MXPA03000363A - Derivados de hidrazida del acido pirrolidin-2-carboxilico para su uso como inhibidores de metaloproteasas. - Google Patents
Derivados de hidrazida del acido pirrolidin-2-carboxilico para su uso como inhibidores de metaloproteasas.Info
- Publication number
- MXPA03000363A MXPA03000363A MXPA03000363A MXPA03000363A MXPA03000363A MX PA03000363 A MXPA03000363 A MX PA03000363A MX PA03000363 A MXPA03000363 A MX PA03000363A MX PA03000363 A MXPA03000363 A MX PA03000363A MX PA03000363 A MXPA03000363 A MX PA03000363A
- Authority
- MX
- Mexico
- Prior art keywords
- sulfonyl
- hydrazide
- carboxylic acid
- mercapto
- methyl
- Prior art date
Links
- 239000003475 metalloproteinase inhibitor Substances 0.000 title 1
- CMCFIGZTTYAYIZ-UHFFFAOYSA-N pyrrolidine-2-carbohydrazide Chemical class NNC(=O)C1CCCN1 CMCFIGZTTYAYIZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 239000011701 zinc Substances 0.000 claims abstract description 11
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 11
- 102000004157 Hydrolases Human genes 0.000 claims abstract description 7
- 108090000604 Hydrolases Proteins 0.000 claims abstract description 7
- -1 arylcarbonylalkyl Chemical group 0.000 claims description 185
- 238000006243 chemical reaction Methods 0.000 claims description 112
- 239000002253 acid Substances 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 238000010511 deprotection reaction Methods 0.000 claims description 25
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
- 150000003573 thiols Chemical class 0.000 claims description 18
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 11
- 206010020772 Hypertension Diseases 0.000 claims description 10
- 208000031225 myocardial ischemia Diseases 0.000 claims description 10
- 210000000056 organ Anatomy 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 125000006418 4-methylphenylsulfonyl group Chemical group 0.000 claims description 9
- 201000001320 Atherosclerosis Diseases 0.000 claims description 9
- 208000002249 Diabetes Complications Diseases 0.000 claims description 9
- 206010012655 Diabetic complications Diseases 0.000 claims description 9
- 208000010412 Glaucoma Diseases 0.000 claims description 9
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- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
- 206010060862 Prostate cancer Diseases 0.000 claims description 9
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 9
- 206010040047 Sepsis Diseases 0.000 claims description 9
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 claims description 9
- 206010043540 Thromboangiitis obliterans Diseases 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 206010003119 arrhythmia Diseases 0.000 claims description 9
- 230000006793 arrhythmia Effects 0.000 claims description 9
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- 239000000824 cytostatic agent Substances 0.000 claims description 9
- 230000001085 cytostatic effect Effects 0.000 claims description 9
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- 230000005906 menstruation Effects 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
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- 208000002815 pulmonary hypertension Diseases 0.000 claims description 9
- 208000013223 septicemia Diseases 0.000 claims description 9
- LVVNTXNLOMBDBY-OCCSQVGLSA-N (2s,4r)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@@H](S)CN1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 LVVNTXNLOMBDBY-OCCSQVGLSA-N 0.000 claims description 8
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 8
- 206010014824 Endotoxic shock Diseases 0.000 claims description 8
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 8
- 206010040070 Septic Shock Diseases 0.000 claims description 8
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 8
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- 102000004190 Enzymes Human genes 0.000 claims description 7
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- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 230000001966 cerebroprotective effect Effects 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 6
- 201000011461 pre-eclampsia Diseases 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Chemical group 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 230000003511 endothelial effect Effects 0.000 claims description 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- CAUNCDOYBPOPMF-ZBFHGGJFSA-N (2s,4r)-1-(4-phenylphenyl)sulfonyl-4-sulfanylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@@H](S)CN1S(=O)(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 CAUNCDOYBPOPMF-ZBFHGGJFSA-N 0.000 claims 1
- ZEBOPHPQLJLNAY-RDGATRHJSA-N (2s,4r)-n'-(4-methylphenyl)sulfonyl-n'-(2-methylpropyl)-1-naphthalen-2-ylsulfonyl-4-sulfanylpyrrolidine-2-carbohydrazide Chemical compound O=C([C@H]1N(C[C@H](S)C1)S(=O)(=O)C=1C=C2C=CC=CC2=CC=1)NN(CC(C)C)S(=O)(=O)C1=CC=C(C)C=C1 ZEBOPHPQLJLNAY-RDGATRHJSA-N 0.000 claims 1
- WACNXHCZHTVBJM-UHFFFAOYSA-N 1,2,3,4,5-pentafluorobenzene Chemical group FC1=CC(F)=C(F)C(F)=C1F WACNXHCZHTVBJM-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 10
- 102000005741 Metalloproteases Human genes 0.000 abstract description 8
- 108010006035 Metalloproteases Proteins 0.000 abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 4
- 102000035195 Peptidases Human genes 0.000 abstract description 3
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- 206010047139 Vasoconstriction Diseases 0.000 abstract description 2
- 230000025033 vasoconstriction Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
- 239000007787 solid Substances 0.000 description 49
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 45
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- 229940093499 ethyl acetate Drugs 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 24
- 239000006260 foam Substances 0.000 description 22
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 229920005989 resin Polymers 0.000 description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
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- 238000003818 flash chromatography Methods 0.000 description 13
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 12
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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- PTDVPWWJRCOIIO-UHFFFAOYSA-N (4-methoxyphenyl)methanethiol Chemical compound COC1=CC=C(CS)C=C1 PTDVPWWJRCOIIO-UHFFFAOYSA-N 0.000 description 6
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- DASJFYAPNPUBGG-UHFFFAOYSA-N naphthalene-1-sulfonyl chloride Chemical compound C1=CC=C2C(S(=O)(=O)Cl)=CC=CC2=C1 DASJFYAPNPUBGG-UHFFFAOYSA-N 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
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- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 210000003606 umbilical vein Anatomy 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Hematology (AREA)
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- Transplantation (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00114948 | 2000-07-19 | ||
| PCT/EP2001/007995 WO2002006224A1 (en) | 2000-07-19 | 2001-07-11 | Pyrrolidine-2-carboxylic acid hydrazide derivatives for use as metalloprotease inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA03000363A true MXPA03000363A (es) | 2003-05-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA03000363A MXPA03000363A (es) | 2000-07-19 | 2001-07-11 | Derivados de hidrazida del acido pirrolidin-2-carboxilico para su uso como inhibidores de metaloproteasas. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6444829B1 (enExample) |
| EP (1) | EP1317428B1 (enExample) |
| JP (1) | JP2004504298A (enExample) |
| KR (1) | KR100580056B1 (enExample) |
| CN (1) | CN1318402C (enExample) |
| AR (1) | AR033543A1 (enExample) |
| AT (1) | ATE323673T1 (enExample) |
| AU (1) | AU2001276396A1 (enExample) |
| BR (1) | BR0112543A (enExample) |
| CA (1) | CA2415665A1 (enExample) |
| DE (1) | DE60118941T2 (enExample) |
| ES (1) | ES2261443T3 (enExample) |
| MX (1) | MXPA03000363A (enExample) |
| PA (1) | PA8522401A1 (enExample) |
| PE (1) | PE20020339A1 (enExample) |
| UY (1) | UY26844A1 (enExample) |
| WO (1) | WO2002006224A1 (enExample) |
| ZA (1) | ZA200300172B (enExample) |
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|---|---|---|---|---|
| US6589997B2 (en) * | 2001-06-29 | 2003-07-08 | North Shore-Long Island Jewish Health System | Small-molecule modulators of hepatocyte growth factor/scatter factor activities |
| CN1294120C (zh) * | 2003-10-21 | 2007-01-10 | 山东大学 | 吡咯烷类基质金属蛋白酶抑制剂及其应用 |
| AT509045B1 (de) | 2010-01-29 | 2011-06-15 | Planta Naturstoffe Vertriebsges M B H | Verbindungen zur behandlung von asthma bronchiale |
| CN103145572A (zh) * | 2013-03-20 | 2013-06-12 | 康化（上海）新药研发有限公司 | 天然产物氯化γ-正缬氨酸盐酸盐的不对称合成方法 |
| CN105712910B (zh) * | 2016-03-08 | 2017-06-06 | 北京化工大学 | （n‑芳基亚磺酰基）磺酰肼及其制备方法 |
| WO2021029158A1 (ja) * | 2019-08-09 | 2021-02-18 | サンアプロ株式会社 | スルホンアミド化合物、非イオン系光酸発生剤、およびフォトリソグラフィー用樹脂組成物 |
| CN113030292A (zh) * | 2021-01-29 | 2021-06-25 | 京博农化科技有限公司 | 一种对三氟甲氧基苯胺基甲酰肼含量的分析方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US493333A (en) * | 1893-03-14 | Air-heating furnace | ||
| CA1283906C (en) * | 1983-05-09 | 1991-05-07 | Makoto Sunagawa | .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF |
| IL117440A0 (en) * | 1995-03-31 | 1996-07-23 | Pfizer | Pyrrolidinyl hydroxamic acid compounds and their production process |
| ATE226193T1 (de) * | 1996-08-28 | 2002-11-15 | Procter & Gamble | Substituierte zyklische amine als metalloproteaseinhibitoren |
-
2001
- 2001-07-06 US US09/900,350 patent/US6444829B1/en not_active Expired - Fee Related
- 2001-07-11 AT AT01954031T patent/ATE323673T1/de not_active IP Right Cessation
- 2001-07-11 KR KR1020037000825A patent/KR100580056B1/ko not_active Expired - Fee Related
- 2001-07-11 DE DE60118941T patent/DE60118941T2/de not_active Expired - Fee Related
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- 2001-07-11 EP EP01954031A patent/EP1317428B1/en not_active Expired - Lifetime
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2003
- 2003-01-07 ZA ZA200300172A patent/ZA200300172B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR100580056B1 (ko) | 2006-05-12 |
| EP1317428A1 (en) | 2003-06-11 |
| DE60118941D1 (de) | 2006-05-24 |
| BR0112543A (pt) | 2003-07-01 |
| PE20020339A1 (es) | 2002-04-23 |
| ZA200300172B (en) | 2004-04-07 |
| EP1317428B1 (en) | 2006-04-19 |
| AR033543A1 (es) | 2003-12-26 |
| CA2415665A1 (en) | 2002-01-24 |
| AU2001276396A1 (en) | 2002-01-30 |
| JP2004504298A (ja) | 2004-02-12 |
| CN1443163A (zh) | 2003-09-17 |
| PA8522401A1 (es) | 2002-09-30 |
| KR20030024797A (ko) | 2003-03-26 |
| DE60118941T2 (de) | 2006-12-21 |
| US20020040048A1 (en) | 2002-04-04 |
| US6444829B1 (en) | 2002-09-03 |
| WO2002006224A1 (en) | 2002-01-24 |
| UY26844A1 (es) | 2002-01-31 |
| CN1318402C (zh) | 2007-05-30 |
| ATE323673T1 (de) | 2006-05-15 |
| ES2261443T3 (es) | 2006-11-16 |
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