NO20023921L - Derivater av thiazepinylhydroksamisk syre som inhibitorer av matriks metalloproteinase - Google Patents

Derivater av thiazepinylhydroksamisk syre som inhibitorer av matriks metalloproteinase Download PDF

Info

Publication number: NO20023921L
Authority: NO; Norway
Prior art keywords: optionally substituted; alkanoyl; alkoxy; substituted; group containing
Prior art date: 2000-02-21

Application number

NO20023921A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023921D0 (no

Inventor

Masahiro Neya

Hitoshi Yamazaki

Kazuhiko Ohne

Yuki Sawada

Tsuyoshi Mizutani

Yoshimasa Imamura

Noriko Mukai

Original Assignee

Fujisawa Pharmaceutical Co

Priority date (The priority date 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 date listed.)

2000-02-21

Filing date

2002-08-19

Publication date

2002-10-11

2000-02-21 Priority claimed from AUPQ5751A external-priority patent/AUPQ575100A0/en

2000-07-06 Priority claimed from AUPQ8603A external-priority patent/AUPQ860300A0/en

2002-08-19 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

2002-08-19 Publication of NO20023921D0 publication Critical patent/NO20023921D0/no

2002-10-11 Publication of NO20023921L publication Critical patent/NO20023921L/no

Links

102000002274 Matrix Metalloproteinases Human genes 0.000 title claims abstract description 19
108010000684 Matrix Metalloproteinases Proteins 0.000 title claims abstract description 19
239000003112 inhibitor Substances 0.000 title claims abstract description 6
-1 Thiazepinyl hydroxamic Chemical compound 0.000 title claims description 2007
239000002253 acid Substances 0.000 title description 22
125000003545 alkoxy group Chemical group 0.000 claims abstract description 244
238000004519 manufacturing process Methods 0.000 claims abstract description 171
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 136
150000003839 salts Chemical class 0.000 claims abstract description 75
125000003118 aryl group Chemical group 0.000 claims abstract description 64
125000002252 acyl group Chemical group 0.000 claims abstract description 42
125000004104 aryloxy group Chemical group 0.000 claims abstract description 35
125000000304 alkynyl group Chemical group 0.000 claims abstract description 20
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 15
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
125000002947 alkylene group Chemical group 0.000 claims abstract description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
241000534944 Thia Species 0.000 claims abstract description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 5
125000001589 carboacyl group Chemical group 0.000 claims description 158
125000000217 alkyl group Chemical group 0.000 claims description 153
150000001875 compounds Chemical class 0.000 claims description 142
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 138
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 132
125000004433 nitrogen atom Chemical group N* 0.000 claims description 110
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 89
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 70
125000004434 sulfur atom Chemical group 0.000 claims description 63
238000006243 chemical reaction Methods 0.000 claims description 61
125000004430 oxygen atom Chemical group O* 0.000 claims description 61
229920006395 saturated elastomer Polymers 0.000 claims description 57
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 54
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 54
125000005236 alkanoylamino group Chemical group 0.000 claims description 52
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 45
229910052736 halogen Inorganic materials 0.000 claims description 38
150000002367 halogens Chemical group 0.000 claims description 38
125000005843 halogen group Chemical group 0.000 claims description 34
238000000034 method Methods 0.000 claims description 33
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 31
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 29
125000001544 thienyl group Chemical group 0.000 claims description 29
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 27
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 27
125000003435 aroyl group Chemical group 0.000 claims description 27
125000003342 alkenyl group Chemical group 0.000 claims description 26
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 24
125000002619 bicyclic group Chemical group 0.000 claims description 23
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 23
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 21
125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 21
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 20
125000005037 alkyl phenyl group Chemical group 0.000 claims description 19
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 19
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 19
125000004076 pyridyl group Chemical group 0.000 claims description 19
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 18
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 18
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 17
125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 17
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 17
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
125000004414 alkyl thio group Chemical group 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
125000002541 furyl group Chemical group 0.000 claims description 15
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 claims description 15
125000001624 naphthyl group Chemical group 0.000 claims description 15
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 14
230000002401 inhibitory effect Effects 0.000 claims description 14
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims description 13
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 13
108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 13
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 13
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 13
125000003816 2-hydroxybenzoyl group Chemical group OC1=C(C(=O)*)C=CC=C1 0.000 claims description 12
125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims description 12
125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 12
125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 12
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims description 12
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 12
125000005493 quinolyl group Chemical group 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 10
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
125000004802 cyanophenyl group Chemical group 0.000 claims description 8
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 claims description 7
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 claims description 7
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
239000000463 material Substances 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
102100037205 Sal-like protein 2 Human genes 0.000 claims description 6
101710192308 Sal-like protein 2 Proteins 0.000 claims description 6
102100040247 Tumor necrosis factor Human genes 0.000 claims description 6
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 6
125000005059 halophenyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
102000003390 tumor necrosis factor Human genes 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
239000004480 active ingredient Substances 0.000 claims description 5
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 4
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 4
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
231100000252 nontoxic Toxicity 0.000 claims description 4
230000003000 nontoxic effect Effects 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
241001465754 Metazoa Species 0.000 claims 1
230000010933 acylation Effects 0.000 claims 1
238000005917 acylation reaction Methods 0.000 claims 1
229940059260 amidate Drugs 0.000 claims 1
NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 claims 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 abstract 1
230000017074 necrotic cell death Effects 0.000 abstract 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 196
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
238000002360 preparation method Methods 0.000 description 163
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 102
239000000243 solution Substances 0.000 description 98
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 84
239000000203 mixture Substances 0.000 description 81
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 58
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
238000001816 cooling Methods 0.000 description 34
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000012267 brine Substances 0.000 description 28
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 26
229910052943 magnesium sulfate Inorganic materials 0.000 description 25
235000019341 magnesium sulphate Nutrition 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 23
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
239000002904 solvent Substances 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
239000000843 powder Substances 0.000 description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
239000012044 organic layer Substances 0.000 description 18
239000007787 solid Substances 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
125000004432 carbon atom Chemical group C* 0.000 description 16
239000005457 ice water Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
235000011054 acetic acid Nutrition 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 14
238000010898 silica gel chromatography Methods 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
229910052783 alkali metal Inorganic materials 0.000 description 12
239000003480 eluent Substances 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
239000012230 colorless oil Substances 0.000 description 11
150000002148 esters Chemical class 0.000 description 11
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 11
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
239000000725 suspension Substances 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
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 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
125000005116 aryl carbamoyl group Chemical group 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
229910052801 chlorine Inorganic materials 0.000 description 8
125000000068 chlorophenyl group Chemical group 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
125000002971 oxazolyl group Chemical group 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
102000029816 Collagenase Human genes 0.000 description 7
108060005980 Collagenase Proteins 0.000 description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
230000002411 adverse Effects 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
229960002424 collagenase Drugs 0.000 description 7
201000010099 disease Diseases 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
239000003921 oil Substances 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
238000010998 test method Methods 0.000 description 7
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
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UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
AXIJWBKQQICBMV-DAFXYXGESA-N methyl (7s)-7-(5-bromothiophen-2-yl)-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC)CC[C@@]1(C=1SC(Br)=CC=1)CC(=O)NOC1OCCCC1 AXIJWBKQQICBMV-DAFXYXGESA-N 0.000 description 1
LGNCKSVODDGGFL-AUPVMFHISA-N methyl (7s)-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-7-[5-[3-[(2-phenoxyacetyl)amino]phenyl]thiophen-2-yl]-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC)CC[C@@]1(C=1SC(=CC=1)C=1C=C(NC(=O)COC=2C=CC=CC=2)C=CC=1)CC(=O)NOC1OCCCC1 LGNCKSVODDGGFL-AUPVMFHISA-N 0.000 description 1
OGJZVEIZNANQAT-KRWDZBQOSA-N methyl (7s)-7-[5-(furan-2-yl)thiophen-2-yl]-7-[2-(hydroxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC)CC[C@]1(CC(=O)NO)C1=CC=C(C=2OC=CC=2)S1 OGJZVEIZNANQAT-KRWDZBQOSA-N 0.000 description 1
XRIIXMXYCIIECU-IAXKEJLGSA-N methyl (7s)-7-[5-(furan-2-yl)thiophen-2-yl]-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC)CC[C@@]1(C=1SC(=CC=1)C=1OC=CC=1)CC(=O)NOC1OCCCC1 XRIIXMXYCIIECU-IAXKEJLGSA-N 0.000 description 1
CFHSTYJCEUBFMY-NASUQTAISA-N methyl (7s)-7-[5-[3-(methoxycarbonylamino)phenyl]thiophen-2-yl]-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound COC(=O)NC1=CC=CC(C=2SC(=CC=2)[C@]2(CC(=O)NOC3OCCCC3)S(CCN(CC2)C(=O)OC)(=O)=O)=C1 CFHSTYJCEUBFMY-NASUQTAISA-N 0.000 description 1
DAMCFXSUEWCYON-NASUQTAISA-N methyl (7s)-7-[5-[3-(methylcarbamoylamino)phenyl]thiophen-2-yl]-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound CNC(=O)NC1=CC=CC(C=2SC(=CC=2)[C@]2(CC(=O)NOC3OCCCC3)S(CCN(CC2)C(=O)OC)(=O)=O)=C1 DAMCFXSUEWCYON-NASUQTAISA-N 0.000 description 1
ODJDOAPKGLRKLY-RXBHZZDJSA-N methyl (7s)-7-[5-[3-[(2-ethoxyacetyl)amino]phenyl]thiophen-2-yl]-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound CCOCC(=O)NC1=CC=CC(C=2SC(=CC=2)[C@]2(CC(=O)NOC3OCCCC3)S(CCN(CC2)C(=O)OC)(=O)=O)=C1 ODJDOAPKGLRKLY-RXBHZZDJSA-N 0.000 description 1
JLMFQDXDWNITAS-UHFFFAOYSA-N methyl 7-[2-(hydroxyamino)-2-oxoethyl]-7-[5-(4-methoxyphenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC)CCC1(CC(=O)NO)C1=CC=C(C=2C=CC(OC)=CC=2)S1 JLMFQDXDWNITAS-UHFFFAOYSA-N 0.000 description 1
125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
OHVBJIDXWCNKHB-YNMFNDETSA-N methyl n-[3-[5-[(7s)-4-methylsulfonyl-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepan-7-yl]thiophen-2-yl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC(C=2SC(=CC=2)[C@]2(CC(=O)NOC3OCCCC3)S(CCN(CC2)S(C)(=O)=O)(=O)=O)=C1 OHVBJIDXWCNKHB-YNMFNDETSA-N 0.000 description 1
229960001047 methyl salicylate Drugs 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
NDYAAZRKZRTLQC-UHFFFAOYSA-N n,n-diethylsulfamoyl chloride Chemical compound CCN(CC)S(Cl)(=O)=O NDYAAZRKZRTLQC-UHFFFAOYSA-N 0.000 description 1
CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 1
JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
WQEWZLQWJAZGAW-UHFFFAOYSA-N n-(2-methoxyethyl)-n-methylsulfamoyl chloride Chemical compound COCCN(C)S(Cl)(=O)=O WQEWZLQWJAZGAW-UHFFFAOYSA-N 0.000 description 1
HSSAYMBKANGHFZ-UHFFFAOYSA-N n-(oxan-2-yloxy)-2-[7-[5-[4-(1,3-oxazol-5-yl)phenyl]thiophen-2-yl]-1,1-dioxo-4-propanoyl-1,4-thiazepan-7-yl]acetamide Chemical compound O=S1(=O)CCN(C(=O)CC)CCC1(C=1SC(=CC=1)C=1C=CC(=CC=1)C=1OC=NC=1)CC(=O)NOC1OCCCC1 HSSAYMBKANGHFZ-UHFFFAOYSA-N 0.000 description 1
QJILDBSUHKANBZ-UHFFFAOYSA-N n-benzyl-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-7-[5-[4-(1,3-oxazol-5-yl)phenyl]thiophen-2-yl]-1,1-dioxo-1,4-thiazepane-4-carboxamide Chemical compound C1CCCOC1ONC(=O)CC(S(CC1)(=O)=O)(C=2SC(=CC=2)C=2C=CC(=CC=2)C=2OC=NC=2)CCN1C(=O)NCC1=CC=CC=C1 QJILDBSUHKANBZ-UHFFFAOYSA-N 0.000 description 1
BHHNUEPWNUZHQZ-UHFFFAOYSA-N n-cyclohexyl-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-7-[5-[4-(1,3-oxazol-5-yl)phenyl]thiophen-2-yl]-1,1-dioxo-1,4-thiazepane-4-carboxamide Chemical compound C1CCCOC1ONC(=O)CC(S(CC1)(=O)=O)(C=2SC(=CC=2)C=2C=CC(=CC=2)C=2OC=NC=2)CCN1C(=O)NC1CCCCC1 BHHNUEPWNUZHQZ-UHFFFAOYSA-N 0.000 description 1
DJZGHVXYFFQLBT-FQEVSTJZSA-N n-hydroxy-2-[(7s)-7-[5-[3-(methylcarbamoylamino)phenyl]thiophen-2-yl]-4-methylsulfonyl-1,1-dioxo-1,4-thiazepan-7-yl]acetamide Chemical compound CNC(=O)NC1=CC=CC(C=2SC(=CC=2)[C@]2(CC(=O)NO)S(CCN(CC2)S(C)(=O)=O)(=O)=O)=C1 DJZGHVXYFFQLBT-FQEVSTJZSA-N 0.000 description 1
PDXIRLKPZCPZFJ-VWLOTQADSA-N n-hydroxy-2-[(7s)-7-[5-[4-(1,3-oxazol-5-yl)phenyl]thiophen-2-yl]-1,1-dioxo-4-(thiophene-2-carbonyl)-1,4-thiazepan-7-yl]acetamide Chemical compound C([C@](S(CC1)(=O)=O)(CC(=O)NO)C=2SC(=CC=2)C=2C=CC(=CC=2)C=2OC=NC=2)CN1C(=O)C1=CC=CS1 PDXIRLKPZCPZFJ-VWLOTQADSA-N 0.000 description 1
NSNRTXSPJLSFDL-UHFFFAOYSA-N n-hydroxy-2-[7-[5-(4-methoxyphenyl)thiophen-2-yl]-4-methylsulfonyl-1,1-dioxo-1,4-thiazepan-7-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C2(CC(=O)NO)S(CCN(CC2)S(C)(=O)=O)(=O)=O)S1 NSNRTXSPJLSFDL-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
229910000480 nickel oxide Inorganic materials 0.000 description 1
NLXXVSKHVGDQAT-UHFFFAOYSA-N o-(oxan-2-yl)hydroxylamine Chemical compound NOC1CCCCO1 NLXXVSKHVGDQAT-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
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YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
MGIODZWPWVYAOR-UHFFFAOYSA-N phenyl n-cyclopropylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1CC1 MGIODZWPWVYAOR-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
229940116357 potassium thiocyanate Drugs 0.000 description 1
CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
210000001626 skin fibroblast Anatomy 0.000 description 1
WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-N sodium;cyanic acid Chemical compound [Na+].OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-N 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000012089 stop solution Substances 0.000 description 1
108091007196 stromelysin Proteins 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
FWHZFSKOKVQKNM-ZYZRXSCRSA-N tert-butyl (7s)-7-(5-bromothiophen-2-yl)-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC(C)(C)C)CC[C@@]1(C=1SC(Br)=CC=1)CC(=O)NOC1OCCCC1 FWHZFSKOKVQKNM-ZYZRXSCRSA-N 0.000 description 1
VMNMZHZMKATUJB-FQEVSTJZSA-N tert-butyl (7s)-7-(5-bromothiophen-2-yl)-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C=1C=C(Br)SC=1[C@@]1(CC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCS1(=O)=O VMNMZHZMKATUJB-FQEVSTJZSA-N 0.000 description 1
YQQWIELDAFGSQK-LJAQVGFWSA-N tert-butyl (7s)-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-7-[5-(4-propylphenyl)thiophen-2-yl]-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(CCC)=CC=C1C1=CC=C([C@]2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)S1 YQQWIELDAFGSQK-LJAQVGFWSA-N 0.000 description 1
OSNAIEYADPYSJC-SANMLTNESA-N tert-butyl (7s)-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-7-[5-[4-(trifluoromethoxy)phenyl]thiophen-2-yl]-1,4-thiazepane-4-carboxylate Chemical compound C=1C=C(C=2C=CC(OC(F)(F)F)=CC=2)SC=1[C@@]1(CC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCS1(=O)=O OSNAIEYADPYSJC-SANMLTNESA-N 0.000 description 1
PAJGGNXHNGBZOX-SANMLTNESA-N tert-butyl (7s)-7-[5-(4-chlorophenyl)thiophen-2-yl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)SC=1[C@@]1(CC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCS1(=O)=O PAJGGNXHNGBZOX-SANMLTNESA-N 0.000 description 1
BJOLJIMLXSNTAV-TUXUZCGSSA-N tert-butyl (7s)-7-[5-(furan-2-yl)thiophen-2-yl]-7-[2-(oxan-2-yloxyamino)-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC(C)(C)C)CC[C@@]1(C=1SC(=CC=1)C=1OC=CC=1)CC(=O)NOC1OCCCC1 BJOLJIMLXSNTAV-TUXUZCGSSA-N 0.000 description 1
ZSTVECUAFPHHSC-UHFFFAOYSA-N tert-butyl 1,1-dioxo-7-(4-phenoxyphenyl)-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OC1=CC=CC=C1 ZSTVECUAFPHHSC-UHFFFAOYSA-N 0.000 description 1
QMORWMKUVTUHBU-MHZLTWQESA-N tert-butyl 2-[(7s)-1,1-dioxo-4-(pyridine-2-carbonyl)-7-[5-[4-(trifluoromethoxy)phenyl]thiophen-2-yl]-1,4-thiazepan-7-yl]acetate Chemical compound C([C@](S(CC1)(=O)=O)(CC(=O)OC(C)(C)C)C=2SC(=CC=2)C=2C=CC(OC(F)(F)F)=CC=2)CN1C(=O)C1=CC=CC=N1 QMORWMKUVTUHBU-MHZLTWQESA-N 0.000 description 1
DXHCMFYWKLKUDZ-DEOSSOPVSA-N tert-butyl 2-[(7s)-1,1-dioxo-7-[5-(4-propylphenyl)thiophen-2-yl]-1,4-thiazepan-7-yl]acetate Chemical compound C1=CC(CCC)=CC=C1C1=CC=C([C@]2(CC(=O)OC(C)(C)C)S(CCNCC2)(=O)=O)S1 DXHCMFYWKLKUDZ-DEOSSOPVSA-N 0.000 description 1
YUQACHZFSVKJGM-BOXHHOBZSA-N tert-butyl 2-[(7s)-1,1-dioxo-7-[5-[4-(trifluoromethoxy)phenyl]thiophen-2-yl]-1,4-thiazepan-7-yl]acetate;hydrochloride Chemical compound Cl.C=1C=C(C=2C=CC(OC(F)(F)F)=CC=2)SC=1[C@@]1(CC(=O)OC(C)(C)C)CCNCCS1(=O)=O YUQACHZFSVKJGM-BOXHHOBZSA-N 0.000 description 1
KTQQEMHRNDYEFW-VWLOTQADSA-N tert-butyl 2-[(7s)-4-methylsulfonyl-1,1-dioxo-7-[5-(4-propylphenyl)thiophen-2-yl]-1,4-thiazepan-7-yl]acetate Chemical compound C1=CC(CCC)=CC=C1C1=CC=C([C@]2(CC(=O)OC(C)(C)C)S(CCN(CC2)S(C)(=O)=O)(=O)=O)S1 KTQQEMHRNDYEFW-VWLOTQADSA-N 0.000 description 1
BNRZKCQOADFPHP-HNNXBMFYSA-N tert-butyl 2-[(7s)-7-(5-bromothiophen-2-yl)-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C=1C=C(Br)SC=1[C@@]1(CC(=O)OC(C)(C)C)CCNCCS1(=O)=O BNRZKCQOADFPHP-HNNXBMFYSA-N 0.000 description 1
HQZDGLUZICPBNK-FQEVSTJZSA-N tert-butyl 2-[(7s)-7-(5-bromothiophen-2-yl)-1,1-dioxo-4-(thiophene-3-carbonyl)-1,4-thiazepan-7-yl]acetate Chemical compound C([C@](S(CC1)(=O)=O)(CC(=O)OC(C)(C)C)C=2SC(Br)=CC=2)CN1C(=O)C=1C=CSC=1 HQZDGLUZICPBNK-FQEVSTJZSA-N 0.000 description 1
HKUJJAIECIWZNZ-KRWDZBQOSA-N tert-butyl 2-[(7s)-7-(5-bromothiophen-2-yl)-4-(dimethylsulfamoyl)-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound O=S1(=O)CCN(S(=O)(=O)N(C)C)CC[C@]1(CC(=O)OC(C)(C)C)C1=CC=C(Br)S1 HKUJJAIECIWZNZ-KRWDZBQOSA-N 0.000 description 1
WXKMABZGOPJMMW-NRFANRHFSA-N tert-butyl 2-[(7s)-7-[5-(4-chlorophenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)SC=1[C@@]1(CC(=O)OC(C)(C)C)CCNCCS1(=O)=O WXKMABZGOPJMMW-NRFANRHFSA-N 0.000 description 1
VXXNTDRTDUUHQQ-QHCPKHFHSA-N tert-butyl 2-[(7s)-7-[5-(4-ethylphenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C1=CC(CC)=CC=C1C1=CC=C([C@]2(CC(=O)OC(C)(C)C)S(CCNCC2)(=O)=O)S1 VXXNTDRTDUUHQQ-QHCPKHFHSA-N 0.000 description 1
XOJSOFMUZKBLNB-MHZLTWQESA-N tert-butyl 2-[(7s)-7-[5-(4-methoxyphenyl)thiophen-2-yl]-1,1-dioxo-4-(thiophene-3-carbonyl)-1,4-thiazepan-7-yl]acetate Chemical compound C1=CC(OC)=CC=C1C1=CC=C([C@]2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)C2=CSC=C2)(=O)=O)S1 XOJSOFMUZKBLNB-MHZLTWQESA-N 0.000 description 1
ZGUUJKXMNYUTMF-UHFFFAOYSA-N tert-butyl 2-[7-(5-naphthalen-2-ylthiophen-2-yl)-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C=1C=C(C=2C=C3C=CC=CC3=CC=2)SC=1C1(CC(=O)OC(C)(C)C)CCNCCS1(=O)=O ZGUUJKXMNYUTMF-UHFFFAOYSA-N 0.000 description 1
QTPYLKAMTHPFJR-UHFFFAOYSA-N tert-butyl 2-[7-[5-(4-cyanophenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C=1C=C(C=2C=CC(=CC=2)C#N)SC=1C1(CC(=O)OC(C)(C)C)CCNCCS1(=O)=O QTPYLKAMTHPFJR-UHFFFAOYSA-N 0.000 description 1
DJWQDYGQTWFOKQ-UHFFFAOYSA-N tert-butyl 2-[7-[5-(4-ethoxyphenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate;hydrochloride Chemical compound Cl.C1=CC(OCC)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCNCC2)(=O)=O)S1 DJWQDYGQTWFOKQ-UHFFFAOYSA-N 0.000 description 1
NHGSMAGVPVURCC-UHFFFAOYSA-N tert-butyl 2-[7-[5-(4-fluorophenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C=1C=C(C=2C=CC(F)=CC=2)SC=1C1(CC(=O)OC(C)(C)C)CCNCCS1(=O)=O NHGSMAGVPVURCC-UHFFFAOYSA-N 0.000 description 1
ZODZXGBMXXLPMR-UHFFFAOYSA-N tert-butyl 2-[7-[5-(4-methylphenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C1=CC(C)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCNCC2)(=O)=O)S1 ZODZXGBMXXLPMR-UHFFFAOYSA-N 0.000 description 1
RLBJVYHAAAHBFE-UHFFFAOYSA-N tert-butyl 2-[7-[5-(4-methylsulfanylphenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C1=CC(SC)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCNCC2)(=O)=O)S1 RLBJVYHAAAHBFE-UHFFFAOYSA-N 0.000 description 1
YIIKOXFGPQXWDI-UHFFFAOYSA-N tert-butyl 2-[7-[5-(5-chlorothiophen-2-yl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C=1C=C(C=2SC(Cl)=CC=2)SC=1C1(CC(=O)OC(C)(C)C)CCNCCS1(=O)=O YIIKOXFGPQXWDI-UHFFFAOYSA-N 0.000 description 1
KUHPRALEZHEVIH-UHFFFAOYSA-N tert-butyl 2-[7-[5-[4-(1,3-oxazol-2-yl)phenyl]thiophen-2-yl]-1,1-dioxo-4-(thiophene-3-carbonyl)-1,4-thiazepan-7-yl]acetate Chemical compound C1CS(=O)(=O)C(CC(=O)OC(C)(C)C)(C=2SC(=CC=2)C=2C=CC(=CC=2)C=2OC=CN=2)CCN1C(=O)C=1C=CSC=1 KUHPRALEZHEVIH-UHFFFAOYSA-N 0.000 description 1
FCQUTRVCRRYXLN-UHFFFAOYSA-N tert-butyl 2-[7-[5-[4-(methoxymethyl)phenyl]thiophen-2-yl]-1,1-dioxo-1,4-thiazepan-7-yl]acetate Chemical compound C1=CC(COC)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCNCC2)(=O)=O)S1 FCQUTRVCRRYXLN-UHFFFAOYSA-N 0.000 description 1
BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
ZLWCVPBRZFOAIW-UHFFFAOYSA-N tert-butyl 7-(4-phenoxyphenyl)-1,4-thiazepane-4-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCSC1C(C=C1)=CC=C1OC1=CC=CC=C1 ZLWCVPBRZFOAIW-UHFFFAOYSA-N 0.000 description 1
YQQWIELDAFGSQK-UHFFFAOYSA-N tert-butyl 7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-7-[5-(4-propylphenyl)thiophen-2-yl]-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)S1 YQQWIELDAFGSQK-UHFFFAOYSA-N 0.000 description 1
DJJCQOGHYDXWEI-UHFFFAOYSA-N tert-butyl 7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-[5-(4-methylsulfanylphenyl)thiophen-2-yl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(SC)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)S1 DJJCQOGHYDXWEI-UHFFFAOYSA-N 0.000 description 1
NKOFHAJWEDHPAA-UHFFFAOYSA-N tert-butyl 7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-7-[5-[4-(1,3-oxazol-5-yl)phenyl]thiophen-2-yl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C=2OC=NC=2)SC=1C1(CC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCS1(=O)=O NKOFHAJWEDHPAA-UHFFFAOYSA-N 0.000 description 1
LFMYSIRAEJGKIB-UHFFFAOYSA-N tert-butyl 7-[4-(4-chlorophenoxy)phenyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OC1=CC=C(Cl)C=C1 LFMYSIRAEJGKIB-UHFFFAOYSA-N 0.000 description 1
GPJUCKPDAHIQTB-UHFFFAOYSA-N tert-butyl 7-[4-(4-ethylphenoxy)phenyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(C2S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)C=C1 GPJUCKPDAHIQTB-UHFFFAOYSA-N 0.000 description 1
MEIDQDOTRGXPRO-UHFFFAOYSA-N tert-butyl 7-[4-(4-ethylphenoxy)phenyl]-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(C2SCCN(CC2)C(=O)OC(C)(C)C)C=C1 MEIDQDOTRGXPRO-UHFFFAOYSA-N 0.000 description 1
XZWYUPKSJVRRIP-UHFFFAOYSA-N tert-butyl 7-[4-(4-ethylphenoxy)phenyl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(CC)=CC=C1OC1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)C=C1 XZWYUPKSJVRRIP-UHFFFAOYSA-N 0.000 description 1
KYIIQSWFTICDCS-UHFFFAOYSA-N tert-butyl 7-[4-(4-fluorophenoxy)phenyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound O=S1(=O)CCN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 KYIIQSWFTICDCS-UHFFFAOYSA-N 0.000 description 1
JTDLGLHJQNOOQS-UHFFFAOYSA-N tert-butyl 7-[4-(4-fluorophenoxy)phenyl]-1,4-thiazepane-4-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCSC1C(C=C1)=CC=C1OC1=CC=C(F)C=C1 JTDLGLHJQNOOQS-UHFFFAOYSA-N 0.000 description 1
MMVKAHBGUOXBOK-UHFFFAOYSA-N tert-butyl 7-[4-(4-fluorophenoxy)phenyl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C=1C=C(OC=2C=CC(F)=CC=2)C=CC=1C1(CC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCS1(=O)=O MMVKAHBGUOXBOK-UHFFFAOYSA-N 0.000 description 1
OOFKXGYLLXHCDB-UHFFFAOYSA-N tert-butyl 7-[4-(4-methoxyphenoxy)phenyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C2S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)C=C1 OOFKXGYLLXHCDB-UHFFFAOYSA-N 0.000 description 1
USGIVONBVFZDOD-UHFFFAOYSA-N tert-butyl 7-[4-(4-methoxyphenoxy)phenyl]-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(C2SCCN(CC2)C(=O)OC(C)(C)C)C=C1 USGIVONBVFZDOD-UHFFFAOYSA-N 0.000 description 1
WORTVDNYFASZEA-UHFFFAOYSA-N tert-butyl 7-[4-(4-methylphenoxy)phenyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C2S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)C=C1 WORTVDNYFASZEA-UHFFFAOYSA-N 0.000 description 1
YLQWKLWZDNYRLI-UHFFFAOYSA-N tert-butyl 7-[5-(4-cyanophenyl)thiophen-2-yl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C=1C=C(C=2C=CC(=CC=2)C#N)SC=1C1(CC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCS1(=O)=O YLQWKLWZDNYRLI-UHFFFAOYSA-N 0.000 description 1
QZCVCAPWEABTKG-UHFFFAOYSA-N tert-butyl 7-[5-(4-ethoxyphenyl)thiophen-2-yl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)S1 QZCVCAPWEABTKG-UHFFFAOYSA-N 0.000 description 1
VXHSTSGFJFBTEM-UHFFFAOYSA-N tert-butyl 7-[5-(4-methylphenyl)thiophen-2-yl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(C)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)S1 VXHSTSGFJFBTEM-UHFFFAOYSA-N 0.000 description 1
MYLNIOYEBYDTMR-UHFFFAOYSA-N tert-butyl 7-[5-(5-chlorothiophen-2-yl)thiophen-2-yl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C=1C=C(C=2SC(Cl)=CC=2)SC=1C1(CC(=O)OC(C)(C)C)CCN(C(=O)OC(C)(C)C)CCS1(=O)=O MYLNIOYEBYDTMR-UHFFFAOYSA-N 0.000 description 1
SLKLHBPXSGUHDJ-UHFFFAOYSA-N tert-butyl 7-[5-[4-(methoxymethyl)phenyl]thiophen-2-yl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(COC)=CC=C1C1=CC=C(C2(CC(=O)OC(C)(C)C)S(CCN(CC2)C(=O)OC(C)(C)C)(=O)=O)S1 SLKLHBPXSGUHDJ-UHFFFAOYSA-N 0.000 description 1
WCTQFXGWMOKHLV-UHFFFAOYSA-N tert-butyl 7-[[5-(4-methoxyphenyl)thiophen-2-yl]methyl]-7-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-1,1-dioxo-1,4-thiazepane-4-carboxylate Chemical compound C1=CC(OC)=CC=C1C(S1)=CC=C1CC1(CC(=O)OC(C)(C)C)S(=O)(=O)CCN(C(=O)OC(C)(C)C)CC1 WCTQFXGWMOKHLV-UHFFFAOYSA-N 0.000 description 1
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
239000002753 trypsin inhibitor Substances 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
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- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/06—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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NO20023921A 2000-02-21 2002-08-19 Derivater av thiazepinylhydroksamisk syre som inhibitorer av matriks metalloproteinase NO20023921L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
AUPQ5751A AUPQ575100A0 (en)	2000-02-21	2000-02-21	Cyclic compound
AUPQ8603A AUPQ860300A0 (en)	2000-07-06	2000-07-06	Cyclic compound
PCT/JP2001/001206 WO2001060808A1 (en)	2000-02-21	2001-02-20	Thiazepinyl hydroxamic acid derivatives as matrix metalloproteinase inhibitors

Publications (2)

Publication Number	Publication Date
NO20023921D0 NO20023921D0 (no)	2002-08-19
NO20023921L true NO20023921L (no)	2002-10-11

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ID=25646264

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Application Number	Title	Priority Date	Filing Date
NO20023921A NO20023921L (no)	2000-02-21	2002-08-19	Derivater av thiazepinylhydroksamisk syre som inhibitorer av matriks metalloproteinase

Country Status (14)

Country	Link
US (1)	US6967197B2 (pl)
EP (1)	EP1259499A1 (pl)
JP (1)	JP2003523337A (pl)
KR (1)	KR20030000029A (pl)
CN (1)	CN1188404C (pl)
AR (1)	AR027952A1 (pl)
BR (1)	BR0108791A (pl)
CA (1)	CA2400862A1 (pl)
HU (1)	HUP0204501A2 (pl)
IL (1)	IL151197A0 (pl)
MX (1)	MXPA02008175A (pl)
NO (1)	NO20023921L (pl)
PL (1)	PL357084A1 (pl)
WO (1)	WO2001060808A1 (pl)

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* Cited by examiner, † Cited by third party
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JP2002226464A (ja) *	2001-01-30	2002-08-14	Sumitomo Pharmaceut Co Ltd	トリアリール類縁体およびその利用
AUPR755501A0 (en) *	2001-09-07	2001-09-27	Fujisawa Pharmaceutical Co., Ltd.	Cyclic compound
WO2003031431A1 (en)	2001-10-09	2003-04-17	Bristol-Myers Squibb Company	Cyclic sulfone derivatives as inhibitors of matrix metalloproteinases and/or tnf-$g(a) converting enzyme (tace)
US8507277B2 (en)	2003-10-24	2013-08-13	Gencia Corporation	Nonviral vectors for delivering polynucleotides
US8062891B2 (en)	2003-10-24	2011-11-22	Gencia Corporation	Nonviral vectors for delivering polynucleotides to plants
AU2004297533B2 (en)	2003-10-24	2010-04-29	Gencia Corporation	Methods and compositions for delivering polynucleotides
US8133733B2 (en)	2003-10-24	2012-03-13	Gencia Corporation	Nonviral vectors for delivering polynucleotides to target tissues
US20090123468A1 (en)	2003-10-24	2009-05-14	Gencia Corporation	Transducible polypeptides for modifying metabolism
KR100685222B1 (ko) *	2004-12-03	2007-02-22	우경건설 주식회사	이중 콘크리트 구조물
US20100028439A1 (en) *	2005-05-23	2010-02-04	Elan Pharma International Limited	Nanoparticulate stabilized anti-hypertensive compositions
CN104926707B (zh) *	2015-05-12	2017-10-27	江苏福瑞生物医药有限公司	一种药物中间体的合成方法

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ATE206073T1 (de) *	1995-12-29	2001-10-15	Novozymes As	Enzym enthaltende teilchen und flüssiges reinigungsmittelkonzentrat
HUP0000505A3 (en) *	1996-08-28	2001-12-28	Procter & Gamble	Saturated 7-9 membered heterocyclic n-hydroxycarboxamide derivatives and pharmaceutical compositions containing them
ATE226573T1 (de)	1996-08-28	2002-11-15	Procter & Gamble	Heterozyklische metalloproteaseinhibitoren
WO1998027069A1 (en)	1996-12-17	1998-06-25	Fujisawa Pharmaceutical Co., Ltd.	Piperazine compounds as inhibitors of mmp or tnf

2001
- 2001-02-20 MX MXPA02008175A patent/MXPA02008175A/es unknown
- 2001-02-20 PL PL01357084A patent/PL357084A1/pl not_active Application Discontinuation
- 2001-02-20 CA CA002400862A patent/CA2400862A1/en not_active Abandoned
- 2001-02-20 IL IL15119701A patent/IL151197A0/xx unknown
- 2001-02-20 HU HU0204501A patent/HUP0204501A2/hu unknown
- 2001-02-20 BR BR0108791-6A patent/BR0108791A/pt not_active Application Discontinuation
- 2001-02-20 US US10/203,627 patent/US6967197B2/en not_active Expired - Fee Related
- 2001-02-20 EP EP01906142A patent/EP1259499A1/en not_active Withdrawn
- 2001-02-20 JP JP2001560193A patent/JP2003523337A/ja not_active Withdrawn
- 2001-02-20 CN CNB018082432A patent/CN1188404C/zh not_active Expired - Fee Related
- 2001-02-20 WO PCT/JP2001/001206 patent/WO2001060808A1/en not_active Ceased
- 2001-02-20 KR KR1020027010721A patent/KR20030000029A/ko not_active Ceased
- 2001-02-21 AR ARP010100781A patent/AR027952A1/es unknown
2002
- 2002-08-19 NO NO20023921A patent/NO20023921L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
PL357084A1 (pl)	2004-07-12
IL151197A0 (en)	2003-04-10
US20030134849A1 (en)	2003-07-17
CN1188404C (zh)	2005-02-09
WO2001060808A1 (en)	2001-08-23
AR027952A1 (es)	2003-04-16
CA2400862A1 (en)	2001-08-23
US6967197B2 (en)	2005-11-22
NO20023921D0 (no)	2002-08-19
MXPA02008175A (es)	2003-05-23
KR20030000029A (ko)	2003-01-03
JP2003523337A (ja)	2003-08-05
BR0108791A (pt)	2004-04-27
CN1425010A (zh)	2003-06-18
HUP0204501A2 (hu)	2003-04-28
EP1259499A1 (en)	2002-11-27

Legal Events

Date	Code	Title	Description
2004-12-20	FC2A	Withdrawal, rejection or dismissal of laid open patent application

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WO2003018019A2 (en)	2003-03-06	New use of cyclic compounds
US6207686B1 (en)	2001-03-27	Endothelin antagonists
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