HRP20180122T1 - Derivat pirazina - Google Patents
Derivat pirazina Download PDFInfo
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- HRP20180122T1 HRP20180122T1 HRP20180122TT HRP20180122T HRP20180122T1 HR P20180122 T1 HRP20180122 T1 HR P20180122T1 HR P20180122T T HRP20180122T T HR P20180122TT HR P20180122 T HRP20180122 T HR P20180122T HR P20180122 T1 HRP20180122 T1 HR P20180122T1
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- Croatia
- Prior art keywords
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- pharmaceutically acceptable
- acceptable salt
- methyl
- solvate
- Prior art date
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- 150000003216 pyrazines Chemical class 0.000 title claims 18
- 150000003839 salts Chemical class 0.000 claims 18
- 239000012453 solvate Substances 0.000 claims 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000006773 (C2-C7) alkylcarbonyl group Chemical group 0.000 claims 2
- DCYTULXIJQTPEW-UHFFFAOYSA-N 2-(6-cyanopyrazin-2-yl)-3-[(2,5-dichlorophenyl)methyl]-5-methylimidazole-4-carboxylic acid Chemical compound C(#N)C1=CN=CC(=N1)C=1N(C(=C(N=1)C)C(=O)O)CC1=C(C=CC(=C1)Cl)Cl DCYTULXIJQTPEW-UHFFFAOYSA-N 0.000 claims 2
- YQIRMNZWWRIXHU-UHFFFAOYSA-N 2-(6-cyclopropylpyrazin-2-yl)-3-[(2,5-dichlorophenyl)methyl]-5-methylimidazole-4-carboxylic acid Chemical compound C1(CC1)C1=CN=CC(=N1)C=1N(C(=C(N=1)C)C(=O)O)CC1=C(C=CC(=C1)Cl)Cl YQIRMNZWWRIXHU-UHFFFAOYSA-N 0.000 claims 2
- UFAXIQXKXNRNKK-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-2-(6-ethoxypyrazin-2-yl)-5-methylimidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC(=CN=C2)OCC)C=C(C=C1)Cl UFAXIQXKXNRNKK-UHFFFAOYSA-N 0.000 claims 2
- TZATXNVJILUVCE-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-2-(6-ethylpyrazin-2-yl)-5-methylimidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC(=CN=C2)CC)C=C(C=C1)Cl TZATXNVJILUVCE-UHFFFAOYSA-N 0.000 claims 2
- KRBUOYHOAMZQPB-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-2-(6-methoxypyrazin-2-yl)-5-methylimidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC(=CN=C2)OC)C=C(C=C1)Cl KRBUOYHOAMZQPB-UHFFFAOYSA-N 0.000 claims 2
- HMKGBOBTFIOBCI-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-5-methyl-2-(6-methylpyrazin-2-yl)imidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC(=CN=C2)C)C=C(C=C1)Cl HMKGBOBTFIOBCI-UHFFFAOYSA-N 0.000 claims 2
- GQAGKBUYGPOSML-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-5-methyl-2-(6-phenoxypyrazin-2-yl)imidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC(=CN=C2)OC2=CC=CC=C2)C=C(C=C1)Cl GQAGKBUYGPOSML-UHFFFAOYSA-N 0.000 claims 2
- KWPRUZXMSRFIMD-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-5-methyl-2-(6-phenylpyrazin-2-yl)imidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC(=CN=C2)C2=CC=CC=C2)C=C(C=C1)Cl KWPRUZXMSRFIMD-UHFFFAOYSA-N 0.000 claims 2
- SOCRBZIALSDUNY-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-5-methyl-2-(6-propan-2-ylpyrazin-2-yl)imidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC(=CN=C2)C(C)C)C=C(C=C1)Cl SOCRBZIALSDUNY-UHFFFAOYSA-N 0.000 claims 2
- FVWVMNATKMYAFH-UHFFFAOYSA-N 3-[(2,5-dichlorophenyl)methyl]-5-methyl-2-pyrazin-2-ylimidazole-4-carboxylic acid Chemical compound ClC1=C(CN2C(=NC(=C2C(=O)O)C)C2=NC=CN=C2)C=C(C=C1)Cl FVWVMNATKMYAFH-UHFFFAOYSA-N 0.000 claims 2
- DDBVXDKQUBUDMO-UHFFFAOYSA-N 3-[(2,5-dichlorothiophen-3-yl)methyl]-5-methyl-2-(6-methylpyrazin-2-yl)imidazole-4-carboxylic acid Chemical compound ClC=1SC(=CC=1CN1C(=NC(=C1C(=O)O)C)C1=NC(=CN=C1)C)Cl DDBVXDKQUBUDMO-UHFFFAOYSA-N 0.000 claims 2
- VFFJZSIWAWTRLZ-UHFFFAOYSA-N 3-[(2,5-dichlorothiophen-3-yl)methyl]-5-methyl-2-pyrazin-2-ylimidazole-4-carboxylic acid Chemical compound ClC=1SC(=CC=1CN1C(=NC(=C1C(=O)O)C)C1=NC=CN=C1)Cl VFFJZSIWAWTRLZ-UHFFFAOYSA-N 0.000 claims 2
- CUFJEDGLCSGVEN-UHFFFAOYSA-N 3-benzyl-2-[6-(2-fluoro-6-methoxyphenoxy)pyrazin-2-yl]-5-methylimidazole-4-carboxylic acid Chemical compound C(C1=CC=CC=C1)N1C(=NC(=C1C(=O)O)C)C1=NC(=CN=C1)OC1=C(C=CC=C1OC)F CUFJEDGLCSGVEN-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- OTQIKKBNIWNDHC-UHFFFAOYSA-N 1-[(2,5-dichlorophenyl)methyl]-5-pyrazin-2-ylpyrrole-2-carboxylic acid Chemical compound ClC1=C(CN2C(=CC=C2C(=O)O)C2=NC=CN=C2)C=C(C=C1)Cl OTQIKKBNIWNDHC-UHFFFAOYSA-N 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 201000001431 Hyperuricemia Diseases 0.000 claims 1
- 208000009625 Lesch-Nyhan syndrome Diseases 0.000 claims 1
- 208000035317 Total hypoxanthine-guanine phosphoribosyl transferase deficiency Diseases 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- 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
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- Heart & Thoracic Surgery (AREA)
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- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Liquid Crystal Substances (AREA)
Claims (17)
1. Derivat pirazina predstavljen sa slijedećom formulom (I) ili njegova farmaceutski prihvatljiva sol, ili njegov solvat:
[image]
pri čemu,
X1 predstavlja dušikov atom ili CH;
R1 predstavlja vodikov atom, skupinu C1-C6 alkil, skupinu C3-C6 cikloalkil, skupinu C2-C6 alkenil, skupinu C2-C6 alkinil, halogeni atom, trifluorometilnu skupinu, difluorometilnu skupinu, cijano skupinu, skupinu C2-C7 alkilkarbonil, skupinu C1-C6 alkilsulfonil, nitro skupinu, amino skupinu, skupinu di(C1-C6 alkil)amino, formil skupinu, hidroksil skupinu, skupinu C1-C6 alkoksi, skupinu C1-C6 alkiltio, ili fenilnu skupinu ili fenoksi skupinu koje mogu biti supstituirane s 1 do 3 Ra';
Ra predstavlja halogeni atom, skupinu C1-C6 alkil, skupinu C3-C6 cikloalkil, ili skupinu C1-C6 alkoksi;
R2 predstavlja skupinu C1-C6 alkil, skupinu C3-C6 cikloalkil, ili skupinu C1-C6 alkoksi;
p predstavlja bilo koji cijeli broj od 0 do 2;
R3 predstavlja vodikov atom, skupinu C1-C6 alkil, skupinu C3-C6 cikloalkil, skupinu C2-C6 alkenil, skupinu C2-C6 alkinil, skupinu C1-C6 alkoksi, skupinu C2-C7 alkilkarbonil, skupinu C1-C6 alkiltio, halogeni atom, trifluorometilnu skupinu, difluorometilnu skupinu, cijano skupinu, fenilnu skupinu, piridil skupinu, fenoksi skupinu, ili COORb;
R4 predstavlja tetrazolil skupinu, -COORc, -CONHSO2-(C1-C6 alkil), ili bilo koju od slijedećih skupina:
[image]
Rb i Rc mogu biti isti ili različiti i predstavljaju vodikov atom, ili skupinu C1-C6 alkil;
Z predstavlja bilo koju od slijedećih skupina predstavljenih sa Z1 do Z7:
[image]
R5 predstavlja vodikov atom ili skupinu C1-C6 alkil;
R6 i R7 mogu biti isti ili različiti i predstavljaju vodikov atom, halogeni atom, skupinu C1-C6 alkil, skupinu C1-C6 alkoksi, trifluorometilnu skupinu, trifluorometoksi skupinu, cijano skupinu, nitro skupinu, ili fenoksi skupinu,
ili R6 i R7 zajedno tvore skupinu C1- C3 alkilendioksi;
R8, R9, R10, R11, R12, R13, R14, i R15 svaki neovisno predstavljaju vodikov atom, halogeni atom, skupinu C1-C6 alkil, skupinu C1-C6 alkoksi, difluorometilnu skupinu, trifluorometilnu skupinu, cijano skupinu, ili skupinu di(C1-C6 alkil)amino;
R16 i R17 mogu biti isti ili različiti i predstavljaju halogeni atom;
q i r neovisno predstavljaju 0 ili 1;
W predstavlja sumporov atom, kisikov atom, ili NRd; i
Rd predstavlja vodikov atom, skupinu C1-C6 alkil, ili benzilnu skupinu.
2. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema zahtjevu 1, naznačen time da X1 je dušikov atom.
3. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema zahtjevu 1, naznačen time da X1 je CH.
4. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 3, naznačen time da R1 predstavlja vodikov atom, skupinu C1-C6 alkil, skupinu C3-C6 cikloalkil, halogeni atom, trifluorometilnu skupinu, cijano skupinu, hidroksil skupinu, skupinu C1-C6 alkoksi, fenilnu skupinu, ili fenoksi skupinu.
5. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 3, naznačen time da R1 predstavlja vodikov atom, metilnu skupinu, etilnu skupinu, ciklopropilnu skupinu, izopropilnu skupinu, metoksi skupinu, etoksi skupinu, cijano skupinu, hidroksil skupinu, fenilnu skupinu, ili fenoksi skupinu.
6. Derivat pirazina predstavljen sa slijedećom formulom (Ia) ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 5:
[image]
naznačen time da X1, R1, R2, R3, R4, p, i Z su isti kako je definirano iznad.
7. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 6, naznačen time da R3 je vodikov atom, skupina C1- C6 alkil, ili halogeni atom.
8. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 6, naznačen time da R3 je vodikov atom, metilna skupina, ili klorov atom.
9. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 8, naznačen time da R4 je -COORc.
10. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 8, naznačen time da R4 je karboksilna skupina.
11. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 10, naznačen time da Z predstavlja Z1 ili Z2, i W predstavlja sumporov atom.
12. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 10, naznačen time da Z predstavlja slijedeću formulu Z1a ili Z2a:
[image]
pri čemu, R5, R6, R7, R8, i R9 su isti kako je definirano iznad.
13. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 12, naznačen time da R5 predstavlja vodikov atom; i R6, R7, R8, i R9 svaki neovisno predstavljaju vodikov atom, halogeni atom, ili skupinu C1-C6 alkil.
14. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema bilo kojem od zahtjeva 1 do 13, naznačen time da p predstavlja 0.
15. Derivat pirazina ili njegova farmaceutski prihvatljiva sol, ili njegov solvat prema zahtjevu 1, naznačen time da je odabran od sljedećih spojeva (1) do (14) ili od njihove farmaceutski prihvatljive soli, ili njihovog solvata:
(1) 1-(2,5-diklorobenzil)-4-metil-2-(pirazin-2-il)-1H-imidazol-5-karboksilna kiselina
(2) 1-(2,5-diklorobenzil)-4-metil-2-(6-metilpirazin-2-il)-1H-imidazol-5-karboksilna kiselina
(3) 1-(2,5-diklorobenzil)-2-(6-etilpirazin-2-il)-4-metil-1H-imidazol-5-karboksilna kiselina
(4) 1-(2,5-diklorobenzil)-4-metil-2-(6-fenilpirazin-2-il)-1H-imidazol-5-karboksilna kiselina
(5) 1-(2,5-diklorobenzil)-2-(6-metoksipirazin-2-il)-4-metil-1H-imidazol-5-karboksilna kiselina
(6) 1-(2,5-diklorobenzil)-4-metil-2-(6-fenoksipirazin-2-il)-1H-imidazol-5-karboksilna kiselina
(7) 1-(2,5-diklorobenzil)-2-(6-etoksipirazin-2-il)-4-metil-1H-imidazol-5-karboksilna kiselina
(8) 2-(6-cijanopirazin -2-il)-1-(2,5-diklorobenzil)-4-metil-1H-imidazol-5-karboksilna kiselina
(9) 1-(2,5-diklorobenzil)-2-(6-izopropilpirazin-2-il)-4-metil-1H-imidazol-5-karboksilna kiselina
(10) 2-(6-ciklopropilpirazin-2-il)-1-(2,5-diklorobenzil)-4-metil-1H- imidazol-5-karboksilna kiselina
(11) 1-((2,5-diklorotiofene-3-il)metil)-4-metil-2-(pirazin-2-il)-1H-imidazol-5- karboksilna kiselina
(12) 1-((2,5-diklorotiofene-3-il)metil)-4-metil-2-(6-metilpirazin-2-il)-1H-imidazol-5-karboksilna kiselina
(13) 1-benzil-2-(6-(2-fluoro-6-metoksifenoksi)pirazin-2-il)-4-metil-1H-imidazol-5-karboksilna kiselina
(14) 1-(2,5-diklorobenzil)-2-(pirazin-2-il)-1H-pirrole-5-karboksilna kiselina.
16. Farmaceutski pripravak naznačen time da sadrži derivat pirazina ili njegovu farmaceutski prihvatljivu sol, ili njegov solvat u skladu s bilo kojim od zahtjeva 1 do 15; i farmaceutski prihvatljiv nosač.
17. Terapijsko sredstvo ili preventivno sredstvo koje sadrži derivat pirazina ili njegovu farmaceutski prihvatljivu sol, ili njegov solvat u skladu s bilo kojim od zahtjeva 1 do 15, naznačeno time da je namijenjeno upotrebi u terapiji ili prevenciji jedne ili više bolesti izabranih iz skupine koja se sastoji od gihta, hiperurikemije, hipertenzije, bolesti bubrega, dijabetesa, arterioskleroze, ili sindroma Lesch-Nyhan.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2014099677 | 2014-05-13 | ||
| PCT/JP2015/063654 WO2015174417A1 (ja) | 2014-05-13 | 2015-05-12 | ピラジン誘導体 |
| EP15792266.7A EP3144306B1 (en) | 2014-05-13 | 2015-05-12 | Pyrazine derivative |
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| Publication Number | Publication Date |
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| HRP20180122T1 true HRP20180122T1 (hr) | 2018-02-23 |
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| HRP20180122TT HRP20180122T1 (hr) | 2014-05-13 | 2018-01-23 | Derivat pirazina |
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| US (1) | US9856237B2 (hr) |
| EP (1) | EP3144306B1 (hr) |
| JP (1) | JP6173576B2 (hr) |
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| AR (1) | AR100403A1 (hr) |
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| CY (1) | CY1119876T1 (hr) |
| DK (1) | DK3144306T3 (hr) |
| ES (1) | ES2654434T3 (hr) |
| HR (1) | HRP20180122T1 (hr) |
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| LT (1) | LT3144306T (hr) |
| ME (1) | ME02978B (hr) |
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| RU (1) | RU2016148735A (hr) |
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| CN116496198A (zh) * | 2023-06-26 | 2023-07-28 | 中山大学肿瘤防治中心（中山大学附属肿瘤医院、中山大学肿瘤研究所） | 一种4-羟基-2'-(1-苄基-5-硝基吡咯甲叉)-苯甲酰肼衍生物及其制备方法和应用 |
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| JP4397875B2 (ja) * | 1997-02-05 | 2010-01-13 | 第一三共株式会社 | 糖尿病合併症予防薬又は治療薬 |
| AU5576498A (en) * | 1997-02-05 | 1998-08-26 | Sankyo Company Limited | Prophylactic or therapeutic agent for diabetic complication |
| EP1583742B1 (en) * | 2003-01-02 | 2009-12-02 | F. Hoffmann-La Roche Ag | Cb 1 receptour inverse agonists |
| JP2007145786A (ja) * | 2005-11-30 | 2007-06-14 | Toray Ind Inc | ピラジン誘導体及びそれを有効成分とする腎炎治療薬 |
| WO2008126899A1 (ja) * | 2007-04-11 | 2008-10-23 | Kissei Pharmaceutical Co., Ltd. | ５員環へテロ環誘導体及びその医薬用途 |
| AR081930A1 (es) | 2010-06-16 | 2012-10-31 | Ardea Biosciences Inc | Compuestos de tioacetato |
| HUE037736T2 (hu) | 2012-11-14 | 2018-09-28 | Teijin Pharma Ltd | Piridin származékok |
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| Publication number | Publication date |
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| CY1119876T1 (el) | 2018-06-27 |
| NO3144306T3 (hr) | 2018-04-14 |
| SG11201609359WA (en) | 2016-12-29 |
| WO2015174417A1 (ja) | 2015-11-19 |
| AR100403A1 (es) | 2016-10-05 |
| US9856237B2 (en) | 2018-01-02 |
| MX2016014693A (es) | 2017-02-23 |
| PH12016502223A1 (en) | 2017-02-06 |
| PT3144306T (pt) | 2018-01-08 |
| DK3144306T3 (en) | 2018-01-02 |
| TW201609702A (zh) | 2016-03-16 |
| LT3144306T (lt) | 2018-01-10 |
| HUE035728T2 (en) | 2018-05-28 |
| PL3144306T3 (pl) | 2018-04-30 |
| SI3144306T1 (en) | 2018-02-28 |
| CA2948797A1 (en) | 2015-11-19 |
| KR20170004998A (ko) | 2017-01-11 |
| IL248900A0 (en) | 2017-01-31 |
| JPWO2015174417A1 (ja) | 2017-04-20 |
| AU2015260300A1 (en) | 2016-12-22 |
| EP3144306A1 (en) | 2017-03-22 |
| ES2654434T3 (es) | 2018-02-13 |
| CN106458998A (zh) | 2017-02-22 |
| EP3144306A4 (en) | 2017-03-22 |
| RU2016148735A (ru) | 2018-06-19 |
| ME02978B (me) | 2018-10-20 |
| RS56837B1 (sr) | 2018-04-30 |
| EP3144306B1 (en) | 2017-11-15 |
| JP6173576B2 (ja) | 2017-08-02 |
| US20170152242A1 (en) | 2017-06-01 |
| RU2016148735A3 (hr) | 2018-06-19 |
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