IL224159A - Isoxazolo [4,5– b] herbicidal pyridines - Google Patents

Info

Publication number

IL224159A

IL224159A IL224159A IL22415913A IL224159A IL 224159 A IL224159 A IL 224159A IL 224159 A IL224159 A IL 224159A IL 22415913 A IL22415913 A IL 22415913A IL 224159 A IL224159 A IL 224159A

Authority

IL

Israel

Prior art keywords

pyridine

methyl

alkyl

lsoxazolo

carboxylic acid

Prior art date

2010-07-22

Links

• Espacenet
• Global Dossier
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• DITTYRBIXKVOTK-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]pyridine Chemical class C1=CC=C2C=NOC2=N1 DITTYRBIXKVOTK-UHFFFAOYSA-N 0.000 title claims description 52
• 230000002363 herbicidal effect Effects 0.000 title description 21
• -1 C2-Ce-haloaikynyl Chemical group 0.000 claims description 253
• TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 237
• 229910052739 hydrogen Inorganic materials 0.000 claims description 119
• 239000001257 hydrogen Substances 0.000 claims description 118
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 116
• 239000002253 acid Substances 0.000 claims description 93
• 125000000623 heterocyclic group Chemical group 0.000 claims description 86
• 150000004702 methyl esters Chemical class 0.000 claims description 79
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 150000002367 halogens Chemical class 0.000 claims description 67
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 61
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 45
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 42
• 150000003222 pyridines Chemical class 0.000 claims description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• 125000004494 ethyl ester group Chemical group 0.000 claims description 36
• 150000003254 radicals Chemical group 0.000 claims description 36
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 32
• 150000002148 esters Chemical class 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 30
• 239000004009 herbicide Substances 0.000 claims description 26
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• CLOLPYPGRNCLCF-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC2=C1C=NO2 CLOLPYPGRNCLCF-UHFFFAOYSA-N 0.000 claims description 17
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004767 (C1-C4) haloalkoxy group Chemical group 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
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• 150000001735 carboxylic acids Chemical class 0.000 claims description 2
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• TWBYWOBDOCUKOW-ZQBYOMGUSA-N pyridine-4-carboxylic acid Chemical compound O[14C](=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-ZQBYOMGUSA-N 0.000 claims 101
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
• AKGNIBXGIPMDLE-UHFFFAOYSA-N pyridine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=C1.OC(=O)C1=CC=NC=C1 AKGNIBXGIPMDLE-UHFFFAOYSA-N 0.000 description 136
• 235000013350 formula milk Nutrition 0.000 description 106
• 150000001875 compounds Chemical class 0.000 description 88
• 239000000203 mixture Substances 0.000 description 84
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 150000002431 hydrogen Chemical class 0.000 description 55
• 241000196324 Embryophyta Species 0.000 description 50
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
• 238000000034 method Methods 0.000 description 26
• 239000000243 solution Substances 0.000 description 25
• 230000015572 biosynthetic process Effects 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
• 239000002904 solvent Substances 0.000 description 23
• 238000003786 synthesis reaction Methods 0.000 description 23
• 239000003053 toxin Substances 0.000 description 23
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
• 231100000765 toxin Toxicity 0.000 description 22
• 108700012359 toxins Proteins 0.000 description 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 239000011541 reaction mixture Substances 0.000 description 21
• 238000005160 1H NMR spectroscopy Methods 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
• 108090000623 proteins and genes Proteins 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 18
• 238000009472 formulation Methods 0.000 description 17
• 239000007787 solid Substances 0.000 description 17
• 238000011282 treatment Methods 0.000 description 17
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
• 102000004169 proteins and genes Human genes 0.000 description 16
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
• 240000008042 Zea mays Species 0.000 description 14
• 244000038559 crop plants Species 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
• 239000000049 pigment Substances 0.000 description 14
• 239000011734 sodium Substances 0.000 description 14
• 239000004480 active ingredient Substances 0.000 description 13
• 239000003112 inhibitor Substances 0.000 description 13
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 12
• 150000007513 acids Chemical class 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 11
• 235000005822 corn Nutrition 0.000 description 11
• 239000000839 emulsion Substances 0.000 description 11
• 238000001914 filtration Methods 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 239000000725 suspension Substances 0.000 description 11
• 229920000742 Cotton Polymers 0.000 description 10
• 241000219146 Gossypium Species 0.000 description 10
• 238000010790 dilution Methods 0.000 description 10
• 239000012895 dilution Substances 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
• 235000002595 Solanum tuberosum Nutrition 0.000 description 9
• 244000061456 Solanum tuberosum Species 0.000 description 9
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
• 238000007792 addition Methods 0.000 description 9
• 239000002270 dispersing agent Substances 0.000 description 9
• 239000008187 granular material Substances 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 239000007864 aqueous solution Substances 0.000 description 8
• 239000000969 carrier Substances 0.000 description 8
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 8
• 239000006185 dispersion Substances 0.000 description 8
• 101150102464 Cry1 gene Proteins 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 229960004132 diethyl ether Drugs 0.000 description 7
• 229940052303 ethers for general anesthesia Drugs 0.000 description 7
• 239000003960 organic solvent Substances 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
• 235000010469 Glycine max Nutrition 0.000 description 6
• 244000068988 Glycine max Species 0.000 description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• 125000003545 alkoxy group Chemical group 0.000 description 6
• 125000003282 alkyl amino group Chemical group 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 229940125904 compound 1 Drugs 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 229910052731 fluorine Inorganic materials 0.000 description 6
• 239000011737 fluorine Substances 0.000 description 6
• 230000000749 insecticidal effect Effects 0.000 description 6
• 238000002156 mixing Methods 0.000 description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 description 6
• 239000001301 oxygen Substances 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• 235000006008 Brassica napus var napus Nutrition 0.000 description 5
• 240000000385 Brassica napus var. napus Species 0.000 description 5
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
• 239000005562 Glyphosate Substances 0.000 description 5
• 235000003222 Helianthus annuus Nutrition 0.000 description 5
• 150000001340 alkali metals Chemical class 0.000 description 5
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
• 125000003342 alkenyl group Chemical group 0.000 description 5
• 230000000844 anti-bacterial effect Effects 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
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• 239000003795 chemical substances by application Substances 0.000 description 5
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• 150000002170 ethers Chemical class 0.000 description 5
• XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 5
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• 125000005843 halogen group Chemical group 0.000 description 5
• 239000006072 paste Substances 0.000 description 5
• 238000002360 preparation method Methods 0.000 description 5
• 150000003672 ureas Chemical class 0.000 description 5
• ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• 241000894006 Bacteria Species 0.000 description 4
• 241000335053 Beta vulgaris Species 0.000 description 4
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• 244000020551 Helianthus annuus Species 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 4
• 238000005481 NMR spectroscopy Methods 0.000 description 4
• 108020004511 Recombinant DNA Proteins 0.000 description 4
• 241000607479 Yersinia pestis Species 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
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• 150000001768 cations Chemical class 0.000 description 4
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• SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 4
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
• 241000894007 species Species 0.000 description 4
• 125000004434 sulfur atom Chemical group 0.000 description 4
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• 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 description 3
• 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 description 3
• 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 description 3
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