IL43280A - Preparation of(substituted phenylamidino)urea derivatives pharmaceutical compositions containing them and some new such derivatives - Google Patents
Preparation of(substituted phenylamidino)urea derivatives pharmaceutical compositions containing them and some new such derivativesInfo
- Publication number
- IL43280A IL43280A IL43280A IL4328073A IL43280A IL 43280 A IL43280 A IL 43280A IL 43280 A IL43280 A IL 43280A IL 4328073 A IL4328073 A IL 4328073A IL 43280 A IL43280 A IL 43280A
- Authority
- IL
- Israel
- Prior art keywords
- urea
- hydrogen
- compound
- ami
- chloro
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- -1 phenylamidino Chemical group 0.000 title description 76
- 150000003672 ureas Chemical class 0.000 title description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 29
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims 1
- 241000161214 Pelates Species 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 6
- QRJZGVVKGFIGLI-UHFFFAOYSA-N 2-phenylguanidine Chemical class NC(=N)NC1=CC=CC=C1 QRJZGVVKGFIGLI-UHFFFAOYSA-N 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract description 3
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 239000008280 blood Substances 0.000 abstract 1
- 210000004369 blood Anatomy 0.000 abstract 1
- 229940125692 cardiovascular agent Drugs 0.000 abstract 1
- 239000002327 cardiovascular agent Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 description 225
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 203
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 110
- 229960004198 guanidine Drugs 0.000 description 68
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 67
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 67
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 18
- QHDUJTCUPWHNPK-UHFFFAOYSA-N methyl 7-methoxy-2h-indazole-3-carboxylate Chemical compound COC1=CC=CC2=C(C(=O)OC)NN=C21 QHDUJTCUPWHNPK-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical group 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940030600 antihypertensive agent Drugs 0.000 description 6
- 239000002220 antihypertensive agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 5
- XIWRCSVXKPGGAJ-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylpyrazol-3-yl)-3-(4-chlorophenyl)urea Chemical compound C=1C=CC=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC1=CC=C(Cl)C=C1 XIWRCSVXKPGGAJ-UHFFFAOYSA-N 0.000 description 4
- 101100162703 Caenorhabditis elegans ani-1 gene Proteins 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 229940039407 aniline Drugs 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 230000000875 corresponding effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZQIZQFXYBZUGIV-UHFFFAOYSA-N (z)-[amino-(2-chloro-6-iodoanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=C(Cl)C=CC=C1I ZQIZQFXYBZUGIV-UHFFFAOYSA-N 0.000 description 2
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 2
- FBVLZVUGJGEIEC-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)guanidine Chemical compound NC(=N)NC1=C(Cl)C=CC=C1Cl FBVLZVUGJGEIEC-UHFFFAOYSA-N 0.000 description 2
- IUNFWMWQNWQIFS-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]guanidine Chemical compound NC(=N)NC1=CC=C(C(F)(F)F)C=C1 IUNFWMWQNWQIFS-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- QLYHPNUFNZJXOQ-UHFFFAOYSA-N 4-bromo-3-chloroaniline Chemical compound NC1=CC=C(Br)C(Cl)=C1 QLYHPNUFNZJXOQ-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 101150052863 THY1 gene Proteins 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002357 guanidines Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OLZQRUORFWJUOS-UHFFFAOYSA-N (1z)-1-[amino-(4-nitroanilino)methylidene]-3-tert-butylurea Chemical compound CC(C)(C)NC(=O)NC(=N)NC1=CC=C([N+]([O-])=O)C=C1 OLZQRUORFWJUOS-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- GLCMEYWDADEDJM-UHFFFAOYSA-N (e)-[amino-(2,3-dichloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=CC(Cl)=C1Cl GLCMEYWDADEDJM-UHFFFAOYSA-N 0.000 description 1
- TVTVLCUJVONXCZ-UHFFFAOYSA-N (e)-[amino-(2,4-dichloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=C(Cl)C=C1Cl TVTVLCUJVONXCZ-UHFFFAOYSA-N 0.000 description 1
- NNGPPQLHGNKUJK-UHFFFAOYSA-N (e)-[amino-(2-chloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=CC=C1Cl NNGPPQLHGNKUJK-UHFFFAOYSA-N 0.000 description 1
- JHXYHSCRDRQCBJ-UHFFFAOYSA-N (e)-[amino-(3,5-dichloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC(Cl)=CC(Cl)=C1 JHXYHSCRDRQCBJ-UHFFFAOYSA-N 0.000 description 1
- BOOQMJSRKPNNHU-UHFFFAOYSA-N (e)-[amino-(3-chloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=CC(Cl)=C1 BOOQMJSRKPNNHU-UHFFFAOYSA-N 0.000 description 1
- HOYFAIPGAJZCCC-UHFFFAOYSA-N (e)-[amino-(4-bromoanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=C(Br)C=C1 HOYFAIPGAJZCCC-UHFFFAOYSA-N 0.000 description 1
- SENRXQNLMOCTKF-UHFFFAOYSA-N (e)-[amino-(4-chloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=C(Cl)C=C1 SENRXQNLMOCTKF-UHFFFAOYSA-N 0.000 description 1
- IFOISTDABAJECI-UHFFFAOYSA-N (e)-[amino-(4-fluoroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=C(F)C=C1 IFOISTDABAJECI-UHFFFAOYSA-N 0.000 description 1
- BRUQZGSQYQXLME-UHFFFAOYSA-N (e)-[amino-[2-(trifluoromethyl)anilino]methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=CC=C1C(F)(F)F BRUQZGSQYQXLME-UHFFFAOYSA-N 0.000 description 1
- UIPWSEXDPGFJTR-UHFFFAOYSA-N (z)-[amino-(2,3,6-trichloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=C(Cl)C=CC(Cl)=C1Cl UIPWSEXDPGFJTR-UHFFFAOYSA-N 0.000 description 1
- HAZNAUBETKCFPK-UHFFFAOYSA-N (z)-[amino-(2,4,5-trichloroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC(Cl)=C(Cl)C=C1Cl HAZNAUBETKCFPK-UHFFFAOYSA-N 0.000 description 1
- XHXOHDYLVFHMST-UHFFFAOYSA-N (z)-[amino-(2,4,6-tribromoanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=C(Br)C=C(Br)C=C1Br XHXOHDYLVFHMST-UHFFFAOYSA-N 0.000 description 1
- PFOJDGCGDFTOCP-UHFFFAOYSA-N (z)-[amino-(2,4-dibromoanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=C(Br)C=C1Br PFOJDGCGDFTOCP-UHFFFAOYSA-N 0.000 description 1
- MGVPFJMTCPZQKG-UHFFFAOYSA-N (z)-[amino-(2,4-diiodoanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=C(I)C=C1I MGVPFJMTCPZQKG-UHFFFAOYSA-N 0.000 description 1
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- GKKUSWKEFJJEMH-UHFFFAOYSA-N (z)-[amino-(4-chloro-2-ethylanilino)methylidene]urea Chemical compound CCC1=CC(Cl)=CC=C1NC(=N)NC(N)=O GKKUSWKEFJJEMH-UHFFFAOYSA-N 0.000 description 1
- RZWAWJYAEXHEHF-UHFFFAOYSA-N (z)-[amino-(4-chloro-2-fluoroanilino)methylidene]urea Chemical compound NC(=O)NC(=N)NC1=CC=C(Cl)C=C1F RZWAWJYAEXHEHF-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 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 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/275—Nitriles; Isonitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29147472A | 1972-09-22 | 1972-09-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL43280A0 IL43280A0 (en) | 1973-11-28 |
| IL43280A true IL43280A (en) | 1977-06-30 |
Family
ID=23120445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL43280A IL43280A (en) | 1972-09-22 | 1973-09-21 | Preparation of(substituted phenylamidino)urea derivatives pharmaceutical compositions containing them and some new such derivatives |
Country Status (14)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220658A (en) * | 1972-09-22 | 1980-09-02 | William H. Rorer, Inc. | Treatment of hypertension with amidinoureas |
| US4488993A (en) * | 1972-09-22 | 1984-12-18 | William H. Rorer, Inc. | Amidinoureas |
| US4025652A (en) * | 1975-03-31 | 1977-05-24 | William H. Rorer, Inc. | Amidinoureas |
| US4326074A (en) | 1972-09-22 | 1982-04-20 | William H. Rorer, Inc. | Amidinoureas |
| US4713382A (en) * | 1985-05-30 | 1987-12-15 | Syntex (U.S.A.) Inc. | N-phenyl-4-phenyl-1-piperazinecarboxamidines and related compounds as antiarrhythmic agents |
| EP0612723B1 (de) * | 1993-02-20 | 1997-08-27 | Hoechst Aktiengesellschaft | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, als Inhibitoren des zellulären Na+/H+-Austauschs oder als Diagnostikum sowie sie enthaltendes Medikament |
| RU2156759C1 (ru) * | 2000-01-24 | 2000-09-27 | Совместное предприятие Закрытое акционерное общество "Пронова" | Способ получения n, n'-дифенилгуанидина |
-
1973
- 1973-09-10 PH PH15001A patent/PH12016A/en unknown
- 1973-09-12 DE DE2345951A patent/DE2345951C2/de not_active Expired
- 1973-09-13 CA CA181,015A patent/CA1041908A/en not_active Expired
- 1973-09-17 CH CH1330773A patent/CH605703A5/xx not_active IP Right Cessation
- 1973-09-17 CH CH1605977A patent/CH614430A5/xx not_active IP Right Cessation
- 1973-09-20 AR AR250179A patent/AR200024A1/es active
- 1973-09-21 BE BE135886A patent/BE805138A/xx not_active IP Right Cessation
- 1973-09-21 ES ES418987A patent/ES418987A1/es not_active Expired
- 1973-09-21 JP JP48107418A patent/JPS593471B2/ja not_active Expired
- 1973-09-21 NL NL7313040A patent/NL7313040A/xx not_active Application Discontinuation
- 1973-09-21 ZA ZA737475A patent/ZA737475B/xx unknown
- 1973-09-21 SE SE7312880A patent/SE416952B/xx unknown
- 1973-09-21 FR FR7333963A patent/FR2200002B1/fr not_active Expired
- 1973-09-21 IL IL43280A patent/IL43280A/en unknown
- 1973-09-24 GB GB4465473A patent/GB1451477A/en not_active Expired
- 1973-09-24 GB GB2491476A patent/GB1451479A/en not_active Expired
- 1973-09-24 GB GB2499276A patent/GB1451480A/en not_active Expired
- 1973-09-24 GB GB3221175A patent/GB1451478A/en not_active Expired
-
1975
- 1975-05-30 GB GB23574/75A patent/GB1514198A/en not_active Expired
-
1976
- 1976-11-02 SE SE7612176A patent/SE416953B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1451477A (en) | 1976-10-06 |
| DE2345951C2 (de) | 1986-10-23 |
| IL43280A0 (en) | 1973-11-28 |
| FR2200002A1 (enrdf_load_stackoverflow) | 1974-04-19 |
| BE805138A (fr) | 1974-01-16 |
| ES418987A1 (es) | 1976-07-01 |
| NL7313040A (enrdf_load_stackoverflow) | 1974-03-26 |
| GB1514198A (en) | 1978-06-14 |
| CH605703A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| GB1451479A (en) | 1976-10-06 |
| SE7612176L (sv) | 1976-11-02 |
| AU6047973A (en) | 1975-03-20 |
| CH614430A5 (en) | 1979-11-30 |
| ZA737475B (en) | 1974-10-30 |
| SE416952B (sv) | 1981-02-16 |
| FR2200002B1 (enrdf_load_stackoverflow) | 1977-07-15 |
| JPS593471B2 (ja) | 1984-01-24 |
| DE2345951A1 (de) | 1974-04-04 |
| GB1451478A (en) | 1976-10-06 |
| AR200024A1 (es) | 1974-10-15 |
| CA1041908A (en) | 1978-11-07 |
| PH12016A (en) | 1978-10-06 |
| SE416953B (sv) | 1981-02-16 |
| GB1451480A (en) | 1976-10-06 |
| JPS4985046A (enrdf_load_stackoverflow) | 1974-08-15 |
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