ES2093237T3 - Derivados de hidrazina farmacologicamente activos y procedimiento para su obtencion. - Google Patents

Derivados de hidrazina farmacologicamente activos y procedimiento para su obtencion.

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Publication number
ES2093237T3
ES2093237T3 ES92810490T ES92810490T ES2093237T3 ES 2093237 T3 ES2093237 T3 ES 2093237T3 ES 92810490 T ES92810490 T ES 92810490T ES 92810490 T ES92810490 T ES 92810490T ES 2093237 T3 ES2093237 T3 ES 2093237T3
Authority
ES
Spain
Prior art keywords
substituted
replaced
hydrogen
rent
independent
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
ES92810490T
Other languages
English (en)
Inventor
Alexander Dr Fassler
Guido Dr Bold
Marc Dr Lang
Peter Dr Schneider
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
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.)
Filing date
Publication date
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Application granted granted Critical
Publication of ES2093237T3 publication Critical patent/ES2093237T3/es
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)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Quinoline Compounds (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

LA INVENCION SE REFIERE A COMPUESTOS DE LA FORMULA (I) DONDE R1 Y R9 INDEPENDIENTES UNO DE OTRO SON HIDROGENO, ACIL, ALQUIL NO SUSTITUIDO O SUSTITUIDO ALQUENIL O ALQUINIL; HETEROCICLIL, SULFO A TRAVES DE ALQUIL SUSTITUIDO O INSUSTITUIDO, ARIL, HETEROCICLIL, ALCOXI, QUE ES SUSTITUIDO O INSUSTITUIDO, O SULFONIL SUSTITUIDO A TRAVES DE ARILOXI, SULFAMOIL, QUE ES SUSTITUIDO O INSUSTITUIDO EN NITROGENO, O A TRAVES DE UNO O DOS ARIL INDEPENDIENTES UNO DE OTRO SUSTITUIDO O INSUSTITUIDO, DE CICLOALQUIL SUSTITUIDO O INSUSTITUIDO, DE ARIL DE HIDROXI, DE ALCOXI SUSTITUIDO O INSUSTITUIDO, DE CICLOALCOXI Y DE ARILOXI CON FOSFONIL SUSTITUIDO CON RESTO ELEGIDO, CON LA MEDIDA QUE EN EL CASO MAS ALTO SIGNIFICAN EL RESTO R1 Y R9 HIDROGENO; Y R2 Y R8 INDEPENDIENTE UNO DE OTRO HIDROGENO O UN RESTO CONOCIDO DE LOS INDICADOS PARA R1 Y R9; O, LOS PARES R1 Y R2 SUSTITUIDOS, O R8 Y R9 INDEPENDIENTES UNO DE OTRO DE FORMA CONJUNTA CON EL ATOMO DE NITROGENO AL QUE ESTAN UNIDOS, PUEDEN FORMAR ANILLOS HETEROCICLICOS DETERMINADOS; R3 Y R4 INDEPENDIENTES UNO DE OTRO SON HIDROGENO, ALQUIL SUSTITUIDO O INSUSTITUIDO O CICLOALQUIL; ARIL; HETEROCICLIL; O ALQUENIL SUSTITUIDO O INSUSTITUIDO; O R3 Y R4 CONJUNTAMENTE ALQUILENO INSUSTITUIDO SUSTITUIDO, ALQUILIDENO, O ALQUILENOS BENZOCONDENSADOS. R5 ES HIDROXI; R6 ES HIDROGENO; O R5 Y R6 CONJUNTAMENTE SON OXO; Y R7 ES ALQUIL INSUSTITUIDO O SUSTITUIDO O CICLOALQUIL; ARIL; HETERECICLIL; O ALQUENIL SUSTITUIDO O INSUSTITUIDO; ASI COMO LAS SALES DE LOS COMPUESTOS CONOCIDOS, Y LOS GRUPOS EXISTENTES FORMADORES DE SALES. SE PRESENTA ADEMAS UN PROCESO PARA SU FABRICACION, PREPARADO FARMACEUTICO, LA UTILIZACION COMO MEDICAMENTO O PARA LA FABRICACION DE PREPARADOS FARMACEUTICOS, ASI COMO NUEVOS PRODUCTOS INTERMEDIOS PARA LA FABRICACION DE ESTOS COMPUESTOS.
ES92810490T 1991-07-03 1992-06-25 Derivados de hidrazina farmacologicamente activos y procedimiento para su obtencion. Expired - Lifetime ES2093237T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH196291 1991-07-03

Publications (1)

Publication Number Publication Date
ES2093237T3 true ES2093237T3 (es) 1996-12-16

Family

ID=4222677

Family Applications (1)

Application Number Title Priority Date Filing Date
ES92810490T Expired - Lifetime ES2093237T3 (es) 1991-07-03 1992-06-25 Derivados de hidrazina farmacologicamente activos y procedimiento para su obtencion.

Country Status (27)

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

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US6071895A (en) 1992-03-11 2000-06-06 Narhex Limited Polar-substituted hydrocarbons
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PT2069303E (pt) 2006-07-21 2016-06-08 Gilead Sciences Inc Inibidores de protease antiviral
UY37592A (es) 2017-02-06 2018-08-31 Gilead Sciences Inc Compuestos inhibidores del vih
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
CN116988204B (zh) * 2023-07-13 2025-10-31 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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NO922611D0 (no) 1992-07-02
IL102354A (en) 1997-01-10
NO178541C (no) 1996-04-17
SK279706B6 (sk) 1999-02-11
IL102354A0 (en) 1993-01-14
KR100255099B1 (ko) 2000-05-01
HUT62602A (en) 1993-05-28
NO178541B (no) 1996-01-08
DE59207226D1 (de) 1996-10-31
SK206292A3 (en) 1995-02-08
HU9202215D0 (en) 1992-10-28
KR930002372A (ko) 1993-02-23
AU1937392A (en) 1993-01-07
CN1068333A (zh) 1993-01-27
NZ243410A (en) 1995-02-24
PL295100A1 (en) 1993-03-22
EP0521827A1 (de) 1993-01-07
CZ280651B6 (cs) 1996-03-13
FI923017A7 (fi) 1993-01-04
RU2092492C1 (ru) 1997-10-10
MX9203899A (es) 1993-01-01
FI114634B (fi) 2004-11-30
SA93140336B1 (ar) 2006-08-14
AU660469B2 (en) 1995-06-29
TW309512B (es) 1997-07-01
CA2072785C (en) 2006-07-25
PL171232B1 (pl) 1997-03-28
DZ1591A1 (fr) 2002-02-17
MA22581A1 (fr) 1993-04-01
CN1054598C (zh) 2000-07-19
NO922611L (no) 1993-01-04
ZA924914B (en) 1993-03-31
IE922166A1 (en) 1993-01-13
CA2072785A1 (en) 1993-01-04
EP0521827B1 (de) 1996-09-25
ATE143355T1 (de) 1996-10-15
JPH05201945A (ja) 1993-08-10
GR3021169T3 (en) 1996-12-31
HU219915B (hu) 2001-09-28
DK0521827T3 (da) 1996-11-11
IE80471B1 (en) 1998-07-29
FI923017A0 (fi) 1992-06-29
JP3187535B2 (ja) 2001-07-11
CZ206292A3 (en) 1993-11-17

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