HUP0402263A2 - Acetilénkötést tartalmazó alfa-aminosav-alapú szulfonamid-hidroxámsav TACE-gátlók, eljárás előállításukra és az ezeket tartalmazó gyógyszerkészítmények - Google Patents
Acetilénkötést tartalmazó alfa-aminosav-alapú szulfonamid-hidroxámsav TACE-gátlók, eljárás előállításukra és az ezeket tartalmazó gyógyszerkészítményekInfo
- Publication number
- HUP0402263A2 HUP0402263A2 HU0402263A HUP0402263A HUP0402263A2 HU P0402263 A2 HUP0402263 A2 HU P0402263A2 HU 0402263 A HU0402263 A HU 0402263A HU P0402263 A HUP0402263 A HU P0402263A HU P0402263 A2 HUP0402263 A2 HU P0402263A2
- Authority
- HU
- Hungary
- Prior art keywords
- aryl
- alkyl
- heteroaryl
- cycloalkyl
- hydrogen
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 title 1
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 title 1
- 235000008206 alpha-amino acids Nutrition 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229940124530 sulfonamide Drugs 0.000 title 1
- 150000003456 sulfonamides Chemical class 0.000 title 1
- 239000002447 tumor necrosis factor alpha converting enzyme inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 10
- 125000003118 aryl group Chemical group 0.000 abstract 10
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 9
- 125000001072 heteroaryl group Chemical group 0.000 abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 8
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004475 heteroaralkyl group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract 1
- 102100040247 Tumor necrosis factor Human genes 0.000 abstract 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
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- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
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- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
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- 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
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- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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Abstract
A találmány a TNF-a-t konvertáló enzimet gátló hatású (B) általánosképletű vegyületekre, a képletben X jelentése -SO2- vagy -P(O)-R10-általános képletű csoport; Y jelentése aril- vagy heteroarilcsoport; Zjelentése oxigén- vagy kénatom, -NH- vagy -CH2- csoport, R1 jelentésehidrogénatom, aril-, alkil-, alkenil- vagy alkinilcsoport; R2jelentése hidrogénatom, aril-, aralkil-, heteroaril-, heteroaralkil-,cikloalkil-, heterocikloalkil-, alkil-, alkenil- vagy alkinilcsoport;vagy R1 és R2 együtt azzal az atommal, amelyhez kapcsolódnak, gyűrűtképezhet; R3 jelentése hidrogénatom, alkil-, cikloalkil-,heterocikloalkil-, aralkil- vagy heteroaralkilcsoport; vagy R1 és R3azokkal az atomokkal, amelyekhez kapcsolódnak, 5-8 tagú gyűrűtképezhet, amely aril- vagy heteroarilcsoporttal lehet kondenzálva; R4és R5 jelentése hidrogénatom vagy alkil-, ciano- vagy -CCH csoport; R6jelentése hidrogénatom, aril-, heteroaril-, alkil-, alkenil-,alkinil-, cikloalkil- vagy heterocikloalkilcsoport; R8 és R9 jelentésehidrogénatom, alkil-, alkenil-, alkinil-, cikloalkil-, aril-,aralkil-, heteroaril-, heteroaralkil vagy heterocikloalkilcsoport; R10jelentése alkil-, cikloalkil-, aril- vagy heteroarilcsoport; R11jelentése hidrogénatom, alkil-, cikloalkil-, aril-, heteroaril-, -S(O)nR8, -COOR8, -CONR8R9, -SO2NR8R9 vagy -COR8 általános képletűcsoport; R12 és R13 jelentése hidrogénatom, -OR8, -NR8R9, alkil-,alkenil-, alkinil-, cikloalkil-, aril-, heteroaril-, -COOR8 vagy -CONR8R9 általános képletű csoport; vagy Rl2 és R13 együtt cikloalkil-vagy heterocikloalkilgyűrűt alkot; vagy Rl2 és R13 együtt aszénatommal, amelyhez kapcsolódnak, karbonilcsoportot alkot; R14jelentése hidrogénatom, aril-, heteroaril-, alkil- vagycikloalkilcsoport; és n értéke 0, 1 vagy 2; és a vegyületekettartalmazó gyógyászati készítményekre vonatkozik. A találmány tárgyatovábbá eljárás a vegyületek előállítására, valamint az (II) és (III)általános képletű intermedierek, a képletekben R4, R5 és R6 a fentebbmeghatározottak azzal az eltéréssel, hogy R6 jelentése hidrogénatomtóleltérő, J jelentése fluor-, bróm- vagy klóratom, 1,2,4-triazolil-,benzotriazolil- vagy imidazolilcsoport. Ó
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US23825599A | 1999-01-27 | 1999-01-27 | |
PCT/US2000/001981 WO2000044709A2 (en) | 1999-01-27 | 2000-01-27 | ACETYLENIC α-AMINO ACID-BASED SULFONAMIDE HYDROXAMIC ACID TACE INHIBITORS |
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US6777217B1 (en) | 1996-03-26 | 2004-08-17 | President And Fellows Of Harvard College | Histone deacetylases, and uses related thereto |
US6946473B2 (en) | 1999-01-27 | 2005-09-20 | Wyeth Holdings Corporation | Preparation and use of acetylenic ortho-sulfonamido and phosphinic acid amido bicyclic heteroaryl hydroxamic acids as TACE inhibitors |
GB9918684D0 (en) * | 1999-08-09 | 1999-10-13 | Novartis Ag | Organic compounds |
US20030129724A1 (en) | 2000-03-03 | 2003-07-10 | Grozinger Christina M. | Class II human histone deacetylases, and uses related thereto |
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GB0103303D0 (en) | 2001-02-09 | 2001-03-28 | Novartis Ag | Organic compounds |
CA2357110A1 (en) * | 2001-04-11 | 2002-10-11 | American Cyanamid Company | Method for the treatment of polycystic kidney disease |
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FR2950056B1 (fr) | 2009-09-17 | 2011-08-26 | Galderma Res & Dev | Nouveaux composes benzene-carboxylamides, leur procede de synthese et leur utilisation en medecine ainsi qu'en cosmetique |
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CA2218503C (en) * | 1995-04-20 | 2001-07-24 | Pfizer Inc. | Arylsulfonyl hydroxamic acid derivatives |
JP3539736B2 (ja) * | 1996-08-28 | 2004-07-07 | ザ プロクター アンド ギャンブル カンパニー | 基質メタロプロテアーゼインヒビターとしてのホスフィン酸アミド |
CA2263932A1 (en) * | 1996-08-28 | 1998-03-05 | Yetunde Olabisi Taiwo | 1,4-heterocyclic metalloprotease inhibitors |
RU2221782C2 (ru) * | 1996-08-28 | 2004-01-20 | Дзе Проктер Энд Гэмбл Компани | Замещенные циклические аминовые ингибиторы металлопротеаз |
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