NZ502965A - Benzenesulfonamide inhibitors of phosphodiesterase-IV for treating inflammation and TNF associated diseases - Google Patents
Benzenesulfonamide inhibitors of phosphodiesterase-IV for treating inflammation and TNF associated diseasesInfo
- Publication number
- NZ502965A NZ502965A NZ502965A NZ50296598A NZ502965A NZ 502965 A NZ502965 A NZ 502965A NZ 502965 A NZ502965 A NZ 502965A NZ 50296598 A NZ50296598 A NZ 50296598A NZ 502965 A NZ502965 A NZ 502965A
- Authority
- NZ
- New Zealand
- Prior art keywords
- dimethoxybenzenesulfonamide
- methyl
- disease
- disease state
- pharmaceutical composition
- Prior art date
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 49
- 201000010099 disease Diseases 0.000 title claims description 47
- 206010061218 Inflammation Diseases 0.000 title claims description 4
- 230000004054 inflammatory process Effects 0.000 title claims description 4
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 title description 18
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 title description 18
- 239000003112 inhibitor Substances 0.000 title description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 18
- 241001070944 Mimosa Species 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 210000003979 eosinophil Anatomy 0.000 claims description 15
- 230000006870 function Effects 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 206010040070 Septic Shock Diseases 0.000 claims description 10
- 208000006673 asthma Diseases 0.000 claims description 10
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
- 201000008937 atopic dermatitis Diseases 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 206010017533 Fungal infection Diseases 0.000 claims description 8
- 238000009825 accumulation Methods 0.000 claims description 8
- 206010003246 arthritis Diseases 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 208000011231 Crohn disease Diseases 0.000 claims description 6
- 206010039966 Senile dementia Diseases 0.000 claims description 6
- 206010040047 Sepsis Diseases 0.000 claims description 6
- 208000026935 allergic disease Diseases 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 208000030507 AIDS Diseases 0.000 claims description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 5
- 208000000112 Myalgia Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 5
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 201000005569 Gout Diseases 0.000 claims description 4
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 4
- 208000031888 Mycoses Diseases 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 230000002917 arthritic effect Effects 0.000 claims description 4
- 230000002490 cerebral effect Effects 0.000 claims description 4
- 206010022000 influenza Diseases 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 230000002685 pulmonary effect Effects 0.000 claims description 4
- 230000036303 septic shock Effects 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010006895 Cachexia Diseases 0.000 claims description 3
- 206010063094 Cerebral malaria Diseases 0.000 claims description 3
- 206010014824 Endotoxic shock Diseases 0.000 claims description 3
- 208000010496 Heart Arrest Diseases 0.000 claims description 3
- 206010020649 Hyperkeratosis Diseases 0.000 claims description 3
- 206010022562 Intermittent claudication Diseases 0.000 claims description 3
- 208000001126 Keratosis Diseases 0.000 claims description 3
- 206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010037660 Pyrexia Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 201000010001 Silicosis Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 206010044248 Toxic shock syndrome Diseases 0.000 claims description 3
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- 208000024780 Urticaria Diseases 0.000 claims description 3
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 208000019664 bone resorption disease Diseases 0.000 claims description 3
- 206010006451 bronchitis Diseases 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 201000010064 diabetes insipidus Diseases 0.000 claims description 3
- 208000003401 eosinophilic granuloma Diseases 0.000 claims description 3
- 208000024908 graft versus host disease Diseases 0.000 claims description 3
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 3
- 208000011379 keloid formation Diseases 0.000 claims description 3
- 206010027175 memory impairment Diseases 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 231100000241 scar Toxicity 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 230000009772 tissue formation Effects 0.000 claims description 3
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims description 2
- 201000004810 Vascular dementia Diseases 0.000 claims description 2
- 238000003556 assay Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims 4
- 239000007983 Tris buffer Substances 0.000 claims 4
- 239000011324 bead Substances 0.000 claims 4
- 208000018937 joint inflammation Diseases 0.000 claims 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 4
- YAOYWZXMBDONEU-UHFFFAOYSA-N 3,4-dimethoxy-n-methyl-n-propylbenzenesulfonamide Chemical compound CCCN(C)S(=O)(=O)C1=CC=C(OC)C(OC)=C1 YAOYWZXMBDONEU-UHFFFAOYSA-N 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- FXSUKMJRXIFFPV-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)sulfonylpiperidine Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1CCCCC1 FXSUKMJRXIFFPV-UHFFFAOYSA-N 0.000 claims 2
- VMGCIRQIOSUXBQ-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)sulfonylpyrrolidine Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1CCCC1 VMGCIRQIOSUXBQ-UHFFFAOYSA-N 0.000 claims 2
- KQCZCINJGIRLCD-UHFFFAOYSA-N 2-bromo-n-[4-chloro-3-(1-methylpyrrolidin-3-yl)oxyphenyl]-4,5-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC(Br)=C1S(=O)(=O)NC1=CC=C(Cl)C(OC2CN(C)CC2)=C1 KQCZCINJGIRLCD-UHFFFAOYSA-N 0.000 claims 2
- SYBKBMOUDRMMGL-UHFFFAOYSA-N 3,4-diethoxy-n-methyl-n-prop-2-enylbenzenesulfonamide Chemical compound CCOC1=CC=C(S(=O)(=O)N(C)CC=C)C=C1OCC SYBKBMOUDRMMGL-UHFFFAOYSA-N 0.000 claims 2
- FIGXUCHSGNGHJE-UHFFFAOYSA-N 3,4-diethoxy-n-methyl-n-prop-2-ynylbenzenesulfonamide Chemical compound CCOC1=CC=C(S(=O)(=O)N(C)CC#C)C=C1OCC FIGXUCHSGNGHJE-UHFFFAOYSA-N 0.000 claims 2
- ACFVRBTXBOKFTG-UHFFFAOYSA-N 3,4-dimethoxy-n,n-bis(prop-2-enyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(CC=C)CC=C)C=C1OC ACFVRBTXBOKFTG-UHFFFAOYSA-N 0.000 claims 2
- IELNGZSDMUQHIT-UHFFFAOYSA-N 3,4-dimethoxy-n,n-dimethylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1OC IELNGZSDMUQHIT-UHFFFAOYSA-N 0.000 claims 2
- UMRIXCYCRBLAMD-UHFFFAOYSA-N 3,4-dimethoxy-n-methyl-n-(2-oxopropyl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)CC(C)=O)C=C1OC UMRIXCYCRBLAMD-UHFFFAOYSA-N 0.000 claims 2
- RPRWDTKMJVEYSY-UHFFFAOYSA-N 3,4-dimethoxy-n-methyl-n-prop-2-enylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)CC=C)C=C1OC RPRWDTKMJVEYSY-UHFFFAOYSA-N 0.000 claims 2
- OAUBVWQJHVCRDC-UHFFFAOYSA-N 3,4-dimethoxy-n-methyl-n-prop-2-ynylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)CC#C)C=C1OC OAUBVWQJHVCRDC-UHFFFAOYSA-N 0.000 claims 2
- 206010018367 Glomerulonephritis chronic Diseases 0.000 claims 2
- 206010019617 Henoch-Schonlein purpura Diseases 0.000 claims 2
- 208000031814 IgA Vasculitis Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 2
- 208000025865 Ulcer Diseases 0.000 claims 2
- 239000012131 assay buffer Substances 0.000 claims 2
- 208000015446 immunoglobulin a vasculitis Diseases 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims 2
- 201000004792 malaria Diseases 0.000 claims 2
- HGHMNKFJLGKOLQ-UHFFFAOYSA-N n,n-diethyl-3,4-dimethoxybenzenesulfonamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(OC)=C1 HGHMNKFJLGKOLQ-UHFFFAOYSA-N 0.000 claims 2
- WYIZXMIXAXBEGF-UHFFFAOYSA-N n-but-2-enyl-3,4-dimethoxy-n-methylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N(C)CC=CC)C=C1OC WYIZXMIXAXBEGF-UHFFFAOYSA-N 0.000 claims 2
- 201000008383 nephritis Diseases 0.000 claims 2
- 201000005539 vernal conjunctivitis Diseases 0.000 claims 2
- MZINALKGDOTWPE-UHFFFAOYSA-N 3,4-diethoxy-n,n-dimethylbenzenesulfonamide Chemical compound CCOC1=CC=C(S(=O)(=O)N(C)C)C=C1OCC MZINALKGDOTWPE-UHFFFAOYSA-N 0.000 claims 1
- GLZNXUSFGVIJHV-UHFFFAOYSA-N 3,4-dimethoxy-n,n-dipropylbenzenesulfonamide Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(OC)C(OC)=C1 GLZNXUSFGVIJHV-UHFFFAOYSA-N 0.000 claims 1
- PPSZHJPDWVEFFZ-UHFFFAOYSA-N 3,4-dimethoxy-n-methyl-n-(3-oxopentyl)benzenesulfonamide Chemical compound CCC(=O)CCN(C)S(=O)(=O)C1=CC=C(OC)C(OC)=C1 PPSZHJPDWVEFFZ-UHFFFAOYSA-N 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 239000013592 cell lysate Substances 0.000 claims 1
- 239000006166 lysate Substances 0.000 claims 1
- LKDUZTQGSJMBCM-UHFFFAOYSA-N n-ethyl-3,4-dimethoxy-n-methylbenzenesulfonamide Chemical compound CCN(C)S(=O)(=O)C1=CC=C(OC)C(OC)=C1 LKDUZTQGSJMBCM-UHFFFAOYSA-N 0.000 claims 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 claims 1
- 229950005741 rolipram Drugs 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims 1
- 229960001763 zinc sulfate Drugs 0.000 claims 1
- 229910000368 zinc sulfate Inorganic materials 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- 102000018594 Tumour necrosis factor Human genes 0.000 description 28
- 108050007852 Tumour necrosis factor Proteins 0.000 description 28
- 239000000203 mixture Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241000700605 Viruses Species 0.000 description 7
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 241000124008 Mammalia Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- 239000006071 cream Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 241000701022 Cytomegalovirus Species 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- -1 sulfonamide compounds Chemical class 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
- 102100040247 Tumor necrosis factor Human genes 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000012049 topical pharmaceutical composition Substances 0.000 description 3
- 230000006433 tumor necrosis factor production Effects 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- RSJSYCZYQNJQPY-UHFFFAOYSA-N 3,4-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1OC RSJSYCZYQNJQPY-UHFFFAOYSA-N 0.000 description 2
- 206010001513 AIDS related complex Diseases 0.000 description 2
- 241000220479 Acacia Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
- 241000713800 Feline immunodeficiency virus Species 0.000 description 2
- 101100134922 Gallus gallus COR5 gene Chemical group 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 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 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229940095074 cyclic amp Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000000670 limiting effect Effects 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
- 239000000463 material Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 206010020164 HIV infection CDC Group III Diseases 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- HUYWAWARQUIQLE-UHFFFAOYSA-N Isoetharine Chemical compound CC(C)NC(CC)C(O)C1=CC=C(O)C(O)=C1 HUYWAWARQUIQLE-UHFFFAOYSA-N 0.000 description 1
- 241000713666 Lentivirus Species 0.000 description 1
- 102000004083 Lymphotoxin-alpha Human genes 0.000 description 1
- 108090000542 Lymphotoxin-alpha Proteins 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010038687 Respiratory distress Diseases 0.000 description 1
- 206010038997 Retroviral infections Diseases 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241000713325 Visna/maedi virus Species 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 229960000258 corticotropin Drugs 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 230000003090 exacerbative effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229960001268 isoetarine Drugs 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- HQFYIDOMCULPIW-UHFFFAOYSA-N n-methylprop-2-yn-1-amine Chemical compound CNCC#C HQFYIDOMCULPIW-UHFFFAOYSA-N 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000002062 proliferating 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
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229960002052 salbutamol Drugs 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000008009 topical excipient Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
-
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4453—Non condensed piperidines, e.g. piperocaine only substituted in position 1, e.g. propipocaine, diperodon
-
- 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
-
- 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
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6694397P | 1997-11-25 | 1997-11-25 | |
| PCT/US1998/023482 WO1999026616A1 (en) | 1997-11-25 | 1998-11-04 | Benzenesulfonamide inhibitors of pde-iv and their therapeutic use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ502965A true NZ502965A (en) | 2002-03-01 |
Family
ID=22072726
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ502965A NZ502965A (en) | 1997-11-25 | 1998-11-04 | Benzenesulfonamide inhibitors of phosphodiesterase-IV for treating inflammation and TNF associated diseases |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6162830A (enExample) |
| EP (1) | EP1045690B1 (enExample) |
| JP (1) | JP2001523712A (enExample) |
| KR (1) | KR20010024268A (enExample) |
| AT (1) | ATE238048T1 (enExample) |
| AU (1) | AU751453C (enExample) |
| BR (1) | BR9812527A (enExample) |
| CA (1) | CA2299399C (enExample) |
| DE (1) | DE69813895T2 (enExample) |
| DK (1) | DK1045690T3 (enExample) |
| ES (1) | ES2195419T3 (enExample) |
| NZ (1) | NZ502965A (enExample) |
| PT (1) | PT1045690E (enExample) |
| WO (1) | WO1999026616A1 (enExample) |
| ZA (1) | ZA9810735B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6316503B1 (en) * | 1999-03-15 | 2001-11-13 | Tularik Inc. | LXR modulators |
| JP3940290B2 (ja) * | 2000-12-22 | 2007-07-04 | ザ・ヨルダニアン・フアーマシユーテイカル・エム・エフ・ジー・アンド・メデイカル・イクイツプメント・カンパニー・リミテツド | 新規化合物 |
| US6699890B2 (en) | 2000-12-22 | 2004-03-02 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| SE0004780D0 (sv) | 2000-12-22 | 2000-12-22 | Jordanian Pharmaceutical Mfg & | Novel compunds |
| US7153871B2 (en) * | 2001-01-22 | 2006-12-26 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs |
| US7205320B2 (en) * | 2001-01-22 | 2007-04-17 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| DE60324104D1 (en) * | 2002-01-30 | 2008-11-27 | Amgen Inc | Arylsulfonamidobenzylverbindungen |
| AU2003208952B2 (en) * | 2002-01-30 | 2008-04-24 | Amgen Inc. | Heterocyclic arylsulfonamidobenzylic compounds |
| US7893101B2 (en) | 2002-03-20 | 2011-02-22 | Celgene Corporation | Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof |
| US7276529B2 (en) * | 2002-03-20 | 2007-10-02 | Celgene Corporation | Methods of the treatment or prevention of exercise-induced asthma using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
| US6962940B2 (en) | 2002-03-20 | 2005-11-08 | Celgene Corporation | (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof |
| US7208516B2 (en) * | 2002-03-20 | 2007-04-24 | Celgene Corporation | Methods of the treatment of psoriatic arthritis using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
| CN1658848A (zh) * | 2002-04-12 | 2005-08-24 | 细胞基因公司 | 血管生成调节剂的鉴定方法,由此发现的化合物和使用该化合物的治疗方法 |
| ES2195785B1 (es) * | 2002-05-16 | 2005-03-16 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| MXPA05000827A (es) | 2002-07-19 | 2005-08-29 | Memory Pharm Corp | Inhibidores de fosfodiesterasa 4, incluyendo analogos de anilina y difenilamina n-sustituidos. |
| CN101423497A (zh) * | 2002-07-19 | 2009-05-06 | 记忆药物公司 | 作为磷酸二酯酶4抑制剂的6-氨基-1h-吲唑和4-氨基苯并呋喃化合物 |
| RU2356893C2 (ru) * | 2002-11-19 | 2009-05-27 | Мемори Фармасьютиклз Корпорейшн | Ингибиторы фосфодиэстеразы 4 |
| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US20060264424A1 (en) * | 2003-08-12 | 2006-11-23 | Tularik Inc | Arylsulfonamidobenzylic compounds |
| MY141255A (en) * | 2003-12-11 | 2010-03-31 | Memory Pharm Corp | Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs |
| ES2251866B1 (es) * | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| WO2009120296A1 (en) * | 2008-03-24 | 2009-10-01 | Celgene Corporation | Treatment of psoriasis or psoriatic arthritis using cyclopropyl-n-{2-{(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-3-oxoisoindoline-4-yl}carboxamide |
| WO2010003084A2 (en) * | 2008-07-02 | 2010-01-07 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
| FR2962649B1 (fr) | 2010-07-19 | 2025-10-24 | Conservatoire Nat Arts Et Metiers | Traitement d'une pathologie liee a un effet excessif du tnf par un compose de benzene sulfonamide |
| WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| WO2015200177A1 (en) | 2014-06-23 | 2015-12-30 | Celgene Corporation | Apremilast for the treatment of a liver disease or a liver function abnormality |
| CN111925313B (zh) * | 2020-09-22 | 2021-06-25 | 纳兰迦(上海)生物医药科技有限公司 | 具有pde4抑制活性的化合物、制备方法、组合物及用途 |
| JP7769365B2 (ja) * | 2021-09-22 | 2025-11-13 | 日本メナード化粧品株式会社 | 皮膚幹細胞増殖促進剤及び皮膚再生促進剤 |
| EP4197318B1 (en) * | 2021-12-17 | 2025-11-19 | Albert-Ludwigs-Universität Freiburg | Phosphodiesterases inhibitors to promote in vitro plant cell reprogramming towards plant embryogenesis or microcallus formation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5283352A (en) * | 1986-11-28 | 1994-02-01 | Orion-Yhtyma Oy | Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same |
| IL106517A0 (en) * | 1992-07-28 | 1994-08-26 | Rhone Poulenc Rorer Ltd | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic or heteroatom containing linking group |
| US6245774B1 (en) * | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| US5728712A (en) * | 1995-05-19 | 1998-03-17 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| AU5772296A (en) * | 1995-05-19 | 1996-11-29 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| AU5772396A (en) * | 1995-05-19 | 1996-11-29 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| JP2000510866A (ja) * | 1996-05-20 | 2000-08-22 | ダーウィン・ディスカバリー・リミテッド | Ｔｎｆとｐｄｅ―ｉｖのインヒビターとしてのキノリンスルホンアミド |
-
1998
- 1998-11-04 KR KR1020007003155A patent/KR20010024268A/ko not_active Ceased
- 1998-11-04 PT PT98957571T patent/PT1045690E/pt unknown
- 1998-11-04 ES ES98957571T patent/ES2195419T3/es not_active Expired - Lifetime
- 1998-11-04 BR BR9812527-3A patent/BR9812527A/pt not_active Application Discontinuation
- 1998-11-04 WO PCT/US1998/023482 patent/WO1999026616A1/en not_active Ceased
- 1998-11-04 DE DE69813895T patent/DE69813895T2/de not_active Expired - Fee Related
- 1998-11-04 EP EP98957571A patent/EP1045690B1/en not_active Expired - Lifetime
- 1998-11-04 AU AU13800/99A patent/AU751453C/en not_active Ceased
- 1998-11-04 DK DK98957571T patent/DK1045690T3/da active
- 1998-11-04 JP JP2000521818A patent/JP2001523712A/ja not_active Abandoned
- 1998-11-04 AT AT98957571T patent/ATE238048T1/de not_active IP Right Cessation
- 1998-11-04 US US09/485,252 patent/US6162830A/en not_active Expired - Fee Related
- 1998-11-04 CA CA002299399A patent/CA2299399C/en not_active Expired - Fee Related
- 1998-11-04 NZ NZ502965A patent/NZ502965A/en unknown
- 1998-11-24 ZA ZA9810735A patent/ZA9810735B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2299399C (en) | 2004-04-06 |
| ES2195419T3 (es) | 2003-12-01 |
| CA2299399A1 (en) | 1999-06-03 |
| EP1045690B1 (en) | 2003-04-23 |
| AU751453B2 (en) | 2002-08-15 |
| US6162830A (en) | 2000-12-19 |
| AU751453C (en) | 2003-04-10 |
| DK1045690T3 (da) | 2003-08-04 |
| KR20010024268A (ko) | 2001-03-26 |
| AU1380099A (en) | 1999-06-15 |
| PT1045690E (pt) | 2003-08-29 |
| DE69813895D1 (de) | 2003-05-28 |
| WO1999026616A1 (en) | 1999-06-03 |
| DE69813895T2 (de) | 2003-11-06 |
| BR9812527A (pt) | 2000-07-25 |
| ZA9810735B (en) | 1999-05-31 |
| ATE238048T1 (de) | 2003-05-15 |
| JP2001523712A (ja) | 2001-11-27 |
| EP1045690A1 (en) | 2000-10-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU751453C (en) | Benzenesulfonamide inhibitors of PDE-IV and their therapeutic use | |
| EP1986633B1 (en) | Treatment of duchenne muscular dystrophy | |
| US5919789A (en) | Xanthines and their therapeutic use | |
| US5753666A (en) | Quinolones and their therapeutic use | |
| CA2225552A1 (en) | Quinolones and their therapeutic use | |
| SA99200059A (ar) | مركبات إميدازول جديدة مستبدلة | |
| DE69620458T2 (de) | Benzofuran-carboxamide und -sulfonamide | |
| CZ286325B6 (cs) | Amidy kyseliny indazolylkarboxylové, farmaceutické prostředky s obsahem těchto látek | |
| JP2000510866A (ja) | Ｔｎｆとｐｄｅ―ｉｖのインヒビターとしてのキノリンスルホンアミド | |
| TW201533021A (zh) | 經取代之芐醯胺及其使用方法 | |
| CZ154599A3 (cs) | N-vázané sulfonamidy heterocyklických thioesterů | |
| WO2008029152A2 (en) | Treatment of duchenne muscular dystrophy | |
| JPH11505241A (ja) | キサンチン類およびこれらの治療的使用 | |
| TW201501713A (zh) | 眼炎症性疾病之預防及／或治療劑 | |
| EP2968207A1 (en) | Histone deacetylase inhibitors and compositions | |
| NO313913B1 (no) | IL-8 reseptor antagonister, anvendelse og fremgangsmÕte for fremstilling derav, samt farmasöytisk preparat | |
| JP2005527518A (ja) | 新規なカルコン（ｃｈａｌｃｏｎｅ）誘導体とその使用 | |
| KR20230169982A (ko) | 리보솜 장애와 관련된 빈혈을 치료하기 위한 조성물 및 방법 | |
| KR20010033842A (ko) | 티엔에프 및 피디이-ⅳ 억제 활성을 갖는 헤테로시클릭화합물의 엔-옥사이드 | |
| US6887882B2 (en) | Pharmaceutical compositions comprising chelidonine or derivatives thereof | |
| JP2002515051A (ja) | ヘテロ環式チオエステルのｎ−結合スルホンアミド | |
| MXPA00001750A (en) | Benzenesulfonamide inhibitors of pde-iv and their therapeutic use | |
| EP2456309B1 (en) | Azabicyclo[3.2.1]octyl derivatives for use in the treatment of HIV. | |
| WO2005072082A2 (en) | 2-guanidinylimidazolidinedione compounds and methods of making and using thereof | |
| HK40080028A (en) | Tyk2 pseudokinase ligands |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |