JP2003514806A - ベンゾオキサ−およびベンゾチアゾール類 - Google Patents
ベンゾオキサ−およびベンゾチアゾール類Info
- Publication number
- JP2003514806A JP2003514806A JP2001538887A JP2001538887A JP2003514806A JP 2003514806 A JP2003514806 A JP 2003514806A JP 2001538887 A JP2001538887 A JP 2001538887A JP 2001538887 A JP2001538887 A JP 2001538887A JP 2003514806 A JP2003514806 A JP 2003514806A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkyl
- compound
- salt form
- free
- Prior art date
- 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.)
- Pending
Links
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 108010087999 Steryl-Sulfatase Proteins 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 230000005764 inhibitory process Effects 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
- 102100038021 Steryl-sulfatase Human genes 0.000 claims abstract 3
- 238000006467 substitution reaction Methods 0.000 claims abstract 2
- 238000005849 sulfamoylation reaction Methods 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- -1 adamantan-2-ylidenemethyl Chemical group 0.000 claims description 44
- 150000003839 salts Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 15
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 12
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000005741 alkyl alkenyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 32
- 208000002874 Acne Vulgaris Diseases 0.000 abstract description 4
- 206010000496 acne Diseases 0.000 abstract description 4
- 230000002265 prevention Effects 0.000 abstract description 4
- 229940123142 Steroid sulfatase inhibitor Drugs 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 238000002844 melting Methods 0.000 description 60
- 230000008018 melting Effects 0.000 description 60
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- 239000003795 chemical substances by application Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 12
- 102000009134 Steryl-Sulfatase Human genes 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000003556 assay Methods 0.000 description 10
- 238000012937 correction Methods 0.000 description 10
- SAHAKBXWZLDNAA-UHFFFAOYSA-N 1,3-benzoxazol-6-ol Chemical compound OC1=CC=C2N=COC2=C1 SAHAKBXWZLDNAA-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- ROCVGJLXIARCAC-UHFFFAOYSA-N 4-aminobenzene-1,3-diol Chemical compound NC1=CC=C(O)C=C1O ROCVGJLXIARCAC-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 239000003098 androgen Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- UPPYOQWUJKAFSG-UHFFFAOYSA-N 1,3-benzoxazol-5-ol Chemical compound OC1=CC=C2OC=NC2=C1 UPPYOQWUJKAFSG-UHFFFAOYSA-N 0.000 description 4
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- LLJMPRKYLLJAEB-UHFFFAOYSA-N 4-aminobenzene-1,3-diol;hydron;chloride Chemical compound Cl.NC1=CC=C(O)C=C1O LLJMPRKYLLJAEB-UHFFFAOYSA-N 0.000 description 3
- 201000004384 Alopecia Diseases 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010020112 Hirsutism Diseases 0.000 description 3
- 101000661600 Homo sapiens Steryl-sulfatase Proteins 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 206010039792 Seborrhoea Diseases 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 206010068168 androgenetic alopecia Diseases 0.000 description 3
- 201000002996 androgenic alopecia Diseases 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 208000008742 seborrheic dermatitis Diseases 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000003270 steroid hormone Substances 0.000 description 3
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- ZJKIGJYINNUTDI-UHFFFAOYSA-N 2-(1-adamantylmethyl)-1,3-benzoxazol-6-ol Chemical compound C1C(C2)CC(C3)CC2CC13CC1=NC2=CC=C(O)C=C2O1 ZJKIGJYINNUTDI-UHFFFAOYSA-N 0.000 description 2
- ZBTBSFLZKDRODC-UHFFFAOYSA-N 2-[1-(2-hydroxy-2-adamantyl)pentyl]-1,3-benzoxazol-6-ol Chemical compound C1C(CC2C3)CC3CC1C2(O)C(CCCC)C1=NC2=CC=C(O)C=C2O1 ZBTBSFLZKDRODC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 230000006181 N-acylation Effects 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- IYKFYARMMIESOX-UHFFFAOYSA-N adamantanone Chemical compound C1C(C2)CC3CC1C(=O)C2C3 IYKFYARMMIESOX-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical compound C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000007083 alkoxycarbonylation reaction Methods 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000003920 cognitive function Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 229960003399 estrone Drugs 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 2
- 229960002847 prasterone Drugs 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 208000023958 prostate neoplasm Diseases 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 102220240796 rs553605556 Human genes 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 239000012049 topical pharmaceutical composition Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BREUOIWLJRZAFF-UHFFFAOYSA-N 1,3-benzothiazol-5-ol Chemical compound OC1=CC=C2SC=NC2=C1 BREUOIWLJRZAFF-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical compound CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 description 1
- VRKLIKLQANHNQI-UHFFFAOYSA-N 2-(1-adamantyl)-n-(2,4-dihydroxyphenyl)acetamide Chemical compound OC1=CC(O)=CC=C1NC(=O)CC1(C2)CC(C3)CC2CC3C1 VRKLIKLQANHNQI-UHFFFAOYSA-N 0.000 description 1
- NWRCKVZESFHTCA-UHFFFAOYSA-N 2-(2,2,2-triphenylethyl)-1,3-benzoxazol-6-ol Chemical compound O1C2=CC(O)=CC=C2N=C1CC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NWRCKVZESFHTCA-UHFFFAOYSA-N 0.000 description 1
- QGKPELNDXFFOQI-UHFFFAOYSA-N 2-(2-adamantylidene)-n-(2,4-dihydroxyphenyl)acetamide Chemical compound OC1=CC(O)=CC=C1NC(=O)C=C1C(C2)CC3CC2CC1C3 QGKPELNDXFFOQI-UHFFFAOYSA-N 0.000 description 1
- WBWYSPVZLQQIAX-UHFFFAOYSA-N 2-(2-adamantylidene)acetic acid Chemical compound C1C(C2)CC3CC1C(=CC(=O)O)C2C3 WBWYSPVZLQQIAX-UHFFFAOYSA-N 0.000 description 1
- PEICDXGGPDCLOZ-UHFFFAOYSA-N 2-(2-adamantylidenemethyl)-1,3-benzothiazol-6-ol Chemical compound C1C(CC2C3)CC3CC1C2=CC1=NC2=CC=C(O)C=C2S1 PEICDXGGPDCLOZ-UHFFFAOYSA-N 0.000 description 1
- VFOCAAKRTSAXGN-UHFFFAOYSA-N 2-(cyclobutylidenemethyl)-1,3-benzoxazol-5-ol Chemical compound N=1C2=CC(O)=CC=C2OC=1C=C1CCC1 VFOCAAKRTSAXGN-UHFFFAOYSA-N 0.000 description 1
- XZLCYQVXBXFVTQ-UHFFFAOYSA-N 2-(cycloheptylidenemethyl)-1,3-benzothiazol-5-ol Chemical compound N=1C2=CC(O)=CC=C2SC=1C=C1CCCCCC1 XZLCYQVXBXFVTQ-UHFFFAOYSA-N 0.000 description 1
- XLQQHPXZMPPLTQ-UHFFFAOYSA-N 2-(cycloheptylidenemethyl)-1,3-benzoxazol-5-ol Chemical compound N=1C2=CC(O)=CC=C2OC=1C=C1CCCCCC1 XLQQHPXZMPPLTQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- Neurosurgery (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9927439.1 | 1999-11-19 | ||
| GBGB9927439.1A GB9927439D0 (en) | 1999-11-19 | 1999-11-19 | Organic compounds |
| GB0007511A GB0007511D0 (en) | 2000-03-28 | 2000-03-28 | Organic compounds |
| GB0007511.9 | 2000-03-28 | ||
| PCT/EP2000/011475 WO2001036398A1 (en) | 1999-11-19 | 2000-11-17 | Benzoxa- and benzthiazoles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003514806A true JP2003514806A (ja) | 2003-04-22 |
| JP2003514806A5 JP2003514806A5 (enExample) | 2007-12-13 |
Family
ID=26243976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001538887A Pending JP2003514806A (ja) | 1999-11-19 | 2000-11-17 | ベンゾオキサ−およびベンゾチアゾール類 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6716865B1 (enExample) |
| EP (1) | EP1230227B1 (enExample) |
| JP (1) | JP2003514806A (enExample) |
| AR (1) | AR026504A1 (enExample) |
| AT (1) | ATE269853T1 (enExample) |
| AU (1) | AU1857701A (enExample) |
| CO (1) | CO5261573A1 (enExample) |
| DE (1) | DE60011801T2 (enExample) |
| DK (1) | DK1230227T3 (enExample) |
| ES (1) | ES2223620T3 (enExample) |
| HK (1) | HK1049329B (enExample) |
| PE (1) | PE20011012A1 (enExample) |
| PT (1) | PT1230227E (enExample) |
| TR (1) | TR200402432T4 (enExample) |
| WO (1) | WO2001036398A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR041952A1 (es) * | 2002-11-14 | 2005-06-01 | Novartis Ag | N-sulfonilaminotiazol |
| DE10260955A1 (de) * | 2002-12-20 | 2004-07-08 | Henkel Kgaa | Verwendung von Steroidsulfatase-Inhibitoren zur Verminderung von Haarausfall |
| RU2553476C2 (ru) * | 2007-08-02 | 2015-06-20 | Миллениум Фармасьютикалз, Инк. | Способ синтеза ингибиторов е1-активирующего фермента |
| CA2698814A1 (en) | 2007-09-17 | 2009-03-26 | Preglem S.A. | Treatment of oestrogen dependant conditions in pre-menopausal women |
| CN104926730B (zh) * | 2014-03-21 | 2017-07-21 | 中国科学院武汉岩土力学研究所 | 一种松香基咪唑啉类化合物及其合成方法和应用 |
| US11001564B2 (en) * | 2016-09-13 | 2021-05-11 | Arbutus Biopharma Corporation | Substituted chromane-8-carboxamide compounds and analogues thereof, and methods using same |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472418A (en) * | 1983-04-22 | 1984-09-18 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| JPH0347162A (ja) * | 1989-06-12 | 1991-02-28 | A H Robins Co Inc | 医薬品として有用な１個またはそれ以上のアミノスルホニルオキシ基を有する化合物類 |
| WO1999027935A1 (en) * | 1997-12-04 | 1999-06-10 | Sterix Limited | Steroid 3-o-sulphamate derivatives as inhibitors of oestrone sulphatase |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2868800A (en) | 1954-10-13 | 1959-01-13 | Upjohn Co | 6-ethoxybenzothiazole-2-sulfonamide |
| FI91869C (fi) | 1987-03-18 | 1994-08-25 | Tanabe Seiyaku Co | Menetelmä antidiabeettisena aineena käytettävien bensoksatsolijohdannaisten valmistamiseksi |
| US5273993A (en) | 1989-06-12 | 1993-12-28 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfonyloxy radicals useful as pharmaceuticals |
| US5194446A (en) | 1989-06-12 | 1993-03-16 | A. H. Robins Company, Incorporated | Compounds having one or more aminosulfaonyloxy radicals useful as pharmaceuticals |
| US5192785A (en) | 1989-09-03 | 1993-03-09 | A. H. Robins Company, Incorporated | Sulfamates as antiglaucoma agents |
| AU658646B2 (en) | 1991-05-10 | 1995-04-27 | Rhone-Poulenc Rorer International (Holdings) Inc. | Bis mono-and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
| WO1993011120A1 (en) | 1991-11-27 | 1993-06-10 | Zynaxis Technologies, Incorporated | Compounds, compositions and methods for binding bio-affecting substances to surface membranes of bio-particles |
| CA2144763A1 (en) | 1992-10-14 | 1994-04-28 | George D. Hartman | Fibrinogen receptor antagonists |
| EP0785927B1 (en) | 1994-10-12 | 2003-08-27 | Euroceltique S.A. | Novel benzoxazoles |
| US6169085B1 (en) * | 1995-03-10 | 2001-01-02 | G. D. Searle & Company | Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5677321A (en) | 1996-02-29 | 1997-10-14 | Synaptic Pharmaceutical Corporation | 5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands |
| US5709845A (en) | 1996-05-13 | 1998-01-20 | Rajagopalan; Raghavan | Tricyclic functional dyes for contrast enhancement in optical imaging |
| DE19653647A1 (de) | 1996-12-20 | 1998-06-25 | Hoechst Ag | Vitronectin - Rezeptorantagonisten, deren Herstellung sowie deren Verwendung |
| JPH10237053A (ja) | 1997-02-24 | 1998-09-08 | Sumitomo Chem Co Ltd | ベンゾチアゾール類の製造方法 |
| US6140051A (en) | 1997-07-21 | 2000-10-31 | Promega Biosciences, Inc. | Fluorescent dibenzazole derivatives and methods related thereto |
| GB9807779D0 (en) | 1998-04-09 | 1998-06-10 | Ciba Geigy Ag | Organic compounds |
| KR100597913B1 (ko) | 1998-06-18 | 2006-07-10 | 노파르티스 아게 | 벤즈아졸 화합물 및 그의 용도 |
-
2000
- 2000-11-03 CO CO00083906A patent/CO5261573A1/es not_active Application Discontinuation
- 2000-11-16 AR ARP000106055A patent/AR026504A1/es unknown
- 2000-11-17 ES ES00981270T patent/ES2223620T3/es not_active Expired - Lifetime
- 2000-11-17 AU AU18577/01A patent/AU1857701A/en not_active Abandoned
- 2000-11-17 PT PT00981270T patent/PT1230227E/pt unknown
- 2000-11-17 TR TR2004/02432T patent/TR200402432T4/xx unknown
- 2000-11-17 DE DE60011801T patent/DE60011801T2/de not_active Expired - Lifetime
- 2000-11-17 JP JP2001538887A patent/JP2003514806A/ja active Pending
- 2000-11-17 AT AT00981270T patent/ATE269853T1/de not_active IP Right Cessation
- 2000-11-17 EP EP00981270A patent/EP1230227B1/en not_active Expired - Lifetime
- 2000-11-17 WO PCT/EP2000/011475 patent/WO2001036398A1/en not_active Ceased
- 2000-11-17 DK DK00981270T patent/DK1230227T3/da active
- 2000-11-17 US US10/130,567 patent/US6716865B1/en not_active Expired - Fee Related
- 2000-11-17 HK HK02109307.7A patent/HK1049329B/en not_active IP Right Cessation
- 2000-11-17 PE PE2000001233A patent/PE20011012A1/es not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472418A (en) * | 1983-04-22 | 1984-09-18 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| JPH0347162A (ja) * | 1989-06-12 | 1991-02-28 | A H Robins Co Inc | 医薬品として有用な１個またはそれ以上のアミノスルホニルオキシ基を有する化合物類 |
| WO1999027935A1 (en) * | 1997-12-04 | 1999-06-10 | Sterix Limited | Steroid 3-o-sulphamate derivatives as inhibitors of oestrone sulphatase |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60011801D1 (de) | 2004-07-29 |
| WO2001036398A1 (en) | 2001-05-25 |
| CO5261573A1 (es) | 2003-03-31 |
| AU1857701A (en) | 2001-05-30 |
| DE60011801T2 (de) | 2005-07-14 |
| PT1230227E (pt) | 2004-10-29 |
| US6716865B1 (en) | 2004-04-06 |
| ATE269853T1 (de) | 2004-07-15 |
| HK1049329B (en) | 2005-03-24 |
| HK1049329A1 (en) | 2003-05-09 |
| AR026504A1 (es) | 2003-02-12 |
| EP1230227A1 (en) | 2002-08-14 |
| TR200402432T4 (tr) | 2004-12-21 |
| ES2223620T3 (es) | 2005-03-01 |
| PE20011012A1 (es) | 2001-10-02 |
| DK1230227T3 (da) | 2004-08-16 |
| EP1230227B1 (en) | 2004-06-23 |
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