CA2874295A1 - Amidophenoxypropanolamines - Google Patents
Amidophenoxypropanolamines Download PDFInfo
- Publication number
- CA2874295A1 CA2874295A1 CA2874295A CA2874295A CA2874295A1 CA 2874295 A1 CA2874295 A1 CA 2874295A1 CA 2874295 A CA2874295 A CA 2874295A CA 2874295 A CA2874295 A CA 2874295A CA 2874295 A1 CA2874295 A1 CA 2874295A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- benzamide
- hydroxy
- propoxy
- phenyl
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
- -1 arylamino alcohol Chemical compound 0.000 claims abstract description 107
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 31
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 22
- 230000001404 mediated effect Effects 0.000 claims abstract description 20
- 208000035475 disorder Diseases 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 239000007856 photoaffinity label Substances 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 34
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 229940079593 drug Drugs 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000004193 piperazinyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 125000004209 (C1-C8) 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
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 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 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
- 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 5
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 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 4
- YXYVAJUXVFEZAM-UHFFFAOYSA-N 2-[3-[2-adamantyl(2-phenylethyl)amino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C=1C=CC=CC=1CCN(C1C2CC3CC(C2)CC1C3)CC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 YXYVAJUXVFEZAM-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229960000581 salicylamide Drugs 0.000 claims description 4
- YFNCUBLSBJBLCB-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)-n-(2-phenylethyl)benzamide Chemical compound C=1C=CC=C(OCC2OC2)C=1C(=O)NCCC1=CC=CC=C1 YFNCUBLSBJBLCB-UHFFFAOYSA-N 0.000 claims description 3
- 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
- DMIJGKBWSDFRIG-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-5-chloro-n-(2-phenylethyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13CNCC(O)COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=CC=C1 DMIJGKBWSDFRIG-UHFFFAOYSA-N 0.000 claims description 3
- QVWWEUHQYKYRPK-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-(2,4-difluorophenyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13CNCC(O)COC1=CC=CC=C1C(=O)NC1=CC=C(F)C=C1F QVWWEUHQYKYRPK-UHFFFAOYSA-N 0.000 claims description 3
- CMJRWZZVSYGIJA-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=CC=C1OCC(O)CNCC1(C2)CC(C3)CC2CC3C1 CMJRWZZVSYGIJA-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
- 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
- ZKUTVCLAWWFFPM-UHFFFAOYSA-N 2-[3-[1-(1-adamantyl)ethylamino]-2-hydroxypropoxy]-n-(4-methylphenyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13C(C)NCC(O)COC1=CC=CC=C1C(=O)NC1=CC=C(C)C=C1 ZKUTVCLAWWFFPM-UHFFFAOYSA-N 0.000 claims description 3
- BWXQEMXIIDYXQT-UHFFFAOYSA-N 2-[3-[1-(1-adamantyl)ethylamino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C(C2)CC(C3)CC2CC13C(C)NCC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 BWXQEMXIIDYXQT-UHFFFAOYSA-N 0.000 claims description 3
- JEKGAMODUQFKTI-UHFFFAOYSA-N 2-[3-[1-adamantylmethyl(methyl)amino]-2-hydroxypropoxy]-n-(4-fluorophenyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13CN(C)CC(O)COC1=CC=CC=C1C(=O)NC1=CC=C(F)C=C1 JEKGAMODUQFKTI-UHFFFAOYSA-N 0.000 claims description 3
- SNFKBDLOOQGERI-UHFFFAOYSA-N 2-[3-[2-adamantyl(propyl)amino]-2-hydroxypropoxy]-n-benzylbenzamide Chemical compound C1C2CC(C3)CC1CC3C2N(CCC)CC(O)COC1=CC=CC=C1C(=O)NCC1=CC=CC=C1 SNFKBDLOOQGERI-UHFFFAOYSA-N 0.000 claims description 3
- KYOZUXWPSBBRJJ-UHFFFAOYSA-N 5-chloro-2-(oxiran-2-ylmethoxy)-n-(2-phenylethyl)benzamide Chemical compound C=1C=CC=CC=1CCNC(=O)C1=CC(Cl)=CC=C1OCC1CO1 KYOZUXWPSBBRJJ-UHFFFAOYSA-N 0.000 claims description 3
- QTOZDGRIULTXGV-UHFFFAOYSA-N 5-chloro-2-hydroxy-n-(naphthalen-1-ylmethyl)benzamide Chemical compound OC1=CC=C(Cl)C=C1C(=O)NCC1=CC=CC2=CC=CC=C12 QTOZDGRIULTXGV-UHFFFAOYSA-N 0.000 claims description 3
- SRNULMVZIBHMHG-UHFFFAOYSA-N 5-chloro-n-(4-fluorophenyl)-2-(oxiran-2-ylmethoxy)benzamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC(Cl)=CC=C1OCC1OC1 SRNULMVZIBHMHG-UHFFFAOYSA-N 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 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
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- WYKMNAOWSVPHAE-UHFFFAOYSA-N n-(2,4-difluorophenyl)-2-(oxiran-2-ylmethoxy)benzamide Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CC=C1OCC1OC1 WYKMNAOWSVPHAE-UHFFFAOYSA-N 0.000 claims description 3
- OXQBIJKCHLFSKT-UHFFFAOYSA-N n-(3-methylbutyl)-2-(oxiran-2-ylmethoxy)benzamide Chemical compound CC(C)CCNC(=O)C1=CC=CC=C1OCC1OC1 OXQBIJKCHLFSKT-UHFFFAOYSA-N 0.000 claims description 3
- LWHTYWYRXYJWEF-UHFFFAOYSA-N n-(4-fluorophenyl)-2-hydroxy-5-prop-2-ynoxybenzamide Chemical compound OC1=CC=C(OCC#C)C=C1C(=O)NC1=CC=C(F)C=C1 LWHTYWYRXYJWEF-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- SEVVPWOEIHLQGH-UWTATZPHSA-N (2r)-2-amino-3-(4-oxo-1,2,5-thiadiazol-3-yl)propanoic acid Chemical compound OC(=O)[C@H](N)CC1=NSN=C1O SEVVPWOEIHLQGH-UWTATZPHSA-N 0.000 claims description 2
- QPUKJLBQNYLSIJ-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-(3-methylbutyl)benzamide Chemical compound CC(C)CCNC(=O)C1=CC=CC=C1OCC(O)CNCC1(C2)CC(C3)CC2CC3C1 QPUKJLBQNYLSIJ-UHFFFAOYSA-N 0.000 claims description 2
- KPAGRBJFDOICHA-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-(4-bromophenyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13CNCC(O)COC1=CC=CC=C1C(=O)NC1=CC=C(Br)C=C1 KPAGRBJFDOICHA-UHFFFAOYSA-N 0.000 claims description 2
- ZNNIRCDXWALTOU-UHFFFAOYSA-N 2-[3-[1-(1-adamantyl)ethylamino]-2-hydroxypropoxy]-5-chloro-N-(naphthalen-1-ylmethyl)benzamide Chemical compound CC(NCC(O)COc1ccc(Cl)cc1C(=O)NCc1cccc2ccccc12)C12CC3CC(CC(C3)C1)C2 ZNNIRCDXWALTOU-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
- HOBPGWGPQYMLJK-UHFFFAOYSA-N n-(2-fluorophenyl)-2-(oxiran-2-ylmethoxy)benzamide Chemical compound FC1=CC=CC=C1NC(=O)C1=CC=CC=C1OCC1OC1 HOBPGWGPQYMLJK-UHFFFAOYSA-N 0.000 claims description 2
- TUZBSOYMLHRWDG-UHFFFAOYSA-N n-(4-fluorophenyl)-2-(oxiran-2-ylmethoxy)-5-prop-2-ynoxybenzamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC(OCC#C)=CC=C1OCC1OC1 TUZBSOYMLHRWDG-UHFFFAOYSA-N 0.000 claims description 2
- NUHXHWGEJVEVQM-UHFFFAOYSA-N n-(4-fluorophenyl)-2-(oxiran-2-ylmethoxy)benzamide Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC=C1OCC1OC1 NUHXHWGEJVEVQM-UHFFFAOYSA-N 0.000 claims description 2
- VIXSJPNJWYSJAC-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-2-(oxiran-2-ylmethoxy)benzamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)C1=CC=CC=C1OCC1OC1 VIXSJPNJWYSJAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- SDDOWQFJUIAPBO-UHFFFAOYSA-N 2-[2-hydroxy-3-[(3-hydroxy-1-adamantyl)amino]propoxy]-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1C(C2)CC(C3)CC2(O)CC13NCC(O)COC1=CC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 SDDOWQFJUIAPBO-UHFFFAOYSA-N 0.000 claims 2
- JCKSUEMHTRAARH-UHFFFAOYSA-N 2-[2-hydroxy-3-[[4-(trifluoromethyl)phenyl]methylamino]propoxy]-n-(3-methylbutyl)benzamide Chemical compound CC(C)CCNC(=O)C1=CC=CC=C1OCC(O)CNCC1=CC=C(C(F)(F)F)C=C1 JCKSUEMHTRAARH-UHFFFAOYSA-N 0.000 claims 2
- HPLCYHFSKKVYGV-UHFFFAOYSA-N 2-[3-(1-adamantylamino)-2-hydroxypropoxy]-n-[(2-methoxyphenyl)methyl]benzamide Chemical compound COC1=CC=CC=C1CNC(=O)C1=CC=CC=C1OCC(O)CNC1(C2)CC(C3)CC2CC3C1 HPLCYHFSKKVYGV-UHFFFAOYSA-N 0.000 claims 2
- UKNZUMYAHQIQDO-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-5-chloro-n-(naphthalen-1-ylmethyl)benzamide Chemical compound C1=CC=C2C(CNC(=O)C3=CC(Cl)=CC=C3OCC(CNCC34CC5CC(CC(C5)C3)C4)O)=CC=CC2=C1 UKNZUMYAHQIQDO-UHFFFAOYSA-N 0.000 claims 2
- LKRUOISHXWADEN-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-(2-phenylethyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13CNCC(O)COC1=CC=CC=C1C(=O)NCCC1=CC=CC=C1 LKRUOISHXWADEN-UHFFFAOYSA-N 0.000 claims 2
- SQPUYNAFJQIFSR-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-(3-methylbutyl)-5-prop-2-ynoxybenzamide Chemical compound CC(C)CCNC(=O)C1=CC(OCC#C)=CC=C1OCC(O)CNCC1(C2)CC(C3)CC2CC3C1 SQPUYNAFJQIFSR-UHFFFAOYSA-N 0.000 claims 2
- CBTSUUTYSYYVQC-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-(3-phenylpropyl)benzamide Chemical compound C1C(C2)CC(C3)CC2CC13CNCC(O)COC1=CC=CC=C1C(=O)NCCCC1=CC=CC=C1 CBTSUUTYSYYVQC-UHFFFAOYSA-N 0.000 claims 2
- BAMQFYWPFGQPLC-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-[(2-methoxyphenyl)methyl]benzamide Chemical compound COC1=CC=CC=C1CNC(=O)C1=CC=CC=C1OCC(O)CNCC1(C2)CC(C3)CC2CC3C1 BAMQFYWPFGQPLC-UHFFFAOYSA-N 0.000 claims 2
- LGKMHVNAZPXMJD-UHFFFAOYSA-N 2-[3-(1-adamantylmethylamino)-2-hydroxypropoxy]-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1C(C2)CC(C3)CC2CC13CNCC(O)COC1=CC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 LGKMHVNAZPXMJD-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- ZTXKWAGQKGSPKL-UHFFFAOYSA-N 2-[3-(2-adamantylamino)-2-hydroxypropoxy]-n-(2-phenylethyl)benzamide Chemical compound C1C2CC(C3)CC1CC3C2NCC(O)COC1=CC=CC=C1C(=O)NCCC1=CC=CC=C1 ZTXKWAGQKGSPKL-UHFFFAOYSA-N 0.000 claims 2
- GBPYQWRSXLDKLA-UHFFFAOYSA-N 2-[3-(2-adamantylamino)-2-hydroxypropoxy]-n-(3-phenylpropyl)benzamide Chemical compound C1C2CC(C3)CC1CC3C2NCC(O)COC1=CC=CC=C1C(=O)NCCCC1=CC=CC=C1 GBPYQWRSXLDKLA-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- DXUFRSXLWMCEEB-UHFFFAOYSA-N 2-[3-(2-adamantylamino)-2-hydroxypropoxy]-n-propylbenzamide Chemical compound CCCNC(=O)C1=CC=CC=C1OCC(O)CNC1C(C2)CC3CC2CC1C3 DXUFRSXLWMCEEB-UHFFFAOYSA-N 0.000 claims 2
- JOPUZOGJJACPPK-UHFFFAOYSA-N 2-[3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropoxy]-5-chloro-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CC(O)COC1=CC=C(Cl)C=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 JOPUZOGJJACPPK-UHFFFAOYSA-N 0.000 claims 2
- ZPTINVLTBADDMU-UHFFFAOYSA-N 2-[3-(4-benzhydrylpiperazin-1-yl)-2-hydroxypropoxy]-n-(4-methylphenyl)benzamide Chemical compound C1=CC(C)=CC=C1NC(=O)C1=CC=CC=C1OCC(O)CN1CCN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 ZPTINVLTBADDMU-UHFFFAOYSA-N 0.000 claims 2
- UNJMNVIGOPYEDS-UHFFFAOYSA-N 2-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-5-bromo-n-(4-fluorophenyl)benzamide Chemical compound C1CC(CC=2C=CC=CC=2)CCN1CC(O)COC1=CC=C(Br)C=C1C(=O)NC1=CC=C(F)C=C1 UNJMNVIGOPYEDS-UHFFFAOYSA-N 0.000 claims 2
- GPHTZAMSUKXKBU-UHFFFAOYSA-N 2-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-5-chloro-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1CC(CC=2C=CC=CC=2)CCN1CC(O)COC1=CC=C(Cl)C=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 GPHTZAMSUKXKBU-UHFFFAOYSA-N 0.000 claims 2
- XYTYYJDTUVHEBW-UHFFFAOYSA-N 2-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-n-(4-fluorophenyl)benzamide Chemical compound C1CC(CC=2C=CC=CC=2)CCN1CC(O)COC1=CC=CC=C1C(=O)NC1=CC=C(F)C=C1 XYTYYJDTUVHEBW-UHFFFAOYSA-N 0.000 claims 2
- FJKSKUZXIXKKNN-UHFFFAOYSA-N 2-[3-(4-benzylpiperidin-1-yl)-2-hydroxypropoxy]-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound C1CC(CC=2C=CC=CC=2)CCN1CC(O)COC1=CC=CC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FJKSKUZXIXKKNN-UHFFFAOYSA-N 0.000 claims 2
- PFLCGHUEKVNDKP-UHFFFAOYSA-N 2-[3-(benzylamino)-2-hydroxypropoxy]-n-(3-methylbutyl)benzamide Chemical compound CC(C)CCNC(=O)C1=CC=CC=C1OCC(O)CNCC1=CC=CC=C1 PFLCGHUEKVNDKP-UHFFFAOYSA-N 0.000 claims 2
- VYZKNNVUCSCHLQ-UHFFFAOYSA-N 2-[3-(dibutylamino)-2-hydroxypropoxy]-n-(3-methylbutyl)benzamide Chemical compound CCCCN(CCCC)CC(O)COC1=CC=CC=C1C(=O)NCCC(C)C VYZKNNVUCSCHLQ-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
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- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 1
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WOOWBQQQJXZGIE-UHFFFAOYSA-N n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C WOOWBQQQJXZGIE-UHFFFAOYSA-N 0.000 description 1
- VSKMVAJFNWCWPG-UHFFFAOYSA-N n-methyladamantan-2-amine Chemical compound C1C(C2)CC3CC1C(NC)C2C3 VSKMVAJFNWCWPG-UHFFFAOYSA-N 0.000 description 1
- XKGPNSLQHYESJB-UHFFFAOYSA-N n-naphthalen-2-yl-2-propoxybenzamide Chemical compound CCCOC1=CC=CC=C1C(=O)NC1=CC=C(C=CC=C2)C2=C1 XKGPNSLQHYESJB-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 1
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- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
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- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000008261 resistance mechanism Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
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- 239000007962 solid dispersion Substances 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- 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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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/396—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having three-membered rings, e.g. aziridine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/04—Amoebicides
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
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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
-
- 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
- C07C235/60—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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- 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
-
- 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
- C07C235/66—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
-
- 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
- C07D295/08—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- 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)
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| EP12171729 | 2012-06-13 | ||
| EP12171729.2 | 2012-06-13 | ||
| PCT/EP2013/061880 WO2013186153A2 (en) | 2012-06-13 | 2013-06-10 | Amidophenoxypropanolamines |
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| CA2874295A1 true CA2874295A1 (en) | 2013-12-19 |
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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 |
-
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
-
2014
- 2014-12-10 PH PH12014502774A patent/PH12014502774A1/en unknown
-
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 |
| EP2861561A2 (en) | 2015-04-22 |
| WO2013186153A3 (en) | 2014-02-27 |
| PH12014502774A1 (en) | 2015-02-02 |
| US20150141437A1 (en) | 2015-05-21 |
| KR20150024329A (ko) | 2015-03-06 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20180612 |