JP2006504737A - 選択的プロゲステロン受容体モジュレーターとしての５−置換７，９−ジフルオロ−５Ｈ−クロメノ［３，４−ｆ］キノリン化合物 - Google Patents

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Publication number

JP2006504737A

JP2006504737A JP2004543233A JP2004543233A JP2006504737A JP 2006504737 A JP2006504737 A JP 2006504737A JP 2004543233 A JP2004543233 A JP 2004543233A JP 2004543233 A JP2004543233 A JP 2004543233A JP 2006504737 A JP2006504737 A JP 2006504737A

Authority

JP

Japan

Prior art keywords

compound

difluoro

chromeno

quinoline

dihydro

Prior art date

2002-10-11

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.)

Pending

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• -1 5-Substituted 7,9-difluoro-5H-chromeno [3,4-f] quinoline compounds Chemical class 0.000 title claims description 53
• 239000002379 progesterone receptor modulator Substances 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 172
• 102000003998 progesterone receptors Human genes 0.000 claims abstract description 42
• 108090000468 progesterone receptors Proteins 0.000 claims abstract description 42
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 36
• 238000000034 method Methods 0.000 claims abstract description 35
• 230000001404 mediated effect Effects 0.000 claims abstract description 7
• 239000001257 hydrogen Substances 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 229910052801 chlorine Inorganic materials 0.000 claims description 46
• 229910052731 fluorine Inorganic materials 0.000 claims description 45
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 229910052794 bromium Inorganic materials 0.000 claims description 35
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 claims description 26
• 125000000217 alkyl group Chemical group 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 19
• 229910052740 iodine Inorganic materials 0.000 claims description 18
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 17
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 16
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• 125000005605 benzo group Chemical group 0.000 claims description 15
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 15
• YCSXPXWKALKBPL-UHFFFAOYSA-N 7,9-difluoro-2,2,4-trimethyl-5-prop-1-ynyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C3C(C#CC)OC4=C(F)C=C(F)C=C4C3=CC=C21 YCSXPXWKALKBPL-UHFFFAOYSA-N 0.000 claims description 12
• 125000001188 haloalkyl group Chemical group 0.000 claims description 12
• 238000006467 substitution reaction Methods 0.000 claims description 12
• WSGMASBULXYTQF-UHFFFAOYSA-N 5-(4-chloro-3-methylphenyl)-7,9-difluoro-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C12=C3C(C)=CC(C)(C)NC3=CC=C2C2=CC(F)=CC(F)=C2OC1C1=CC=C(Cl)C(C)=C1 WSGMASBULXYTQF-UHFFFAOYSA-N 0.000 claims description 11
• RKLQNCFKLYDVOV-UHFFFAOYSA-N 7,9-difluoro-2,2,4-trimethyl-5-prop-2-ynyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound FC1=CC(F)=C2OC(CC#C)C3=C4C(C)=CC(C)(C)NC4=CC=C3C2=C1 RKLQNCFKLYDVOV-UHFFFAOYSA-N 0.000 claims description 11
• 229940125773 compound 10 Drugs 0.000 claims description 10
• 239000000284 extract Substances 0.000 claims description 10
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• BFOOOBZCWDLNDY-UHFFFAOYSA-N 7,9-difluoro-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C12=C3C(C)=CC(C)(C)NC3=CC=C2C2=CC(F)=CC(F)=C2OC1C1=CC=CC(C(F)(F)F)=C1 BFOOOBZCWDLNDY-UHFFFAOYSA-N 0.000 claims description 8
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
• 230000004913 activation Effects 0.000 claims description 8
• 229940088597 hormone Drugs 0.000 claims description 8
• 239000005556 hormone Substances 0.000 claims description 8
• 239000000186 progesterone Substances 0.000 claims description 8
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 claims description 7
• 239000000651 prodrug Substances 0.000 claims description 7
• 229940002612 prodrug Drugs 0.000 claims description 7
• PWZKTXOSJPDFLP-UHFFFAOYSA-N 5-butyl-7,9-difluoro-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C3C(CCCC)OC4=C(F)C=C(F)C=C4C3=CC=C21 PWZKTXOSJPDFLP-UHFFFAOYSA-N 0.000 claims description 6
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
• 206010028980 Neoplasm Diseases 0.000 claims description 6
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 claims description 6
• 229940127204 compound 29 Drugs 0.000 claims description 6
• 229940127573 compound 38 Drugs 0.000 claims description 6
• PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims description 6
• 229960003387 progesterone Drugs 0.000 claims description 6
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 claims description 5
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 5
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 claims description 5
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims description 5
• OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims description 5
• STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 claims description 5
• DTCGZIAKXRSBAQ-AFPJDJCSSA-N (5z)-5-[(2,5-difluorophenyl)methylidene]-7,9-difluoro-2,2,4-trimethyl-1h-chromeno[3,4-f]quinoline Chemical compound C12=C3C(C)=CC(C)(C)NC3=CC=C2C2=CC(F)=CC(F)=C2O\C1=C/C1=CC(F)=CC=C1F DTCGZIAKXRSBAQ-AFPJDJCSSA-N 0.000 claims description 5
• LKKUHSLPKBJVHC-AFPJDJCSSA-N (5z)-7,9-difluoro-2,2,4-trimethyl-5-[(3-methylpyridin-4-yl)methylidene]-1h-chromeno[3,4-f]quinoline Chemical compound C12=C3C(C)=CC(C)(C)NC3=CC=C2C2=CC(F)=CC(F)=C2O\C1=C/C1=CC=NC=C1C LKKUHSLPKBJVHC-AFPJDJCSSA-N 0.000 claims description 5
• UXLAMDSBDMGMNF-RMORIDSASA-N (5z)-7,9-difluoro-5-[(5-fluoro-2-methoxyphenyl)methylidene]-2,2,4-trimethyl-1h-chromeno[3,4-f]quinoline Chemical compound COC1=CC=C(F)C=C1\C=C/1C2=C3C(C)=CC(C)(C)NC3=CC=C2C2=CC(F)=CC(F)=C2O\1 UXLAMDSBDMGMNF-RMORIDSASA-N 0.000 claims description 5
• DJVKZHMKLURAAF-RMORIDSASA-N (5z)-7,9-difluoro-5-[(5-fluoro-2-methylphenyl)methylidene]-2,2,4-trimethyl-1h-chromeno[3,4-f]quinoline Chemical compound C12=C3C(C)=CC(C)(C)NC3=CC=C2C2=CC(F)=CC(F)=C2O\C1=C/C1=CC(F)=CC=C1C DJVKZHMKLURAAF-RMORIDSASA-N 0.000 claims description 5
• VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 claims description 5
• 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 5
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 5
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims description 5
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 claims description 5
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 claims description 5
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 claims description 5
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 claims description 5
• JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 claims description 5
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 claims description 5
• 229940126657 Compound 17 Drugs 0.000 claims description 5
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 claims description 5
• 229940125810 compound 20 Drugs 0.000 claims description 5
• 229940125877 compound 31 Drugs 0.000 claims description 5
• 229940125807 compound 37 Drugs 0.000 claims description 5
• 229940126540 compound 41 Drugs 0.000 claims description 5
• 229940125900 compound 59 Drugs 0.000 claims description 5
• 229940126179 compound 72 Drugs 0.000 claims description 5
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 230000035558 fertility Effects 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 201000010260 leiomyoma Diseases 0.000 claims description 5
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 claims description 5
• 208000024891 symptom Diseases 0.000 claims description 5
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 claims description 4
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims description 4
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims description 4
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• MMGRHYVTTLMZJQ-UHFFFAOYSA-N tributyl-(5-methoxyfuran-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(OC)O1 MMGRHYVTTLMZJQ-UHFFFAOYSA-N 0.000 description 1
• OTMIHZHASCPXNT-UHFFFAOYSA-N tributyl-(5-methylfuran-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C)O1 OTMIHZHASCPXNT-UHFFFAOYSA-N 0.000 description 1
• GOFOMJMAFIFSDO-UHFFFAOYSA-N tributyl-(5-methylthiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=C(C)S1 GOFOMJMAFIFSDO-UHFFFAOYSA-N 0.000 description 1
• PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 238000010626 work up procedure Methods 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1