ES2772703T3 - Compuestos cíclicos - Google Patents
Compuestos cíclicos Download PDFInfo
- Publication number
- ES2772703T3 ES2772703T3 ES16729646T ES16729646T ES2772703T3 ES 2772703 T3 ES2772703 T3 ES 2772703T3 ES 16729646 T ES16729646 T ES 16729646T ES 16729646 T ES16729646 T ES 16729646T ES 2772703 T3 ES2772703 T3 ES 2772703T3
- Authority
- ES
- Spain
- Prior art keywords
- group
- compound
- mixture
- ethyl
- optionally substituted
- 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.)
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- 150000001923 cyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 125000001424 substituent group Chemical group 0.000 claims abstract description 96
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims abstract description 26
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 23
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 22
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- -1 (methoxymethyl) -1,4-dioxaspiro [4.5] dec-6-ene-7-carboxylate Chemical compound 0.000 claims description 367
- 239000003814 drug Substances 0.000 claims description 108
- 238000011282 treatment Methods 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 238000002512 chemotherapy Methods 0.000 claims description 23
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- UJLCQFMVTCPZLZ-UHFFFAOYSA-N hydroxymethyl 1,4-dioxaspiro[4.5]dec-6-ene-7-carboxylate Chemical compound OCOC(=O)C1=CC2(OCCO2)CCC1 UJLCQFMVTCPZLZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 14
- 208000004296 neuralgia Diseases 0.000 claims description 14
- 208000023275 Autoimmune disease Diseases 0.000 claims description 12
- 206010067125 Liver injury Diseases 0.000 claims description 11
- 208000021722 neuropathic pain Diseases 0.000 claims description 11
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 11
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims description 10
- 231100000753 hepatic injury Toxicity 0.000 claims description 10
- 238000011321 prophylaxis Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 208000014674 injury Diseases 0.000 claims description 5
- 208000028867 ischemia Diseases 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 345
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 207
- 239000000203 mixture Substances 0.000 description 163
- 229940079593 drug Drugs 0.000 description 102
- 239000000243 solution Substances 0.000 description 98
- 238000000034 method Methods 0.000 description 94
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 92
- 239000002904 solvent Substances 0.000 description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
- 230000002829 reductive effect Effects 0.000 description 71
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- 239000007788 liquid Substances 0.000 description 59
- 229920006395 saturated elastomer Polymers 0.000 description 58
- 239000011541 reaction mixture Substances 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 239000003795 chemical substances by application Substances 0.000 description 52
- 239000000284 extract Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 47
- 125000003118 aryl group Chemical group 0.000 description 42
- 238000010898 silica gel chromatography Methods 0.000 description 42
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
- 238000001816 cooling Methods 0.000 description 40
- 239000007787 solid Substances 0.000 description 40
- 239000011780 sodium chloride Substances 0.000 description 39
- 238000005160 1H NMR spectroscopy Methods 0.000 description 38
- 239000000126 substance Substances 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 37
- 235000019341 magnesium sulphate Nutrition 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- 238000004821 distillation Methods 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000003153 chemical reaction reagent Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000003112 inhibitor Substances 0.000 description 29
- 201000010099 disease Diseases 0.000 description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 102000008233 Toll-Like Receptor 4 Human genes 0.000 description 24
- 108010060804 Toll-Like Receptor 4 Proteins 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- 206010063837 Reperfusion injury Diseases 0.000 description 23
- 125000000623 heterocyclic group Chemical group 0.000 description 23
- 208000012947 ischemia reperfusion injury Diseases 0.000 description 23
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 21
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 20
- 235000017557 sodium bicarbonate Nutrition 0.000 description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 125000003396 thiol group Chemical group [H]S* 0.000 description 18
- 230000003287 optical 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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 14
- 238000000605 extraction Methods 0.000 description 14
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 230000037396 body weight Effects 0.000 description 12
- 238000002425 crystallisation Methods 0.000 description 12
- 150000001925 cycloalkenes Chemical class 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 230000011664 signaling Effects 0.000 description 12
- 208000002193 Pain Diseases 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 150000002430 hydrocarbons Chemical group 0.000 description 11
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 9
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 230000036407 pain Effects 0.000 description 9
- 239000000825 pharmaceutical preparation Substances 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 description 8
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 241000124008 Mammalia Species 0.000 description 8
- 239000002934 diuretic Substances 0.000 description 8
- 229940030606 diuretics Drugs 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 125000004185 ester group Chemical group 0.000 description 8
- DOOIGWCDOXNPLO-UHFFFAOYSA-N ethyl 2-propyloct-2-enoate Chemical compound CCCCCC=C(CCC)C(=O)OCC DOOIGWCDOXNPLO-UHFFFAOYSA-N 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 125000006413 ring segment Chemical group 0.000 description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 150000007522 mineralic acids Chemical class 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 150000003722 vitamin derivatives Chemical class 0.000 description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 6
- 239000005541 ACE inhibitor Substances 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 102100040247 Tumor necrosis factor Human genes 0.000 description 6
- 230000009471 action Effects 0.000 description 6
- 230000001154 acute effect Effects 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000001309 chloro group Chemical group Cl* 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 210000000056 organ Anatomy 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- 239000012279 sodium borohydride Substances 0.000 description 6
- 229910000033 sodium borohydride Inorganic materials 0.000 description 6
- 239000010902 straw Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
- 239000002841 Lewis acid Substances 0.000 description 5
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
- 206010040047 Sepsis Diseases 0.000 description 5
- 206010040070 Septic Shock Diseases 0.000 description 5
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 229940093915 gynecological organic acid Drugs 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000007517 lewis acids Chemical class 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 5
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 5
- 230000002265 prevention Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- VLGCZBWJGNCMIN-QMMMGPOBSA-N (1S)-7-chloro-2,3-dihydro-1H-inden-1-ol Chemical compound ClC=1C=CC=C2CC[C@@H](C=12)O VLGCZBWJGNCMIN-QMMMGPOBSA-N 0.000 description 4
- NXVDGDGFVCOMNT-UHFFFAOYSA-N 1-bromo-4-chloro-2,3-dihydro-1h-indene Chemical compound ClC1=CC=CC2=C1CCC2Br NXVDGDGFVCOMNT-UHFFFAOYSA-N 0.000 description 4
- LRMBFPBLLRVYBY-UHFFFAOYSA-N 1-bromo-7-chloro-2,3-dihydro-1H-indene Chemical compound BrC1CCC2=CC=CC(=C12)Cl LRMBFPBLLRVYBY-UHFFFAOYSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- 206010006895 Cachexia Diseases 0.000 description 4
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 4
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- 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 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/12—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
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- Organic Chemistry (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
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| US9611244B2 (en) * | 2015-05-08 | 2017-04-04 | Takeda Pharmaceutical Company Limited | Cyclic compounds |
| RU2742337C2 (ru) | 2016-09-09 | 2021-02-04 | Такеда Фармасьютикал Компани Лимитед | Циклическое соединение |
| FR3095755A1 (fr) * | 2019-05-10 | 2020-11-13 | Balmes Transplantation | Nouveaux médicaments cytoprotecteurs |
| CN114425054A (zh) * | 2022-01-20 | 2022-05-03 | 中国人民解放军军事科学院军事医学研究院 | 一种蛋白酶体抑制剂Bortezomib在抗辐射损伤中的用途 |
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| DK1063228T5 (da) | 1998-03-09 | 2009-06-15 | Takeda Pharmaceutical | Cycloalkenderivater, fremgangsmåde til fremstilling deraf og anvendelse deraf |
| WO2001010826A1 (en) | 1999-08-06 | 2001-02-15 | Takeda Chemical Industries, Ltd. | Substituted aromatic-ring compounds, process for producing the same, and use |
| JP2004002370A (ja) * | 2002-04-08 | 2004-01-08 | Takeda Chem Ind Ltd | 重症セプシス予防治療剤 |
| EP1495756A4 (en) * | 2002-04-08 | 2009-10-28 | Takeda Pharmaceutical | THERAPEUTIC AGENT FOR SEVERE SEPTIC STATE PREVENTION |
| US7935835B2 (en) * | 2005-09-14 | 2011-05-03 | Daiichi Sankyo Company, Limited | Substituted cycloalkene derivative |
| JP2008260760A (ja) * | 2007-03-12 | 2008-10-30 | Daiichi Sankyo Co Ltd | 置換シクロアルケン誘導体を含有する医薬組成物 |
| US20100135908A1 (en) * | 2008-12-02 | 2010-06-03 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Delivery devices for modulating inflammation |
| SG10201503402XA (en) | 2010-01-27 | 2015-06-29 | Takeda Pharmaceutical | Compounds for suppressing a peripheral nerve disorder induced by an anti-cancer agent |
| US9611244B2 (en) * | 2015-05-08 | 2017-04-04 | Takeda Pharmaceutical Company Limited | Cyclic compounds |
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2016
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- 2016-05-06 CN CN201680040064.1A patent/CN107835800B/zh active Active
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- 2016-05-06 WO PCT/JP2016/064204 patent/WO2016182036A1/en not_active Ceased
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| CA2985325C (en) | 2023-09-26 |
| UY36675A (es) | 2016-12-30 |
| EA201792469A1 (ru) | 2018-06-29 |
| CN107835800A (zh) | 2018-03-23 |
| EA033083B1 (ru) | 2019-08-30 |
| WO2016182036A1 (en) | 2016-11-17 |
| US20160326133A1 (en) | 2016-11-10 |
| US20170066737A1 (en) | 2017-03-09 |
| US9533966B2 (en) | 2017-01-03 |
| CA2985325A1 (en) | 2016-11-17 |
| EP3294706A1 (en) | 2018-03-21 |
| JP6718884B2 (ja) | 2020-07-08 |
| AR104539A1 (es) | 2017-07-26 |
| CN107835800B (zh) | 2019-11-26 |
| JP2018516875A (ja) | 2018-06-28 |
| US20160326102A1 (en) | 2016-11-10 |
| EP3294706B1 (en) | 2019-12-04 |
| BR112017023818A2 (pt) | 2018-07-31 |
| TW201704206A (zh) | 2017-02-01 |
| US9611244B2 (en) | 2017-04-04 |
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