SI20876B - Derivati propanojske kisline, ki inhibirajo vezavo integrinov na njihove receptorje - Google Patents
Derivati propanojske kisline, ki inhibirajo vezavo integrinov na njihove receptorje Download PDFInfo
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- SI20876B SI20876B SI200020020A SI200020020A SI20876B SI 20876 B SI20876 B SI 20876B SI 200020020 A SI200020020 A SI 200020020A SI 200020020 A SI200020020 A SI 200020020A SI 20876 B SI20876 B SI 20876B
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- c3alkyl
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims 5
- 102000005962 receptors Human genes 0.000 title abstract 2
- 108020003175 receptors Proteins 0.000 title abstract 2
- 102000006495 integrins Human genes 0.000 title 1
- 108010044426 integrins Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 230000005764 inhibitory process Effects 0.000 claims abstract 2
- -1 aliphatic acyl Chemical group 0.000 claims 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 4
- 235000019260 propionic acid Nutrition 0.000 claims 4
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 3
- 125000006323 alkenyl amino group Chemical group 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 3
- 125000006319 alkynyl amino group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000003435 aroyl group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000001769 aryl amino group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000005841 biaryl group Chemical group 0.000 claims 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 3
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000004986 diarylamino group Chemical group 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000005309 thioalkoxy group Chemical group 0.000 claims 3
- 125000005000 thioaryl group Chemical group 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229910018828 PO3H2 Inorganic materials 0.000 claims 1
- 150000007854 aminals Chemical class 0.000 claims 1
- 125000004367 cycloalkylaryl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 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 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 abstract 2
- 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 102000016359 Fibronectins Human genes 0.000 abstract 1
- 108010067306 Fibronectins Proteins 0.000 abstract 1
- 102000012355 Integrin beta1 Human genes 0.000 abstract 1
- 108010022222 Integrin beta1 Proteins 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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Abstract
Postopek za inhibicijo vezave alfa4beta1-integrina na njegove receptorje, npr. VCAM-1 (vaskularna celična adhezijska molekula-1) in fibronektin; spojine, ki inhibirajo to vezavo; farmacevtsko aktivni sestavki, ki obsegajo take spojine; in uporaba takih spojin, kot so bodisi zgoraj ali v formulacijah, za kontrolo ali preprečevanje bolezenskih stanj, v katere je vključen alfa4beta1.
Claims (8)
1 PATENTNI ZAHTEVKI 1. Spojina s strukturo:
kjer je obroč, ki vključuje Y, monociklični heterocikel, ki sestoji iz po izbiri substituiranega oksopiridinila s formulo IV:
IV q je celo število od 0 do 4 T je izbran iz skupine, ki jo sestavlja -(CH2)b, kjer je b celo število od 0 do 3 L je izbran iz skupine, ki jo sestavljajo -O-, -NR -, -S- in -(CH2)n, kjer je n celo število 0 ali 1, in B, R*, R4, R6, R9, R^9, R1 1 in R13 so neodvisno izbrani iz skupine, ki jo sestavljajo vodik, halogen, hidroksil, alkil, alkenil, alkinil, alkoksi, alkenoksi, alkinoksi, tioalkoksi, hidroksialkil, alifatski acil, -CF3, nitro, amino, ciano, karboksi, 2 -N(C1-C3alkil)-C(0)(CrC3alkil), -NHC(0)NH(C,-C3alkil), -NHC(0)N(C,-C3alkil)C(0)-NH(Ci-C3alkil), -Ci-C3alkilamino, alkenilamino, alkinilamino, di(C!-C3alkil)amino, -C(0)0-(CrC3)alkil, -C(0)NH-(Ci-C3)alkil, -CH=NOH, -P03H2, -0P03H2, -C(0)N(CrC3alkil)2, haloalkil, alkoksialkoksi, karboksaldehid, karboksamid, cikloalkil, cikloalkenil, cikloalkinil, cikloalkilalkil, aril, aroil, ariloksi, arilamino, biaril, tioaril, diarilamino, heterociklil, alkilaril, aralkenil, aralkil, alkilheterociklil, heterociklilalkil, sulfonil, -S02-(Ci-C3alkil), -S03-(Ci-C3alkil), sulfonamido, ariloksialkil, karboksil, karbamat in -C(0)NH(benzil), R8 je neodvisno izbran iz skupine, ki jo sestavljajo halogen, hidroksil, alkil, alkenil, alkinil, alkoksi, alkenoksi, alkinoksi, tioalkoksi, hidroksialkil, alifatski acil, -CF3, nitro, amino, ciano, karboksi, -N(C1-C3alkil)-C(0)(C1-C3alkil), -NHC(0)NH(CrC3alkil), -NHC(0)N(C i -C3alkil)C(0)-NH(C i -C3alkil), -C i -C3alkilamino, alkenilamino, alkinilamino, di(Ci-C3alkil)amino, -C(0)0-(Ci-C3alkil), -C(0)NH-(Ci- C3)alkil, -CH=NOH, -P03H2, -0P03H2, -C(0)N(Ci-C3alkil)2, haloalkil, alkoksialkoksi, karboksaldehid, karboksamid, cikloalkil, cikloalkenil, cikloalkinil, cikloalkilalkil, aril, aroil, ariloksi, arilamino, biaril, tioaril, diarilamino, heterociklil, alkilaril, aralkenil, aralkil, alkilheterociklil, heterociklilalkil, sulfonil, -S02-(Ci-C3alkil), -S03-(Ci-C3alkil), sulfonamido, ariloksialkil, karboksil, karbamat in -C(0)NH(benzil), kjer, kadar je L -NR13-, lahko R4 in R13, vzeta skupaj, tvorita obroč in kjer R6 in R8, vzeta skupaj, lahko tvorita obroč in kjer R9 in R10, vzeta skupaj, lahko tvorita obroč, ali njena farmacevtsko sprejemljiva sol.
2. Spojina po zahtevku 1, ki je derivat le-te, izbran izmed estrov, karbamatov in aminalov.
3. Spojina s strukturo: 3
kjer je krog Q obroč, ki sestoji iz:
kjer je q celo število od nič do 4 in so B, R1, R6, R8, R9, R10 in R11 vsak neodvisno izbrani iz skupine, ki jo sestavljajo vodik, halogen, hidroksil, alkil, alkenil, alkinil, alkoksi, alkenoksi, alkinoksi, tioalkoksi, hidroksialkil, alifatski acil, -CF3, nitro, amino, ciano, karboksi, -N(Ci-C3alkil)-C(0)(Ci-C3alkil), -NHC(0)NH(Ci-C3alkil), -NHC(0)N(Ci-C3alkil)C(0)-NH(CrC3alkil), -CrC3alkilamino, alkenilamino, alkinilamino, di(C1-C3alkil)amino, -C(0)0-(Ci-C3alkil), -C(0)NH-(Ci- C3)alkil, -CH=NOH, -P03H2, -0P03H2, -C(0)N(CrC3alkil)2, haloalkil, alkoksialkoksi, karboksaldehid, karboksamid, cikloalkil, cikloalkenil, cikloalkinil, cikloalkilalkil, aril, aroil, ariloksi, arilamino, biaril, tioaril, diarilamino, heterociklil, alkilaril, aralkenil, aralkil, alkilheterociklil, heterociklilalkil, sulfonil, -S02-(CrC3alkil), -S03-(Ci-C3alkil), sulfonamido, ariloksialkil, karboksil, karbamat in -C(0)NH(benzil), kjer R in R , vzeta skupaj, lahko tvorita obroč 4 in kjer R1 in R2, vzeta skupaj, lahko tvorita obroč, ali njena farmacevtsko sprejemljiva sol.
4. Spojina po zahtevku 3, ki je derivat le-te, izbran izmed estrov, karbamatov in aminalov.
5. Spojina po zahtevku 3, kjer so R6, R8, R1, R2 in R11 vsak neodvisno izbrani iz skupine, ki jo sestavljata vodik in alkil, in je R1 pri vsakem pojavljanju neodvisno izbran iz skupine, ki jo sestavljajo vodik, 2-tienilmetil, benzil in metil.
6. Spojina, izbrana iz skupine, ki jo sestavljajo (3S)-3-(l,3-benzodioksol-5-il)-3-((2R,S)-2-(3 -benzil- 5 -metil-2-okso-1 (2H)-piridinil)heksanoilamino)propanoj ska kislina, (3S)-3-( 1,3-benzodioksol-5-il)-3-((2R,S)-2-(3-(3-klorobenzil)-5-metil-2-okso-l(2H)-piridinil)heksanoilamino)propanojska kislina, (3S)-3-(l,3-benzodioksol-5-il)-3-(((2S)-2-(2-okso-3-(fenilmetil)-l-(2H)-piridinil)heksanoil)amino)propanojska kislina, (3S)-3-(l,3-benzodioksol-5-il)-3-((2-(3-klorofenil)metil)-5-metil-2-okso-l(2H)-piridinil)heksanoil)amino)propanojska kislina in njihove farmacevtsko sprejemljive soli.
7. Spojina po zahtevku 6, ki je derivat le-te, izbran iz skupine, ki jo sestavljajo estri, karbamati in aminali.
8. Farmacevtski sestavek, ki obsega spojino po zahtevku 1 v farmacevtsko sprejemljivem nosilcu. 1 Uporaba spojine po zahtevku 1 za pripravo zdravila za selektivno inhibiranje 2 vezave a4Pi-integrina pri sesalcu.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13296799P | 1999-05-07 | 1999-05-07 | |
| US17044199P | 1999-12-10 | 1999-12-10 | |
| PCT/US2000/012464 WO2000068188A1 (en) | 1999-05-07 | 2000-05-05 | Propanoic acid derivatives that inhibit the binding of integrins to their receptors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI20876A SI20876A (sl) | 2002-10-31 |
| SI20876B true SI20876B (sl) | 2009-08-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200020020A SI20876B (sl) | 1999-05-07 | 2000-05-05 | Derivati propanojske kisline, ki inhibirajo vezavo integrinov na njihove receptorje |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP1189881B2 (sl) |
| JP (2) | JP4841729B2 (sl) |
| KR (1) | KR100767199B1 (sl) |
| CN (1) | CN100360499C (sl) |
| AT (1) | ATE277923T1 (sl) |
| AU (1) | AU4826900A (sl) |
| BR (1) | BR0010349B1 (sl) |
| CA (1) | CA2373180C (sl) |
| CZ (1) | CZ304225B6 (sl) |
| DE (1) | DE60014369T3 (sl) |
| ES (1) | ES2228527T5 (sl) |
| HK (1) | HK1044533A1 (sl) |
| HU (1) | HU229155B1 (sl) |
| IL (2) | IL146312A0 (sl) |
| MX (1) | MXPA01011341A (sl) |
| NO (1) | NO329899B1 (sl) |
| NZ (1) | NZ515249A (sl) |
| RO (1) | RO121640B1 (sl) |
| RU (1) | RU2255933C9 (sl) |
| SI (1) | SI20876B (sl) |
| SK (1) | SK288186B6 (sl) |
| TR (1) | TR200103427T2 (sl) |
| WO (1) | WO2000068188A1 (sl) |
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| US6972296B2 (en) | 1999-05-07 | 2005-12-06 | Encysive Pharmaceuticals Inc. | Carboxylic acid derivatives that inhibit the binding of integrins to their receptors |
| US6723711B2 (en) * | 1999-05-07 | 2004-04-20 | Texas Biotechnology Corporation | Propanoic acid derivatives that inhibit the binding of integrins to their receptors |
| AR026748A1 (es) | 1999-12-08 | 2003-02-26 | Vertex Pharma | Un compuesto inhibidor de caspasas, una composicion farmaceutica que lo comprende, un metodo para la sintesis del mismo y un compuesto intermediario paradicha sintesis |
| PE20020420A1 (es) | 2000-10-02 | 2002-06-27 | Novartis Ag | Derivados de diazacicloalcanodiona como antagonistas del antigeno asociado a la funcion del linfocito-1 (lfa-1) |
| FR2834212B1 (fr) * | 2001-12-27 | 2004-07-09 | Besins Int Belgique | Utilisation d'une poudre a liberation immediate dans des compositions pharmaceutiques et nutraceutiques |
| JP4616643B2 (ja) | 2002-06-28 | 2011-01-19 | バーテックス ファーマシューティカルズ インコーポレイテッド | カスパーゼインヒビターおよびそれらの用途 |
| CN1703395A (zh) | 2002-08-09 | 2005-11-30 | 特兰斯泰克制药公司 | 芳基和杂芳基化合物以及调节凝血的方法 |
| EP1581501A1 (en) | 2002-12-20 | 2005-10-05 | Vertex Pharmaceuticals Incorporated | 4-oxo-3-(1-oxo-1h-isoquinolin-2-ylacetylamino)-pentanoic acid ester and amide derivatives and their use as caspase inhibitors |
| PE20050159A1 (es) | 2003-05-27 | 2005-04-19 | Vertex Pharma | Derivados de acido 3-[2-(3-amino-2-oxo-2h-piridin-1-il)-acetilamino]-4-oxo-pentanoico como inhibidores de caspasa |
| US7208601B2 (en) | 2003-08-08 | 2007-04-24 | Mjalli Adnan M M | Aryl and heteroaryl compounds, compositions, and methods of use |
| US7501538B2 (en) | 2003-08-08 | 2009-03-10 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| CA2531796A1 (en) | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions, and methods of use |
| US8003806B2 (en) | 2004-11-12 | 2011-08-23 | OSI Pharmaceuticals, LLC | Integrin antagonists useful as anticancer agents |
| RS53599B1 (sr) | 2005-05-10 | 2015-02-27 | Intermune, Inc. | Piridon derivati za modulaciju stresom aktiviranog sistema proteinskih kinaza |
| JP5181118B2 (ja) | 2005-07-11 | 2013-04-10 | ワイス・エルエルシー | グルタミン酸アグリカナーゼ阻害剤 |
| KR20080058436A (ko) | 2005-10-13 | 2008-06-25 | 와이어쓰 | 글루탐산 유도체의 제조 방법 |
| JP5627574B2 (ja) | 2008-06-03 | 2014-11-19 | インターミューン, インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| CN106459042B (zh) | 2014-04-02 | 2019-06-28 | 英特穆恩公司 | 抗纤维化吡啶酮类 |
| US10875875B2 (en) * | 2017-04-26 | 2020-12-29 | Aviara Pharmaceuticals, Inc. | Propionic acid derivatives and methods of use thereof |
| EP3773573B1 (en) * | 2018-04-12 | 2026-03-18 | Morphic Therapeutic, Inc. | Antagonists of human integrin (alpha4)(beta7) |
| JP7437490B2 (ja) * | 2019-10-16 | 2024-02-22 | モーフィック セラピューティック,インコーポレイテッド | ヒトインテグリン(アルファ-4)(ベータ-7)の阻害 |
| WO2023134698A1 (zh) * | 2022-01-11 | 2023-07-20 | 深圳信立泰药业股份有限公司 | 一种哒嗪-1(6h)-6-氧代类化合物及其制备方法与应用 |
| TW202448457A (zh) * | 2023-05-17 | 2024-12-16 | 大陸商西藏海思科製藥有限公司 | 羧基衍生物及其在醫藥上的應用 |
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| US5874424A (en) * | 1995-12-20 | 1999-02-23 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β converting enzyme |
| GR851819B (sl) * | 1984-08-17 | 1985-11-26 | Wyeth John & Brother Ltd | |
| FI934894L (fi) * | 1991-05-07 | 1993-11-05 | Merck & Co Inc | Fibrinogenreceptorantagonister |
| US5847135A (en) * | 1994-06-17 | 1998-12-08 | Vertex Pharmaceuticals, Incorporated | Inhibitors of interleukin-1β converting enzyme |
| EP0761680A3 (en) * | 1995-09-12 | 1999-05-06 | Ono Pharmaceutical Co., Ltd. | Tetrazole compounds having Interleukin-1beta converting enzyme inhibitory activity |
| SG124234A1 (en) * | 1996-07-25 | 2006-08-30 | Biogen Idec Inc | Cell adhesion inhibitors |
| JP2002511052A (ja) * | 1996-08-29 | 2002-04-09 | メルク エンド カンパニー インコーポレーテッド | インテグリンアンタゴニスト |
| BR9712530A (pt) * | 1996-10-11 | 1999-10-19 | Warner Lambert Co | Inibidores de ésteres de asparato de enzima de conversão de interleucina-1beta |
| DE19647380A1 (de) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | 5-Ring-Heterocyclen als Inhibitoren der Leukozytenadhäsion und VLA-4-Antagonisten |
| AR016751A1 (es) * | 1996-11-22 | 2001-08-01 | Athena Neurosciences Inc | Metodo para inhibir la liberacion del peptido beta-amiloide en una celula, composicion farmaceutica y compuestos utiles en dicho metodo |
| PL336589A1 (en) * | 1997-05-02 | 2000-07-03 | Akzo Nobel Nv | Serinic protease inhibitors |
| DE19741235A1 (de) * | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| US6331640B1 (en) * | 1998-10-13 | 2001-12-18 | Hoffmann-La Roche Inc. | Diaminopropionic acid derivatives |
| WO2000061631A1 (en) * | 1999-04-12 | 2000-10-19 | Astrazeneca Ab | Modified pentapeptide antagonists of the atrial natriuretic peptide clearance receptor |
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2000
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- 2000-05-05 WO PCT/US2000/012464 patent/WO2000068188A1/en not_active Ceased
- 2000-05-05 RO ROA200101209A patent/RO121640B1/ro unknown
- 2000-05-05 KR KR1020017014179A patent/KR100767199B1/ko not_active Expired - Fee Related
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- 2000-05-05 BR BRPI0010349-7A patent/BR0010349B1/pt not_active IP Right Cessation
- 2000-05-05 HK HK02106258.2A patent/HK1044533A1/zh unknown
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- 2000-05-05 RU RU2001133341/04A patent/RU2255933C9/ru not_active IP Right Cessation
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- 2000-05-05 SI SI200020020A patent/SI20876B/sl not_active IP Right Cessation
- 2000-05-05 DE DE60014369T patent/DE60014369T3/de not_active Expired - Lifetime
- 2000-05-05 TR TR2001/03427T patent/TR200103427T2/xx unknown
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