CA2072785C - Pharmacologically active hydrazine derivatives and processes for the preparation thereof - Google Patents

Pharmacologically active hydrazine derivatives and processes for the preparation thereof Download PDF

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Publication number
CA2072785C
CA2072785C CA002072785A CA2072785A CA2072785C CA 2072785 C CA2072785 C CA 2072785C CA 002072785 A CA002072785 A CA 002072785A CA 2072785 A CA2072785 A CA 2072785A CA 2072785 C CA2072785 C CA 2072785C
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CA
Canada
Prior art keywords
lower alkyl
substituted
alkyl
phenyl
hydroxy
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
CA002072785A
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English (en)
French (fr)
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CA2072785A1 (en
Inventor
Alexander Faessler
Guido Bold
Marc Lang
Peter Schneider
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Novartis AG
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Novartis AG
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Publication of CA2072785A1 publication Critical patent/CA2072785A1/en
Application granted granted Critical
Publication of CA2072785C publication Critical patent/CA2072785C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/24—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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
    • A61K31/175—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine having the group, >N—C(O)—N=N— or, e.g. carbonohydrazides, carbazones, semicarbazides, semicarbazones; Thioanalogues thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
    • C07C243/14—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/10—Hydrazines
    • C07C243/12—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms
    • C07C243/16—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • C07C243/18—Hydrazines having nitrogen atoms of hydrazine groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/02—Compounds containing any of the groups, e.g. carbazates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C281/02—Compounds containing any of the groups, e.g. carbazates
    • C07C281/04—Compounds containing any of the groups, e.g. carbazates the other nitrogen atom being further doubly-bound to a carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/24—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
    • C07D213/54—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
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oncology (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • AIDS & HIV (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Quinoline Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)
CA002072785A 1991-07-03 1992-06-30 Pharmacologically active hydrazine derivatives and processes for the preparation thereof Expired - Lifetime CA2072785C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1962/91-0 1991-07-03
CH196291 1991-07-03

Publications (2)

Publication Number Publication Date
CA2072785A1 CA2072785A1 (en) 1993-01-04
CA2072785C true CA2072785C (en) 2006-07-25

Family

ID=4222677

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002072785A Expired - Lifetime CA2072785C (en) 1991-07-03 1992-06-30 Pharmacologically active hydrazine derivatives and processes for the preparation thereof

Country Status (27)

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EP (1) EP0521827B1 (enrdf_load_html_response)
JP (1) JP3187535B2 (enrdf_load_html_response)
KR (1) KR100255099B1 (enrdf_load_html_response)
CN (1) CN1054598C (enrdf_load_html_response)
AT (1) ATE143355T1 (enrdf_load_html_response)
AU (1) AU660469B2 (enrdf_load_html_response)
CA (1) CA2072785C (enrdf_load_html_response)
CZ (1) CZ280651B6 (enrdf_load_html_response)
DE (1) DE59207226D1 (enrdf_load_html_response)
DK (1) DK0521827T3 (enrdf_load_html_response)
DZ (1) DZ1591A1 (enrdf_load_html_response)
ES (1) ES2093237T3 (enrdf_load_html_response)
FI (1) FI114634B (enrdf_load_html_response)
GR (1) GR3021169T3 (enrdf_load_html_response)
HU (1) HU219915B (enrdf_load_html_response)
IE (1) IE80471B1 (enrdf_load_html_response)
IL (1) IL102354A (enrdf_load_html_response)
MA (1) MA22581A1 (enrdf_load_html_response)
MX (1) MX9203899A (enrdf_load_html_response)
NO (1) NO178541C (enrdf_load_html_response)
NZ (1) NZ243410A (enrdf_load_html_response)
PL (1) PL171232B1 (enrdf_load_html_response)
RU (1) RU2092492C1 (enrdf_load_html_response)
SA (1) SA93140336B1 (enrdf_load_html_response)
SK (1) SK279706B6 (enrdf_load_html_response)
TW (1) TW309512B (enrdf_load_html_response)
ZA (1) ZA924914B (enrdf_load_html_response)

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US5753652A (en) * 1991-07-03 1998-05-19 Novartis Corporation Antiretroviral hydrazine derivatives
BR9306058A (pt) * 1992-03-11 1997-11-18 Narhex Ltd Derivados de amina de hidrocarbonetos oxo- e hidroxi- substituidos
DE69333270T2 (de) 1992-03-11 2004-08-05 Narhex Ltd. Aminderivate von oxo- und hydroxy- substituierten kohlenwasserstoffen
US5888992A (en) 1992-03-11 1999-03-30 Narhex Limited Polar substituted hydrocarbons
US6071895A (en) 1992-03-11 2000-06-06 Narhex Limited Polar-substituted hydrocarbons
AU681342B2 (en) * 1992-03-11 1997-08-28 Narhex Limited Amine derivatives of oxo- and hydroxy-substitued hydrocarbons
US5559256A (en) * 1992-07-20 1996-09-24 E. R. Squibb & Sons, Inc. Aminediol protease inhibitors
ATE143004T1 (de) * 1992-12-23 1996-10-15 Ciba Geigy Ag Antiretrovirale hydrazinderivate
US5461067A (en) * 1993-02-25 1995-10-24 Abbott Laboratories Retroviral protease inhibiting compounds
EP0626178A1 (de) * 1993-05-17 1994-11-30 Ciba-Geigy Ag Verwendung von Hemmstoffen von HIV-Aspartatproteasen zur Bekämpfung von Tumorerkrankungen
IL110898A0 (en) * 1993-09-10 1994-11-28 Narhex Australia Pty Ltd Polar-substituted hydrocarbons
AU3150395A (en) * 1994-08-09 1996-03-07 Abbott Laboratories Retroviral protease inhibiting 1,2,4-triazacycloheptanes
US6225345B1 (en) 1995-11-21 2001-05-01 Novartis Ag Azahexane derivatives as substrate isosters of retroviral asparate proteases
TW409125B (en) * 1996-04-22 2000-10-21 Novartis Ag Antivirally active heterocyclic azahexane derivatives
US5849911A (en) * 1996-04-22 1998-12-15 Novartis Finance Corporation Antivirally active heterocyclic azahexane derivatives
EP0912547B1 (de) * 1996-05-10 2005-10-12 Bayer CropScience AG Neue substituierte pyridylketoenole
AU2959397A (en) * 1996-05-31 1998-01-05 Novartis Ag Process for the preparation of hydrazine derivatives useful as intermediates for the preparation of peptide analogues
US6642261B2 (en) * 1997-11-21 2003-11-04 Athena Neurosciences, Inc. N-(aryl/heteroarylacety) amino acid esters, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
ATE302751T1 (de) * 2000-06-30 2005-09-15 Elan Pharm Inc Verbindungen zur behandlung der alzheimerischen krankheit
RU2203057C1 (ru) * 2002-05-22 2003-04-27 Нестерук Владимир Викторович Способ получения таблеток оксациллина натриевой соли
NZ573888A (en) * 2006-07-21 2012-02-24 Gilead Sciences Inc Aza-peptide protease inhibitors
EP2069303B1 (en) 2006-07-21 2016-03-30 Gilead Sciences, Inc. Antiviral protease inhibitors
JOP20180009A1 (ar) 2017-02-06 2019-01-30 Gilead Sciences Inc مركبات مثبط فيروس hiv
TWI829205B (zh) 2018-07-30 2024-01-11 美商基利科學股份有限公司 抗hiv化合物
CN115197118B (zh) * 2022-06-21 2024-01-23 贵州医科大学 一种3,3双取代硫化氧化吲哚衍生物的合成方法
CN116988204A (zh) * 2023-07-13 2023-11-03 博森纺织科技股份有限公司 一种防臭抑菌面料及其生产工艺

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BE635585A (enrdf_load_html_response) * 1962-07-30
AR206201A1 (es) 1972-06-29 1976-07-07 Ciba Geigy Ag Procedimiento para la obtencion de compuestos de acido 7beta-amino-3-cefem-3-01-4-carboxilico0-substituidos
US5142056A (en) 1989-05-23 1992-08-25 Abbott Laboratories Retroviral protease inhibiting compounds
US4794109A (en) 1982-11-16 1988-12-27 Ciba-Geigy Corporation 6-hydroxy-lower alkylpenem compounds, pharmaceutical preparations that contain these compounds, and the use of the latter
EP0236734A3 (de) 1986-02-07 1988-05-11 Ciba-Geigy Ag Durch schwefelhaltigen Gruppen substituierte 5-Amino-4-hydroxyvalerylderivate
EP0376040A3 (en) 1988-12-27 1990-09-12 American Cyanamid Company N-phosphinyl di-and tripeptides as renin inhibitors

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FI923017A7 (fi) 1993-01-04
DK0521827T3 (da) 1996-11-11
TW309512B (enrdf_load_html_response) 1997-07-01
RU2092492C1 (ru) 1997-10-10
CZ280651B6 (cs) 1996-03-13
KR930002372A (ko) 1993-02-23
ATE143355T1 (de) 1996-10-15
IL102354A (en) 1997-01-10
MX9203899A (es) 1993-01-01
FI114634B (fi) 2004-11-30
NO178541B (no) 1996-01-08
MA22581A1 (fr) 1993-04-01
SK206292A3 (en) 1995-02-08
NZ243410A (en) 1995-02-24
ZA924914B (en) 1993-03-31
CA2072785A1 (en) 1993-01-04
DZ1591A1 (fr) 2002-02-17
IE922166A1 (en) 1993-01-13
CZ206292A3 (en) 1993-11-17
EP0521827A1 (de) 1993-01-07
IE80471B1 (en) 1998-07-29
ES2093237T3 (es) 1996-12-16
HU219915B (hu) 2001-09-28
GR3021169T3 (en) 1996-12-31
KR100255099B1 (ko) 2000-05-01
SA93140336B1 (ar) 2006-08-14
IL102354A0 (en) 1993-01-14
NO922611L (no) 1993-01-04
CN1068333A (zh) 1993-01-27
PL171232B1 (pl) 1997-03-28
HU9202215D0 (en) 1992-10-28
NO178541C (no) 1996-04-17
AU660469B2 (en) 1995-06-29
DE59207226D1 (de) 1996-10-31
JP3187535B2 (ja) 2001-07-11
PL295100A1 (en) 1993-03-22
EP0521827B1 (de) 1996-09-25
FI923017A0 (fi) 1992-06-29
CN1054598C (zh) 2000-07-19
JPH05201945A (ja) 1993-08-10
AU1937392A (en) 1993-01-07
SK279706B6 (sk) 1999-02-11
NO922611D0 (no) 1992-07-02
HUT62602A (en) 1993-05-28

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