ZA200509436B - [1,2,4]triazolo[,5-A]pyrimidin-2-ylurea derivative and use thereof - Google Patents
[1,2,4]triazolo[,5-A]pyrimidin-2-ylurea derivative and use thereof Download PDFInfo
- Publication number
- ZA200509436B ZA200509436B ZA200509436A ZA200509436A ZA200509436B ZA 200509436 B ZA200509436 B ZA 200509436B ZA 200509436 A ZA200509436 A ZA 200509436A ZA 200509436 A ZA200509436 A ZA 200509436A ZA 200509436 B ZA200509436 B ZA 200509436B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- triazolo
- alpyrimidin
- substituent
- acceptable salt
- Prior art date
Links
- DNENQQPLJPZMGZ-UHFFFAOYSA-N pyrimidin-2-ylurea Chemical class NC(=O)NC1=NC=CC=N1 DNENQQPLJPZMGZ-UHFFFAOYSA-N 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 230000030741 antigen processing and presentation Effects 0.000 claims abstract description 12
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 10
- 230000003449 preventive effect Effects 0.000 claims abstract description 9
- 239000000411 inducer Substances 0.000 claims abstract description 6
- 208000026935 allergic disease Diseases 0.000 claims abstract description 5
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 4
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 4
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 3
- 208000024908 graft versus host disease Diseases 0.000 claims abstract description 3
- -1 pyrrolidin-l-ylcarbonyl group Chemical group 0.000 claims description 83
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 230000006058 immune tolerance Effects 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 230000001225 therapeutic effect Effects 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 239000003018 immunosuppressive agent Substances 0.000 claims description 7
- 229940125721 immunosuppressive agent Drugs 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 210000004698 lymphocyte Anatomy 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 206010029164 Nephrotic syndrome Diseases 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 206010028417 myasthenia gravis Diseases 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 208000032467 Aplastic anaemia Diseases 0.000 claims description 2
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims description 2
- 208000009137 Behcet syndrome Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 230000035755 proliferation Effects 0.000 claims description 2
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 5
- 239000004202 carbamide Substances 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 239000003112 inhibitor Substances 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 2
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 1
- 206010002198 Anaphylactic reaction Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010003645 Atopy Diseases 0.000 claims 1
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 claims 1
- 208000032027 Essential Thrombocythemia Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000003250 Mixed connective tissue disease Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 206010048908 Seasonal allergy Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 206010043781 Thyroiditis chronic Diseases 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 230000036783 anaphylactic response Effects 0.000 claims 1
- 208000003455 anaphylaxis Diseases 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 230000011748 cell maturation Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 210000000056 organ Anatomy 0.000 abstract description 6
- 210000001185 bone marrow Anatomy 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 230000001900 immune effect Effects 0.000 abstract 2
- SRNKZYRMFBGSGE-UHFFFAOYSA-N [1,2,4]triazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CN=C21 SRNKZYRMFBGSGE-UHFFFAOYSA-N 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 7
- 210000004443 dendritic cell Anatomy 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 239000000427 antigen Substances 0.000 description 6
- 108091007433 antigens Proteins 0.000 description 6
- 102000036639 antigens Human genes 0.000 description 6
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- 229930105110 Cyclosporin A Natural products 0.000 description 4
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 4
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- HZQDCMWJEBCWBR-UUOKFMHZSA-N Mizoribine Chemical compound OC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 HZQDCMWJEBCWBR-UUOKFMHZSA-N 0.000 description 3
- 210000001744 T-lymphocyte Anatomy 0.000 description 3
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 3
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- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 description 3
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- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 3
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- IDINUJSAMVOPCM-INIZCTEOSA-N n-[(1s)-2-[4-(3-aminopropylamino)butylamino]-1-hydroxy-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide Chemical compound NCCCNCCCCNC(=O)[C@H](O)NC(=O)CCCCCCN=C(N)N IDINUJSAMVOPCM-INIZCTEOSA-N 0.000 description 2
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Classifications
-
- 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
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- 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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- A61P37/02—Immunomodulators
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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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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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
- A61P37/08—Antiallergic agents
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- 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
- A61P5/00—Drugs for disorders of the endocrine system
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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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
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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
- A61P7/06—Antianaemics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Neurosurgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Transplantation (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003157663 | 2003-06-03 |
Publications (1)
| Publication Number | Publication Date |
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| ZA200509436B true ZA200509436B (en) | 2007-03-28 |
Family
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Family Applications (1)
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| ZA200509436A ZA200509436B (en) | 2003-06-03 | 2004-06-02 | [1,2,4]triazolo[,5-A]pyrimidin-2-ylurea derivative and use thereof |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7598244B2 (fr) |
| EP (1) | EP1630165B1 (fr) |
| JP (1) | JP4698419B2 (fr) |
| KR (1) | KR101097479B1 (fr) |
| CN (1) | CN1809570B (fr) |
| AT (1) | ATE462705T1 (fr) |
| AU (1) | AU2004245351B2 (fr) |
| BR (1) | BRPI0410867A (fr) |
| CA (1) | CA2526211C (fr) |
| DE (1) | DE602004026298D1 (fr) |
| RU (1) | RU2348636C2 (fr) |
| TW (1) | TWI334868B (fr) |
| WO (1) | WO2004108729A1 (fr) |
| ZA (1) | ZA200509436B (fr) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005104895A (ja) * | 2003-09-30 | 2005-04-21 | Nippon Kayaku Co Ltd | 光学活性なアミノアルコール化合物の製造法 |
| JP4606015B2 (ja) * | 2003-11-25 | 2011-01-05 | 日本化薬株式会社 | ［１，２，４］トリアゾロ［１，５−ａ］ピリミジン誘導体の新規医薬用途 |
| CN101018774A (zh) * | 2004-07-20 | 2007-08-15 | 锡耶纳生物技术股份公司 | α7烟碱性乙酰胆碱受体的调节剂和其治疗用途 |
| EP1991528A2 (fr) * | 2006-01-18 | 2008-11-19 | Siena Biotech S.p.A. | Modulateurs de la sous-unité alpha 7 du récepteur nicotinique de l'acétylcholine et leurs applications thérapeutiques |
| ES2436109T3 (es) * | 2006-02-09 | 2013-12-27 | Belrose Pharma Inc. | Conjugados poliméricos de múltiples brazos de 7-etil-10-hidroxicamptotecina para el tratamiento del cáncer de mama, del cáncer colorrectal, del cáncer de páncreas, de ovario y de pulmón |
| GB0612630D0 (en) * | 2006-06-26 | 2006-08-02 | Novartis Ag | Organic compounds |
| CL2008000119A1 (es) * | 2007-01-16 | 2008-05-16 | Wyeth Corp | Compuestos derivados de pirazol, antagonistas del receptor nicotinico de acetilcolina; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como demencia senil, alzheimer y esquizofrenia. |
| KR100844125B1 (ko) | 2007-03-23 | 2008-07-04 | 한국화학연구원 | 7-(3′,4′-디알콕시페닐)-[1,2,4]트리아졸로[1,5-ａ]피리미딘 화합물, 이의 제조방법 및 이를 포함하는 천식 및만성폐쇄성 폐질환을 포함한 염증관련 질환, 관절염,아토피 피부염, 암 및 뇌질환의 치료 및 예방을 위한약제학적 조성물 |
| EP2444403A1 (fr) * | 2008-04-18 | 2012-04-25 | Shionogi Co., Ltd. | Composé hétérocyclique doté d'une activité inhibitrice sur PI3K |
| CN102834506A (zh) * | 2010-02-23 | 2012-12-19 | 日本化药株式会社 | 调节性树突细胞的制备方法 |
| EP2766366B1 (fr) * | 2011-09-14 | 2016-11-09 | Chiesi Farmaceutici S.p.A. | Derivees der tetrahydrotriazolopyrimidine comme inhibteurs d' elastase neutrophile humaine |
| KR102116107B1 (ko) | 2013-12-30 | 2020-05-28 | 삼성디스플레이 주식회사 | 표시 장치 |
| US9988421B2 (en) | 2014-01-10 | 2018-06-05 | Cornell University | Dipeptides as inhibitors of human immunoproteasomes |
| EP3193904A4 (fr) * | 2014-08-18 | 2018-04-11 | Cornell University | Dipeptidomimetiques en tant qu'inhibiteurs des immunoproteasomes humains |
| EP4006012A1 (fr) | 2015-10-15 | 2022-06-01 | Cornell University | Inhibiteurs de protéasome et leurs utilisations |
| US10647665B2 (en) | 2016-06-22 | 2020-05-12 | Fudan University | Biaryl urea derivative or salt thereof and preparation process and use for the same |
| CN107522641B (zh) * | 2016-06-22 | 2020-05-05 | 复旦大学 | 联芳基脲类衍生物或其盐及其制备方法和用途 |
| EP3694605A4 (fr) | 2017-10-11 | 2021-10-27 | Cornell University | Inhibiteurs peptidomimétiques du protéasome |
| WO2020010252A1 (fr) * | 2018-07-05 | 2020-01-09 | Daiichi Sankyo Company, Limited | Composé cyclique fusionné ayant une structure d'urée |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4654343A (en) * | 1985-10-31 | 1987-03-31 | American Cyanamid Company | N-substituted-N[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]alkanamides, carbamates and ureas |
| JPH01270051A (ja) * | 1988-04-22 | 1989-10-27 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| US5880066A (en) | 1990-12-11 | 1999-03-09 | Monsanto Company | Safened herbicidal sulfonamide compositions |
| US5484760A (en) | 1990-12-31 | 1996-01-16 | Monsanto Company | Herbicide antidotes as safeners for reducing phytotoxicity resulting from synergistic interaction between herbicides and other pesticides |
| JPH10206995A (ja) * | 1997-01-21 | 1998-08-07 | Konica Corp | ハロゲン化銀写真感光材料 |
| ATE311385T1 (de) * | 1999-10-27 | 2005-12-15 | Novartis Pharma Gmbh | Thiazol und imidazo(4,5-b)pyridin verbindungen und ihre verwendung als pharmazeutika |
| JP2001322933A (ja) * | 2000-05-15 | 2001-11-20 | Ucb Sa | Ｃｄ４０シグナル遮断剤 |
| AU9502601A (en) * | 2000-09-06 | 2002-03-22 | Chiron Corp | Inhibitors of glycogen synthase kinase 3 |
| US6737085B2 (en) * | 2000-11-01 | 2004-05-18 | Tokiwa Phytochemical Co., Ltd. | Apocynum venetum extract for use as antidepressant |
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2004
- 2004-06-01 TW TW093115697A patent/TWI334868B/zh not_active IP Right Cessation
- 2004-06-02 US US10/559,198 patent/US7598244B2/en not_active Expired - Fee Related
- 2004-06-02 AU AU2004245351A patent/AU2004245351B2/en not_active Ceased
- 2004-06-02 AT AT04745522T patent/ATE462705T1/de not_active IP Right Cessation
- 2004-06-02 RU RU2005137706/04A patent/RU2348636C2/ru not_active IP Right Cessation
- 2004-06-02 BR BRPI0410867-1A patent/BRPI0410867A/pt not_active IP Right Cessation
- 2004-06-02 ZA ZA200509436A patent/ZA200509436B/en unknown
- 2004-06-02 EP EP04745522A patent/EP1630165B1/fr not_active Expired - Lifetime
- 2004-06-02 JP JP2005506762A patent/JP4698419B2/ja not_active Expired - Fee Related
- 2004-06-02 WO PCT/JP2004/007623 patent/WO2004108729A1/fr active Application Filing
- 2004-06-02 CA CA2526211A patent/CA2526211C/fr not_active Expired - Fee Related
- 2004-06-02 DE DE602004026298T patent/DE602004026298D1/de not_active Expired - Lifetime
- 2004-06-02 CN CN2004800174900A patent/CN1809570B/zh not_active Expired - Fee Related
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2005
- 2005-12-02 KR KR1020057023187A patent/KR101097479B1/ko not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2526211A1 (fr) | 2004-12-16 |
| EP1630165A4 (fr) | 2007-11-21 |
| RU2348636C2 (ru) | 2009-03-10 |
| WO2004108729A1 (fr) | 2004-12-16 |
| CA2526211C (fr) | 2011-12-20 |
| AU2004245351A1 (en) | 2004-12-16 |
| ATE462705T1 (de) | 2010-04-15 |
| BRPI0410867A (pt) | 2006-07-04 |
| CN1809570A (zh) | 2006-07-26 |
| CN1809570B (zh) | 2011-06-22 |
| DE602004026298D1 (de) | 2010-05-12 |
| RU2005137706A (ru) | 2006-06-10 |
| AU2004245351B2 (en) | 2009-04-02 |
| JPWO2004108729A1 (ja) | 2006-07-20 |
| US7598244B2 (en) | 2009-10-06 |
| KR101097479B1 (ko) | 2011-12-22 |
| TW200508238A (en) | 2005-03-01 |
| EP1630165A1 (fr) | 2006-03-01 |
| TWI334868B (en) | 2010-12-21 |
| EP1630165B1 (fr) | 2010-03-31 |
| JP4698419B2 (ja) | 2011-06-08 |
| US20070010515A1 (en) | 2007-01-11 |
| KR20060026033A (ko) | 2006-03-22 |
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