KR20150024329A - 아미도페녹시프로판올아민 - Google Patents
아미도페녹시프로판올아민 Download PDFInfo
- Publication number
- KR20150024329A KR20150024329A KR1020147034458A KR20147034458A KR20150024329A KR 20150024329 A KR20150024329 A KR 20150024329A KR 1020147034458 A KR1020147034458 A KR 1020147034458A KR 20147034458 A KR20147034458 A KR 20147034458A KR 20150024329 A KR20150024329 A KR 20150024329A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- benzamide
- hydroxy
- phenyl
- propoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims abstract description 282
- -1 arylamino alcohol Chemical compound 0.000 claims abstract description 193
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 208000035475 disorder Diseases 0.000 claims abstract description 19
- 230000001404 mediated effect Effects 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 229940079593 drug Drugs 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- SZDCASJNCGOZOC-UHFFFAOYSA-N 2-(2-fluorophenyl)benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1F SZDCASJNCGOZOC-UHFFFAOYSA-N 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 8
- 229960000581 salicylamide Drugs 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- RUBUMKVKAWCNHS-UHFFFAOYSA-N 2-[3-[2-adamantyl(methyl)amino]-2-hydroxypropoxy]benzoic acid Chemical compound C1C2CC(C3)CC1CC3C2N(C)CC(O)COC1=CC=CC=C1C(O)=O RUBUMKVKAWCNHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
- YGEZVRQMLKFAMT-UHFFFAOYSA-N 2-[3-(butylamino)-2-hydroxypropoxy]-n-(3-methylbutyl)benzamide Chemical compound CCCCNCC(O)COC1=CC=CC=C1C(=O)NCCC(C)C YGEZVRQMLKFAMT-UHFFFAOYSA-N 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 5
- DFRFSOBMMJUOFL-UHFFFAOYSA-N 2-[3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropoxy]-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CC(O)COC1=CC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 DFRFSOBMMJUOFL-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- YKQKLKSMFKHTEF-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)-n-(3-phenylpropyl)benzamide Chemical compound C=1C=CC=C(OCC2OC2)C=1C(=O)NCCCC1=CC=CC=C1 YKQKLKSMFKHTEF-UHFFFAOYSA-N 0.000 claims description 3
- CMFLNDSRSHWZMJ-UHFFFAOYSA-N 2-[3-(1-adamantylamino)-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C(C2)CC(C3)CC2CC13NCC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 CMFLNDSRSHWZMJ-UHFFFAOYSA-N 0.000 claims description 3
- RJYNIIGRRKPNFM-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C(C2)CC(C3)CC2CC13CNCC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 RJYNIIGRRKPNFM-UHFFFAOYSA-N 0.000 claims description 3
- OXERWTWOCOKMOK-UHFFFAOYSA-N 2-[3-(2-adamantylamino)-2-hydroxypropoxy]-n-[(2-methoxyphenyl)methyl]benzamide Chemical compound COC1=CC=CC=C1CNC(=O)C1=CC=CC=C1OCC(O)CNC1C(C2)CC3CC2CC1C3 OXERWTWOCOKMOK-UHFFFAOYSA-N 0.000 claims description 3
- TZGATEMHIPZDLE-UHFFFAOYSA-N 2-[3-(2-adamantylamino)-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C2CC(C3)CC1CC3C2NCC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 TZGATEMHIPZDLE-UHFFFAOYSA-N 0.000 claims description 3
- QDAVBKJOGAOQJQ-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC(C(F)(F)F)=C1 QDAVBKJOGAOQJQ-UHFFFAOYSA-N 0.000 claims description 3
- DBPKQWDFDUEKOU-UHFFFAOYSA-N 2-[3-[(4-benzoylphenyl)methylamino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C=1C=CC=C(C(=O)NCC=2C=CC=CC=2)C=1OCC(O)CNCC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 DBPKQWDFDUEKOU-UHFFFAOYSA-N 0.000 claims description 3
- DXNUBTQDYLRPIT-UHFFFAOYSA-N 2-[3-[1-adamantylmethyl(methyl)amino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C(C2)CC(C3)CC2CC13CN(C)CC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 DXNUBTQDYLRPIT-UHFFFAOYSA-N 0.000 claims description 3
- VOHBDHMMUAANQD-UHFFFAOYSA-N 2-[3-[2-adamantyl(cyclopropyl)amino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1CC1N(C1C2CC3CC(C2)CC1C3)CC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 VOHBDHMMUAANQD-UHFFFAOYSA-N 0.000 claims description 3
- WECAVAZEBMEBLV-UHFFFAOYSA-N 2-[3-[2-adamantyl(methyl)amino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C2CC(C3)CC1CC3C2N(C)CC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 WECAVAZEBMEBLV-UHFFFAOYSA-N 0.000 claims description 3
- COKSCZFBMIUKFK-UHFFFAOYSA-N 2-[3-[2-adamantyl(pentyl)amino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C2CC(C3)CC1CC3C2N(CCCCC)CC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 COKSCZFBMIUKFK-UHFFFAOYSA-N 0.000 claims description 3
- CZYUTFDAEHEKGZ-UHFFFAOYSA-N 2-[3-[2-adamantyl-[(2-methoxyphenyl)methyl]amino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound COC1=CC=CC=C1CN(C1C2CC3CC(C2)CC1C3)CC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 CZYUTFDAEHEKGZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- XBGXGCOLWCMVOI-UHFFFAOYSA-N 3-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(F)(F)F)=C1 XBGXGCOLWCMVOI-UHFFFAOYSA-N 0.000 claims description 3
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 3
- 150000008366 benzophenones Chemical class 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- KIPNXZZNYXFXBI-UHFFFAOYSA-N 2-[3-(1-adamantylamino)-2-hydroxypropoxy]-5-bromo-n-(4-fluorophenyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13NCC(O)COC1=CC=C(Br)C=C1C(=O)NC1=CC=C(F)C=C1 KIPNXZZNYXFXBI-UHFFFAOYSA-N 0.000 claims description 2
- DGFGZSGPLBZYGH-UHFFFAOYSA-N 2-[3-(2-adamantylamino)-2-hydroxypropoxy]-5-chloro-n-(2-phenylethyl)benzamide Chemical compound C1C2CC(C3)CC1CC3C2NCC(O)COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=CC=C1 DGFGZSGPLBZYGH-UHFFFAOYSA-N 0.000 claims description 2
- IOARWPNCVFDCKG-UHFFFAOYSA-N 2-[3-[2-(1-adamantyl)ethylamino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C(C2)CC(C3)CC2CC13CCNCC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 IOARWPNCVFDCKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 abstract description 26
- 229940088679 drug related substance Drugs 0.000 abstract description 26
- 239000003430 antimalarial agent Substances 0.000 abstract description 17
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000000069 prophylactic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 38
- 239000000203 mixture Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000001412 amines Chemical group 0.000 description 20
- 201000004792 malaria Diseases 0.000 description 16
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 14
- 241000223960 Plasmodium falciparum Species 0.000 description 14
- 229960003677 chloroquine Drugs 0.000 description 14
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 230000000078 anti-malarial effect Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000012512 characterization method Methods 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- 238000002965 ELISA Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical class NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 7
- BLUAFEHZUWYNDE-NNWCWBAJSA-N artemisinin Chemical compound C([C@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2OC(=O)[C@@H]4C BLUAFEHZUWYNDE-NNWCWBAJSA-N 0.000 description 7
- 125000001153 fluoro group Chemical group F* 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 238000007142 ring opening reaction Methods 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 6
- CDNNMNLILHWPMH-UHFFFAOYSA-N methyl 2-(oxiran-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1OC1 CDNNMNLILHWPMH-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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- 208000030852 Parasitic disease Diseases 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
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- 125000001246 bromo group Chemical group Br* 0.000 description 5
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- SXYIRMFQILZOAM-HVNFFKDJSA-N dihydroartemisinin methyl ether Chemical compound C1C[C@H]2[C@H](C)CC[C@H]3[C@@H](C)[C@@H](OC)O[C@H]4[C@]32OO[C@@]1(C)O4 SXYIRMFQILZOAM-HVNFFKDJSA-N 0.000 description 5
- 210000003743 erythrocyte Anatomy 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 5
- GEJKXDWUXSMTSF-UHFFFAOYSA-N 2-[2-hydroxy-3-(propylamino)propoxy]-n-(4-methylphenyl)benzamide Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)NC1=CC=C(C)C=C1 GEJKXDWUXSMTSF-UHFFFAOYSA-N 0.000 description 4
- ABGXADJDTPFFSZ-UHFFFAOYSA-N 4-benzylpiperidine Chemical compound C=1C=CC=CC=1CC1CCNCC1 ABGXADJDTPFFSZ-UHFFFAOYSA-N 0.000 description 4
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- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 4
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- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 4
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- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- MDAMPKZYAWPFJY-UHFFFAOYSA-N 2-[3-(dibutylamino)-2-hydroxypropoxy]-n-(4-fluorophenyl)benzamide Chemical compound CCCCN(CCCC)CC(O)COC1=CC=CC=C1C(=O)NC1=CC=C(F)C=C1 MDAMPKZYAWPFJY-UHFFFAOYSA-N 0.000 description 3
- UXYMTVZHGSBSCD-UHFFFAOYSA-N 2-hydroxy-n-(3-methylbutyl)-5-prop-2-ynoxybenzamide Chemical compound CC(C)CCNC(=O)C1=CC(OCC#C)=CC=C1O UXYMTVZHGSBSCD-UHFFFAOYSA-N 0.000 description 3
- QMLRNTPTRWMCOP-UHFFFAOYSA-N 2-hydroxy-n-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=CC=C1O QMLRNTPTRWMCOP-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001345 alkine derivatives Chemical group 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 230000003288 anthiarrhythmic effect Effects 0.000 description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
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- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/64—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
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- C07C235/66—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and singly-bound oxygen atoms, bound to the same carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
- C07D229/02—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms containing three-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
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- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Tropical Medicine & Parasitology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12171729 | 2012-06-13 | ||
| EP12171729.2 | 2012-06-13 | ||
| PCT/EP2013/061880 WO2013186153A2 (en) | 2012-06-13 | 2013-06-10 | Amidophenoxypropanolamines |
Publications (1)
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|---|---|
| KR20150024329A true KR20150024329A (ko) | 2015-03-06 |
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| KR1020147034458A Withdrawn KR20150024329A (ko) | 2012-06-13 | 2013-06-10 | 아미도페녹시프로판올아민 |
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| JP (1) | JP2015525224A (enExample) |
| KR (1) | KR20150024329A (enExample) |
| CN (1) | CN104364234A (enExample) |
| AU (1) | AU2013276702A1 (enExample) |
| BR (1) | BR112014030631A2 (enExample) |
| CA (1) | CA2874295A1 (enExample) |
| EA (1) | EA201492291A1 (enExample) |
| IN (1) | IN2014MN02365A (enExample) |
| MX (1) | MX2014014713A (enExample) |
| PH (1) | PH12014502774A1 (enExample) |
| SG (1) | SG11201407434XA (enExample) |
| WO (1) | WO2013186153A2 (enExample) |
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| CN111187212B (zh) * | 2020-01-09 | 2021-04-20 | 西安交通大学 | 一种免洗型光亲和链接体及制备方法和应用 |
| CN119822990B (zh) * | 2025-01-09 | 2025-11-04 | 贵州大学 | 一类金刚烷异丙醇胺结构的化合物及其制备方法和用途 |
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| IL40343A0 (en) * | 1971-11-08 | 1972-11-28 | Miles Lab | Novel derivatives of salicylamide |
| EP0691962B1 (en) * | 1993-03-29 | 2000-09-13 | Basf Aktiengesellschaft | 1-amino-3-phenoxy propane derivatives as modulators of multi-drug resistance |
| SE0302755D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel compounds |
| US8067620B2 (en) * | 2005-05-04 | 2011-11-29 | Medicines For Malaria Venture Mmv | Dispiro 1,2,4-trioxolane antimalarials |
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2013
- 2013-06-10 IN IN2365MUN2014 patent/IN2014MN02365A/en unknown
- 2013-06-10 CN CN201380031667.1A patent/CN104364234A/zh active Pending
- 2013-06-10 EA EA201492291A patent/EA201492291A1/ru unknown
- 2013-06-10 KR KR1020147034458A patent/KR20150024329A/ko not_active Withdrawn
- 2013-06-10 US US14/403,916 patent/US20150141437A1/en not_active Abandoned
- 2013-06-10 EP EP13731047.0A patent/EP2861561A2/en not_active Withdrawn
- 2013-06-10 CA CA2874295A patent/CA2874295A1/en not_active Abandoned
- 2013-06-10 AU AU2013276702A patent/AU2013276702A1/en not_active Abandoned
- 2013-06-10 MX MX2014014713A patent/MX2014014713A/es unknown
- 2013-06-10 SG SG11201407434XA patent/SG11201407434XA/en unknown
- 2013-06-10 WO PCT/EP2013/061880 patent/WO2013186153A2/en not_active Ceased
- 2013-06-10 BR BR112014030631A patent/BR112014030631A2/pt not_active IP Right Cessation
- 2013-06-10 JP JP2015516573A patent/JP2015525224A/ja active Pending
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2014
- 2014-12-10 PH PH12014502774A patent/PH12014502774A1/en unknown
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2016
- 2016-07-07 US US15/204,585 patent/US20160318887A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EA201492291A1 (ru) | 2015-05-29 |
| MX2014014713A (es) | 2015-08-05 |
| CA2874295A1 (en) | 2013-12-19 |
| EP2861561A2 (en) | 2015-04-22 |
| WO2013186153A3 (en) | 2014-02-27 |
| PH12014502774A1 (en) | 2015-02-02 |
| US20150141437A1 (en) | 2015-05-21 |
| WO2013186153A2 (en) | 2013-12-19 |
| IN2014MN02365A (enExample) | 2015-08-14 |
| SG11201407434XA (en) | 2014-12-30 |
| JP2015525224A (ja) | 2015-09-03 |
| CN104364234A (zh) | 2015-02-18 |
| US20160318887A1 (en) | 2016-11-03 |
| AU2013276702A1 (en) | 2014-11-27 |
| BR112014030631A2 (pt) | 2017-06-27 |
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