceutski prihvatljiva sol, i/ili njegovi solvati, racemična smjesa, enantiomeri, dijasteromeri, tautomeri, naznačen time što je Ar odabran iz niza koji sadrži fenil, naftil, piridil, pirazolil, kinolil, tienil, i benzotiazolil, svaki od kojih je proizvoljno supstituiran s jednom ili više skupina odabranih od halo, - CN, C1-6 alkil, -(C1-6alkil)OH, i C1-6 haloalkil.
9. Spoj s formulom (I) prema patentnom zahtjevu 1, naznačen time što je odabran od:
i farmaceutski prihvatljiva sol bilo kojeg od njih, i/ili solvati, racemična smjesa, enantiomeri, dijasteromeri, i tautomeri bilo kojeg od njih.
10. Farmaceutski pripravak, naznačen time što sadrži spoj s formulom (I) prema bilo kojem od patentnih zahtjeva 1-9, i/ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljivu pomoćnu tvar.
11. Spoj prema bilo kojem od patentnih zahtjeva 1-9 ili farmaceutski pripravak prema patentnom zahtjevu 10 naznačen time što je za uporabu kao lijek.
12. Spoj prema bilo kojem od patentnih zahtjeva 1-9 ili farmaceutski pripravak prema patentnom zahtjevu 10 naznačen time što je za uporabu u postupku liječenja bolesti koja reagira na inhibiciju PI3K kod subjekta, pri čemu navedena bolest koja reagira na inhibiciju PI3K je upalna bolest, autoimuna bolest ili rak.
13. Spoj ili farmaceutski pripravak za uporabu prema patentnom zahtjevu 12, naznačen time što je navedena upalna bolest ili autoimuna bolest odabrana od reumatoidnog artritisa, kronične opstruktivne plućne bolesti (KOPB), alergijskog rinitisa, astme, lupusa, sistemskog eritematoznog lupusa, psorijaze, i multiple skleroze; navedeni rak je solidni tumor ili hematološka malignost odabrana od leukemije kao što je limfocitna leukemija (ALL), akutna mijeloidna leukemija (AML), kronična limfocitna leukemija (CLL) ili kronična mijelogena leukemija (CML); multiplog mijeloma (MM); i limfoma kao što su Hodgkinov limfom, ne-Hodgkinov limfom (NHL), limfom plaštenih stanica (MCL), folikularni limfom, B-stanični limfom, T-stanični limfom ili difuzni veliki B-stanični limfom (DLBCL).
14. Spoj s formulom (II)
i/ili njegova sol; i/ili racemična smjesa ili njezin enantiomer; naznačen time što su Ar i R2 definirani kao u bilo kojem od zahtjeva 1-9.
15. Spoj s formulom (II) prema patentnom zahtjevu 14, naznačen time što je odabran od:
i
i soli bilo kojeg od njih.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410494483.5A CN105503877A (zh) | 2014-09-24 | 2014-09-24 | 咪唑并哒嗪类化合物及其用途 |
| PCT/CN2015/090367 WO2016045591A1 (en) | 2014-09-24 | 2015-09-23 | Novel imidazopyridazine compounds and their use |
| EP15843649.3A EP3197898B1 (en) | 2014-09-24 | 2015-09-23 | Novel imidazopyridazine compounds and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20192279T1 true HRP20192279T1 (hr) | 2020-03-06 |
Family
ID=55580324
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20192279TT HRP20192279T1 (hr) | 2014-09-24 | 2019-12-18 | Novi spojevi imidazopiridazina i njihova uporaba |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US10208066B2 (hr) |
| EP (1) | EP3197898B1 (hr) |
| JP (1) | JP6381792B2 (hr) |
| KR (2) | KR102111570B1 (hr) |
| CN (2) | CN105503877A (hr) |
| AR (1) | AR101964A1 (hr) |
| AU (1) | AU2015320142B2 (hr) |
| BR (1) | BR112017006002B1 (hr) |
| CA (1) | CA2958671C (hr) |
| CL (1) | CL2017000682A1 (hr) |
| CY (1) | CY1122763T1 (hr) |
| DK (1) | DK3197898T3 (hr) |
| EA (1) | EA032643B1 (hr) |
| ES (1) | ES2765510T3 (hr) |
| HR (1) | HRP20192279T1 (hr) |
| HU (1) | HUE047377T2 (hr) |
| IL (1) | IL250703B (hr) |
| LT (1) | LT3197898T (hr) |
| MX (1) | MX2017003902A (hr) |
| MY (1) | MY178136A (hr) |
| NZ (1) | NZ729886A (hr) |
| PE (1) | PE20170936A1 (hr) |
| PH (1) | PH12017500564B1 (hr) |
| PL (1) | PL3197898T3 (hr) |
| PT (1) | PT3197898T (hr) |
| RS (1) | RS59831B1 (hr) |
| SG (1) | SG11201701545YA (hr) |
| SI (1) | SI3197898T1 (hr) |
| TW (1) | TWI707855B (hr) |
| UA (1) | UA118066C2 (hr) |
| WO (1) | WO2016045591A1 (hr) |
| ZA (1) | ZA201701312B (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105503877A (zh) * | 2014-09-24 | 2016-04-20 | 和记黄埔医药（上海）有限公司 | 咪唑并哒嗪类化合物及其用途 |
| CN109516973A (zh) * | 2017-09-19 | 2019-03-26 | 南京圣和药业股份有限公司 | 取代嘧啶类化合物、其制备方法及用途 |
| CN110386937A (zh) * | 2018-04-20 | 2019-10-29 | 和记黄埔医药（上海）有限公司 | 化合物的晶型和无定型 |
| AR117461A1 (es) | 2018-12-20 | 2021-08-04 | Bayer Ag | Compuestos de heterociclil piridazina como fungicidas |
| CN110028502B (zh) * | 2019-05-29 | 2020-02-14 | 济南周行医药科技有限公司 | 一种激酶抑制剂类药物中间体的制备方法 |
| US20240016152A1 (en) | 2020-06-18 | 2024-01-18 | Bayer Aktiengesellschaft | Active compound combinations |
| CN114031558A (zh) * | 2021-12-14 | 2022-02-11 | 无锡捷化医药科技有限公司 | 一种1-(6-氯哒嗪-4-基）乙基-1-酮的制备方法 |
| WO2023143496A1 (zh) * | 2022-01-28 | 2023-08-03 | 和记黄埔医药（上海）有限公司 | 咪唑并[1,2-b]哒嗪类化合物的中间体的合成方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5773958A (en) | 1997-01-03 | 1998-06-30 | Ovonic Battery Company, Inc. | Apparatus for detecting cell reversal in rechargeable batteries |
| KR100389192B1 (ko) | 1997-04-25 | 2003-06-27 | 다케다 야쿠힌 고교 가부시키가이샤 | 축합 피리다진 유도체, 그것의 제조 방법 및 용도 |
| ES2605792T3 (es) | 2004-05-13 | 2017-03-16 | Icos Corporation | Quinazolinona usada como inhibidor de la fosfatidilinositol 3-quinasa delta humana |
| US8097617B2 (en) | 2006-03-31 | 2012-01-17 | Novartis Ag | Organic compounds |
| MX2009004623A (es) | 2006-10-30 | 2009-05-15 | Novartis Ag | Imidazopiridazinas como inhibidores de la lipido cinasa pi3k. |
| EP2089393A1 (en) | 2006-10-30 | 2009-08-19 | Novartis AG | Heterocyclic compounds as antiinflammatory agents |
| CN101528748A (zh) * | 2006-10-30 | 2009-09-09 | 诺瓦提斯公司 | 作为pi3k脂质激酶抑制剂的咪唑并哒嗪类化合物 |
| AU2008250328A1 (en) | 2007-05-09 | 2008-11-20 | Novartis Ag | Substituted imidazopyridazines as PI3K lipid kinase inhibitors |
| EP2217601A1 (en) * | 2007-11-08 | 2010-08-18 | Centro Nacional de Investigaciones Oncológicas (CNIO) | Imidazopyridazines for use as protein kinase inhibitors |
| WO2009085230A1 (en) | 2007-12-19 | 2009-07-09 | Amgen Inc. | Inhibitors of pi3 kinase |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| WO2010007099A1 (en) * | 2008-07-15 | 2010-01-21 | Cellzome Limited | 2-aminoimidazo[1,2-b]pyridazine derivatives as pi3k inhibitors |
| NZ592880A (en) | 2008-11-13 | 2013-06-28 | Gilead Calistoga Llc | Combinations of purine derivatives and proteasome inhibitors such as bortezomib for the treatment of hematological malignancy |
| WO2012116237A2 (en) * | 2011-02-23 | 2012-08-30 | Intellikine, Llc | Heterocyclic compounds and uses thereof |
| US20140235643A1 (en) * | 2011-10-04 | 2014-08-21 | Gilead Calistoga Llc | Novel quinoxaline inhibitors of pi3k |
| US20130143902A1 (en) | 2011-12-02 | 2013-06-06 | Gilead Calistoga Llc | Compositions and methods of treating a proliferative disease with a quinazolinone derivative |
| WO2013090725A1 (en) | 2011-12-15 | 2013-06-20 | Philadelphia Health & Education Corporation | NOVEL PI3K p110 INHIBITORS AND METHODS OF USE THEREOF |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| US20140120083A1 (en) | 2012-11-01 | 2014-05-01 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
| US20140120060A1 (en) | 2012-11-01 | 2014-05-01 | Infinity Pharmaceuticals, Inc. | Treatment of rheumatoid arthritis and asthma using pi3 kinase inhibitors |
| TWI574962B (zh) | 2012-11-14 | 2017-03-21 | 加拓科學公司 | 作爲ｐｉ３激酶調節劑的芳雜環化合物及其使用方法和用途 |
| ES2685568T3 (es) | 2012-12-21 | 2018-10-10 | Gilead Calistoga Llc | Inhibidores de la isoquinolinona o quinazolinona fosfatidilinositol 3-quinasa |
| CN105503877A (zh) * | 2014-09-24 | 2016-04-20 | 和记黄埔医药（上海）有限公司 | 咪唑并哒嗪类化合物及其用途 |
-
2014
- 2014-09-24 CN CN201410494483.5A patent/CN105503877A/zh active Pending
-
2015
- 2015-09-18 AR ARP150103008A patent/AR101964A1/es active IP Right Grant
- 2015-09-23 UA UAA201703837A patent/UA118066C2/uk unknown
- 2015-09-23 EP EP15843649.3A patent/EP3197898B1/en active Active
- 2015-09-23 NZ NZ729886A patent/NZ729886A/en unknown
- 2015-09-23 ES ES15843649T patent/ES2765510T3/es active Active
- 2015-09-23 KR KR1020197021644A patent/KR102111570B1/ko active IP Right Grant
- 2015-09-23 DK DK15843649.3T patent/DK3197898T3/da active
- 2015-09-23 MX MX2017003902A patent/MX2017003902A/es active IP Right Grant
- 2015-09-23 WO PCT/CN2015/090367 patent/WO2016045591A1/en active Application Filing
- 2015-09-23 PE PE2017000461A patent/PE20170936A1/es unknown
- 2015-09-23 US US15/513,811 patent/US10208066B2/en active Active
- 2015-09-23 KR KR1020177010274A patent/KR102006670B1/ko active IP Right Grant
- 2015-09-23 CA CA2958671A patent/CA2958671C/en active Active
- 2015-09-23 CN CN201580047532.3A patent/CN106715432B/zh active Active
- 2015-09-23 PL PL15843649T patent/PL3197898T3/pl unknown
- 2015-09-23 RS RS20200012A patent/RS59831B1/sr unknown
- 2015-09-23 MY MYPI2017700637A patent/MY178136A/en unknown
- 2015-09-23 SI SI201531035T patent/SI3197898T1/sl unknown
- 2015-09-23 EA EA201790276A patent/EA032643B1/ru unknown
- 2015-09-23 PT PT158436493T patent/PT3197898T/pt unknown
- 2015-09-23 LT LTEP15843649.3T patent/LT3197898T/lt unknown
- 2015-09-23 HU HUE15843649A patent/HUE047377T2/hu unknown
- 2015-09-23 SG SG11201701545YA patent/SG11201701545YA/en unknown
- 2015-09-23 AU AU2015320142A patent/AU2015320142B2/en active Active
- 2015-09-23 BR BR112017006002-7A patent/BR112017006002B1/pt active IP Right Grant
- 2015-09-23 JP JP2017516139A patent/JP6381792B2/ja active Active
- 2015-09-24 TW TW104131565A patent/TWI707855B/zh active
-
2017
- 2017-02-21 ZA ZA2017/01312A patent/ZA201701312B/en unknown
- 2017-02-21 IL IL250703A patent/IL250703B/en active IP Right Grant
- 2017-03-22 CL CL2017000682A patent/CL2017000682A1/es unknown
- 2017-03-24 PH PH12017500564A patent/PH12017500564B1/en unknown
-
2018
- 2018-12-20 US US16/227,801 patent/US10611777B2/en active Active
-
2019
- 2019-12-18 HR HRP20192279TT patent/HRP20192279T1/hr unknown
-
2020
- 2020-01-08 CY CY20201100013T patent/CY1122763T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20192279T1 (hr) | Novi spojevi imidazopiridazina i njihova uporaba | |
| HRP20170295T1 (hr) | Oblik soli inhibitora ljudske histonske metiltransferaze ezh2 | |
| HRP20161547T1 (hr) | Derivati 5-fluor-n-(piridin-2-il)piridin-2-amina koji sadrže sulfoksiminsku skupinu | |
| HRP20171638T1 (hr) | Derivati pirazolin diona kao inhibitori nadph oksidaze | |
| HRP20160852T1 (hr) | Biciklični heterociklični spojevi kao inhibitori protein tirozin kinaze | |
| HRP20100670T1 (hr) | Aril-supstituirani pirazol-amid spojevi korisni kao inhibitori kinaze | |
| PE20160995A1 (es) | Inhibidores de syk | |
| HRP20221207T1 (hr) | Supstituirani biciklički heterociklički spojevi kao inhibitori prmt5 | |
| JP2017511357A5 (hr) | ||
| AR099379A1 (es) | Compuestos tricíclicos como agentes antineoplásicos | |
| JP2016506962A5 (hr) | ||
| GEP20186840B (en) | Pyrrolo [2,3-d] pyrimidinyl, pyrrolo [2,3-b] pyrazinyl and pyrrolo [2,3-d] pyridinyl acrylamides | |
| SI3102573T1 (en) | SUBSTITUTED TIAZOL OR OXASOL AS ANTAGONISTS OF THE RECEPTOR P2X7 | |
| JP2014506599A5 (hr) | ||
| RS54708B1 (en) | ARYLETINYL DERIVATIVES | |
| AR107042A1 (es) | Inhibidores de la tirosina quinasa de bruton y métodos de su uso | |
| JP2017538769A5 (hr) | ||
| AR065333A1 (es) | Antagonistas del receptor de dopamina 2 de rapida disociacion | |
| HRP20110515T1 (hr) | Derivati 7-alkinil-1,8-naftiridinona, njihovo dobivanje i njihova upotreba u terapiji | |
| GEP20207128B (en) | Aminothiazole derivatives useful as antiviral agents | |
| JP2020508327A5 (hr) | ||
| SG10201806809QA (en) | 1-heterocyclyl isochromanyl compounds and analogs for treating cns disorders | |
| HRP20110550T1 (hr) | Derivati 7-alkinil-1,8-naftiridinona, njihovo dobivanje i njihova upotreba u terapiji | |
| MX2016009581A (es) | Derivados de 6-fenil- o 6-(piridin-3-il) indazol y metodos de uso. | |
| AR074325A1 (es) | Compuesto de 1-(arilsulfonil)-4-(piperazin-1-il)-1h-benzimidazole, composicion y medicamento que lo comprende y uso y metodo de sintesis del compuesto |