SK88597A3 - Merkaptoketones, merkaptoalcohols and preparation method thereof - Google Patents
Merkaptoketones, merkaptoalcohols and preparation method thereof Download PDFInfo
- Publication number
- SK88597A3 SK88597A3 SK885-97A SK88597A SK88597A3 SK 88597 A3 SK88597 A3 SK 88597A3 SK 88597 A SK88597 A SK 88597A SK 88597 A3 SK88597 A3 SK 88597A3
- Authority
- SK
- Slovakia
- Prior art keywords
- aryl
- hydroxyl
- alkyl
- optionally substituted
- acid
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- -1 amino, carboxyl Chemical group 0.000 claims abstract description 116
- 125000003118 aryl group Chemical group 0.000 claims abstract description 76
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 41
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 40
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 39
- 150000002367 halogens Chemical group 0.000 claims abstract description 37
- 125000005518 carboxamido group Chemical group 0.000 claims abstract description 35
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 22
- 150000002825 nitriles Chemical group 0.000 claims abstract description 17
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 16
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 28
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 28
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 28
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 27
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 26
- 150000003573 thiols Chemical class 0.000 claims description 26
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 150000002596 lactones Chemical class 0.000 claims description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 17
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 14
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002837 carbocyclic group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 14
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 14
- 125000002950 monocyclic group Chemical group 0.000 claims description 14
- 229930192474 thiophene Natural products 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 150000002019 disulfides Chemical group 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- 238000010511 deprotection reaction Methods 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- OVZJEOQHNFTDGG-HKFHRXRESA-N (2r)-2-[(2s)-2-[tert-butyl(dimethyl)silyl]oxy-3-tritylsulfanylpropyl]nonanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](C[C@@H](CCCCCCC)C(O)=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1 OVZJEOQHNFTDGG-HKFHRXRESA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 claims description 4
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- OVZJEOQHNFTDGG-KAODMTDESA-N (2r)-2-[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-3-tritylsulfanylpropyl]nonanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@@H](C[C@@H](CCCCCCC)C(O)=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1 OVZJEOQHNFTDGG-KAODMTDESA-N 0.000 claims description 2
- RCIWMOOXRHANIE-VAVYLYDRSA-N (2r)-2-[(2r)-2-hydroxy-3-tritylsulfanylpropyl]nonanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](O)C[C@@H](CCCCCCC)C(O)=O)C1=CC=CC=C1 RCIWMOOXRHANIE-VAVYLYDRSA-N 0.000 claims description 2
- RCIWMOOXRHANIE-IRPSRAIASA-N (2r)-2-[(2s)-2-hydroxy-3-tritylsulfanylpropyl]nonanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@@H](O)C[C@@H](CCCCCCC)C(O)=O)C1=CC=CC=C1 RCIWMOOXRHANIE-IRPSRAIASA-N 0.000 claims description 2
- PNKICJSNJYXQOE-BZUAXINKSA-N (2r)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-2-[(2r)-2-hydroxy-3-sulfanylpropyl]nonanamide Chemical compound CCCCCCC[C@H](C[C@@H](O)CS)C(=O)N[C@H](C(=O)NC)C(C)(C)C PNKICJSNJYXQOE-BZUAXINKSA-N 0.000 claims description 2
- PNKICJSNJYXQOE-OWCLPIDISA-N (2r)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-2-[(2s)-2-hydroxy-3-sulfanylpropyl]nonanamide Chemical compound CCCCCCC[C@H](C[C@H](O)CS)C(=O)N[C@H](C(=O)NC)C(C)(C)C PNKICJSNJYXQOE-OWCLPIDISA-N 0.000 claims description 2
- VQTLORQVBXFBRQ-DLFZDVPBSA-N (2r,4r)-4-[tert-butyl(dimethyl)silyl]oxy-2-(2-methylpropyl)-5-tritylsulfanylpentanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@@H](C[C@@H](CC(C)C)C(O)=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1 VQTLORQVBXFBRQ-DLFZDVPBSA-N 0.000 claims description 2
- GZGVHKUFKHWGGL-ATIYNZHBSA-N (2r,4r)-4-hydroxy-2-(2-methylpropyl)-5-tritylsulfanylpentanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](O)C[C@@H](CC(C)C)C(O)=O)C1=CC=CC=C1 GZGVHKUFKHWGGL-ATIYNZHBSA-N 0.000 claims description 2
- BYKICFUKEFQZFQ-SQDLTUCFSA-N (2r,4r)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-4-hydroxy-2-(2-methylpropyl)-5-tritylsulfanylpentanamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](O)C[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)C(C)(C)C)C1=CC=CC=C1 BYKICFUKEFQZFQ-SQDLTUCFSA-N 0.000 claims description 2
- VQTLORQVBXFBRQ-JOMNFKBKSA-N (2r,4s)-4-[tert-butyl(dimethyl)silyl]oxy-2-(2-methylpropyl)-5-tritylsulfanylpentanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@H](C[C@@H](CC(C)C)C(O)=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1 VQTLORQVBXFBRQ-JOMNFKBKSA-N 0.000 claims description 2
- GZGVHKUFKHWGGL-GJZUVCINSA-N (2r,4s)-4-hydroxy-2-(2-methylpropyl)-5-tritylsulfanylpentanoic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@@H](O)C[C@@H](CC(C)C)C(O)=O)C1=CC=CC=C1 GZGVHKUFKHWGGL-GJZUVCINSA-N 0.000 claims description 2
- BYKICFUKEFQZFQ-SATCGAIXSA-N (2r,4s)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-4-hydroxy-2-(2-methylpropyl)-5-tritylsulfanylpentanamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SC[C@@H](O)C[C@@H](CC(C)C)C(=O)N[C@H](C(=O)NC)C(C)(C)C)C1=CC=CC=C1 BYKICFUKEFQZFQ-SATCGAIXSA-N 0.000 claims description 2
- AEAXSTUFLQPPSC-ATIYNZHBSA-N (3r,5r)-3-(2-methylpropyl)-5-(tritylsulfanylmethyl)oxolan-2-one Chemical compound O1C(=O)[C@H](CC(C)C)C[C@@H]1CSC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEAXSTUFLQPPSC-ATIYNZHBSA-N 0.000 claims description 2
- QQMNSSVKXFNMSA-VAVYLYDRSA-N (3r,5r)-3-heptyl-5-(tritylsulfanylmethyl)oxolan-2-one Chemical compound O1C(=O)[C@H](CCCCCCC)C[C@@H]1CSC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 QQMNSSVKXFNMSA-VAVYLYDRSA-N 0.000 claims description 2
- AEAXSTUFLQPPSC-GJZUVCINSA-N (3r,5s)-3-(2-methylpropyl)-5-(tritylsulfanylmethyl)oxolan-2-one Chemical compound O1C(=O)[C@H](CC(C)C)C[C@H]1CSC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AEAXSTUFLQPPSC-GJZUVCINSA-N 0.000 claims description 2
- QQMNSSVKXFNMSA-IRPSRAIASA-N (3r,5s)-3-heptyl-5-(tritylsulfanylmethyl)oxolan-2-one Chemical compound O1C(=O)[C@H](CCCCCCC)C[C@H]1CSC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 QQMNSSVKXFNMSA-IRPSRAIASA-N 0.000 claims description 2
- SBUXXYOLAOXXPM-NXEZZACHSA-N C(C(C)C)[C@@H]1C[C@@H](OC1=O)CSC(C)=O Chemical compound C(C(C)C)[C@@H]1C[C@@H](OC1=O)CSC(C)=O SBUXXYOLAOXXPM-NXEZZACHSA-N 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- LDYVOKOOBHHZGZ-CHWSQXEVSA-N s-[[(2r,4r)-4-heptyl-5-oxooxolan-2-yl]methyl] ethanethioate Chemical compound CCCCCCC[C@@H]1C[C@H](CSC(C)=O)OC1=O LDYVOKOOBHHZGZ-CHWSQXEVSA-N 0.000 claims description 2
- LDYVOKOOBHHZGZ-OLZOCXBDSA-N s-[[(2s,4r)-4-heptyl-5-oxooxolan-2-yl]methyl] ethanethioate Chemical compound CCCCCCC[C@@H]1C[C@@H](CSC(C)=O)OC1=O LDYVOKOOBHHZGZ-OLZOCXBDSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 239000011593 sulfur Substances 0.000 claims 10
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 4
- 239000011260 aqueous acid Substances 0.000 claims 4
- 230000003301 hydrolyzing effect Effects 0.000 claims 4
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Substances CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 2
- 230000002862 amidating effect Effects 0.000 claims 2
- 230000009435 amidation Effects 0.000 claims 2
- 238000007112 amidation reaction Methods 0.000 claims 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 239000012026 peptide coupling reagents Substances 0.000 claims 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims 2
- HRWGYHPQWFMSOW-ANHUGMMASA-N (2r)-n-[(2s)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-2-(2-oxo-3-tritylsulfanylpropyl)nonanamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(SCC(=O)C[C@@H](CCCCCCC)C(=O)N[C@H](C(=O)NC)C(C)(C)C)C1=CC=CC=C1 HRWGYHPQWFMSOW-ANHUGMMASA-N 0.000 claims 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- MEFLFCXULJKYFR-JOCHJYFZSA-N CC(C)C[C@H](CC(=O)CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)N Chemical compound CC(C)C[C@H](CC(=O)CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)N MEFLFCXULJKYFR-JOCHJYFZSA-N 0.000 claims 1
- XPGSPCWROYKYRQ-MFNWSBMRSA-N CC(C)C[C@H](C[C@H](CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)C(N[C@@H](C)C(C)(C)CC(N)=O)=O Chemical compound CC(C)C[C@H](C[C@H](CSC(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)O[Si](C)(C)C(C)(C)C)C(N[C@@H](C)C(C)(C)CC(N)=O)=O XPGSPCWROYKYRQ-MFNWSBMRSA-N 0.000 claims 1
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical group O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
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- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
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- LCYCJMRWLXXHNY-UHFFFAOYSA-N s-[(2-oxooxolan-3-yl)methyl] ethanethioate Chemical compound CC(=O)SCC1CCOC1=O LCYCJMRWLXXHNY-UHFFFAOYSA-N 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Catalysts (AREA)
- Steroid Compounds (AREA)
- Fats And Perfumes (AREA)
- Pyridine Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67799496A | 1996-07-10 | 1996-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK88597A3 true SK88597A3 (en) | 1998-01-14 |
Family
ID=24720941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK885-97A SK88597A3 (en) | 1996-07-10 | 1997-06-30 | Merkaptoketones, merkaptoalcohols and preparation method thereof |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0818443B1 (no) |
| JP (1) | JPH1067737A (no) |
| KR (1) | KR980009233A (no) |
| CN (1) | CN1336367A (no) |
| AT (1) | ATE210113T1 (no) |
| AU (1) | AU731155B2 (no) |
| BR (1) | BR9703800A (no) |
| CA (1) | CA2208676A1 (no) |
| CZ (1) | CZ202597A3 (no) |
| DE (1) | DE69708770T2 (no) |
| DK (1) | DK0818443T3 (no) |
| ES (1) | ES2166048T3 (no) |
| HK (1) | HK1008215A1 (no) |
| HU (1) | HUP9701127A3 (no) |
| IL (1) | IL121125A0 (no) |
| NO (1) | NO308597B1 (no) |
| NZ (1) | NZ328288A (no) |
| PT (1) | PT818443E (no) |
| SK (1) | SK88597A3 (no) |
| TW (1) | TW424083B (no) |
| ZA (1) | ZA976121B (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU5292193A (en) * | 1992-10-02 | 1994-04-26 | Merck & Co., Inc. | N-(mercaptoacyl)peptidyl derivatives as antidegenerative agents |
| GB9308695D0 (en) * | 1993-04-27 | 1993-06-09 | Celltech Ltd | Peptidyl derivatives |
| US5831004A (en) * | 1994-10-27 | 1998-11-03 | Affymax Technologies N.V. | Inhibitors of metalloproteases, pharmaceutical compositions comprising same and methods of their use |
-
1997
- 1997-06-20 TW TW086108628A patent/TW424083B/zh not_active IP Right Cessation
- 1997-06-20 IL IL12112597A patent/IL121125A0/xx unknown
- 1997-06-23 CA CA002208676A patent/CA2208676A1/en not_active Abandoned
- 1997-06-26 CZ CZ972025A patent/CZ202597A3/cs unknown
- 1997-06-27 NO NO973004A patent/NO308597B1/no unknown
- 1997-06-30 BR BR9703800A patent/BR9703800A/pt active Search and Examination
- 1997-06-30 HU HU9701127A patent/HUP9701127A3/hu unknown
- 1997-06-30 SK SK885-97A patent/SK88597A3/sk unknown
- 1997-06-30 KR KR1019970031756A patent/KR980009233A/ko not_active Application Discontinuation
- 1997-07-08 JP JP9182181A patent/JPH1067737A/ja active Pending
- 1997-07-09 EP EP97305020A patent/EP0818443B1/en not_active Expired - Lifetime
- 1997-07-09 DK DK97305020T patent/DK0818443T3/da active
- 1997-07-09 ZA ZA976121A patent/ZA976121B/xx unknown
- 1997-07-09 AT AT97305020T patent/ATE210113T1/de not_active IP Right Cessation
- 1997-07-09 ES ES97305020T patent/ES2166048T3/es not_active Expired - Lifetime
- 1997-07-09 PT PT97305020T patent/PT818443E/pt unknown
- 1997-07-09 NZ NZ328288A patent/NZ328288A/xx unknown
- 1997-07-09 DE DE69708770T patent/DE69708770T2/de not_active Expired - Fee Related
- 1997-07-10 AU AU28571/97A patent/AU731155B2/en not_active Ceased
-
1998
- 1998-07-11 HK HK98109083A patent/HK1008215A1/xx not_active IP Right Cessation
-
2001
- 2001-04-17 CN CN01117103A patent/CN1336367A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0818443B1 (en) | 2001-12-05 |
| DE69708770D1 (de) | 2002-01-17 |
| DE69708770T2 (de) | 2002-08-08 |
| EP0818443A3 (en) | 1998-08-19 |
| NO308597B1 (no) | 2000-10-02 |
| NO973004D0 (no) | 1997-06-27 |
| DK0818443T3 (da) | 2002-04-02 |
| HK1008215A1 (en) | 1999-05-07 |
| AU731155B2 (en) | 2001-03-22 |
| ATE210113T1 (de) | 2001-12-15 |
| CZ202597A3 (cs) | 1998-09-16 |
| BR9703800A (pt) | 1998-08-18 |
| ZA976121B (en) | 1999-01-11 |
| JPH1067737A (ja) | 1998-03-10 |
| CA2208676A1 (en) | 1998-01-10 |
| CN1336367A (zh) | 2002-02-20 |
| IL121125A0 (en) | 1997-11-20 |
| KR980009233A (ko) | 1998-04-30 |
| NO973004L (no) | 1998-01-12 |
| NZ328288A (en) | 1999-01-28 |
| PT818443E (pt) | 2002-05-31 |
| ES2166048T3 (es) | 2002-04-01 |
| HUP9701127A3 (en) | 2000-08-28 |
| HU9701127D0 (en) | 1997-08-28 |
| EP0818443A2 (en) | 1998-01-14 |
| TW424083B (en) | 2001-03-01 |
| AU2857197A (en) | 1998-01-22 |
| HUP9701127A2 (hu) | 1999-02-01 |
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