RU2447060C2 - Ингибиторы сфингозинкиназы - Google Patents
Ингибиторы сфингозинкиназы Download PDFInfo
- Publication number
- RU2447060C2 RU2447060C2 RU2008100606/04A RU2008100606A RU2447060C2 RU 2447060 C2 RU2447060 C2 RU 2447060C2 RU 2008100606/04 A RU2008100606/04 A RU 2008100606/04A RU 2008100606 A RU2008100606 A RU 2008100606A RU 2447060 C2 RU2447060 C2 RU 2447060C2
- Authority
- RU
- Russia
- Prior art keywords
- chlorophenyl
- carboxylic acid
- adamantane
- ethyl
- adamantan
- Prior art date
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- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- ZDRVLAOYDGQLFI-UHFFFAOYSA-N 4-[[4-(4-chlorophenyl)-1,3-thiazol-2-yl]amino]phenol;hydrochloride Chemical compound Cl.C1=CC(O)=CC=C1NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 ZDRVLAOYDGQLFI-UHFFFAOYSA-N 0.000 claims abstract 4
- 108010035597 sphingosine kinase Proteins 0.000 claims abstract 4
- 102000001253 Protein Kinase Human genes 0.000 claims abstract 3
- 206010006187 Breast cancer Diseases 0.000 claims abstract 2
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims abstract 2
- 206010003246 arthritis Diseases 0.000 claims abstract 2
- 206010009887 colitis Diseases 0.000 claims abstract 2
- 201000010099 disease Diseases 0.000 claims abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 2
- 230000002401 inhibitory effect Effects 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- 125000005217 alkenylheteroaryl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 2
- 125000005872 benzooxazolyl group Chemical group 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- ITPHUHRCLPIWNX-UHFFFAOYSA-N 1-(3-phenyl-1-adamantyl)-n-(pyridin-4-ylmethyl)ethanamine Chemical compound C1C(CC(C2)(C3)C=4C=CC=CC=4)CC2CC13C(C)NCC1=CC=NC=C1 ITPHUHRCLPIWNX-UHFFFAOYSA-N 0.000 claims 1
- YTJSYIDTZUEQNC-UHFFFAOYSA-N 1-(4-bromophenyl)-n-[1-[3-(4-chlorophenyl)-1-adamantyl]ethyl]ethanamine Chemical compound C=1C=C(Br)C=CC=1C(C)NC(C)C(C1)(C2)CC(C3)CC1CC32C1=CC=C(Cl)C=C1 YTJSYIDTZUEQNC-UHFFFAOYSA-N 0.000 claims 1
- ULBNIUROMLDOJN-UHFFFAOYSA-N 1-[3-(4-chlorophenyl)-1-adamantyl]-n-(1h-imidazol-5-ylmethyl)ethanamine Chemical compound C1C(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC2CC13C(C)NCC1=CN=CN1 ULBNIUROMLDOJN-UHFFFAOYSA-N 0.000 claims 1
- BOHCPAZXXDWFOJ-UHFFFAOYSA-N 1-[3-(4-chlorophenyl)-1-adamantyl]-n-(2-pyridin-4-ylethyl)ethanamine Chemical compound C1C(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC2CC13C(C)NCCC1=CC=NC=C1 BOHCPAZXXDWFOJ-UHFFFAOYSA-N 0.000 claims 1
- QGWDIVZNAVTCTM-UHFFFAOYSA-N 1-[3-(4-chlorophenyl)-1-adamantyl]-n-[(6-chloropyridin-3-yl)methyl]ethanamine Chemical compound C1C(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC2CC13C(C)NCC1=CC=C(Cl)N=C1 QGWDIVZNAVTCTM-UHFFFAOYSA-N 0.000 claims 1
- UQQYBGHIKSIJHD-UHFFFAOYSA-N 1-[3-(4-chlorophenyl)-1-adamantyl]-n-[(9-ethylcarbazol-3-yl)methyl]ethanamine Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1CNC(C)C(C1)(C2)CC(C3)CC1CC32C1=CC=C(Cl)C=C1 UQQYBGHIKSIJHD-UHFFFAOYSA-N 0.000 claims 1
- MCRBBWPWULILLX-UHFFFAOYSA-N 1-methyl-n-[1-(3-phenyl-1-adamantyl)ethyl]piperidin-4-amine Chemical compound C1C(CC(C2)(C3)C=4C=CC=CC=4)CC2CC13C(C)NC1CCN(C)CC1 MCRBBWPWULILLX-UHFFFAOYSA-N 0.000 claims 1
- CAOTVXGYTWCKQE-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-(pyridin-4-ylmethyl)-1-adamantanecarboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCC=4C=CN=CC=4)CC2CC3C1 CAOTVXGYTWCKQE-UHFFFAOYSA-N 0.000 claims 1
- OTDRGXKKAVUHRC-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(1-methylpiperidin-4-yl)adamantane-1-carboxamide Chemical compound C1CN(C)CCC1NC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 OTDRGXKKAVUHRC-UHFFFAOYSA-N 0.000 claims 1
- FOGUTKLPKIFAAY-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2,4-dihydroxyphenyl)adamantane-1-carboxamide Chemical compound OC1=CC(O)=CC=C1NC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 FOGUTKLPKIFAAY-UHFFFAOYSA-N 0.000 claims 1
- JHSAICDJDUZLLI-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-ethylsulfanylethyl)adamantane-1-carboxamide Chemical compound C1C(C(=O)NCCSCC)(C2)CC(C3)CC1CC32C1=CC=C(Cl)C=C1 JHSAICDJDUZLLI-UHFFFAOYSA-N 0.000 claims 1
- NJBYWMSTGGPHGV-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-methyl-1h-indol-5-yl)adamantane-1-carboxamide Chemical compound C=1C=C2NC(C)=CC2=CC=1NC(=O)C(C1)(C2)CC(C3)CC1CC32C1=CC=C(Cl)C=C1 NJBYWMSTGGPHGV-UHFFFAOYSA-N 0.000 claims 1
- PDHWTCIBPDYFPU-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-morpholin-4-ylethyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCN4CCOCC4)CC2CC3C1 PDHWTCIBPDYFPU-UHFFFAOYSA-N 0.000 claims 1
- IEGQBFMMSKUZFB-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-phenylethyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCC=4C=CC=CC=4)CC2CC3C1 IEGQBFMMSKUZFB-UHFFFAOYSA-N 0.000 claims 1
- TUNOMCQVHVVXBC-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-piperazin-1-ylethyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCN4CCNCC4)CC2CC3C1 TUNOMCQVHVVXBC-UHFFFAOYSA-N 0.000 claims 1
- MCFZBWFOBKXVPI-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2-pyridin-4-ylethyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCC=4C=CN=CC=4)CC2CC3C1 MCFZBWFOBKXVPI-UHFFFAOYSA-N 0.000 claims 1
- JQWJVPZFSPABGC-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(2h-tetrazol-5-yl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NC=4NN=NN=4)CC2CC3C1 JQWJVPZFSPABGC-UHFFFAOYSA-N 0.000 claims 1
- VVEQHTNBYLWPTI-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(3-imidazol-1-ylpropyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCCN4C=NC=C4)CC2CC3C1 VVEQHTNBYLWPTI-UHFFFAOYSA-N 0.000 claims 1
- HFEVWSNMPDVMMR-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(3-phenylpropyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCCC=4C=CC=CC=4)CC2CC3C1 HFEVWSNMPDVMMR-UHFFFAOYSA-N 0.000 claims 1
- WGPFHEAFOUMERK-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(3-pyrrolidin-1-ylpropyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCCN4CCCC4)CC2CC3C1 WGPFHEAFOUMERK-UHFFFAOYSA-N 0.000 claims 1
- FLJWPZLQSHTEQL-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(4-hydroxyphenyl)adamantane-1-carboxamide Chemical compound C1=CC(O)=CC=C1NC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 FLJWPZLQSHTEQL-UHFFFAOYSA-N 0.000 claims 1
- KYDGZXHLXPTZNJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(7h-purin-6-yl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NC=4C=5N=CNC=5N=CN=4)CC2CC3C1 KYDGZXHLXPTZNJ-UHFFFAOYSA-N 0.000 claims 1
- VJXLEFSBPSFEQO-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-(9-ethylcarbazol-3-yl)adamantane-1-carboxamide Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NC(=O)C(C1)(C2)CC(C3)CC1CC32C1=CC=C(Cl)C=C1 VJXLEFSBPSFEQO-UHFFFAOYSA-N 0.000 claims 1
- PEABYJUNQJJDFL-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[(3,4,5-trifluorophenyl)methyl]adamantane-1-carboxamide Chemical compound FC1=C(F)C(F)=CC(CNC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1 PEABYJUNQJJDFL-UHFFFAOYSA-N 0.000 claims 1
- OXSKXGXUEXMSOU-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[(3,4-difluorophenyl)methyl]adamantane-1-carboxamide Chemical compound C1=C(F)C(F)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 OXSKXGXUEXMSOU-UHFFFAOYSA-N 0.000 claims 1
- KNZHUAFGWMRPPB-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[(3,4-dihydroxyphenyl)methyl]adamantane-1-carboxamide Chemical compound C1=C(O)C(O)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 KNZHUAFGWMRPPB-UHFFFAOYSA-N 0.000 claims 1
- KDVLMDUZMLTVCC-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[(3,5-difluorophenyl)methyl]adamantane-1-carboxamide Chemical compound FC1=CC(F)=CC(CNC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1 KDVLMDUZMLTVCC-UHFFFAOYSA-N 0.000 claims 1
- ZNZJYDHKSURBQW-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[(4-methylsulfanylphenyl)methyl]adamantane-1-carboxamide Chemical compound C1=CC(SC)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 ZNZJYDHKSURBQW-UHFFFAOYSA-N 0.000 claims 1
- YSXVOAGBYOVPCE-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[(4-methylsulfonylphenyl)methyl]adamantane-1-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 YSXVOAGBYOVPCE-UHFFFAOYSA-N 0.000 claims 1
- VBPBIIMTWLNHMF-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[1-(4-chlorophenyl)ethyl]adamantane-1-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C(C1)(C2)CC(C3)CC1CC32C1=CC=C(Cl)C=C1 VBPBIIMTWLNHMF-UHFFFAOYSA-N 0.000 claims 1
- MKNDEXRNJHZKAW-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-(1-methylpyrrolidin-2-yl)ethyl]adamantane-1-carboxamide Chemical compound CN1CCCC1CCNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 MKNDEXRNJHZKAW-UHFFFAOYSA-N 0.000 claims 1
- NEOXEHZXYBCPRQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-(3,4-dihydroxyphenyl)ethyl]adamantane-1-carboxamide Chemical compound C1=C(O)C(O)=CC=C1CCNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 NEOXEHZXYBCPRQ-UHFFFAOYSA-N 0.000 claims 1
- DDKQPYDADCHNAC-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-(4-fluorophenyl)ethyl]adamantane-1-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 DDKQPYDADCHNAC-UHFFFAOYSA-N 0.000 claims 1
- JXODZLJNLRSHAQ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-(4-hydroxyphenyl)ethyl]adamantane-1-carboxamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 JXODZLJNLRSHAQ-UHFFFAOYSA-N 0.000 claims 1
- SHODXBSSKIZNGA-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-(4-methoxyphenyl)ethyl]adamantane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CCNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 SHODXBSSKIZNGA-UHFFFAOYSA-N 0.000 claims 1
- CGNFWPOGZWLXGM-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[3-(2-oxopyrrolidin-1-yl)propyl]adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCCCN4C(CCC4)=O)CC2CC3C1 CGNFWPOGZWLXGM-UHFFFAOYSA-N 0.000 claims 1
- SHJWMULANDOPKJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[3-(hydroxymethyl)phenyl]adamantane-1-carboxamide Chemical compound OCC1=CC=CC(NC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1 SHJWMULANDOPKJ-UHFFFAOYSA-N 0.000 claims 1
- DDYNSGDAPDBOET-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(NC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=N1 DDYNSGDAPDBOET-UHFFFAOYSA-N 0.000 claims 1
- ZHVZPYIHRWVGGN-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[4-(cyanomethyl)phenyl]adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NC=4C=CC(CC#N)=CC=4)CC2CC3C1 ZHVZPYIHRWVGGN-UHFFFAOYSA-N 0.000 claims 1
- IGOFOIZMFDPXFX-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[2-fluoro-4-(trifluoromethyl)phenyl]methyl]adamantane-1-carboxamide Chemical compound FC1=CC(C(F)(F)F)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 IGOFOIZMFDPXFX-UHFFFAOYSA-N 0.000 claims 1
- QUQJBYKWVPKHLH-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[3-(trifluoromethoxy)phenyl]methyl]adamantane-1-carboxamide Chemical compound FC(F)(F)OC1=CC=CC(CNC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1 QUQJBYKWVPKHLH-UHFFFAOYSA-N 0.000 claims 1
- AHBOCROIEOYOJD-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[3-(trifluoromethyl)phenyl]methyl]adamantane-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1 AHBOCROIEOYOJD-UHFFFAOYSA-N 0.000 claims 1
- SPRQWWBCXORDGE-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]adamantane-1-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC(CNC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1 SPRQWWBCXORDGE-UHFFFAOYSA-N 0.000 claims 1
- OAKWHWFWQAZCPS-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[4-(dimethylamino)phenyl]methyl]adamantane-1-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 OAKWHWFWQAZCPS-UHFFFAOYSA-N 0.000 claims 1
- DMHNDIATLJMXSG-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[4-(trifluoromethoxy)phenyl]methyl]adamantane-1-carboxamide Chemical compound C1=CC(OC(F)(F)F)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 DMHNDIATLJMXSG-UHFFFAOYSA-N 0.000 claims 1
- FKPVUCDEBPQVKX-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[4-(trifluoromethyl)phenyl]methyl]adamantane-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 FKPVUCDEBPQVKX-UHFFFAOYSA-N 0.000 claims 1
- DJQZWKPCPNZOSU-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]adamantane-1-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(CNC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1 DJQZWKPCPNZOSU-UHFFFAOYSA-N 0.000 claims 1
- NWABQIWIIKEEOY-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]adamantane-1-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1CNC(=O)C1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 NWABQIWIIKEEOY-UHFFFAOYSA-N 0.000 claims 1
- ZTHQTVQMYXUCDK-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-cyclopropyladamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NC4CC4)CC2CC3C1 ZTHQTVQMYXUCDK-UHFFFAOYSA-N 0.000 claims 1
- LYOMAZKTRFWZCN-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-phenyladamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NC=4C=CC=CC=4)CC2CC3C1 LYOMAZKTRFWZCN-UHFFFAOYSA-N 0.000 claims 1
- AXFKEWMUIFXJKQ-UHFFFAOYSA-N 3-(4-fluorophenyl)-n-(pyridin-4-ylmethyl)adamantane-1-carboxamide Chemical compound C1=CC(F)=CC=C1C1(C2)CC(C3)(C(=O)NCC=4C=CN=CC=4)CC2CC3C1 AXFKEWMUIFXJKQ-UHFFFAOYSA-N 0.000 claims 1
- SGKXPNFCZIJCBW-UHFFFAOYSA-N 4-[[3-(4-chlorophenyl)-1-adamantyl]methylamino]phenol Chemical compound C1=CC(O)=CC=C1NCC1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 SGKXPNFCZIJCBW-UHFFFAOYSA-N 0.000 claims 1
- RJWLLQWLBMJCFD-UHFFFAOYSA-N 4-methylpiperazin-1-amine Chemical compound CN1CCN(N)CC1 RJWLLQWLBMJCFD-UHFFFAOYSA-N 0.000 claims 1
- FEAVBPISLDZSTH-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[[3-(4-chlorophenyl)-1-adamantyl]methyl]-1,3-thiazol-2-amine Chemical compound C1=CC(Cl)=CC=C1C(S1)=CN=C1NCC1(CC(C2)(C3)C=4C=CC(Cl)=CC=4)CC3CC2C1 FEAVBPISLDZSTH-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- FZBWRVIIECHXNG-UHFFFAOYSA-N n'-tert-butyl-n-[[3-(4-chlorophenyl)-1-adamantyl]methyl]propane-1,3-diamine Chemical compound C1C(CNCCCNC(C)(C)C)(C2)CC(C3)CC1CC32C1=CC=C(Cl)C=C1 FZBWRVIIECHXNG-UHFFFAOYSA-N 0.000 claims 1
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- XFCXCXFYLZCPTL-UHFFFAOYSA-N n-[[3-(aminomethyl)-2,4,5,6-tetrachlorophenyl]methyl]-3-(4-chlorophenyl)adamantane-1-carboxamide Chemical compound NCC1=C(Cl)C(Cl)=C(Cl)C(CNC(=O)C23CC4CC(CC(C4)(C3)C=3C=CC(Cl)=CC=3)C2)=C1Cl XFCXCXFYLZCPTL-UHFFFAOYSA-N 0.000 claims 1
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- GKCLMZCTDGKLBQ-UHFFFAOYSA-N n-benzyl-3-(4-chlorophenyl)adamantane-1-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1(C2)CC(C3)(C(=O)NCC=4C=CC=CC=4)CC2CC3C1 GKCLMZCTDGKLBQ-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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| RU2605698C1 (ru) * | 2015-12-23 | 2016-12-27 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Волгоградский государственный технический университет" (ВолгГТУ) | Производные 2-(адамант-2-ил)этиламина, обладающие потенциальной противовирусной активностью |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2529201C1 (ru) * | 2013-06-18 | 2014-09-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Волгоградский государственный технический университет" (ВолгГТУ) | Способ получения n-(2-гетероциклоалкил-1-илэтил)адамантан-2-аминов |
| RU2605698C1 (ru) * | 2015-12-23 | 2016-12-27 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Волгоградский государственный технический университет" (ВолгГТУ) | Производные 2-(адамант-2-ил)этиламина, обладающие потенциальной противовирусной активностью |
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| BRPI0611966A2 (pt) | 2012-08-28 |
| US8063248B2 (en) | 2011-11-22 |
| US20120095004A1 (en) | 2012-04-19 |
| MX2007015863A (es) | 2008-04-02 |
| JP5368789B2 (ja) | 2013-12-18 |
| WO2006138660A3 (en) | 2007-07-19 |
| IL187881A (en) | 2013-08-29 |
| AU2006261327B2 (en) | 2012-07-05 |
| RU2008100606A (ru) | 2009-07-27 |
| CA2612338C (en) | 2015-02-03 |
| US7338961B2 (en) | 2008-03-04 |
| WO2006138660A2 (en) | 2006-12-28 |
| EP1904439B1 (en) | 2014-11-26 |
| CN101248041B (zh) | 2013-11-20 |
| EP2314574A1 (en) | 2011-04-27 |
| ZA200800423B (en) | 2008-10-29 |
| KR101386282B1 (ko) | 2014-04-17 |
| US8557800B2 (en) | 2013-10-15 |
| USRE49811E1 (en) | 2024-01-23 |
| US20080167352A1 (en) | 2008-07-10 |
| CA2612338A1 (en) | 2006-12-28 |
| ES2528451T3 (es) | 2015-02-10 |
| JP2008546714A (ja) | 2008-12-25 |
| KR20080027352A (ko) | 2008-03-26 |
| US20060287317A1 (en) | 2006-12-21 |
| IL187881A0 (en) | 2008-03-20 |
| AU2006261327A1 (en) | 2006-12-28 |
| BRPI0611966B1 (pt) | 2022-05-03 |
| CN101248041A (zh) | 2008-08-20 |
| EP1904439A2 (en) | 2008-04-02 |
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