AR053449A1 - Derivados de tiofeno agonistas del receptor s1p1/edg1 - Google Patents
Derivados de tiofeno agonistas del receptor s1p1/edg1Info
- Publication number
- AR053449A1 AR053449A1 ARP060101134A ARP060101134A AR053449A1 AR 053449 A1 AR053449 A1 AR 053449A1 AR P060101134 A ARP060101134 A AR P060101134A AR P060101134 A ARP060101134 A AR P060101134A AR 053449 A1 AR053449 A1 AR 053449A1
- Authority
- AR
- Argentina
- Prior art keywords
- pyrrolidin
- carboxylic acid
- propoxy
- alkyl
- hydroxy
- Prior art date
Links
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 title 2
- 101001021281 Homo sapiens Protein HEXIM1 Proteins 0.000 title 1
- 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 title 1
- 101710155454 Sphingosine 1-phosphate receptor 1 Proteins 0.000 title 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title 1
- 239000000556 agonist Substances 0.000 title 1
- -1 2,3-dihydroxypropyl Chemical group 0.000 abstract 21
- 125000000217 alkyl group Chemical group 0.000 abstract 15
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Chemical compound OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 abstract 11
- GFZWHAAOIVMHOI-UHFFFAOYSA-N azetidine-3-carboxylic acid Chemical compound OC(=O)C1CNC1 GFZWHAAOIVMHOI-UHFFFAOYSA-N 0.000 abstract 11
- JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 abstract 9
- 150000002148 esters Chemical class 0.000 abstract 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- NDUWNWVXAYLZSO-UHFFFAOYSA-N pyrrolidin-2-ol Chemical compound OC1CCCN1 NDUWNWVXAYLZSO-UHFFFAOYSA-N 0.000 abstract 3
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 abstract 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 abstract 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- 125000006231 alkoxy propyl group Chemical group 0.000 abstract 1
- 125000004848 alkoxyethyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004181 carboxyalkyl group Chemical group 0.000 abstract 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 229940125721 immunosuppressive agent Drugs 0.000 abstract 1
- 239000003018 immunosuppressive agent Substances 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 230000000877 morphologic effect Effects 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Chemical class 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- 150000003577 thiophenes Chemical class 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
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- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- 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]
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/155—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Immunology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Composiciones farmacéuticas que los contienen y usos como agentes inmunosupresores. Reivindicacion 1: Un compuesto seleccionado del grupo formado por tiofenos de la formula (1) en los que A representa -CH2CH2-, -CH= CH-, -NH-CH2- , -CH2-O-, o -CH2- NH-; R1 representa H, alquilo C1-5, alcoxi C1-5 o halogeno; R2 representa H, alquilo C1-5, alcoxi C1-5, trifluorometilo, trifluorometoxi, o halogeno; R3 representa 2,3-dihidroxipropilo, -CH2-(CH2)k-NR31R32, (ácido azetidin-3- carboxílico)-1-il- metilo, (alquil1-5 éster del ácido azetidin-3-carboxílico)-1-il-metilo, 2-[(-ácido azetidin-3-carboxílico)-1-il-etilo, 2-[(alquil1-5éster del ácido azetidin-3-carboxílico)-1-il]-etilo, 3-[(ácido azetidin-3-carboxílico)-1-il]-propilo, 3-[(alquil1- 5éster del ácido azetidin-3-carboxílico)-1-il]-propilo, (ácido pirrolidin-3-carboxílico)-1-il-metilo, (alquil1-5 éster del ácido pirrolidin-3-carboxílico)-1-il- metilo, (ácido pirrolidin-2-carboxílico)-1-il-metilo, (alquilC1-5 éster del ácido pirrolidin-2-carboxílico)-1-il-metilo, 2-[(-ácido pirrolidin-3- carboxílico)-1-il-etilo, 2-[(alquil1-5éster del ácido pirrolidin-3-carboxílico)-1-il]-etilo, 2-[(ácido pirrolidin-2-carboxílico)-1-il]-etilo, 2-[(alquil1-5éster del ácido pirrolidin-2- carboxílico)-1-il]-etilo, 3-[(ácido pirrolidin-3-carboxílico)-1-il]-propilo, 3-[(alquil1-5 éster del ácido pirrolidin-3-carboxílico)-1-il]-propilo, 3-[(ácido pirrolidin-2-carboxílico)-1-il]-propilo, 3-[(alquilC1-5 éster del ácido pirrolidin-2- carboxílico)-1-il]-propilo, -CH2-(CH2)n-COOH, -CH2-(CH2)n-CONR31R32, -CO-NHR31, 1-(1-(3-carboxi-azetidinil))-2-acetilo, 1-(1-(2- carboxi-pirrolidinil))-2-acetilo, 1-(1-(3-carboxi-pirrolidinil))-2-acetilo, 1-(1-(3-carboxi-azetidinil))-3-propionilo, 1- (1-(2-carboxi- pirrolidinil))-3-propionilo, 1-(1-(3-carboxi-pirrolidinil))-3-propionilo, -(CH2)nCH(OH)-CH2-NR31R32, 2-hidroxi-3-metoxi-propoxi, - OCH2-(CH2)m-NR31R32, 2-pirrolidin-1-il-etoxi, 3-pirrolidin-1-il-propoxi, 2-piperazin-1-il-etoxi, 2-[4- (alquilo C1-5)-piperazin-1-il]-etoxi, 2-[4-(2-hidroxi-etil)-piperazin-1-il]-etoxi, 3-piperazin-1-il-propoxi, 3-[4-(alquilo C1-5)-piperazin-1-il]-propoxi, 3-[4-(2-hidroxi-etil)- piperazin-1-il]-propoxi, 2-morfolin-4-il-etoxi, 3-morfolin-4-il-propoxi, 2- [(ácido azetidin-3-carboxílico)-1-il]-etoxi, 2-[(alquil1-5 éster del ácido azetidin-3-carboxílico)-1-il]-etoxi, 2-[(ácido pirrolidin-3-carboxílico)-1-il]-etoxi, 2-[(alquil 1-5 éster del ácido pirrolidin-3- carboxílico)-1-il]-etoxi, 2-[(ácido pirrolidin-2-carboxílico)-1-il]-etoxi, 2-[(alquil C1-5 éster del ácido pirrolidin-2-carboxílico)-1-il]-etoxi, 2-[(2-hidroxi-pirrolidin)-1-il]-etoxi, 2-[(3-hidroxi-pirrolidin)-1-il]-etoxi, 3-[(ácido azetidin-3-carboxílico)-1-il]-propoxi, 3-[(alquil 1- 5 éster del ácido azetidin-3-carboxílico)-1-il]-propoxi, 3-[(ácido pirrolidin-3-carboxílico)-1-il]-propoxi, 3-[(alquil1-5 éster del ácido pirrolidin-3- carboxílico)-1-il]-propoxi, 3-[(ácido pirrolidin-2-carboxílico)-1-il]-propoxi, 3-[(alquil 1-5 éster del ácido pirrolidin-2-carboxílico)-1-il]- propoxi, 3-[(2-hidroxi-pirrolidin)-1-il]-propoxi, 3-[(3-hidroxi-pirrolidin)-1-il]-propoxi, -O-CH2-CONR31R32, 1-(1-(3-carboxi-azetidinil))-1- oxo-2-etoxi, 1-(1-(ácido pirrolidin-2-carboxílico)-1-il)-1- oxo-2- etoxi, 1-(1-(ácido pirrolidin-3-carboxílico)-1-il)-1-oxo-2-etoxi, 3- carbamoil-propoxi, 3-(alquilo C1-5carbamoil)propoxi, 3-(2-hidroxietilcarbamoil)propoxi, -OCH2-CH(OH)-CH2-NR31R32, 3-[(ácido azetidin-3-carboxílico)-1-il]-2-hidroxipropoxi, 3- [(alquil1-5 éster del ácido azetidin-3-carboxílico)-1-il]-2-hidroxipropoxi, 2- hidroxi-3-[(ácido pirrolidin-3-carboxílico)-1-il]-propoxi, 2-hidroxi-3-[(alquil1-5 éster del ácido pirrolidin-3-carboxílico)-1-il]-propoxi, 2- hidroxi-3-[(ácido pirrolidin- 2-carboxílico)-1-il]-propoxi, 2-hidroxi-3-[(alquil C1-5 éster del ácido pirrolidin-2-carboxílico)-1-il]-propoxi, 2- hidroxi-3-[(2-hidroxi-pirrolidin)-1-il]-propoxi, 2-hidroxi-3-[(3-hidroxi-pirrolidin)-1-il]propoxi, 2-hidroxi-3-pirrolidin-1-il- propoxi, 2- hidroxi-3-piperazin-1-il-propoxi, 2-hidroxi-3-[4-(alquilo C1-5)-piperazin-1-il]-propoxi, 2-hidroxi-3-[4-(2-hidroxi-etil)-piperazin-1-il]- propoxi, 2-hidroxi-3-morfolin-4-il-propoxi, -NR31R32, -NHCO-R31, -CH2-(CH2)k-NHSO2R33, -(CH2)nCH(OH)- CH2-NHSO2R33, - OCH2-(CH2)m-NHSO2R33, -OCH2-CH(OH)-CH2-NHSO2R33, -CH2-(CH2)k-NHCOR34, -(CH2)nCH(OH)-CH2-NHCOR34, -OCH2-(CH2)m- NHCOR34, o -OCH2-CH(OH)-CH2-NHCOR34; R31 representa H, metilo, etilo, n-propilo, isopropilo, 2-hidroxietilo, 2-hidroxi-1- hidroximetil-etilo, 2-alcoxietilo C1-5, 3-hidroxipropilo, 3-alcoxipropilo C1-5, 2-aminoetilo, 2-(alquilamino C1-5)etilo, 2-(di-(alquilo C1-5) amino)etilo, carboximetilo, alquilo C1-5carboximetilo, 2-carboxietilo, 2-(alquilo C1-5carboxi)etilo; R32 representa H, metilo, o etilo; R33 representa metilo, etilo, propilo, isopropilo, butilo, 2-hidroxietilo, 2-metoxietilo, metilamino, etilamino, propilamino, isopropilamino, n- butilamino, o dimetilamino; R34 representa hidroximetilo, hidroxietilo, aminometilo, metilaminometilo, dimetilaminometilo, aminoetilo, 2-metilamino-etilo, o 2-dimetilamino-etilo; k representa el numero entero 1, 2 o 3;m representa el numero entero 1 o 2; n representa 0, 1, o 2; y R4 representa H, alquilo C1-5, metoxi o halogeno; y los isomeros de configuracion tales como enantiomeros opticamente puros, mezclas de enantiomeros tales como racematos, diastereomeros, mezclas de diastereomeros, racematos diastereoméricos, y mezclas de racematos diastereoméricos, como también sales y complejos de solventes de dichos compuestos, y formas morfologicas.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP2005003072 | 2005-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR053449A1 true AR053449A1 (es) | 2007-05-09 |
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| ARP060101134A AR053449A1 (es) | 2005-03-23 | 2006-03-22 | Derivados de tiofeno agonistas del receptor s1p1/edg1 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7846964B2 (es) |
| EP (1) | EP1863475B1 (es) |
| JP (1) | JP5063581B2 (es) |
| KR (1) | KR20080002850A (es) |
| CN (1) | CN101180050B (es) |
| AR (1) | AR053449A1 (es) |
| AT (1) | ATE523195T1 (es) |
| AU (1) | AU2006226022A1 (es) |
| BR (1) | BRPI0609665A2 (es) |
| CA (1) | CA2602478A1 (es) |
| ES (1) | ES2370791T3 (es) |
| IL (1) | IL186149A0 (es) |
| MX (1) | MX2007011669A (es) |
| NO (1) | NO20075297L (es) |
| RU (1) | RU2007138878A (es) |
| TW (1) | TW200716552A (es) |
| WO (1) | WO2006100635A2 (es) |
| ZA (1) | ZA200709086B (es) |
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| LT2885266T (lt) | 2012-08-17 | 2020-07-10 | Actelion Pharmaceuticals Ltd | (2z,5z)-5-(3-chlor-4-((r)-2,3-dihidroksipropoksi)benziliden)-2-(propilimino)-3-(o-tolil)tiazolidin-4-ono gamybos būdas ir šiame procese naudojamas tarpinis junginys |
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| US10111841B2 (en) | 2015-06-19 | 2018-10-30 | University Of South Florida | Stabilization of alcohol intoxication-induced cardiovascular instability |
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| WO1991015583A1 (en) | 1990-04-05 | 1991-10-17 | The American National Red Cross | A protein family related to immediate-early protein expressed by human endothelial cells during differentiation |
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| JP2002505868A (ja) | 1998-03-09 | 2002-02-26 | スミスクライン・ビーチャム・コーポレイション | ヒトＥＤＧ−１ｃポリヌクレオチドおよびポリペプチドおよびその使用法 |
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| WO2006010379A1 (en) | 2004-07-29 | 2006-02-02 | Actelion Pharmaceuticals Ltd. | Novel thiophene derivatives as immunosuppressive agents |
| KR101382733B1 (ko) * | 2005-03-23 | 2014-04-14 | 액테리온 파마슈티칼 리미티드 | 면역조절물질로서의 수첨 벤조(ｃ) 티오펜 유도체 |
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| AR057894A1 (es) | 2005-11-23 | 2007-12-26 | Actelion Pharmaceuticals Ltd | Derivados de tiofeno |
| US8178562B2 (en) | 2006-01-24 | 2012-05-15 | Actelion Pharmaceuticals, Ltd. | Pyridine derivatives |
-
2006
- 2006-03-20 AU AU2006226022A patent/AU2006226022A1/en not_active Abandoned
- 2006-03-20 KR KR1020077024188A patent/KR20080002850A/ko not_active Application Discontinuation
- 2006-03-20 WO PCT/IB2006/050853 patent/WO2006100635A2/en active Application Filing
- 2006-03-20 CN CN2006800174308A patent/CN101180050B/zh not_active Expired - Fee Related
- 2006-03-20 CA CA002602478A patent/CA2602478A1/en not_active Abandoned
- 2006-03-20 AT AT06727686T patent/ATE523195T1/de not_active IP Right Cessation
- 2006-03-20 US US11/909,440 patent/US7846964B2/en not_active Expired - Fee Related
- 2006-03-20 JP JP2008502542A patent/JP5063581B2/ja not_active Expired - Fee Related
- 2006-03-20 ES ES06727686T patent/ES2370791T3/es active Active
- 2006-03-20 BR BRPI0609665-4A patent/BRPI0609665A2/pt not_active IP Right Cessation
- 2006-03-20 EP EP06727686A patent/EP1863475B1/en active Active
- 2006-03-20 MX MX2007011669A patent/MX2007011669A/es not_active Application Discontinuation
- 2006-03-20 RU RU2007138878/04A patent/RU2007138878A/ru not_active Application Discontinuation
- 2006-03-22 TW TW095109924A patent/TW200716552A/zh unknown
- 2006-03-22 AR ARP060101134A patent/AR053449A1/es not_active Application Discontinuation
-
2007
- 2007-09-20 IL IL186149A patent/IL186149A0/en unknown
- 2007-10-17 NO NO20075297A patent/NO20075297L/no not_active Application Discontinuation
- 2007-10-22 ZA ZA200709086A patent/ZA200709086B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080002850A (ko) | 2008-01-04 |
| IL186149A0 (en) | 2008-01-20 |
| NO20075297L (no) | 2007-12-27 |
| EP1863475B1 (en) | 2011-09-07 |
| US7846964B2 (en) | 2010-12-07 |
| WO2006100635A2 (en) | 2006-09-28 |
| JP5063581B2 (ja) | 2012-10-31 |
| CN101180050A (zh) | 2008-05-14 |
| WO2006100635A3 (en) | 2007-01-18 |
| TW200716552A (en) | 2007-05-01 |
| EP1863475A2 (en) | 2007-12-12 |
| JP2008535815A (ja) | 2008-09-04 |
| AU2006226022A1 (en) | 2006-09-28 |
| ES2370791T3 (es) | 2011-12-22 |
| ATE523195T1 (de) | 2011-09-15 |
| ZA200709086B (en) | 2008-12-31 |
| MX2007011669A (es) | 2007-11-15 |
| CN101180050B (zh) | 2011-07-27 |
| BRPI0609665A2 (pt) | 2010-04-20 |
| US20080194670A1 (en) | 2008-08-14 |
| RU2007138878A (ru) | 2009-04-27 |
| CA2602478A1 (en) | 2006-09-28 |
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