IE41459B1 - Benzothiazolyl ureas and pharmaceutical compositions containing them - Google Patents
Benzothiazolyl ureas and pharmaceutical compositions containing themInfo
- Publication number
- IE41459B1 IE41459B1 IE1858/75A IE185875A IE41459B1 IE 41459 B1 IE41459 B1 IE 41459B1 IE 1858/75 A IE1858/75 A IE 1858/75A IE 185875 A IE185875 A IE 185875A IE 41459 B1 IE41459 B1 IE 41459B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compound
- urea
- phenyl
- alkyl
- Prior art date
Links
- -1 Benzothiazolyl ureas Chemical class 0.000 title claims abstract description 31
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
- 235000013877 carbamide Nutrition 0.000 title abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 230000008569 process Effects 0.000 claims abstract description 9
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000003937 drug carrier Substances 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 28
- 239000004202 carbamide Substances 0.000 claims description 14
- 239000012948 isocyanate Substances 0.000 claims description 12
- 150000002513 isocyanates Chemical class 0.000 claims description 11
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 10
- VLNVTNUTGNBNBY-UHFFFAOYSA-N 2-amino-1,3-benzothiazol-6-ol Chemical compound C1=C(O)C=C2SC(N)=NC2=C1 VLNVTNUTGNBNBY-UHFFFAOYSA-N 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 4
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 abstract description 15
- 238000002360 preparation method Methods 0.000 abstract description 8
- 150000003672 ureas Chemical class 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 12
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 239000000427 antigen Substances 0.000 description 9
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 8
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 8
- 241001494479 Pecora Species 0.000 description 8
- 102000036639 antigens Human genes 0.000 description 8
- 108091007433 antigens Proteins 0.000 description 8
- 239000003018 immunosuppressive agent Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 210000000056 organ Anatomy 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 210000003743 erythrocyte Anatomy 0.000 description 6
- 230000028993 immune response Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 5
- 210000004698 lymphocyte Anatomy 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 101710154606 Hemagglutinin Proteins 0.000 description 4
- 101710093908 Outer capsid protein VP4 Proteins 0.000 description 4
- 101710135467 Outer capsid protein sigma-1 Proteins 0.000 description 4
- 101710176177 Protein A56 Proteins 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 239000000185 hemagglutinin Substances 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000003595 spectral effect Effects 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000890 antigenic effect Effects 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000001185 bone marrow Anatomy 0.000 description 3
- 230000035931 haemagglutination Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 210000003563 lymphoid tissue Anatomy 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- PGUKYDVWVXRPKK-UHFFFAOYSA-N (4-methoxyphenyl)urea Chemical compound COC1=CC=C(NC(N)=O)C=C1 PGUKYDVWVXRPKK-UHFFFAOYSA-N 0.000 description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 230000001363 autoimmune Effects 0.000 description 2
- 229960002170 azathioprine Drugs 0.000 description 2
- 210000000601 blood cell Anatomy 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003224 coccidiostatic agent Substances 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
- 235000005687 corn oil Nutrition 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000008260 defense mechanism Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 230000008076 immune mechanism Effects 0.000 description 2
- 230000008105 immune reaction Effects 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- CYMHGQMMXLASJI-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl) carbamate Chemical compound NC(=O)OC1=CC=C2N=C(N)SC2=C1 CYMHGQMMXLASJI-UHFFFAOYSA-N 0.000 description 1
- BLSVCHHBHKGCSQ-UHFFFAOYSA-N (2-methylphenyl)urea Chemical compound CC1=CC=CC=C1NC(N)=O BLSVCHHBHKGCSQ-UHFFFAOYSA-N 0.000 description 1
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- AYQVYEBEWIDXRO-UHFFFAOYSA-N 1,3-benzothiazol-2-ylurea Chemical compound C1=CC=C2SC(NC(=O)N)=NC2=C1 AYQVYEBEWIDXRO-UHFFFAOYSA-N 0.000 description 1
- LDFWEBWORFXBQN-UHFFFAOYSA-N 1-(1,3-benzothiazol-2-yl)-3-phenylurea Chemical compound N=1C2=CC=CC=C2SC=1NC(=O)NC1=CC=CC=C1 LDFWEBWORFXBQN-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- OLNLWAVOTVONIX-UHFFFAOYSA-N 2-(1h-benzimidazol-2-ylmethyl)phenol Chemical class OC1=CC=CC=C1CC1=NC2=CC=CC=C2N1 OLNLWAVOTVONIX-UHFFFAOYSA-N 0.000 description 1
- MXFMPTXDHSDMTI-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-benzimidazole Chemical class C1=CC=C2NC(C(F)(F)F)=NC2=C1 MXFMPTXDHSDMTI-UHFFFAOYSA-N 0.000 description 1
- VLQGGLVKPGDBAH-UHFFFAOYSA-N 2-amino-1,3-benzothiazol-6-ol;hydrochloride Chemical compound Cl.C1=C(O)C=C2SC(N)=NC2=C1 VLQGGLVKPGDBAH-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- MXJQJCACXRHPOV-UHFFFAOYSA-N 2-isocyanato-1,3-thiazole Chemical compound O=C=NC1=NC=CS1 MXJQJCACXRHPOV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- JGCYTKDCEQJSRX-UHFFFAOYSA-N 4-amino-3h-1,3-benzothiazol-2-one Chemical compound NC1=CC=CC2=C1N=C(O)S2 JGCYTKDCEQJSRX-UHFFFAOYSA-N 0.000 description 1
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 208000024869 Goodpasture syndrome Diseases 0.000 description 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- 208000005777 Lupus Nephritis Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010031068 Orchitis mumps Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000009359 Sezary Syndrome Diseases 0.000 description 1
- 208000021388 Sezary disease Diseases 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 210000000628 antibody-producing cell Anatomy 0.000 description 1
- 229940124623 antihistamine drug Drugs 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 description 1
- 210000003912 basophilic leucocyte Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 230000006409 bimodal response Effects 0.000 description 1
- SIOVKLKJSOKLIF-UHFFFAOYSA-N bis(trimethylsilyl)acetamide Chemical compound C[Si](C)(C)OC(C)=N[Si](C)(C)C SIOVKLKJSOKLIF-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000007969 cellular immunity Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- YGZSVWMBUCGDCV-UHFFFAOYSA-N chloro(methyl)silane Chemical compound C[SiH2]Cl YGZSVWMBUCGDCV-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000001335 demethylating effect Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002949 hemolytic effect Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000004727 humoral immunity Effects 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229960001330 hydroxycarbamide Drugs 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 229940124589 immunosuppressive drug Drugs 0.000 description 1
- 229940073062 imuran Drugs 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000005210 lymphoid organ Anatomy 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000005962 mycosis fungoides Diseases 0.000 description 1
- JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 210000004180 plasmocyte Anatomy 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/502,129 US3932434A (en) | 1974-08-30 | 1974-08-30 | N-2-(6-hydroxybenzothiazolyl)-N'-phenyl (or substituted phenyl) ureas |
| US05/502,130 US3932435A (en) | 1974-08-30 | 1974-08-30 | Preparation of N-2-(6-hydroxybenzothiazolyl)-N'-phenyl (or substituted-phenyl) ureas |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE41459L IE41459L (en) | 1976-02-29 |
| IE41459B1 true IE41459B1 (en) | 1980-01-02 |
Family
ID=27054031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1858/75A IE41459B1 (en) | 1974-08-30 | 1975-08-25 | Benzothiazolyl ureas and pharmaceutical compositions containing them |
Country Status (17)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2744893A1 (en) | 2002-06-27 | 2004-01-08 | Novo Nordisk A/S | Aryl carbonyl derivatives as glucokinase activators |
| RU2340605C2 (ru) * | 2002-06-27 | 2008-12-10 | Ново Нордиск А/С | Арилкарбонильные производные в качестве терапевтических средств |
-
1975
- 1975-01-01 AR AR260142A patent/AR206720A1/es active
- 1975-08-20 IL IL47963A patent/IL47963A/xx unknown
- 1975-08-21 RO RO7583221A patent/RO65771A/ro unknown
- 1975-08-25 IE IE1858/75A patent/IE41459B1/en unknown
- 1975-08-25 DE DE19752537777 patent/DE2537777A1/de not_active Withdrawn
- 1975-08-25 SE SE7509436A patent/SE415099B/xx unknown
- 1975-08-26 GB GB35151/75A patent/GB1516857A/en not_active Expired
- 1975-08-27 HU HU75EI641A patent/HU174132B/hu unknown
- 1975-08-27 FR FR7526386A patent/FR2282883A1/fr active Granted
- 1975-08-28 NL NL7510203A patent/NL7510203A/xx not_active Application Discontinuation
- 1975-08-28 PL PL1975182993A patent/PL108429B1/pl unknown
- 1975-08-28 DD DD188072A patent/DD122250A5/xx unknown
- 1975-08-29 ES ES440584A patent/ES440584A1/es not_active Expired
- 1975-08-29 DK DK389875A patent/DK389875A/da unknown
- 1975-08-29 AT AT669175A patent/AT344189B/de not_active IP Right Cessation
- 1975-08-30 BG BG030886A patent/BG23003A3/xx unknown
-
1976
- 1976-07-16 AR AR263977A patent/AR209974A1/es active
- 1976-07-26 SU SU762386210A patent/SU617013A3/ru active
-
1980
- 1980-01-04 SU SU802864197A patent/SU895290A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AR209974A1 (es) | 1977-06-15 |
| PL108429B1 (en) | 1980-04-30 |
| ES440584A1 (es) | 1977-05-16 |
| SE415099B (sv) | 1980-09-08 |
| BG23003A3 (bg) | 1977-05-20 |
| GB1516857A (en) | 1978-07-05 |
| NL7510203A (nl) | 1976-03-02 |
| ATA669175A (de) | 1977-11-15 |
| AT344189B (de) | 1978-07-10 |
| DD122250A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-20 |
| RO65771A (fr) | 1979-08-15 |
| SE7509436L (sv) | 1976-03-01 |
| AU8418575A (en) | 1977-02-24 |
| IL47963A0 (en) | 1975-11-25 |
| SU617013A3 (ru) | 1978-07-25 |
| FR2282883B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-09-14 |
| DK389875A (da) | 1976-03-01 |
| AR206720A1 (es) | 1976-08-13 |
| IL47963A (en) | 1978-07-31 |
| DE2537777A1 (de) | 1976-03-11 |
| SU895290A3 (ru) | 1981-12-30 |
| FR2282883A1 (fr) | 1976-03-26 |
| IE41459L (en) | 1976-02-29 |
| HU174132B (hu) | 1979-11-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4058614A (en) | Substituted imidazole compounds and therapeutic compositions therewith | |
| CZ178993A3 (en) | Hydrochloride of 5-(2-(4-(1,2-benzothiazol-3-yl)-1-piperazinyl) ethyl)-6-chloro-1,3-dihydro-2h-indol-2-one monohydrate, process of its preparation and pharmaceutical preparations in which such monohydrate is comprised | |
| CH644105A5 (fr) | Acides et esters 4-amino-3-quinoleinecarboxyliques, utiles notamment comme agent antisecretoires et anti-ulcere. | |
| US4512998A (en) | Anthelmintic benzimidazole carbamates | |
| US3759921A (en) | Method of suppressing immuneresponse with 1 substituted-3-(2 pyrimidyl)ureas | |
| US12202850B2 (en) | Cyclobutyl purine derivative or salt thereof | |
| US3932434A (en) | N-2-(6-hydroxybenzothiazolyl)-N'-phenyl (or substituted phenyl) ureas | |
| US3530142A (en) | N - (2 - benzoxazolyl or -benzothiazolyl)-aminomethylene-carboxylic acid esters | |
| KR880001677A (ko) | β-락탐 화합물, 그의 제조 방법, 이를 함유하는 세균 감염성 질병 치료용 약제 및 그의 합성을 위한 중간체 | |
| KR940003071B1 (ko) | 벤즈옥사진 유도체 및 이의 제조방법 | |
| IE41459B1 (en) | Benzothiazolyl ureas and pharmaceutical compositions containing them | |
| ATE64378T1 (de) | Spergualinaehnliche verbindungen und ihr herstellungsverfahren. | |
| KR0178956B1 (ko) | 항균성 페넴 에스테르 유도체 | |
| US4046770A (en) | N-(6-acyloxybenzothiazol-2-yl)-N'-phenyl (or substituted phenyl)ureas | |
| IE46605B1 (en) | Benzimidazole-2-thiones useful as anthelmintics | |
| CA1067499A (en) | N-(6-acyloxybenzothiazol-2-yl)-n'-phenyl (or substituted phenyl) ureas | |
| KR820002280B1 (ko) | 벤즈 이미다졸의 제조방법 | |
| KR790000979B1 (ko) | N-2-(6-하이드록시벤조치아조릴)-n'-페닐(혹은 치환된 페닐) 우레아류의 제조방법 | |
| EP0718290B1 (en) | Carboxyalkyl heterocyclic derivatives | |
| Bosin et al. | Routes of functionalized guanidines. Synthesis of guanidino diesters | |
| JP2991806B2 (ja) | ３‐（メルカプトアルキル）‐キナゾリン‐２，４（１ｈ，３ｈ）‐ジオン、その製造方法および製薬調合物 | |
| US4089965A (en) | Thiazolylphenylguanidines as antirhinovirus agents | |
| HU188805B (en) | Process for producing sulfonylurea derivatives and pharmaceutical compositions containing them as active agents | |
| US4451475A (en) | Cyclic sulphenamide compounds, their production and their medicinal use | |
| EP0224121A2 (en) | 7-[4-amino-piperazinyl]- or 7-[4-chloro-piperazinyl]quinolinone derivatives, a process for the preparation thereof and pharmaceutical compositions containing them |