ZA200305100B - 2-Arylimino-2,3-dihydrothiazole derivatives, methods for preparing them and therapeutic use thereof. - Google Patents
2-Arylimino-2,3-dihydrothiazole derivatives, methods for preparing them and therapeutic use thereof. Download PDFInfo
- Publication number
- ZA200305100B ZA200305100B ZA200305100A ZA200305100A ZA200305100B ZA 200305100 B ZA200305100 B ZA 200305100B ZA 200305100 A ZA200305100 A ZA 200305100A ZA 200305100 A ZA200305100 A ZA 200305100A ZA 200305100 B ZA200305100 B ZA 200305100B
- Authority
- ZA
- South Africa
- Prior art keywords
- radical
- formula
- finally
- syndrome
- composition
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims 9
- 150000001875 compounds Chemical class 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 206010016654 Fibrosis Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 206010012735 Diarrhoea Diseases 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 230000004761 fibrosis Effects 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 230000001575 pathological effect Effects 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 208000032843 Hemorrhage Diseases 0.000 claims description 9
- 108050001286 Somatostatin Receptor Proteins 0.000 claims description 9
- 102000011096 Somatostatin receptor Human genes 0.000 claims description 9
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 208000003200 Adenoma Diseases 0.000 claims description 6
- 238000002512 chemotherapy Methods 0.000 claims description 6
- 230000003111 delayed effect Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
- 208000034158 bleeding Diseases 0.000 claims description 4
- 230000000740 bleeding effect Effects 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 201000002510 thyroid cancer Diseases 0.000 claims description 4
- 208000030507 AIDS Diseases 0.000 claims description 3
- 206010007270 Carcinoid syndrome Diseases 0.000 claims description 3
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 201000000052 gastrinoma Diseases 0.000 claims description 3
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 206010059245 Angiopathy Diseases 0.000 claims description 2
- 206010003445 Ascites Diseases 0.000 claims description 2
- 208000023328 Basedow disease Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010006895 Cachexia Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 206010052097 Dawn phenomenon Diseases 0.000 claims description 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 2
- 208000008279 Dumping Syndrome Diseases 0.000 claims description 2
- 206010058314 Dysplasia Diseases 0.000 claims description 2
- 208000021006 GRFoma Diseases 0.000 claims description 2
- 102000004862 Gastrin releasing peptide Human genes 0.000 claims description 2
- 108090001053 Gastrin releasing peptide Proteins 0.000 claims description 2
- 206010017886 Gastroduodenal ulcer Diseases 0.000 claims description 2
- 206010018404 Glucagonoma Diseases 0.000 claims description 2
- 208000015023 Graves' disease Diseases 0.000 claims description 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 206010020850 Hyperthyroidism Diseases 0.000 claims description 2
- 208000001953 Hypotension Diseases 0.000 claims description 2
- 208000009164 Islet Cell Adenoma Diseases 0.000 claims description 2
- 206010029748 Noonan syndrome Diseases 0.000 claims description 2
- 208000002193 Pain Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010033635 Pancreatic pseudocyst Diseases 0.000 claims description 2
- 206010033664 Panic attack Diseases 0.000 claims description 2
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 claims description 2
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 claims description 2
- 208000032395 Post gastric surgery syndrome Diseases 0.000 claims description 2
- 206010036832 Prolactinoma Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 208000034189 Sclerosis Diseases 0.000 claims description 2
- 208000033781 Thyroid carcinoma Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 208000009311 VIPoma Diseases 0.000 claims description 2
- 206010052428 Wound Diseases 0.000 claims description 2
- 208000027418 Wounds and injury Diseases 0.000 claims description 2
- 238000002399 angioplasty Methods 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 230000001925 catabolic effect Effects 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 claims description 2
- PUBCCFNQJQKCNC-XKNFJVFFSA-N gastrin-releasingpeptide Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)C(C)C)[C@@H](C)O)C(C)C)[C@@H](C)O)C(C)C)C1=CNC=N1 PUBCCFNQJQKCNC-XKNFJVFFSA-N 0.000 claims description 2
- 231100000029 gastro-duodenal ulcer Toxicity 0.000 claims description 2
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 2
- 208000030304 gastrointestinal bleeding Diseases 0.000 claims description 2
- 239000003862 glucocorticoid Substances 0.000 claims description 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 2
- 201000008980 hyperinsulinism Diseases 0.000 claims description 2
- 230000036543 hypotension Effects 0.000 claims description 2
- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 206010022498 insulinoma Diseases 0.000 claims description 2
- 230000000968 intestinal effect Effects 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 201000006370 kidney failure Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 210000004072 lung Anatomy 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 206010027191 meningioma Diseases 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 208000021255 pancreatic insulinoma Diseases 0.000 claims description 2
- 208000019906 panic disease Diseases 0.000 claims description 2
- 230000007170 pathology Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 208000007232 portal hypertension Diseases 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 201000002859 sleep apnea Diseases 0.000 claims description 2
- 210000000813 small intestine Anatomy 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- 229940037128 systemic glucocorticoids Drugs 0.000 claims description 2
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 12
- UHFICAKXFHFOCN-UHFFFAOYSA-N 6-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC=C21 UHFICAKXFHFOCN-UHFFFAOYSA-N 0.000 claims 1
- 208000000624 Esophageal and Gastric Varices Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 206010056091 Varices oesophageal Diseases 0.000 claims 1
- 206010046996 Varicose vein Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000024170 esophageal varices Diseases 0.000 claims 1
- 201000010120 esophageal varix Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 208000027185 varicose disease Diseases 0.000 claims 1
- -1 carbocyclic aryl radical Chemical class 0.000 description 41
- 125000003118 aryl group Chemical group 0.000 description 29
- 150000003254 radicals Chemical class 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 20
- 125000002837 carbocyclic group Chemical group 0.000 description 14
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 229910052794 bromium Inorganic materials 0.000 description 9
- 125000001188 haloalkyl group Chemical group 0.000 description 9
- 102000005157 Somatostatin Human genes 0.000 description 8
- 108010056088 Somatostatin Proteins 0.000 description 8
- NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 8
- 229960000553 somatostatin Drugs 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000004438 haloalkoxy group Chemical group 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 125000004103 aminoalkyl group Chemical group 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 108010051696 Growth Hormone Proteins 0.000 description 4
- 102100038803 Somatotropin Human genes 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 239000000122 growth hormone Substances 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- 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 4
- 230000003248 secreting effect Effects 0.000 description 4
- 230000004913 activation Effects 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- 125000006213 aryl hydroxyalkyl group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000000668 Chronic Pancreatitis Diseases 0.000 description 1
- 206010018265 Gigantism Diseases 0.000 description 1
- 102000051325 Glucagon Human genes 0.000 description 1
- 108060003199 Glucagon Proteins 0.000 description 1
- 206010033647 Pancreatitis acute Diseases 0.000 description 1
- 206010033649 Pancreatitis chronic Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- 102100024819 Prolactin Human genes 0.000 description 1
- 108010057464 Prolactin Proteins 0.000 description 1
- 206010038934 Retinopathy proliferative Diseases 0.000 description 1
- 201000008629 Zollinger-Ellison syndrome Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 201000003229 acute pancreatitis Diseases 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 208000002458 carcinoid tumor Diseases 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 description 1
- 229960004666 glucagon Drugs 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 210000003016 hypothalamus Anatomy 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001326 naphthylalkyl group Chemical group 0.000 description 1
- 230000014399 negative regulation of angiogenesis Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229940127264 non-peptide agonist Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/02—Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Developing Agents For Electrophotography (AREA)
- Liquid Crystal (AREA)
- Thin Film Transistor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pressure Welding/Diffusion-Bonding (AREA)
- Chemical Vapour Deposition (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0100396A FR2819508B1 (fr) | 2001-01-12 | 2001-01-12 | Derives de 2-arylimino-2, 3-dihydorthiazoles, leurs procedes de preparation et leur utilisation therapeutiques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200305100B true ZA200305100B (en) | 2004-08-27 |
Family
ID=8858747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200305100A ZA200305100B (en) | 2001-01-12 | 2003-06-30 | 2-Arylimino-2,3-dihydrothiazole derivatives, methods for preparing them and therapeutic use thereof. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7220765B2 (ko) |
| EP (1) | EP1353912B1 (ko) |
| JP (1) | JP4452443B2 (ko) |
| KR (1) | KR100874298B1 (ko) |
| CN (1) | CN100534988C (ko) |
| AR (1) | AR035730A1 (ko) |
| AT (1) | ATE302765T1 (ko) |
| AU (1) | AU2002233407B2 (ko) |
| BR (1) | BR0206407A (ko) |
| CA (1) | CA2434203C (ko) |
| CZ (1) | CZ20031917A3 (ko) |
| DE (1) | DE60205717T2 (ko) |
| DK (1) | DK1353912T3 (ko) |
| ES (1) | ES2248514T3 (ko) |
| FR (1) | FR2819508B1 (ko) |
| HU (1) | HUP0500958A3 (ko) |
| IL (2) | IL156647A0 (ko) |
| IS (1) | IS2331B (ko) |
| MX (1) | MXPA03006249A (ko) |
| MY (1) | MY142762A (ko) |
| NO (1) | NO325484B1 (ko) |
| NZ (1) | NZ526692A (ko) |
| PL (1) | PL367627A1 (ko) |
| RU (1) | RU2283838C2 (ko) |
| WO (1) | WO2002055510A1 (ko) |
| ZA (1) | ZA200305100B (ko) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1669352A4 (en) | 2003-09-30 | 2008-12-17 | Takeda Pharmaceutical | THIAZOLINE DERIVATIVE AND ITS USE |
| JP4896387B2 (ja) * | 2003-09-30 | 2012-03-14 | 武田薬品工業株式会社 | チアゾリン誘導体およびその用途 |
| JP2009507813A (ja) * | 2005-09-13 | 2009-02-26 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 殺有害生物剤ビ−フェニル−アミジン誘導体 |
| KR100863239B1 (ko) | 2007-05-23 | 2008-10-15 | 한국과학기술연구원 | 신규한 2-이미노-1,3-티아졸린계 화합물 및 이를 함유하는ｔ-형 칼슘 채널 저해제 |
| KR20110037930A (ko) * | 2008-06-23 | 2011-04-13 | 토소가부시키가이샤 | 단백질 정제용 분리제 및 단백질 정제방법 |
| KR101049935B1 (ko) | 2008-12-03 | 2011-07-15 | 한국과학기술연구원 | 신규한 티아졸린계 화합물 및 이를 포함하는 ｔ-형 칼슘 채널 저해제 |
| ES2351569B8 (es) * | 2009-05-07 | 2012-06-20 | Bcn Peptides S.A. | Ligandos peptídicos de receptores de somatostatina. |
| JP5181156B2 (ja) | 2010-08-09 | 2013-04-10 | 株式会社ファルマデザイン | カゼインキナーゼ１δ及びカゼインキナーゼ１ε阻害剤 |
| RU2521390C1 (ru) * | 2013-03-14 | 2014-06-27 | Общество с ограниченной ответственностью "Тиацен" | Производное роданина и средство для профилактики опухолевых заболеваний |
| JP6894498B2 (ja) * | 2016-08-12 | 2021-06-30 | ザ カトリック ユニバーシティ オブ コリア インダストリー−アカデミック コーオペレイション ファウンデーション | 軟組織硬化用組成物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1347371A (fr) * | 1962-01-19 | 1963-12-27 | Ciba Geigy | Agents de lutte contre les organismes nuisibles, renfermant des thiazolines, à usages agricoles et industriels |
| DE2926771A1 (de) * | 1979-07-03 | 1981-01-15 | Hoechst Ag | Thiazolidinderivate und verfahren zu ihrer herstellung |
| DE3049460A1 (de) * | 1980-12-30 | 1982-07-29 | Hoechst Ag, 6000 Frankfurt | "thiazolinderivate, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| FR2735777B1 (fr) * | 1995-06-21 | 1997-09-12 | Sanofi Sa | Derives de 4-phenylaminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant |
| FR2796643B1 (fr) * | 1999-07-22 | 2005-04-29 | Sod Conseils Rech Applic | Derives de 2-arylimino-2, 3-dihydrothiazoles, leurs procedes de preparation et leur utilisation therapeutique |
-
2001
- 2001-01-12 FR FR0100396A patent/FR2819508B1/fr not_active Expired - Fee Related
- 2001-12-27 MY MYPI20015897A patent/MY142762A/en unknown
-
2002
- 2002-01-11 RU RU2003124749/04A patent/RU2283838C2/ru not_active IP Right Cessation
- 2002-01-11 BR BR0206407-3A patent/BR0206407A/pt not_active IP Right Cessation
- 2002-01-11 NZ NZ526692A patent/NZ526692A/en unknown
- 2002-01-11 CZ CZ20031917A patent/CZ20031917A3/cs unknown
- 2002-01-11 PL PL02367627A patent/PL367627A1/xx not_active Application Discontinuation
- 2002-01-11 JP JP2002556180A patent/JP4452443B2/ja not_active Expired - Fee Related
- 2002-01-11 HU HU0500958A patent/HUP0500958A3/hu unknown
- 2002-01-11 MX MXPA03006249A patent/MXPA03006249A/es active IP Right Grant
- 2002-01-11 WO PCT/FR2002/000093 patent/WO2002055510A1/fr active IP Right Grant
- 2002-01-11 IL IL15664702A patent/IL156647A0/xx unknown
- 2002-01-11 AU AU2002233407A patent/AU2002233407B2/en not_active Ceased
- 2002-01-11 DK DK02700318T patent/DK1353912T3/da active
- 2002-01-11 AR ARP020100094A patent/AR035730A1/es unknown
- 2002-01-11 DE DE60205717T patent/DE60205717T2/de not_active Expired - Lifetime
- 2002-01-11 KR KR1020037009303A patent/KR100874298B1/ko not_active IP Right Cessation
- 2002-01-11 EP EP02700318A patent/EP1353912B1/fr not_active Expired - Lifetime
- 2002-01-11 CA CA2434203A patent/CA2434203C/fr not_active Expired - Fee Related
- 2002-01-11 ES ES02700318T patent/ES2248514T3/es not_active Expired - Lifetime
- 2002-01-11 CN CNB02803662XA patent/CN100534988C/zh not_active Expired - Fee Related
- 2002-01-11 AT AT02700318T patent/ATE302765T1/de not_active IP Right Cessation
-
2003
- 2003-06-25 IL IL156647A patent/IL156647A/en not_active IP Right Cessation
- 2003-06-30 ZA ZA200305100A patent/ZA200305100B/en unknown
- 2003-07-08 US US10/615,481 patent/US7220765B2/en not_active Expired - Fee Related
- 2003-07-08 NO NO20033120A patent/NO325484B1/no not_active IP Right Cessation
- 2003-07-09 IS IS6870A patent/IS2331B/is unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2266287C2 (ru) | 2-арилимино-2,3-дигидротиазолы, способы их получения и фармацевтическая композиция, их содержащая | |
| US7332517B2 (en) | Derivatives of hydantoins, thiohydantoins, pyrimidinediones and thioxopyrimidinones, their preparation processes and their use as medicaments | |
| KR102138391B1 (ko) | 체액 저류 또는 염 과부하와 연관된 장애 및 위장관 장애의 치료에서 ｎｈｅ-매개된 역수송 저해를 위한 화합물 및 방법 | |
| US8143394B2 (en) | Pyrido(3,2-d)pyrimidines useful for treating viral infections | |
| US9149540B2 (en) | Polymer conjugate of folic acid or folic acid derivative | |
| US11466018B2 (en) | TGF-β inhibitors | |
| CN105960237B (zh) | Ccr6化合物 | |
| ZA200305100B (en) | 2-Arylimino-2,3-dihydrothiazole derivatives, methods for preparing them and therapeutic use thereof. | |
| US10315990B2 (en) | Isothiocyanate compounds and isothiocyanate XPO1 protein inhibitor drugs thereof | |
| WO1998035944A1 (en) | Amides as npy5 receptor antagonists | |
| EP1163244A1 (en) | Thienopyrimidine compounds, their production and use | |
| HU229221B1 (en) | Vitronectin receptor antagonists | |
| US20160200681A1 (en) | Tetrahydrocyclopentapyrrole Derivatives and a Method for Preparing the Same | |
| WO2008077650A1 (en) | Pyrido(3,2-d)pyrimidines useful for treating viral infections | |
| AU2018206479B2 (en) | Inhibitors of NHE-mediated antiport | |
| CN114040765A (zh) | 癌症免疫治疗佐剂 | |
| US10351577B2 (en) | Ether analogues of galiellalactone | |
| CA2553243A1 (en) | Pyrrolo pyrimidine derivatives useful for treating proliferative diseases | |
| NL8302935A (nl) | Nieuwe polypeptiden, werkwijzen voor hun bereiding, farmaceutische preparaten die deze polypeptiden bevatten en hun toepassing. | |
| CN101921238B (zh) | 取代苯并氮杂环类衍生物的制备及其药理用途 | |
| WO2015132396A1 (en) | Tricyclic prodrugs | |
| CA2509665A1 (en) | Tricyclic aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase-2 | |
| EP3747909A1 (en) | Anticancer agent | |
| CN117510413A (zh) | 一种dclk1激酶抑制剂及其制备方法和应用 |