OA12125A - Ox(adi)azolyl-hydroxamic acids useful as procollagen C-proteinase inhibitors. - Google Patents

Ox(adi)azolyl-hydroxamic acids useful as procollagen C-proteinase inhibitors. Download PDF

Info

Publication number: OA12125A
Authority: OA; OAPI
Prior art keywords: compound; formula; solution; mixture; préparation
Prior art date: 1999-12-23

Application number

OA1200200192A

Other languages

English (en)

Inventor

Simon Bailey

Stephane Billotte

Andrew Michael Derrick

Paul Vincent Fish

Kim James

Nicholas Murray Thomson

Original Assignee

Pfizer

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.)

1999-12-23

Filing date

2000-12-12

Publication date

2006-05-05

2000-12-12 Application filed by Pfizer filed Critical Pfizer

2006-05-05 Publication of OA12125A publication Critical patent/OA12125A/en

Links

108090000654 Bone morphogenetic protein 1 Proteins 0.000 title claims abstract description 47
102100028728 Bone morphogenetic protein 1 Human genes 0.000 title claims abstract description 47
229940019748 antifibrinolytic proteinase inhibitors Drugs 0.000 title description 2
239000000137 peptide hydrolase inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 300
229940002612 prodrug Drugs 0.000 claims abstract description 32
239000000651 prodrug Substances 0.000 claims abstract description 32
239000003112 inhibitor Substances 0.000 claims abstract description 21
150000003839 salts Chemical class 0.000 claims abstract description 16
239000000203 mixture Substances 0.000 claims description 278
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 217
229910052757 nitrogen Inorganic materials 0.000 claims description 119
239000002253 acid Substances 0.000 claims description 113
-1 4-methylpiperazinocarbonyl Chemical group 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 48
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
238000000034 method Methods 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 24
102100026802 72 kDa type IV collagenase Human genes 0.000 claims description 22
101710151806 72 kDa type IV collagenase Proteins 0.000 claims description 22
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 19
125000003118 aryl group Chemical group 0.000 claims description 18
102000000380 Matrix Metalloproteinase 1 Human genes 0.000 claims description 16
108010016113 Matrix Metalloproteinase 1 Proteins 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
108010076557 Matrix Metalloproteinase 14 Proteins 0.000 claims description 14
102100030216 Matrix metalloproteinase-14 Human genes 0.000 claims description 14
102100030412 Matrix metalloproteinase-9 Human genes 0.000 claims description 14
108010015302 Matrix metalloproteinase-9 Proteins 0.000 claims description 14
239000003153 chemical reaction reagent Substances 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
230000008569 process Effects 0.000 claims description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
125000006362 methylene amino carbonyl group Chemical group [H]N(C([*:2])=O)C([H])([H])[*:1] 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([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
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
150000001204 N-oxides Chemical class 0.000 claims description 3
239000002671 adjuvant Substances 0.000 claims description 3
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
150000004677 hydrates Chemical class 0.000 claims description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
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125000004429 atom Chemical group 0.000 claims description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 2
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SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 28
125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims 1
QZHKYOPXQSFVRT-UHFFFAOYSA-N 2-diethoxyphosphoryl-4-[(2-methylpropan-2-yl)oxy]-4-oxobutanoic acid Chemical compound CCOP(=O)(OCC)C(C(O)=O)CC(=O)OC(C)(C)C QZHKYOPXQSFVRT-UHFFFAOYSA-N 0.000 claims 1
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101150070727 CSNK2B gene Proteins 0.000 claims 1
102100027992 Casein kinase II subunit beta Human genes 0.000 claims 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
230000003213 activating effect Effects 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
238000006356 dehydrogenation reaction Methods 0.000 claims 1
UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
230000001404 mediated effect Effects 0.000 abstract description 5
239000012453 solvate Substances 0.000 abstract 1
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239000000243 solution Substances 0.000 description 277
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 238
230000002829 reductive effect Effects 0.000 description 214
239000002904 solvent Substances 0.000 description 193
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 192
238000005160 1H NMR spectroscopy Methods 0.000 description 124
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QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 87
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 85
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 84
235000019439 ethyl acetate Nutrition 0.000 description 80
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 80
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OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 73
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239000012267 brine Substances 0.000 description 70
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 70
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 66
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 56
238000005481 NMR spectroscopy Methods 0.000 description 54
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 54
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 38
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OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 36
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 36
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 28
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GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 25
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Classifications

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- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
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OA1200200192A 1999-12-23 2000-12-12 Ox(adi)azolyl-hydroxamic acids useful as procollagen C-proteinase inhibitors. OA12125A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GBGB9930570.8A GB9930570D0 (en)	1999-12-23	1999-12-23	Therapy

Publications (1)

Publication Number	Publication Date
OA12125A true OA12125A (en)	2006-05-05

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ID=10866986

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200192A OA12125A (en)	1999-12-23	2000-12-12	Ox(adi)azolyl-hydroxamic acids useful as procollagen C-proteinase inhibitors.

Country Status (32)

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EP (1)	EP1240152B1 (es)
JP (1)	JP2003519133A (es)
KR (1)	KR20020067570A (es)
CN (1)	CN1423638A (es)
AP (1)	AP2002002554A0 (es)
AR (1)	AR031085A1 (es)
AT (1)	ATE284393T1 (es)
AU (1)	AU1875601A (es)
BG (1)	BG106866A (es)
BR (1)	BR0016717A (es)
CA (1)	CA2395186C (es)
CO (1)	CO5261622A1 (es)
DE (1)	DE60016629T2 (es)
EA (1)	EA200200596A1 (es)
EE (1)	EE200200358A (es)
ES (1)	ES2231292T3 (es)
GB (1)	GB9930570D0 (es)
GT (1)	GT200000221A (es)
HU (1)	HUP0204585A3 (es)
IL (1)	IL149372A0 (es)
IS (1)	IS6363A (es)
MA (1)	MA26858A1 (es)
MX (1)	MXPA02006315A (es)
NO (1)	NO20023058L (es)
OA (1)	OA12125A (es)
PA (1)	PA8508301A1 (es)
PE (1)	PE20010951A1 (es)
PL (1)	PL357512A1 (es)
SK (1)	SK8102002A3 (es)
TN (1)	TNSN00250A1 (es)
TR (1)	TR200201642T2 (es)
WO (1)	WO2001047901A1 (es)

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GB0025310D0 (en) *	2000-10-16	2000-11-29	Pfizer Ltd	Process
US6452041B1 (en)	2000-10-16	2002-09-17	Pfizer Inc.	Olefination process to itaconate and succinate derivatives
US6716861B2 (en)	2000-12-21	2004-04-06	Pfizer, Inc.	3-ox(adi)azolylpropanohydroxamic acids useful as procollagen C-proteinase inhibitors
GB0031321D0 (en) *	2000-12-21	2001-02-07	Pfizer Ltd	Treatment
GB0108097D0 (en) *	2001-03-30	2001-05-23	Pfizer Ltd	Compounds
US6645993B2 (en)	2001-03-30	2003-11-11	Warner-Lambert Company	3-heterocyclylpropanohydroxamic acid PCP inhibitors
GB0108102D0 (en) *	2001-03-30	2001-05-23	Pfizer Ltd	Compounds
US6821972B2 (en)	2001-03-30	2004-11-23	Pfizer Inc.	3-heterocyclylpropanohydroxamic acid PCP inhibitors
GB0202254D0 (en) *	2002-01-31	2002-03-20	Pfizer Ltd	Prevention of scarring
GB0204159D0 (en) *	2002-02-22	2002-04-10	British Biotech Pharm	Metalloproteinase inhibitors
US8133903B2 (en)	2003-10-21	2012-03-13	Los Angeles Biomedical Research Institute at Harbor—UCLA Medical Center	Methods of use of inhibitors of phosphodiesterases and modulators of nitric oxide, reactive oxygen species, and metalloproteinases in the treatment of peyronie's disease, arteriosclerosis and other fibrotic diseases
WO2004096810A1 (en)	2003-04-29	2004-11-11	Pfizer Limited	5,7-diaminopyrazolo`4,3-d!pyrimidines useful in the treatment of hypertension
US7572799B2 (en)	2003-11-24	2009-08-11	Pfizer Inc	Pyrazolo[4,3-d]pyrimidines as Phosphodiesterase Inhibitors
CA2562251C (en)	2004-04-07	2009-04-28	Pfizer Inc.	Pyrazolo'4,3-d pyrimidines
WO2009097893A1 (en) *	2008-02-04	2009-08-13	Proyecto De Biomedicina Cima, S.L.	Methods for the treatment of cardiac disease associated to myocardial fibrosis using an inhibitor of pcp
TW201620887A (zh)	2014-01-10	2016-06-16	葛蘭素史克智慧財產（第二）有限公司	化合物及方法
CN108530378B (zh) *	2018-05-29	2021-09-14	济南大学	一类含有噁二唑结构的氮原子双取代异羟肟酸类化合物、用途及其制备方法
CN108721282B (zh) *	2018-07-13	2022-02-15	南京市儿童医院	Uk383367在制备用于减轻肾纤维化相关病症的药物中的应用

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WO1997031892A1 (fr) *	1996-03-01	1997-09-04	Sankyo Company, Limited	Derives d'acide hydroxamique
ID26223A (id) *	1998-03-10	2000-12-07	Smithkline Beecham Corp	Antagonis reseptor vitronektin

1999
- 1999-12-23 GB GBGB9930570.8A patent/GB9930570D0/en not_active Ceased
2000
- 2000-12-07 PA PA20008508301A patent/PA8508301A1/es unknown
- 2000-12-12 KR KR1020027008179A patent/KR20020067570A/ko not_active Application Discontinuation
- 2000-12-12 AT AT00981523T patent/ATE284393T1/de not_active IP Right Cessation
- 2000-12-12 CN CN00817410A patent/CN1423638A/zh active Pending
- 2000-12-12 AU AU18756/01A patent/AU1875601A/en not_active Abandoned
- 2000-12-12 PL PL00357512A patent/PL357512A1/xx unknown
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- 2000-12-12 EP EP00981523A patent/EP1240152B1/en not_active Expired - Lifetime
- 2000-12-12 TR TR2002/01642T patent/TR200201642T2/xx unknown
- 2000-12-12 ES ES00981523T patent/ES2231292T3/es not_active Expired - Lifetime
- 2000-12-12 IL IL14937200A patent/IL149372A0/xx unknown
- 2000-12-12 AP APAP/P/2002/002554A patent/AP2002002554A0/en unknown
- 2000-12-12 EE EEP200200358A patent/EE200200358A/xx unknown
- 2000-12-12 MX MXPA02006315A patent/MXPA02006315A/es active IP Right Grant
- 2000-12-12 OA OA1200200192A patent/OA12125A/en unknown
- 2000-12-12 BR BR0016717-7A patent/BR0016717A/pt not_active Application Discontinuation
- 2000-12-12 EA EA200200596A patent/EA200200596A1/ru unknown
- 2000-12-12 HU HU0204585A patent/HUP0204585A3/hu unknown
- 2000-12-12 SK SK810-2002A patent/SK8102002A3/sk unknown
- 2000-12-12 JP JP2001549373A patent/JP2003519133A/ja active Pending
- 2000-12-12 CA CA002395186A patent/CA2395186C/en not_active Expired - Fee Related
- 2000-12-15 CO CO00095450A patent/CO5261622A1/es unknown
- 2000-12-20 PE PE2000001370A patent/PE20010951A1/es not_active Application Discontinuation
- 2000-12-21 AR ARP000106851A patent/AR031085A1/es unknown
- 2000-12-21 GT GT200000221A patent/GT200000221A/es unknown
- 2000-12-22 TN TNTNSN00250A patent/TNSN00250A1/fr unknown
2002
- 2002-04-26 IS IS6363A patent/IS6363A/is unknown
- 2002-06-18 MA MA26694A patent/MA26858A1/fr unknown
- 2002-06-24 BG BG106866A patent/BG106866A/bg unknown
- 2002-06-24 NO NO20023058A patent/NO20023058L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO2001047901A1 (en)	2001-07-05
CO5261622A1 (es)	2003-03-31
KR20020067570A (ko)	2002-08-22
EP1240152B1 (en)	2004-12-08
EP1240152A1 (en)	2002-09-18
NO20023058L (no)	2002-08-23
AU1875601A (en)	2001-07-09
DE60016629T2 (de)	2005-12-08
EE200200358A (et)	2003-10-15
HUP0204585A2 (hu)	2003-04-28
ES2231292T3 (es)	2005-05-16
BR0016717A (pt)	2002-09-03
CN1423638A (zh)	2003-06-11
AP2002002554A0 (en)	2002-06-30
PA8508301A1 (es)	2002-08-26
NO20023058D0 (no)	2002-06-24
MA26858A1 (fr)	2004-12-20
DE60016629D1 (de)	2005-01-13
IS6363A (is)	2002-04-26
MXPA02006315A (es)	2002-11-29
PL357512A1 (en)	2004-07-26
JP2003519133A (ja)	2003-06-17
BG106866A (bg)	2003-03-31
SK8102002A3 (en)	2003-09-11
AR031085A1 (es)	2003-09-10
ATE284393T1 (de)	2004-12-15
IL149372A0 (en)	2002-11-10
TR200201642T2 (tr)	2002-11-21
PE20010951A1 (es)	2001-09-24
GB9930570D0 (en)	2000-02-16
CA2395186C (en)	2006-03-28
EA200200596A1 (ru)	2002-12-26
HUP0204585A3 (en)	2006-01-30
GT200000221A (es)	2002-06-14
CA2395186A1 (en)	2001-07-05
TNSN00250A1 (fr)	2002-05-30

Publication	Publication Date	Title
OA12125A (en)	2006-05-05	Ox(adi)azolyl-hydroxamic acids useful as procollagen C-proteinase inhibitors.
AU760181B2 (en)	2003-05-08	Aminobutanoic acid derivatives
US5300501A (en)	1994-04-05	Peptidyl derivatives
US5569665A (en)	1996-10-29	Peptidyl derivatives and their use as metalloproteinases inhibitors
US5571792A (en)	1996-11-05	Histidine and homohistidine derivatives as inhibitors of protein farnesyltransferase
US5618844A (en)	1997-04-08	Hydroxamic acid and carboxylic acid derivatives, process for their preparation and use thereof
JP2571230B2 (ja)	1997-01-16	５−アミノ−４−ヒドロキシ吉草酸誘導体の製造方法
US6235717B1 (en)	2001-05-22	Pharmaceutical compounds
JPH06122665A (ja)	1994-05-06	フィブリノーゲン受容体拮抗薬
JPH04211095A (ja)	1992-08-03	新規ジペプチド、その製造方法及び薬剤におけるレニン阻害剤としてのその使用
EP1373264B1 (en)	2004-12-22	3-heterocyclylpropanohydroxamic acid as procollagen c-proteinase inhibitors
WO1996023791A1 (en)	1996-08-08	Bridged indoles as matrix metalloprotease inhibitors
US8957205B2 (en)	2015-02-17	Cycloalkane carboxamide derivatives and production process of same
US6448278B2 (en)	2002-09-10	Procollagen C-proteinase inhibitors
US5773428A (en)	1998-06-30	Matrix metalloprotease inhibitors
CA2432643C (en)	2007-07-17	3-ox(adi)azolylpropanohydroxamic acids useful as procollagen c-proteinase inhibitors
EP1373231B1 (en)	2005-06-08	3-heterocyclyl-propano-hydroxamic acid as pcp inhibitors
US6831088B2 (en)	2004-12-14	3-heterocyclypropanohydroxamic acid PCP inhibitors
JPH0925293A (ja)	1997-01-28	ヒスチジル−ヒドロキサム酸誘導体
MX2008008997A (es)	2008-09-26	Derivado de cicloalcancarboxamida y metodo para producir el mismo
JPH0395168A (ja)	1991-04-19	ジペプチド化合物