NL7909265A - N-aryl-n'-(2-imidazolidinylideen)-ureumderivaten, alsmede farmaceutische preparaten, die deze derivaten bevatten. - Google Patents

N-aryl-n'-(2-imidazolidinylideen)-ureumderivaten, alsmede farmaceutische preparaten, die deze derivaten bevatten. Download PDF

Info

Publication number: NL7909265A
Authority: NL; Netherlands
Prior art keywords: urea; compound; imidazolidinylidene; formula; aryl
Prior art date: 1978-12-22

Application number

NL7909265A

Other languages

English (en)

Dutch (nl)

Original Assignee

Mcneilab Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-12-22

Filing date

1979-12-21

Publication date

1980-06-24

1978-12-22 Priority claimed from US05/972,580 external-priority patent/US4239768A/en

1978-12-22 Priority claimed from US05/972,579 external-priority patent/US4229462A/en

1979-12-21 Application filed by Mcneilab Inc filed Critical Mcneilab Inc

1980-06-24 Publication of NL7909265A publication Critical patent/NL7909265A/nl

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
-1 urea compound Chemical class 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 47
239000004202 carbamide Substances 0.000 claims description 39
239000000203 mixture Substances 0.000 claims description 38
238000000034 method Methods 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 32
238000002360 preparation method Methods 0.000 claims description 17
230000000968 intestinal effect Effects 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
DISXFZWKRTZTRI-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine Chemical compound NC1=NCCN1 DISXFZWKRTZTRI-UHFFFAOYSA-N 0.000 claims description 9
239000002552 dosage form Substances 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 claims description 2
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 65
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 34
235000013877 carbamide Nutrition 0.000 description 33
239000000047 product Substances 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 30
239000000243 solution Substances 0.000 description 29
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 17
239000007787 solid Substances 0.000 description 17
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 15
206010020772 Hypertension Diseases 0.000 description 14
238000012360 testing method Methods 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 13
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 13
239000002585 base Substances 0.000 description 12
238000000354 decomposition reaction Methods 0.000 description 12
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000012458 free base Substances 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
150000003672 ureas Chemical class 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
239000004480 active ingredient Substances 0.000 description 9
230000004872 arterial blood pressure Effects 0.000 description 9
239000007903 gelatin capsule Substances 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
239000012948 isocyanate Substances 0.000 description 9
235000019698 starch Nutrition 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000008107 starch Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
NRKTUPLYOCIVPP-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-amine;hydroiodide Chemical compound I.NC1=NCCN1 NRKTUPLYOCIVPP-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
230000037396 body weight Effects 0.000 description 7
239000002775 capsule Substances 0.000 description 7
238000009472 formulation Methods 0.000 description 7
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 7
229910000103 lithium hydride Inorganic materials 0.000 description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
230000003276 anti-hypertensive effect Effects 0.000 description 6
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 6
239000008116 calcium stearate Substances 0.000 description 6
235000013539 calcium stearate Nutrition 0.000 description 6
238000007796 conventional method Methods 0.000 description 6
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000011521 glass Substances 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
238000002156 mixing Methods 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012299 nitrogen atmosphere 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
239000012264 purified product Substances 0.000 description 4
210000000664 rectum Anatomy 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 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
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
230000009286 beneficial effect Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000007884 disintegrant Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
208000002551 irritable bowel syndrome Diseases 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
230000008961 swelling Effects 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
XFZJGFIKQCCLGK-UHFFFAOYSA-M 1,1-dimethyl-4-phenylpiperazinium iodide Chemical compound [I-].C1C[N+](C)(C)CCN1C1=CC=CC=C1 XFZJGFIKQCCLGK-UHFFFAOYSA-M 0.000 description 2
RSWXSBGLJUAXKD-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-2-ylurea Chemical compound NC(=O)NC1=NCCN1 RSWXSBGLJUAXKD-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
206010048964 Carotid artery occlusion Diseases 0.000 description 2
206010010774 Constipation Diseases 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 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
208000002193 Pain Diseases 0.000 description 2
241000700159 Rattus Species 0.000 description 2
241000283984 Rodentia Species 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
150000007513 acids Chemical class 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000001769 aryl amino group Chemical group 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
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
235000019700 dicalcium phosphate Nutrition 0.000 description 2
229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 2
230000002526 effect on cardiovascular system Effects 0.000 description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
210000003414 extremity Anatomy 0.000 description 2
239000001530 fumaric acid Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000000004 hemodynamic effect Effects 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000001631 hypertensive effect Effects 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
239000012022 methylating agents‎ Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
230000036407 pain Effects 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
239000006187 pill Substances 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
238000010992 reflux Methods 0.000 description 2
238000009738 saturating Methods 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
239000003826 tablet Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
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
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
WTABVQIXVUVUPO-UHFFFAOYSA-N 1-(4,5-dihydro-1h-imidazol-2-yl)-3-phenylurea Chemical compound N1CCNC1=NC(=O)NC1=CC=CC=C1 WTABVQIXVUVUPO-UHFFFAOYSA-N 0.000 description 1
FBTQQNYGMICJQZ-UHFFFAOYSA-N 1-chloro-2-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(Cl)=C1N=C=O FBTQQNYGMICJQZ-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
SUVCZZADQDCIEQ-UHFFFAOYSA-N 1-isocyanato-2-methoxybenzene Chemical compound COC1=CC=CC=C1N=C=O SUVCZZADQDCIEQ-UHFFFAOYSA-N 0.000 description 1
UCCQXCFFHYCLEC-UHFFFAOYSA-N 1-quinolin-2-ylethanone Chemical compound C1=CC=CC2=NC(C(=O)C)=CC=C21 UCCQXCFFHYCLEC-UHFFFAOYSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
IOTWODZNCCCZHL-UHFFFAOYSA-N 2-amino-4,5-dihydroimidazole-1-carboxylic acid Chemical compound NC1=NCCN1C(O)=O IOTWODZNCCCZHL-UHFFFAOYSA-N 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
CROBLTRUKGNQGK-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;hydroiodide Chemical compound I.C1CN=CN1 CROBLTRUKGNQGK-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
102000015427 Angiotensins Human genes 0.000 description 1
108010064733 Angiotensins Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
CHHIJDJBFMPYRK-UHFFFAOYSA-N Cl.ClC1=C(C=CC=C1)NC(=O)N=C1NCCN1 Chemical compound Cl.ClC1=C(C=CC=C1)NC(=O)N=C1NCCN1 CHHIJDJBFMPYRK-UHFFFAOYSA-N 0.000 description 1
VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000010496 Heart Arrest Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920003091 Methocel™ Polymers 0.000 description 1
UFBUJVYYRKZXDL-UHFFFAOYSA-N NC(=O)N.N1CNCCC1 Chemical compound NC(=O)N.N1CNCCC1 UFBUJVYYRKZXDL-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
101150052863 THY1 gene Proteins 0.000 description 1
KHGOQBXPPQSAHA-UHFFFAOYSA-N [N]C(N)=N Chemical group [N]C(N)=N KHGOQBXPPQSAHA-UHFFFAOYSA-N 0.000 description 1
210000001015 abdomen Anatomy 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000003113 alkalizing effect Effects 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
229940030600 antihypertensive agent Drugs 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
238000003556 assay Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
210000003403 autonomic nervous system Anatomy 0.000 description 1
229940077388 benzenesulfonate Drugs 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
230000002146 bilateral effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
UMGDCJDMYOKAJW-UHFFFAOYSA-M carbamimidothioate Chemical compound NC([S-])=N UMGDCJDMYOKAJW-UHFFFAOYSA-M 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
210000001168 carotid artery common Anatomy 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
239000003086 colorant Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
229960004486 desoxycorticosterone acetate Drugs 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
238000000921 elemental analysis Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
210000005224 forefinger Anatomy 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005286 illumination Methods 0.000 description 1
ATYGMDZIBQHJFX-UHFFFAOYSA-N imidazolidine;urea Chemical compound NC(N)=O.C1CNCN1 ATYGMDZIBQHJFX-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
229940049920 malate Drugs 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
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
229960002455 methoxyflurane Drugs 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 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
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000003755 preservative agent 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
230000010349 pulsation Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
210000001991 scapula Anatomy 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000011699 spontaneously hypertensive rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000006467 substitution reaction Methods 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
230000000153 supplemental effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
229960000340 thiopental sodium 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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000001515 vagal effect Effects 0.000 description 1
210000001186 vagus nerve Anatomy 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
230000009278 visceral effect Effects 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

NL7909265A 1978-12-22 1979-12-21 N-aryl-n'-(2-imidazolidinylideen)-ureumderivaten, alsmede farmaceutische preparaten, die deze derivaten bevatten. NL7909265A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/972,580 US4239768A (en)	1978-12-22	1978-12-22	Method for relieving irritable bowel syndrome symptoms
US97258078		1978-12-22
US05/972,579 US4229462A (en)	1978-12-22	1978-12-22	Method for controlling hypertension and compositions
US97257978		1978-12-22

Publications (1)

Publication Number	Publication Date
NL7909265A true NL7909265A (nl)	1980-06-24

Family

ID=27130555

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7909265A NL7909265A (nl)	1978-12-22	1979-12-21	N-aryl-n'-(2-imidazolidinylideen)-ureumderivaten, alsmede farmaceutische preparaten, die deze derivaten bevatten.

Country Status (23)

Country	Link
AT (1)	AT373878B (it)
AU (2)	AU532332B2 (it)
CA (1)	CA1127651A (it)
CH (1)	CH647236A5 (it)
DE (1)	DE2951213A1 (it)
DK (1)	DK548179A (it)
ES (1)	ES487159A0 (it)
FI (1)	FI66354C (it)
FR (2)	FR2444462B1 (it)
GB (2)	GB2040681B (it)
GR (1)	GR68018B (it)
HU (1)	HU183013B (it)
IL (1)	IL59019A (it)
IT (1)	IT1126839B (it)
NL (1)	NL7909265A (it)
NO (1)	NO794249L (it)
NZ (1)	NZ192453A (it)
PH (1)	PH16571A (it)
PT (1)	PT70624A (it)
SE (1)	SE7910612L (it)
SU (1)	SU971098A3 (it)
YU (1)	YU314979A (it)
ZW (1)	ZW25379A1 (it)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20200137557A1 (en) *	2018-10-29	2020-04-30	Apple Inc.	Mechanism to Activate and Manage a Standalone Device for Cellular Service

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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
NL267923A (it) *	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 AU AU53780/79A patent/AU532332B2/en not_active Ceased
- 1979-12-13 PH PH23413A patent/PH16571A/en unknown
- 1979-12-18 NZ NZ192453A patent/NZ192453A/xx unknown
- 1979-12-19 DE DE19792951213 patent/DE2951213A1/de not_active Ceased
- 1979-12-20 ES ES487159A patent/ES487159A0/es active Granted
- 1979-12-20 DK DK548179A patent/DK548179A/da not_active Application Discontinuation
- 1979-12-21 FR FR7931473A patent/FR2444462B1/fr not_active Expired
- 1979-12-21 PT PT70624A patent/PT70624A/pt unknown
- 1979-12-21 NL NL7909265A patent/NL7909265A/nl not_active Application Discontinuation
- 1979-12-21 SE SE7910612A patent/SE7910612L/xx not_active Application Discontinuation
- 1979-12-21 NO NO794249A patent/NO794249L/no unknown
- 1979-12-21 GB GB7944114A patent/GB2040681B/en not_active Expired
- 1979-12-21 IL IL59019A patent/IL59019A/xx unknown
- 1979-12-21 YU YU03149/79A patent/YU314979A/xx unknown
- 1979-12-21 IT IT51164/79A patent/IT1126839B/it active
- 1979-12-21 CH CH11419/79A patent/CH647236A5/de not_active IP Right Cessation
- 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 ZW ZW253/79A patent/ZW25379A1/xx unknown
- 1979-12-21 AT AT0808979A patent/AT373878B/de active
- 1979-12-21 SU SU792860905A patent/SU971098A3/ru active
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

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20200137557A1 (en) *	2018-10-29	2020-04-30	Apple Inc.	Mechanism to Activate and Manage a Standalone Device for Cellular Service
US11516649B2 (en) *	2018-10-29	2022-11-29	Apple Inc.	Mechanism to activate and manage a standalone device for cellular service
US11770695B2 (en)	2018-10-29	2023-09-26	Apple Inc.	Mechanism to activate and manage a standalone device for cellular service

Also Published As

Publication number	Publication date
ES8101558A1 (es)	1980-12-16
ATA808979A (de)	1983-07-15
AU1640083A (en)	1983-11-17
FR2444462B1 (fr)	1986-08-29
GB2113204B (en)	1984-02-01
GB2040681A (en)	1980-09-03
DK548179A (da)	1980-06-23
GB2113204A (en)	1983-08-03
SE7910612L (sv)	1980-06-23
FI66354C (fi)	1984-10-10
HU183013B (en)	1984-04-28
PT70624A (en)	1980-01-01
FR2445321B1 (it)	1983-08-26
AT373878B (de)	1984-02-27
YU314979A (en)	1983-02-28
PH16571A (en)	1983-11-18
CH647236A5 (de)	1985-01-15
FI66354B (fi)	1984-06-29
NO794249L (no)	1980-06-24
IT1126839B (it)	1986-05-21
AU566013B2 (en)	1987-10-08
IL59019A (en)	1984-05-31
GR68018B (it)	1981-10-27
CA1127651A (en)	1982-07-13
IL59019A0 (en)	1980-03-31
SU971098A3 (ru)	1982-10-30
NZ192453A (en)	1982-09-07
FR2445321A1 (it)	1980-07-25
GB2040681B (en)	1983-04-13
AU532332B2 (en)	1983-09-29
FR2444462A1 (fr)	1980-07-18
ES487159A0 (es)	1980-12-16
IT7951164A0 (it)	1979-12-21
AU5378079A (en)	1980-06-26
ZW25379A1 (en)	1981-07-22
DE2951213A1 (de)	1980-07-10
FI794036A (fi)	1980-06-23

Publication	Publication Date	Title
US4057636A (en)	1977-11-08	Antihypertensive pyridylguanidine compounds
CZ282142B6 (cs)	1997-05-14	Cykloalkylsubstituované glutaramidové deriváty, farmaceutický prostředek obsahující tyto sloučeniny a použití
CZ62699A3 (cs)	1999-07-14	Heterocyklické inhibitory metaloproteinas
CN101421247A (zh)	2009-04-29	新的咪唑衍生物、其制备方法和其作为药物的用途
EP0029663B1 (en)	1984-04-18	N-aryl-n'-imidazol-2-ylureas, process for their preparation and pharmaceutical compositions containing them
EA008249B1 (ru)	2007-04-27	Новые пролекарства (n-2-пиридил-n-2-гидроксикарбонилэтил)амида 1-метил-2-(4-амидинофениламинометил)бензимидазол-5-илкарбоновой кислоты, их получение и их применение в качестве лекарственных средств
US4239768A (en)	1980-12-16	Method for relieving irritable bowel syndrome symptoms
NL7909265A (nl)	1980-06-24	N-aryl-n'-(2-imidazolidinylideen)-ureumderivaten, alsmede farmaceutische preparaten, die deze derivaten bevatten.
HUT70174A (en)	1995-09-28	New 3-phenyl-sulphonyl-3,7-diazabicyclo [3.3.1] nonane compounds and pharmaceutical compounds containing the same
US20040039045A1 (en)	2004-02-26	(2-azabicyclo[2.2.1]hept-7yl) methanol derivatives as nicotinic acetylcholine receptor agonists
DE2531829C2 (de)	1985-12-12	N-(3,4,5-Trimethoxycinnamoyl)-N'- (2'-pyrrolidinon-1'-carbonylmethyl) -piperazin, Verfahren zu dessen Herstellung und diese Verbindung enthaltende Arzneimittel
US4668683A (en)	1987-05-26	Cardiotonic quinazoline derivatives
US4229462A (en)	1980-10-21	Method for controlling hypertension and compositions
US3816531A (en)	1974-06-11	(2,6-disubstituted benzylidene)amino guanidines and related compounds
RU2404974C2 (ru)	2010-11-27	БРОМИД 1-(β-ФЕНИЛЭТИЛ)-4-АМИНО-1,2,4-ТРИАЗОЛИЯ (МТ), ОБЛАДАЮЩИЙ КАРДИОПРОТЕКТИВНЫМ, ПРОТИВОИШЕМИЧЕСКИМ, АНТИГИПЕРТЕНЗИВНЫМ, АНТИОКСИДАНТНЫМ, ПРОТЕИНСИНТЕТИЧЕСКИМ И ЭНЕРГОТРОПНЫМ ДЕЙСТВИЕМ
GB2149395A (en)	1985-06-12	Amidines derived from 4-phenyl-2-substituted imidazoles
JP2798628B2 (ja)	1998-09-17	癲癇治療用の５−アミノカルボニル−５Ｈ−ジベンゾ［ａ，ｄ］シクロヘプテン−５，１０−イミン
JPS5976083A (ja)	1984-04-28	ジヒドロピリジン類
US4298746A (en)	1981-11-03	N-(Substituted phenyl)-N'-(2-imidazolidinylidene)ureas
JPH02167277A (ja)	1990-06-27	新規なジアジン化合物
US4507304A (en)	1985-03-26	Use of 6-amino-5-pyrimidinecarbonitrile derivatives as cardiotonic agents
JPH01146820A (ja)	1989-06-08	イミダゾール−２−チオンカルボキサミドによる再潅流傷害の軽減法
KR840001709B1 (ko)	1984-10-16	N-아릴-n'-[(1, 4, 5, 6-테트라히드로피리미딘-2-일)및 (4, 5, 6, 7-테트라히드로-1-h-1, 3-디아제핀-2-일))우레아의 제조방법
GB2094300A (en)	1982-09-15	4-(5)-alkylmercaptoimidazole derivatives, a process for their production and medicaments containing these compounds
JPS634556B2 (it)	1988-01-29

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-02-02	BV	The patent application has lapsed