SK5222001A3 - Substituted phenyl derivatives, their preparation and use - Google Patents

Substituted phenyl derivatives, their preparation and use Download PDF

Info

Publication number: SK5222001A3
Authority: SK; Slovakia
Prior art keywords: urea; phenyl; tetrazol; bromo; trifluoromethylphenyl
Prior art date: 1998-10-22

Application number

SK522-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Bjarne H Dahl

Palle Christophersen

Original Assignee

Neurosearch As

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.)

1998-10-22

Filing date

1999-10-19

Publication date

2002-05-09

1999-10-19 Application filed by Neurosearch As filed Critical Neurosearch As

2002-05-09 Publication of SK5222001A3 publication Critical patent/SK5222001A3/sk

Links

125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 125
238000002360 preparation method Methods 0.000 title claims description 21
150000001875 compounds Chemical class 0.000 claims abstract description 118
125000000217 alkyl group Chemical group 0.000 claims abstract description 43
108010062745 Chloride Channels Proteins 0.000 claims abstract description 27
102000011045 Chloride Channels Human genes 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 21
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
125000000524 functional group Chemical group 0.000 claims abstract description 4
230000002378 acidificating effect Effects 0.000 claims abstract description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 234
-1 phenylamino, phenoxy Chemical group 0.000 claims description 172
239000004202 carbamide Substances 0.000 claims description 142
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
201000010099 disease Diseases 0.000 claims description 35
210000002997 osteoclast Anatomy 0.000 claims description 31
238000011282 treatment Methods 0.000 claims description 30
210000000988 bone and bone Anatomy 0.000 claims description 25
125000005842 heteroatom Chemical group 0.000 claims description 24
235000005881 Calendula officinalis Nutrition 0.000 claims description 23
238000000034 method Methods 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 22
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 21
208000007502 anemia Diseases 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 20
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 17
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 15
208000035475 disorder Diseases 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
206010048962 Brain oedema Diseases 0.000 claims description 10
208000010412 Glaucoma Diseases 0.000 claims description 10
241001465754 Metazoa Species 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 10
208000006752 brain edema Diseases 0.000 claims description 10
239000002934 diuretic Substances 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
206010012735 Diarrhoea Diseases 0.000 claims description 9
206010020772 Hypertension Diseases 0.000 claims description 9
230000001882 diuretic effect Effects 0.000 claims description 9
208000028867 ischemia Diseases 0.000 claims description 9
208000029725 Metabolic bone disease Diseases 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
208000030159 metabolic disease Diseases 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
125000003831 tetrazolyl group Chemical group 0.000 claims description 6
230000004097 bone metabolism Effects 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
230000000172 allergic effect Effects 0.000 claims description 4
208000010668 atopic eczema Diseases 0.000 claims description 4
239000004305 biphenyl Substances 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
230000004968 inflammatory condition Effects 0.000 claims description 4
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
RIWIYKPEDBYULV-UHFFFAOYSA-N 1-(3-bromophenyl)-3-(2,3-difluorophenyl)urea Chemical compound FC1=CC=CC(NC(=O)NC=2C=C(Br)C=CC=2)=C1F RIWIYKPEDBYULV-UHFFFAOYSA-N 0.000 claims description 3
RQPVXOUSZLDZFI-UHFFFAOYSA-N 2-(phenylcarbamoylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC(=O)NC1=CC=CC=C1 RQPVXOUSZLDZFI-UHFFFAOYSA-N 0.000 claims description 3
125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
208000025865 Ulcer Diseases 0.000 claims description 3
235000010290 biphenyl Nutrition 0.000 claims description 3
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
238000007796 conventional method Methods 0.000 claims description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
206010061289 metastatic neoplasm Diseases 0.000 claims description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
231100000397 ulcer Toxicity 0.000 claims description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
CZAUOFXREFVFBI-UHFFFAOYSA-N 5-bromo-2-[[3-(trifluoromethyl)phenyl]carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 CZAUOFXREFVFBI-UHFFFAOYSA-N 0.000 claims description 2
ZZSSXILLOUQSIX-UHFFFAOYSA-N 5-chloro-2-[[3-(trifluoromethyl)phenyl]carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 ZZSSXILLOUQSIX-UHFFFAOYSA-N 0.000 claims description 2
AUTSRTJPPGRBSE-UHFFFAOYSA-N 5-fluoro-2-[[3-(trifluoromethyl)phenyl]carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC(F)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 AUTSRTJPPGRBSE-UHFFFAOYSA-N 0.000 claims description 2
239000002727 chloride channel blocking agent Substances 0.000 claims description 2
230000035876 healing Effects 0.000 claims description 2
230000001394 metastastic effect Effects 0.000 claims description 2
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims 2
WUSZFHPXEBQXEL-UHFFFAOYSA-N 2-[methyl-[[3-(trifluoromethyl)phenyl]carbamoyl]amino]benzoic acid Chemical compound C=1C=CC=C(C(O)=O)C=1N(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 WUSZFHPXEBQXEL-UHFFFAOYSA-N 0.000 claims 1
240000000785 Tagetes erecta Species 0.000 claims 1
ZSRNFXQWCQXPSR-UHFFFAOYSA-N [4-(2-phenylphenyl)-2-(2h-tetrazol-5-yl)phenyl]urea Chemical compound NC(=O)NC1=CC=C(C=2C(=CC=CC=2)C=2C=CC=CC=2)C=C1C1=NN=NN1 ZSRNFXQWCQXPSR-UHFFFAOYSA-N 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
238000001727 in vivo Methods 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 28
239000000243 solution Substances 0.000 description 23
241000736851 Tagetes Species 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
239000004480 active ingredient Substances 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
230000000903 blocking effect Effects 0.000 description 13
239000002552 dosage form Substances 0.000 description 13
210000003743 erythrocyte Anatomy 0.000 description 13
238000009472 formulation Methods 0.000 description 13
239000012528 membrane Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000000843 powder Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000002775 capsule Substances 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 8
208000001132 Osteoporosis Diseases 0.000 description 7
239000002253 acid Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 6
108091006146 Channels Proteins 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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230000003389 potentiating effect Effects 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
108010083204 Proton Pumps Proteins 0.000 description 5
229940011871 estrogen Drugs 0.000 description 5
239000000262 estrogen Substances 0.000 description 5
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150000001450 anions Chemical class 0.000 description 4
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
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238000006243 chemical reaction Methods 0.000 description 4
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LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
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239000000375 suspending agent Substances 0.000 description 4
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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241000132025 Calendula Species 0.000 description 3
108010078791 Carrier Proteins Proteins 0.000 description 3
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108010010803 Gelatin Proteins 0.000 description 3
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
102100032709 Potassium-transporting ATPase alpha chain 2 Human genes 0.000 description 3
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108010016797 Sickle Hemoglobin Proteins 0.000 description 3
229930006000 Sucrose Natural products 0.000 description 3
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
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229910052794 bromium Inorganic materials 0.000 description 3
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125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
235000002020 sage Nutrition 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
239000002002 slurry Substances 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
150000001629 stilbenes Chemical class 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 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
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
230000008719 thickening Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
FCFNRCROJUBPLU-DNDCDFAISA-N valinomycin Chemical compound CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC1=O FCFNRCROJUBPLU-DNDCDFAISA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/30—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by halogen atoms, or by nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/42—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Orthopedic Medicine & Surgery (AREA)
Ophthalmology & Optometry (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Oncology (AREA)
Immunology (AREA)
Pulmonology (AREA)
Dermatology (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)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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SK522-2001A 1998-10-22 1999-10-19 Substituted phenyl derivatives, their preparation and use SK5222001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA199801362		1998-10-22
PCT/DK1999/000575 WO2000024707A1 (fr)	1998-10-22	1999-10-19	Derives de phenyle substitue, leur preparation et leur application

Publications (1)

Publication Number	Publication Date
SK5222001A3 true SK5222001A3 (en)	2002-05-09

Family

ID=8104026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK522-2001A SK5222001A3 (en)	1998-10-22	1999-10-19	Substituted phenyl derivatives, their preparation and use

Country Status (27)

Country	Link
US (1)	US6706749B2 (fr)
EP (2)	EP1514867A3 (fr)
JP (2)	JP3960754B2 (fr)
KR (1)	KR100799892B1 (fr)
CN (1)	CN1263733C (fr)
AP (1)	AP2001002103A0 (fr)
AT (1)	ATE286021T1 (fr)
AU (1)	AU759275B2 (fr)
BR (1)	BR9914638A (fr)
CA (1)	CA2342626A1 (fr)
DE (1)	DE69922986T2 (fr)
EE (1)	EE04849B1 (fr)
ES (1)	ES2235522T3 (fr)
HU (1)	HUP0103673A3 (fr)
IL (2)	IL141479A0 (fr)
IS (1)	IS2215B (fr)
NO (1)	NO20011956L (fr)
NZ (1)	NZ510098A (fr)
OA (1)	OA11665A (fr)
PL (1)	PL198852B1 (fr)
PT (1)	PT1123274E (fr)
RU (1)	RU2218328C2 (fr)
SK (1)	SK5222001A3 (fr)
TR (1)	TR200101126T2 (fr)
UA (1)	UA73284C2 (fr)
WO (1)	WO2000024707A1 (fr)
ZA (1)	ZA200101824B (fr)

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1999
- 1999-10-19 SK SK522-2001A patent/SK5222001A3/sk unknown
- 1999-10-19 HU HU0103673A patent/HUP0103673A3/hu unknown
- 1999-10-19 EP EP04105861A patent/EP1514867A3/fr not_active Withdrawn
- 1999-10-19 TR TR2001/01126T patent/TR200101126T2/xx unknown
- 1999-10-19 PL PL347371A patent/PL198852B1/pl unknown
- 1999-10-19 EE EEP200100185A patent/EE04849B1/xx not_active IP Right Cessation
- 1999-10-19 UA UA2001021084A patent/UA73284C2/uk unknown
- 1999-10-19 KR KR1020017004970A patent/KR100799892B1/ko not_active Expired - Fee Related
- 1999-10-19 ES ES99950505T patent/ES2235522T3/es not_active Expired - Lifetime
- 1999-10-19 DE DE69922986T patent/DE69922986T2/de not_active Expired - Lifetime
- 1999-10-19 ZA ZA200101824A patent/ZA200101824B/en unknown
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- 1999-10-19 BR BR9914638-0A patent/BR9914638A/pt not_active Application Discontinuation
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- 1999-10-19 AT AT99950505T patent/ATE286021T1/de not_active IP Right Cessation
- 1999-10-19 AU AU63259/99A patent/AU759275B2/en not_active Ceased
- 1999-10-19 JP JP2000578279A patent/JP3960754B2/ja not_active Expired - Fee Related
- 1999-10-19 CN CNB998117730A patent/CN1263733C/zh not_active Expired - Fee Related
- 1999-10-19 AP APAP/P/2001/002103A patent/AP2001002103A0/en unknown
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- 1999-10-19 EP EP99950505A patent/EP1123274B1/fr not_active Expired - Lifetime
- 1999-10-19 IL IL14147999A patent/IL141479A0/xx active IP Right Grant
- 1999-10-19 CA CA002342626A patent/CA2342626A1/fr not_active Abandoned
- 1999-10-19 WO PCT/DK1999/000575 patent/WO2000024707A1/fr not_active Ceased
- 1999-10-19 RU RU2001107853/04A patent/RU2218328C2/ru not_active IP Right Cessation
2001
- 2001-02-16 IL IL141479A patent/IL141479A/en not_active IP Right Cessation
- 2001-03-02 IS IS5875A patent/IS2215B/is unknown
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- 2001-04-20 NO NO20011956A patent/NO20011956L/no not_active Application Discontinuation
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Also Published As

Publication number	Publication date
EP1514867A3 (fr)	2005-03-23
JP2003246773A (ja)	2003-09-02
HK1040699A1 (en)	2002-06-21
NO20011956D0 (no)	2001-04-20
CN1263733C (zh)	2006-07-12
TR200101126T2 (tr)	2001-09-21
EE04849B1 (et)	2007-06-15
PL198852B1 (pl)	2008-07-31
US20020032210A1 (en)	2002-03-14
DE69922986D1 (de)	2005-02-03
BR9914638A (pt)	2001-07-03
HUP0103673A3 (en)	2003-03-28
PT1123274E (pt)	2005-04-29
IS2215B (is)	2007-03-15
IL141479A0 (en)	2002-03-10
JP2002528432A (ja)	2002-09-03
WO2000024707A1 (fr)	2000-05-04
KR100799892B1 (ko)	2008-01-31
AP2001002103A0 (en)	2001-03-31
ZA200101824B (en)	2002-03-05
DE69922986T2 (de)	2005-07-07
EP1123274A1 (fr)	2001-08-16
CA2342626A1 (fr)	2000-05-04
KR20010080270A (ko)	2001-08-22
EE200100185A (et)	2002-08-15
EP1514867A2 (fr)	2005-03-16
IS5875A (is)	2001-03-02
OA11665A (en)	2004-12-08
EP1123274B1 (fr)	2004-12-29
NO20011956L (no)	2001-04-20
US6706749B2 (en)	2004-03-16
ES2235522T3 (es)	2005-07-01
IL141479A (en)	2006-08-20
NZ510098A (en)	2003-09-26
UA73284C2 (en)	2005-07-15
ATE286021T1 (de)	2005-01-15
PL347371A1 (en)	2002-04-08
HUP0103673A2 (hu)	2002-02-28
CN1322194A (zh)	2001-11-14
AU6325999A (en)	2000-05-15
AU759275B2 (en)	2003-04-10
RU2218328C2 (ru)	2003-12-10
JP3960754B2 (ja)	2007-08-15

Publication	Publication Date	Title
US6706749B2 (en)	2004-03-16	Substituted phenyl derivatives, their preparation and use
US6696475B2 (en)	2004-02-24	Substituted phenyl derivatives, their preparation and use
US6297261B1 (en)	2001-10-02	Substituted phenyl derivatives, their preparation and use
EP0906273B1 (fr)	2002-10-16	Derives phenyle contenant un groupe acide, leur preparation et leur utilisation comme inhibiteurs des vannes a chlorure
WO1997045111A1 (fr)	1997-12-04	Derives phenyliques servant d'antagonistes des canaux chlorure
EP1117633B1 (fr)	2002-09-18	Derives de diaminocyclobutene-3,4-dione, leur preparation et utilisation
CZ20011020A3 (cs)	2001-07-11	Substituované fenylové deriváty, způsob jejich přípravy a jejich použití