ZA200501455B - 2-thio-substituted imidazole derivatives and their use in pharmaceutics - Google Patents

2-thio-substituted imidazole derivatives and their use in pharmaceutics Download PDF

Info

Publication number: ZA200501455B
Authority: ZA; South Africa
Prior art keywords: alkyl; compound; phenyl; group; formula
Prior art date: 2002-08-20

Application number

ZA200501455A

Other languages

English (en)

Inventor

Laufer Stefan

Hans-Guenter Striegel

Tollmann Karola

Albrecht Wolfgang

Original Assignee

Merckle Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-08-20

Filing date

2005-02-18

Publication date

2006-10-25

2005-02-18 Application filed by Merckle Gmbh filed Critical Merckle Gmbh

2006-10-25 Publication of ZA200501455B publication Critical patent/ZA200501455B/en

Links

150000002460 imidazoles Chemical class 0.000 title claims description 14
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims description 39
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
-1 alkyl radical Chemical class 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 25
150000002367 halogens Chemical class 0.000 claims description 25
150000003254 radicals Chemical class 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
102000004127 Cytokines Human genes 0.000 claims description 8
108090000695 Cytokines Proteins 0.000 claims description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000005842 heteroatom Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
150000005840 aryl radicals Chemical class 0.000 claims description 3
230000002519 immonomodulatory effect Effects 0.000 claims description 3
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000000165 tricyclic carbocycle group Chemical group 0.000 claims description 2
210000000987 immune system Anatomy 0.000 claims 3
239000000203 mixture Substances 0.000 claims 3
101000723740 Homo sapiens Zinc finger protein 24 Proteins 0.000 claims 1
101150088095 RTM2 gene Proteins 0.000 claims 1
102100028365 Zinc finger protein 24 Human genes 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000000460 chlorine Substances 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 8
230000003110 anti-inflammatory effect Effects 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical class S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002971 oxazolyl group Chemical group 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical group CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 1
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
102000004357 Transferases Human genes 0.000 description 1
108090000992 Transferases Proteins 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000000326 anti-hypercholesterolaemic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000005516 coenzyme A Substances 0.000 description 1
229940093530 coenzyme a Drugs 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229960000443 hydrochloric acid Drugs 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
230000002757 inflammatory effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052740 iodine Inorganic materials 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
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002757 morpholinyl 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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 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
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
125000004660 phenylalkylthio group Chemical group 0.000 description 1
OTYNBGDFCPCPOU-UHFFFAOYSA-N phosphane sulfane Chemical compound S.P[H] OTYNBGDFCPCPOU-UHFFFAOYSA-N 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- 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
- A61P1/16—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
- 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
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- 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
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ZA200501455A 2002-08-20 2005-02-18 2-thio-substituted imidazole derivatives and their use in pharmaceutics ZA200501455B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE10238045A DE10238045A1 (de)	2002-08-20	2002-08-20	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie

Publications (1)

Publication Number	Publication Date
ZA200501455B true ZA200501455B (en)	2006-10-25

Family

ID=31197117

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200501455A ZA200501455B (en)	2002-08-20	2005-02-18	2-thio-substituted imidazole derivatives and their use in pharmaceutics

Country Status (19)

Country	Link
US (1)	US7582660B2 (is)
EP (1)	EP1539741A1 (is)
JP (1)	JP2005539035A (is)
KR (1)	KR20050058419A (is)
CN (1)	CN100396677C (is)
AU (1)	AU2003267000B2 (is)
BR (1)	BR0313277A (is)
CA (1)	CA2501849A1 (is)
DE (1)	DE10238045A1 (is)
HR (1)	HRP20050239A2 (is)
IS (1)	IS7740A (is)
MX (1)	MXPA05001985A (is)
NO (1)	NO20051477L (is)
PL (1)	PL375793A1 (is)
RS (1)	RS20050131A (is)
RU (1)	RU2331638C2 (is)
UA (1)	UA80718C2 (is)
WO (1)	WO2004018458A1 (is)
ZA (1)	ZA200501455B (is)

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AU2006218037B2 (en) *	2005-02-28	2012-04-05	Merckle Gmbh	2-sulfinyl- and 2-sulfonyl-substituted imidazole derivatives and their use as cytokine inhibitors
EP1894925A1 (en) *	2006-08-24	2008-03-05	Merckle Gmbh	Imidazole compounds having an antiinflammatory effect
US8143294B2 (en) *	2007-12-31	2012-03-27	Michael Burnet	2-sulfanyl-substituted imidazole derivatives and their use as cytokine inhibitors
JP5912946B2 (ja) *	2012-01-11	2016-04-27	株式会社Adeka	感光性樹脂組成物
WO2022067063A1 (en) *	2020-09-25	2022-03-31	Dana-Farber Cancer Institute, Inc.	Mutant selective egfr inhibitors and methods of use thereof

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SU1415725A1 (ru)	1986-11-17	1996-10-10	В.М. Виноградов	Дигидрохлорид 4-(4'-метоксифенил)-2-морфолиноэтилтио-5-фенилимидазола, повышающий физическую выносливость
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US5364875A (en)	1992-05-11	1994-11-15	The Du Pont Merck Pharmaceutical Company	Imidazoles linked to bicyclic heterocyclic groups for the treatment of atherosclerosis
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DE10107683A1 (de)	2001-02-19	2002-08-29	Merckle Gmbh Chem Pharm Fabrik	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie
DE10114775A1 (de)	2001-03-26	2002-10-10	Gerhard Dannhardt	2-Mercapto-4,5-diarylimidazolderivate und ihre Verwendung in der Pharmazie
DE10222103A1 (de)	2002-05-17	2003-11-27	Merckle Gmbh Chem Pharm Fabrik	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie

2002
- 2002-08-20 DE DE10238045A patent/DE10238045A1/de not_active Withdrawn
2003
- 2003-08-20 HR HR20050239A patent/HRP20050239A2/hr not_active Application Discontinuation
- 2003-08-20 CN CNB038197502A patent/CN100396677C/zh not_active Expired - Fee Related
- 2003-08-20 JP JP2004530221A patent/JP2005539035A/ja active Pending
- 2003-08-20 EP EP03747916A patent/EP1539741A1/de not_active Withdrawn
- 2003-08-20 MX MXPA05001985A patent/MXPA05001985A/es active IP Right Grant
- 2003-08-20 PL PL03375793A patent/PL375793A1/xx not_active Application Discontinuation
- 2003-08-20 KR KR1020057002947A patent/KR20050058419A/ko not_active Ceased
- 2003-08-20 RU RU2005107726/04A patent/RU2331638C2/ru not_active IP Right Cessation
- 2003-08-20 CA CA002501849A patent/CA2501849A1/en not_active Abandoned
- 2003-08-20 UA UAA200502484A patent/UA80718C2/uk unknown
- 2003-08-20 WO PCT/EP2003/009219 patent/WO2004018458A1/de not_active Ceased
- 2003-08-20 BR BR0313277-3A patent/BR0313277A/pt not_active IP Right Cessation
- 2003-08-20 AU AU2003267000A patent/AU2003267000B2/en not_active Ceased
- 2003-08-20 US US10/524,486 patent/US7582660B2/en not_active Expired - Fee Related
- 2003-08-20 RS YUP-2005/0131A patent/RS20050131A/sr unknown
2005
- 2005-02-18 ZA ZA200501455A patent/ZA200501455B/en unknown
- 2005-03-14 IS IS7740A patent/IS7740A/is unknown
- 2005-03-18 NO NO20051477A patent/NO20051477L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
HRP20050239A2 (en)	2005-10-31
AU2003267000A1 (en)	2004-03-11
WO2004018458A1 (de)	2004-03-04
IS7740A (is)	2005-03-14
RS20050131A (sr)	2007-06-04
US20060235054A1 (en)	2006-10-19
UA80718C2 (en)	2007-10-25
CN100396677C (zh)	2008-06-25
CN1675197A (zh)	2005-09-28
AU2003267000B2 (en)	2009-05-28
BR0313277A (pt)	2005-06-21
RU2005107726A (ru)	2006-01-20
JP2005539035A (ja)	2005-12-22
MXPA05001985A (es)	2005-05-27
KR20050058419A (ko)	2005-06-16
DE10238045A1 (de)	2004-03-04
CA2501849A1 (en)	2004-03-04
EP1539741A1 (de)	2005-06-15
RU2331638C2 (ru)	2008-08-20
US7582660B2 (en)	2009-09-01
NO20051477L (no)	2005-05-19
PL375793A1 (en)	2005-12-12

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JPH01100160A (ja)	1989-04-18	新規なドパミンベ−タヒドロキシラ−ゼ抑制剤
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ZA200501455B (en)	2006-10-25	2-thio-substituted imidazole derivatives and their use in pharmaceutics
CA2626402A1 (en)	2007-05-03	Potassium channel inhibitors
AU2006227032B2 (en)	2010-02-25	Substituted sulfoxide compounds, methods for preparing the same and use thereof
DE60216610D1 (de)	2007-01-18	Verwendung von kondensierten Pyrazolverbindungen für die Herstellung eines Arzneimittels zur Behandlung von Bluthochdruck