KR19980069747A - 알킬렌디아민 유도체 및 항궤양제, 항균제 - Google Patents
알킬렌디아민 유도체 및 항궤양제, 항균제 Download PDFInfo
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- KR19980069747A KR19980069747A KR1019970015041A KR19970015041A KR19980069747A KR 19980069747 A KR19980069747 A KR 19980069747A KR 1019970015041 A KR1019970015041 A KR 1019970015041A KR 19970015041 A KR19970015041 A KR 19970015041A KR 19980069747 A KR19980069747 A KR 19980069747A
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- 125000005263 alkylenediamine group Chemical group 0.000 title claims abstract description 58
- 239000003699 antiulcer agent Substances 0.000 title claims abstract description 7
- 239000004599 antimicrobial Substances 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 229940037467 helicobacter pylori Drugs 0.000 claims abstract description 19
- 241000590002 Helicobacter pylori Species 0.000 claims abstract description 18
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 11
- 125000002350 geranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 229910052717 sulfur Chemical group 0.000 claims abstract description 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 49
- 230000002401 inhibitory effect Effects 0.000 claims description 14
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 8
- 208000011906 peptic ulcer disease Diseases 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 6
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 230000027119 gastric acid secretion Effects 0.000 claims description 4
- 201000005917 gastric ulcer Diseases 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000035755 proliferation Effects 0.000 claims description 2
- 208000025865 Ulcer Diseases 0.000 abstract description 22
- 230000000767 anti-ulcer Effects 0.000 abstract description 22
- 231100000397 ulcer Toxicity 0.000 abstract description 20
- 230000009471 action Effects 0.000 abstract description 18
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 10
- 239000000126 substance Substances 0.000 abstract description 7
- 230000002265 prevention Effects 0.000 abstract description 4
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 166
- 238000005160 1H NMR spectroscopy Methods 0.000 description 62
- 238000006243 chemical reaction Methods 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- -1 methoxy, ethoxy, n-propoxy, n- Propoxy, n-pentyloxy, 1-ethylpropoxy, isoamyloxy, n-hexyloxy Chemical group 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 230000015572 biosynthetic process Effects 0.000 description 33
- 238000012360 testing method Methods 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- 239000002904 solvent Substances 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000002253 acid Substances 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 26
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- RMDHZUUXNBGDEM-SDNWHVSQSA-N 4-[(2e)-3,7-dimethylocta-2,6-dienoxy]benzoic acid Chemical compound CC(C)=CCC\C(C)=C\COC1=CC=C(C(O)=O)C=C1 RMDHZUUXNBGDEM-SDNWHVSQSA-N 0.000 description 22
- 238000010992 reflux Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000003814 drug Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229940079593 drug Drugs 0.000 description 17
- JSCUZAYKVZXKQE-JXMROGBWSA-N (2e)-1-bromo-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CBr JSCUZAYKVZXKQE-JXMROGBWSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 16
- 230000009858 acid secretion Effects 0.000 description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 15
- 238000006482 condensation reaction Methods 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 210000002784 stomach Anatomy 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- ZMXJAEGJWHJMGX-UHFFFAOYSA-N methyl syringate Chemical compound COC(=O)C1=CC(OC)=C(O)C(OC)=C1 ZMXJAEGJWHJMGX-UHFFFAOYSA-N 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 231100000419 toxicity Toxicity 0.000 description 10
- 230000001988 toxicity Effects 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 150000008282 halocarbons Chemical class 0.000 description 8
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 8
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 230000002496 gastric effect Effects 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 235000015097 nutrients Nutrition 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- GKBNJOLVPRPWCD-SDNWHVSQSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienoxy]benzoic acid Chemical compound CC(C)=CCC\C(C)=C\COC1=CC=CC=C1C(O)=O GKBNJOLVPRPWCD-SDNWHVSQSA-N 0.000 description 5
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 239000012981 Hank's balanced salt solution Substances 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 229960000212 aminophenazone Drugs 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- YFBSBLHMAWUCJB-UHFFFAOYSA-N methyl syringate Natural products COc1cc(cc(OC)c1O)C(=O)OO YFBSBLHMAWUCJB-UHFFFAOYSA-N 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- TXEIWRZSXRAGMY-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-1-yl]ethanamine Chemical compound CC(C)CN1CCN(CCN)CC1 TXEIWRZSXRAGMY-UHFFFAOYSA-N 0.000 description 4
- JLVVDRNINQVVFZ-GXDHUFHOSA-N 3-[(2e)-3,7-dimethylocta-2,6-dienoxy]benzoic acid Chemical compound CC(C)=CCC\C(C)=C\COC1=CC=CC(C(O)=O)=C1 JLVVDRNINQVVFZ-GXDHUFHOSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- 102000029816 Collagenase Human genes 0.000 description 4
- 108060005980 Collagenase Proteins 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- QPQGTZMAQRXCJW-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)C1=CC=CC=C1 QPQGTZMAQRXCJW-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229960002424 collagenase Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000034994 death Effects 0.000 description 4
- 231100000517 death Toxicity 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- KBPUBCVJHFXPOC-UHFFFAOYSA-N ethyl 3,4-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC=C(O)C(O)=C1 KBPUBCVJHFXPOC-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- RNVFYQUEEMZKLR-UHFFFAOYSA-N methyl 3,5-dihydroxybenzoate Chemical compound COC(=O)C1=CC(O)=CC(O)=C1 RNVFYQUEEMZKLR-UHFFFAOYSA-N 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZVDZVJXBCJUADL-UHFFFAOYSA-N 2,4-diphenoxybenzoic acid Chemical compound C1=C(OC=2C=CC=CC=2)C(C(=O)O)=CC=C1OC1=CC=CC=C1 ZVDZVJXBCJUADL-UHFFFAOYSA-N 0.000 description 3
- SHUQIGHJQMJUHB-UHFFFAOYSA-N 2-(4-ethylpiperazin-1-yl)ethanamine Chemical compound CCN1CCN(CCN)CC1 SHUQIGHJQMJUHB-UHFFFAOYSA-N 0.000 description 3
- YANPIBDDDIMUJS-SDNWHVSQSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienoxy]-3-methoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1OC\C=C(/C)CCC=C(C)C YANPIBDDDIMUJS-SDNWHVSQSA-N 0.000 description 3
- RJUODSSXDRYAMA-GXDHUFHOSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienoxy]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC\C=C(/C)CCC=C(C)C)=C1 RJUODSSXDRYAMA-GXDHUFHOSA-N 0.000 description 3
- OVGGDFMHDWUVEI-UKTHLTGXSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienoxy]-5-fluorobenzoic acid Chemical compound CC(C)=CCC\C(C)=C\COC1=CC=C(F)C=C1C(O)=O OVGGDFMHDWUVEI-UKTHLTGXSA-N 0.000 description 3
- UGNICHAOVFMHBJ-GXDHUFHOSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienoxy]-5-methoxybenzoic acid Chemical compound COC1=CC=C(OC\C=C(/C)CCC=C(C)C)C(C(O)=O)=C1 UGNICHAOVFMHBJ-GXDHUFHOSA-N 0.000 description 3
- BQUJRDLWFVPLFS-SDNWHVSQSA-N 2-[(2e)-3,7-dimethylocta-2,6-dienyl]benzenecarbothioic s-acid Chemical compound CC(C)=CCC\C(C)=C\CC1=CC=CC=C1C(O)=S BQUJRDLWFVPLFS-SDNWHVSQSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- QWXFQFDBGQMTTL-QAOSGDJLSA-N 3,4-bis[(2e)-3,7-dimethylocta-2,6-dienoxy]benzoic acid Chemical compound CC(C)=CCC\C(C)=C\COC1=CC=C(C(O)=O)C=C1OC\C=C(/C)CCC=C(C)C QWXFQFDBGQMTTL-QAOSGDJLSA-N 0.000 description 3
- VZUNVSJCIKACNL-UHFFFAOYSA-N 3,5-dimethoxy-4-phenoxybenzoic acid Chemical compound COC=1C=C(C(=O)O)C=C(C=1OC1=CC=CC=C1)OC VZUNVSJCIKACNL-UHFFFAOYSA-N 0.000 description 3
- DMRRHKWKDVOJSB-UHFFFAOYSA-N 3,5-diphenoxybenzoic acid Chemical compound C=1C(OC=2C=CC=CC=2)=CC(C(=O)O)=CC=1OC1=CC=CC=C1 DMRRHKWKDVOJSB-UHFFFAOYSA-N 0.000 description 3
- YPBSBPWIYVSLNE-NTEUORMPSA-N 3-[(2e)-3,7-dimethylocta-2,6-dienoxy]-4,5-dimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC\C=C(/C)CCC=C(C)C)=C1OC YPBSBPWIYVSLNE-NTEUORMPSA-N 0.000 description 3
- PQARYKOQEWINDJ-GXDHUFHOSA-N 3-[(2e)-3,7-dimethylocta-2,6-dienoxy]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC\C=C(/C)CCC=C(C)C PQARYKOQEWINDJ-GXDHUFHOSA-N 0.000 description 3
- VUOIWJZHWKSCSX-NTEUORMPSA-N 4-[(2e)-3,7-dimethylocta-2,6-dienoxy]-3,5-dimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC\C=C(/C)CCC=C(C)C VUOIWJZHWKSCSX-NTEUORMPSA-N 0.000 description 3
- WDTAZUUNSIGDLP-GXDHUFHOSA-N 4-[(2e)-3,7-dimethylocta-2,6-dienoxy]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1OC\C=C(/C)CCC=C(C)C WDTAZUUNSIGDLP-GXDHUFHOSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12219596 | 1996-04-18 | ||
| JP8-122195 | 1996-09-30 | ||
| JP27887196 | 1996-09-30 | ||
| JP8-278871 | 1996-09-30 | ||
| JP01205697A JP4150435B2 (ja) | 1996-04-18 | 1997-01-06 | アルキレンジアミン誘導体及び抗潰瘍剤、抗菌剤 |
| JP9-12056 | 1997-01-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR19980069747A true KR19980069747A (ko) | 1998-10-26 |
Family
ID=27279684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019970015041A Withdrawn KR19980069747A (ko) | 1996-04-18 | 1997-04-18 | 알킬렌디아민 유도체 및 항궤양제, 항균제 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5814634A (enExample) |
| EP (1) | EP0802196B1 (enExample) |
| JP (1) | JP4150435B2 (enExample) |
| KR (1) | KR19980069747A (enExample) |
| AT (1) | ATE204867T1 (enExample) |
| CA (1) | CA2202958A1 (enExample) |
| DE (1) | DE69706355T2 (enExample) |
| TW (1) | TW399044B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1131290B1 (en) * | 1998-11-20 | 2008-02-20 | F. Hoffmann-La Roche Ag | Piperidine ccr-3 receptor antagonists |
| CA2371728C (en) * | 1999-06-11 | 2009-06-02 | Neorx Corporation | High dose radionuclide complexes for bone marrow suppression |
| US7094885B2 (en) * | 1999-07-11 | 2006-08-22 | Neorx Corporation | Skeletal-targeted radiation to treat bone-associated pathologies |
| WO2002062398A2 (en) | 2001-01-08 | 2002-08-15 | Neorx Corporation | Radioactively labelled conjugates of phosphonates |
| WO2003051403A1 (en) | 2001-12-13 | 2003-06-26 | Dow Global Technologies Inc. | Treatment of osteomyelitis with radiopharmaceuticals |
| CN103012318B (zh) * | 2012-11-25 | 2014-12-10 | 大理学院 | 氟苄基取代哌嗪类化合物及其制备和医药用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01168678A (ja) * | 1987-12-24 | 1989-07-04 | Teikoku Chem Ind Corp Ltd | ベンズアミド誘導体 |
| JP2700910B2 (ja) * | 1989-02-07 | 1998-01-21 | 帝国化学産業株式会社 | ベンズアミド誘導体 |
| JP2843871B2 (ja) * | 1990-05-14 | 1999-01-06 | 本田技研工業株式会社 | 内燃エンジンの燃焼異常検出装置 |
| JPH05239005A (ja) * | 1992-02-28 | 1993-09-17 | Kitsuen Kagaku Kenkyu Zaidan | Ｎ−（２−アミノエチル）ベンズアミド類およびその新規中間体 |
| IT1266582B1 (it) * | 1993-07-30 | 1997-01-09 | Recordati Chem Pharm | Derivati (di)azacicloesanici e diazacicloeptanici |
-
1997
- 1997-01-06 JP JP01205697A patent/JP4150435B2/ja not_active Expired - Fee Related
- 1997-04-15 TW TW086104833A patent/TW399044B/zh not_active IP Right Cessation
- 1997-04-17 US US08/842,891 patent/US5814634A/en not_active Expired - Lifetime
- 1997-04-17 CA CA002202958A patent/CA2202958A1/en not_active Abandoned
- 1997-04-18 AT AT97302666T patent/ATE204867T1/de not_active IP Right Cessation
- 1997-04-18 EP EP97302666A patent/EP0802196B1/en not_active Expired - Lifetime
- 1997-04-18 DE DE69706355T patent/DE69706355T2/de not_active Expired - Lifetime
- 1997-04-18 KR KR1019970015041A patent/KR19980069747A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU1898797A (en) | 1997-10-23 |
| TW399044B (en) | 2000-07-21 |
| DE69706355D1 (de) | 2001-10-04 |
| US5814634A (en) | 1998-09-29 |
| JP4150435B2 (ja) | 2008-09-17 |
| ATE204867T1 (de) | 2001-09-15 |
| CA2202958A1 (en) | 1997-10-18 |
| EP0802196A1 (en) | 1997-10-22 |
| AU711954B2 (en) | 1999-10-28 |
| EP0802196B1 (en) | 2001-08-29 |
| DE69706355T2 (de) | 2002-06-13 |
| JPH10152471A (ja) | 1998-06-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19970418 |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |