CA1335599C - 2-thioether-2-cyclopentenones - Google Patents

2-thioether-2-cyclopentenones

Info

Publication number: CA1335599C
Authority: CA; Canada
Prior art keywords: group; carbon atoms; substituted; hydroxy; cyclopentenone
Prior art date: 1988-04-19
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 - Fee Related

Application number

CA000616816A

Other languages

English (en)

Inventor

Satoshi Sugiura

Atsuo Hazato

Toru Minoshima

Yoshinori Kato

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Teijin Ltd

Original Assignee

Teijin Ltd

Priority date (The priority date 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 date listed.)

1988-04-19

Filing date

1994-02-03

Publication date

1995-05-16

1989-04-19 Priority claimed from CA000597198A external-priority patent/CA1332603C/fr

1994-02-03 Application filed by Teijin Ltd filed Critical Teijin Ltd

1995-05-16 Application granted granted Critical

1995-05-16 Publication of CA1335599C publication Critical patent/CA1335599C/fr

2009-04-19 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 77
125000001931 aliphatic group Chemical group 0.000 claims abstract description 34
125000001424 substituent group Chemical group 0.000 claims abstract description 31
125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 2
125000004432 carbon atom Chemical group C* 0.000 claims description 411
-1 2-substituted-2-cyclopentenones Chemical class 0.000 claims description 188
125000000217 alkyl group Chemical group 0.000 claims description 99
125000002252 acyl group Chemical group 0.000 claims description 95
125000004423 acyloxy group Chemical group 0.000 claims description 70
125000005843 halogen group Chemical group 0.000 claims description 69
125000003545 alkoxy group Chemical group 0.000 claims description 68
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 64
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 35
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 26
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 24
125000004430 oxygen atom Chemical group O* 0.000 claims description 24
125000002723 alicyclic group Chemical group 0.000 claims description 22
125000006239 protecting group Chemical group 0.000 claims description 14
150000001768 cations Chemical class 0.000 claims description 12
150000001875 compounds Chemical class 0.000 abstract description 65
230000000694 effects Effects 0.000 abstract description 16
230000011164 ossification Effects 0.000 abstract description 12
230000000259 anti-tumor effect Effects 0.000 abstract description 7
230000001133 acceleration Effects 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
239000000203 mixture Substances 0.000 description 99
238000006243 chemical reaction Methods 0.000 description 98
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 94
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
229920006395 saturated elastomer Polymers 0.000 description 82
239000000243 solution Substances 0.000 description 74
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 58
239000000460 chlorine Substances 0.000 description 58
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 56
239000011780 sodium chloride Substances 0.000 description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
238000005481 NMR spectroscopy Methods 0.000 description 35
239000012044 organic layer Substances 0.000 description 35
238000003786 synthesis reaction Methods 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
238000001228 spectrum Methods 0.000 description 33
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
230000015572 biosynthetic process Effects 0.000 description 32
239000012141 concentrate Substances 0.000 description 32
235000008504 concentrate Nutrition 0.000 description 32
238000007254 oxidation reaction Methods 0.000 description 30
238000010511 deprotection reaction Methods 0.000 description 29
229910000030 sodium bicarbonate Inorganic materials 0.000 description 29
235000017557 sodium bicarbonate Nutrition 0.000 description 29
150000007514 bases Chemical class 0.000 description 28
238000010898 silica gel chromatography Methods 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 26
150000002430 hydrocarbons Chemical group 0.000 description 26
BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 24
238000001914 filtration Methods 0.000 description 24
238000000034 method Methods 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
101150041968 CDC13 gene Proteins 0.000 description 21
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
FDSYWIWRUBJSDE-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hexan-2-one Chemical group O=C1CCC2OC12 FDSYWIWRUBJSDE-UHFFFAOYSA-N 0.000 description 19
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 19
125000004429 atom Chemical group 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
239000000047 product Substances 0.000 description 17
150000003573 thiols Chemical class 0.000 description 17
238000004519 manufacturing process Methods 0.000 description 16
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 16
239000002904 solvent Substances 0.000 description 16
239000007858 starting material Substances 0.000 description 15
229910052799 carbon Inorganic materials 0.000 description 14
238000001816 cooling Methods 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
229940086542 triethylamine Drugs 0.000 description 13
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 11
238000004587 chromatography analysis Methods 0.000 description 11
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000002253 acid Substances 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 9
235000019270 ammonium chloride Nutrition 0.000 description 9
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 9
239000007795 chemical reaction product Substances 0.000 description 9
239000000499 gel Substances 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
150000003180 prostaglandins Chemical class 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
229930195733 hydrocarbon Natural products 0.000 description 8
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
210000000963 osteoblast Anatomy 0.000 description 8
229940094443 oxytocics prostaglandins Drugs 0.000 description 8
JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 7
206010028980 Neoplasm Diseases 0.000 description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
201000011510 cancer Diseases 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 7
238000011282 treatment Methods 0.000 description 7
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
238000005406 washing Methods 0.000 description 7
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
238000005882 aldol condensation reaction Methods 0.000 description 6
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
238000001035 drying Methods 0.000 description 6
150000002170 ethers Chemical class 0.000 description 6
238000002955 isolation Methods 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 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
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 5
239000011575 calcium Substances 0.000 description 5
229910052791 calcium Inorganic materials 0.000 description 5
239000007810 chemical reaction solvent Substances 0.000 description 5
238000006297 dehydration reaction Methods 0.000 description 5
229960000443 hydrochloric acid Drugs 0.000 description 5
235000011167 hydrochloric acid Nutrition 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
239000010410 layer Substances 0.000 description 5
WZVKQPFLHKTDHB-UHFFFAOYSA-N methyl 7-[5-(3-hydroxyoct-1-enyl)-3-methylsulfanyl-2-oxocyclopent-3-en-1-ylidene]heptanoate Chemical compound CCCCCC(O)C=CC1C=C(SC)C(=O)C1=CCCCCCC(=O)OC WZVKQPFLHKTDHB-UHFFFAOYSA-N 0.000 description 5
239000007800 oxidant agent Substances 0.000 description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 5
239000000725 suspension Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
PTIQYLCDHGANTQ-UHFFFAOYSA-N 4-hydroxy-2-methylsulfanyl-4-(4-phenoxybutyl)cyclopent-2-en-1-one Chemical compound C1C(=O)C(SC)=CC1(O)CCCCOC1=CC=CC=C1 PTIQYLCDHGANTQ-UHFFFAOYSA-N 0.000 description 4
108091003079 Bovine Serum Albumin Proteins 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 4
102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000002246 antineoplastic agent Substances 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000010779 crude oil Substances 0.000 description 4
238000003379 elimination reaction Methods 0.000 description 4
238000000605 extraction Methods 0.000 description 4
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
XBCLKIMVIBFQBR-UHFFFAOYSA-N methyl 7-[5-[3-[tert-butyl(dimethyl)silyl]oxy-3-cyclopentylprop-1-enyl]-2-oxo-3-(3-phenylpropylsulfanyl)cyclopent-3-en-1-yl]-7-hydroxyhept-5-ynoate Chemical compound C1=C(SCCCC=2C=CC=CC=2)C(=O)C(C(O)C#CCCCC(=O)OC)C1C=CC(O[Si](C)(C)C(C)(C)C)C1CCCC1 XBCLKIMVIBFQBR-UHFFFAOYSA-N 0.000 description 4
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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 4
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 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
239000011574 phosphorus Substances 0.000 description 4
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
DERWZSGDVXRXGM-UHFFFAOYSA-N 4-hydroxy-2-methylsulfanyl-4-(4-phenoxybutyl)-5-(1,4,7-trihydroxyhept-2-enyl)cyclopent-2-en-1-one Chemical compound OCCCC(O)C=CC(O)C1C(=O)C(SC)=CC1(O)CCCCOC1=CC=CC=C1 DERWZSGDVXRXGM-UHFFFAOYSA-N 0.000 description 3
DHNDDRBMUVFQIZ-UHFFFAOYSA-N 4-hydroxycyclopent-2-en-1-one Chemical class OC1CC(=O)C=C1 DHNDDRBMUVFQIZ-UHFFFAOYSA-N 0.000 description 3
BRLQONSTWDAFKQ-FHLDBLRDSA-N 5-[(e)-4,7-dihydroxyhept-2-enylidene]-4-hydroxy-2-methylsulfinyl-4-(4-phenoxybutyl)cyclopent-2-en-1-one Chemical compound OCCCC(O)/C=C/C=C1C(=O)C(S(=O)C)=CC1(O)CCCCOC1=CC=CC=C1 BRLQONSTWDAFKQ-FHLDBLRDSA-N 0.000 description 3
TTYCPWCOWCUKKS-CROXYQROSA-N 5-[(z)-4,7-dihydroxyhept-2-enylidene]-4-hydroxy-2-methylsulfanyl-4-(4-phenoxybutyl)cyclopent-2-en-1-one Chemical compound OCCCC(O)\C=C/C=C1C(=O)C(SC)=CC1(O)CCCCOC1=CC=CC=C1 TTYCPWCOWCUKKS-CROXYQROSA-N 0.000 description 3
208000006386 Bone Resorption Diseases 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
206010011416 Croup infectious Diseases 0.000 description 3
GQHTUMJGOHRCHB-UHFFFAOYSA-N DBU Substances C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000024279 bone resorption Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
201000010549 croup Diseases 0.000 description 3
XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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 3
230000008030 elimination Effects 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
239000012091 fetal bovine serum Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
239000008187 granular material Substances 0.000 description 3
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
FOCVNHMTGPMKLU-UHFFFAOYSA-N methyl 4-[3-[2-hydroxy-4-methylsulfinyl-5-oxo-2-(4-phenoxybutyl)cyclopent-3-en-1-ylidene]propyl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1CCC=C1C(CCCCOC=2C=CC=CC=2)(O)C=C(S(C)=O)C1=O FOCVNHMTGPMKLU-UHFFFAOYSA-N 0.000 description 3
FPBKXLNCXRVERX-UHFFFAOYSA-N methyl 7-[5-(3-hydroxyoct-1-enyl)-3-methylsulfinyl-2-oxocyclopent-3-en-1-ylidene]heptanoate Chemical class CCCCCC(O)C=CC1C=C(S(C)=O)C(=O)C1=CCCCCCC(=O)OC FPBKXLNCXRVERX-UHFFFAOYSA-N 0.000 description 3
229910000343 potassium bisulfate Inorganic materials 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
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150000003208 punaglandins Chemical class 0.000 description 3
GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000003457 sulfones Chemical class 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
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BZLSFKOBFYCVJI-UHFFFAOYSA-N 2-methylsulfanyl-4-(4-phenoxybutyl)-4-trimethylsilyloxycyclopent-2-en-1-one Chemical compound C1C(=O)C(SC)=CC1(O[Si](C)(C)C)CCCCOC1=CC=CC=C1 BZLSFKOBFYCVJI-UHFFFAOYSA-N 0.000 description 2
NGAKSFFIMIROGV-UHFFFAOYSA-N 2-methylsulfanyl-4-(4-phenoxybutyl)-5-(1,4,7-trihydroxyhept-2-enyl)-4-trimethylsilyloxycyclopent-2-en-1-one Chemical compound OCCCC(O)C=CC(O)C1C(=O)C(SC)=CC1(O[Si](C)(C)C)CCCCOC1=CC=CC=C1 NGAKSFFIMIROGV-UHFFFAOYSA-N 0.000 description 2
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HOCBPFNPIRXDPH-UHFFFAOYSA-N 2-octyl-2-trimethylsilyloxy-6-oxabicyclo[3.1.0]hexan-4-one Chemical compound CCCCCCCCC1(O[Si](C)(C)C)CC(=O)C2OC12 HOCBPFNPIRXDPH-UHFFFAOYSA-N 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
WEKDXHVCIPYMTB-UHFFFAOYSA-N 4-(4-phenoxybutyl)-4-trimethylsilyloxycyclopent-2-en-1-one Chemical compound C=1C=CC=CC=1OCCCCC1(O[Si](C)(C)C)CC(=O)C=C1 WEKDXHVCIPYMTB-UHFFFAOYSA-N 0.000 description 2
FCTAYLPCJDKYBP-UHFFFAOYSA-N 4-[3-cyclohexyl-3-(oxan-2-yloxy)prop-1-enyl]cyclopent-2-en-1-one Chemical compound O1C(CCCC1)OC(C=CC1C=CC(C1)=O)C1CCCCC1 FCTAYLPCJDKYBP-UHFFFAOYSA-N 0.000 description 2
YFIMECUPDRKKPM-UHFFFAOYSA-N 4-butyl-5-(1-hydroxy-3-phenylprop-2-enyl)-2-(4-methylphenyl)sulfanylcyclopent-2-en-1-one Chemical compound O=C1C(C(O)C=CC=2C=CC=CC=2)C(CCCC)C=C1SC1=CC=C(C)C=C1 YFIMECUPDRKKPM-UHFFFAOYSA-N 0.000 description 2
URCMYHFMMPNXHN-UHFFFAOYSA-N 4-butyl-5-cinnamylidene-2-(4-methylphenyl)sulfinylcyclopent-2-en-1-one Chemical compound CCCCC1C=C(S(=O)C=2C=CC(C)=CC=2)C(=O)C1=CC=CC1=CC=CC=C1 URCMYHFMMPNXHN-UHFFFAOYSA-N 0.000 description 2
UFUNPQZWCBEECG-UHFFFAOYSA-N 4-butyl-5-cinnamylidene-2-(4-methylphenyl)sulfonylcyclopent-2-en-1-one Chemical compound CCCCC1C=C(S(=O)(=O)C=2C=CC(C)=CC=2)C(=O)C1=CC=CC1=CC=CC=C1 UFUNPQZWCBEECG-UHFFFAOYSA-N 0.000 description 2
XIFGEJSEHWHZOU-UHFFFAOYSA-N 4-hydroxy-2-methylsulfinyl-4-(4-phenoxybutyl)-5-(1,4,7-trihydroxyhept-2-enyl)cyclopent-2-en-1-one Chemical compound OCCCC(O)C=CC(O)C1C(=O)C(S(=O)C)=CC1(O)CCCCOC1=CC=CC=C1 XIFGEJSEHWHZOU-UHFFFAOYSA-N 0.000 description 2
AZQOQVQBAQVCNP-UHFFFAOYSA-N 4-hydroxy-2-methylsulfonyl-4-(4-phenoxybutyl)-5-(1,4,7-trihydroxyhept-2-enyl)cyclopent-2-en-1-one Chemical compound OCCCC(O)C=CC(O)C1C(=O)C(S(=O)(=O)C)=CC1(O)CCCCOC1=CC=CC=C1 AZQOQVQBAQVCNP-UHFFFAOYSA-N 0.000 description 2
FICKXTABCCDPFE-UHFFFAOYSA-N 4-hydroxy-5-(1-hydroxyoctyl)-4-(4-phenoxybutyl)-2-phenylsulfanylcyclopent-2-en-1-one Chemical compound C=1C(CCCCOC=2C=CC=CC=2)(O)C(C(O)CCCCCCC)C(=O)C=1SC1=CC=CC=C1 FICKXTABCCDPFE-UHFFFAOYSA-N 0.000 description 2
ICZROURJEMMEIQ-UHFFFAOYSA-N 4-hydroxy-5-[1-hydroxy-4-(4-methoxyphenyl)butyl]-2-methylsulfanyl-4-(4-phenoxybutyl)cyclopent-2-en-1-one Chemical compound C1=CC(OC)=CC=C1CCCC(O)C1C(CCCCOC=2C=CC=CC=2)(O)C=C(SC)C1=O ICZROURJEMMEIQ-UHFFFAOYSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
YVBGIEWSUACDJC-SANRMHCOSA-N 5-[(e)-4,7-bis[[tert-butyl(dimethyl)silyl]oxy]hept-2-enylidene]-2-methylsulfanyl-4-(4-phenoxybutyl)-4-trimethylsilyloxycyclopent-2-en-1-one Chemical compound CC(C)(C)[Si](C)(C)OCCCC(O[Si](C)(C)C(C)(C)C)/C=C/C=C1C(=O)C(SC)=CC1(O[Si](C)(C)C)CCCCOC1=CC=CC=C1 YVBGIEWSUACDJC-SANRMHCOSA-N 0.000 description 2
TTYCPWCOWCUKKS-FHLDBLRDSA-N 5-[(e)-4,7-dihydroxyhept-2-enylidene]-4-hydroxy-2-methylsulfanyl-4-(4-phenoxybutyl)cyclopent-2-en-1-one Chemical compound OCCCC(O)/C=C/C=C1C(=O)C(SC)=CC1(O)CCCCOC1=CC=CC=C1 TTYCPWCOWCUKKS-FHLDBLRDSA-N 0.000 description 2
PEMNXSXQLYUMMX-CROXYQROSA-N 5-[(z)-4,7-dihydroxyhept-2-enylidene]-4-hydroxy-2-methylsulfonyl-4-(4-phenoxybutyl)cyclopent-2-en-1-one Chemical compound OCCCC(O)\C=C/C=C1C(=O)C(S(=O)(=O)C)=CC1(O)CCCCOC1=CC=CC=C1 PEMNXSXQLYUMMX-CROXYQROSA-N 0.000 description 2
IOPXAOXUFZCFNR-UHFFFAOYSA-N 5-[4,7-bis[[tert-butyl(dimethyl)silyl]oxy]-1-hydroxyhept-2-enyl]-2-methylsulfanyl-4-(4-phenoxybutyl)-4-trimethylsilyloxycyclopent-2-en-1-one Chemical class CC(C)(C)[Si](C)(C)OCCCC(O[Si](C)(C)C(C)(C)C)C=CC(O)C1C(=O)C(SC)=CC1(O[Si](C)(C)C)CCCCOC1=CC=CC=C1 IOPXAOXUFZCFNR-UHFFFAOYSA-N 0.000 description 2
LKWVXIPHJDQRBI-UHFFFAOYSA-N 6-oxabicyclo[3.1.0]hex-1(5)-en-2-one Chemical class O=C1CCC2=C1O2 LKWVXIPHJDQRBI-UHFFFAOYSA-N 0.000 description 2
RFHSLNAEXXJWNJ-UHFFFAOYSA-N 7-(2-hydroxy-4-methylsulfanyl-2-octyl-5-oxocyclopent-3-en-1-ylidene)heptanoic acid Chemical compound CCCCCCCCC1(O)C=C(SC)C(=O)C1=CCCCCCC(O)=O RFHSLNAEXXJWNJ-UHFFFAOYSA-N 0.000 description 2
UIXANFPKWOVCSK-UHFFFAOYSA-N 9-[5-(3-hydroxyoct-1-enyl)-2-oxo-3-phenylsulfanylcyclopent-3-en-1-ylidene]nonanoic acid Chemical compound O=C1C(=CCCCCCCCC(O)=O)C(C=CC(O)CCCCC)C=C1SC1=CC=CC=C1 UIXANFPKWOVCSK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
ZBJJDYGJCNTNTH-UHFFFAOYSA-N Betahistine mesilate Chemical group CS(O)(=O)=O.CS(O)(=O)=O.CNCCC1=CC=CC=N1 ZBJJDYGJCNTNTH-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KDGWZSDBOZDUIS-UHFFFAOYSA-N CCCCC(C)C(=C=O)C(C=CC1C=CC(=O)C1=CC=CCCC)O Chemical compound CCCCC(C)C(=C=O)C(C=CC1C=CC(=O)C1=CC=CCCC)O KDGWZSDBOZDUIS-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
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 2
108010016766 KK 3 Proteins 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
ADMXEFKSNOIJEM-UHFFFAOYSA-N [2-(acetyloxymethyl)-6-hydroxy-6-[2-hydroxy-2-non-6-ynyl-5-oxo-4-(2-phenylethylsulfanyl)cyclopent-3-en-1-yl]hexyl] acetate Chemical compound O=C1C(C(O)CCCC(COC(C)=O)COC(C)=O)C(CCCCCC#CCC)(O)C=C1SCCC1=CC=CC=C1 ADMXEFKSNOIJEM-UHFFFAOYSA-N 0.000 description 2
CPRXFEQRVZVKAE-UHFFFAOYSA-N [4-acetyloxy-7-hydroxy-7-[2-hydroxy-4-methylsulfanyl-5-oxo-2-(4-phenoxybutyl)cyclopent-3-en-1-yl]hept-5-enyl] acetate Chemical compound CC(=O)OCCCC(OC(C)=O)C=CC(O)C1C(=O)C(SC)=CC1(O)CCCCOC1=CC=CC=C1 CPRXFEQRVZVKAE-UHFFFAOYSA-N 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
239000012752 auxiliary agent Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
ZPFKRQXYKULZKP-UHFFFAOYSA-N butylidene Chemical compound [CH2+]CC[CH-] ZPFKRQXYKULZKP-UHFFFAOYSA-N 0.000 description 2
125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
239000002775 capsule Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
BJTYVWDEMOWZFG-UHFFFAOYSA-N ethyl 9-[5-(3-hydroxyoct-1-enyl)-2-oxo-3-phenylsulfanylcyclopent-3-en-1-ylidene]nonanoate Chemical compound O=C1C(=CCCCCCCCC(=O)OCC)C(C=CC(O)CCCCC)C=C1SC1=CC=CC=C1 BJTYVWDEMOWZFG-UHFFFAOYSA-N 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000003906 humectant Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 2
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
ZRUYCSHWEQCTST-UHFFFAOYSA-N methyl 4-[3-[2-hydroxy-4-methylsulfanyl-5-oxo-2-(4-phenoxybutyl)cyclopent-3-en-1-ylidene]propyl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1CCC=C1C(CCCCOC=2C=CC=CC=2)(O)C=C(SC)C1=O ZRUYCSHWEQCTST-UHFFFAOYSA-N 0.000 description 2
ASROKNVJYHPOCD-UHFFFAOYSA-N methyl 4-[3-[2-hydroxy-4-methylsulfonyl-5-oxo-2-(4-phenoxybutyl)cyclopent-3-en-1-ylidene]propyl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1CCC=C1C(CCCCOC=2C=CC=CC=2)(O)C=C(S(C)(=O)=O)C1=O ASROKNVJYHPOCD-UHFFFAOYSA-N 0.000 description 2
JGPPTVPOBMNOTA-UHFFFAOYSA-N methyl 4-[3-hydroxy-3-[2-hydroxy-4-methylsulfanyl-5-oxo-2-(4-phenoxybutyl)cyclopent-3-en-1-yl]propyl]cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OC)CCC1CCC(O)C1C(CCCCOC=2C=CC=CC=2)(O)C=C(SC)C1=O JGPPTVPOBMNOTA-UHFFFAOYSA-N 0.000 description 2
BOSWNGSDWSXNTK-UHFFFAOYSA-N methyl 7-(2-hydroxy-2-methyl-4-methylsulfanyl-5-oxocyclopent-3-en-1-ylidene)heptanoate Chemical compound COC(=O)CCCCCC=C1C(=O)C(SC)=CC1(C)O BOSWNGSDWSXNTK-UHFFFAOYSA-N 0.000 description 2
LCICEGNQTVCQRQ-UHFFFAOYSA-N methyl 7-(2-hydroxy-4-methylsulfanyl-2-octyl-5-oxocyclopent-3-en-1-ylidene)heptanoate Chemical compound CCCCCCCCC1(O)C=C(SC)C(=O)C1=CCCCCCC(=O)OC LCICEGNQTVCQRQ-UHFFFAOYSA-N 0.000 description 2
IOEXSZXCZJEMSW-UHFFFAOYSA-N methyl 7-[2-(3,7-dimethyloctyl)-2-hydroxy-4-methylsulfanyl-5-oxocyclopent-3-en-1-yl]-7-hydroxyheptanoate Chemical compound COC(=O)CCCCCC(O)C1C(=O)C(SC)=CC1(O)CCC(C)CCCC(C)C IOEXSZXCZJEMSW-UHFFFAOYSA-N 0.000 description 2
SLAJWABCSXYHMM-UHFFFAOYSA-N methyl 7-[2-(3,7-dimethyloctyl)-2-hydroxy-4-methylsulfanyl-5-oxocyclopent-3-en-1-ylidene]heptanoate Chemical compound COC(=O)CCCCCC=C1C(=O)C(SC)=CC1(O)CCC(C)CCCC(C)C SLAJWABCSXYHMM-UHFFFAOYSA-N 0.000 description 2
AFLVMIHZCKNNJD-UHFFFAOYSA-N methyl 7-[2-(3-cyclohexyl-3-hydroxyprop-1-enyl)-2-hydroxy-4-methylsulfanyl-5-oxocyclopent-3-en-1-yl]-7-hydroxyhept-5-ynoate Chemical compound COC(=O)CCCC#CC(O)C1C(=O)C(SC)=CC1(O)C=CC(O)C1CCCCC1 AFLVMIHZCKNNJD-UHFFFAOYSA-N 0.000 description 2
PVMITUDWKIEWPR-UHFFFAOYSA-N methyl 7-[2-(3-cyclohexyl-3-hydroxyprop-1-enyl)-2-hydroxy-4-methylsulfinyl-5-oxocyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound COC(=O)CCCC#CC=C1C(=O)C(S(C)=O)=CC1(O)C=CC(O)C1CCCCC1 PVMITUDWKIEWPR-UHFFFAOYSA-N 0.000 description 2
FGRNPTZWDUESDT-UHFFFAOYSA-N methyl 7-[2-[3-(3,4-dimethoxyphenyl)propyl]-2-hydroxy-4-methylsulfanyl-5-oxocyclopent-3-en-1-yl]-7-hydroxyheptanoate Chemical compound COC(=O)CCCCCC(O)C1C(=O)C(SC)=CC1(O)CCCC1=CC=C(OC)C(OC)=C1 FGRNPTZWDUESDT-UHFFFAOYSA-N 0.000 description 2
CXDSIOXKIUYLJQ-UHFFFAOYSA-N methyl 7-[2-[3-(3,4-dimethoxyphenyl)propyl]-2-hydroxy-4-methylsulfanyl-5-oxocyclopent-3-en-1-ylidene]heptanoate Chemical compound COC(=O)CCCCCC=C1C(=O)C(SC)=CC1(O)CCCC1=CC=C(OC)C(OC)=C1 CXDSIOXKIUYLJQ-UHFFFAOYSA-N 0.000 description 2
KRQKGSUECAFDNI-UHFFFAOYSA-N methyl 7-[3-(benzenesulfinyl)-5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-2-oxocyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound C1=C(S(=O)C=2C=CC=CC=2)C(=O)C(=CC#CCCCC(=O)OC)C1C=CC(O)C1CCCC1 KRQKGSUECAFDNI-UHFFFAOYSA-N 0.000 description 2
JIEJTMVLLLNQFP-UHFFFAOYSA-N methyl 7-[3-(benzenesulfonyl)-5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-2-oxocyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound C1=C(S(=O)(=O)C=2C=CC=CC=2)C(=O)C(=CC#CCCCC(=O)OC)C1C=CC(O)C1CCCC1 JIEJTMVLLLNQFP-UHFFFAOYSA-N 0.000 description 2
HIXNQZOMCVXFGV-UHFFFAOYSA-N methyl 7-[3-[(4-chlorophenyl)methylsulfonyl]-5-(3-hydroxy-5-methylnon-1-enyl)-2-oxocyclopent-3-en-1-ylidene]hept-2-enoate Chemical compound O=C1C(=CCCCC=CC(=O)OC)C(C=CC(O)CC(C)CCCC)C=C1S(=O)(=O)CC1=CC=C(Cl)C=C1 HIXNQZOMCVXFGV-UHFFFAOYSA-N 0.000 description 2
BEZTWBFKPCYQBB-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-2-oxo-3-(3-phenylpropylsulfanyl)cyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound C1=C(SCCCC=2C=CC=CC=2)C(=O)C(=CC#CCCCC(=O)OC)C1C=CC(O)C1CCCC1 BEZTWBFKPCYQBB-UHFFFAOYSA-N 0.000 description 2
YPZYUJDTOSONHS-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-2-oxo-3-(3-phenylpropylsulfinyl)cyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound C1=C(S(=O)CCCC=2C=CC=CC=2)C(=O)C(=CC#CCCCC(=O)OC)C1C=CC(O)C1CCCC1 YPZYUJDTOSONHS-UHFFFAOYSA-N 0.000 description 2
GJDSXMVOOZDNJI-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-2-oxo-3-(3-phenylpropylsulfonyl)cyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound C1=C(S(=O)(=O)CCCC=2C=CC=CC=2)C(=O)C(=CC#CCCCC(=O)OC)C1C=CC(O)C1CCCC1 GJDSXMVOOZDNJI-UHFFFAOYSA-N 0.000 description 2
AMNJQXFOXUTJMS-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-2-oxo-3-phenylsulfanylcyclopent-3-en-1-yl]-7-hydroxyhept-5-ynoate Chemical compound C1=C(SC=2C=CC=CC=2)C(=O)C(C(O)C#CCCCC(=O)OC)C1C=CC(O)C1CCCC1 AMNJQXFOXUTJMS-UHFFFAOYSA-N 0.000 description 2
XEWWNIAFBMGOLW-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-3-(6-methoxy-6-oxohexyl)sulfanyl-2-oxocyclopent-3-en-1-yl]-7-hydroxyhept-5-ynoate Chemical compound COC(=O)CCCC#CC(O)C1C(=O)C(SCCCCCC(=O)OC)=CC1C=CC(O)C1CCCC1 XEWWNIAFBMGOLW-UHFFFAOYSA-N 0.000 description 2
TVPCMQXENXZXKN-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-3-(6-methoxy-6-oxohexyl)sulfanyl-2-oxocyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound COC(=O)CCCC#CC=C1C(=O)C(SCCCCCC(=O)OC)=CC1C=CC(O)C1CCCC1 TVPCMQXENXZXKN-UHFFFAOYSA-N 0.000 description 2
DRKUYGSQPVMWMD-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-3-(6-methoxy-6-oxohexyl)sulfinyl-2-oxocyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound COC(=O)CCCC#CC=C1C(=O)C(S(=O)CCCCCC(=O)OC)=CC1C=CC(O)C1CCCC1 DRKUYGSQPVMWMD-UHFFFAOYSA-N 0.000 description 2
XQHBVPYICLSZNS-UHFFFAOYSA-N methyl 7-[5-(3-cyclopentyl-3-hydroxyprop-1-enyl)-3-(6-methoxy-6-oxohexyl)sulfonyl-2-oxocyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound COC(=O)CCCC#CC=C1C(=O)C(S(=O)(=O)CCCCCC(=O)OC)=CC1C=CC(O)C1CCCC1 XQHBVPYICLSZNS-UHFFFAOYSA-N 0.000 description 2
NEIRTGAPDFXNOV-UHFFFAOYSA-N methyl 7-[5-(3-hydroxyoct-1-enyl)-3-methylsulfonyl-2-oxocyclopent-3-en-1-ylidene]heptanoate Chemical compound CCCCCC(O)C=CC1C=C(S(C)(=O)=O)C(=O)C1=CCCCCCC(=O)OC NEIRTGAPDFXNOV-UHFFFAOYSA-N 0.000 description 2
CSNOJYFUUWLEIS-UHFFFAOYSA-N methyl 7-hydroxy-7-(2-hydroxy-2-methyl-4-methylsulfanyl-5-oxocyclopent-3-en-1-yl)heptanoate Chemical compound COC(=O)CCCCCC(O)C1C(=O)C(SC)=CC1(C)O CSNOJYFUUWLEIS-UHFFFAOYSA-N 0.000 description 2
LABTWGUMFABVFG-UHFFFAOYSA-N methyl propenyl ketone Chemical class CC=CC(C)=O LABTWGUMFABVFG-UHFFFAOYSA-N 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
208000005368 osteomalacia Diseases 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
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239000008363 phosphate buffer Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 2
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125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
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LSTVYVUFIRLHJM-UHFFFAOYSA-N methyl 7-(2-octyl-5-oxocyclopent-3-en-1-ylidene)heptanoate Chemical compound CCCCCCCCC1C=CC(=O)C1=CCCCCCC(=O)OC LSTVYVUFIRLHJM-UHFFFAOYSA-N 0.000 description 1
FGFBXNQDHDQHDF-UHFFFAOYSA-N methyl 7-(3-methylsulfinyl-5-oct-1-enyl-2-oxocyclopent-3-en-1-ylidene)heptanoate Chemical compound CCCCCCC=CC1C=C(S(C)=O)C(=O)C1=CCCCCCC(=O)OC FGFBXNQDHDQHDF-UHFFFAOYSA-N 0.000 description 1
WFVZONHWMYFHFI-UHFFFAOYSA-N methyl 7-[2-(3-cyclohexyl-3-hydroxyprop-1-enyl)-2-hydroxy-4-methylsulfonyl-5-oxocyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound COC(=O)CCCC#CC=C1C(=O)C(S(C)(=O)=O)=CC1(O)C=CC(O)C1CCCCC1 WFVZONHWMYFHFI-UHFFFAOYSA-N 0.000 description 1
UVSWIDMWUUZSIU-UHFFFAOYSA-N methyl 7-[3-[(4-chlorophenyl)methylsulfinyl]-5-(3-hydroxy-5-methylnon-1-enyl)-2-oxocyclopent-3-en-1-ylidene]hept-2-enoate Chemical compound O=C1C(=CCCCC=CC(=O)OC)C(C=CC(O)CC(C)CCCC)C=C1S(=O)CC1=CC=C(Cl)C=C1 UVSWIDMWUUZSIU-UHFFFAOYSA-N 0.000 description 1
SAJKHYGOXRWFRW-UHFFFAOYSA-N methyl 7-[3-ethylsulfanyl-5-(3-hydroxyoct-1-enyl)-2-oxocyclopent-3-en-1-ylidene]heptanoate Chemical compound CCCCCC(O)C=CC1C=C(SCC)C(=O)C1=CCCCCCC(=O)OC SAJKHYGOXRWFRW-UHFFFAOYSA-N 0.000 description 1
XSVVLYRLORVOHO-UHFFFAOYSA-N methyl 7-[4-[3-[tert-butyl(dimethyl)silyl]oxy-3-cyclopentylprop-1-enyl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-yl]-7-hydroxyhept-5-ynoate Chemical compound C12OC2C(=O)C(C(O)C#CCCCC(=O)OC)C1C=CC(O[Si](C)(C)C(C)(C)C)C1CCCC1 XSVVLYRLORVOHO-UHFFFAOYSA-N 0.000 description 1
YHBYSSFJIULJTO-UHFFFAOYSA-N methyl 7-[4-[3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-2-oxo-6-oxabicyclo[3.1.0]hexan-3-yl]-7-hydroxyheptanoate Chemical compound O=C1C(C(O)CCCCCC(=O)OC)C(C=CC(O[Si](C)(C)C(C)(C)C)CCCCC)C2OC21 YHBYSSFJIULJTO-UHFFFAOYSA-N 0.000 description 1
WCOUMSLPZGICKW-UHFFFAOYSA-N methyl 7-[5-(3-tert-butyl-8-methyl-8-silyloxynon-1-enyl)-3-methylsulfanyl-2-oxocyclopent-3-en-1-yl]-7-hydroxyheptanoate Chemical compound CSC=1C(C(C(C1)C=CC(CCCCC(O[SiH3])(C)C)C(C)(C)C)C(CCCCCC(=O)OC)O)=O WCOUMSLPZGICKW-UHFFFAOYSA-N 0.000 description 1
RMDNHKUIPLUZNA-UHFFFAOYSA-N methyl 7-[5-[3-[tert-butyl(dimethyl)silyl]oxy-3-cyclopentylprop-1-enyl]-2-oxo-3-(3-phenylpropylsulfanyl)cyclopent-3-en-1-ylidene]hept-5-ynoate Chemical compound C1=C(SCCCC=2C=CC=CC=2)C(=O)C(=CC#CCCCC(=O)OC)C1C=CC(O[Si](C)(C)C(C)(C)C)C1CCCC1 RMDNHKUIPLUZNA-UHFFFAOYSA-N 0.000 description 1
DZJSWMPYGXAJNF-UHFFFAOYSA-N methyl 7-[5-[3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-ethylsulfanyl-2-oxocyclopent-3-en-1-yl]-7-hydroxyheptanoate Chemical compound CCCCCC(O[Si](C)(C)C(C)(C)C)C=CC1C=C(SCC)C(=O)C1C(O)CCCCCC(=O)OC DZJSWMPYGXAJNF-UHFFFAOYSA-N 0.000 description 1
VHJUPXXXSVRGFN-UHFFFAOYSA-N methyl 7-[5-[3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-methylsulfanyl-2-oxocyclopent-3-en-1-yl]-7-hydroxyheptanoate Chemical compound CCCCCC(O[Si](C)(C)C(C)(C)C)C=CC1C=C(SC)C(=O)C1C(O)CCCCCC(=O)OC VHJUPXXXSVRGFN-UHFFFAOYSA-N 0.000 description 1
DNOCCNMQOMUPPM-UHFFFAOYSA-N methyl 7-[5-[3-[tert-butyl(dimethyl)silyl]oxyoct-1-enyl]-3-methylsulfanyl-2-oxocyclopent-3-en-1-ylidene]heptanoate Chemical compound CCCCCC(O[Si](C)(C)C(C)(C)C)C=CC1C=C(SC)C(=O)C1=CCCCCCC(=O)OC DNOCCNMQOMUPPM-UHFFFAOYSA-N 0.000 description 1
DGORNOOLITTXGO-UHFFFAOYSA-N methyl 7-hydroxy-7-(2-hydroxy-4-methylsulfanyl-2-octyl-5-oxocyclopent-3-en-1-yl)heptanoate Chemical compound CCCCCCCCC1(O)C=C(SC)C(=O)C1C(O)CCCCCC(=O)OC DGORNOOLITTXGO-UHFFFAOYSA-N 0.000 description 1
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WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000011182 sodium carbonates Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
229940093633 tricaprin Drugs 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
229910001930 tungsten oxide Inorganic materials 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
229910001935 vanadium oxide Inorganic materials 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1

CA000616816A 1988-04-19 1994-02-03 2-thioether-2-cyclopentenones Expired - Fee Related CA1335599C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP9468788		1988-04-19
JP63-94687		1988-04-19
CA000597198A CA1332603C (fr)	1988-04-19	1989-04-19	2-cyclopentenones substituees en 2

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000597198A Division CA1332603C (fr)	1988-04-19	1989-04-19	2-cyclopentenones substituees en 2

Publications (1)

Publication Number	Publication Date
CA1335599C true CA1335599C (fr)	1995-05-16

Family

ID=25672631

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA000616816A Expired - Fee Related CA1335599C (fr)	1988-04-19	1994-02-03	2-thioether-2-cyclopentenones
CA000616815A Expired - Fee Related CA1335669C (fr)	1988-04-19	1994-02-03	2,3-epoxycyclopentanones

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CA000616815A Expired - Fee Related CA1335669C (fr)	1988-04-19	1994-02-03	2,3-epoxycyclopentanones

Country Status (1)

Country	Link
CA (2)	CA1335599C (fr)

1994
- 1994-02-03 CA CA000616816A patent/CA1335599C/fr not_active Expired - Fee Related
- 1994-02-03 CA CA000616815A patent/CA1335669C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA1335669C (fr)	1995-05-23

Legal Events

Date	Code	Title	Description
2009-05-19	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 20090519

Publication	Publication Date	Title
EP0159784B1 (fr)	1989-06-07	Analogues à la carbacycline
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EP0338796B1 (fr)	1993-03-10	2-Cyclopenténones 2-substituées
Rosen et al.	1985	Synthetic and biological studies of compactin and related compounds. 3. Synthesis of the hexalin portion of compactin
EP0106576B1 (fr)	1988-03-09	Composés cycliques à 5 membres, leur préparation, et application thérapeutique
CA1335599C (fr)	1995-05-16	2-thioether-2-cyclopentenones
EP0180399B1 (fr)	1992-05-20	4-Hydroxy-2-cyclopenténones antitumorales
US4788319A (en)	1988-11-29	Novel isocarbacyclins and processes for production thereof
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EP0065638B1 (fr)	1989-01-25	7-(4-substitués-cyclopent-2-en-1-on-2-yl)-hept-2-trans énoates substitués
US4983753A (en)	1991-01-08	Precursors and synthesis of di-(methyl)-16,16-(dimethyl)-11-alpha,15-alpha beta-dihydroxy-9-oxo-2,13-trans,trans-prostadienoates
JPH0141142B2 (fr)	1989-09-04
JP2503073B2 (ja)	1996-06-05	２―置換―２―シクロペンテノン類およびそれを含有する骨形成促進剤又は制ガン剤
US5283349A (en)	1994-02-01	2,6,7-trisubstituted-3-methylenebicyclo(3.3.0)-octanes, and process for production thereof
JPH0643360B2 (ja)	1994-06-08	４―ヒドロキシ―２―シクロペンテノン類及び薬剤組成物
US5532408A (en)	1996-07-02	α-chain-modified isocarbacyclins and process for the production thereof
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US5166369A (en)	1992-11-24	Precursors and synthesis of D1-(methyl)-16,16-(dimethyl)-11-alpha, 15-alpha, beta-dihydroxy-9-oxo-2,13,-trans, trans-prostadienoates
US4644079A (en)	1987-02-17	Precursors and synthesis of d1-(methyl)-16,16-(dimethyl)-11-alpha, 15-alpha, beta-dihydroxy-9-oxo-2,13,-trans, trans-prostadienoates
EP1094060B1 (fr)	2004-04-28	Procédé pour la préparation de dérivés de rétiférol
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