JPS6092284A - ビスビベンジルジエ−テル誘導体 - Google Patents

ビスビベンジルジエ−テル誘導体

Info

Publication number: JPS6092284A
Authority: JP; Japan
Prior art keywords: formula; compound; solvent; group; city
Prior art date: 1983-10-25
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.): Granted

Application number

JP19973583A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0439467B2 (da

Inventor

Yoshinori Asakawa

義範浅川

Masao Toyoda

豊田　正夫

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.)

Otsuka Pharmaceutical Co Ltd

Original Assignee

Otsuka Pharmaceutical Co 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.)

1983-10-25

Filing date

1983-10-25

Publication date

1985-05-23

1983-10-25 Application filed by Otsuka Pharmaceutical Co Ltd filed Critical Otsuka Pharmaceutical Co Ltd

1983-10-25 Priority to JP19973583A priority Critical patent/JPS6092284A/ja

1985-05-23 Publication of JPS6092284A publication Critical patent/JPS6092284A/ja

1992-06-29 Publication of JPH0439467B2 publication Critical patent/JPH0439467B2/ja

Status Granted legal-status Critical Current

Links

125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 27
239000002904 solvent Substances 0.000 abstract description 13
238000000034 method Methods 0.000 abstract description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
239000003795 chemical substances by application Substances 0.000 abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
238000000605 extraction Methods 0.000 abstract description 4
238000000638 solvent extraction Methods 0.000 abstract description 4
125000004423 acyloxy group Chemical group 0.000 abstract description 3
241000196329 Marchantia polymorpha Species 0.000 abstract description 2
238000004440 column chromatography Methods 0.000 abstract description 2
230000000694 effects Effects 0.000 abstract description 2
231100000053 low toxicity Toxicity 0.000 abstract description 2
238000002360 preparation method Methods 0.000 abstract description 2
241001503396 Reboulia hemisphaerica Species 0.000 abstract 1
241001003158 Riccardia multifida Species 0.000 abstract 1
230000003327 cancerostatic effect Effects 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000010828 elution Methods 0.000 description 8
-1 isopanol Chemical class 0.000 description 7
230000000704 physical effect Effects 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
150000007514 bases Chemical class 0.000 description 5
238000000926 separation method Methods 0.000 description 5
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical group CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 5
235000016626 Agrimonia eupatoria Nutrition 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
241000196323 Marchantiophyta Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000009826 distribution Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000000401 methanolic extract Substances 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical group CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002994 raw material Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
FYEHYMARPSSOBO-UHFFFAOYSA-N Aurin Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)=C1C=CC(=O)C=C1 FYEHYMARPSSOBO-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000218691 Cupressaceae Species 0.000 description 1
208000007976 Ketosis Diseases 0.000 description 1
241000196322 Marchantia Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
230000003113 alkalizing effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Natural products CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004871 hexylcarbonyl group Chemical group C(CCCCC)C(=O)* 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000004140 ketosis Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000007769 metal material Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 description 1
125000005629 sialic acid group Chemical group 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

JP19973583A 1983-10-25 1983-10-25 ビスビベンジルジエ−テル誘導体 Granted JPS6092284A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP19973583A JPS6092284A (ja)	1983-10-25	1983-10-25	ビスビベンジルジエ−テル誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP19973583A JPS6092284A (ja)	1983-10-25	1983-10-25	ビスビベンジルジエ−テル誘導体

Publications (2)

Publication Number	Publication Date
JPS6092284A true JPS6092284A (ja)	1985-05-23
JPH0439467B2 JPH0439467B2 (da)	1992-06-29

Family

ID=16412751

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP19973583A Granted JPS6092284A (ja)	1983-10-25	1983-10-25	ビスビベンジルジエ−テル誘導体

Country Status (1)

Country	Link
JP (1)	JPS6092284A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005092328A1 (ja) *	2004-03-29	2005-10-06	Japan Health Sciences Foundation	Ｆｘｒ活性化化合物

1983
- 1983-10-25 JP JP19973583A patent/JPS6092284A/ja active Granted

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005092328A1 (ja) *	2004-03-29	2005-10-06	Japan Health Sciences Foundation	Ｆｘｒ活性化化合物
JPWO2005092328A1 (ja) *	2004-03-29	2008-02-07	財団法人ヒューマンサイエンス振興財団	Ｆｘｒ活性化化合物

Also Published As

Publication number	Publication date
JPH0439467B2 (da)	1992-06-29

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