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
Links
- 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
- 239000006196 drop Substances 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 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
- 239000007832 Na2SO4 Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229960000556 fingolimod Drugs 0.000 description 5
- SWZTYAVBMYWFGS-UHFFFAOYSA-N fingolimod hydrochloride Chemical compound Cl.CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 SWZTYAVBMYWFGS-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000001506 immunosuppresive effect Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 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
- 125000006239 protecting group Chemical group 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LNYLDPYPCJIMLG-UHFFFAOYSA-N (4-nonylphenyl)methanamine Chemical compound CCCCCCCCCC1=CC=C(CN)C=C1 LNYLDPYPCJIMLG-UHFFFAOYSA-N 0.000 description 3
- LVCWOFRWEVUMNY-UHFFFAOYSA-N 1-bromo-4-nonylbenzene Chemical compound CCCCCCCCCC1=CC=C(Br)C=C1 LVCWOFRWEVUMNY-UHFFFAOYSA-N 0.000 description 3
- MLPGFYQRKQHSJN-UHFFFAOYSA-N 4-nonylbenzaldehyde Chemical compound CCCCCCCCCC1=CC=C(C=O)C=C1 MLPGFYQRKQHSJN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 206010062016 Immunosuppression Diseases 0.000 description 3
- 239000003810 Jones reagent Substances 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000006978 adaptation Effects 0.000 description 3
- 230000008484 agonism Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 210000000170 cell membrane Anatomy 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000003599 food sweetener Nutrition 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000003018 immunosuppressive agent Substances 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- IUBGFHBFVBQPJJ-UHFFFAOYSA-N (3-bromo-5-methoxy-4-octoxyphenyl)methanamine Chemical compound CCCCCCCCOC1=C(Br)C=C(CN)C=C1OC IUBGFHBFVBQPJJ-UHFFFAOYSA-N 0.000 description 2
- YUJCYCDSWLIQRB-UHFFFAOYSA-N (3-bromo-5-methoxy-4-octoxyphenyl)methanol Chemical compound CCCCCCCCOC1=C(Br)C=C(CO)C=C1OC YUJCYCDSWLIQRB-UHFFFAOYSA-N 0.000 description 2
- PZRCOVWPEIONKP-UHFFFAOYSA-N (4-nonylphenyl)methanol Chemical compound CCCCCCCCCC1=CC=C(CO)C=C1 PZRCOVWPEIONKP-UHFFFAOYSA-N 0.000 description 2
- 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
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- PKILXMOKFDNUJX-UHFFFAOYSA-N 3-[(4-decylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(CCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 PKILXMOKFDNUJX-UHFFFAOYSA-N 0.000 description 2
- 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
- VNJOAFSMTCNNTO-UHFFFAOYSA-N 3-bromo-5-methoxy-4-octoxybenzaldehyde Chemical compound CCCCCCCCOC1=C(Br)C=C(C=O)C=C1OC VNJOAFSMTCNNTO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 206010018364 Glomerulonephritis Diseases 0.000 description 2
- 108010007979 Glycocholic Acid Proteins 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000034486 Multi-organ failure Diseases 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 101710155462 Sphingosine 1-phosphate receptor 2 Proteins 0.000 description 2
- 102100025749 Sphingosine 1-phosphate receptor 2 Human genes 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 150000003939 benzylamines Chemical class 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 230000036471 bradycardia Effects 0.000 description 2
- 208000006218 bradycardia Diseases 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229940125721 immunosuppressive agent Drugs 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 125000005956 isoquinolyl group Chemical group 0.000 description 2
- JJTUDXZGHPGLLC-UHFFFAOYSA-N lactide Chemical compound CC1OC(=O)C(C)OC1=O JJTUDXZGHPGLLC-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 2
- 239000007923 nasal drop Substances 0.000 description 2
- 229940100662 nasal drops Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- DHTAZFYWZBSXHJ-UHFFFAOYSA-N (4-octylphenyl)methanamine Chemical compound CCCCCCCCC1=CC=C(CN)C=C1 DHTAZFYWZBSXHJ-UHFFFAOYSA-N 0.000 description 1
- FQDIANVAWVHZIR-UPHRSURJSA-N (z)-1,4-dichlorobut-2-ene Chemical compound ClC\C=C/CCl FQDIANVAWVHZIR-UPHRSURJSA-N 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- JIVVSHXGCFTTTG-UHFFFAOYSA-N 1-(4-bromophenyl)nonan-1-one Chemical compound CCCCCCCCC(=O)C1=CC=C(Br)C=C1 JIVVSHXGCFTTTG-UHFFFAOYSA-N 0.000 description 1
- UWLHSHAHTBJTBA-UHFFFAOYSA-N 1-iodooctane Chemical compound CCCCCCCCI UWLHSHAHTBJTBA-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- AYSKYSTUUCZAJP-UHFFFAOYSA-N 3-[(3-bromo-5-methoxy-4-octoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(OC)C(OCCCCCCCC)=C(Br)C=C1CNC1CC(C(O)=O)(C(O)=O)CC1 AYSKYSTUUCZAJP-UHFFFAOYSA-N 0.000 description 1
- BNPUACXODXDNTR-UHFFFAOYSA-N 3-[(3-chloro-4-nonoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(Cl)C(OCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 BNPUACXODXDNTR-UHFFFAOYSA-N 0.000 description 1
- HKINKHTUTDKFAJ-UHFFFAOYSA-N 3-[(3-methoxy-4-nonoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(OC)C(OCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 HKINKHTUTDKFAJ-UHFFFAOYSA-N 0.000 description 1
- MCYRFAPPMOBYFK-UHFFFAOYSA-N 3-[(3-methoxy-4-octoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(OC)C(OCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 MCYRFAPPMOBYFK-UHFFFAOYSA-N 0.000 description 1
- BBKLEGNYBNRDLB-UHFFFAOYSA-N 3-[(4-decoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid;hydrochloride Chemical compound Cl.C1=CC(OCCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 BBKLEGNYBNRDLB-UHFFFAOYSA-N 0.000 description 1
- INCRZFYZMVTAAD-UHFFFAOYSA-N 3-[(4-hexoxy-3-methoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(OC)C(OCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 INCRZFYZMVTAAD-UHFFFAOYSA-N 0.000 description 1
- PWTJKPDDBOLTJA-UHFFFAOYSA-N 3-[(4-nonoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(OCCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 PWTJKPDDBOLTJA-UHFFFAOYSA-N 0.000 description 1
- FFFOSMLQSCXMJR-UHFFFAOYSA-N 3-[(4-octoxyphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(OCCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 FFFOSMLQSCXMJR-UHFFFAOYSA-N 0.000 description 1
- PIGUBXUVAAIKKA-UHFFFAOYSA-N 3-[(4-octylphenyl)methylamino]cyclopentane-1,1-dicarboxylic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCC)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 PIGUBXUVAAIKKA-UHFFFAOYSA-N 0.000 description 1
- FILCTBZVVHEKPS-UHFFFAOYSA-N 3-[[4-(4-phenylsulfanylbutoxy)phenyl]methylamino]cyclopentane-1,1-dicarboxylic acid;hydrochloride Chemical compound Cl.C1C(C(=O)O)(C(O)=O)CCC1NCC(C=C1)=CC=C1OCCCCSC1=CC=CC=C1 FILCTBZVVHEKPS-UHFFFAOYSA-N 0.000 description 1
- CXOAPWDYNMRFTD-UHFFFAOYSA-N 3-[[4-[4-(3-chloro-4-ethoxyphenyl)butoxy]phenyl]methylamino]cyclopentane-1,1-dicarboxylic acid;hydrochloride Chemical compound Cl.C1=C(Cl)C(OCC)=CC=C1CCCCOC(C=C1)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 CXOAPWDYNMRFTD-UHFFFAOYSA-N 0.000 description 1
- HFWUJOMAOUFLBC-UHFFFAOYSA-N 3-[[4-[4-(3-chloro-4-methoxyphenyl)butoxy]phenyl]methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CCCCOC(C=C1)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 HFWUJOMAOUFLBC-UHFFFAOYSA-N 0.000 description 1
- QEDQGKPRFHSFNI-UHFFFAOYSA-N 3-[[4-[4-(4-methoxyphenyl)butoxy]phenyl]methylamino]cyclopentane-1,1-dicarboxylic acid Chemical compound C1=CC(OC)=CC=C1CCCCOC(C=C1)=CC=C1CNC1CC(C(O)=O)(C(O)=O)CC1 QEDQGKPRFHSFNI-UHFFFAOYSA-N 0.000 description 1
- MHWGSNFJAURSIP-UHFFFAOYSA-N 3-[methyl-[(4-nonylphenyl)methyl]amino]cyclopentane-1,1-dicarboxylic acid;hydrochloride Chemical compound Cl.C1=CC(CCCCCCCCC)=CC=C1CN(C)C1CC(C(O)=O)(C(O)=O)CC1 MHWGSNFJAURSIP-UHFFFAOYSA-N 0.000 description 1
- JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-UHFFFAOYSA-N 0.000 description 1
- KLSHZDPXXKAHIJ-UHFFFAOYSA-N 3-bromo-4-hydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(Br)=C1O KLSHZDPXXKAHIJ-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical class [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical class [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101000693262 Homo sapiens Sphingosine 1-phosphate receptor 2 Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001248590 Isaria Species 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 101710155454 Sphingosine 1-phosphate receptor 1 Proteins 0.000 description 1
- 102100025750 Sphingosine 1-phosphate receptor 1 Human genes 0.000 description 1
- 101710155457 Sphingosine 1-phosphate receptor 3 Proteins 0.000 description 1
- 102100025747 Sphingosine 1-phosphate receptor 3 Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- RMHDLBZYPISZOI-UHFFFAOYSA-N borane;methylsulfanylmethane Chemical compound B.CSC RMHDLBZYPISZOI-UHFFFAOYSA-N 0.000 description 1
- YPWBYWNNJVSNPQ-UHFFFAOYSA-N borane;n,n-diethylaniline Chemical compound B.CCN(CC)C1=CC=CC=C1 YPWBYWNNJVSNPQ-UHFFFAOYSA-N 0.000 description 1
- KDKNBGWKECQREO-UHFFFAOYSA-N borane;n,n-diethylethanamine Chemical compound B.CCN(CC)CC KDKNBGWKECQREO-UHFFFAOYSA-N 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003684 cardiac depression Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940124301 concurrent medication Drugs 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940009976 deoxycholate Drugs 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 1
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 1
- YPTUAQWMBNZZRN-UHFFFAOYSA-N dimethylaminoboron Chemical compound [B]N(C)C YPTUAQWMBNZZRN-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 102000054996 human S1PR2 Human genes 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- ZTUJDPKOHPKRMO-UHFFFAOYSA-N hydron;2,2,2-trifluoroethanamine;chloride Chemical compound Cl.NCC(F)(F)F ZTUJDPKOHPKRMO-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229960001375 lactose Drugs 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 229960002366 magnesium silicate Drugs 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 238000006452 multicomponent reaction Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 238000009522 phase III clinical trial Methods 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229940068917 polyethylene glycols Drugs 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940033134 talc Drugs 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002992 thymic effect Effects 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- VCQWRGCXUWPSGY-UHFFFAOYSA-L zinc;2,2,2-trifluoroacetate Chemical compound [Zn+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F VCQWRGCXUWPSGY-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
-
- 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
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- 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
-
- 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07C229/02—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Obesity (AREA)
- Transplantation (AREA)
- Communicable Diseases (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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 (enExample) |
| EP (1) | EP1650186B1 (enExample) |
| JP (1) | JP2008517897A (enExample) |
| KR (1) | KR20070097418A (enExample) |
| CN (1) | CN101107218A (enExample) |
| AP (1) | AP2007004001A0 (enExample) |
| AT (1) | ATE397582T1 (enExample) |
| AU (1) | AU2005297138A1 (enExample) |
| BR (1) | BRPI0516988A (enExample) |
| CA (1) | CA2584610A1 (enExample) |
| CY (1) | CY1108321T1 (enExample) |
| DE (1) | DE602004014277D1 (enExample) |
| DK (1) | DK1650186T3 (enExample) |
| EA (1) | EA200700931A1 (enExample) |
| ES (1) | ES2308127T3 (enExample) |
| HR (1) | HRP20080431T3 (enExample) |
| IL (1) | IL182678A0 (enExample) |
| MX (1) | MX2007004847A (enExample) |
| PL (1) | PL1650186T3 (enExample) |
| PT (1) | PT1650186E (enExample) |
| SI (1) | SI1650186T1 (enExample) |
| WO (1) | WO2006043149A2 (enExample) |
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 |
| ATE505454T1 (de) * | 2007-09-20 | 2011-04-15 | Amgen Inc | 1-(4-(4-benzylbenzamid)-benzyl)-azetidin-3- carboxylsäurederivate und entsprechende verbindungen als s1p-rezeptor-modulatoren zur behandlung von immunerkrankungen |
| PL2291080T3 (pl) | 2008-05-14 | 2015-12-31 | Scripps Research Inst | Nowe modulatory receptorów sfingozyno-1-fosforanu |
| US8580841B2 (en) | 2008-07-23 | 2013-11-12 | Arena Pharmaceuticals, Inc. | Substituted 1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid derivatives useful in the treatment of autoimmune and inflammatory disorders |
| CN105816453B (zh) | 2008-08-27 | 2021-03-05 | 艾尼纳制药公司 | 用于治疗自身免疫性病症和炎性病症的作为s1p1受体激动剂的经取代的三环酸衍生物 |
| SG182610A1 (en) | 2010-01-27 | 2012-08-30 | 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 |
| CA2789480A1 (en) | 2010-03-03 | 2011-09-09 | Arena Pharmaceuticals, 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 |
| US11007175B2 (en) | 2015-01-06 | 2021-05-18 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| 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 |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| JP2020507610A (ja) | 2017-02-16 | 2020-03-12 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 腸管外症状を伴う炎症性腸疾患の治療のための化合物および方法 |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| CN119751336A (zh) | 2018-09-06 | 2025-04-04 | 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 |
| CA3264754A1 (en) * | 2022-09-21 | 2024-03-28 | Bristol Myers Squibb Co | PROCESS FOR THE PREPARATION OF TERT-BUTYL(2-AZABICYCLO[2.2.1]HEPTAN-4-YL)CARBAMATE AND ASSOCIATED COMPOUNDS |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE599916A (enExample) * | 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 |
| WO1997029078A1 (en) * | 1996-02-07 | 1997-08-14 | 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 |
| EP1082306A1 (en) * | 1998-05-26 | 2001-03-14 | 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 |
| AU2003216054B2 (en) * | 2002-01-18 | 2007-01-04 | Merck & Co., Inc. | Selective S1P1/Edg1 receptor agonists |
| JP4709488B2 (ja) * | 2002-01-18 | 2011-06-22 | メルク・シャープ・エンド・ドーム・コーポレイション | Ｅｄｇ受容体作動薬としてのＮ−（ベンジル）アミノアルキルカルボン酸化合物、ホスフィン酸化合物、ホスホン酸化合物およびテトラゾール類 |
| CN1708293A (zh) * | 2002-09-24 | 2005-12-14 | 诺瓦提斯公司 | 治疗脱髓鞘疾病的鞘氨醇－1－磷酸受体激动剂 |
| AU2003279915A1 (en) * | 2002-10-15 | 2004-05-04 | Merck And Co., Inc. | Process for making azetidine-3-carboxylic acid |
| EP1581509B1 (en) * | 2002-12-20 | 2011-01-19 | Merck Sharp & Dohme Corp. | 1-(amino)indanes as edg receptor agonists |
| TW200505834A (en) * | 2003-03-18 | 2005-02-16 | Sankyo Co | Sulfamide derivative and the pharmaceutical composition thereof |
-
2004
- 2004-10-22 SI SI200430828T patent/SI1650186T1/sl unknown
- 2004-10-22 DE DE602004014277T patent/DE602004014277D1/de not_active Expired - Lifetime
- 2004-10-22 AT AT04292517T patent/ATE397582T1/de active
- 2004-10-22 PT PT04292517T patent/PT1650186E/pt unknown
- 2004-10-22 DK DK04292517T patent/DK1650186T3/da active
- 2004-10-22 PL PL04292517T patent/PL1650186T3/pl unknown
- 2004-10-22 EP EP04292517A patent/EP1650186B1/en not_active Expired - Lifetime
- 2004-10-22 ES ES04292517T patent/ES2308127T3/es not_active Expired - Lifetime
-
2005
- 2005-10-18 KR KR1020077011042A patent/KR20070097418A/ko not_active Ceased
- 2005-10-18 WO PCT/IB2005/003113 patent/WO2006043149A2/en not_active Ceased
- 2005-10-18 AP AP2007004001A patent/AP2007004001A0/xx unknown
- 2005-10-18 MX MX2007004847A patent/MX2007004847A/es active IP Right Grant
- 2005-10-18 BR BRPI0516988-7A patent/BRPI0516988A/pt not_active IP Right Cessation
- 2005-10-18 EA EA200700931A patent/EA200700931A1/ru unknown
- 2005-10-18 US US11/577,792 patent/US20090264469A1/en not_active Abandoned
- 2005-10-18 AU AU2005297138A patent/AU2005297138A1/en not_active Abandoned
- 2005-10-18 CN CNA2005800405350A patent/CN101107218A/zh active Pending
- 2005-10-18 CA CA002584610A patent/CA2584610A1/en not_active Abandoned
- 2005-10-18 JP JP2007537410A patent/JP2008517897A/ja active Pending
-
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 |
|---|---|
| EA200700931A1 (ru) | 2008-06-30 |
| US20090264469A1 (en) | 2009-10-22 |
| WO2006043149A9 (en) | 2006-08-10 |
| EP1650186B1 (en) | 2008-06-04 |
| IL182678A0 (en) | 2007-09-20 |
| AP2007004001A0 (en) | 2007-06-30 |
| DE602004014277D1 (de) | 2008-07-17 |
| JP2008517897A (ja) | 2008-05-29 |
| CA2584610A1 (en) | 2006-04-27 |
| CY1108321T1 (el) | 2014-02-12 |
| AU2005297138A1 (en) | 2006-04-27 |
| BRPI0516988A (pt) | 2008-09-30 |
| WO2006043149A3 (en) | 2006-07-13 |
| MX2007004847A (es) | 2007-09-27 |
| DK1650186T3 (da) | 2008-10-13 |
| CN101107218A (zh) | 2008-01-16 |
| EP1650186A1 (en) | 2006-04-26 |
| WO2006043149A2 (en) | 2006-04-27 |
| PT1650186E (pt) | 2008-09-16 |
| ATE397582T1 (de) | 2008-06-15 |
| KR20070097418A (ko) | 2007-10-04 |
| SI1650186T1 (sl) | 2008-12-31 |
| HRP20080431T3 (en) | 2008-11-30 |
| PL1650186T3 (pl) | 2008-11-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2308127T3 (es) | Nuevos derivados de acidos dicarboxilicos. | |
| US8008315B2 (en) | Benzylether and benzylamino beta-secretase inhibitors for the treatment of alzheimer's disease | |
| JP5550650B2 (ja) | 細菌感染症処置に適用するための有機化合物 | |
| US7550481B2 (en) | Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of Alzheimer's disease | |
| US8030489B2 (en) | Ornithine derivative | |
| JP2008524154A (ja) | Ｃｃケモカイン受容体ｃｃｒ１のアンタゴニストとしてのピペリジン誘導体類及び抗−炎症剤としてのそれらの使用 | |
| US7432281B2 (en) | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same | |
| WO2013057322A1 (en) | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors | |
| CN102223797A (zh) | 金刚烷基苯甲酰胺化合物 | |
| RU2662817C2 (ru) | Соединение дикарбоновой кислоты | |
| US7449599B2 (en) | Phenyl carboxamide compounds useful as beta-secretase inhibitors for the treatment of alzheimer's disease | |
| TWI616435B (zh) | 苯基衍生物 | |
| JP2006515618A (ja) | 置換アルキルアミドピペリジン類 | |
| JP2006503090A (ja) | 新規なｎ−ヒドロキシチオウレア、ウレア及びアミド化合物とこれらからなる薬剤組成物 | |
| JP2025510512A (ja) | Ｌｐａ受容体活性と関連する状態の処置のための化合物および組成物 | |
| KR20050106421A (ko) | 카르복실산 화합물 | |
| JP2010512339A (ja) | Ａｍｐａ受容体増強剤 | |
| JP2024546138A (ja) | トリプタミンプロドラッグ | |
| TWI738162B (zh) | 稠合三環氘代衍生物及其組合物和用途 | |
| JPH08504441A (ja) | アザノルアダマンタン | |
| US20100035929A1 (en) | Unnatural dispyrin analogues, preparation and uses thereof | |
| TW201026691A (en) | Biaryl spiroaminooxazoline analogues as alpha2C adrenergic receptor modulators | |
| CN106317059A (zh) | 一种新的大麻素受体2（cb2）激动剂 | |
| EP0971916A1 (fr) | Derives de n-(arginyl)benzenesulfonamide et leur utilisation comme agents antithrombotiques |