NO791334L - Fremgangsmaate ved fremstilling av 1,3-diaryl-2-imino-imidazolidiner og -2-imino-hexahydro-pyrimidiner - Google Patents
Fremgangsmaate ved fremstilling av 1,3-diaryl-2-imino-imidazolidiner og -2-imino-hexahydro-pyrimidinerInfo
- Publication number
- NO791334L NO791334L NO791334A NO791334A NO791334L NO 791334 L NO791334 L NO 791334L NO 791334 A NO791334 A NO 791334A NO 791334 A NO791334 A NO 791334A NO 791334 L NO791334 L NO 791334L
- Authority
- NO
- Norway
- Prior art keywords
- dimethylphenyl
- bis
- imidazolidine
- imino
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 94
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 182
- 239000000203 mixture Substances 0.000 claims description 142
- -1 alkyl mercaptan Chemical compound 0.000 claims description 72
- 150000003839 salts Chemical class 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 239000012458 free base Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 230000002269 spontaneous effect Effects 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
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- 229910003439 heavy metal oxide Inorganic materials 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims 1
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- 239000002904 solvent Substances 0.000 description 67
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- 238000009835 boiling Methods 0.000 description 14
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
- KIBVDRZUDMEICL-UHFFFAOYSA-N 1,3-bis(2,6-dimethylphenyl)-4-methylimidazolidin-2-imine Chemical compound CC1CN(C=2C(=CC=CC=2C)C)C(=N)N1C1=C(C)C=CC=C1C KIBVDRZUDMEICL-UHFFFAOYSA-N 0.000 description 13
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- 239000005457 ice water Substances 0.000 description 11
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- 238000001665 trituration Methods 0.000 description 6
- XSCJHBKXZRSMID-UHFFFAOYSA-N 1,3-bis(2,6-dimethylphenyl)imidazolidin-2-imine Chemical compound CC1=CC=CC(C)=C1N1C(=N)N(C=2C(=CC=CC=2C)C)CC1 XSCJHBKXZRSMID-UHFFFAOYSA-N 0.000 description 5
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- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical compound CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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- XTDYIZVGVRUPAT-HDICACEKSA-N (4s,5r)-1,3-bis(2,6-dimethylphenyl)-4,5-dimethylimidazolidin-2-imine Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)[C@@H]1C)C(=N)N1C1=C(C)C=CC=C1C XTDYIZVGVRUPAT-HDICACEKSA-N 0.000 description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
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- 239000002934 diuretic Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 1
- LSISGIQUTXDTGR-UHFFFAOYSA-N ethyl n-[1,3-bis(2,3-dimethylphenyl)-4-methylimidazolidin-2-ylidene]carbamate Chemical compound CCOC(=O)N=C1N(C=2C(=C(C)C=CC=2)C)CC(C)N1C1=CC=CC(C)=C1C LSISGIQUTXDTGR-UHFFFAOYSA-N 0.000 description 1
- LZBNYBQARHSHLM-UHFFFAOYSA-N ethyl n-[1,3-bis(2,6-dimethylphenyl)-1,3-diazinan-2-ylidene]carbamate Chemical compound CCOC(=O)N=C1N(C=2C(=CC=CC=2C)C)CCCN1C1=C(C)C=CC=C1C LZBNYBQARHSHLM-UHFFFAOYSA-N 0.000 description 1
- GQCSFBNHXOLWHV-UHFFFAOYSA-N ethyl n-[1,3-bis(2,6-dimethylphenyl)-4,4-dimethylimidazolidin-2-ylidene]carbamate Chemical compound CCOC(=O)N=C1N(C=2C(=CC=CC=2C)C)CC(C)(C)N1C1=C(C)C=CC=C1C GQCSFBNHXOLWHV-UHFFFAOYSA-N 0.000 description 1
- ZTPCQRZRLRLPRW-UHFFFAOYSA-N ethyl n-[1,3-bis(2,6-dimethylphenyl)-4-methylimidazolidin-2-ylidene]carbamate Chemical compound CCOC(=O)N=C1N(C=2C(=CC=CC=2C)C)CC(C)N1C1=C(C)C=CC=C1C ZTPCQRZRLRLPRW-UHFFFAOYSA-N 0.000 description 1
- JOVIQDMGBIOLCO-UHFFFAOYSA-N ethyl n-[1,3-bis(2,6-dimethylphenyl)imidazolidin-2-ylidene]carbamate Chemical compound CCOC(=O)N=C1N(C=2C(=CC=CC=2C)C)CCN1C1=C(C)C=CC=C1C JOVIQDMGBIOLCO-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
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- 230000003054 hormonal effect Effects 0.000 description 1
- 231100000508 hormonal effect Toxicity 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- VQYJLACQFYZHCO-UHFFFAOYSA-N hydron;4-methoxyaniline;chloride Chemical compound [Cl-].COC1=CC=C([NH3+])C=C1 VQYJLACQFYZHCO-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- GVONPBONFIJAHJ-UHFFFAOYSA-N imidazolidin-4-one Chemical class O=C1CNCN1 GVONPBONFIJAHJ-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 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
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- NCPLUGNIQNZQAU-UHFFFAOYSA-N methyl 1,3-bis(2,6-dimethylphenyl)-2-iminoimidazolidine-4-carboxylate Chemical compound COC(=O)C1CN(C=2C(=CC=CC=2C)C)C(=N)N1C1=C(C)C=CC=C1C NCPLUGNIQNZQAU-UHFFFAOYSA-N 0.000 description 1
- XITYUVOGOAHCCK-UHFFFAOYSA-N methyl 1,3-bis(2,6-dimethylphenyl)-2-iminoimidazolidine-4-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1CN(C=2C(=CC=CC=2C)C)C(=N)N1C1=C(C)C=CC=C1C XITYUVOGOAHCCK-UHFFFAOYSA-N 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical class CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- XMIRKIQYGLZKQT-UHFFFAOYSA-N n,n'-bis(2,3-dimethylphenyl)ethane-1,2-diamine Chemical compound CC1=CC=CC(NCCNC=2C(=C(C)C=CC=2)C)=C1C XMIRKIQYGLZKQT-UHFFFAOYSA-N 0.000 description 1
- MUTOPNNRGLGXRJ-UHFFFAOYSA-N n,n'-bis(2,6-dimethylphenyl)propane-1,3-diamine Chemical compound CC1=CC=CC(C)=C1NCCCNC1=C(C)C=CC=C1C MUTOPNNRGLGXRJ-UHFFFAOYSA-N 0.000 description 1
- WPXNHSRXGYBXNL-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=C(C)C=CC=C1C WPXNHSRXGYBXNL-UHFFFAOYSA-N 0.000 description 1
- SGGZJYMMHBBKDN-UHFFFAOYSA-N n-[1,3-bis(2,6-dimethylphenyl)imidazolidin-2-ylidene]benzamide Chemical compound CC1=CC=CC(C)=C1N(CCN1C=2C(=CC=CC=2C)C)C1=NC(=O)C1=CC=CC=C1 SGGZJYMMHBBKDN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- NIQWUFFVVUCQQN-UHFFFAOYSA-N phenyl n-[1,3-bis(2,6-dimethylphenyl)-4-methylimidazolidin-2-ylidene]carbamate Chemical compound CC=1C=CC=C(C)C=1N1C(C)CN(C=2C(=CC=CC=2C)C)C1=NC(=O)OC1=CC=CC=C1 NIQWUFFVVUCQQN-UHFFFAOYSA-N 0.000 description 1
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical compound N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 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 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- KKKDGYXNGYJJRX-UHFFFAOYSA-M silver nitrite Chemical compound [Ag+].[O-]N=O KKKDGYXNGYJJRX-UHFFFAOYSA-M 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Inorganic materials [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
- 229960002256 spironolactone Drugs 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000723 toxicological property Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MYDCBDCRXHZOFQ-UHFFFAOYSA-N triphenylphosphane dihydroiodide Chemical compound I.I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MYDCBDCRXHZOFQ-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 230000036325 urinary excretion Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/18—Nitrogen atoms not forming part of a nitro radical with hetero atoms attached to said nitrogen atoms, except nitro radicals, e.g. hydrazine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
- C07D233/46—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms attached to said nitrogen 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
- C07D233/48—Nitrogen atoms not forming part of a nitro radical with acyclic hydrocarbon or substituted acyclic hydrocarbon radicals, attached to said nitrogen 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
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C07D239/14—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D247/00—Heterocyclic compounds containing rings having two nitrogen atoms as the only ring hetero atoms, according to more than one of groups C07D229/00 - C07D245/00
- C07D247/02—Heterocyclic compounds containing rings having two nitrogen atoms as the only ring hetero atoms, according to more than one of groups C07D229/00 - C07D245/00 having the nitrogen atoms in positions 1 and 3
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24C—DOMESTIC STOVES OR RANGES ; DETAILS OF DOMESTIC STOVES OR RANGES, OF GENERAL APPLICATION
- F24C15/00—Details
- F24C15/10—Tops, e.g. hot plates; Rings
- F24C15/101—Tops, e.g. hot plates; Rings provisions for circulation of air
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24C—DOMESTIC STOVES OR RANGES ; DETAILS OF DOMESTIC STOVES OR RANGES, OF GENERAL APPLICATION
- F24C3/00—Stoves or ranges for gaseous fuels
- F24C3/04—Stoves or ranges for gaseous fuels with heat produced wholly or partly by a radiant body, e.g. by a perforated plate
- F24C3/047—Ranges
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Combustion & Propulsion (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU78GO1400A HU180240B (en) | 1978-04-21 | 1978-04-21 | Process for producing new,substituted 1,3-diaryl-2-iminoimidasolidines and 2-imino-hexahydro-pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO791334L true NO791334L (no) | 1979-10-23 |
Family
ID=10996854
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO791334A NO791334L (no) | 1978-04-21 | 1979-04-20 | Fremgangsmaate ved fremstilling av 1,3-diaryl-2-imino-imidazolidiner og -2-imino-hexahydro-pyrimidiner |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4284642A (fr) |
| JP (1) | JPS54154765A (fr) |
| AU (1) | AU4622079A (fr) |
| BE (1) | BE875695A (fr) |
| CA (1) | CA1110626A (fr) |
| DD (1) | DD143255A5 (fr) |
| DE (1) | DE2916140A1 (fr) |
| DK (1) | DK163379A (fr) |
| ES (1) | ES479707A1 (fr) |
| FI (1) | FI791289A7 (fr) |
| FR (1) | FR2423485A1 (fr) |
| GB (1) | GB2022577B (fr) |
| HU (1) | HU180240B (fr) |
| IL (1) | IL57081A0 (fr) |
| IT (1) | IT1166756B (fr) |
| NL (1) | NL7903129A (fr) |
| NO (1) | NO791334L (fr) |
| PL (1) | PL126933B1 (fr) |
| SE (1) | SE7903450L (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU191408B (en) * | 1984-04-25 | 1987-02-27 | Egis Gyogyszergyar,Hu | Process for preparing new imino-thiazolidine derivatives |
| JPH0784461B2 (ja) * | 1986-12-19 | 1995-09-13 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロイミノ又はシアノイミノ化合物 |
| US5385946A (en) * | 1986-07-10 | 1995-01-31 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Method for treating hypertension with disubstituted granidine compounds |
| US5312840A (en) * | 1986-07-10 | 1994-05-17 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US5574070A (en) * | 1990-05-25 | 1996-11-12 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | Substituted guanidines having high binding to the sigma receptor and the use thereof |
| US6025355A (en) | 1997-05-19 | 2000-02-15 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| US6242198B1 (en) | 1996-07-25 | 2001-06-05 | Cambridge Neuroscience, Inc. | Methods of treatment of eye trauma and disorders |
| US6756389B2 (en) | 1996-08-09 | 2004-06-29 | Cambridge Neuroscience, Inc. | Pharmaceutically active compounds and methods of use |
| DE10036121A1 (de) * | 2000-07-25 | 2002-02-07 | Merck Patent Gmbh | N-Substituierte-1-amino-1,1-dialkyl-carbonsäurederivate |
| DE10119423A1 (de) * | 2001-04-20 | 2002-10-24 | Bayer Ag | Neue insektizid wirkende Azole |
| NZ528961A (en) * | 2001-04-20 | 2005-04-29 | Bayer Cropscience Ag | Novel insecticidal azoles |
| WO2007066496A1 (fr) * | 2005-12-07 | 2007-06-14 | Sumitomo Chemical Company, Limited | Compose benzoyluree et son utilisation |
| EP2001853A1 (fr) * | 2006-03-24 | 2008-12-17 | NeuroSearch A/S | Nouveaux dérivés de guanidine et utilisation médicale de ceux-ci |
| WO2014139861A1 (fr) | 2013-03-11 | 2014-09-18 | Universität Bayreuth | Complexes pour l'oligomérisation catalytique d'oléfines |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2557911A (en) * | 1950-04-19 | 1951-06-19 | American Cyanamid Co | Method of preparing glycocyamidines |
| FR1185256A (fr) * | 1956-10-30 | 1959-07-31 | Chemie Linz Ag | Procédé de préparation de dérivés de l'imidazol |
-
1978
- 1978-04-21 HU HU78GO1400A patent/HU180240B/hu unknown
-
1979
- 1979-04-16 IL IL57081A patent/IL57081A0/xx unknown
- 1979-04-16 US US06/030,149 patent/US4284642A/en not_active Expired - Lifetime
- 1979-04-18 ES ES479707A patent/ES479707A1/es not_active Expired
- 1979-04-19 FI FI791289A patent/FI791289A7/fi not_active Application Discontinuation
- 1979-04-19 BE BE1/9360A patent/BE875695A/fr unknown
- 1979-04-19 SE SE7903450A patent/SE7903450L/xx not_active Application Discontinuation
- 1979-04-20 DE DE19792916140 patent/DE2916140A1/de not_active Withdrawn
- 1979-04-20 AU AU46220/79A patent/AU4622079A/en not_active Abandoned
- 1979-04-20 FR FR7909993A patent/FR2423485A1/fr not_active Withdrawn
- 1979-04-20 GB GB7913901A patent/GB2022577B/en not_active Expired
- 1979-04-20 JP JP4809379A patent/JPS54154765A/ja active Pending
- 1979-04-20 NL NL7903129A patent/NL7903129A/xx not_active Application Discontinuation
- 1979-04-20 DK DK163379A patent/DK163379A/da not_active IP Right Cessation
- 1979-04-20 NO NO791334A patent/NO791334L/no unknown
- 1979-04-20 CA CA325,989A patent/CA1110626A/fr not_active Expired
- 1979-04-21 DD DD79212402A patent/DD143255A5/de unknown
- 1979-04-21 PL PL1979215062A patent/PL126933B1/pl unknown
- 1979-04-23 IT IT22036/79A patent/IT1166756B/it active
-
1981
- 1981-08-11 US US06/292,002 patent/US4369325A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54154765A (en) | 1979-12-06 |
| US4284642A (en) | 1981-08-18 |
| DK163379A (da) | 1979-10-22 |
| DE2916140A1 (de) | 1979-10-31 |
| NL7903129A (nl) | 1979-10-23 |
| FI791289A7 (fi) | 1981-01-01 |
| IL57081A0 (en) | 1979-07-25 |
| PL126933B1 (en) | 1983-09-30 |
| SE7903450L (sv) | 1979-10-22 |
| GB2022577A (en) | 1979-12-19 |
| AU4622079A (en) | 1979-10-25 |
| PL215062A1 (fr) | 1980-03-24 |
| IT1166756B (it) | 1987-05-06 |
| US4369325A (en) | 1983-01-18 |
| FR2423485A1 (fr) | 1979-11-16 |
| CA1110626A (fr) | 1981-10-13 |
| BE875695A (fr) | 1979-10-19 |
| DD143255A5 (de) | 1980-08-13 |
| ES479707A1 (es) | 1980-08-16 |
| GB2022577B (en) | 1982-12-01 |
| IT7922036A0 (it) | 1979-04-23 |
| HU180240B (en) | 1983-02-28 |
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