HU183013B - Process for producing pharmaceutical compositions containing n-phenyl-n-comma above-bracket-2-imidazolidinilidene-bracket closed-urea derivatives as active agents for treating high blood-pressure and irregular intestinal activity - Google Patents
Process for producing pharmaceutical compositions containing n-phenyl-n-comma above-bracket-2-imidazolidinilidene-bracket closed-urea derivatives as active agents for treating high blood-pressure and irregular intestinal activity Download PDFInfo
- Publication number
- HU183013B HU183013B HU79MA3254A HUMA003254A HU183013B HU 183013 B HU183013 B HU 183013B HU 79MA3254 A HU79MA3254 A HU 79MA3254A HU MA003254 A HUMA003254 A HU MA003254A HU 183013 B HU183013 B HU 183013B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- phenyl
- urea
- imidazolidinylidene
- active ingredient
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 206010020772 Hypertension Diseases 0.000 title claims abstract description 17
- 239000013543 active substance Substances 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title description 10
- 230000000968 intestinal effect Effects 0.000 title description 5
- 230000001788 irregular Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 208000028774 intestinal disease Diseases 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- -1 2-imidazolidinylidene Chemical group 0.000 claims description 47
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000004202 carbamide Substances 0.000 claims description 14
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 14
- WTABVQIXVUVUPO-UHFFFAOYSA-N 1-(4,5-dihydro-1h-imidazol-2-yl)-3-phenylurea Chemical class N1CCNC1=NC(=O)NC1=CC=CC=C1 WTABVQIXVUVUPO-UHFFFAOYSA-N 0.000 claims description 10
- 239000002775 capsule Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 7
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- MOTOYHLEARSUHT-UHFFFAOYSA-N 1-(2-chloro-6-methylphenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical group CC1=CC=CC(Cl)=C1NC(=O)N=C1NCCN1 MOTOYHLEARSUHT-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- YPPHTRBBTRJOFR-UHFFFAOYSA-N 1-(4,5-dihydro-1h-imidazol-2-yl)-3-(2-methoxyphenyl)urea Chemical group COC1=CC=CC=C1NC(=O)N=C1NCCN1 YPPHTRBBTRJOFR-UHFFFAOYSA-N 0.000 claims description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 abstract description 14
- 150000003672 ureas Chemical class 0.000 abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 28
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- 230000037396 body weight Effects 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000012458 free base Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 229920002472 Starch Polymers 0.000 description 9
- 235000019698 starch Nutrition 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000004872 arterial blood pressure Effects 0.000 description 8
- 239000007903 gelatin capsule Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000008107 starch Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- 230000003276 anti-hypertensive effect Effects 0.000 description 7
- 239000011324 bead Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 5
- 239000008116 calcium stearate Substances 0.000 description 5
- 235000013539 calcium stearate Nutrition 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 5
- 229910000103 lithium hydride Inorganic materials 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 210000001715 carotid artery Anatomy 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000000004 hemodynamic effect Effects 0.000 description 4
- 230000001631 hypertensive effect Effects 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 210000000664 rectum Anatomy 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FWCAIBQYLXLUIH-UHFFFAOYSA-N 1-(4,5-dihydro-1h-imidazol-2-yl)-3-(2,6-dimethylphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)N=C1NCCN1 FWCAIBQYLXLUIH-UHFFFAOYSA-N 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- 206010000060 Abdominal distension Diseases 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 206010012735 Diarrhoea Diseases 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 208000024330 bloating Diseases 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012022 methylating agents Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- PERQBEGUHWUECA-UHFFFAOYSA-N 1-(2,6-dibromophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical compound BrC1=CC=CC(Br)=C1NC(=O)N=C1NCCN1 PERQBEGUHWUECA-UHFFFAOYSA-N 0.000 description 2
- XARVUBHGHXFYRY-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical compound ClC1=CC=CC(Cl)=C1NC(=O)N=C1NCCN1 XARVUBHGHXFYRY-UHFFFAOYSA-N 0.000 description 2
- DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical class NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 description 2
- 208000004998 Abdominal Pain Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 206010010774 Constipation Diseases 0.000 description 2
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical class NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- UFBUJVYYRKZXDL-UHFFFAOYSA-N NC(=O)N.N1CNCCC1 Chemical class NC(=O)N.N1CNCCC1 UFBUJVYYRKZXDL-UHFFFAOYSA-N 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000002051 biphasic effect Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
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- 238000007796 conventional method Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
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- 239000004615 ingredient Substances 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
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- 238000007911 parenteral administration Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
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- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- DTAGLQWFBAMCEW-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(4,5-dihydro-1h-imidazol-2-yl)-3-(2-ethyl-6-methylphenyl)urea Chemical compound OC(=O)\C=C\C(O)=O.CCC1=CC=CC(C)=C1NC(=O)NC1=NCCN1 DTAGLQWFBAMCEW-WLHGVMLRSA-N 0.000 description 1
- KKUGLUXXIGKECX-TYYBGVCCSA-N (e)-but-2-enedioic acid;urea Chemical compound NC(N)=O.OC(=O)\C=C\C(O)=O KKUGLUXXIGKECX-TYYBGVCCSA-N 0.000 description 1
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- CIYFOGQTBIVHFW-UHFFFAOYSA-N 1,3-dibromo-2-isocyanatobenzene Chemical compound BrC1=CC=CC(Br)=C1N=C=O CIYFOGQTBIVHFW-UHFFFAOYSA-N 0.000 description 1
- HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 description 1
- WSUKOYBCSJXQMO-UHFFFAOYSA-N 1-(2,3-dichlorophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical compound ClC1=CC=CC(NC(=O)N=C2NCCN2)=C1Cl WSUKOYBCSJXQMO-UHFFFAOYSA-N 0.000 description 1
- DZDIAZOSDMOERM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical compound ClC1=CC(Cl)=CC=C1NC(=O)N=C1NCCN1 DZDIAZOSDMOERM-UHFFFAOYSA-N 0.000 description 1
- GIGMUWXRCATXJV-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea;hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1NC(=O)N=C1NCCN1 GIGMUWXRCATXJV-UHFFFAOYSA-N 0.000 description 1
- DPGJJZUGMYASLA-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-3-(1-methyl-4,5-dihydroimidazol-2-yl)urea Chemical compound CN1CCN=C1NC(=O)NC1=C(C)C=CC=C1C DPGJJZUGMYASLA-UHFFFAOYSA-N 0.000 description 1
- UEESJFNJVGYTDD-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical compound ClC1=CC=CC=C1NC(=O)N=C1NCCN1 UEESJFNJVGYTDD-UHFFFAOYSA-N 0.000 description 1
- WFBWWQZDEPAKBX-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical compound ClC1=CC(Cl)=CC(NC(=O)N=C2NCCN2)=C1 WFBWWQZDEPAKBX-UHFFFAOYSA-N 0.000 description 1
- VKRRAGLNUVUCEY-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(4,5-dihydro-1h-imidazol-2-yl)urea Chemical compound ClC1=CC=CC(NC(=O)N=C2NCCN2)=C1 VKRRAGLNUVUCEY-UHFFFAOYSA-N 0.000 description 1
- DVGGCYULVJSHAT-UHFFFAOYSA-N 1-(4,5-dihydro-1h-imidazol-2-yl)-3-(2,4,6-trichlorophenyl)urea Chemical compound ClC1=CC(Cl)=CC(Cl)=C1NC(=O)N=C1NCCN1 DVGGCYULVJSHAT-UHFFFAOYSA-N 0.000 description 1
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical class NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 1
- MJJSNLJGOXWVEU-UHFFFAOYSA-N 1-carbamoyl-3-phenylurea Chemical compound NC(=O)NC(=O)NC1=CC=CC=C1 MJJSNLJGOXWVEU-UHFFFAOYSA-N 0.000 description 1
- NOHQUGRVHSJYMR-UHFFFAOYSA-N 1-chloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC=C1N=C=O NOHQUGRVHSJYMR-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- YMAVXDRFOILNKI-UHFFFAOYSA-N 1-ethyl-2-isocyanato-3-methylbenzene Chemical compound CCC1=CC=CC(C)=C1N=C=O YMAVXDRFOILNKI-UHFFFAOYSA-N 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
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- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 1
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 206010000059 abdominal discomfort Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 210000003403 autonomic nervous system Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- JNWJBIAPDBZUQL-UHFFFAOYSA-N carbamodithioic acid;hydroiodide Chemical compound I.NC(S)=S JNWJBIAPDBZUQL-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 229960004486 desoxycorticosterone acetate Drugs 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- KCJVRKYRNMIUGL-UHFFFAOYSA-J dicalcium octadecanoate Chemical compound [Ca++].[Ca++].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O KCJVRKYRNMIUGL-UHFFFAOYSA-J 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 210000004247 hand Anatomy 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- PFRDRCIPKPEULG-UHFFFAOYSA-N imidazol-2-imine Chemical compound N=C1N=CC=N1 PFRDRCIPKPEULG-UHFFFAOYSA-N 0.000 description 1
- NTFOMPCTOJCWEK-UHFFFAOYSA-N imidazolidine-1-carboxamide Chemical compound NC(=O)N1CCNC1 NTFOMPCTOJCWEK-UHFFFAOYSA-N 0.000 description 1
- ATYGMDZIBQHJFX-UHFFFAOYSA-N imidazolidine;urea Chemical class NC(N)=O.C1CNCN1 ATYGMDZIBQHJFX-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical compound COF XMSZANIMCDLNKA-UHFFFAOYSA-N 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000007383 nerve stimulation Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 208000006379 syphilis Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000003813 thumb Anatomy 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
- 230000001960 triggered effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- 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
- C07D233/42—Sulfur atoms
-
- 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
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/972,579 US4229462A (en) | 1978-12-22 | 1978-12-22 | Method for controlling hypertension and compositions |
| US05/972,580 US4239768A (en) | 1978-12-22 | 1978-12-22 | Method for relieving irritable bowel syndrome symptoms |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU183013B true HU183013B (en) | 1984-04-28 |
Family
ID=27130555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79MA3254A HU183013B (en) | 1978-12-22 | 1979-12-21 | Process for producing pharmaceutical compositions containing n-phenyl-n-comma above-bracket-2-imidazolidinilidene-bracket closed-urea derivatives as active agents for treating high blood-pressure and irregular intestinal activity |
Country Status (23)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4673680A (en) * | 1985-09-18 | 1987-06-16 | Pendleton Robert G | α2 -adrenergic receptor antagonists as modifiers of gastrointestinal motility |
| US11516649B2 (en) | 2018-10-29 | 2022-11-29 | Apple Inc. | Mechanism to activate and manage a standalone device for cellular service |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1296962A (fr) * | 1960-08-05 | 1962-06-22 | Geigy Ag J R | Nouveaux composés 2-imino-1.3-di-aza et leur préparation |
| NL288408A (enrdf_load_stackoverflow) * | 1960-08-05 |
-
1979
- 1979-12-06 GR GR60697A patent/GR68018B/el unknown
- 1979-12-06 CA CA341,351A patent/CA1127651A/en not_active Expired
- 1979-12-13 PH PH23413A patent/PH16571A/en unknown
- 1979-12-13 AU AU53780/79A patent/AU532332B2/en not_active Ceased
- 1979-12-18 NZ NZ192453A patent/NZ192453A/xx unknown
- 1979-12-19 DE DE19792951213 patent/DE2951213A1/de not_active Ceased
- 1979-12-20 DK DK548179A patent/DK548179A/da not_active Application Discontinuation
- 1979-12-20 ES ES487159A patent/ES8101558A1/es not_active Expired
- 1979-12-21 IL IL59019A patent/IL59019A/xx unknown
- 1979-12-21 CH CH11419/79A patent/CH647236A5/de not_active IP Right Cessation
- 1979-12-21 PT PT70624A patent/PT70624A/pt unknown
- 1979-12-21 NO NO794249A patent/NO794249L/no unknown
- 1979-12-21 SE SE7910612A patent/SE7910612L/xx not_active Application Discontinuation
- 1979-12-21 SU SU792860905A patent/SU971098A3/ru active
- 1979-12-21 YU YU03149/79A patent/YU314979A/xx unknown
- 1979-12-21 NL NL7909265A patent/NL7909265A/nl not_active Application Discontinuation
- 1979-12-21 ZW ZW253/79A patent/ZW25379A1/xx unknown
- 1979-12-21 GB GB7944114A patent/GB2040681B/en not_active Expired
- 1979-12-21 IT IT51164/79A patent/IT1126839B/it active
- 1979-12-21 AT AT0808979A patent/AT373878B/de active
- 1979-12-21 HU HU79MA3254A patent/HU183013B/hu unknown
- 1979-12-21 FI FI794036A patent/FI66354C/fi not_active IP Right Cessation
- 1979-12-21 FR FR7931473A patent/FR2444462B1/fr not_active Expired
-
1980
- 1980-04-04 FR FR8007757A patent/FR2445321B1/fr not_active Expired
-
1982
- 1982-07-26 GB GB08221517A patent/GB2113204B/en not_active Expired
-
1983
- 1983-06-29 AU AU16400/83A patent/AU566013B2/en not_active Expired - Fee Related
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