TW214554B

TW214554B -

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Publication number: TW214554B
Authority: TW; Taiwan
Prior art keywords: group; compound; formula; alkyl; methyl
Prior art date: 1991-02-07

Application number

TW081101181A

Other languages

English (en)

Chinese (zh)

Original Assignee

Roussel Uclaf

Priority date

1991-02-07

Filing date

1992-02-18

Publication date

1993-10-11

1991-02-07 Priority claimed from FR9101372A external-priority patent/FR2672597B1/fr

1991-08-20 Priority claimed from FR9110433A external-priority patent/FR2680511B1/fr

1991-11-20 Priority claimed from FR9114282A external-priority patent/FR2684671B1/fr

1992-02-18 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1993-10-11 Application granted granted Critical

1993-10-11 Publication of TW214554B publication Critical patent/TW214554B/zh

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125000000217 alkyl group Chemical group 0.000 claims abstract description 151
-1 nitro, sulpho, formyl Chemical group 0.000 claims abstract description 142
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 96
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 60
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 59
125000003342 alkenyl group Chemical group 0.000 claims abstract description 57
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 34
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
239000003814 drug Substances 0.000 claims abstract description 20
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 19
125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
125000002947 alkylene group Chemical group 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 113
239000007789 gas Substances 0.000 claims description 86
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
239000002253 acid Substances 0.000 claims description 59
125000004429 atom Chemical group 0.000 claims description 49
150000001335 aliphatic alkanes Chemical class 0.000 claims description 47
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 41
238000000034 method Methods 0.000 claims description 35
229910052717 sulfur Inorganic materials 0.000 claims description 35
239000000203 mixture Substances 0.000 claims description 33
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
125000004434 sulfur atom Chemical group 0.000 claims description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
230000033228 biological regulation Effects 0.000 claims description 30
125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
150000003839 salts Chemical group 0.000 claims description 28
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 27
239000004305 biphenyl Substances 0.000 claims description 25
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 23
238000004519 manufacturing process Methods 0.000 claims description 21
239000011593 sulfur Substances 0.000 claims description 21
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
125000003831 tetrazolyl group Chemical group 0.000 claims description 19
201000010099 disease Diseases 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 17
238000007639 printing Methods 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
235000010290 biphenyl Nutrition 0.000 claims description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
230000002079 cooperative effect Effects 0.000 claims description 12
150000007522 mineralic acids Chemical class 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
125000003386 piperidinyl group Chemical group 0.000 claims description 11
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
150000007524 organic acids Chemical class 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
206010041349 Somnolence Diseases 0.000 claims description 9
229940079593 drug Drugs 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 8
235000005985 organic acids Nutrition 0.000 claims description 8
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
208000024827 Alzheimer disease Diseases 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
150000003536 tetrazoles Chemical class 0.000 claims description 6
ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
206010019280 Heart failures Diseases 0.000 claims description 4
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
238000002399 angioplasty Methods 0.000 claims description 4
230000004064 dysfunction Effects 0.000 claims description 4
230000000968 intestinal effect Effects 0.000 claims description 4
208000010412 Glaucoma Diseases 0.000 claims description 3
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
208000037849 arterial hypertension Diseases 0.000 claims description 3
125000006267 biphenyl group Chemical group 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
230000002265 prevention Effects 0.000 claims description 3
238000007127 saponification reaction Methods 0.000 claims description 3
102000005862 Angiotensin II Human genes 0.000 claims description 2
101800000733 Angiotensin-2 Proteins 0.000 claims description 2
241000252234 Hypophthalmichthys nobilis Species 0.000 claims description 2
229950006323 angiotensin ii Drugs 0.000 claims description 2
229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
230000004217 heart function Effects 0.000 claims description 2
230000003907 kidney function Effects 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
208000005171 Dysmenorrhea Diseases 0.000 claims 3
230000009245 menopause Effects 0.000 claims 3
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 2
208000010877 cognitive disease Diseases 0.000 claims 2
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 2
239000010931 gold Substances 0.000 claims 2
229910052737 gold Inorganic materials 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
208000019901 Anxiety disease Diseases 0.000 claims 1
206010012735 Diarrhoea Diseases 0.000 claims 1
241000257303 Hymenoptera Species 0.000 claims 1
235000014676 Phragmites communis Nutrition 0.000 claims 1
241001674048 Phthiraptera Species 0.000 claims 1
206010046763 Uterine atony Diseases 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
230000003042 antagnostic effect Effects 0.000 claims 1
230000036506 anxiety Effects 0.000 claims 1
230000004872 arterial blood pressure Effects 0.000 claims 1
125000005265 dialkylamine group Chemical group 0.000 claims 1
150000002484 inorganic compounds Chemical class 0.000 claims 1
229910017053 inorganic salt Inorganic materials 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
208000028774 intestinal disease Diseases 0.000 claims 1
210000003734 kidney Anatomy 0.000 claims 1
230000004060 metabolic process Effects 0.000 claims 1
229910052751 metal Inorganic materials 0.000 claims 1
239000002184 metal Substances 0.000 claims 1
235000012149 noodles Nutrition 0.000 claims 1
150000002894 organic compounds Chemical class 0.000 claims 1
238000010422 painting Methods 0.000 claims 1
230000001629 suppression Effects 0.000 claims 1
210000004291 uterus Anatomy 0.000 claims 1
125000003118 aryl group Chemical group 0.000 abstract description 108
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 53
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 29
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 28
239000001257 hydrogen Substances 0.000 abstract description 26
125000003710 aryl alkyl group Chemical group 0.000 abstract description 23
150000002431 hydrogen Chemical class 0.000 abstract description 13
125000002252 acyl group Chemical group 0.000 abstract description 9
125000005110 aryl thio group Chemical group 0.000 abstract description 7
125000003545 alkoxy group Chemical group 0.000 abstract description 6
125000004104 aryloxy group Chemical group 0.000 abstract description 4
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 abstract description 4
125000003396 thiol group Chemical class [H]S* 0.000 abstract description 4
125000005018 aryl alkenyl group Chemical group 0.000 abstract description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract description 2
IKNZBNHVVQIRTO-UHFFFAOYSA-N 2h-tetrazole-5-carboxylic acid Chemical compound OC(=O)C=1N=NNN=1 IKNZBNHVVQIRTO-UHFFFAOYSA-N 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
239000000047 product Substances 0.000 description 165
239000002585 base Substances 0.000 description 110
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 59
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
238000002844 melting Methods 0.000 description 39
230000008018 melting Effects 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
150000002148 esters Chemical class 0.000 description 34
150000003254 radicals Chemical class 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
125000005842 heteroatom Chemical group 0.000 description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
239000002994 raw material Substances 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
238000004566 IR spectroscopy Methods 0.000 description 17
150000001412 amines Chemical class 0.000 description 17
102000004190 Enzymes Human genes 0.000 description 15
108090000790 Enzymes Proteins 0.000 description 15
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
238000010992 reflux Methods 0.000 description 14
125000000842 isoxazolyl group Chemical group 0.000 description 13
229910052760 oxygen Inorganic materials 0.000 description 13
239000001301 oxygen Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
238000006467 substitution reaction Methods 0.000 description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
239000012071 phase Substances 0.000 description 12
229910052700 potassium Inorganic materials 0.000 description 11
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 10
240000004808 Saccharomyces cerevisiae Species 0.000 description 10
238000010521 absorption reaction Methods 0.000 description 10
125000003277 amino group Chemical group 0.000 description 10
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 9
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
239000008280 blood Substances 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000004364 calculation method Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
239000000463 material Substances 0.000 description 9
239000011591 potassium Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
125000000168 pyrrolyl group Chemical group 0.000 description 8
SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical group [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 7
229910002651 NO3 Inorganic materials 0.000 description 7
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
150000001336 alkenes Chemical class 0.000 description 7
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 7
239000000284 extract Substances 0.000 description 7
229940093915 gynecological organic acid Drugs 0.000 description 7
125000000623 heterocyclic group Chemical group 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
125000002950 monocyclic group Chemical group 0.000 description 7
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
229910052704 radon Inorganic materials 0.000 description 7
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 6
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 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
239000004115 Sodium Silicate Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
230000008030 elimination Effects 0.000 description 6
238000003379 elimination reaction Methods 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000002757 morpholinyl group Chemical group 0.000 description 6
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 6
125000001624 naphthyl group Chemical group 0.000 description 6
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
230000008569 process Effects 0.000 description 6
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 6
229910052911 sodium silicate Inorganic materials 0.000 description 6
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
238000005406 washing Methods 0.000 description 6
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 5
101100274581 Caenorhabditis elegans chc-1 gene Proteins 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
125000001153 fluoro group Chemical group F* 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
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 description 5
229910000037 hydrogen sulfide Inorganic materials 0.000 description 5
239000007788 liquid Substances 0.000 description 5
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000002002 slurry Substances 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
125000000547 substituted alkyl group Chemical group 0.000 description 5
239000000052 vinegar Substances 0.000 description 5
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
101100518501 Mus musculus Spp1 gene Proteins 0.000 description 4
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