ZA200300883B - Compounds acting as melanocortin receptor ligands. - Google Patents
Compounds acting as melanocortin receptor ligands. Download PDFInfo
- Publication number
- ZA200300883B ZA200300883B ZA200300883A ZA200300883A ZA200300883B ZA 200300883 B ZA200300883 B ZA 200300883B ZA 200300883 A ZA200300883 A ZA 200300883A ZA 200300883 A ZA200300883 A ZA 200300883A ZA 200300883 B ZA200300883 B ZA 200300883B
- Authority
- ZA
- South Africa
- Prior art keywords
- guanidine
- compound
- indol
- prodrug
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 131
- 102000004378 Melanocortin Receptors Human genes 0.000 title claims abstract description 10
- 108090000950 Melanocortin Receptors Proteins 0.000 title claims abstract description 10
- 239000003446 ligand Substances 0.000 title abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 208000035475 disorder Diseases 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000002723 alicyclic group Chemical group 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 145
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 78
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 73
- -1 sulpho Chemical group 0.000 claims description 39
- 239000000651 prodrug Substances 0.000 claims description 37
- 229940002612 prodrug Drugs 0.000 claims description 37
- 206010061218 Inflammation Diseases 0.000 claims description 32
- 230000004054 inflammatory process Effects 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 27
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 230000001939 inductive effect Effects 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000004064 dysfunction Effects 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 7
- 208000014674 injury Diseases 0.000 claims description 7
- 208000028867 ischemia Diseases 0.000 claims description 6
- 201000001441 melanoma Diseases 0.000 claims description 6
- 230000036407 pain Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 150000002357 guanidines Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- 230000008929 regeneration Effects 0.000 claims description 5
- 238000011069 regeneration method Methods 0.000 claims description 5
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 5
- 150000001408 amides Chemical group 0.000 claims description 4
- 208000010668 atopic eczema Diseases 0.000 claims description 4
- 210000004369 blood Anatomy 0.000 claims description 4
- 239000008280 blood Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 206010061428 decreased appetite Diseases 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 210000005036 nerve Anatomy 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000036299 sexual function Effects 0.000 claims description 4
- 231100000167 toxic agent Toxicity 0.000 claims description 4
- 239000003440 toxic substance Substances 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 3
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 3
- 230000000172 allergic effect Effects 0.000 claims description 3
- 210000000748 cardiovascular system Anatomy 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 238000003745 diagnosis Methods 0.000 claims description 3
- 210000000750 endocrine system Anatomy 0.000 claims description 3
- 230000003054 hormonal effect Effects 0.000 claims description 3
- 238000001727 in vivo Methods 0.000 claims description 3
- 230000036210 malignancy Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000002285 radioactive effect Effects 0.000 claims description 3
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- 230000000578 anorexic effect Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 210000000578 peripheral nerve Anatomy 0.000 claims 2
- 230000010410 reperfusion Effects 0.000 claims 2
- NSXRDRAQAVMIAK-UHFFFAOYSA-N 2-[(5-bromo-2,3,4-trimethoxyphenyl)methyl]-1-[(3-chloro-4-fluorophenyl)methylideneamino]guanidine Chemical compound COC1=C(OC)C(OC)=C(Br)C=C1CNC(=N)NN=CC1=CC=C(F)C(Cl)=C1 NSXRDRAQAVMIAK-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108010008364 Melanocortins Proteins 0.000 abstract description 10
- 239000002865 melanocortin Substances 0.000 abstract description 10
- 201000010099 disease Diseases 0.000 description 26
- 210000003491 skin Anatomy 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000002757 inflammatory effect Effects 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- 210000003169 central nervous system Anatomy 0.000 description 7
- 230000000144 pharmacologic effect Effects 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000009885 systemic effect Effects 0.000 description 6
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 5
- 208000026935 allergic disease Diseases 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- 206010065159 Polychondritis Diseases 0.000 description 4
- 206010003230 arteritis Diseases 0.000 description 4
- 206010003246 arthritis Diseases 0.000 description 4
- 230000001363 autoimmune Effects 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 201000000306 sarcoidosis Diseases 0.000 description 4
- 230000001568 sexual effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- 102000000589 Interleukin-1 Human genes 0.000 description 3
- 108010002352 Interleukin-1 Proteins 0.000 description 3
- 102000004889 Interleukin-6 Human genes 0.000 description 3
- 108090001005 Interleukin-6 Proteins 0.000 description 3
- 206010067125 Liver injury Diseases 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 201000009594 Systemic Scleroderma Diseases 0.000 description 3
- 206010042953 Systemic sclerosis Diseases 0.000 description 3
- 102000008316 Type 4 Melanocortin Receptor Human genes 0.000 description 3
- 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 description 3
- 208000036142 Viral infection Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000001270 agonistic effect Effects 0.000 description 3
- 230000007815 allergy Effects 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 206010009887 colitis Diseases 0.000 description 3
- 210000004907 gland Anatomy 0.000 description 3
- 231100000234 hepatic damage Toxicity 0.000 description 3
- 208000006454 hepatitis Diseases 0.000 description 3
- 231100000283 hepatitis Toxicity 0.000 description 3
- 208000027866 inflammatory disease Diseases 0.000 description 3
- 229940100601 interleukin-6 Drugs 0.000 description 3
- 230000008818 liver damage Effects 0.000 description 3
- 230000003211 malignant effect Effects 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 230000032696 parturition Effects 0.000 description 3
- 208000008494 pericarditis Diseases 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 230000012495 positive regulation of renal sodium excretion Effects 0.000 description 3
- 208000002574 reactive arthritis Diseases 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- SAWHDJTZESXNMM-UHFFFAOYSA-N 2-chloro-3,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(Cl)=C1OC SAWHDJTZESXNMM-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical compound NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 201000010000 Agranulocytosis Diseases 0.000 description 2
- 206010001889 Alveolitis Diseases 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- 206010003267 Arthritis reactive Diseases 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 102100021752 Corticoliberin Human genes 0.000 description 2
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 208000007882 Gastritis Diseases 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 0.000 description 2
- 206010018687 Granulocytopenia Diseases 0.000 description 2
- 206010018691 Granuloma Diseases 0.000 description 2
- 206010061216 Infarction Diseases 0.000 description 2
- 208000011200 Kawasaki disease Diseases 0.000 description 2
- 102000016267 Leptin Human genes 0.000 description 2
- 108010092277 Leptin Proteins 0.000 description 2
- 102000030612 Melanocortin 5 receptor Human genes 0.000 description 2
- 108010088565 Melanocortin 5 receptor Proteins 0.000 description 2
- 102100023726 Melanocortin receptor 3 Human genes 0.000 description 2
- 101710151321 Melanostatin Proteins 0.000 description 2
- 208000003250 Mixed connective tissue disease Diseases 0.000 description 2
- 208000009525 Myocarditis Diseases 0.000 description 2
- 102400000064 Neuropeptide Y Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 102000003946 Prolactin Human genes 0.000 description 2
- 108010057464 Prolactin Proteins 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 2
- 206010039705 Scleritis Diseases 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 206010042496 Sunburn Diseases 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 102000008318 Type 3 Melanocortin Receptor Human genes 0.000 description 2
- 108010021433 Type 3 Melanocortin Receptor Proteins 0.000 description 2
- 206010047115 Vasculitis Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 206010000210 abortion Diseases 0.000 description 2
- 231100000176 abortion Toxicity 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 208000003455 anaphylaxis Diseases 0.000 description 2
- 208000022531 anorexia Diseases 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 206010014665 endocarditis Diseases 0.000 description 2
- 210000002889 endothelial cell Anatomy 0.000 description 2
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000009610 hypersensitivity Effects 0.000 description 2
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 description 2
- 210000000987 immune system Anatomy 0.000 description 2
- 230000003308 immunostimulating effect Effects 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 230000007574 infarction Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- 229940039781 leptin Drugs 0.000 description 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000008099 melanin synthesis Effects 0.000 description 2
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229940097325 prolactin Drugs 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000006442 vascular tone Effects 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical class C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 description 1
- GFVLAEHYJASGKP-UHFFFAOYSA-N 1-[(2,4-dinitrophenyl)methylideneamino]-2-phenylguanidine Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1C=NNC(=N)NC1=CC=CC=C1 GFVLAEHYJASGKP-UHFFFAOYSA-N 0.000 description 1
- SMXJSTNXPBXBOR-UHFFFAOYSA-N 1-amino-2-benzylguanidine Chemical compound NNC(N)=NCC1=CC=CC=C1 SMXJSTNXPBXBOR-UHFFFAOYSA-N 0.000 description 1
- GYUVRSXWOUXRDP-UHFFFAOYSA-N 2-anilino-1-hydroxyguanidine;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.ONC(N)=NNC1=CC=CC=C1 GYUVRSXWOUXRDP-UHFFFAOYSA-N 0.000 description 1
- XWXWWMABCFPCLY-UHFFFAOYSA-N 2-benzyl-1-[(2-chloro-3,4-dimethoxyphenyl)methylideneamino]guanidine Chemical compound ClC1=C(OC)C(OC)=CC=C1C=NNC(=N)NCC1=CC=CC=C1 XWXWWMABCFPCLY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000032467 Aplastic anaemia Diseases 0.000 description 1
- 208000004300 Atrophic Gastritis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010050245 Autoimmune thrombocytopenia Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
- 206010004659 Biliary cirrhosis Diseases 0.000 description 1
- 206010048962 Brain oedema Diseases 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 208000032841 Bulimia Diseases 0.000 description 1
- 206010006550 Bulimia nervosa Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 208000002691 Choroiditis Diseases 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 208000000668 Chronic Pancreatitis Diseases 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 description 1
- 108010091893 Cosyntropin Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 102000016607 Diphtheria Toxin Human genes 0.000 description 1
- 108010053187 Diphtheria Toxin Proteins 0.000 description 1
- 208000006926 Discoid Lupus Erythematosus Diseases 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- 206010013700 Drug hypersensitivity Diseases 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 201000009273 Endometriosis Diseases 0.000 description 1
- 206010015084 Episcleritis Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 208000004248 Familial Primary Pulmonary Hypertension Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 description 1
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 208000036495 Gastritis atrophic Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 206010019755 Hepatitis chronic active Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 206010022941 Iridocyclitis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010069698 Langerhans' cell histiocytosis Diseases 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 102000009151 Luteinizing Hormone Human genes 0.000 description 1
- 108010073521 Luteinizing Hormone Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 1
- 108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 description 1
- 102000012539 Melanocyte-stimulating hormone receptors Human genes 0.000 description 1
- 108050002130 Melanocyte-stimulating hormone receptors Proteins 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- 102000011779 Nitric Oxide Synthase Type II Human genes 0.000 description 1
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 206010030216 Oesophagitis Diseases 0.000 description 1
- 241001420836 Ophthalmitis Species 0.000 description 1
- 208000003435 Optic Neuritis Diseases 0.000 description 1
- 102000002512 Orexin Human genes 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 206010033647 Pancreatitis acute Diseases 0.000 description 1
- 206010033649 Pancreatitis chronic Diseases 0.000 description 1
- 208000007048 Polymyalgia Rheumatica Diseases 0.000 description 1
- 208000003971 Posterior uveitis Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 206010037601 Pyelonephritis chronic Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000033464 Reiter syndrome Diseases 0.000 description 1
- 201000001949 Retinal Vasculitis Diseases 0.000 description 1
- 108010039491 Ricin Proteins 0.000 description 1
- 206010039792 Seborrhoea Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 102100038803 Somatotropin Human genes 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 108700012920 TNF Proteins 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 1
- 206010048302 Tubulointerstitial nephritis Diseases 0.000 description 1
- 102100040247 Tumor necrosis factor Human genes 0.000 description 1
- 102000008314 Type 1 Melanocortin Receptor Human genes 0.000 description 1
- 108010021428 Type 1 Melanocortin Receptor Proteins 0.000 description 1
- 206010046788 Uterine haemorrhage Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010047642 Vitiligo Diseases 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 201000003229 acute pancreatitis Diseases 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 238000003975 animal breeding Methods 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 201000004612 anterior uveitis Diseases 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 230000008344 brain blood flow Effects 0.000 description 1
- 208000006752 brain edema Diseases 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 208000010353 central nervous system vasculitis Diseases 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 208000016644 chronic atrophic gastritis Diseases 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 201000006368 chronic pyelonephritis Diseases 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 208000019000 darkening of skin Diseases 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 230000020595 eating behavior Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 230000002327 eosinophilic effect Effects 0.000 description 1
- 208000003401 eosinophilic granuloma Diseases 0.000 description 1
- 210000001339 epidermal cell Anatomy 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 230000001257 erectogenic effect Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 210000003499 exocrine gland Anatomy 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 210000001145 finger joint Anatomy 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 229940028334 follicle stimulating hormone Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 244000000013 helminth Species 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001146 hypoxic effect Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 229940099472 immunoglobulin a Drugs 0.000 description 1
- 201000001881 impotence Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 238000000185 intracerebroventricular administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 210000002510 keratinocyte Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940080435 lactose 250 mg Drugs 0.000 description 1
- 230000013016 learning Effects 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229940040129 luteinizing hormone Drugs 0.000 description 1
- 210000003563 lymphoid tissue Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000336 melanocortin receptor agonist Substances 0.000 description 1
- 210000002752 melanocyte Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000015654 memory Effects 0.000 description 1
- 208000007106 menorrhagia Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 230000008450 motivation Effects 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 108060005714 orexin Proteins 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 206010033072 otitis externa Diseases 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 230000037324 pain perception Effects 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000010403 panophthalmitis Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 210000004694 pigment cell Anatomy 0.000 description 1
- 230000028742 placenta development Effects 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 201000008312 primary pulmonary hypertension Diseases 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 208000009954 pyoderma gangrenosum Diseases 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- 230000009329 sexual behaviour Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 108091006106 transcriptional activators Proteins 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 230000001228 trophic effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Indole Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0019359.9A GB0019359D0 (en) | 2000-08-07 | 2000-08-07 | Novel guanidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200300883B true ZA200300883B (en) | 2004-02-19 |
Family
ID=9897136
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200300883A ZA200300883B (en) | 2000-08-07 | 2003-01-31 | Compounds acting as melanocortin receptor ligands. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7153881B2 (enExample) |
| EP (1) | EP1309544B1 (enExample) |
| JP (1) | JP4891516B2 (enExample) |
| KR (1) | KR100911888B1 (enExample) |
| AT (1) | ATE413382T1 (enExample) |
| AU (1) | AU2001276539A1 (enExample) |
| BR (1) | BR0113064A (enExample) |
| CA (1) | CA2417904C (enExample) |
| DE (1) | DE60136468D1 (enExample) |
| DK (1) | DK1309544T3 (enExample) |
| ES (1) | ES2316460T3 (enExample) |
| GB (1) | GB0019359D0 (enExample) |
| IL (1) | IL154271A0 (enExample) |
| MX (1) | MXPA03001073A (enExample) |
| WO (1) | WO2002012178A1 (enExample) |
| ZA (1) | ZA200300883B (enExample) |
Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0019357D0 (en) * | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel phenyl guanidines |
| GB0019359D0 (en) | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel guanidines |
| GB0108631D0 (en) * | 2001-04-05 | 2001-05-30 | Melacure Therapeutics Ab | Novel benzylideneamino guanidines and their uses as ligands to the melanocortin receptors |
| GB0119172D0 (en) * | 2001-08-06 | 2001-09-26 | Melacure Therapeutics Ab | Phenyl pyrrole derivatives |
| US7456184B2 (en) | 2003-05-01 | 2008-11-25 | Palatin Technologies Inc. | Melanocortin receptor-specific compounds |
| EP1425029A4 (en) | 2001-08-10 | 2006-06-07 | Palatin Technologies Inc | PEPTIDOMIMETICS OF BIOLOGICALLY ACTIVE METALLOPEPTIDES |
| JP2005524649A (ja) * | 2002-02-25 | 2005-08-18 | カイロン コーポレーション | Ｍｃ４−ｒアゴニストの鼻腔内投与 |
| US6951881B2 (en) * | 2002-05-10 | 2005-10-04 | Wyeth | (1-substituted-indol-3-yl) alkylidenehydrazinecarboximidamide derivatives as 5-hydroxytryptamine-6 ligands |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7547693B2 (en) | 2003-09-22 | 2009-06-16 | Banyu Pharmaceutical Co. Ltd. | Piperidine derivative |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| US7737155B2 (en) | 2005-05-17 | 2010-06-15 | Schering Corporation | Nitrogen-containing heterocyclic compounds and methods of use thereof |
| EP1892241B1 (en) | 2005-05-30 | 2016-03-30 | Msd K.K. | Novel piperidine derivative |
| EP1916239A4 (en) | 2005-08-10 | 2009-10-21 | Banyu Pharma Co Ltd | PYRIDOLVERBINDUNG |
| JPWO2007024004A1 (ja) | 2005-08-24 | 2009-03-05 | 萬有製薬株式会社 | フェニルピリドン誘導体 |
| EP1939194A4 (en) | 2005-09-07 | 2010-12-08 | Banyu Pharma Co Ltd | BICYCLIC AROMATIC SUBSTITUTED PYRIDONE DERIVATIVE |
| KR20080048502A (ko) | 2005-09-29 | 2008-06-02 | 머크 앤드 캄파니 인코포레이티드 | 멜라노코르틴-4 수용체 조절제로서의 아실화스피로피페리딘 유도체 |
| AU2006304836A1 (en) | 2005-10-21 | 2007-04-26 | Novartis Ag | Combination of a renin-inhibitor and an anti-dyslipidemic agent and/or an antiobesity agent |
| JPWO2007049798A1 (ja) | 2005-10-27 | 2009-04-30 | 萬有製薬株式会社 | 新規ベンゾオキサチイン誘導体 |
| NZ568292A (en) | 2005-11-10 | 2011-08-26 | Msd Kk | Spiro[cyclohexane-1,1'-(3'H)-4'-azaisobenzofuran]-4-carboxamide derivatives |
| WO2007141343A1 (en) | 2006-06-09 | 2007-12-13 | Action Pharma A/S | Phenyl pyrrole aminoguanidine derivatives |
| AU2007300627B2 (en) | 2006-09-22 | 2012-02-16 | Merck Sharp & Dohme Corp. | Method of treatment using fatty acid synthesis inhibitors |
| EP2072519A4 (en) | 2006-09-28 | 2009-10-21 | Banyu Pharma Co Ltd | DIARYLKETIMINDERIVAT |
| GB0624987D0 (en) * | 2006-12-14 | 2007-01-24 | Acure Pharma Ab | Novel aminoguanidines as melanocortin receptor ligands |
| JP5319518B2 (ja) | 2007-04-02 | 2013-10-16 | Ｍｓｄ株式会社 | インドールジオン誘導体 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| JP5546451B2 (ja) | 2007-06-04 | 2014-07-09 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸の障害、炎症、癌および他の障害の処置に有用なグアニル酸シクラーゼのアゴニスト |
| CN103450077B (zh) | 2007-06-08 | 2016-07-06 | 满康德股份有限公司 | IRE-1α抑制剂 |
| WO2009071101A1 (en) * | 2007-12-07 | 2009-06-11 | Action Pharma A/S | N-modified aminoguanidine derivatives |
| WO2009074157A1 (en) * | 2007-12-13 | 2009-06-18 | Action Pharma A/S | Fully-modified phenyl pyrrole aminoguanidines |
| WO2009111037A2 (en) * | 2008-03-04 | 2009-09-11 | Indigene Pharmaceuticals Inc. | Compositions and methods for treating nos-associated diseases |
| AU2009220605A1 (en) | 2008-03-06 | 2009-09-11 | Msd K.K. | Alkylaminopyridine derivative |
| CN101981025A (zh) | 2008-03-28 | 2011-02-23 | 万有制药株式会社 | 具有黑色素浓缩激素受体拮抗作用的二芳基甲基酰胺衍生物 |
| AU2009261248A1 (en) | 2008-06-19 | 2009-12-23 | Banyu Pharmaceutical Co., Ltd. | Spirodiamine-diarylketoxime derivative |
| EP3241839B1 (en) | 2008-07-16 | 2019-09-04 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| US20110124674A1 (en) | 2008-07-30 | 2011-05-26 | Hiroyuki Kishino | 5/5-or 5/6-membered condensed ring cycloalkylamine derivative |
| EP2348857B1 (en) | 2008-10-22 | 2016-02-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| AU2009309037A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| UA99555C2 (en) * | 2008-11-12 | 2012-08-27 | Элджи Лайф Саенсез Лтд. | Melanocortin receptor agonists |
| US20110245209A1 (en) | 2008-12-16 | 2011-10-06 | Schering Corporation | Pyridopyrimidine derivatives and methods of use thereof |
| US20110243940A1 (en) | 2008-12-16 | 2011-10-06 | Schering Corporation | Bicyclic pyranone derivatives and methods of use thereof |
| US9040583B2 (en) | 2009-07-22 | 2015-05-26 | Temple University-Of The Commonwealth System Of Higher Education | Treatment of disorders associated with G protein-coupled receptor 35 (GPR35) |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| MY159058A (en) | 2011-02-25 | 2016-12-15 | Merck Sharp & Dohme | Novel cyclic azabenzimidazole derivatives useful as anti-diabetic agent |
| EP2880028B1 (en) | 2012-08-02 | 2020-09-30 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| EP2746253A1 (en) * | 2012-12-21 | 2014-06-25 | Unilever PLC | Novel compounds with skin lightening properties |
| GB201300435D0 (en) | 2013-01-10 | 2013-02-27 | Medical Res Council | Benzylideneguanidine Derivatives and Therapeutic Use for the Treatment of Protein Misfolding Diseases |
| JP2016516004A (ja) | 2013-02-22 | 2016-06-02 | メルク・シャープ・アンド・ドーム・コーポレーションＭｅｒｃｋ Ｓｈａｒｐ ＆ Ｄｏｈｍｅ Ｃｏｒｐ． | 抗糖尿病二環式化合物 |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| AU2014235209B2 (en) | 2013-03-15 | 2018-06-14 | Bausch Health Ireland Limited | Guanylate cyclase receptor agonists combined with other drugs |
| HK1220696A1 (zh) | 2013-03-15 | 2017-05-12 | Bausch Health Ireland Limited | 鸟苷酸环化酶激动剂及其用途 |
| EP4424697A3 (en) | 2013-06-05 | 2024-12-25 | Bausch Health Ireland Limited | Ultra-pure agonists of guanylate cyclase c, method of making and using same |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| WO2015097513A1 (en) * | 2013-12-13 | 2015-07-02 | Anamar Derma Ab | Topical products for aminoguanidines |
| CN103880712B (zh) * | 2014-01-29 | 2015-12-02 | 广州英赛特生物技术有限公司 | 二氨基胍衍生物及其在制备动物饲用生长促进剂中的应用 |
| EP3164391B1 (en) * | 2014-07-02 | 2019-07-31 | InFlectis BioScience | O-alkyl-benzylideneguanidine derivatives and therapeutic use for the treatment of disorders associated an accumulation of misfolded proteins |
| BR112017003745A2 (pt) | 2014-08-29 | 2017-12-05 | Tes Pharma S R L | inibidores de semialdeído descarboxilase de ácido alfa-amino-beta-carboximucônico |
| TWI767945B (zh) | 2016-10-14 | 2022-06-21 | 義大利商Ｔｅｓ製藥（股份）責任有限公司 | α-胺基-β-羧基己二烯二酸半醛去羧酶之抑制劑 |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| US10968232B2 (en) | 2016-12-20 | 2021-04-06 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| CN113302189B (zh) | 2018-11-20 | 2025-09-05 | Tes制药有限责任公司 | α-氨基-β-羧基己二烯二酸半醛去羧酶的抑制剂 |
| LT3773558T (lt) | 2019-05-10 | 2022-09-12 | Synact Pharma Aps | Kompleksinis artrito gydymas |
| PE20220766A1 (es) * | 2019-11-07 | 2022-05-16 | Lg Chemical Ltd | Agonistas de receptor de melanocortina-4 |
| WO2022268825A1 (en) | 2021-06-21 | 2022-12-29 | Synact Pharma Aps | Phenyl pyrrole aminoguanidine salts and formulations |
| CN113979890B (zh) * | 2021-10-27 | 2023-09-26 | 温州大学 | 一种席夫碱配体及其多核稀土配合物的制备方法和应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2036989A1 (en) | 1969-04-28 | 1970-12-31 | Anvar | Amidino hydrazone antivirals |
| US3592935A (en) * | 1969-12-11 | 1971-07-13 | Sandoz Ag | Substituted benzylidene hydrazines as anti-inflammatory agents |
| US3982020A (en) * | 1970-03-17 | 1976-09-21 | Sandoz, Inc. | Substituted benzylidene hydrazines for treating hyperglycemia, obesity and inflammation |
| US3975533A (en) * | 1970-04-29 | 1976-08-17 | Shell Oil Company | Therapeutic agents |
| JPS4842969B1 (enExample) | 1970-12-30 | 1973-12-15 | ||
| US3896232A (en) * | 1973-01-11 | 1975-07-22 | Sandoz Ag | Substituted benzylidene hydrazines as anti-migraine syndrome agents |
| US4006249A (en) * | 1975-08-06 | 1977-02-01 | American Home Products Corporation | Systemic treatment of psoriasis |
| US4006250A (en) * | 1975-08-25 | 1977-02-01 | American Home Products Corporation | Systemic treatment of psoriasis |
| FR2324294A1 (fr) | 1975-09-22 | 1977-04-15 | Roussel Uclaf | Nouveau medicament hypotenseur a action retardee, ainsi que le procede de preparation de ce nouveau medicament |
| JPS5562017A (en) | 1978-11-01 | 1980-05-10 | Teijin Ltd | Anti-inflammatory agent comprising guanidine derivative |
| US5958933A (en) | 1982-11-23 | 1999-09-28 | Naftchi; N. Eric | Neurologically active compounds and compounds with multiple activities |
| DE3428342A1 (de) | 1984-08-01 | 1986-02-13 | Boehringer Ingelheim Vetmedica GmbH, 6507 Ingelheim | Futtermittelzusatz zur verbesserung des wachstums bei landwirtschaftlichen nutztieren |
| US6413962B1 (en) | 1988-05-02 | 2002-07-02 | N. Eric Naftchi | Guanidino compounds effective as anesthetics |
| HUT64023A (en) * | 1991-03-22 | 1993-11-29 | Sandoz Ag | Process for producing aminoguanidine derivatives and pharmaceutical compositions comprising such compounds |
| EP0600973A1 (en) | 1991-08-27 | 1994-06-15 | The Upjohn Company | A method for treatment of metabolic disorders and metabolism |
| US5599984A (en) * | 1994-01-21 | 1997-02-04 | The Picower Institute For Medical Research | Guanylhydrazones and their use to treat inflammatory conditions |
| AU2629795A (en) * | 1994-12-12 | 1996-07-03 | Chugai Seiyaku Kabushiki Kaisha | Aniline derivative having the effect of inhibiting nitrogen monoxide synthase |
| SE9604348D0 (sv) | 1996-11-26 | 1996-11-26 | Wapharm Ab | Användning av hydroxyguanidiner |
| JP2002517444A (ja) | 1998-06-11 | 2002-06-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作動薬としてのスピロピペリジン誘導体 |
| GB9827500D0 (en) | 1998-12-14 | 1999-02-10 | Wapharm Ab | Compounds for control of eating, growth and body weight |
| AU7802700A (en) | 1999-10-06 | 2001-05-10 | Melacure Therapeutics Ab | Guanidine derivatives and their use in the production of a medicament for blocking xanthine oxidase/dehydrogenase |
| GB0019359D0 (en) | 2000-08-07 | 2000-09-27 | Melacure Therapeutics Ab | Novel guanidines |
-
2000
- 2000-08-07 GB GBGB0019359.9A patent/GB0019359D0/en not_active Ceased
-
2001
- 2001-08-07 WO PCT/GB2001/003556 patent/WO2002012178A1/en not_active Ceased
- 2001-08-07 MX MXPA03001073A patent/MXPA03001073A/es active IP Right Grant
- 2001-08-07 AT AT01954195T patent/ATE413382T1/de not_active IP Right Cessation
- 2001-08-07 DK DK01954195T patent/DK1309544T3/da active
- 2001-08-07 EP EP01954195A patent/EP1309544B1/en not_active Expired - Lifetime
- 2001-08-07 ES ES01954195T patent/ES2316460T3/es not_active Expired - Lifetime
- 2001-08-07 CA CA2417904A patent/CA2417904C/en not_active Expired - Fee Related
- 2001-08-07 US US10/343,326 patent/US7153881B2/en not_active Expired - Fee Related
- 2001-08-07 IL IL15427101A patent/IL154271A0/xx not_active IP Right Cessation
- 2001-08-07 KR KR1020037001847A patent/KR100911888B1/ko not_active Expired - Fee Related
- 2001-08-07 BR BR0113064-1A patent/BR0113064A/pt not_active Application Discontinuation
- 2001-08-07 JP JP2002518156A patent/JP4891516B2/ja not_active Expired - Fee Related
- 2001-08-07 DE DE60136468T patent/DE60136468D1/de not_active Expired - Lifetime
- 2001-08-07 AU AU2001276539A patent/AU2001276539A1/en not_active Abandoned
-
2003
- 2003-01-31 ZA ZA200300883A patent/ZA200300883B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7153881B2 (en) | 2006-12-26 |
| ES2316460T3 (es) | 2009-04-16 |
| BR0113064A (pt) | 2003-07-08 |
| WO2002012178A1 (en) | 2002-02-14 |
| KR20030022372A (ko) | 2003-03-15 |
| CA2417904C (en) | 2011-09-20 |
| EP1309544A1 (en) | 2003-05-14 |
| AU2001276539A1 (en) | 2002-02-18 |
| GB0019359D0 (en) | 2000-09-27 |
| US20040019094A1 (en) | 2004-01-29 |
| DK1309544T3 (da) | 2009-03-02 |
| MXPA03001073A (es) | 2004-03-10 |
| ATE413382T1 (de) | 2008-11-15 |
| DE60136468D1 (de) | 2008-12-18 |
| HK1055254A1 (en) | 2004-01-02 |
| IL154271A0 (en) | 2003-09-17 |
| JP4891516B2 (ja) | 2012-03-07 |
| JP2004505947A (ja) | 2004-02-26 |
| KR100911888B1 (ko) | 2009-08-11 |
| CA2417904A1 (en) | 2002-02-14 |
| EP1309544B1 (en) | 2008-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2417904C (en) | Compounds acting as melanocortin receptor ligands | |
| US7186748B2 (en) | N-phenylpyrrole guanidine derivatives as melanocortin receptor ligands | |
| US8309609B2 (en) | Use of benzylideneaminoguanidines and hydroxyguanidines as melanocortin receptor ligands | |
| AU2002313542A1 (en) | N-phenylpyrrole guanidine derivatives as melanocortin reception ligands | |
| EP1254114A2 (en) | Melanocortin receptor agonists and antagonists | |
| WO2001055107A2 (en) | Aromatic amines and amides acting on the melanocortin receptors | |
| WO2001055109A1 (en) | Aromatic amides acting on melanocortin receptors | |
| GB2398299A (en) | Pharmaceutically active phenyl-pyrrole derivatives | |
| HK1055254B (en) | Compounds acting as melanocortin receptor ligands |