MXPA06003525A - Derivados de pirimidin-2-amina y su uso como antagonistas del receptor de adenosina a2b. - Google Patents
Derivados de pirimidin-2-amina y su uso como antagonistas del receptor de adenosina a2b.Info
- Publication number
- MXPA06003525A MXPA06003525A MXPA06003525A MXPA06003525A MXPA06003525A MX PA06003525 A MXPA06003525 A MX PA06003525A MX PA06003525 A MXPA06003525 A MX PA06003525A MX PA06003525 A MXPA06003525 A MX PA06003525A MX PA06003525 A MXPA06003525 A MX PA06003525A
- Authority
- MX
- Mexico
- Prior art keywords
- optionally substituted
- group
- bipyrimidin
- furyl
- branched lower
- Prior art date
Links
- 101150078577 Adora2b gene Proteins 0.000 title abstract description 5
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 title description 9
- 229940121359 adenosine receptor antagonist Drugs 0.000 title 1
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 51
- 230000008569 process Effects 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 70
- -1 cyano- Chemical class 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000004414 alkyl thio group Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000004043 oxo group Chemical group O=* 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 14
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 102000005962 receptors Human genes 0.000 claims description 8
- 108020003175 receptors Proteins 0.000 claims description 8
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 7
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 229960005305 adenosine Drugs 0.000 claims description 7
- 230000001575 pathological effect Effects 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 102000007470 Adenosine A2B Receptor Human genes 0.000 claims description 6
- 108010085273 Adenosine A2B receptor Proteins 0.000 claims description 6
- 108050000203 Adenosine receptors Proteins 0.000 claims description 6
- 102000009346 Adenosine receptors Human genes 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 230000006872 improvement Effects 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000026935 allergic disease Diseases 0.000 claims description 5
- 230000008485 antagonism Effects 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 208000017442 Retinal disease Diseases 0.000 claims description 4
- 206010038923 Retinopathy Diseases 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 230000007885 bronchoconstriction Effects 0.000 claims description 4
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 208000031225 myocardial ischemia Diseases 0.000 claims description 4
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- GIFAHWUNLKIYPK-UHFFFAOYSA-N 2-[[4-(2-methyl-5-pyridin-4-ylpyrimidin-4-yl)phenoxy]methyl]quinoline Chemical group C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NC(C)=NC=C1C1=CC=NC=C1 GIFAHWUNLKIYPK-UHFFFAOYSA-N 0.000 claims 1
- UOPAUGXJSSLKIS-UHFFFAOYSA-N 4-(furan-2-yl)-n-(1-oxidopyridin-1-ium-3-yl)-5-pyrimidin-4-ylpyrimidin-2-amine Chemical compound [O-][N+]1=CC=CC(NC=2N=C(C(C=3N=CN=CC=3)=CN=2)C=2OC=CC=2)=C1 UOPAUGXJSSLKIS-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 55
- 239000005557 antagonist Substances 0.000 abstract description 5
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 43
- 230000014759 maintenance of location Effects 0.000 description 38
- 239000000203 mixture Substances 0.000 description 20
- 239000000872 buffer Substances 0.000 description 14
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- 239000012528 membrane Substances 0.000 description 10
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 8
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- LVILGAOSPDLNRM-UHFFFAOYSA-N 4-methylpyrimidine Chemical compound CC1=CC=NC=N1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 description 4
- 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 4
- 102000055025 Adenosine deaminases Human genes 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
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- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 4
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
- XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero 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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
- A61P11/08—Bronchodilators
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- 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]
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- 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
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- 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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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Epidemiology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200302275A ES2229928B1 (es) | 2003-10-02 | 2003-10-02 | Nuevos derivados de pirimidin-2-amina. |
| PCT/EP2004/010644 WO2005040155A1 (en) | 2003-10-02 | 2004-09-22 | Pyrimidin-2-amine derivates and their use as a2b adenosine receptor antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06003525A true MXPA06003525A (es) | 2006-06-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| MXPA06003525A MXPA06003525A (es) | 2003-10-02 | 2004-09-22 | Derivados de pirimidin-2-amina y su uso como antagonistas del receptor de adenosina a2b. |
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| Country | Link |
|---|---|
| US (1) | US20070265273A1 (enExample) |
| EP (1) | EP1668000A1 (enExample) |
| JP (1) | JP2007507443A (enExample) |
| KR (1) | KR20060097010A (enExample) |
| CN (1) | CN1886402A (enExample) |
| AR (1) | AR046170A1 (enExample) |
| AU (1) | AU2004283800B8 (enExample) |
| BR (1) | BRPI0415324A (enExample) |
| CA (1) | CA2540765A1 (enExample) |
| CO (1) | CO5690593A2 (enExample) |
| EC (1) | ECSP066426A (enExample) |
| ES (1) | ES2229928B1 (enExample) |
| IL (1) | IL174771A0 (enExample) |
| MX (1) | MXPA06003525A (enExample) |
| NO (1) | NO20061952L (enExample) |
| NZ (1) | NZ546266A (enExample) |
| PE (1) | PE20050473A1 (enExample) |
| RU (1) | RU2006114746A (enExample) |
| SG (1) | SG149077A1 (enExample) |
| TW (1) | TW200526645A (enExample) |
| UA (1) | UA82563C2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2311462A1 (en) | 2004-10-15 | 2011-04-20 | Cv Therapeutics, Inc. | Method of preventing and treating airway remodeling and pulmonary inflammation using A2B adenosine receptor antagonists |
| ES2270715B1 (es) * | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| ES2274712B1 (es) * | 2005-10-06 | 2008-03-01 | Laboratorios Almirall S.A. | Nuevos derivados imidazopiridina. |
| DE102006046410A1 (de) * | 2006-09-20 | 2008-03-27 | Eberhard-Karls-Universität Tübingen Universitätsklinikum | Arzneimittel zur Prophylaxe oder Behandlung oder Diagnostik von ischämischen Krankheiten |
| ES2303776B1 (es) * | 2006-12-29 | 2009-08-07 | Laboratorios Almirall S.A. | Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b. |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| CN101679376A (zh) * | 2007-06-08 | 2010-03-24 | 拜尔农科股份有限公司 | 杀真菌剂杂环-嘧啶基-氨基衍生物 |
| MX2010001020A (es) * | 2007-07-26 | 2010-03-01 | Novartis Ag | Derivados de pirimidina utiles para el tratamiento de condiciones inflamatorias o alergicas. |
| AU2008289037B2 (en) | 2007-08-22 | 2012-03-01 | Novartis Ag | 5- (4- (haloalkoxy) phenyl) pyrimidine-2-amine compounds and compositions as kinase inhibitors |
| EA017392B1 (ru) * | 2007-08-22 | 2012-12-28 | Айрм Ллк | Производные 2-гетероариламинопиримидина в качестве ингибиторов киназ |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| EP2308866A1 (de) | 2009-10-09 | 2011-04-13 | Bayer CropScience AG | Phenylpyri(mi)dinylpyrazole und ihre Verwendung als Fungizide |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| WO2011076725A1 (en) | 2009-12-21 | 2011-06-30 | Bayer Cropscience Ag | Thienylpyri (mi) dinylazole and their use for controlling phytopathogenic fungi |
| ES2579949T3 (es) * | 2010-02-05 | 2016-08-17 | Heptares Therapeutics Limited | Derivados de 1,2,4-triazin-4-amina |
| EA201390917A1 (ru) | 2010-12-21 | 2013-12-30 | Новартис Аг | Дигетероарильные соединения в качестве ингибиторов vps34 |
| WO2020146795A1 (en) | 2019-01-11 | 2020-07-16 | Omeros Corporation | Methods and compositions for treating cancer |
| CN112608316B (zh) | 2019-07-30 | 2022-10-21 | 厦门宝太生物科技股份有限公司 | 一种吡唑并三嗪类腺苷受体拮抗剂 |
| CN112592354B (zh) | 2019-07-30 | 2022-05-27 | 厦门宝太生物科技股份有限公司 | 一种异噁唑并嘧啶类杂环化合物的制备方法 |
| CN115477653B (zh) * | 2022-10-11 | 2024-04-09 | 安徽省庆云医药股份有限公司 | 一种曲拉西利关键中间体及曲拉西利的制备方法 |
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| US5686470A (en) * | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
| AU2001252606B2 (en) * | 2000-04-26 | 2005-07-07 | Eisai R&D Management Co., Ltd. | Medicinal compositions promoting bowel movement |
| US6641549B2 (en) * | 2001-02-05 | 2003-11-04 | Bsn Medical, Inc. | Custom-moldable support for patellar tendinitis |
| TWI330183B (enExample) * | 2001-10-22 | 2010-09-11 | Eisai R&D Man Co Ltd | |
| WO2003057689A1 (en) * | 2002-01-02 | 2003-07-17 | Fujisawa Pharmaceutical Co., Ltd. | Aminopyrimidine compounds, processes for their preparation and pharmaceutical compositions containing them |
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- 2004-09-22 MX MXPA06003525A patent/MXPA06003525A/es unknown
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| ZA200602139B (en) | 2007-06-27 |
| NO20061952L (no) | 2006-06-26 |
| CO5690593A2 (es) | 2006-10-31 |
| NZ546266A (en) | 2008-10-31 |
| UA82563C2 (uk) | 2008-04-25 |
| KR20060097010A (ko) | 2006-09-13 |
| AU2004283800B2 (en) | 2009-05-07 |
| RU2006114746A (ru) | 2007-11-20 |
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| WO2005040155A1 (en) | 2005-05-06 |
| BRPI0415324A (pt) | 2006-12-05 |
| JP2007507443A (ja) | 2007-03-29 |
| PE20050473A1 (es) | 2005-08-24 |
| EP1668000A1 (en) | 2006-06-14 |
| ES2229928A1 (es) | 2005-04-16 |
| TW200526645A (en) | 2005-08-16 |
| US20070265273A1 (en) | 2007-11-15 |
| IL174771A0 (en) | 2006-08-20 |
| WO2005040155A8 (en) | 2006-04-20 |
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| CN1886402A (zh) | 2006-12-27 |
| CA2540765A1 (en) | 2005-05-06 |
| UY28529A1 (es) | 2005-04-29 |
| ES2229928B1 (es) | 2006-07-01 |
| AU2004283800B8 (en) | 2009-06-18 |
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