SK3542003A3 - Substituted cinnamic acid guanidides, method for the production thereof, their use as a medicament, and to a medicament containing these compounds - Google Patents
Substituted cinnamic acid guanidides, method for the production thereof, their use as a medicament, and to a medicament containing these compounds Download PDFInfo
- Publication number
- SK3542003A3 SK3542003A3 SK354-2003A SK3542003A SK3542003A3 SK 3542003 A3 SK3542003 A3 SK 3542003A3 SK 3542003 A SK3542003 A SK 3542003A SK 3542003 A3 SK3542003 A3 SK 3542003A3
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- SK
- Slovakia
- Prior art keywords
- alkyl
- carbon atoms
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 86
- 239000003814 drug Substances 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 18
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 title claims abstract description 14
- 229930016911 cinnamic acid Natural products 0.000 title claims abstract description 14
- 235000013985 cinnamic acid Nutrition 0.000 title claims abstract description 14
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 150000001851 cinnamic acid derivatives Chemical class 0.000 title claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 24
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 12
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 142
- 125000004432 carbon atom Chemical group C* 0.000 claims description 127
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 229910052731 fluorine Inorganic materials 0.000 claims description 45
- -1 CF 3 Chemical group 0.000 claims description 44
- 239000000460 chlorine Chemical group 0.000 claims description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 29
- 239000011737 fluorine Substances 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 22
- 229910005965 SO 2 Inorganic materials 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 16
- 230000002265 prevention Effects 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 210000000056 organ Anatomy 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 230000004663 cell proliferation Effects 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
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- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
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- 238000004321 preservation Methods 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 24
- 150000003840 hydrochlorides Chemical class 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 229960004198 guanidine Drugs 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- 239000000872 buffer Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 7
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- FPLCLZUJRYGQOJ-UHFFFAOYSA-N ethyl 3-(4-bromophenyl)-2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=CC1=CC=C(Br)C=C1 FPLCLZUJRYGQOJ-UHFFFAOYSA-N 0.000 description 6
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
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- IJDRABLXWHHVKE-UHFFFAOYSA-N ethyl 2-methyl-3-(3,4,5-trifluorophenyl)prop-2-enoate Chemical compound CCOC(=O)C(C)=CC1=CC(F)=C(F)C(F)=C1 IJDRABLXWHHVKE-UHFFFAOYSA-N 0.000 description 5
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- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 3
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- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
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- UOWKCYAYYSXICW-UHFFFAOYSA-N n'-(4-aminophenyl)sulfonyl-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NS(=O)(=O)C1=CC=C(N)C=C1 UOWKCYAYYSXICW-UHFFFAOYSA-N 0.000 description 1
- CZGIEJXGCLWRPY-UHFFFAOYSA-N n,1-dimethylpyrrolidin-3-amine Chemical compound CNC1CCN(C)C1 CZGIEJXGCLWRPY-UHFFFAOYSA-N 0.000 description 1
- QJEZJHOAVYGZHZ-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-3-[4-(3-sulfamoylanilino)phenyl]prop-2-enamide Chemical compound C1=CC(C=C(C)C(=O)NC(N)=N)=CC=C1NC1=CC=CC(S(N)(=O)=O)=C1 QJEZJHOAVYGZHZ-UHFFFAOYSA-N 0.000 description 1
- PCZPRSDSGGWUHY-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-3-[4-(4-sulfamoylanilino)phenyl]prop-2-enamide Chemical compound C1=CC(C=C(C)C(=O)NC(N)=N)=CC=C1NC1=CC=C(S(N)(=O)=O)C=C1 PCZPRSDSGGWUHY-UHFFFAOYSA-N 0.000 description 1
- YTNSEEPQLQBTIW-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-3-[4-[4-(2-pyrrolidin-1-ylethylsulfamoyl)anilino]phenyl]prop-2-enamide Chemical compound C1=CC(C=C(C)C(=O)NC(N)=N)=CC=C1NC1=CC=C(S(=O)(=O)NCCN2CCCC2)C=C1 YTNSEEPQLQBTIW-UHFFFAOYSA-N 0.000 description 1
- YMSODFQDTREZKR-UHFFFAOYSA-N n-(diaminomethylidene)-3-[3,5-difluoro-4-(4-sulfamoylphenoxy)phenyl]-2-methylprop-2-enamide Chemical compound FC1=CC(C=C(C)C(=O)NC(N)=N)=CC(F)=C1OC1=CC=C(S(N)(=O)=O)C=C1 YMSODFQDTREZKR-UHFFFAOYSA-N 0.000 description 1
- IZBWONXCHYOMTN-UHFFFAOYSA-N n-(diaminomethylidene)-3-[3,5-difluoro-4-[4-(4-methylpiperazin-1-yl)sulfonylphenoxy]phenyl]-2-methylprop-2-enamide Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1OC1=C(F)C=C(C=C(C)C(=O)NC(N)=N)C=C1F IZBWONXCHYOMTN-UHFFFAOYSA-N 0.000 description 1
- RVTUWUJGDFIPAV-UHFFFAOYSA-N n-(diaminomethylidene)-3-[4-[4-[2-(dimethylamino)ethylsulfamoyl]anilino]phenyl]-2-methylprop-2-enamide Chemical compound C1=CC(S(=O)(=O)NCCN(C)C)=CC=C1NC1=CC=C(C=C(C)C(=O)NC(N)=N)C=C1 RVTUWUJGDFIPAV-UHFFFAOYSA-N 0.000 description 1
- KDWJSOFECLQUFW-UHFFFAOYSA-N n-(diaminomethylidene)-3-[4-[4-[2-(dimethylamino)ethylsulfamoyl]phenoxy]-3,5-difluorophenyl]-2-methylprop-2-enamide Chemical compound C1=CC(S(=O)(=O)NCCN(C)C)=CC=C1OC1=C(F)C=C(C=C(C)C(=O)NC(N)=N)C=C1F KDWJSOFECLQUFW-UHFFFAOYSA-N 0.000 description 1
- MBONODFCCYMUHM-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-hydroxybenzenesulfonamide Chemical compound CN(C)CCNS(=O)(=O)C1=CC=C(O)C=C1 MBONODFCCYMUHM-UHFFFAOYSA-N 0.000 description 1
- PQYVJANTOAAMST-UHFFFAOYSA-N n-[4-(2-pyrrolidin-1-ylethylsulfamoyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NCCN1CCCC1 PQYVJANTOAAMST-UHFFFAOYSA-N 0.000 description 1
- FIFVSQIZNIIPJZ-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]acetamide Chemical compound C1CN(C)CCN1S(=O)(=O)C1=CC=C(NC(C)=O)C=C1 FIFVSQIZNIIPJZ-UHFFFAOYSA-N 0.000 description 1
- KPNNXMNEPHNUNR-UHFFFAOYSA-N n-[4-(methylsulfamoyl)phenyl]acetamide Chemical compound CNS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 KPNNXMNEPHNUNR-UHFFFAOYSA-N 0.000 description 1
- IWWPKDXSOQRWDH-UHFFFAOYSA-N n-[4-[2-(dimethylamino)ethylsulfamoyl]phenyl]acetamide Chemical compound CN(C)CCNS(=O)(=O)C1=CC=C(NC(C)=O)C=C1 IWWPKDXSOQRWDH-UHFFFAOYSA-N 0.000 description 1
- XOPAGNNTTQXBSO-UHFFFAOYSA-N n-[4-[methyl-(1-methylpyrrolidin-3-yl)sulfamoyl]phenyl]acetamide Chemical compound C=1C=C(NC(C)=O)C=CC=1S(=O)(=O)N(C)C1CCN(C)C1 XOPAGNNTTQXBSO-UHFFFAOYSA-N 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000035778 pathophysiological process Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000009117 preventive therapy Methods 0.000 description 1
- 208000037920 primary disease Diseases 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
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- 230000010410 reperfusion Effects 0.000 description 1
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- 239000003169 respiratory stimulant agent Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000037921 secondary disease Diseases 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000009441 vascular protection Effects 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/41—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10046993A DE10046993A1 (de) | 2000-09-22 | 2000-09-22 | Substituierte Zimtsäureguanidide, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltendes Medikament |
| PCT/EP2001/010375 WO2002024637A1 (de) | 2000-09-22 | 2001-09-08 | Substituierte zimtsäureguanidide, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK3542003A3 true SK3542003A3 (en) | 2003-09-11 |
Family
ID=7657232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK354-2003A SK3542003A3 (en) | 2000-09-22 | 2001-09-08 | Substituted cinnamic acid guanidides, method for the production thereof, their use as a medicament, and to a medicament containing these compounds |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6399824B1 (no) |
| EP (1) | EP1322602A1 (no) |
| JP (1) | JP2004509163A (no) |
| KR (1) | KR20030094210A (no) |
| CN (1) | CN1462268A (no) |
| AR (1) | AR030947A1 (no) |
| AU (1) | AU2001293802A1 (no) |
| BR (1) | BR0114092A (no) |
| CA (1) | CA2422709A1 (no) |
| CZ (1) | CZ2003815A3 (no) |
| DE (1) | DE10046993A1 (no) |
| EE (1) | EE200300110A (no) |
| HU (1) | HUP0303699A3 (no) |
| IL (1) | IL154953A0 (no) |
| MX (1) | MXPA03002309A (no) |
| NO (1) | NO20031273L (no) |
| PL (1) | PL360993A1 (no) |
| RU (1) | RU2003111462A (no) |
| SK (1) | SK3542003A3 (no) |
| WO (1) | WO2002024637A1 (no) |
| ZA (1) | ZA200301778B (no) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE336496T1 (de) | 2002-04-15 | 2006-09-15 | Janssen Pharmaceutica Nv | Farnesyl transferase hemmende tricyclische quinazolinederivate substitutiert mit kohlenstoff-gebundenen imidazolen oder triazolen |
| FR2840302B1 (fr) * | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | Derives d'isoindolones, procede de preparation et intermediaire de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| ATE423121T1 (de) | 2004-06-16 | 2009-03-15 | Wyeth Corp | Diphenylimidazopyrimidin- und -imidazolamine als b-sekretase-inhibitoren |
| ES2332659T3 (es) * | 2004-06-16 | 2010-02-10 | Wyeth | Derivados de amino-5,5-difenilimidazolona para la inhibicion de beta-secretasa. |
| CN101103034A (zh) * | 2005-01-14 | 2008-01-09 | 惠氏公司 | 抑制β-分泌酶的氨基-咪唑酮 |
| MX2007009313A (es) * | 2005-02-01 | 2007-09-12 | Wyeth Corp | Amino-piridinas como inhibidores de ????-secretasa. |
| BRPI0606902A2 (pt) | 2005-02-14 | 2009-07-28 | Wyeth Corp | composto; método para o tratamento de uma doença ou distúrbio associado a atividade excessiva de bace em um paciente que dele necessite; método para modular a atividade de bace; composição farmacêutica |
| WO2006088705A1 (en) * | 2005-02-14 | 2006-08-24 | Wyeth | Terphenyl guanidines as [beta symbol] -secretase inhibitors |
| EP1896448A1 (en) * | 2005-06-30 | 2008-03-12 | Wyeth | AMINO-5-(6-MEMBERED)HETEROARYLIMIDAZOLONE COMPOUNDS AND THE USE THEREOF FOR ß-SECRETASE MODULATION |
| TW200738683A (en) * | 2005-06-30 | 2007-10-16 | Wyeth Corp | Amino-5-(5-membered)heteroarylimidazolone compounds and the use thereof for β-secretase modulation |
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| AU2018205400C1 (en) | 2017-01-09 | 2026-01-15 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19502795A1 (de) * | 1995-01-30 | 1996-08-01 | Hoechst Ag | Benzolsulfonamid-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE59603311D1 (de) * | 1995-01-30 | 1999-11-18 | Hoechst Ag | Basisch-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US6057322A (en) | 1995-01-30 | 2000-05-02 | Hoechst Aktiengesellschaft | Basically-substituted benzoylguanidines, a process for preparing them, their use as a medicament or diagnostic agent, and a medicament containing them |
| DE19518796A1 (de) * | 1995-05-22 | 1996-11-28 | Hoechst Ag | Fluorphenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19527305A1 (de) * | 1995-07-26 | 1997-01-30 | Hoechst Ag | Substituierte Zimtsäureguanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19633966A1 (de) | 1996-08-22 | 1998-02-26 | Hoechst Ag | Phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
2000
- 2000-09-22 DE DE10046993A patent/DE10046993A1/de not_active Withdrawn
-
2001
- 2001-09-08 CA CA002422709A patent/CA2422709A1/en not_active Abandoned
- 2001-09-08 EE EEP200300110A patent/EE200300110A/xx unknown
- 2001-09-08 MX MXPA03002309A patent/MXPA03002309A/es unknown
- 2001-09-08 RU RU2003111462/04A patent/RU2003111462A/ru not_active Application Discontinuation
- 2001-09-08 CZ CZ2003815A patent/CZ2003815A3/cs unknown
- 2001-09-08 EP EP01974235A patent/EP1322602A1/de not_active Withdrawn
- 2001-09-08 IL IL15495301A patent/IL154953A0/xx unknown
- 2001-09-08 BR BR0114092-2A patent/BR0114092A/pt not_active IP Right Cessation
- 2001-09-08 JP JP2002529050A patent/JP2004509163A/ja not_active Withdrawn
- 2001-09-08 WO PCT/EP2001/010375 patent/WO2002024637A1/de not_active Ceased
- 2001-09-08 KR KR10-2003-7004159A patent/KR20030094210A/ko not_active Withdrawn
- 2001-09-08 CN CN01816055A patent/CN1462268A/zh active Pending
- 2001-09-08 PL PL36099301A patent/PL360993A1/xx not_active Application Discontinuation
- 2001-09-08 HU HU0303699A patent/HUP0303699A3/hu unknown
- 2001-09-08 AU AU2001293802A patent/AU2001293802A1/en not_active Abandoned
- 2001-09-08 SK SK354-2003A patent/SK3542003A3/sk unknown
- 2001-09-18 US US09/954,016 patent/US6399824B1/en not_active Expired - Fee Related
- 2001-09-20 AR ARP010104445A patent/AR030947A1/es not_active Application Discontinuation
-
2003
- 2003-03-04 ZA ZA200301778A patent/ZA200301778B/en unknown
- 2003-03-19 NO NO20031273A patent/NO20031273L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2003111462A (ru) | 2004-11-10 |
| MXPA03002309A (es) | 2003-06-06 |
| CA2422709A1 (en) | 2003-03-18 |
| JP2004509163A (ja) | 2004-03-25 |
| HUP0303699A2 (hu) | 2004-04-28 |
| AR030947A1 (es) | 2003-09-03 |
| WO2002024637A1 (de) | 2002-03-28 |
| BR0114092A (pt) | 2003-09-09 |
| DE10046993A1 (de) | 2002-04-11 |
| KR20030094210A (ko) | 2003-12-11 |
| NO20031273L (no) | 2003-05-14 |
| CZ2003815A3 (cs) | 2003-06-18 |
| PL360993A1 (en) | 2004-09-20 |
| US6399824B1 (en) | 2002-06-04 |
| AU2001293802A1 (en) | 2002-04-02 |
| EP1322602A1 (de) | 2003-07-02 |
| CN1462268A (zh) | 2003-12-17 |
| ZA200301778B (en) | 2004-04-16 |
| EE200300110A (et) | 2005-04-15 |
| HUP0303699A3 (en) | 2006-02-28 |
| NO20031273D0 (no) | 2003-03-19 |
| IL154953A0 (en) | 2003-10-31 |
| US20020058710A1 (en) | 2002-05-16 |
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