JP5089185B2 - コラーゲン産生抑制剤。 - Google Patents

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Publication number

JP5089185B2

JP5089185B2 JP2007021396A JP2007021396A JP5089185B2 JP 5089185 B2 JP5089185 B2 JP 5089185B2 JP 2007021396 A JP2007021396 A JP 2007021396A JP 2007021396 A JP2007021396 A JP 2007021396A JP 5089185 B2 JP5089185 B2 JP 5089185B2

Authority

JP

Japan

Prior art keywords

group

phenyl

substituent

lower alkyl

alkyl group

Prior art date

2006-02-02

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.)

Expired - Fee Related

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• 230000037319 collagen production Effects 0.000 title claims description 32
• 239000003112 inhibitor Substances 0.000 title claims description 29
• -1 N-methyl-N- (4-trifluoromethylbenzyl) -N- [6- (4-{[2- (4-piperonylpiperazin-1-yl) -2-oxoethyl] acetylamino} Phenoxy) pyridin-3-yl] -amine Chemical compound 0.000 claims description 1856
• 125000000217 alkyl group Chemical group 0.000 claims description 724
• 125000001424 substituent group Chemical group 0.000 claims description 422
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 293
• 150000001875 compounds Chemical class 0.000 claims description 247
• 125000005843 halogen group Chemical group 0.000 claims description 182
• 125000003545 alkoxy group Chemical group 0.000 claims description 137
• 125000003386 piperidinyl group Chemical group 0.000 claims description 124
• 125000004193 piperazinyl group Chemical group 0.000 claims description 102
• 150000003839 salts Chemical class 0.000 claims description 97
• 125000002252 acyl group Chemical group 0.000 claims description 95
• 150000001491 aromatic compounds Chemical class 0.000 claims description 85
• 125000002947 alkylene group Chemical group 0.000 claims description 71
• 125000004076 pyridyl group Chemical group 0.000 claims description 69
• 125000000623 heterocyclic group Chemical group 0.000 claims description 67
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 66
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 57
• 229910052757 nitrogen Inorganic materials 0.000 claims description 56
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 54
• 125000003277 amino group Chemical group 0.000 claims description 47
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 31
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
• 125000004434 sulfur atom Chemical group 0.000 claims description 23
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• 239000004480 active ingredient Substances 0.000 claims description 14
• 206010016654 Fibrosis Diseases 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 125000004450 alkenylene group Chemical group 0.000 claims description 11
• 230000004761 fibrosis Effects 0.000 claims description 11
• 208000019425 cirrhosis of liver Diseases 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
• 208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 206010061989 glomerulosclerosis Diseases 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• VYIRSVCHAJORFX-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]-2-methoxyphenoxy]pyridin-3-yl]-3,4-dichlorobenzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1OC)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(Cl)C(Cl)=C1 VYIRSVCHAJORFX-UHFFFAOYSA-N 0.000 claims description 3
• AKBBIACRZIXUJF-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]-2-methylphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C)C(C=C1C)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 AKBBIACRZIXUJF-UHFFFAOYSA-N 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• UGLGSVLDVIYPPG-UHFFFAOYSA-N n-[6-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-ethylamino]-2-methoxyphenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(CC)C(C=C1OC)=CC=C1OC(N=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 UGLGSVLDVIYPPG-UHFFFAOYSA-N 0.000 claims description 2
• UTDOZXYCDYINCC-UHFFFAOYSA-N 3,4-dichloro-n-[6-[4-[4-[[4-(2,2-dimethylpropanoyl)phenyl]methyl]piperazine-1-carbonyl]phenoxy]pyridin-3-yl]benzamide Chemical compound C1=CC(C(=O)C(C)(C)C)=CC=C1CN1CCN(C(=O)C=2C=CC(OC=3N=CC(NC(=O)C=4C=C(Cl)C(Cl)=CC=4)=CC=3)=CC=2)CC1 UTDOZXYCDYINCC-UHFFFAOYSA-N 0.000 claims 1
• RNJNSXZLBOACPE-UHFFFAOYSA-N n-[4-[4-[[2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-2-oxoethyl]-methylamino]phenoxy]phenyl]-4-(trifluoromethyl)benzamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)CN(C)C(C=C1)=CC=C1OC(C=C1)=CC=C1NC(=O)C1=CC=C(C(F)(F)F)C=C1 RNJNSXZLBOACPE-UHFFFAOYSA-N 0.000 claims 1
• IPVQHBSBOMALEV-UHFFFAOYSA-N n-[6-[4-[3-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-oxopropyl]phenoxy]pyridin-3-yl]-4-(trifluoromethyl)benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)NC(C=N1)=CC=C1OC(C=C1)=CC=C1CCC(=O)N1CCN(CC=2C=C3OCOC3=CC=2)CC1 IPVQHBSBOMALEV-UHFFFAOYSA-N 0.000 claims 1
• 229960005235 piperonyl butoxide Drugs 0.000 claims 1
• 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 211
• 125000004432 carbon atom Chemical group C* 0.000 description 209
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 165
• 125000001984 thiazolidinyl group Chemical group 0.000 description 115
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 109
• 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 64
• 125000004043 oxo group Chemical group O=* 0.000 description 62
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 60
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 59
• 125000002883 imidazolyl group Chemical group 0.000 description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 57
• 150000001412 amines Chemical class 0.000 description 56
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 50
• 125000001624 naphthyl group Chemical group 0.000 description 35
• 125000002541 furyl group Chemical group 0.000 description 34
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 34
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
• 238000000034 method Methods 0.000 description 31
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 31
• 239000002904 solvent Substances 0.000 description 31
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
• 125000000168 pyrrolyl group Chemical group 0.000 description 29
• 150000007514 bases Chemical class 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
• 125000000335 thiazolyl group Chemical group 0.000 description 24
• 239000002253 acid Substances 0.000 description 23
• 125000000714 pyrimidinyl group Chemical group 0.000 description 23
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 22
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 21
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 21
• 239000003638 chemical reducing agent Substances 0.000 description 20
• 125000003226 pyrazolyl group Chemical group 0.000 description 20
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 17
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 17
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 16
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 16
• 229910052799 carbon Inorganic materials 0.000 description 16
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 15
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 14
• 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 14
• 229910052727 yttrium Inorganic materials 0.000 description 14
• 125000001544 thienyl group Chemical group 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 125000003884 phenylalkyl group Chemical group 0.000 description 12
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 150000002170 ethers Chemical class 0.000 description 10
• 125000005493 quinolyl group Chemical group 0.000 description 10
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 9
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
• 150000001298 alcohols Chemical class 0.000 description 9
• 125000004414 alkyl thio group Chemical group 0.000 description 9
• 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 9
• 235000014113 dietary fatty acids Nutrition 0.000 description 9
• 229930195729 fatty acid Natural products 0.000 description 9
• 239000000194 fatty acid Substances 0.000 description 9
• 235000019253 formic acid Nutrition 0.000 description 9
• 239000012046 mixed solvent Substances 0.000 description 9
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• 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
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 150000008065 acid anhydrides Chemical class 0.000 description 8
• 125000001589 carboacyl group Chemical group 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 150000004665 fatty acids Chemical class 0.000 description 8
• 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 8
• 238000005984 hydrogenation reaction Methods 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 7
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 7
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
• 150000008282 halocarbons Chemical class 0.000 description 7
• 239000012442 inert solvent Substances 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• 239000008096 xylene Substances 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• 229910052736 halogen Inorganic materials 0.000 description 6
• 150000002367 halogens Chemical class 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 125000003831 tetrazolyl group Chemical group 0.000 description 6
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 5
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 5
• 108010037362 Extracellular Matrix Proteins Proteins 0.000 description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 5
• 125000000304 alkynyl group Chemical group 0.000 description 5
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
• 125000004429 atom Chemical group 0.000 description 5
• 230000003197 catalytic effect Effects 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 210000002744 extracellular matrix Anatomy 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 5
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 5
• 125000003452 oxalyl group Chemical class *C(=O)C(*)=O 0.000 description 5
• 239000007800 oxidant agent Substances 0.000 description 5
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
• 238000006722 reduction reaction Methods 0.000 description 5
• 150000003512 tertiary amines Chemical group 0.000 description 5
• 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 5
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 4
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 4
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 4
• 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 description 4
• 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 4
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• SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical group O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
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