IL118925A - Guanidides of Cinnamic Acid Converted, Process for Their Preparation, Pharmaceuticals and Diagnostic Containers Containing Them - Google Patents

Guanidides of Cinnamic Acid Converted, Process for Their Preparation, Pharmaceuticals and Diagnostic Containers Containing Them

Info

Publication number: IL118925A
Authority: IL; Israel
Prior art keywords: carbon atoms; methyl; independently; phenyl; zero
Prior art date: 1995-07-26

Application number

IL11892596A

Other languages

English (en)

Hebrew (he)

Other versions

IL118925A0 (en

Original Assignee

Hmr Deutschland Gmbh

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.)

1995-07-26

Filing date

1996-07-24

Publication date

2001-08-08

1996-07-24 Application filed by Hmr Deutschland Gmbh filed Critical Hmr Deutschland Gmbh

1996-10-31 Publication of IL118925A0 publication Critical patent/IL118925A0/xx

2001-08-08 Publication of IL118925A publication Critical patent/IL118925A/en

Links

WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 title claims abstract description 10
229930016911 cinnamic acid Natural products 0.000 title claims abstract description 10
235000013985 cinnamic acid Nutrition 0.000 title claims abstract description 10
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 title claims abstract description 10
239000000203 mixture Substances 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 6
150000001851 cinnamic acid derivatives Chemical class 0.000 title claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 27
229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 18
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims abstract description 12
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 59
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 45
125000001424 substituent group Chemical group 0.000 claims description 37
238000011282 treatment Methods 0.000 claims description 23
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 20
239000003814 drug Substances 0.000 claims description 19
125000002947 alkylene group Chemical group 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
201000010099 disease Diseases 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 10
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
210000000056 organ Anatomy 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
238000011321 prophylaxis Methods 0.000 claims description 6
NMDBZDHDVOLPNH-SOFGYWHQSA-N (e)-3-[3-cyano-4-(dimethylamino)-2-fluorophenyl]-2-methylprop-2-enoic acid Chemical compound CN(C)C1=CC=C(\C=C(/C)C(O)=O)C(F)=C1C#N NMDBZDHDVOLPNH-SOFGYWHQSA-N 0.000 claims description 5
206010061216 Infarction Diseases 0.000 claims description 5
230000007574 infarction Effects 0.000 claims description 5
PYHURZFNUDZJCM-YRNVUSSQSA-N (e)-3-[2-[3-(dimethylamino)phenoxy]-4,6-difluorophenyl]-2-methylprop-2-enoic acid Chemical compound CN(C)C1=CC=CC(OC=2C(=C(F)C=C(F)C=2)\C=C(/C)C(O)=O)=C1 PYHURZFNUDZJCM-YRNVUSSQSA-N 0.000 claims description 4
WXLUBRDUMYJXKW-CMDGGOBGSA-N (e)-3-[4-(dimethylamino)phenyl]-2-methylprop-2-enoic acid Chemical compound CN(C)C1=CC=C(\C=C(/C)C(O)=O)C=C1 WXLUBRDUMYJXKW-CMDGGOBGSA-N 0.000 claims description 4
BWQLAIJPSLGFCQ-YRNVUSSQSA-N (e)-3-[4-[3-(dimethylamino)phenoxy]-2,6-difluorophenyl]-2-methylprop-2-enoic acid Chemical compound CN(C)C1=CC=CC(OC=2C=C(F)C(\C=C(/C)C(O)=O)=C(F)C=2)=C1 BWQLAIJPSLGFCQ-YRNVUSSQSA-N 0.000 claims description 4
230000005764 inhibitory process Effects 0.000 claims description 4
230000000302 ischemic effect Effects 0.000 claims description 4
KZDXCCDDHPMSAB-CSKARUKUSA-N (e)-2-methyl-3-[4-pyridin-4-ylsulfanyl-3-(trifluoromethyl)phenyl]prop-2-enoic acid Chemical compound FC(F)(F)C1=CC(\C=C(/C)C(O)=O)=CC=C1SC1=CC=NC=C1 KZDXCCDDHPMSAB-CSKARUKUSA-N 0.000 claims description 3
LETDOLRTKJIRQX-JLHYYAGUSA-N (e)-3-[4-[3-(dimethylamino)propoxy]phenyl]-2-fluoroprop-2-enoic acid Chemical compound CN(C)CCCOC1=CC=C(\C=C(\F)C(O)=O)C=C1 LETDOLRTKJIRQX-JLHYYAGUSA-N 0.000 claims description 3
YNMHBFSSOSTOKW-VAWYXSNFSA-N (e)-3-[4-[3-(dimethylamino)propoxy]phenyl]-2-methylprop-2-enoic acid Chemical compound CN(C)CCCOC1=CC=C(\C=C(/C)C(O)=O)C=C1 YNMHBFSSOSTOKW-VAWYXSNFSA-N 0.000 claims description 3
206010020772 Hypertension Diseases 0.000 claims description 3
206010003119 arrhythmia Diseases 0.000 claims description 3
230000000747 cardiac effect Effects 0.000 claims description 3
230000004663 cell proliferation Effects 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
206010020718 hyperplasia Diseases 0.000 claims description 3
230000002093 peripheral effect Effects 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
210000002307 prostate Anatomy 0.000 claims description 3
230000035939 shock Effects 0.000 claims description 3
SYPNHCINGOJLTP-JXMROGBWSA-N (E)-2-methyl-3-[4-pyridin-3-yloxy-3-(trifluoromethyl)phenyl]prop-2-enoic acid Chemical compound FC(F)(F)C1=CC(\C=C(/C)C(O)=O)=CC=C1OC1=CC=CN=C1 SYPNHCINGOJLTP-JXMROGBWSA-N 0.000 claims description 2
WANHNFSQYCVIQA-OVCLIPMQSA-N (e)-3-[4-[3-(dimethylamino)phenoxy]-3,5-difluorophenyl]-2-fluoroprop-2-enoic acid Chemical compound CN(C)C1=CC=CC(OC=2C(=CC(\C=C(\F)C(O)=O)=CC=2F)F)=C1 WANHNFSQYCVIQA-OVCLIPMQSA-N 0.000 claims description 2
206010002383 Angina Pectoris Diseases 0.000 claims description 2
206010008190 Cerebrovascular accident Diseases 0.000 claims description 2
208000002249 Diabetes Complications Diseases 0.000 claims description 2
206010012655 Diabetic complications Diseases 0.000 claims description 2
206010019668 Hepatic fibrosis Diseases 0.000 claims description 2
206010028980 Neoplasm Diseases 0.000 claims description 2
208000006011 Stroke Diseases 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
230000000879 anti-atherosclerotic effect Effects 0.000 claims description 2
201000011510 cancer Diseases 0.000 claims description 2
230000003176 fibrotic effect Effects 0.000 claims description 2
230000002062 proliferating effect Effects 0.000 claims description 2
208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
201000002793 renal fibrosis Diseases 0.000 claims description 2
230000006793 arrhythmia Effects 0.000 claims 2
210000003169 central nervous system Anatomy 0.000 claims 1
238000003745 diagnosis Methods 0.000 claims 1
210000001428 peripheral nervous system Anatomy 0.000 claims 1
238000004321 preservation Methods 0.000 claims 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 abstract description 6
125000003342 alkenyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
150000002148 esters Chemical class 0.000 description 15
-1 phenylthio, methylthio Chemical group 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
239000002904 solvent Substances 0.000 description 13
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 11
229960002576 amiloride Drugs 0.000 description 10
239000012230 colorless oil Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
210000003743 erythrocyte Anatomy 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000007787 solid Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
230000003288 anthiarrhythmic effect Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
238000009472 formulation Methods 0.000 description 4
230000004941 influx Effects 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 3
244000166550 Strophanthus gratus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 3
229960003343 ouabain Drugs 0.000 description 3
NLAVHUUABUFSIG-UHFFFAOYSA-N 3,4,5-trifluorobenzaldehyde Chemical compound FC1=CC(C=O)=CC(F)=C1F NLAVHUUABUFSIG-UHFFFAOYSA-N 0.000 description 2
MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 2
RXMUPNVSYKGKMY-UHFFFAOYSA-N 3-amino-6-chloro-n-(diaminomethylidene)-5-(dimethylamino)pyrazine-2-carboxamide Chemical compound CN(C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl RXMUPNVSYKGKMY-UHFFFAOYSA-N 0.000 description 2
GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 2
ZYOHTXKOHWSJMZ-UHFFFAOYSA-N 4-[3-(dimethylamino)propoxy]benzaldehyde Chemical compound CN(C)CCCOC1=CC=C(C=O)C=C1 ZYOHTXKOHWSJMZ-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
201000001320 Atherosclerosis Diseases 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
208000007530 Essential hypertension Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
206010020880 Hypertrophy Diseases 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
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WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
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QDERNBXNXJCIQK-UHFFFAOYSA-N ethylisopropylamiloride Chemical compound CCN(C(C)C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl QDERNBXNXJCIQK-UHFFFAOYSA-N 0.000 description 2
238000010265 fast atom bombardment Methods 0.000 description 2
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239000008103 glucose Substances 0.000 description 2
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125000002883 imidazolyl group Chemical group 0.000 description 2
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QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
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125000003373 pyrazinyl group Chemical group 0.000 description 2
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125000004076 pyridyl group Chemical group 0.000 description 2
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239000005720 sucrose Substances 0.000 description 2
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
UKCKEVADDBGTIP-YRNVUSSQSA-N (e)-3-[4-[3-(dimethylamino)phenoxy]-3,5-difluorophenyl]-2-methylprop-2-enoic acid Chemical compound CN(C)C1=CC=CC(OC=2C(=CC(\C=C(/C)C(O)=O)=CC=2F)F)=C1 UKCKEVADDBGTIP-YRNVUSSQSA-N 0.000 description 1
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FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical compound SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
KPJIEPBITZLHPQ-UHFFFAOYSA-N 2,4,6-trifluorobenzaldehyde Chemical compound FC1=CC(F)=C(C=O)C(F)=C1 KPJIEPBITZLHPQ-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
BIUDHHGROGJSHN-UHFFFAOYSA-N 4-fluoro-3-(trifluoromethyl)benzaldehyde Chemical compound FC1=CC=C(C=O)C=C1C(F)(F)F BIUDHHGROGJSHN-UHFFFAOYSA-N 0.000 description 1
UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
ZGQREXNGDAXSQI-UHFFFAOYSA-N 6-(dimethylamino)-2-fluoro-3-formylbenzonitrile Chemical compound CN(C)C1=CC=C(C=O)C(F)=C1C#N ZGQREXNGDAXSQI-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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
- 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
- A61P9/06—Antiarrhythmics
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Pulmonology (AREA)
Reproductive Health (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

IL11892596A 1995-07-26 1996-07-24 Guanidides of Cinnamic Acid Converted, Process for Their Preparation, Pharmaceuticals and Diagnostic Containers Containing Them IL118925A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19527305A DE19527305A1 (de)	1995-07-26	1995-07-26	Substituierte Zimtsäureguanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament

Publications (2)

Publication Number	Publication Date
IL118925A0 IL118925A0 (en)	1996-10-31
IL118925A true IL118925A (en)	2001-08-08

Family

ID=7767840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11892596A IL118925A (en)	1995-07-26	1996-07-24	Guanidides of Cinnamic Acid Converted, Process for Their Preparation, Pharmaceuticals and Diagnostic Containers Containing Them

Country Status (29)

Country	Link
US (1)	US5883133A (pl)
EP (1)	EP0755919B1 (pl)
JP (1)	JP4177466B2 (pl)
KR (1)	KR970006281A (pl)
CN (1)	CN1062554C (pl)
AR (1)	AR003467A1 (pl)
AT (1)	ATE186720T1 (pl)
AU (1)	AU704461B2 (pl)
BR (1)	BR9603179A (pl)
CA (1)	CA2182062C (pl)
CZ (1)	CZ289327B6 (pl)
DE (2)	DE19527305A1 (pl)
DK (1)	DK0755919T3 (pl)
ES (1)	ES2140765T3 (pl)
GR (1)	GR3032363T3 (pl)
HR (1)	HRP960356B1 (pl)
HU (1)	HUP9602072A3 (pl)
IL (1)	IL118925A (pl)
MX (1)	MX9603004A (pl)
MY (1)	MY115466A (pl)
NO (1)	NO306060B1 (pl)
NZ (1)	NZ299052A (pl)
PL (1)	PL183439B1 (pl)
RU (1)	RU2190601C2 (pl)
SI (1)	SI0755919T1 (pl)
SK (1)	SK282018B6 (pl)
TR (1)	TR199600612A2 (pl)
TW (1)	TW536531B (pl)
ZA (1)	ZA966313B (pl)

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1995
- 1995-07-26 DE DE19527305A patent/DE19527305A1/de not_active Withdrawn
1996
- 1996-05-16 PL PL96314279A patent/PL183439B1/pl unknown
- 1996-07-19 DE DE59603659T patent/DE59603659D1/de not_active Expired - Lifetime
- 1996-07-19 SI SI9630144T patent/SI0755919T1/xx unknown
- 1996-07-19 EP EP96111665A patent/EP0755919B1/de not_active Expired - Lifetime
- 1996-07-19 ES ES96111665T patent/ES2140765T3/es not_active Expired - Lifetime
- 1996-07-19 AT AT96111665T patent/ATE186720T1/de not_active IP Right Cessation
- 1996-07-19 DK DK96111665T patent/DK0755919T3/da active
- 1996-07-23 CN CN96110200A patent/CN1062554C/zh not_active Expired - Fee Related
- 1996-07-24 CZ CZ19962184A patent/CZ289327B6/cs not_active IP Right Cessation
- 1996-07-24 MY MYPI96003033A patent/MY115466A/en unknown
- 1996-07-24 IL IL11892596A patent/IL118925A/en not_active IP Right Cessation
- 1996-07-24 TR TR96/00612A patent/TR199600612A2/xx unknown
- 1996-07-24 US US08/686,999 patent/US5883133A/en not_active Expired - Lifetime
- 1996-07-24 NZ NZ299052A patent/NZ299052A/en unknown
- 1996-07-24 AR ARP960103724A patent/AR003467A1/es unknown
- 1996-07-24 AU AU60668/96A patent/AU704461B2/en not_active Ceased
- 1996-07-24 SK SK965-96A patent/SK282018B6/sk unknown
- 1996-07-25 MX MX9603004A patent/MX9603004A/es not_active IP Right Cessation
- 1996-07-25 BR BR9603179-4A patent/BR9603179A/pt unknown
- 1996-07-25 HR HR19527305.2 patent/HRP960356B1/xx not_active IP Right Cessation
- 1996-07-25 JP JP19628396A patent/JP4177466B2/ja not_active Expired - Fee Related
- 1996-07-25 NO NO963108A patent/NO306060B1/no unknown
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- 1996-07-25 RU RU96115333/04A patent/RU2190601C2/ru not_active IP Right Cessation
- 1996-07-25 ZA ZA9606313A patent/ZA966313B/xx unknown
- 1996-07-26 HU HU9602072A patent/HUP9602072A3/hu unknown
- 1996-07-26 KR KR1019960031743A patent/KR970006281A/ko not_active Ceased
- 1996-08-23 TW TW085110279A patent/TW536531B/zh active
2000
- 2000-01-14 GR GR20000400061T patent/GR3032363T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
SI0755919T1 (en)	2000-04-30
HRP960356B1 (en)	2001-02-28
EP0755919A3 (de)	1997-04-09
RU2190601C2 (ru)	2002-10-10
NO306060B1 (no)	1999-09-13
EP0755919B1 (de)	1999-11-17
PL314279A1 (en)	1997-02-03
GR3032363T3 (en)	2000-04-27
HUP9602072A3 (en)	1997-10-28
CA2182062A1 (en)	1997-01-27
NO963108L (no)	1997-01-27
IL118925A0 (en)	1996-10-31
SK96596A3 (en)	1997-03-05
AU6066896A (en)	1997-01-30
SK282018B6 (sk)	2001-10-08
ZA966313B (en)	1997-02-11
JPH0952823A (ja)	1997-02-25
CN1062554C (zh)	2001-02-28
JP4177466B2 (ja)	2008-11-05
NO963108D0 (no)	1996-07-25
CN1145899A (zh)	1997-03-26
DE19527305A1 (de)	1997-01-30
MY115466A (en)	2003-06-30
CZ289327B6 (cs)	2002-01-16
HRP960356A2 (en)	1998-02-28
NZ299052A (en)	1997-10-24
CA2182062C (en)	2008-12-02
DE59603659D1 (de)	1999-12-23
DK0755919T3 (da)	2000-04-25
AR003467A1 (es)	1998-08-05
HU9602072D0 (en)	1996-09-30
HUP9602072A2 (en)	1997-05-28
TW536531B (en)	2003-06-11
PL183439B1 (pl)	2002-06-28
TR199600612A2 (tr)	1997-04-22
AU704461B2 (en)	1999-04-22
ATE186720T1 (de)	1999-12-15
US5883133A (en)	1999-03-16
BR9603179A (pt)	2002-04-09
MX9603004A (es)	1997-01-31
KR970006281A (ko)	1997-02-19
ES2140765T3 (es)	2000-03-01
EP0755919A2 (de)	1997-01-29
CZ218496A3 (en)	1997-02-12

Legal Events

Date	Code	Title
2002-02-10	FF	Patent granted
2002-02-10	KB	Patent renewed
2002-08-14	KB	Patent renewed
2007-05-21	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
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US5998481A (en)	1999-12-07	Fluoroalkyl/alkenyl-substituted benzoylguanidines, process for their preparation, their use as a medicament or diagnostic, and medicament containing them
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