ZA200605587B - Novel phenylalanine derivative - Google Patents
Novel phenylalanine derivative Download PDFInfo
- Publication number
- ZA200605587B ZA200605587B ZA200605587A ZA200605587A ZA200605587B ZA 200605587 B ZA200605587 B ZA 200605587B ZA 200605587 A ZA200605587 A ZA 200605587A ZA 200605587 A ZA200605587 A ZA 200605587A ZA 200605587 B ZA200605587 B ZA 200605587B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- pharmaceutically acceptable
- acceptable salts
- carbon atoms
- hydrogen atom
- Prior art date
Links
- 150000002993 phenylalanine derivatives Chemical class 0.000 title claims description 85
- -1 morpholinoethyloxy group Chemical group 0.000 claims description 128
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 115
- 125000004432 carbon atom Chemical group C* 0.000 claims description 94
- 239000000460 chlorine Substances 0.000 claims description 92
- 150000003839 salts Chemical class 0.000 claims description 85
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
- 229910052731 fluorine Inorganic materials 0.000 claims description 60
- 229910052801 chlorine Inorganic materials 0.000 claims description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 34
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 27
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical group C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 239000003814 drug Substances 0.000 claims description 15
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 13
- 229940124597 therapeutic agent Drugs 0.000 claims description 13
- 230000003449 preventive effect Effects 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 10
- 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 description 10
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 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 9
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
- 208000026935 allergic disease Diseases 0.000 claims description 7
- 230000007170 pathology Effects 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 230000007815 allergy Effects 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 230000009401 metastasis Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
- 229940123038 Integrin antagonist Drugs 0.000 claims description 4
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 230000035755 proliferation Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 3
- 101100495911 Arabidopsis thaliana CHR10 gene Proteins 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- QPILHXCDZYWYLQ-UHFFFAOYSA-N 2-nonyl-1,3-dioxolane Chemical compound CCCCCCCCCC1OCCO1 QPILHXCDZYWYLQ-UHFFFAOYSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- 241000272522 Anas Species 0.000 claims 1
- 241001442234 Cosa Species 0.000 claims 1
- 101000851593 Homo sapiens Separin Proteins 0.000 claims 1
- 241000532353 Porzana Species 0.000 claims 1
- 241000568452 Sania Species 0.000 claims 1
- 102100036750 Separin Human genes 0.000 claims 1
- 230000005021 gait Effects 0.000 claims 1
- 108010044426 integrins Proteins 0.000 description 24
- 102000006495 integrins Human genes 0.000 description 24
- 108010008212 Integrin alpha4beta1 Proteins 0.000 description 20
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 20
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- 201000010099 disease Diseases 0.000 description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 210000001519 tissue Anatomy 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 210000000265 leukocyte Anatomy 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 8
- 230000010062 adhesion mechanism Effects 0.000 description 8
- 210000004698 lymphocyte Anatomy 0.000 description 8
- 230000003042 antagnostic effect Effects 0.000 description 7
- 210000004204 blood vessel Anatomy 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 108010067306 Fibronectins Proteins 0.000 description 6
- 102000016359 Fibronectins Human genes 0.000 description 6
- 206010046851 Uveitis Diseases 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 210000003989 endothelium vascular Anatomy 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 5
- 206010009900 Colitis ulcerative Diseases 0.000 description 5
- 208000011231 Crohn disease Diseases 0.000 description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 description 5
- 208000026106 cerebrovascular disease Diseases 0.000 description 5
- 102100028793 Mucosal addressin cell adhesion molecule 1 Human genes 0.000 description 4
- 101710139349 Mucosal addressin cell adhesion molecule 1 Proteins 0.000 description 4
- 102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 4
- 208000006454 hepatitis Diseases 0.000 description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 description 4
- 230000008595 infiltration Effects 0.000 description 4
- 238000001764 infiltration Methods 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 210000001986 peyer's patch Anatomy 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 206010003827 Autoimmune hepatitis Diseases 0.000 description 3
- 206010008609 Cholangitis sclerosing Diseases 0.000 description 3
- 206010008909 Chronic Hepatitis Diseases 0.000 description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- 206010015084 Episcleritis Diseases 0.000 description 3
- 206010015226 Erythema nodosum Diseases 0.000 description 3
- 208000007465 Giant cell arteritis Diseases 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 3
- 206010039705 Scleritis Diseases 0.000 description 3
- 201000009594 Systemic Scleroderma Diseases 0.000 description 3
- 206010042953 Systemic sclerosis Diseases 0.000 description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 206010008118 cerebral infarction Diseases 0.000 description 3
- 208000019425 cirrhosis of liver Diseases 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 210000002744 extracellular matrix Anatomy 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 201000004614 iritis Diseases 0.000 description 3
- 230000000302 ischemic effect Effects 0.000 description 3
- 201000010260 leiomyoma Diseases 0.000 description 3
- 210000003563 lymphoid tissue Anatomy 0.000 description 3
- 201000008482 osteoarthritis Diseases 0.000 description 3
- 229960005190 phenylalanine Drugs 0.000 description 3
- 235000008729 phenylalanine Nutrition 0.000 description 3
- 201000011461 pre-eclampsia Diseases 0.000 description 3
- 201000000742 primary sclerosing cholangitis Diseases 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- 201000000306 sarcoidosis Diseases 0.000 description 3
- 208000010157 sclerosing cholangitis Diseases 0.000 description 3
- 208000020431 spinal cord injury Diseases 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 206010043207 temporal arteritis Diseases 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 230000009529 traumatic brain injury Effects 0.000 description 3
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101710178046 Chorismate synthase 1 Proteins 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 101710152695 Cysteine synthase 1 Proteins 0.000 description 2
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 2
- 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 2
- 208000005176 Hepatitis C Diseases 0.000 description 2
- 102100032831 Protein ITPRID2 Human genes 0.000 description 2
- 206010039361 Sacroiliitis Diseases 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000000427 antigen Substances 0.000 description 2
- 102000036639 antigens Human genes 0.000 description 2
- 108091007433 antigens Proteins 0.000 description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 101150113676 chr1 gene Proteins 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 210000004153 islets of langerhan Anatomy 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000010172 mouse model Methods 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 208000009954 pyoderma gangrenosum Diseases 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- KZMAWJRXKGLWGS-UHFFFAOYSA-N 2-chloro-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-n-(3-methoxypropyl)acetamide Chemical compound S1C(N(C(=O)CCl)CCCOC)=NC(C=2C=CC(OC)=CC=2)=C1 KZMAWJRXKGLWGS-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 101100495912 Arabidopsis thaliana CHR12 gene Proteins 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- 235000011960 Brassica ruvo Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 102000019034 Chemokines Human genes 0.000 description 1
- 108010012236 Chemokines Proteins 0.000 description 1
- 108090001069 Chymopapain Proteins 0.000 description 1
- CHBRHODLKOZEPZ-UHFFFAOYSA-N Clotiazepam Chemical compound S1C(CC)=CC2=C1N(C)C(=O)CN=C2C1=CC=CC=C1Cl CHBRHODLKOZEPZ-UHFFFAOYSA-N 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 108010024212 E-Selectin Proteins 0.000 description 1
- 102100023471 E-selectin Human genes 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 101000635799 Homo sapiens Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Proteins 0.000 description 1
- 102100025323 Integrin alpha-1 Human genes 0.000 description 1
- 102100032816 Integrin alpha-6 Human genes 0.000 description 1
- 108010041341 Integrin alpha1 Proteins 0.000 description 1
- 108010055795 Integrin alpha1beta1 Proteins 0.000 description 1
- 108010041100 Integrin alpha6 Proteins 0.000 description 1
- 108010030465 Integrin alpha6beta1 Proteins 0.000 description 1
- 108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 description 1
- 102100037877 Intercellular adhesion molecule 1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- 108010085895 Laminin Proteins 0.000 description 1
- 102000007547 Laminin Human genes 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 102000004264 Osteopontin Human genes 0.000 description 1
- 108010081689 Osteopontin Proteins 0.000 description 1
- 241001504519 Papio ursinus Species 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 208000006311 Pyoderma Diseases 0.000 description 1
- 241000219061 Rheum Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 102000007000 Tenascin Human genes 0.000 description 1
- 108010008125 Tenascin Proteins 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102100040247 Tumor necrosis factor Human genes 0.000 description 1
- 108010031318 Vitronectin Proteins 0.000 description 1
- 102100035140 Vitronectin Human genes 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005784 autoimmunity Effects 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000004410 cyclooctyloxy group Chemical group C1(CCCCCCC1)O* 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 210000003979 eosinophil Anatomy 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 208000012997 experimental autoimmune encephalomyelitis Diseases 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000001926 lymphatic effect Effects 0.000 description 1
- 210000001365 lymphatic vessel Anatomy 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 210000001258 synovial membrane Anatomy 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000000264 venule Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or 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
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- 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
-
- 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
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Transplantation (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003425347 | 2003-12-22 | ||
| JP2004074943 | 2004-03-16 | ||
| JP2004159919 | 2004-05-28 | ||
| JP2004260319 | 2004-09-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200605587B true ZA200605587B (en) | 2008-02-27 |
Family
ID=34714482
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200605587A ZA200605587B (en) | 2003-12-22 | 2004-12-22 | Novel phenylalanine derivative |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7345049B2 (pt) |
| EP (3) | EP2803667A1 (pt) |
| JP (1) | JP4743659B2 (pt) |
| KR (2) | KR20110098980A (pt) |
| CN (2) | CN1917881B (pt) |
| AU (1) | AU2004303696B2 (pt) |
| BR (1) | BRPI0418026A (pt) |
| CA (1) | CA2550843C (pt) |
| ES (1) | ES2548853T3 (pt) |
| IL (1) | IL176469A (pt) |
| NO (1) | NO337628B1 (pt) |
| NZ (1) | NZ548420A (pt) |
| RU (1) | RU2390520C2 (pt) |
| WO (1) | WO2005061466A1 (pt) |
| ZA (1) | ZA200605587B (pt) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL223152B1 (pl) | 2000-08-18 | 2016-10-31 | Ajinomoto Kk | Pochodne fenyloalaniny, kompozycja farmaceutyczna oraz zastosowanie tych pochodnych |
| EP1323711B1 (en) * | 2000-09-29 | 2006-11-15 | Ajinomoto Co., Inc. | Novel phenylalanine derivatives |
| EP1477482B1 (en) * | 2002-02-20 | 2010-04-14 | Ajinomoto Co., Inc. | Novel phenylalanine derivative |
| CN101386600B (zh) * | 2003-02-20 | 2011-07-06 | 味之素株式会社 | 具有喹唑二酮骨架的苯丙氨酸衍生物的制造方法及制造中间体 |
| DE602004031144D1 (de) * | 2003-11-14 | 2011-03-03 | Ajinomoto Kk | Feste dispersion oder medizinisches festes dispersionspräparat eines phenylalanin-derivats |
| JP4947482B2 (ja) * | 2003-11-14 | 2012-06-06 | 味の素株式会社 | フェニルアラニン誘導体の徐放性経口投与製剤 |
| KR101123606B1 (ko) * | 2003-11-27 | 2012-03-20 | 아지노모토 가부시키가이샤 | 페닐알라닌 유도체의 결정 및 이의 제조방법 |
| EP2803667A1 (en) * | 2003-12-22 | 2014-11-19 | Ajinomoto Co., Inc. | Phenylalanine derivatives |
| JP5046188B2 (ja) * | 2005-06-21 | 2012-10-10 | 味の素株式会社 | フェニルアラニン誘導体の結晶、その製造方法及びその使用 |
| WO2007028789A1 (en) * | 2005-09-07 | 2007-03-15 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | Quinazoline derivatives as antiviral agents |
| US20090111828A1 (en) * | 2005-11-23 | 2009-04-30 | Astrazeneca Ab | L-alanine derivatives |
| AU2006337137B2 (en) * | 2005-12-29 | 2012-06-14 | Tersera Therapeutics Llc | Multicyclic amino acid derivatives and methods of their use |
| US7834050B2 (en) * | 2006-03-29 | 2010-11-16 | Duke University | Small molecule insulin mimetics absent quinones |
| EP2049490A1 (en) * | 2006-06-09 | 2009-04-22 | Astra Zeneca AB | N-(benzoyl)-o- [2- (pyridin- 2 -ylamino) ethyl]-l-tyrosine derivatives and related compounds as a5b1 antagonists for the treatment of solid tumors |
| RU2469028C2 (ru) | 2006-11-22 | 2012-12-10 | Адзиномото Ко., Инк. | Способ получения производных фенилаланина с хиназолиндионовым скелетом и промежуточных соединений, применяемых при получении таких производных |
| US20090062267A1 (en) * | 2007-01-29 | 2009-03-05 | Astrazeneca Ab | L-ALANINE DERIVATIVES AS a5beta1 ANTAGONISTS |
| WO2008125811A1 (en) * | 2007-04-11 | 2008-10-23 | Astrazeneca Ab | N-[HETEROARYLCARBONYL]-S-THIENYL-L-ALANINE DERIVATIVES AS α5β1 ANTAGONISTS |
| TW200911755A (en) * | 2007-04-19 | 2009-03-16 | Astellas Pharma Inc | Bicyclic heterocyclic compounds |
| WO2011094890A1 (en) * | 2010-02-02 | 2011-08-11 | Argusina Inc. | Phenylalanine derivatives and their use as non-peptide glp-1 receptor modulators |
| JP6109568B2 (ja) | 2010-03-29 | 2017-04-05 | Ｅａファーマ株式会社 | フェニルアラニン誘導体の塩の結晶 |
| US8501982B2 (en) | 2010-06-09 | 2013-08-06 | Receptos, Inc. | GLP-1 receptor stabilizers and modulators |
| PT2713722T (pt) | 2011-05-31 | 2017-06-27 | Receptos Llc | Novos estabilizadores e moduladores do receptor glp-1 |
| JP6061949B2 (ja) * | 2011-12-12 | 2017-01-18 | レセプトス エルエルシー | 糖尿病などの疾患の治療のためのｇｌｐ−１受容体モジュレーターとして作用する４つの環を含むカルボン酸誘導体 |
| CN104395297B (zh) * | 2012-04-24 | 2016-05-04 | 味之素株式会社 | 磺酰胺衍生物及其药物用途 |
| CN102993105B (zh) * | 2012-12-19 | 2014-06-11 | 西南大学 | 1-甲基-2,4-喹唑啉二酮衍生物及其制备方法和应用 |
| MX370666B (es) * | 2013-06-11 | 2019-12-19 | Celgene Int Ii Sarl | Novedosos moduladores del receptor de péptido tipo glucagón 1 (glp-1). |
| CA2928619C (en) * | 2013-10-29 | 2019-04-02 | Ajinomoto Co., Inc. | Sulfonamide derivative and pharmaceutical use thereof |
| EA032525B1 (ru) | 2014-07-25 | 2019-06-28 | Селджин Интернэшнл Ii Сарл | Модуляторы рецептора glp-1 |
| EP3230276B1 (en) | 2014-12-10 | 2020-09-02 | Celgene International II Sarl | Glp-1 receptor modulators |
| AU2016344115A1 (en) | 2015-10-27 | 2018-05-10 | Merck Sharp & Dohme Corp. | Substituted indazole compounds as rorgammat inhibitors and uses thereof |
| CA3013433A1 (en) | 2016-02-05 | 2017-08-10 | Ea Pharma Co., Ltd. | Sulfonamide derivative and pharmaceutical composition containing same |
| AU2019373245C1 (en) | 2018-10-30 | 2022-10-27 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4β7 integrin |
| EP3873900A1 (en) | 2018-10-30 | 2021-09-08 | Gilead Sciences, Inc. | Imidazopyridine derivatives as alpha4beta7 integrin inhibitors |
| WO2020092383A1 (en) | 2018-10-30 | 2020-05-07 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
| CN112969687B (zh) | 2018-10-30 | 2024-08-23 | 吉利德科学公司 | 作为α4β7整合素抑制剂的喹啉衍生物 |
| WO2021030438A1 (en) | 2019-08-14 | 2021-02-18 | Gilead Sciences, Inc. | Compounds for inhibition of alpha 4 beta 7 integrin |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4111394A1 (de) | 1991-04-09 | 1992-10-15 | Behringwerke Ag | Amidinophenylalaninderivate, verfahren zu deren herstellung, deren verwendung und diese enthaltende mittel |
| ES2102009T5 (es) | 1992-01-13 | 2004-12-16 | Biogen Inc | Tratamiento para el asma. |
| DK0625912T3 (da) | 1992-02-12 | 1997-10-27 | Biogen Inc | Behandling af inflammatorisk tarmsygdom |
| SG52262A1 (en) | 1993-01-08 | 1998-09-28 | Tanabe Seiyaku Co | Peptide inhibitors of cell adhesion |
| EP0678122B1 (en) | 1993-01-12 | 1999-07-28 | Biogen, Inc. | Recombinant anti-vla4 antibody molecules |
| AU693143B2 (en) | 1993-12-06 | 1998-06-25 | Cytel Corporation | CS-1 peptidomimetics, compositions and methods of using the same |
| CN1211123C (zh) | 1994-01-25 | 2005-07-20 | 雅典娜神经科学公司 | 抗白细胞粘附分子vla－4的人源化抗体 |
| AU2958195A (en) | 1994-06-29 | 1996-01-25 | Texas Biotechnology Corporation | Process to inhibit binding of the integrin alpha 4 beta 1 to vcam-1 or fibronectin |
| US5811391A (en) | 1994-08-25 | 1998-09-22 | Cytel Corporation | Cyclic CS-1 peptidomimetics, compositions and methods of using same |
| DE19650975A1 (de) * | 1996-12-09 | 1998-06-10 | Basf Ag | Neue heterocyclisch substituierte Benzamide und deren Anwendung |
| ID22711A (id) | 1997-02-28 | 1999-12-09 | Pfizer Prod Inc | Atropisomer dari 3-aril-4(3h)-kinazolinon dan penggunaannya sebagai antagonis reseptor-ampa |
| AR013384A1 (es) | 1997-07-31 | 2000-12-27 | Athena Neurosciences Inc | Compuestos del tipo de fenilalanina substituidos que inhiben la adhesion de leucocitos intermediada por vla-4 |
| DE69821950T2 (de) | 1997-08-22 | 2004-12-16 | F. Hoffmann-La Roche Ag | N-aroylphenylalaninderivate |
| PL193283B1 (pl) | 1997-08-22 | 2007-01-31 | Hoffmann La Roche | Nowe pochodne N-aroilofenyloalaniny, ich zastosowanie i środek leczniczy |
| US6197794B1 (en) | 1998-01-08 | 2001-03-06 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| MY153569A (en) | 1998-01-20 | 2015-02-27 | Mitsubishi Tanabe Pharma Corp | Inhibitors of ?4 mediated cell adhesion |
| US6329372B1 (en) | 1998-01-27 | 2001-12-11 | Celltech Therapeutics Limited | Phenylalanine derivatives |
| ES2226413T3 (es) | 1998-02-26 | 2005-03-16 | Celltech Therapeutics Limited | Derivados de fenilalanina como inhibidores de alfa-4 integrinas. |
| DE19818614A1 (de) * | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Amide, deren Herstellung und Anwendung |
| DE19817461A1 (de) * | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Benzamide, deren Herstellung und Anwendung |
| US6171578B1 (en) * | 1999-04-14 | 2001-01-09 | Diatide, Inc. | Benzodiazepine derivatives for imaging thrombi |
| JP3795305B2 (ja) | 1999-07-19 | 2006-07-12 | 田辺製薬株式会社 | 医薬組成物 |
| GB2354440A (en) | 1999-07-20 | 2001-03-28 | Merck & Co Inc | Aryl amides as cell adhesion inhibitors |
| AU1416501A (en) | 1999-11-18 | 2001-05-30 | Ajinomoto Co., Inc. | Novel phenylalanine derivatives |
| CN1218943C (zh) | 1999-12-06 | 2005-09-14 | 霍夫曼-拉罗奇有限公司 | 4－嘧啶基－n－酰基－l－苯基丙氨酸类化合物 |
| PT1244625E (pt) | 1999-12-06 | 2005-09-30 | Hoffmann La Roche | 4-piridinil-n-acil-l-fenilalaninas |
| EP1243577A4 (en) | 1999-12-28 | 2005-06-08 | Ajinomoto Kk | NEW PHENYLALANINE DERIVATIVES |
| AU2001242743A1 (en) | 2000-03-23 | 2001-10-03 | Ajinomoto Co. Inc. | Novel phenylalanine derivative |
| US6960597B2 (en) | 2000-06-30 | 2005-11-01 | Orth-Mcneil Pharmaceutical, Inc. | Aza-bridged-bicyclic amino acid derivatives as α4 integrin antagonists |
| PL223152B1 (pl) * | 2000-08-18 | 2016-10-31 | Ajinomoto Kk | Pochodne fenyloalaniny, kompozycja farmaceutyczna oraz zastosowanie tych pochodnych |
| MY129000A (en) * | 2000-08-31 | 2007-03-30 | Tanabe Seiyaku Co | INHIBITORS OF a4 MEDIATED CELL ADHESION |
| EP1323711B1 (en) | 2000-09-29 | 2006-11-15 | Ajinomoto Co., Inc. | Novel phenylalanine derivatives |
| JP4164871B2 (ja) * | 2001-07-26 | 2008-10-15 | 味の素株式会社 | 新規フェニルプロピオン酸誘導体 |
| WO2003053926A1 (fr) * | 2001-12-13 | 2003-07-03 | Ajinomoto Co.,Inc. | Nouveau derive de phenylalanine |
| EP1477482B1 (en) * | 2002-02-20 | 2010-04-14 | Ajinomoto Co., Inc. | Novel phenylalanine derivative |
| CN101386600B (zh) * | 2003-02-20 | 2011-07-06 | 味之素株式会社 | 具有喹唑二酮骨架的苯丙氨酸衍生物的制造方法及制造中间体 |
| JP2007507551A (ja) * | 2003-10-03 | 2007-03-29 | ポートラ ファーマシューティカルズ， インコーポレイテッド | ２，４−ジオキソ−３−キナゾリニルアリールスルホニル尿素 |
| KR101123606B1 (ko) * | 2003-11-27 | 2012-03-20 | 아지노모토 가부시키가이샤 | 페닐알라닌 유도체의 결정 및 이의 제조방법 |
| EP2803667A1 (en) * | 2003-12-22 | 2014-11-19 | Ajinomoto Co., Inc. | Phenylalanine derivatives |
| RU2469028C2 (ru) * | 2006-11-22 | 2012-12-10 | Адзиномото Ко., Инк. | Способ получения производных фенилаланина с хиназолиндионовым скелетом и промежуточных соединений, применяемых при получении таких производных |
-
2004
- 2004-12-22 EP EP14181015.0A patent/EP2803667A1/en not_active Withdrawn
- 2004-12-22 AU AU2004303696A patent/AU2004303696B2/en not_active Ceased
- 2004-12-22 RU RU2006126651/04A patent/RU2390520C2/ru not_active IP Right Cessation
- 2004-12-22 KR KR1020117019338A patent/KR20110098980A/ko not_active Application Discontinuation
- 2004-12-22 CN CN200480041967.9A patent/CN1917881B/zh not_active Expired - Fee Related
- 2004-12-22 US US11/018,226 patent/US7345049B2/en not_active Expired - Fee Related
- 2004-12-22 KR KR1020067014754A patent/KR101194176B1/ko active IP Right Grant
- 2004-12-22 CN CN201410016206.3A patent/CN103784458B/zh not_active Expired - Fee Related
- 2004-12-22 EP EP13152904.2A patent/EP2615087A3/en not_active Withdrawn
- 2004-12-22 NZ NZ548420A patent/NZ548420A/en not_active IP Right Cessation
- 2004-12-22 EP EP04808055.0A patent/EP1700850B1/en active Active
- 2004-12-22 BR BRPI0418026-7A patent/BRPI0418026A/pt not_active IP Right Cessation
- 2004-12-22 ES ES04808055.0T patent/ES2548853T3/es active Active
- 2004-12-22 JP JP2005516537A patent/JP4743659B2/ja not_active Expired - Fee Related
- 2004-12-22 CA CA2550843A patent/CA2550843C/en not_active Expired - Fee Related
- 2004-12-22 WO PCT/JP2004/019704 patent/WO2005061466A1/ja active Application Filing
- 2004-12-22 ZA ZA200605587A patent/ZA200605587B/en unknown
-
2006
- 2006-06-21 IL IL176469A patent/IL176469A/en active IP Right Grant
- 2006-07-20 NO NO20063372A patent/NO337628B1/no not_active IP Right Cessation
-
2007
- 2007-12-21 US US11/963,144 patent/US8309561B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200605587B (en) | Novel phenylalanine derivative | |
| AU2006212761B2 (en) | Combination therapy | |
| RU2437885C2 (ru) | Производные дигидропиразолопиримидинона | |
| CA2717948C (en) | 5imidazoquinolines and pyrimidine derivatives as potent modulators of vegf-driven angiogenic processes | |
| JP2002523502A5 (pt) | ||
| WO2000012497B1 (en) | Quinazoline derivatives as medicaments | |
| CN102399220A (zh) | 三并环类PI3K和mTOR双重抑制剂 | |
| JP2022524456A (ja) | Ｈｂｖ感染又はｈｂｖ誘導性疾患の治療における使用のための縮合環ピリミドン誘導体 | |
| KR20010012995A (ko) | 발기부전 치료제 | |
| TW200407122A (en) | Hemiasterlin derivatives and uses thereof | |
| EP0620224B1 (en) | Triazolopyridazine derivatives, their production and use | |
| CN106478631B (zh) | 长效二肽基肽酶-iv抑制剂、用途及其中间体的制备方法 | |
| CN102153553A (zh) | 含有氨基磺酰胺基氮杂环丁烷的口服碳青霉烯化合物 | |
| KR100280240B1 (ko) | 호산구 주화성 억제제 | |
| JPH07242544A (ja) | 抗腫瘍剤 | |
| AU2004270304A1 (en) | Guanidine derivatives | |
| EP1054669B1 (en) | Use of thiadiazolo[4,3-a]pyridine derivatives | |
| CN110272419A (zh) | 二氢吡啶并酞嗪酮衍生物、其制备方法及应用 | |
| JPH09323932A (ja) | エイズ治療剤又は予防剤 | |
| CN109438279A (zh) | 一种克服egfr耐药突变的小分子化合物及其制备方法和用途 | |
| WO2023109892A1 (zh) | 一种抑制或降解brd9的化合物及其组合物和药学上的应用 | |
| MXPA06007284A (en) | Novel phenylalanine derivative | |
| JP2869993B2 (ja) | ベンゾチエピノトリアゾロピリダジン誘導体 | |
| JPH11302175A (ja) | 抗ｈｃｍｖ剤 | |
| AU2012331125A1 (en) | 2-carboxamide cycloamino urea derivatives for use in treating VEGF - dependent diseases |