FI91860B - Förfarande för framställning av terapeutiskt användbara stilbenderivat - Google Patents

Förfarande för framställning av terapeutiskt användbara stilbenderivat Download PDF

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FI91860B
FI91860B FI890842A FI890842A FI91860B FI 91860 B FI91860 B FI 91860B FI 890842 A FI890842 A FI 890842A FI 890842 A FI890842 A FI 890842A FI 91860 B FI91860 B FI 91860B
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denotes
lower alkyl
compound
tetrahydro
ethyl
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FI890842A
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Finnish (fi)
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FI91860C (sv
FI890842A0 (sv
FI890842A (sv
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Michael Klaus
Ekkehard Weiss
Peter Mohr
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Hoffmann La Roche
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/16—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K31/33—Heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/09—Diamines
    • C07C211/10—Diaminoethanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
    • C07C211/53—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having the nitrogen atom of at least one of the amino groups further bound to a hydrocarbon radical substituted by amino groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • 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
    • C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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  • Chemical & Material Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
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  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Pulmonology (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)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (7)

1. Förfarande för framställning av terapeutiskt användbara stilbenderivat med den allmänna formeln I 5 TJ 3 R X~CH2_CH2_Y väri R1 och R2 tillsamraans bildar en rakkedig alkylen med 3 - 5 kolatomer;
15 R3 är en lägre alkyl; X är -O-, -S- eller -NR9-, varvid R9 är väte eller en lägre alkyl; Y är -S(O)mR10 eller -NHet, och da X är -NR9- eller - S-, kan det även vara -N(Rll)2/ varvid R10 och R11 är lägre 20 alkyler; -NHet är morfolinyl, tiomorfolinyl-4,4-dioxid, piperidinyl eller pyrrolidinyl; och m är 0, 1 eller 2, kännetecknat därav, att a) en förening med den allmänna formeln II 25 R3 + ^ I] p (Q)3 (II)
30. JJ A~ R bringas att reagera med en förening med den allmänna formeln III li 23 91860 X-CH2“CH2-Y sJJ I (III) H 5 eller b) en förening med den allxnänna formeln VI r3 r^V"Z R1 f I 10 (VI) bringas att reagera med en förening med den allmänna for-15 mein VII L-CH2-CH2-Y VII och om önskas oxideras i den sä erhällna föreningen med formeln I en sulfidgrupp enligt beteckningen Y till en 2 0 sulfoxid- eller sulfongrupp, varvid symbolerna R1, R2, R3, X och Y i nämnda formlerna II, III, VI och VII har ovan angivna betydelse, Q är aryl, A' är en anjon av en oorga-nisk eller organisk syra, Z är hydroxyl, merkapto, -NHR9 eller -SO^*, M+ är katjon och L är en avlägsnande grupp. 25
2. Förfarande enligt patentkrav 1, känne- t e c k n a t därav, att 4-[2-[p-[(E)-2-(5,6,7,8-tetra-hydro-5,5,8,8-tetramety 1-2-naf ty 1) propeny 1 ] f enoxi ] ety 1 ] -morfolin framställs.
3. Förfarande enligt patentkrav 1, känne-; 30 tecknat därav, att l-[2-[p-[(E)-2-(5,6,7,8-tetra- hydro-5,5,8,8-tetrametyl-2-naf tyl) propeny 1 ] f enoxi ] etyl ] pi-peridin framställs.
FI890842A 1988-02-24 1989-02-22 Förfarande för framställning av terapeutiskt användbara stilbenderivat FI91860C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH68988 1988-02-24
CH68988 1988-02-24
CH462288 1988-12-14
CH462288 1988-12-14

Publications (4)

Publication Number Publication Date
FI890842A0 FI890842A0 (sv) 1989-02-22
FI890842A FI890842A (sv) 1989-08-25
FI91860B true FI91860B (sv) 1994-05-13
FI91860C FI91860C (sv) 1994-08-25

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FI890842A FI91860C (sv) 1988-02-24 1989-02-22 Förfarande för framställning av terapeutiskt användbara stilbenderivat

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US (2) US4940707A (sv)
EP (1) EP0331983B1 (sv)
JP (1) JP2556577B2 (sv)
KR (1) KR0148217B1 (sv)
CN (1) CN1030702C (sv)
AT (1) ATE115573T1 (sv)
AU (1) AU623880B2 (sv)
BG (1) BG60935B2 (sv)
CA (1) CA1340955C (sv)
CS (1) CS277022B6 (sv)
DE (1) DE58908751D1 (sv)
DK (1) DK84889A (sv)
ES (1) ES2065929T3 (sv)
FI (1) FI91860C (sv)
GR (1) GR3015268T3 (sv)
HU (1) HU204766B (sv)
IE (1) IE66675B1 (sv)
IL (1) IL89327A (sv)
IS (1) IS1593B (sv)
MC (1) MC2011A1 (sv)
NO (1) NO169836C (sv)
NZ (1) NZ228028A (sv)
PT (1) PT89814B (sv)
YU (1) YU48067B (sv)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5734030A (en) * 1980-07-30 1982-02-24 Ishizuka Glass Ltd Preparation of glassware having opening with irregular shape
DE3926148A1 (de) * 1989-08-08 1991-02-28 Basf Ag Diarylacetylene, ihre herstellung und verwendung
AU651998B2 (en) * 1990-10-12 1994-08-11 F. Hoffmann-La Roche Ag Use of a retinoid
US5430062A (en) * 1992-05-21 1995-07-04 Research Corporation Technologies, Inc. Stilbene derivatives as anticancer agents
US5449638A (en) * 1994-06-06 1995-09-12 United Microelectronics Corporation Process on thickness control for silicon-on-insulator technology
DE19526146A1 (de) * 1995-07-07 1997-01-09 Schering Ag Triphenylethylene, Verfahren zu deren Herstellung, diese Triphenylethylene enthaltene pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln
FR2772512B1 (fr) 1997-12-16 2004-04-16 Commissariat Energie Atomique Microsysteme a element deformable sous l'effet d'un actionneur thermique
US6624197B1 (en) 1998-05-08 2003-09-23 Calyx Therapeutics, Inc. Diphenylethylene compounds
US7105552B2 (en) * 1998-05-08 2006-09-12 Theracos, Inc. Heterocyclic analogs of diphenylethylene compounds
US6331633B1 (en) 1998-05-08 2001-12-18 Calyx Therapeutics Inc. Heterocyclic analogs of diphenylethylene compounds
US6245814B1 (en) 1998-05-08 2001-06-12 Calyx Therapeutics, Inc. Diphenylethylene compounds
US6858598B1 (en) 1998-12-23 2005-02-22 G. D. Searle & Co. Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US6833373B1 (en) 1998-12-23 2004-12-21 G.D. Searle & Co. Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia
US7407978B2 (en) 1999-04-06 2008-08-05 Theracos, Inc. Heterocyclic analogs of diphenylethylene compounds
JP3498634B2 (ja) 1999-05-31 2004-02-16 関西日本電気株式会社 半導体装置の製造方法
US6525093B1 (en) 1999-11-08 2003-02-25 Calyx Therapeutics Inc. Compounds to treat diabetes and associated conditions
US20020002200A1 (en) * 2000-02-04 2002-01-03 Bishwagit Nag Novel diphenylethylene compounds
US20080108825A1 (en) * 1999-11-08 2008-05-08 Theracos, Inc. Compounds for treatment of inflammation, diabetes and related disorders
US7323496B2 (en) * 1999-11-08 2008-01-29 Theracos, Inc. Compounds for treatment of inflammation, diabetes and related disorders
US20080103302A1 (en) * 2000-02-04 2008-05-01 Theracos, Inc. Compounds for treatment of inflammation, diabetes and related disorders
FR2830860A1 (fr) * 2001-10-12 2003-04-18 Univ Pasteur Procede de synthese du (z)-3, 5, 4'-trimethoxystilbene, compose obtenu et utilisations dudit compose, notamment comme medicament, en particulier comme anticancereux
US20050014729A1 (en) * 2003-07-16 2005-01-20 Pharmacia Corporation Method for the treatment or prevention of dermatological disorders with a cyclooxygenase-2 inhibitor alone and in combination with a dermatological treatment agent and compositions therewith
US20070276172A1 (en) 2006-03-28 2007-11-29 Sinha Arun K Single step microwave induced process for the preparation of substituted stilbenes and its analogs
US20100298402A1 (en) * 2007-11-06 2010-11-25 Orchid Research Laboratories Limited Stilbene derivatives as pstat3/il-6 inhibitors
WO2010113005A2 (en) 2009-03-27 2010-10-07 Council Of Scientific & Industrial Research One pot multicomponent synthesis of some novel hydroxy stilbene derivatives with alpha, beta-carbonyl conjugation under microwave irradiation
WO2013003112A1 (en) 2011-06-27 2013-01-03 The Jackson Laboratory Methods and compositions for treatment of cancer and autoimmune disease
TW201702218A (zh) 2014-12-12 2017-01-16 美國杰克森實驗室 關於治療癌症、自體免疫疾病及神經退化性疾病之組合物及方法
CN112190688A (zh) * 2020-09-09 2021-01-08 广州医科大学附属第一医院（广州呼吸中心） 粘蛋白muc1在制备具有延缓肺衰老功效的药物中的应用

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE544087C (de) 1927-04-17 1932-02-13 I G Farbenindustrie Akt Ges Verfahren zur Darstellung aromatischer N-Dialkylaminoalkylaminoaldehyde und ihrer Derivate
GB456534A (en) 1935-05-11 1936-11-11 Ig Farbenindustrie Ag Process for the manufacture of nitrogenous aromatic aldehydes
NL302207A (sv) * 1962-12-19
US3437607A (en) * 1965-03-31 1969-04-08 Upjohn Co Polyurethane pre-mixes containing dihydroxy nitrogen containing phosphonates
US3483209A (en) 1967-05-02 1969-12-09 Ciba Geigy Corp Aralkylamines
CH481061A (de) * 1967-06-01 1969-11-15 Agripat Sa Verfahren zur Herstellung neuer quaternärer Ammoniumsalze
DE1767931C3 (de) * 1967-10-26 1973-09-27 Boehringer Mannheim Gmbh, 6800 Mannheim Diagnostisches Mittel und Verfahren zum Nachweis von Urobilinogen-Körpern
JPS546948B2 (sv) * 1972-06-05 1979-04-02
JPS6045632B2 (ja) * 1978-03-09 1985-10-11 三菱化学株式会社 ω−アミノアルコキシスチルベン類及びその酸付加塩
US4369310A (en) * 1979-11-19 1983-01-18 Ciba-Geigy Ltd. Bleachable dyes
DE3040911A1 (de) * 1980-10-30 1982-06-03 Bayer Ag, 5090 Leverkusen Kationische styrylfarbstoffe, ihre herstellung und ihre verwendung zum faerben von natuerlichen und synthetischen kationisch anfaerbbaren substraten
CA1162200A (en) * 1981-02-13 1984-02-14 Michael Klaus Process for the manufacture of indanyl (or tetrahydronaphthyl)propenyl phenyl derivatives
JPS62964A (ja) * 1985-06-26 1987-01-06 Minolta Camera Co Ltd 電子写真感光体
DE3770547D1 (de) * 1986-02-18 1991-07-11 Electronics For Industry Ltd Verfahren und geraet zum kochen von teigwaren.
CH668962A5 (de) * 1986-05-13 1989-02-15 Hoffmann La Roche Tetrahydronaphthyl-propenyl-phenole.
ZW7487A1 (en) * 1986-05-23 1987-12-16 Hoffmann La Roche Tetrahydronaphthaline and indane derivatives

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CN1030702C (zh) 1996-01-17
HU204766B (en) 1992-02-28
NO890767L (no) 1989-08-25
KR890012954A (ko) 1989-09-20
JPH023629A (ja) 1990-01-09
YU39589A (en) 1991-10-31
FI91860C (sv) 1994-08-25
NO169836B (no) 1992-05-04
HUT50756A (en) 1990-03-28
CA1340955C (en) 2000-04-11
AU623880B2 (en) 1992-05-28
PT89814A (pt) 1989-10-04
EP0331983A2 (de) 1989-09-13
US5106981A (en) 1992-04-21
GR3015268T3 (en) 1995-06-30
EP0331983B1 (de) 1994-12-14
AU3025789A (en) 1989-08-24
IS3437A7 (is) 1989-08-25
NO890767D0 (no) 1989-02-23
BG60935B2 (bg) 1996-06-28
YU48067B (sh) 1996-10-18
PT89814B (pt) 1994-07-29
IS1593B (is) 1996-04-12
DK84889A (da) 1989-08-25
IL89327A (en) 1994-12-29
MC2011A1 (fr) 1990-02-16
CS96289A3 (en) 1992-06-17
JP2556577B2 (ja) 1996-11-20
FI890842A0 (sv) 1989-02-22
FI890842A (sv) 1989-08-25
KR0148217B1 (ko) 1998-08-17
NO169836C (no) 1992-08-12
CN1035500A (zh) 1989-09-13
IE66675B1 (en) 1996-01-24
CS277022B6 (en) 1992-11-18
US4940707A (en) 1990-07-10
IE890581L (en) 1989-08-24
ATE115573T1 (de) 1994-12-15
DE58908751D1 (de) 1995-01-26
EP0331983A3 (en) 1990-11-07
NZ228028A (en) 1991-11-26
DK84889D0 (da) 1989-02-23
ES2065929T3 (es) 1995-03-01

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