ES2308127T3 - Nuevos derivados de acidos dicarboxilicos. - Google Patents
Nuevos derivados de acidos dicarboxilicos. Download PDFInfo
- Publication number
- ES2308127T3 ES2308127T3 ES04292517T ES04292517T ES2308127T3 ES 2308127 T3 ES2308127 T3 ES 2308127T3 ES 04292517 T ES04292517 T ES 04292517T ES 04292517 T ES04292517 T ES 04292517T ES 2308127 T3 ES2308127 T3 ES 2308127T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- alkyl
- sqbullet
- cyclopentane
- atom
- 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
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- 239000002253 acid Substances 0.000 title claims description 87
- 150000007513 acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- -1 polyfluoroalkyl Chemical group 0.000 claims abstract description 64
- 125000004429 atom Chemical group 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 33
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 29
- 150000002148 esters Chemical class 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 claims description 15
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 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 claims description 11
- 239000000556 agonist Substances 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- WDBRDCFUVVEIER-UHFFFAOYSA-N 3-[(4-octylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(CCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 WDBRDCFUVVEIER-UHFFFAOYSA-N 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004494 ethyl ester group Chemical group 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 210000004698 lymphocyte Anatomy 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims description 4
- 206010025135 lupus erythematosus Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- YGNJUQIUVOACOQ-UHFFFAOYSA-N 3-[(4-nonylphenyl)methylamino]-1-(2,2,2-trifluoroethylcarbamoyl)cyclopentane-1-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NCC(F)(F)F)(C(O)=O)CC1 YGNJUQIUVOACOQ-UHFFFAOYSA-N 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 3
- 208000009525 Myocarditis Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 208000003747 lymphoid leukemia Diseases 0.000 claims description 3
- 230000004048 modification Effects 0.000 claims description 3
- 238000012986 modification Methods 0.000 claims description 3
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- GAAVHFVDPMKSQB-UHFFFAOYSA-N 3-[(3-chloro-5-methoxy-4-octoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(OC)C(OCCCCCCCC)=C(Cl)C=C1CNC1CC(C(O)=O)(C(O)=O)CC1 GAAVHFVDPMKSQB-UHFFFAOYSA-N 0.000 claims description 2
- ABVSVEFDYXDWDL-UHFFFAOYSA-N 3-[(3-methoxy-5-methyl-4-octoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(OC)C(OCCCCCCCC)=C(C)C=C1CNC1CC(C(O)=O)(C(O)=O)CC1 ABVSVEFDYXDWDL-UHFFFAOYSA-N 0.000 claims description 2
- MRYMNMPUQASUMM-UHFFFAOYSA-N 3-[(4-butoxy-3-methoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(OC)C(OCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 MRYMNMPUQASUMM-UHFFFAOYSA-N 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000018 receptor agonist Substances 0.000 claims description 2
- 229940044601 receptor agonist Drugs 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 claims 2
- KRYDWUHYIWAFNC-UHFFFAOYSA-N 3-[(4-decoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid;1-(methylcarbamoyl)-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1.C1=CC(OCCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 KRYDWUHYIWAFNC-UHFFFAOYSA-N 0.000 claims 1
- JNHULPHBVGVKEY-UHFFFAOYSA-N 3-[(4-decylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid 3-[(4-nonylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C(CCCCCCCCC)C1=CC=C(CNC2CC(CC2)(C(=O)O)C(=O)O)C=C1.C(CCCCCCCC)C1=CC=C(CNC2CC(CC2)(C(=O)O)C(=O)O)C=C1 JNHULPHBVGVKEY-UHFFFAOYSA-N 0.000 claims 1
- 101000693265 Homo sapiens Sphingosine 1-phosphate receptor 1 Proteins 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000011541 reaction mixture Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 29
- 239000002904 solvent Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000012267 brine Substances 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 230000002829 reductive effect Effects 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
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- 239000002585 base Substances 0.000 description 10
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- 239000000284 extract Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 8
- DUYSYHSSBDVJSM-KRWOKUGFSA-N sphingosine 1-phosphate Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)COP(O)(O)=O DUYSYHSSBDVJSM-KRWOKUGFSA-N 0.000 description 8
- NQVRMIOCJAWYNB-UHFFFAOYSA-N 3-oxocyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC(=O)C1 NQVRMIOCJAWYNB-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- SQYXOCLWWBRSNN-UHFFFAOYSA-N 3-hydroxycyclopentane-1,1-dicarboxylic acid Chemical compound OC1CCC(C(O)=O)(C(O)=O)C1 SQYXOCLWWBRSNN-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
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- SWZTYAVBMYWFGS-UHFFFAOYSA-N fingolimod hydrochloride Chemical compound Cl.CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 SWZTYAVBMYWFGS-UHFFFAOYSA-N 0.000 description 5
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- 229910052708 sodium Inorganic materials 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- VRCHSUNFDQIMSO-UHFFFAOYSA-N 3-[(4-nonylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 VRCHSUNFDQIMSO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- LNYLDPYPCJIMLG-UHFFFAOYSA-N (4-nonylphenyl)methanamine Chemical compound CCCCCCCCCC1=CC=C(CN)C=C1 LNYLDPYPCJIMLG-UHFFFAOYSA-N 0.000 description 3
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- OVSQGRPUVXCGGX-UHFFFAOYSA-N 1-(methylcarbamoyl)-3-[(4-nonylphenyl)methylamino]cyclopentane-1-carboxylic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCC)=CC=C1CNC1CC(C(=O)NC)(C(O)=O)CC1 OVSQGRPUVXCGGX-UHFFFAOYSA-N 0.000 description 2
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- WHHSAXLIXILIBA-UHFFFAOYSA-N 3-[methyl-[(4-nonylphenyl)methyl]amino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(CCCCCCCCC)=CC=C1CN(C)C1CC(C(O)=O)(C(O)=O)CC1 WHHSAXLIXILIBA-UHFFFAOYSA-N 0.000 description 2
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/46—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C229/48—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups and carboxyl groups bound to carbon atoms of the same non-condensed ring
-
- 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
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Oncology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
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- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
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- Communicable Diseases (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04292517A EP1650186B1 (en) | 2004-10-22 | 2004-10-22 | Novel dicarboxylic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2308127T3 true ES2308127T3 (es) | 2008-12-01 |
Family
ID=34931473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04292517T Expired - Lifetime ES2308127T3 (es) | 2004-10-22 | 2004-10-22 | Nuevos derivados de acidos dicarboxilicos. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US20090264469A1 (https=) |
| EP (1) | EP1650186B1 (https=) |
| JP (1) | JP2008517897A (https=) |
| KR (1) | KR20070097418A (https=) |
| CN (1) | CN101107218A (https=) |
| AP (1) | AP2007004001A0 (https=) |
| AT (1) | ATE397582T1 (https=) |
| AU (1) | AU2005297138A1 (https=) |
| BR (1) | BRPI0516988A (https=) |
| CA (1) | CA2584610A1 (https=) |
| CY (1) | CY1108321T1 (https=) |
| DE (1) | DE602004014277D1 (https=) |
| DK (1) | DK1650186T3 (https=) |
| EA (1) | EA200700931A1 (https=) |
| ES (1) | ES2308127T3 (https=) |
| HR (1) | HRP20080431T3 (https=) |
| IL (1) | IL182678A0 (https=) |
| MX (1) | MX2007004847A (https=) |
| PL (1) | PL1650186T3 (https=) |
| PT (1) | PT1650186E (https=) |
| SI (1) | SI1650186T1 (https=) |
| WO (1) | WO2006043149A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2014653A1 (en) * | 2007-06-15 | 2009-01-14 | Bioprojet | Novel dicarboxylic acid derivatives as S1P1 receptor agonists |
| ES2360929T3 (es) * | 2007-09-20 | 2011-06-10 | Amgen Inc. | Derivados del ácido 1-(4-(4-bencilbenzamido)-bencil)azetidin-3-carboxílico y compuestos relacionados como moduladores del receptor s1p para el tratamiento de trastornos inmunitarios. |
| SI2291080T1 (sl) | 2008-05-14 | 2015-11-30 | The Scripps Research Institute | Novi modulatorji sfingosinskih fosfatnih receptorjev |
| EA019252B1 (ru) | 2008-07-23 | 2014-02-28 | Арена Фармасьютикалз, Инк. | ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ (1,2,3,4-ТЕТРАГИДРОЦИКЛОПЕНТА[b]ИНДОЛ-3-ИЛ)УКСУСНОЙ КИСЛОТЫ, ПРИМЕНИМЫЕ В ЛЕЧЕНИИ АУТОИММУННЫХ И ВОСПАЛИТЕЛЬНЫХ РАССТРОЙСТВ |
| SI2342205T1 (sl) | 2008-08-27 | 2016-09-30 | Arena Pharmaceuticals, Inc. | Substituirani triciklični kislinski derivati kot agonisti S1P1 receptorja, uporabni v zdravljenju avtoimunskih in vnetnih obolenj |
| SG10201906876PA (en) | 2010-01-27 | 2019-09-27 | Arena Pharm Inc | Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof |
| SG183416A1 (en) | 2010-03-03 | 2012-09-27 | Arena Pharm Inc | Processes for the preparation of s1p1 receptor modulators and crystalline forms thereof |
| KR101299512B1 (ko) * | 2011-04-19 | 2013-08-22 | 전북대학교산학협력단 | 스핑고신 1-포스페이트를 유효성분으로 함유하는 관절염 질환 치료 조성물 |
| MX386419B (es) | 2015-01-06 | 2025-03-18 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| EP3939965A1 (en) | 2015-06-22 | 2022-01-19 | Arena Pharmaceuticals, Inc. | Crystalline l-arginine salt of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclo-penta[b]indol-3-yl)acetic acid for use in sipi receptor-associated disorders |
| RU2615765C1 (ru) * | 2016-04-11 | 2017-04-11 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Уфимский государственный нефтяной технический университет" | Способ получения диалкилциклопент-3-ен-1,1-дикарбоксилата |
| WO2018151834A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of inflammatory bowel disease with extra-intestinal manifestations |
| MA47504A (fr) | 2017-02-16 | 2019-12-25 | Arena Pharm Inc | Composés et méthodes de traitement de l'angiocholite biliaire primitive |
| ES2987794T3 (es) | 2018-06-06 | 2024-11-18 | Arena Pharm Inc | Procedimientos de tratamiento de afecciones relacionadas con el receptor S1P1 |
| CN112955431A (zh) | 2018-09-06 | 2021-06-11 | 艾尼纳制药公司 | 可用于治疗自身免疫性病症和炎性病症的化合物 |
| WO2024064726A1 (en) * | 2022-09-21 | 2024-03-28 | Bristol-Myers Squibb Company | Process for the preparation of tert-butyl (2-azabicyclo[2.2.1]heptan-4-yl)carbamate and related compounds |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE599916A (https=) * | 1960-02-05 | |||
| US3325360A (en) * | 1963-11-25 | 1967-06-13 | Carter Prod Inc | Pyrimidine-di-one pharmaceutical compositions having anti-inflammatory activity |
| US4464531A (en) * | 1981-04-20 | 1984-08-07 | Sumitomo Chemical Company, Limited | 4-Carbamoylimidazolium-5-olate derivatives |
| US5482971A (en) * | 1993-10-01 | 1996-01-09 | American Cyanamid Company | Beta3 -adrenergic agents and their use in pharmaceutical compositions |
| US5480908A (en) * | 1993-12-13 | 1996-01-02 | American Cyanamid Company | β3 -adrenergic agents benzodioxole dicarboxylates and their use in pharmaceutical compositions |
| US5488064A (en) * | 1994-05-02 | 1996-01-30 | Bristol-Myers Squibb Company | Benzo 1,3 dioxole derivatives |
| WO1996001260A1 (en) * | 1994-07-01 | 1996-01-18 | Dainippon Pharmaceutical Co., Ltd. | Pyridonecarboxylic acid derivative, ester thereof, salt thereof, and intermediate for synthesis of these compounds |
| AU1619197A (en) * | 1996-02-07 | 1997-08-28 | Banyu Pharmaceutical Co., Ltd. | Cyclic amic acid derivatives |
| EP0801060A1 (en) * | 1996-04-09 | 1997-10-15 | Pfizer Inc. | Heterocyclic Beta-3 Adrenergenic Agonists |
| US5914339A (en) * | 1996-05-14 | 1999-06-22 | American Home Products Corporation | Substituted 1,3-benzodioxoles |
| JPH10245369A (ja) * | 1997-03-03 | 1998-09-14 | Ajinomoto Co Inc | セリン誘導体の製造方法 |
| US6124361A (en) * | 1997-12-31 | 2000-09-26 | Pfizer Inc | Bicyclo[3.1.0]hexanes and related compounds |
| WO1999061424A1 (en) * | 1998-05-26 | 1999-12-02 | Warner-Lambert Company | Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel |
| WO2000015604A1 (fr) * | 1998-09-11 | 2000-03-23 | Kyorin Pharmaceutical Co., Ltd. | Derives de diesters maloniques et leur procede d'obtention |
| JP4316787B2 (ja) * | 2000-01-11 | 2009-08-19 | 壽製薬株式会社 | エーテル又はアミド誘導体、その製法並びにそれを含有する糖尿病治療剤、 |
| GB0118238D0 (en) * | 2001-07-26 | 2001-09-19 | Smithkline Beecham Plc | Medicaments |
| ATE448193T1 (de) * | 2002-01-18 | 2009-11-15 | Merck & Co Inc | ßN-(BENZYL)AMINOALKYL CARBOXYLATE, PHOSPHINATE, PHOSPHONATE UND TETRAZOLE ALS EDG REZEPTORAGONISTENß |
| US20050070506A1 (en) * | 2002-01-18 | 2005-03-31 | Doherty George A. | Selective s1p1/edg1 receptor agonists |
| KR20080103117A (ko) * | 2002-09-24 | 2008-11-26 | 노파르티스 아게 | 탈수초성 장애의 치료에 있어서의 스핑고신-1-포스페이트 수용체 아고니스트 |
| WO2004035538A1 (en) * | 2002-10-15 | 2004-04-29 | Merck & Co., Inc. | Process for making azetidine-3-carboxylic acid |
| JP4516430B2 (ja) * | 2002-12-20 | 2010-08-04 | メルク・シャープ・エンド・ドーム・コーポレイション | １−（アミノ）インダン並びに（１，２−ジヒドロ−３−アミノ）−ベンゾフラン、ベンゾチオフェン及びインドール |
| TW200505834A (en) * | 2003-03-18 | 2005-02-16 | Sankyo Co | Sulfamide derivative and the pharmaceutical composition thereof |
-
2004
- 2004-10-22 AT AT04292517T patent/ATE397582T1/de active
- 2004-10-22 DE DE602004014277T patent/DE602004014277D1/de not_active Expired - Lifetime
- 2004-10-22 EP EP04292517A patent/EP1650186B1/en not_active Expired - Lifetime
- 2004-10-22 SI SI200430828T patent/SI1650186T1/sl unknown
- 2004-10-22 DK DK04292517T patent/DK1650186T3/da active
- 2004-10-22 ES ES04292517T patent/ES2308127T3/es not_active Expired - Lifetime
- 2004-10-22 PT PT04292517T patent/PT1650186E/pt unknown
- 2004-10-22 PL PL04292517T patent/PL1650186T3/pl unknown
-
2005
- 2005-10-18 KR KR1020077011042A patent/KR20070097418A/ko not_active Ceased
- 2005-10-18 EA EA200700931A patent/EA200700931A1/ru unknown
- 2005-10-18 MX MX2007004847A patent/MX2007004847A/es active IP Right Grant
- 2005-10-18 JP JP2007537410A patent/JP2008517897A/ja active Pending
- 2005-10-18 AP AP2007004001A patent/AP2007004001A0/xx unknown
- 2005-10-18 US US11/577,792 patent/US20090264469A1/en not_active Abandoned
- 2005-10-18 BR BRPI0516988-7A patent/BRPI0516988A/pt not_active IP Right Cessation
- 2005-10-18 AU AU2005297138A patent/AU2005297138A1/en not_active Abandoned
- 2005-10-18 CN CNA2005800405350A patent/CN101107218A/zh active Pending
- 2005-10-18 WO PCT/IB2005/003113 patent/WO2006043149A2/en not_active Ceased
- 2005-10-18 CA CA002584610A patent/CA2584610A1/en not_active Abandoned
-
2007
- 2007-04-19 IL IL182678A patent/IL182678A0/en unknown
-
2008
- 2008-09-03 HR HR20080431T patent/HRP20080431T3/xx unknown
- 2008-09-04 CY CY20081100957T patent/CY1108321T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008517897A (ja) | 2008-05-29 |
| WO2006043149A2 (en) | 2006-04-27 |
| CA2584610A1 (en) | 2006-04-27 |
| SI1650186T1 (sl) | 2008-12-31 |
| DK1650186T3 (da) | 2008-10-13 |
| PL1650186T3 (pl) | 2008-11-28 |
| WO2006043149A9 (en) | 2006-08-10 |
| DE602004014277D1 (de) | 2008-07-17 |
| AP2007004001A0 (en) | 2007-06-30 |
| EA200700931A1 (ru) | 2008-06-30 |
| US20090264469A1 (en) | 2009-10-22 |
| CN101107218A (zh) | 2008-01-16 |
| MX2007004847A (es) | 2007-09-27 |
| EP1650186B1 (en) | 2008-06-04 |
| PT1650186E (pt) | 2008-09-16 |
| IL182678A0 (en) | 2007-09-20 |
| KR20070097418A (ko) | 2007-10-04 |
| ATE397582T1 (de) | 2008-06-15 |
| HRP20080431T3 (en) | 2008-11-30 |
| WO2006043149A3 (en) | 2006-07-13 |
| EP1650186A1 (en) | 2006-04-26 |
| AU2005297138A1 (en) | 2006-04-27 |
| BRPI0516988A (pt) | 2008-09-30 |
| CY1108321T1 (el) | 2014-02-12 |
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