HRP20030901A2 - Aromatic sulfone hydroxamates and their use as protease inhibitors - Google Patents
Aromatic sulfone hydroxamates and their use as protease inhibitorsInfo
- Publication number
- HRP20030901A2 HRP20030901A2 HR20030901A HRP20030901A HRP20030901A2 HR P20030901 A2 HRP20030901 A2 HR P20030901A2 HR 20030901 A HR20030901 A HR 20030901A HR P20030901 A HRP20030901 A HR P20030901A HR P20030901 A2 HRP20030901 A2 HR P20030901A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- group
- alkoxy
- carbocyclyl
- halogen
- Prior art date
Links
- -1 Aromatic sulfone Chemical class 0.000 title claims description 344
- 239000000137 peptide hydrolase inhibitor Substances 0.000 title description 2
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 857
- 150000001875 compounds Chemical class 0.000 claims description 653
- 229910052736 halogen Inorganic materials 0.000 claims description 471
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 429
- 150000003839 salts Chemical class 0.000 claims description 403
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 385
- 150000002367 halogens Chemical class 0.000 claims description 371
- 125000001424 substituent group Chemical group 0.000 claims description 353
- 125000000623 heterocyclic group Chemical group 0.000 claims description 333
- 125000000217 alkyl group Chemical group 0.000 claims description 297
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 202
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 190
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 185
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 153
- 125000005843 halogen group Chemical group 0.000 claims description 109
- 125000003342 alkenyl group Chemical group 0.000 claims description 101
- 125000005884 carbocyclylalkyl group Chemical group 0.000 claims description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
- 229930194542 Keto Natural products 0.000 claims description 73
- 125000000468 ketone group Chemical group 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 68
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 64
- 229910052799 carbon Inorganic materials 0.000 claims description 60
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 54
- 125000000304 alkynyl group Chemical group 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000003106 haloaryl group Chemical group 0.000 claims description 51
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 49
- 125000005027 hydroxyaryl group Chemical group 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 45
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 42
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 42
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 42
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 42
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 41
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 41
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 230000001575 pathological effect Effects 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 29
- 241000124008 Mammalia Species 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 21
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 21
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 19
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 19
- 125000004701 alkyl carbonyl alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 19
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 19
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 19
- 125000005059 halophenyl group Chemical group 0.000 claims description 19
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 18
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 18
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
- 108010003059 aggrecanase Proteins 0.000 claims description 16
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 16
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 14
- 230000006378 damage Effects 0.000 claims description 14
- 125000001041 indolyl group Chemical group 0.000 claims description 14
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 13
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 13
- 230000002401 inhibitory effect Effects 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 claims description 12
- 102100026802 72 kDa type IV collagenase Human genes 0.000 claims description 12
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 claims description 12
- 108010015302 Matrix metalloproteinase-9 Proteins 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 12
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 12
- 239000011159 matrix material Substances 0.000 claims description 12
- 125000002757 morpholinyl group Chemical group 0.000 claims description 12
- 125000002971 oxazolyl group Chemical group 0.000 claims description 12
- 125000003386 piperidinyl group Chemical group 0.000 claims description 12
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 12
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 12
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 claims description 11
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 11
- 125000004600 benzothiopyranyl group Chemical group S1C(C=CC2=C1C=CC=C2)* 0.000 claims description 11
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 11
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 11
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 11
- 125000005438 isoindazolyl group Chemical group 0.000 claims description 11
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 11
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 11
- 230000002265 prevention Effects 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 102100027995 Collagenase 3 Human genes 0.000 claims description 10
- 108050005238 Collagenase 3 Proteins 0.000 claims description 10
- 108010076557 Matrix Metalloproteinase 14 Proteins 0.000 claims description 10
- 102100030216 Matrix metalloproteinase-14 Human genes 0.000 claims description 10
- 102100030412 Matrix metalloproteinase-9 Human genes 0.000 claims description 10
- 102000005741 Metalloproteases Human genes 0.000 claims description 10
- 108010006035 Metalloproteases Proteins 0.000 claims description 10
- 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 10
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 10
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
- 101710151806 72 kDa type IV collagenase Proteins 0.000 claims description 9
- 208000019693 Lung disease Diseases 0.000 claims description 9
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 9
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 9
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 9
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 9
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 9
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 9
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims description 9
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 9
- 125000005969 isothiazolinyl group Chemical group 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
- 125000005880 oxathiolanyl group Chemical group 0.000 claims description 9
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 9
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 9
- 125000001425 triazolyl group Chemical group 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 230000003176 fibrotic effect Effects 0.000 claims description 8
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 8
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 8
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- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 8
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- 208000027418 Wounds and injury Diseases 0.000 claims description 7
- 125000002785 azepinyl group Chemical group 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 208000014674 injury Diseases 0.000 claims description 7
- 125000003585 oxepinyl group Chemical group 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 7
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 6
- 206010027476 Metastases Diseases 0.000 claims description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 230000009401 metastasis Effects 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 201000008482 osteoarthritis Diseases 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 125000003777 thiepinyl group Chemical group 0.000 claims description 6
- 210000001519 tissue Anatomy 0.000 claims description 6
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- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 229910006069 SO3H Inorganic materials 0.000 claims description 5
- 206010064390 Tumour invasion Diseases 0.000 claims description 5
- 230000009400 cancer invasion Effects 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000020084 Bone disease Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 4
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims description 4
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- 208000010125 myocardial infarction Diseases 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000028169 periodontal disease Diseases 0.000 claims description 4
- 230000005747 tumor angiogenesis Effects 0.000 claims description 4
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
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- 208000019425 cirrhosis of liver Diseases 0.000 claims description 3
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- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
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- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 208000022531 anorexia Diseases 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
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- 230000004054 inflammatory process Effects 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004650 C1-C8 alkynyl group Chemical group 0.000 claims 5
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- 125000005842 heteroatom Chemical group 0.000 claims 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- 102000043279 ADAM17 Human genes 0.000 claims 2
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- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims 2
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PL341379A1 (en) * | 1997-11-14 | 2001-04-09 | Searle & Co | Aromatic sulphone substituted hydroxamic acid as inhibitor of metalloprotease |
GB9901147D0 (en) * | 1999-01-19 | 1999-03-10 | Merck Sharp & Dohme | Therapeutic agents |
US6683093B2 (en) * | 2000-05-12 | 2004-01-27 | Pharmacia Corporation | Aromatic sulfone hydroxamic acids and their use as protease inhibitors |
US20040024024A1 (en) * | 2001-05-11 | 2004-02-05 | Freskos John N. | Aromatic sulfone hydroxamates and their use as protease inhibitors |
US20050209278A1 (en) * | 2002-04-25 | 2005-09-22 | Mcdonald Joseph J | Piperidinyl- and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors |
WO2003091247A2 (en) * | 2002-04-25 | 2003-11-06 | Pharmacia Corporation | Piperidinyl-and piperazinyl-sulfonylmethyl hydroxamic acids and their use as protease inhibitors |
WO2004000811A1 (en) * | 2002-06-25 | 2003-12-31 | Pharmacia Corporation | Arylsulfonylhydroxamic acid and amide derivatives and their use as protease inhibitors |
EP1613269B1 (en) | 2003-04-04 | 2015-02-25 | Incyte Corporation | Compositions, methods and kits relating to her-2 cleavage |
WO2004098582A2 (en) * | 2003-05-07 | 2004-11-18 | The University Court Of The University Of Aberdeen | Ketones and reduced ketones as therapeutic agents for the treatment of bone conditions |
WO2005058884A2 (en) * | 2003-12-15 | 2005-06-30 | Japan Tobacco Inc. | Cyclopropane compounds and pharmaceutical use thereof |
WO2005061448A1 (en) * | 2003-12-24 | 2005-07-07 | Monash University | Compositions and methods for treating vascular conditions |
US20050250789A1 (en) * | 2004-04-20 | 2005-11-10 | Burns David M | Hydroxamic acid derivatives as metalloprotease inhibitors |
US7709516B2 (en) * | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
BRPI0720043A2 (pt) | 2006-12-15 | 2014-01-07 | Abbott Lab | Composto oxadiazol |
WO2014031784A1 (en) | 2012-08-23 | 2014-02-27 | Alios Biopharma, Inc. | Compounds for the treatment of paramoxyvirus viral infections |
MX2016016507A (es) | 2014-06-12 | 2017-04-27 | Cedars Sinai Medical Center | Composiciones y metodos para tratar canceres. |
CN104292180A (zh) * | 2014-10-12 | 2015-01-21 | 湖南华腾制药有限公司 | 一种恶二唑衍生物的制备方法 |
CA3073810A1 (en) * | 2017-08-31 | 2019-03-07 | Ahammune Biosciences Private Limited | Thiophene-derived compounds, process for synthesis and use thereof |
KR102533605B1 (ko) * | 2018-01-10 | 2023-05-17 | 주식회사 라이조테크 | 신규한 페닐설포닐 옥사졸 유도체 및 이의 용도 |
EP4377321A1 (en) * | 2021-07-28 | 2024-06-05 | University of KwaZulu-Natal | Metallo-?-lactamase inhibitors |
CN117800921B (zh) * | 2024-02-28 | 2024-06-11 | 南京市鸿舜医药科技有限公司 | 一种咪唑烷二酮类hdac抑制剂、制备方法及应用 |
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JP3122161B2 (ja) | 1991-05-16 | 2001-01-09 | 武田薬品工業株式会社 | γ−ラクトン免疫抑制剤 |
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GB9320660D0 (en) | 1993-10-07 | 1993-11-24 | British Bio Technology | Inhibition of cytokine production |
GB9323165D0 (en) | 1993-11-10 | 1994-01-05 | Chiros Ltd | Compounds |
WO1995029892A1 (en) | 1994-04-28 | 1995-11-09 | The Du Pont Merck Pharmaceutical Company | Hydroxamic acid and amino acid derivatives and their use as anti-arthritic agents |
GB9416897D0 (en) | 1994-08-20 | 1994-10-12 | British Biotech Pharm | Metalloproteinase inhibitors |
CN1193978A (zh) | 1994-10-05 | 1998-09-23 | 奇罗斯恩有限公司 | 肽基化合物和它们作为金属蛋白酶抑制剂的医疗用途 |
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ES2183905T3 (es) | 1995-12-20 | 2003-04-01 | Hoffmann La Roche | Inhibidores de metaloproteasa de matriz. |
EP0871439B1 (en) | 1996-01-02 | 2004-03-31 | Aventis Pharmaceuticals Inc. | Substituted (aryl, heteroaryl, arylmethyl or heteroarylmethyl) hydroxamic acid compounds |
WO1997049679A1 (fr) | 1996-06-27 | 1997-12-31 | Ono Pharmaceutical Co., Ltd. | Derives d'aryle (sulfure, oxyde sulfonique et sulfone) et medicaments les contenant en tant que principe actif |
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PL341379A1 (en) | 1997-11-14 | 2001-04-09 | Searle & Co | Aromatic sulphone substituted hydroxamic acid as inhibitor of metalloprotease |
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IL137566A0 (en) | 1998-02-19 | 2001-07-24 | American Cyanamid Co | N-hydroxy-2-(alkyl, aryl or heteroaryl sulfanyl, sulfinyl or sulfonyl)-3-substituted-alkyl, aryl or heteroarylamides as matrix metalloproteinase inhibitors |
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WO2000059874A1 (en) | 1999-04-02 | 2000-10-12 | Du Pont Pharmaceuticals Company | NOVEL AMIDE DERIVATIVES AS INHIBITORS OF MATRIX METALLOPROTEINASES, TNF-α, AND AGGRECANASE |
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US6683093B2 (en) | 2000-05-12 | 2004-01-27 | Pharmacia Corporation | Aromatic sulfone hydroxamic acids and their use as protease inhibitors |
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- 2002-05-10 BR BR0209525-4A patent/BR0209525A/pt not_active IP Right Cessation
- 2002-05-10 IL IL15845402A patent/IL158454A0/xx unknown
- 2002-05-10 EP EP02729204A patent/EP1385836A2/en not_active Withdrawn
- 2002-05-10 US US10/142,737 patent/US6689794B2/en not_active Expired - Fee Related
- 2002-05-10 AR ARP020101724A patent/AR040928A1/es unknown
- 2002-05-10 PL PL02367487A patent/PL367487A1/xx unknown
- 2002-05-10 CZ CZ20032913A patent/CZ20032913A3/cs unknown
-
2003
- 2003-01-31 ZA ZA200308525A patent/ZA200308525B/en unknown
- 2003-09-05 US US10/657,034 patent/US6890928B2/en not_active Expired - Fee Related
- 2003-10-23 BG BG108285A patent/BG108285A/bg unknown
- 2003-10-29 IS IS7003A patent/IS7003A/is unknown
- 2003-11-07 HR HR20030901A patent/HRP20030901A2/hr not_active Application Discontinuation
- 2003-11-10 CO CO03099304A patent/CO5540386A2/es not_active Application Discontinuation
- 2003-11-10 NO NO20034995A patent/NO20034995L/no not_active Application Discontinuation
- 2003-11-11 EC EC2003004839A patent/ECSP034839A/es unknown
- 2003-11-11 CR CR7146A patent/CR7146A/es not_active Application Discontinuation
-
2004
- 2004-11-17 US US10/992,483 patent/US20050101641A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
IL158454A0 (en) | 2004-05-12 |
OA12602A (en) | 2006-06-09 |
US20040110805A1 (en) | 2004-06-10 |
AR040928A1 (es) | 2005-04-27 |
US20040010019A1 (en) | 2004-01-15 |
ZA200308525B (en) | 2005-02-17 |
ECSP034839A (es) | 2003-12-24 |
CZ20032913A3 (cs) | 2004-05-12 |
JP2004530691A (ja) | 2004-10-07 |
MXPA03010326A (es) | 2004-07-30 |
EA200301116A1 (ru) | 2004-06-24 |
BG108285A (bg) | 2004-09-30 |
WO2002092588A2 (en) | 2002-11-21 |
YU85403A (sh) | 2006-03-03 |
WO2002092588A3 (en) | 2003-02-27 |
KR20040018368A (ko) | 2004-03-03 |
NO20034995L (no) | 2003-12-16 |
EP1385836A2 (en) | 2004-02-04 |
CR7146A (es) | 2008-02-11 |
US6890928B2 (en) | 2005-05-10 |
US20050101641A1 (en) | 2005-05-12 |
AP2003002908A0 (en) | 2003-12-31 |
US6689794B2 (en) | 2004-02-10 |
PL367487A1 (en) | 2005-02-21 |
CA2446586A1 (en) | 2002-11-21 |
BR0209525A (pt) | 2004-03-09 |
HUP0304069A2 (hu) | 2004-04-28 |
CO5540386A2 (es) | 2005-07-29 |
IS7003A (is) | 2003-10-29 |
NO20034995D0 (no) | 2003-11-10 |
CN1764655A (zh) | 2006-04-26 |
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A1OB | Publication of a patent application | ||
OBST | Application withdrawn |