WO1991013899A1 - Composes tricyclo - Google Patents
Composes tricyclo Download PDFInfo
- Publication number
- WO1991013899A1 WO1991013899A1 PCT/JP1991/000314 JP9100314W WO9113899A1 WO 1991013899 A1 WO1991013899 A1 WO 1991013899A1 JP 9100314 W JP9100314 W JP 9100314W WO 9113899 A1 WO9113899 A1 WO 9113899A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- hydroxy
- och
- symbol
- oxo
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
-
- 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
- A61P31/04—Antibacterial 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Definitions
- R is hydroxy or alkoxy
- X is oxo or (H, OH)
- n is an integer of 1 or 2
- the symbol of a line and dotted line is a single bond or a double bond.
- R , R , R , R , x and n are each as defined above.
- Suitable alkyl moiety in "alkoxy" and "lower alkyl which may have one or more hydroxy” may include a straigh or branched lower alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, hexyl, and the like. And particularly, the preferable “alkoxy” is methoxy, and the preferable "lower alkyl which may have one or more - 6 -
- hydroxy is propyl or propyl having one or two hydroxy such as 2-hydroxypropyl and 2,3-dihydroxypropyl.
- Suitable "aryl which may have suitable substituent(s)” may include phenyl, tolyl, xylyl, mesityl, naphthyl, and the like, which may have suitable substituent(s) such as halogen (e.g. fluoro, chloro, bromo, iodo) , and the like.
- halogen e.g. fluoro, chloro, bromo, iodo
- the compound (I) or a salt thereof can be prepared by introducing "R NHCO-" group into the compound (II) or its reactive derivative at the hydroxy group or a salt thereof.
- Suitable introducing agent of "R NHCO-" group used in this reaction may be a conventional one such as carbamic acid and their reactive derivative, for example, an acid halide, an acid anhydride, an activated amide, an activated ester, isocyanate, and the like.
- reactive derivative may include acid chloride, acid bromide, a mixed acid anhydride with an acid such as substituted phosphoric acid (e.g. dialkylphosphoric acid, phenylphosphoric acid, diphenylphosphoric acid, dibenzylphosphoric acid, halogenated phosphoric acid, etc.), dialkylphosphorous acid, sulfurous acid, thiosulfuric acid, sulfuric acid, alkyl carbonate (e.g.
- aliphatic carboxylic acid e.g. pivalic acid, pentanoic acid, isopentanoic acid, 2-eth ⁇ lbutyric acid, trichloroacetic trifluoroacetic acid, etc.
- aromatic carboxylic acid e.g. benzoic acid, etc.
- a symmetrical acid anhydride an activated acid amide wit a heterocyclic compound containing imino function such as imidazole, 4-substituted imidazole, dimethylpyrazole, triazole and tetrazole, an activated ester (e.g.
- R is as defined above, preferably aryl which ma have suitable substituent(s) , and
- R is as defined above, preferably hydrogen or lower alkyl which may have one or more hydroxy.
- Suitable reactive derivative at the hydroxy group of the compound (II) may be conventional one which is capable ooff rreeppllaacciinngg aa hhyyddrrooxxyy ggrroouupp wwiitthh '"R NHCOO-" such as an activated ester as mentioned above,
- the reaction is preferably conducted in the presence of an organic or inorganic base such as alkali metal (e.g. lithium, sodium, potassium, etc.), alkaline earth metal (e.g. calcium, etc.), alkali metal hydride (e.g. sodium hydride, etc.), alkaline earth metal hydride (e.g. calcium hydride, etc.), alkali metal hydroxide (e.g. sodium hydroxide, potassium hydroxide, etc.), alkali metal carbonate (e.g. sodium carbonate, potassium carbonate, etc.), alkali metal hydrogen carbonate (e.g. sodium hydrogen carbonate, potassium hydrogen carbonate, etc.), alkali metal alkoxide (e.g.
- alkali metal e.g. lithium, sodium, potassium, etc.
- alkaline earth metal e.g. calcium, etc.
- alkali metal hydride e.g. sodium hydride, etc.
- alkaline earth metal hydride e.g. calcium hydride,
- alkali metal alkanoic acid e.g. sodium acetate, etc.
- trialkylamine e.g. triethylamine, etc.
- pyridine compound e.g. pyridine, lutidine, picoline, 4-N,N-dimeth ⁇ laminopyridine, etc.
- quinoline and the like.
- the reaction is usually conducted in a conventional solvent which does not adversely influence the reaction such as water, acetone, dichloromethane, alcohol (e.g. methanol, ethanol, etc.), tetrahydrofuran, pyridine, benzene, N,N-dimethylformamide, etc., or a mixture thereof, and further in case that the base or the iinnttrroodduucciinngg aaggeenntt ooff tthhee RR NNHHCCO- group is in liquid, it can also be used as a solvent.
- the reaction temperature is not critical and the reaction is usually conducted under from cooling to heating.
- this process also includes, within a scope thereof, a case that the compound (II) having a partial structure of the formula :
- Reduction in this process can be conducted by a conventional method which is capable of reducing an allyl group to a propyl group, such as catalytic reduction, or the like.
- Suitable catalysts used in catalytic reduction are conventional ones such as platinum catalysts (e.g. platinum plate, spongy platinum, platinum black, colloida platinum, platinum oxide, platinum wire, etc.), palladium catalysts (e.g. spongy palladium, palladium black, palladium oxide, palladium on carbon, colloidal palladium, palladium on barium sulfate, palladium on barium carbonate, etc.), nickel catalysts (e.g. reduced nickel, nickel oxide, Raney nickel, etc.), cobalt catalysts (e.g. reduced cobalt, Raney cobalt, etc.), iron catalysts (e.g. reduced iron, Raney iron, etc.), copper catalysts (e.g. reduced copper, Raney copper, Ullman copper, etc. ) , and the like.
- reaction temperature of this reduction is not critical and the reaction is usually conducted under from cooling to warming.
- This process includes, within a scope thereof, a cas that the double bond defined by the symbol of a line and dotted line may occasionally be reduced during the reaction to give a single bond.
- the tricyclo compounds (I) are also useful in the topical administration for the treatment an the prophylaxis of inflammatory and hyperproliferative skin diseases and cutaneous manifestations of i munologically-mediated illnesses, such as, psoriasis, atopical dermatitis, contact dermatitis and further eczematous dermatitises, seborrhoeis dermatitis, Lichen planus, Pemphigus, bullous Pemphigoid, Epidermolysis bullosa, urticaria, angioedemas, vasculitides, erythemas, cutaneous eosinophilias, Lupus erythematosus and Alopecia areata.
- i munologically-mediated illnesses such as, psoriasis, atopical dermatitis, contact dermatitis and further eczematous dermatitises, seborrhoeis dermatitis, Lichen planus, Pemphigus
- bronchial asthma allergic asthma, intrinsic asthma, extrinsic asthma and dust asthma
- chronic or inveterate asthma e.g. late asthma and airway hyper-responsiveness
- bronchitis and the like nephrotic syndrome such as glomerulonephritis
- hemolytic-uremic syndrome e.g., hemolytic-uremic syndrome
- photoallergic sensitivity e.g. male pattern alopecia or alopecia senilis; etc.
- the pharmacological test data of the tricyclo compounds (I) is illustrated in the following.
- the MLR test was preformed in microtiter plates, with each well containing 5 x 10 C57BL/6 responder cells
- I C value (mol concentration to suppress 50% or MLR) was calculated by a conventional method, which is shown in the following Table 1.
- Table 1 I C CQ value of MLR test on tricyclo compounds (I)
- the pharmaceutical composition of this invention can be used in the form of a pharmaceutical preparation, for example, in solid, semisolid or liquid form, which contains the tricyclo compounds (I), as an active ingredient, in admixture with an organic or inorganic carrier or excipient suitable for external, enteral or parenteral applications.
- the active ingredient may be compounded, for example, with the usual non-toxic, pharmaceutically acceptable carriers for tablets, pellets, capsules, suppositories, solutions, emulsions, suspensions, injections, ointments, liniments, eye drops lotion, gel, cre e and any other form suitable for use.
- the carriers which can be used are water, glucose, lactose, gum acacia, gelatin, mannitol, starch paste, magnesium trisilicate, talc, corn starch, keratin, colloidal silica, potato starch, urea and other carriers suitable for use in manufacturing preparations, in solid, semisolid, or liquid form, and in addition auxiliary, stabilizing, thickening, solubilizing an coloring agents and perfumes may be used.
- a solubilizin agent there may be exemplified water-soluble cellulose polymer (i.e. hydroxypropyl methylcellulose, etc.), water-soluble glycol (i.e. propylene glycol, etc.), etc.
- the active object compound is included in the pharmaceutical composition in an amount sufficient to produce the desired effect upon the process or condition of diseases.
- this composition for applying this composition to human, it is preferable to apply it by parenteral or enteral administration.
- a daily dose of about 0.01-1000 mg, preferably 0.1-500 mg and more preferably 0.5-100 mg, of the active ingredient is generally given for treating diseases, and an average single dose of about 0.5 mg, 1 mg, 5 mg, 10 mg, 50 mg, 100 mg, 250 mg and 500 mg is generally administered.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Transplantation (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Composés de la formule (I) dans laquelle R1 représente hydrogène, alkyle inférieur pouvant avoir un ou plusieurs hydroxy, ou aryle pouvant avoir un/des substituant(s) approprié(s), R2 représente hydrogène, hydroxy ou hydroxy protégé, R3 représente méthyle, étyle, propyle ou allyle, R4 représente hdyroxy ou alcoxy, R5 représente oxo, (H, OH) ou (H, alcoxy), X représente oxo ou (H, OH), n représente un nombre entier de 1 ou de 2, et le symbole d'une ligne ou d'une ligne pointillée représente une seule liaison ou une double liaison, et sels, de ces composés. Procédés de production de ces composés, compositions contenant ces composés, et utilisation de ces composés comme agents immunosuppresseurs.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9005521.1 | 1990-03-12 | ||
GB909005521A GB9005521D0 (en) | 1990-03-12 | 1990-03-12 | Tricyclo compounds,a process for their production and a pharmaceutical composition containing the same |
GB909017450A GB9017450D0 (en) | 1990-08-09 | 1990-08-09 | Tricyclo compounds,a process for their production and a pharmaceutical composition containing the same |
GB9017450.9 | 1990-08-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1991013899A1 true WO1991013899A1 (fr) | 1991-09-19 |
Family
ID=26296777
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1991/000314 WO1991013899A1 (fr) | 1990-03-12 | 1991-03-08 | Composes tricyclo |
Country Status (2)
Country | Link |
---|---|
JP (1) | JPH05504956A (fr) |
WO (1) | WO1991013899A1 (fr) |
Cited By (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5143918A (en) * | 1990-10-11 | 1992-09-01 | Merck & Co., Inc. | Halomacrolides and derivatives having immunosuppressive activity |
US5162334A (en) * | 1991-05-13 | 1992-11-10 | Merck & Co., Inc. | Amino O-alkyl, O-alkenyl and O-alkynlmacrolides having immunosuppressive activity |
US5189042A (en) * | 1991-08-22 | 1993-02-23 | Merck & Co. Inc. | Fluoromacrolides having immunosuppressive activity |
EP0515071A3 (en) * | 1991-05-13 | 1993-03-03 | Merck & Co. Inc. | O-aryl, o-alkyl, o-alkenyl and o-alkynylmacrolides having immunosuppressive activity |
US5208241A (en) * | 1991-09-09 | 1993-05-04 | Merck & Co., Inc. | N-heteroaryl, n-alkylheteroaryl, n-alkenylheteroaryl and n-alkynylheteroarylmacrolides having immunosuppressive activity |
US5262533A (en) * | 1991-05-13 | 1993-11-16 | Merck & Co., Inc. | Amino O-aryl macrolides having immunosuppressive activity |
US5262423A (en) * | 1992-10-29 | 1993-11-16 | American Home Products Corporation | Rapamycin arylcarbonyl and alkoxycarbonyl carbamates as immunosuppressive and antifungal agents |
US5284877A (en) * | 1992-06-12 | 1994-02-08 | Merck & Co., Inc. | Alkyl and alkenyl macrolides having immunosuppressive activity |
US5284840A (en) * | 1992-06-12 | 1994-02-08 | Merck & Co., Inc. | Alkylidene macrolides having immunosuppressive activity |
US5302584A (en) * | 1992-10-13 | 1994-04-12 | American Home Products Corporation | Carbamates of rapamycin |
EP0642516A4 (fr) * | 1991-09-05 | 1994-06-15 | Abbott Lab | Immunomodulateurs macrocycliques. |
US5434260A (en) * | 1992-10-13 | 1995-07-18 | American Home Products Corporation | Carbamates of rapamycin |
US5463048A (en) * | 1994-06-14 | 1995-10-31 | American Home Products Corporation | Rapamycin amidino carbamates |
US5480989A (en) * | 1992-10-13 | 1996-01-02 | American Home Products Corporation | Carbamates of rapamycin |
US5480988A (en) * | 1992-10-13 | 1996-01-02 | American Home Products Corporation | Carbamates of rapamycin |
EP0689546A1 (fr) * | 1993-03-17 | 1996-01-03 | Abbott Laboratories | Carbamates macrocycliques immunomodulateurs |
US5484791A (en) * | 1992-10-13 | 1996-01-16 | American Home Products Corporation | Carbamates of rapamycin |
US5532248A (en) * | 1991-05-13 | 1996-07-02 | Merck Co., Inc. | O-aryl,O-alkyl, and O-alkenyl-macrolides having immunosuppressive activity |
US5534632A (en) * | 1991-09-05 | 1996-07-09 | Abbott Laboratories | Macrocyclic carbamate immunomodulators |
WO1996031514A1 (fr) * | 1995-04-06 | 1996-10-10 | Novartis Ag | Ascomycines |
US5693648A (en) * | 1994-09-30 | 1997-12-02 | Merck & Co., Inc. | O-aryl, O-alkyl, O-alkenyl and O-alkynyl-macrolides having immunosuppressive activity |
US5708002A (en) * | 1991-09-05 | 1998-01-13 | Abbott Laboratories | Macrocyclic immunomodulators |
US6352998B2 (en) | 1994-10-26 | 2002-03-05 | Novartis Ag | Pharmaceutical compositions |
EP1687283A2 (fr) * | 2003-11-21 | 2006-08-09 | Dade Behring Inc. | Procede et composition servant a determiner fk 506 |
EP2583678A2 (fr) | 2004-06-24 | 2013-04-24 | Novartis Vaccines and Diagnostics, Inc. | Immunopotentiateurs de petites molécules et dosages pour leur détection |
US9402802B2 (en) | 1998-12-03 | 2016-08-02 | Meda Pharma Sarl | Topical compositions comprising ascomycins |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0184162A2 (fr) * | 1984-12-03 | 1986-06-11 | Fujisawa Pharmaceutical Co., Ltd. | Composés tricycliques, procédé pour leur préparation et composition pharmaceutique les contenant |
EP0293892A2 (fr) * | 1987-06-05 | 1988-12-07 | Fujisawa Pharmaceutical Co., Ltd. | Anticorps anti-FR-900506, substance et procédé d'essai enzymatique immunologique de haute sensibilité |
EP0315978A2 (fr) * | 1987-11-09 | 1989-05-17 | Sandoz Ag | Utilisation de dérivés de 11,28-dioxa-4-azatricyclo[22.3.1.0 4,9]octacos-18-ène et compositions pharmaceutiques les contenant |
-
1991
- 1991-03-08 JP JP3505321A patent/JPH05504956A/ja active Pending
- 1991-03-08 WO PCT/JP1991/000314 patent/WO1991013899A1/fr unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0184162A2 (fr) * | 1984-12-03 | 1986-06-11 | Fujisawa Pharmaceutical Co., Ltd. | Composés tricycliques, procédé pour leur préparation et composition pharmaceutique les contenant |
EP0293892A2 (fr) * | 1987-06-05 | 1988-12-07 | Fujisawa Pharmaceutical Co., Ltd. | Anticorps anti-FR-900506, substance et procédé d'essai enzymatique immunologique de haute sensibilité |
EP0315978A2 (fr) * | 1987-11-09 | 1989-05-17 | Sandoz Ag | Utilisation de dérivés de 11,28-dioxa-4-azatricyclo[22.3.1.0 4,9]octacos-18-ène et compositions pharmaceutiques les contenant |
Cited By (54)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5143918A (en) * | 1990-10-11 | 1992-09-01 | Merck & Co., Inc. | Halomacrolides and derivatives having immunosuppressive activity |
US5532248A (en) * | 1991-05-13 | 1996-07-02 | Merck Co., Inc. | O-aryl,O-alkyl, and O-alkenyl-macrolides having immunosuppressive activity |
US5162334A (en) * | 1991-05-13 | 1992-11-10 | Merck & Co., Inc. | Amino O-alkyl, O-alkenyl and O-alkynlmacrolides having immunosuppressive activity |
EP0515071A3 (en) * | 1991-05-13 | 1993-03-03 | Merck & Co. Inc. | O-aryl, o-alkyl, o-alkenyl and o-alkynylmacrolides having immunosuppressive activity |
US5250678A (en) * | 1991-05-13 | 1993-10-05 | Merck & Co., Inc. | O-aryl, O-alkyl, O-alkenyl and O-alkynylmacrolides having immunosuppressive activity |
US5262533A (en) * | 1991-05-13 | 1993-11-16 | Merck & Co., Inc. | Amino O-aryl macrolides having immunosuppressive activity |
US5189042A (en) * | 1991-08-22 | 1993-02-23 | Merck & Co. Inc. | Fluoromacrolides having immunosuppressive activity |
EP0642516A4 (fr) * | 1991-09-05 | 1994-06-15 | Abbott Lab | Immunomodulateurs macrocycliques. |
EP0642516A1 (fr) * | 1991-09-05 | 1995-03-15 | Abbott Laboratories | Immunomodulateurs macrocycliques |
US5708002A (en) * | 1991-09-05 | 1998-01-13 | Abbott Laboratories | Macrocyclic immunomodulators |
US5534632A (en) * | 1991-09-05 | 1996-07-09 | Abbott Laboratories | Macrocyclic carbamate immunomodulators |
US5208241A (en) * | 1991-09-09 | 1993-05-04 | Merck & Co., Inc. | N-heteroaryl, n-alkylheteroaryl, n-alkenylheteroaryl and n-alkynylheteroarylmacrolides having immunosuppressive activity |
US5284877A (en) * | 1992-06-12 | 1994-02-08 | Merck & Co., Inc. | Alkyl and alkenyl macrolides having immunosuppressive activity |
US5284840A (en) * | 1992-06-12 | 1994-02-08 | Merck & Co., Inc. | Alkylidene macrolides having immunosuppressive activity |
US5504204A (en) * | 1992-10-13 | 1996-04-02 | American Home Products Corporation | Carbamates of rapamycin |
US5559119A (en) * | 1992-10-13 | 1996-09-24 | American Home Products Corporation | Carbamates of rapamycin |
US5480988A (en) * | 1992-10-13 | 1996-01-02 | American Home Products Corporation | Carbamates of rapamycin |
US5302584A (en) * | 1992-10-13 | 1994-04-12 | American Home Products Corporation | Carbamates of rapamycin |
US5484791A (en) * | 1992-10-13 | 1996-01-16 | American Home Products Corporation | Carbamates of rapamycin |
US5484790A (en) * | 1992-10-13 | 1996-01-16 | American Home Products Corporation | Carbamates of rapamycin |
US5486522A (en) * | 1992-10-13 | 1996-01-23 | American Home Products Corporation | Carbamates of rapamycin |
US5486523A (en) * | 1992-10-13 | 1996-01-23 | American Home Products Corporation | Carbamates of rapamycin |
US5486524A (en) * | 1992-10-13 | 1996-01-23 | American Home Products Corporation | Carbamates of rapamycin |
US5488054A (en) * | 1992-10-13 | 1996-01-30 | American Home Products Corporation | Carbamates of Rapamycin |
US5489595A (en) * | 1992-10-13 | 1996-02-06 | American Home Products Corporation | Carbamates of rapamycin |
US5489680A (en) * | 1992-10-13 | 1996-02-06 | American Home Products Corporation | Carbamates of rapamycin |
US5480989A (en) * | 1992-10-13 | 1996-01-02 | American Home Products Corporation | Carbamates of rapamycin |
US5559120A (en) * | 1992-10-13 | 1996-09-24 | American Home Products Corporation | Carbamates of rapamycin |
US5508399A (en) * | 1992-10-13 | 1996-04-16 | American Home Products Corporation | Carbamates of rapamycin |
US5559227A (en) * | 1992-10-13 | 1996-09-24 | American Home Products Corporation | Carbamates of rapaycin |
US5516780A (en) * | 1992-10-13 | 1996-05-14 | American Home Products Corporation | Carbamates of rapamycin |
US5530121A (en) * | 1992-10-13 | 1996-06-25 | American Home Products Corporation | Carbamates of rapamycin |
US5530007A (en) * | 1992-10-13 | 1996-06-25 | American Home Products Corporation | Carbamates of rapamycin |
US5559112A (en) * | 1992-10-13 | 1996-09-24 | American Home Products Corporation | Carbamates of rapamycin |
US5532355A (en) * | 1992-10-13 | 1996-07-02 | American Home Products Corporation | Carbamates of rapamycin |
US5434260A (en) * | 1992-10-13 | 1995-07-18 | American Home Products Corporation | Carbamates of rapamycin |
US5550133A (en) * | 1992-10-13 | 1996-08-27 | American Home Products Corporation | Carbamates of rapamycin |
US5262423A (en) * | 1992-10-29 | 1993-11-16 | American Home Products Corporation | Rapamycin arylcarbonyl and alkoxycarbonyl carbamates as immunosuppressive and antifungal agents |
EP0689546A4 (fr) * | 1993-03-17 | 1996-04-03 | Abbott Lab | Carbamates macrocycliques immunomodulateurs |
EP0689546A1 (fr) * | 1993-03-17 | 1996-01-03 | Abbott Laboratories | Carbamates macrocycliques immunomodulateurs |
US5541191A (en) * | 1994-06-14 | 1996-07-30 | American Home Products Corporation | Rapamycin amidino carbamates |
US5541192A (en) * | 1994-06-14 | 1996-07-30 | American Home Products Corporation | Rapamycin amidino carbamates |
US5508286A (en) * | 1994-06-14 | 1996-04-16 | American Home Products Corporation | Rapamycin amidino carbamates |
US5463048A (en) * | 1994-06-14 | 1995-10-31 | American Home Products Corporation | Rapamycin amidino carbamates |
US5637590A (en) * | 1994-06-14 | 1997-06-10 | American Home Products Corporation | Rapamycin amidino carbamates |
US5693648A (en) * | 1994-09-30 | 1997-12-02 | Merck & Co., Inc. | O-aryl, O-alkyl, O-alkenyl and O-alkynyl-macrolides having immunosuppressive activity |
US6352998B2 (en) | 1994-10-26 | 2002-03-05 | Novartis Ag | Pharmaceutical compositions |
WO1996031514A1 (fr) * | 1995-04-06 | 1996-10-10 | Novartis Ag | Ascomycines |
US5925649A (en) * | 1995-04-06 | 1999-07-20 | Novartis Ag | Ascomycins |
US9402802B2 (en) | 1998-12-03 | 2016-08-02 | Meda Pharma Sarl | Topical compositions comprising ascomycins |
EP1687283A2 (fr) * | 2003-11-21 | 2006-08-09 | Dade Behring Inc. | Procede et composition servant a determiner fk 506 |
US7186518B2 (en) | 2003-11-21 | 2007-03-06 | Dade Behring Inc. | Method and composition useful for determining FK 506 |
EP1687283A4 (fr) * | 2003-11-21 | 2008-09-24 | Siemens Healthcare Diagnostics | Procede et composition servant a determiner fk 506 |
EP2583678A2 (fr) | 2004-06-24 | 2013-04-24 | Novartis Vaccines and Diagnostics, Inc. | Immunopotentiateurs de petites molécules et dosages pour leur détection |
Also Published As
Publication number | Publication date |
---|---|
JPH05504956A (ja) | 1993-07-29 |
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