HRP20120424T1 - Derivati ureje, postupci za njihovu proizvodnju i njihova uporaba - Google Patents
Derivati ureje, postupci za njihovu proizvodnju i njihova uporaba Download PDFInfo
- Publication number
- HRP20120424T1 HRP20120424T1 HRP20120424TT HRP20120424T HRP20120424T1 HR P20120424 T1 HRP20120424 T1 HR P20120424T1 HR P20120424T T HRP20120424T T HR P20120424TT HR P20120424 T HRP20120424 T HR P20120424T HR P20120424 T1 HRP20120424 T1 HR P20120424T1
- Authority
- HR
- Croatia
- Prior art keywords
- groups
- group
- compound according
- ylethyl
- morpholin
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims 12
- 238000000034 method Methods 0.000 title 1
- 150000003672 ureas Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 40
- 125000001424 substituent group Chemical group 0.000 claims abstract 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 12
- -1 trifluoromethoxyl Chemical group 0.000 claims abstract 12
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 9
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 9
- 229910052717 sulfur Chemical group 0.000 claims abstract 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract 8
- 125000005843 halogen group Chemical group 0.000 claims abstract 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract 7
- 125000003118 aryl group Chemical group 0.000 claims abstract 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 6
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract 6
- 150000003462 sulfoxides Chemical class 0.000 claims abstract 6
- 239000011593 sulfur Chemical group 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- 239000001301 oxygen Substances 0.000 claims abstract 5
- 150000003457 sulfones Chemical group 0.000 claims abstract 5
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003172 aldehyde group Chemical group 0.000 claims abstract 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract 3
- 125000005020 hydroxyalkenyl group Chemical group 0.000 claims abstract 3
- 125000005016 hydroxyalkynyl group Chemical group 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
- 125000006413 ring segment Chemical group 0.000 claims abstract 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 11
- 125000003282 alkyl amino group Chemical group 0.000 claims 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 229940079593 drug Drugs 0.000 claims 8
- 230000002265 prevention Effects 0.000 claims 8
- 125000004442 acylamino group Chemical group 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 229940124530 sulfonamide Drugs 0.000 claims 5
- 150000003456 sulfonamides Chemical class 0.000 claims 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 5
- 125000003277 amino group Chemical group 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 3
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 3
- 239000004202 carbamide Substances 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 102000013830 Calcium-Sensing Receptors Human genes 0.000 claims 2
- 108010050543 Calcium-Sensing Receptors Proteins 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 229920001774 Perfluoroether Polymers 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 2
- 125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000001769 aryl amino group Chemical group 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 125000004986 diarylamino group Chemical group 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 210000002990 parathyroid gland Anatomy 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- OCOTWWSGPAHHQW-UHFFFAOYSA-N trifluoro(trifluoromethylsulfinyl)methane Chemical group FC(F)(F)S(=O)C(F)(F)F OCOTWWSGPAHHQW-UHFFFAOYSA-N 0.000 claims 2
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 2
- GHQBXJDIFWSBHM-UHFFFAOYSA-N 1-(2-morpholin-4-ylethyl)-1-(3-phenyl-3-pyridin-4-ylpropyl)-3-(4-phenyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC=CC=1C(C=1C=CN=CC=1)CCN(CCN1CCOCC1)C(=O)NC(SC=1)=NC=1C1=CC=CC=C1 GHQBXJDIFWSBHM-UHFFFAOYSA-N 0.000 claims 1
- NPNSOAQPRHIQCE-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)-3-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCN1CCOCC1)C(=O)NC(SC=1)=NC=1C1=CC=CC=N1 NPNSOAQPRHIQCE-UHFFFAOYSA-N 0.000 claims 1
- KGKGCIRNUKUTSM-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)-3-(4-pyridin-3-yl-2h-1,3-thiazol-3-yl)urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCN1CCOCC1)C(=O)NN1CSC=C1C1=CC=CN=C1 KGKGCIRNUKUTSM-UHFFFAOYSA-N 0.000 claims 1
- OKBTWRJXSAHHBA-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)-3-[4-(1,3-oxazol-2-yl)phenyl]urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCN1CCOCC1)C(=O)NC(C=C1)=CC=C1C1=NC=CO1 OKBTWRJXSAHHBA-UHFFFAOYSA-N 0.000 claims 1
- CSKYGKAVPJZAJT-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)-3-[4-(4-morpholin-4-ylphenyl)-1,3-thiazol-2-yl]urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCN1CCOCC1)C(=O)NC(SC=1)=NC=1C(C=C1)=CC=C1N1CCOCC1 CSKYGKAVPJZAJT-UHFFFAOYSA-N 0.000 claims 1
- IQIYMTRQCNWDRE-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)-3-[4-(4-pyrrolidin-1-ylphenyl)-1,3-thiazol-2-yl]urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCN1CCOCC1)C(=O)NC(SC=1)=NC=1C(C=C1)=CC=C1N1CCCC1 IQIYMTRQCNWDRE-UHFFFAOYSA-N 0.000 claims 1
- CIIJGMNXBMHIFX-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-(4-methoxy-1,3-benzothiazol-2-yl)-1-(2-morpholin-4-ylethyl)urea Chemical compound N=1C=2C(OC)=CC=CC=2SC=1NC(=O)N(CCN1CCOCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 CIIJGMNXBMHIFX-UHFFFAOYSA-N 0.000 claims 1
- NXNYLSJYKMJXBF-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-(4-phenyl-1,3-thiazol-2-yl)-1-(2-thiomorpholin-4-ylethyl)urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCN1CCSCC1)C(=O)NC(SC=1)=NC=1C1=CC=CC=C1 NXNYLSJYKMJXBF-UHFFFAOYSA-N 0.000 claims 1
- ZNTWXRLVCYUTBW-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-(5-methoxy-[1,3]thiazolo[5,4-b]pyridin-2-yl)-1-(2-morpholin-4-ylethyl)urea Chemical compound S1C2=NC(OC)=CC=C2N=C1NC(=O)N(CCN1CCOCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 ZNTWXRLVCYUTBW-UHFFFAOYSA-N 0.000 claims 1
- SNQLYBYKPJDMFL-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-(6-methoxy-1,3-benzothiazol-2-yl)-1-(2-morpholin-4-ylethyl)urea Chemical compound S1C2=CC(OC)=CC=C2N=C1NC(=O)N(CCN1CCOCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 SNQLYBYKPJDMFL-UHFFFAOYSA-N 0.000 claims 1
- QJUFVKLGQSTXTR-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-1-(2-morpholin-4-ylethyl)urea;dihydrochloride Chemical compound Cl.Cl.C1=CC(F)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN2CCOCC2)=N1 QJUFVKLGQSTXTR-UHFFFAOYSA-N 0.000 claims 1
- XEBXNYHWUYKCHS-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-1-(2-morpholin-4-ylethyl)urea Chemical compound C1=CC(OC)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN2CCOCC2)=N1 XEBXNYHWUYKCHS-UHFFFAOYSA-N 0.000 claims 1
- YIMABCZOADLIMV-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-(4-methylphenyl)-1,3-thiazol-2-yl]-1-(2-morpholin-4-ylethyl)urea Chemical compound C1=CC(C)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN2CCOCC2)=N1 YIMABCZOADLIMV-UHFFFAOYSA-N 0.000 claims 1
- ZYSCMWNXTDVXHM-UHFFFAOYSA-N 1-(3,3-diphenylpropyl)-3-[4-(4-methylsulfonylphenyl)-1,3-thiazol-2-yl]-1-(2-morpholin-4-ylethyl)urea Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN2CCOCC2)=N1 ZYSCMWNXTDVXHM-UHFFFAOYSA-N 0.000 claims 1
- PXARPBZBDSTBJI-UHFFFAOYSA-N 1-(3,3-dithiophen-2-ylpropyl)-1-(2-morpholin-4-ylethyl)-3-(4-phenyl-1,3-thiazol-2-yl)urea Chemical compound C=1C=CSC=1C(C=1SC=CC=1)CCN(CCN1CCOCC1)C(=O)NC(SC=1)=NC=1C1=CC=CC=C1 PXARPBZBDSTBJI-UHFFFAOYSA-N 0.000 claims 1
- DAOUFIPJJONZPB-UHFFFAOYSA-N 1-[2-(2,6-dimethylmorpholin-4-yl)ethyl]-1-(3,3-diphenylpropyl)-3-(4-phenyl-1,3-thiazol-2-yl)urea Chemical compound C1C(C)OC(C)CN1CCN(C(=O)NC=1SC=C(N=1)C=1C=CC=CC=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 DAOUFIPJJONZPB-UHFFFAOYSA-N 0.000 claims 1
- HBFJWJHDSCJHDZ-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-(2-morpholin-4-ylethyl)-1-(3-phenyl-3-pyridin-4-ylpropyl)urea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)N(CCN1CCOCC1)CCC(C=1C=CN=CC=1)C1=CC=CC=C1 HBFJWJHDSCJHDZ-UHFFFAOYSA-N 0.000 claims 1
- GCEKXNZJEPZBBC-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)N(CCN1CCOCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 GCEKXNZJEPZBBC-UHFFFAOYSA-N 0.000 claims 1
- XQBHEFGMHKTNSO-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-thiomorpholin-4-ylethyl)urea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)N(CCN1CCSCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 XQBHEFGMHKTNSO-UHFFFAOYSA-N 0.000 claims 1
- USDXAKHZJQKEEJ-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-(3,3-dithiophen-2-ylpropyl)-1-(2-morpholin-4-ylethyl)urea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)N(CCN1CCOCC1)CCC(C=1SC=CC=1)C1=CC=CS1 USDXAKHZJQKEEJ-UHFFFAOYSA-N 0.000 claims 1
- HWHZPANBXLRBMK-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1-[2-(2,6-dimethylmorpholin-4-yl)ethyl]-1-(3,3-diphenylpropyl)urea Chemical compound C1C(C)OC(C)CN1CCN(C(=O)NC=1SC2=CC=CC=C2N=1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 HWHZPANBXLRBMK-UHFFFAOYSA-N 0.000 claims 1
- SBRNTRWUMVKRJA-UHFFFAOYSA-N 3-(4-chloro-1,3-benzothiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea Chemical compound N=1C=2C(Cl)=CC=CC=2SC=1NC(=O)N(CCN1CCOCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 SBRNTRWUMVKRJA-UHFFFAOYSA-N 0.000 claims 1
- RZJOMVBTCBDARA-UHFFFAOYSA-N 3-(6-chloro-1,3-benzothiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea Chemical compound S1C2=CC(Cl)=CC=C2N=C1NC(=O)N(CCN1CCOCC1)CCC(C=1C=CC=CC=1)C1=CC=CC=C1 RZJOMVBTCBDARA-UHFFFAOYSA-N 0.000 claims 1
- BPMBGMPTGOHFED-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea Chemical compound C1=CC(Cl)=CC=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN2CCOCC2)=N1 BPMBGMPTGOHFED-UHFFFAOYSA-N 0.000 claims 1
- BNHZLHHFLCFJEH-UHFFFAOYSA-N 3-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]-1-(3,3-diphenylpropyl)-1-(2-morpholin-4-ylethyl)urea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CCN(CCN1CCOCC1)C(=O)NC(SC=1)=NC=1C1=CC=C(C#N)C=C1 BNHZLHHFLCFJEH-UHFFFAOYSA-N 0.000 claims 1
- MZTSRUJZTGWDGB-UHFFFAOYSA-N 5-[2-[[3,3-diphenylpropyl(2-morpholin-4-ylethyl)carbamoyl]amino]-1,3-thiazol-4-yl]-1,2-oxazole-3-carboxylic acid Chemical compound O1N=C(C(=O)O)C=C1C1=CSC(NC(=O)N(CCC(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN2CCOCC2)=N1 MZTSRUJZTGWDGB-UHFFFAOYSA-N 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000037147 Hypercalcaemia Diseases 0.000 claims 1
- 201000002980 Hyperparathyroidism Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010062767 Hypophysitis Diseases 0.000 claims 1
- 208000015924 Lithiasis Diseases 0.000 claims 1
- 206010025476 Malabsorption Diseases 0.000 claims 1
- 208000029725 Metabolic bone disease Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000010191 Osteitis Deformans Diseases 0.000 claims 1
- 206010049088 Osteopenia Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000027868 Paget disease Diseases 0.000 claims 1
- 208000000821 Parathyroid Neoplasms Diseases 0.000 claims 1
- 206010033964 Parathyroid tumour benign Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 206010038478 Renal lithiasis Diseases 0.000 claims 1
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 claims 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims 1
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims 1
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims 1
- 125000005110 aryl thio group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 210000002449 bone cell Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 230000004094 calcium homeostasis Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 230000000148 hypercalcaemia Effects 0.000 claims 1
- 208000030915 hypercalcemia disease Diseases 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 210000003016 hypothalamus Anatomy 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 229910001410 inorganic ion Inorganic materials 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 230000008411 joint metabolism Effects 0.000 claims 1
- 210000003292 kidney cell Anatomy 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 208000027202 mammary Paget disease Diseases 0.000 claims 1
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 201000003686 parathyroid adenoma Diseases 0.000 claims 1
- 208000014643 parathyroid gland adenoma Diseases 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- 230000008560 physiological behavior Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 210000003635 pituitary gland Anatomy 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 210000002966 serum Anatomy 0.000 claims 1
- 210000004927 skin cell Anatomy 0.000 claims 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
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- Rheumatology (AREA)
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- Diabetes (AREA)
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- Cardiology (AREA)
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- Obesity (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Treating Waste Gases (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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FR0504360A FR2885129B1 (fr) | 2005-04-29 | 2005-04-29 | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
PCT/EP2006/004166 WO2006117211A2 (fr) | 2005-04-29 | 2006-04-24 | Derives d'uree, procedes pour leur fabrication et utilisations de ces derives |
Publications (1)
Publication Number | Publication Date |
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HRP20120424T1 true HRP20120424T1 (hr) | 2012-06-30 |
Family
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Family Applications (1)
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HRP20120424TT HRP20120424T1 (hr) | 2005-04-29 | 2012-05-17 | Derivati ureje, postupci za njihovu proizvodnju i njihova uporaba |
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US (2) | US8247412B2 (fr) |
EP (2) | EP1874765B1 (fr) |
JP (1) | JP4995189B2 (fr) |
KR (1) | KR20080003380A (fr) |
CN (1) | CN101238120A (fr) |
AR (1) | AR056991A1 (fr) |
AT (1) | ATE548368T1 (fr) |
AU (1) | AU2006243328B2 (fr) |
BR (1) | BRPI0611025A2 (fr) |
CA (1) | CA2605008A1 (fr) |
CR (1) | CR9469A (fr) |
CY (1) | CY1112960T1 (fr) |
DK (1) | DK1874765T3 (fr) |
EA (1) | EA200702375A1 (fr) |
ES (1) | ES2384052T3 (fr) |
FR (1) | FR2885129B1 (fr) |
HR (1) | HRP20120424T1 (fr) |
IL (1) | IL186854A0 (fr) |
NO (1) | NO20076145L (fr) |
PL (1) | PL1874765T3 (fr) |
PT (1) | PT1874765E (fr) |
TW (1) | TW200714598A (fr) |
UY (1) | UY29510A1 (fr) |
WO (1) | WO2006117211A2 (fr) |
ZA (1) | ZA200708871B (fr) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2885129B1 (fr) | 2005-04-29 | 2007-06-15 | Proskelia Sas | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
US7875609B2 (en) | 2005-11-25 | 2011-01-25 | Galapagos Sasu | Urea derivatives, processes for their preparation, their use as medicaments, and pharmaceutical compositions containing them |
CA2648939C (fr) | 2006-04-20 | 2014-07-08 | Amgen Inc. | Formules d'emulsions stables |
GB0613674D0 (en) * | 2006-07-10 | 2006-08-16 | Proskelia Sas | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
AU2008233088B2 (en) | 2007-03-30 | 2013-09-26 | Amgen Inc. | Calcimimetic compounds for use in the treatment of bowel disorders |
JP5321452B2 (ja) * | 2007-05-08 | 2013-10-23 | 味の素株式会社 | 下痢の予防又は治療剤 |
AU2008275595B2 (en) * | 2007-07-10 | 2013-11-14 | Amgen Inc. | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
WO2010104882A1 (fr) | 2009-03-10 | 2010-09-16 | Amgen Inc. | Procédés de modulation de la motilité des spermatozoïdes |
WO2013138753A1 (fr) | 2012-03-16 | 2013-09-19 | Fox Chase Chemical Diversity Center, Inc. | Promédicaments de riluzole et leur méthode d'utilisation |
CN105492444B (zh) | 2013-07-02 | 2018-09-07 | 百时美施贵宝公司 | 作为rock抑制剂的三环吡啶-甲酰胺衍生物 |
JP6522602B2 (ja) | 2013-07-02 | 2019-05-29 | ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company | Rock阻害剤としての三環式ピリド−カルボキサミド誘導体 |
HUE058204T2 (hu) * | 2015-03-03 | 2022-07-28 | Biohaven Therapeutics Ltd | Riluzol prodrugok és felhasználásuk |
CN106946851B (zh) * | 2017-03-14 | 2019-11-12 | 牡丹江医学院 | 一种用于预防和治疗肾结石的药物 |
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JPS58109464A (ja) | 1981-12-23 | 1983-06-29 | Nippon Paint Co Ltd | アミノ酸化合物、その製法ならびに触媒 |
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FR2601363B1 (fr) * | 1986-07-08 | 1988-10-21 | Synthelabo | (dimethylamino)-2 ethyl) ((((methylthio)-2 phenyl) (phenylmethyl)amino)-2 oxo-2 ethyl) carbamates ou urees, leur preparation et leur application en therapeutique. |
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US5227397A (en) | 1989-04-28 | 1993-07-13 | Pfizer Inc. | Polyamines and polypeptides useful as antagonists of excitatory amino acid neuro-transmitters and/or as blockers of calcium channels |
DD298412A5 (de) | 1989-04-28 | 1992-02-20 | ������@���Kk�� | Verfahren zur herstellung von polypeptiden, die geeignet sind als antagonisten exzitatorischer aminosaeure-neurotransmitter und/oder blocker der calciumkanaele |
EP0597830A1 (fr) | 1989-07-03 | 1994-05-25 | New York University Nyu Medical Center | Emploi de polyamines en tant qu'agents regulateurs de canaux ioniques |
US5153226A (en) | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
DE69132423T2 (de) | 1990-11-19 | 2001-04-26 | Monsanto Co., St. Louis | Inhibitoren retroviraler Proteasen |
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EP0641333B1 (fr) | 1992-05-20 | 1996-08-14 | G.D. Searle & Co. | Procede de production d'intermediaires utiles dans la synthese d'inhibiteurs de proteases retrovirales |
DE69334250D1 (de) | 1992-12-29 | 2009-01-29 | Abbott Lab | Verfahren und Intermediate zur Herstellung von retroviralen Proteasehemmern |
JPH0841006A (ja) | 1994-08-05 | 1996-02-13 | Nisshin Flour Milling Co Ltd | ジウレア誘導体 |
PT1203761E (pt) | 1994-10-21 | 2005-04-29 | Nps Pharma Inc | Compostos activos do receptor de calcio |
ES2145929T3 (es) | 1994-11-04 | 2000-07-16 | Santen Pharmaceutical Co Ltd | Nuevo derivado de 1,3-dialquil-urea que tiene un grupo hidroxilo. |
EP0798291B1 (fr) | 1994-12-14 | 2002-09-11 | Santen Pharmaceutical Co., Ltd. | Nouveaux derives 1,3-dialkyluree |
JP3306571B2 (ja) | 1995-06-28 | 2002-07-24 | 参天製薬株式会社 | エンドセリン変換酵素阻害剤 |
JPH10195037A (ja) | 1996-02-15 | 1998-07-28 | Tanabe Seiyaku Co Ltd | フェノール誘導体 |
CA2197364A1 (fr) | 1996-02-15 | 1997-08-16 | Toshikazu Suzuki | Compose phenolique et methode de preparation |
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WO1999007672A1 (fr) | 1997-08-05 | 1999-02-18 | Novo Nordisk A/S | Derivees d'anilines 2,5- et 3,5-disubstituees, leur preparation et utilisation |
JPH11139969A (ja) | 1997-08-07 | 1999-05-25 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
CA2284864A1 (fr) | 1998-01-21 | 1999-07-29 | Zymogenetics, Inc. | Dialkylurees utilisees en tant que substances imitant la calcitonine |
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FR2809396B1 (fr) | 2000-05-24 | 2005-10-14 | Centre Nat Rech Scient | Nouvelles molecules possedant une activite calcimimetique et leur mode de preparation |
FR2812875B1 (fr) | 2000-08-08 | 2003-12-12 | Centre Nat Rech Scient | Nouvelles diamines possedant une activite modulatrice des casr et leur mode de preparation |
FR2820136A1 (fr) * | 2001-01-26 | 2002-08-02 | Aventis Pharma Sa | Nouveaux derives de l'uree, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation |
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JP2005336173A (ja) * | 2004-04-27 | 2005-12-08 | Santen Pharmaceut Co Ltd | 骨粗鬆症治療剤 |
EP1757582B1 (fr) | 2004-05-28 | 2015-12-30 | Mitsubishi Tanabe Pharma Corporation | Arylalkylamines et procédé pour la production de celles-ci |
FR2885129B1 (fr) | 2005-04-29 | 2007-06-15 | Proskelia Sas | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
EP1882684B1 (fr) | 2005-05-19 | 2014-12-10 | Astellas Pharma Inc. | Derive de pyrrolidine ou son sel |
US7875609B2 (en) | 2005-11-25 | 2011-01-25 | Galapagos Sasu | Urea derivatives, processes for their preparation, their use as medicaments, and pharmaceutical compositions containing them |
GB0613674D0 (en) | 2006-07-10 | 2006-08-16 | Proskelia Sas | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
AU2008275595B2 (en) | 2007-07-10 | 2013-11-14 | Amgen Inc. | Derivatives of urea and related diamines, methods for their manufacture, and uses therefor |
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2006
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- 2006-04-24 KR KR1020077024941A patent/KR20080003380A/ko not_active Application Discontinuation
- 2006-04-24 CA CA002605008A patent/CA2605008A1/fr not_active Abandoned
- 2006-04-24 WO PCT/EP2006/004166 patent/WO2006117211A2/fr active Application Filing
- 2006-04-24 PL PL06724709T patent/PL1874765T3/pl unknown
- 2006-04-24 PT PT06724709T patent/PT1874765E/pt unknown
- 2006-04-24 EP EP11002964A patent/EP2354137A1/fr not_active Withdrawn
- 2006-04-26 TW TW095114960A patent/TW200714598A/zh unknown
- 2006-04-26 AR ARP060101666A patent/AR056991A1/es unknown
- 2006-04-28 UY UY29510A patent/UY29510A1/es not_active Application Discontinuation
-
2007
- 2007-10-16 ZA ZA200708871A patent/ZA200708871B/xx unknown
- 2007-10-23 CR CR9469A patent/CR9469A/es unknown
- 2007-10-23 IL IL186854A patent/IL186854A0/en unknown
- 2007-11-28 NO NO20076145A patent/NO20076145L/no not_active Application Discontinuation
-
2012
- 2012-05-17 HR HRP20120424TT patent/HRP20120424T1/hr unknown
- 2012-06-06 CY CY20121100508T patent/CY1112960T1/el unknown
- 2012-06-27 US US13/535,198 patent/US20120283255A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
TW200714598A (en) | 2007-04-16 |
CR9469A (es) | 2008-03-06 |
ZA200708871B (en) | 2009-03-25 |
PL1874765T3 (pl) | 2012-08-31 |
JP2008539186A (ja) | 2008-11-13 |
UY29510A1 (es) | 2006-12-29 |
CA2605008A1 (fr) | 2006-11-09 |
JP4995189B2 (ja) | 2012-08-08 |
PT1874765E (pt) | 2012-05-25 |
CN101238120A (zh) | 2008-08-06 |
DK1874765T3 (da) | 2012-06-18 |
EP1874765B1 (fr) | 2012-03-07 |
AU2006243328A1 (en) | 2006-11-09 |
AU2006243328B2 (en) | 2011-09-08 |
FR2885129A1 (fr) | 2006-11-03 |
BRPI0611025A2 (pt) | 2016-11-16 |
EP1874765A2 (fr) | 2008-01-09 |
US20120283255A1 (en) | 2012-11-08 |
EA200702375A1 (ru) | 2008-06-30 |
US8247412B2 (en) | 2012-08-21 |
EP2354137A1 (fr) | 2011-08-10 |
KR20080003380A (ko) | 2008-01-07 |
NO20076145L (no) | 2008-01-28 |
ES2384052T3 (es) | 2012-06-28 |
ATE548368T1 (de) | 2012-03-15 |
FR2885129B1 (fr) | 2007-06-15 |
CY1112960T1 (el) | 2016-04-13 |
IL186854A0 (en) | 2008-02-09 |
US20100240889A1 (en) | 2010-09-23 |
AR056991A1 (es) | 2007-11-07 |
WO2006117211A2 (fr) | 2006-11-09 |
WO2006117211A3 (fr) | 2007-01-11 |
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