TW202451B - - Google Patents

Info

Publication number

TW202451B

TW202451B TW081106523A TW81106523A TW202451B TW 202451 B TW202451 B TW 202451B TW 081106523 A TW081106523 A TW 081106523A TW 81106523 A TW81106523 A TW 81106523A TW 202451 B TW202451 B TW 202451B

Authority

TW

Taiwan

Prior art keywords

compound

group

item

ministry

cns

Prior art date

1991-08-21

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims description 267
• 238000002360 preparation method Methods 0.000 claims description 209
• -1 alkenyl alkyne Chemical class 0.000 claims description 198
• 150000003230 pyrimidines Chemical class 0.000 claims description 113
• 229910052739 hydrogen Inorganic materials 0.000 claims description 107
• 238000006243 chemical reaction Methods 0.000 claims description 105
• 239000001257 hydrogen Substances 0.000 claims description 100
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 77
• 150000003839 salts Chemical class 0.000 claims description 76
• 239000002253 acid Substances 0.000 claims description 75
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 67
• 239000007789 gas Substances 0.000 claims description 63
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
• 150000002148 esters Chemical class 0.000 claims description 57
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 41
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
• 150000001412 amines Chemical group 0.000 claims description 38
• 125000003277 amino group Chemical group 0.000 claims description 36
• 238000004519 manufacturing process Methods 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 31
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
• 239000000203 mixture Substances 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 28
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 230000002079 cooperative effect Effects 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 19
• 239000003054 catalyst Substances 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 238000011049 filling Methods 0.000 claims description 17
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 13
• 239000000126 substance Substances 0.000 claims description 13
• 230000007062 hydrolysis Effects 0.000 claims description 12
• 238000006460 hydrolysis reaction Methods 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 238000011282 treatment Methods 0.000 claims description 11
• 239000004480 active ingredient Substances 0.000 claims description 10
• 230000001093 anti-cancer Effects 0.000 claims description 10
• 150000001733 carboxylic acid esters Chemical class 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
• 230000009467 reduction Effects 0.000 claims description 9
• 150000001336 alkenes Chemical class 0.000 claims description 8
• 230000002378 acidificating effect Effects 0.000 claims description 7
• 150000007942 carboxylates Chemical class 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 229910052700 potassium Inorganic materials 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• 230000015572 biosynthetic process Effects 0.000 claims description 4
• 230000000144 pharmacologic effect Effects 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 201000010099 disease Diseases 0.000 claims description 3
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
• 238000012856 packing Methods 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• 238000011156 evaluation Methods 0.000 claims description 2
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
• 238000000746 purification Methods 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 11
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
• OLNDOBBWCCBPJA-UHFFFAOYSA-N pyridine Chemical class C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 OLNDOBBWCCBPJA-UHFFFAOYSA-N 0.000 claims 2
• 125000006593 (C2-C3) alkynyl group Chemical group 0.000 claims 1
• AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 1
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
• 125000002355 alkine group Chemical group 0.000 claims 1
• 230000004071 biological effect Effects 0.000 claims 1
• 229910052797 bismuth Inorganic materials 0.000 claims 1
• JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
• BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 claims 1
• 229940025294 hemin Drugs 0.000 claims 1
• 239000000575 pesticide Substances 0.000 claims 1
• 238000000554 physical therapy Methods 0.000 claims 1
• WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 1
• 229960004641 rituximab Drugs 0.000 claims 1
• 239000010117 shenhua Substances 0.000 claims 1
• 125000005730 thiophenylene group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 197
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 166
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 158
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
• 238000003756 stirring Methods 0.000 description 92
• 239000002585 base Substances 0.000 description 78
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
• 239000002904 solvent Substances 0.000 description 74
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 73
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 68
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 66
• 239000000243 solution Substances 0.000 description 66
• 229960002989 glutamic acid Drugs 0.000 description 64
• 238000005481 NMR spectroscopy Methods 0.000 description 56
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 54
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 53
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 51
• 238000001816 cooling Methods 0.000 description 51
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 49
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 47
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
• 238000010898 silica gel chromatography Methods 0.000 description 42
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• 150000002430 hydrocarbons Chemical group 0.000 description 38
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• 239000005711 Benzoic acid Substances 0.000 description 34
• 235000010233 benzoic acid Nutrition 0.000 description 34
• 235000002639 sodium chloride Nutrition 0.000 description 33
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
• RCONKSIPFAYSJB-UHFFFAOYSA-N 1h-pyrrole-2,4-diamine Chemical compound NC1=CNC(N)=C1 RCONKSIPFAYSJB-UHFFFAOYSA-N 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• 238000004949 mass spectrometry Methods 0.000 description 30
• 230000000875 corresponding effect Effects 0.000 description 29
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 28
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 27
• 239000000047 product Substances 0.000 description 27
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 23
• 229910002027 silica gel Inorganic materials 0.000 description 23
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 20
• 229920006395 saturated elastomer Polymers 0.000 description 20
• 238000005160 1H NMR spectroscopy Methods 0.000 description 19
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 19
• 238000000605 extraction Methods 0.000 description 19
• 229930195733 hydrocarbon Chemical group 0.000 description 19
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
• 206010028980 Neoplasm Diseases 0.000 description 17
• 239000001273 butane Substances 0.000 description 17
• 238000010586 diagram Methods 0.000 description 17
• 239000012071 phase Substances 0.000 description 17
• 239000004215 Carbon black (E152) Chemical group 0.000 description 16
• XSIFPSYPOVKYCO-UHFFFAOYSA-N butyl benzoate Chemical compound CCCCOC(=O)C1=CC=CC=C1 XSIFPSYPOVKYCO-UHFFFAOYSA-N 0.000 description 16
• 239000011734 sodium Substances 0.000 description 16
• LYDRKKWPKKEMNZ-UHFFFAOYSA-N tert-butyl benzoate Chemical compound CC(C)(C)OC(=O)C1=CC=CC=C1 LYDRKKWPKKEMNZ-UHFFFAOYSA-N 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 235000011121 sodium hydroxide Nutrition 0.000 description 15
• VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 14
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 14
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
• AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 14
• 239000003513 alkali Substances 0.000 description 14
• 239000012267 brine Substances 0.000 description 14
• 150000002306 glutamic acid derivatives Chemical group 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• 238000010438 heat treatment Methods 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
• 201000011510 cancer Diseases 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 125000002541 furyl group Chemical group 0.000 description 12
• 230000002829 reductive effect Effects 0.000 description 12
• 239000013076 target substance Substances 0.000 description 12
• 108010022394 Threonine synthase Proteins 0.000 description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 102000004419 dihydrofolate reductase Human genes 0.000 description 11
• 150000002576 ketones Chemical class 0.000 description 11
• 239000007788 liquid Substances 0.000 description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• BJUPTJXRJDXLHF-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[d]pyrimidine Chemical class N1=CN=C2CCCC2=C1 BJUPTJXRJDXLHF-UHFFFAOYSA-N 0.000 description 10
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 10
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 10
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 10
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 10
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
• 150000003138 primary alcohols Chemical class 0.000 description 10
• 239000002689 soil Substances 0.000 description 10
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 9
• 239000002246 antineoplastic agent Substances 0.000 description 9
• 150000002084 enol ethers Chemical class 0.000 description 9
• 230000002401 inhibitory effect Effects 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 8
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
• 229910052796 boron Inorganic materials 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
• NNWIJYYGWUOBRK-UHFFFAOYSA-N pyrrolidine-2,4-diamine Chemical compound N1C(CC(C1)N)N NNWIJYYGWUOBRK-UHFFFAOYSA-N 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 7
• TWJVNKMWXNTSAP-UHFFFAOYSA-N azanium;hydroxide;hydrochloride Chemical compound [NH4+].O.[Cl-] TWJVNKMWXNTSAP-UHFFFAOYSA-N 0.000 description 7
• 230000033228 biological regulation Effects 0.000 description 7
• 230000008859 change Effects 0.000 description 7
• 239000012141 concentrate Substances 0.000 description 7
• 235000008504 concentrate Nutrition 0.000 description 7
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 7
• MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 7
• 125000004494 ethyl ester group Chemical group 0.000 description 7
• 238000001704 evaporation Methods 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• 239000002244 precipitate Substances 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
• 102000040350 B family Human genes 0.000 description 6
• 108091072128 B family Proteins 0.000 description 6
• ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 6
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
• XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 238000007239 Wittig reaction Methods 0.000 description 6
• 229940041181 antineoplastic drug Drugs 0.000 description 6
• 238000009833 condensation Methods 0.000 description 6
• 230000005494 condensation Effects 0.000 description 6
• 238000011161 development Methods 0.000 description 6
• 230000018109 developmental process Effects 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 239000004052 folic acid antagonist Substances 0.000 description 6
• 239000011630 iodine Substances 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
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