IL122812A

IL122812A - History 4, 9 - Atheno-benzo (F) isoindole as a transfusion inhibitor, pharmaceutical preparations containing them and a process for their preparation

History 4, 9 - Atheno-benzo (F) isoindole as a transfusion inhibitor, pharmaceutical preparations containing them and a process for their preparation

Info

Publication number: IL122812A
Authority: IL; Israel
Prior art keywords: radical; phenyl; carbon atoms; mmol; benzo
Prior art date: 1995-07-10

Application number

IL12281296A

Other languages

English (en)

Hebrew (he)

Other versions

IL122812A0 (en

Original Assignee

Rhone Poulenc Rorer Sa

Priority date

1995-07-10

Filing date

1996-07-08

Publication date

2001-04-30

1996-07-08 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1998-08-16 Publication of IL122812A0 publication Critical patent/IL122812A0/xx

2001-04-30 Publication of IL122812A publication Critical patent/IL122812A/en

Links

238000002360 preparation method Methods 0.000 title claims description 14
238000000034 method Methods 0.000 title claims description 13
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
BCCQJSPIFXAUSP-UHFFFAOYSA-N 11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-1,3,5,7,9,12-hexaene Chemical class C1=CC=CC2=C(C=3C4=CNC=3)CCC4=C21 BCCQJSPIFXAUSP-UHFFFAOYSA-N 0.000 title description 2
239000003528 protein farnesyltransferase inhibitor Substances 0.000 title description 2
-1 vinylidene Chemical compound 0.000 claims abstract description 191
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 120
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 85
239000002253 acid Substances 0.000 claims abstract description 54
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 35
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 35
229910052760 oxygen Inorganic materials 0.000 claims abstract description 35
239000001301 oxygen Substances 0.000 claims abstract description 35
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims abstract description 26
230000003287 optical effect Effects 0.000 claims abstract description 15
125000001118 alkylidene group Chemical group 0.000 claims abstract description 10
150000003512 tertiary amines Chemical class 0.000 claims abstract description 6
125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 claims abstract description 3
150000004702 methyl esters Chemical class 0.000 claims description 149
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 69
125000000217 alkyl group Chemical group 0.000 claims description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
125000003277 amino group Chemical group 0.000 claims description 13
YOGSXUSGQUGHLY-UHFFFAOYSA-N C=1N=CC2(C=CC=CC=12)C(=O)N Chemical compound C=1N=CC2(C=CC=CC=12)C(=O)N YOGSXUSGQUGHLY-UHFFFAOYSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
150000008064 anhydrides Chemical class 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 10
238000007127 saponification reaction Methods 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
230000032050 esterification Effects 0.000 claims description 8
238000005886 esterification reaction Methods 0.000 claims description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
230000000269 nucleophilic effect Effects 0.000 claims description 7
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 3
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
239000012948 isocyanate Substances 0.000 claims description 3
150000002513 isocyanates Chemical class 0.000 claims description 3
238000007280 thionation reaction Methods 0.000 claims description 3
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 claims description 2
VORXAFJKNDAIRT-UHFFFAOYSA-N 1,2,3,6,7,8,8a,9-octahydrobenzo[f]isoindole-9a-carboxylic acid Chemical compound C1CCC2CC(CNC3)(C(=O)O)C3=CC2=C1 VORXAFJKNDAIRT-UHFFFAOYSA-N 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims 2
230000002152 alkylating effect Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
239000005977 Ethylene Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 465
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 282
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 173
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 165
238000002844 melting Methods 0.000 description 158
230000008018 melting Effects 0.000 description 158
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 156
239000000243 solution Substances 0.000 description 143
238000001819 mass spectrum Methods 0.000 description 139
239000000203 mixture Substances 0.000 description 131
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 126
239000000047 product Substances 0.000 description 121
239000000843 powder Substances 0.000 description 107
125000003118 aryl group Chemical group 0.000 description 106
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 94
230000002829 reductive effect Effects 0.000 description 92
238000010828 elution Methods 0.000 description 89
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 88
238000003756 stirring Methods 0.000 description 87
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 75
239000000741 silica gel Substances 0.000 description 75
229910002027 silica gel Inorganic materials 0.000 description 75
239000012074 organic phase Substances 0.000 description 72
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 70
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 69
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 61
229910000069 nitrogen hydride Inorganic materials 0.000 description 60
238000003818 flash chromatography Methods 0.000 description 58
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 53
239000013078 crystal Substances 0.000 description 52
150000003254 radicals Chemical class 0.000 description 50
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 49
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
238000010992 reflux Methods 0.000 description 49
239000000377 silicon dioxide Substances 0.000 description 49
229910052943 magnesium sulfate Inorganic materials 0.000 description 47
235000019341 magnesium sulphate Nutrition 0.000 description 47
239000011541 reaction mixture Substances 0.000 description 43
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 41
238000001914 filtration Methods 0.000 description 34
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 32
241000786363 Rhampholeon spectrum Species 0.000 description 31
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
239000012043 crude product Substances 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
239000003960 organic solvent Substances 0.000 description 27
239000003921 oil Substances 0.000 description 26
235000019198 oils Nutrition 0.000 description 26
238000001035 drying Methods 0.000 description 25
238000005406 washing Methods 0.000 description 24
125000006239 protecting group Chemical group 0.000 description 21
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 20
UFJFORSFXOLLEF-UHFFFAOYSA-N 10-[2-(2-methoxyphenyl)acetyl]-1-phenyl-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound COC1=CC=CC=C1CC(=O)C1C(C2(C3=CC=CC=C3C3CC2)C=2C=CC=CC=2)C3(C(O)=O)CN1 UFJFORSFXOLLEF-UHFFFAOYSA-N 0.000 description 19
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 19
239000007787 solid Substances 0.000 description 19
239000003054 catalyst Substances 0.000 description 17
239000002904 solvent Substances 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
238000000746 purification Methods 0.000 description 16
XBELTINRTJILHU-UHFFFAOYSA-N 1-phenyl-11-azatetracyclo[6.5.2.02,7.09,13]pentadeca-2,4,6-triene-9-carboxylic acid Chemical compound C1CC(C=2C3=CC=CC=2)C2(C(=O)O)CNCC2C31C1=CC=CC=C1 XBELTINRTJILHU-UHFFFAOYSA-N 0.000 description 15
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
125000004494 ethyl ester group Chemical group 0.000 description 15
DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
238000001953 recrystallisation Methods 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
238000001816 cooling Methods 0.000 description 13
239000000725 suspension Substances 0.000 description 13
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 description 11
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
102000016914 ras Proteins Human genes 0.000 description 11
108010014186 ras Proteins Proteins 0.000 description 11
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 10
239000006260 foam Substances 0.000 description 10
238000010438 heat treatment Methods 0.000 description 10
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
AJNHUROMHIHZPQ-UHFFFAOYSA-N C(C)(=O)C1NCC2(CC3=C(C(C12)C1=CC=CC=C1)C=CC=C3)C(=O)O Chemical compound C(C)(=O)C1NCC2(CC3=C(C(C12)C1=CC=CC=C1)C=CC=C3)C(=O)O AJNHUROMHIHZPQ-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
238000000605 extraction Methods 0.000 description 9
229910052740 iodine Inorganic materials 0.000 description 9
239000002609 medium Substances 0.000 description 9
239000012153 distilled water Substances 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
238000000926 separation method Methods 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
UZRXAZLNBVVCHM-XSVIJKGOSA-N COC1=CC=CC=C1C=CC(=O)N1C[C@](C(O)=O)([C@H]2C3=CC=CC=C3[C@]3(C=4C=CC=CC=4)CC2)[C@H]3C1 Chemical compound COC1=CC=CC=C1C=CC(=O)N1C[C@](C(O)=O)([C@H]2C3=CC=CC=C3[C@]3(C=4C=CC=CC=4)CC2)[C@H]3C1 UZRXAZLNBVVCHM-XSVIJKGOSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
150000004820 halides Chemical class 0.000 description 7
HPTPZJBSQUULAV-UHFFFAOYSA-N 11-[(2-methylpropan-2-yl)oxycarbonylamino]undecanoic acid Chemical compound CC(C)(C)OC(=O)NCCCCCCCCCCC(O)=O HPTPZJBSQUULAV-UHFFFAOYSA-N 0.000 description 6
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 6
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
230000009435 amidation Effects 0.000 description 6
238000007112 amidation reaction Methods 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 6
238000007327 hydrogenolysis reaction Methods 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
RGOJMRLSECAMJM-UHFFFAOYSA-N 2-(2-methoxyphenyl)-2-oxoacetic acid Chemical compound COC1=CC=CC=C1C(=O)C(O)=O RGOJMRLSECAMJM-UHFFFAOYSA-N 0.000 description 5
IQOSVINVIDSMQE-UHFFFAOYSA-N 2-(2-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=CC=C1C(=C)C(O)=O IQOSVINVIDSMQE-UHFFFAOYSA-N 0.000 description 5
FBJAXSOQQSJWGN-UHFFFAOYSA-N CC(=O)C1C2C(C3=CC=CC=C3CC2(CN1)C(=O)N)C4=CC=CC=C4 Chemical compound CC(=O)C1C2C(C3=CC=CC=C3CC2(CN1)C(=O)N)C4=CC=CC=C4 FBJAXSOQQSJWGN-UHFFFAOYSA-N 0.000 description 5
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