ZA200205599B - Heterocyclic derivatives, preparation method and pharmaceutical compositions containing same. - Google Patents
Heterocyclic derivatives, preparation method and pharmaceutical compositions containing same. Download PDFInfo
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- ZA200205599B ZA200205599B ZA200205599A ZA200205599A ZA200205599B ZA 200205599 B ZA200205599 B ZA 200205599B ZA 200205599 A ZA200205599 A ZA 200205599A ZA 200205599 A ZA200205599 A ZA 200205599A ZA 200205599 B ZA200205599 B ZA 200205599B
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- ZA
- South Africa
- Prior art keywords
- group
- formula
- ethoxy
- benzyl
- compounds
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 39
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 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 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- -1 carboxy, formyl Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 102000004877 Insulin Human genes 0.000 claims description 9
- 108090001061 Insulin Proteins 0.000 claims description 9
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229940125396 insulin Drugs 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 7
- 235000019260 propionic acid Nutrition 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 230000001419 dependent effect Effects 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 230000007170 pathology Effects 0.000 claims description 5
- 150000003222 pyridines Chemical class 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 201000001421 hyperglycemia Diseases 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 150000004892 pyridazines Chemical class 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010022489 Insulin Resistance Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims 4
- WWYDYZMNFQIYPT-UHFFFAOYSA-L 2-phenylpropanedioate Chemical compound [O-]C(=O)C(C([O-])=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-L 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 238000000926 separation method Methods 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- NODMFEUGZSXEJY-UHFFFAOYSA-N 3-[4-[3-(2-oxo-1,3-benzothiazol-3-yl)propyl]phenyl]prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1CCCN1C(=O)SC2=CC=CC=C21 NODMFEUGZSXEJY-UHFFFAOYSA-N 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000032928 Dyslipidaemia Diseases 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 claims 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 claims 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- 206010068871 Myotonic dystrophy Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 206010048214 Xanthoma Diseases 0.000 claims 1
- 206010048215 Xanthomatosis Diseases 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims 1
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 210000004351 coronary vessel Anatomy 0.000 claims 1
- 230000000911 decarboxylating effect Effects 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- DGTTVPRXEKLDPR-UHFFFAOYSA-N dimethyl 2-[[4-(2-pyrrolo[2,3-b]pyridin-1-ylethoxy)phenyl]methyl]propanedioate Chemical compound C1=CC(CC(C(=O)OC)C(=O)OC)=CC=C1OCCN1C2=NC=CC=C2C=C1 DGTTVPRXEKLDPR-UHFFFAOYSA-N 0.000 claims 1
- UKTBBMUEIHEGHI-UHFFFAOYSA-N dimethyl 2-[[4-[2-[6-(2-chlorobenzoyl)-2-oxo-1,3-benzothiazol-3-yl]ethoxy]phenyl]methyl]propanedioate Chemical compound C1=CC(CC(C(=O)OC)C(=O)OC)=CC=C1OCCN1C(=O)SC2=CC(C(=O)C=3C(=CC=CC=3)Cl)=CC=C21 UKTBBMUEIHEGHI-UHFFFAOYSA-N 0.000 claims 1
- ZGIWWDNJANAOIU-UHFFFAOYSA-N dimethyl 2-[[4-[2-[6-(4-methoxybenzoyl)-2-oxo-1,3-benzothiazol-3-yl]ethoxy]phenyl]methyl]propanedioate Chemical compound C1=CC(CC(C(=O)OC)C(=O)OC)=CC=C1OCCN1C(=O)SC2=CC(C(=O)C=3C=CC(OC)=CC=3)=CC=C21 ZGIWWDNJANAOIU-UHFFFAOYSA-N 0.000 claims 1
- HMQODXZQFCSRPI-UHFFFAOYSA-N dimethyl 2-[[4-[2-[6-[hydroxy(phenyl)methyl]-2-oxo-1,3-benzoxazol-3-yl]ethoxy]phenyl]methyl]propanedioate Chemical compound C1=CC(CC(C(=O)OC)C(=O)OC)=CC=C1OCCN1C(=O)OC2=CC(C(O)C=3C=CC=CC=3)=CC=C21 HMQODXZQFCSRPI-UHFFFAOYSA-N 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 210000002889 endothelial cell Anatomy 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000003893 regulation of appetite Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 230000000694 effects Effects 0.000 description 5
- 230000002218 hypoglycaemic effect Effects 0.000 description 5
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940123464 Thiazolidinedione Drugs 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000055 hyoplipidemic effect Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 125000000676 alkoxyimino group Chemical group 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 210000000229 preadipocyte Anatomy 0.000 description 2
- 229960004586 rosiglitazone Drugs 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 150000001467 thiazolidinediones Chemical class 0.000 description 2
- 102000003706 Complement factor D Human genes 0.000 description 1
- 108090000059 Complement factor D Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108010016731 PPAR gamma Proteins 0.000 description 1
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 1
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 1
- 108091006300 SLC2A4 Proteins 0.000 description 1
- 102100033939 Solute carrier family 2, facilitated glucose transporter member 4 Human genes 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 125000006307 alkoxy benzyl group Chemical group 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 125000006331 halo benzoyl group Chemical group 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P13/00—Drugs for disorders of the urinary 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Hematology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
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- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
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- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0001289A FR2804431A1 (fr) | 2000-02-02 | 2000-02-02 | Nouveaux derives heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200205599B true ZA200205599B (en) | 2003-12-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200205599A ZA200205599B (en) | 2000-02-02 | 2002-07-12 | Heterocyclic derivatives, preparation method and pharmaceutical compositions containing same. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6919362B2 (es) |
| EP (1) | EP1252150B1 (es) |
| JP (1) | JP2003521541A (es) |
| KR (1) | KR100495365B1 (es) |
| CN (1) | CN1211374C (es) |
| AR (1) | AR030048A1 (es) |
| AT (1) | ATE242223T1 (es) |
| AU (1) | AU775281B2 (es) |
| BR (1) | BR0108046A (es) |
| CA (1) | CA2398674A1 (es) |
| CZ (1) | CZ20022646A3 (es) |
| DE (1) | DE60100335T2 (es) |
| DK (1) | DK1252150T3 (es) |
| EA (1) | EA004676B1 (es) |
| ES (1) | ES2201029T3 (es) |
| FR (1) | FR2804431A1 (es) |
| HK (1) | HK1052007A1 (es) |
| HU (1) | HUP0204354A3 (es) |
| MX (1) | MXPA02007402A (es) |
| NO (1) | NO20023662L (es) |
| NZ (1) | NZ520260A (es) |
| PL (1) | PL356911A1 (es) |
| PT (1) | PT1252150E (es) |
| SK (1) | SK11162002A3 (es) |
| WO (1) | WO2001057002A1 (es) |
| ZA (1) | ZA200205599B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2845601B1 (fr) * | 2002-10-11 | 2005-07-08 | Servier Lab | Nouvelle association entre un compose heterocyclique et un agent antioxydant et les compositions pharmaceutiques qui les contiennent |
| FR2845998A1 (fr) * | 2002-10-18 | 2004-04-23 | Servier Lab | Nouveaux composes benzoxazoles ou oxazolopyridines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US7129264B2 (en) * | 2003-04-16 | 2006-10-31 | Bristol-Myers Squibb Company | Biarylmethyl indolines and indoles as antithromboembolic agents |
| US20050004133A1 (en) * | 2003-06-05 | 2005-01-06 | Makings Lewis R. | Modulators of VR1 receptor |
| FR2858321B1 (fr) * | 2003-07-28 | 2006-01-20 | Servier Lab | Nouveaux derives d'oximes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2868313B1 (fr) * | 2004-03-31 | 2008-08-15 | Servier Lab | Nouvelle association entre un compose heterocyclique et un agent antioxydant et les compositions pharmaceutiques qui les contiennent |
| FR2881137B1 (fr) * | 2005-01-27 | 2007-03-02 | Servier Lab | Nouveaux derives d'oximes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE102005026808A1 (de) | 2005-06-09 | 2006-12-14 | Sanofi-Aventis Deutschland Gmbh | Benzooxazol-2-on-derivate als Inhibitoren von Lipasen und Phospholipasen |
| FR2894965B1 (fr) * | 2005-12-20 | 2008-01-25 | Servier Lab | Nouveaux derives d'oximes heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2898125B1 (fr) * | 2006-03-06 | 2008-06-13 | Servier Lab | Nouveaux derives heterocycliques cycloalkyles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2903404B1 (fr) * | 2006-07-10 | 2008-08-22 | Servier Lab | Nouveaux derives tetracycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| ZA200902382B (en) | 2006-10-19 | 2010-08-25 | Signal Pharm Llc | Heteroaryl compounds, compositions thereof, and their use as protein kinase inhibitors |
| US20100158829A1 (en) * | 2008-12-24 | 2010-06-24 | Conopco, Inc., D/B/A Unilever | Method and Composition for Color Modulation |
| DE102009012314A1 (de) | 2009-03-09 | 2010-09-16 | Bayer Schering Pharma Aktiengesellschaft | Oxo-heterocyclisch substituierte Alkylcarbonsäuren und ihre Verwendung |
| CN105073728A (zh) | 2013-03-15 | 2015-11-18 | 全球血液疗法股份有限公司 | 化合物及其用于调节血红蛋白的用途 |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4116090A1 (de) * | 1991-05-17 | 1992-11-19 | Basf Ag | (alpha)-phenylacrylsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von schaedlingen und schadpilzen |
| DE19546918A1 (de) * | 1995-12-15 | 1997-06-19 | Bayer Ag | Bicyclische Heterocyclen |
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2000
- 2000-02-02 FR FR0001289A patent/FR2804431A1/fr active Pending
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2001
- 2001-02-01 NZ NZ520260A patent/NZ520260A/en unknown
- 2001-02-01 AT AT01904021T patent/ATE242223T1/de not_active IP Right Cessation
- 2001-02-01 ES ES01904021T patent/ES2201029T3/es not_active Expired - Lifetime
- 2001-02-01 KR KR10-2002-7009942A patent/KR100495365B1/ko not_active IP Right Cessation
- 2001-02-01 PT PT01904021T patent/PT1252150E/pt unknown
- 2001-02-01 MX MXPA02007402A patent/MXPA02007402A/es active IP Right Grant
- 2001-02-01 WO PCT/FR2001/000304 patent/WO2001057002A1/fr active IP Right Grant
- 2001-02-01 JP JP2001556852A patent/JP2003521541A/ja active Pending
- 2001-02-01 DE DE60100335T patent/DE60100335T2/de not_active Expired - Fee Related
- 2001-02-01 CN CNB018043399A patent/CN1211374C/zh not_active Expired - Fee Related
- 2001-02-01 SK SK1116-2002A patent/SK11162002A3/sk unknown
- 2001-02-01 PL PL01356911A patent/PL356911A1/xx not_active Application Discontinuation
- 2001-02-01 HU HU0204354A patent/HUP0204354A3/hu unknown
- 2001-02-01 US US10/203,113 patent/US6919362B2/en not_active Expired - Fee Related
- 2001-02-01 CA CA002398674A patent/CA2398674A1/fr not_active Abandoned
- 2001-02-01 EA EA200200810A patent/EA004676B1/ru not_active IP Right Cessation
- 2001-02-01 BR BR0108046-6A patent/BR0108046A/pt not_active IP Right Cessation
- 2001-02-01 DK DK01904021T patent/DK1252150T3/da active
- 2001-02-01 CZ CZ20022646A patent/CZ20022646A3/cs unknown
- 2001-02-01 AU AU31953/01A patent/AU775281B2/en not_active Ceased
- 2001-02-01 EP EP01904021A patent/EP1252150B1/fr not_active Expired - Lifetime
- 2001-02-02 AR ARP010100496A patent/AR030048A1/es unknown
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2002
- 2002-07-12 ZA ZA200205599A patent/ZA200205599B/en unknown
- 2002-08-01 NO NO20023662A patent/NO20023662L/no unknown
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2003
- 2003-06-16 HK HK03104267A patent/HK1052007A1/xx not_active IP Right Cessation
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