JPH047755B2 - - Google Patents

Info

Publication number: JPH047755B2
Authority: JP; Japan
Prior art keywords: group; hydrogen atom; steroid compound; compound according; formula
Prior art date: 1986-01-30
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

Application number

JP1670586A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62175496A (ja

Inventor

Koji Tomimori

Toshio Tanaka

Seiji Kurozumi

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.)

1986-01-30

Filing date

1986-01-30

Publication date

1992-02-12

1986-01-30 Application filed by Teijin Ltd filed Critical Teijin Ltd

1986-01-30 Priority to JP1670586A priority Critical patent/JPS62175496A/ja

1987-08-01 Publication of JPS62175496A publication Critical patent/JPS62175496A/ja

1992-02-12 Publication of JPH047755B2 publication Critical patent/JPH047755B2/ja

Status Granted legal-status Critical Current

Links

-1 steroid compound Chemical class 0.000 claims description 40
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 14
229910052751 metal Inorganic materials 0.000 claims description 14
239000002184 metal Substances 0.000 claims description 14
125000004430 oxygen atom Chemical group O* 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 9
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical group [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 claims description 8
239000000203 mixture Substances 0.000 claims description 8
125000004185 ester group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
229910021555 Chromium Chloride Inorganic materials 0.000 claims description 5
229910052794 bromium Inorganic materials 0.000 claims description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
229910052797 bismuth Inorganic materials 0.000 claims description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
229910052718 tin Inorganic materials 0.000 claims description 3
229910052684 Cerium Inorganic materials 0.000 claims description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical group [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 2
MTCMFVTVXAOHNQ-UHFFFAOYSA-N ethyl 2-(bromomethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CBr MTCMFVTVXAOHNQ-UHFFFAOYSA-N 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
238000005809 transesterification reaction Methods 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
238000007259 addition reaction Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 11
239000000243 solution Substances 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
239000000047 product Substances 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
150000003431 steroids Chemical class 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
239000012043 crude product Substances 0.000 description 5
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
238000010898 silica gel chromatography Methods 0.000 description 5
QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical class C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
229910001882 dioxygen Inorganic materials 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
IJNDMZIDDKVXHR-MYEQSZOMSA-N 25-Hydroxyvitamin D3-26,23-lactone Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C/1C(CC[C@@H](O)C\1)=C)C)[C@@H]1C[C@@](C)(O)C(=O)O1 IJNDMZIDDKVXHR-MYEQSZOMSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 2
238000007664 blowing Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
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 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
239000005544 vitamin D3 metabolite Substances 0.000 description 2
WMYIVSWWSRCZFA-RWVJFQLJSA-N 1,25-Dihydroxyvitamin D3-26,23-lactone Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)[C@H]1C[C@@](C)(O)C(=O)O1 WMYIVSWWSRCZFA-RWVJFQLJSA-N 0.000 description 1
QLVKECUOHNDWOI-UHFFFAOYSA-N 2-oxo-1,3,2$l^{5}-diazaphosphonan-2-amine Chemical compound NP1(=O)NCCCCCCN1 QLVKECUOHNDWOI-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229930003316 Vitamin D Natural products 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000002798 bone marrow cell Anatomy 0.000 description 1
239000011612 calcitriol Substances 0.000 description 1
GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
BHQCQFFYRZLCQQ-OELDTZBJSA-M cholate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-M 0.000 description 1
229940099352 cholate Drugs 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical group [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002596 lactones Chemical group 0.000 description 1
JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
229910000476 molybdenum oxide Inorganic materials 0.000 description 1
238000005935 nucleophilic addition reaction Methods 0.000 description 1
239000005416 organic matter Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000007248 oxidative elimination reaction Methods 0.000 description 1
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000011135 tin Substances 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
150000003710 vitamin D derivatives Chemical class 0.000 description 1
235000005282 vitamin D3 Nutrition 0.000 description 1
239000011647 vitamin D3 Substances 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
229940021056 vitamin d3 Drugs 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)

JP1670586A 1986-01-30 1986-01-30 ステロイド化合物及びその製造法 Granted JPS62175496A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP1670586A JPS62175496A (ja)	1986-01-30	1986-01-30	ステロイド化合物及びその製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP1670586A JPS62175496A (ja)	1986-01-30	1986-01-30	ステロイド化合物及びその製造法

Publications (2)

Publication Number	Publication Date
JPS62175496A JPS62175496A (ja)	1987-08-01
JPH047755B2 true JPH047755B2 (pl)	1992-02-12

Family

ID=11923686

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1670586A Granted JPS62175496A (ja)	1986-01-30	1986-01-30	ステロイド化合物及びその製造法

Country Status (1)

Country	Link
JP (1)	JPS62175496A (pl)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101445655B1 (ko) *	2014-06-11	2014-10-06	범진시엔엘 주식회사	압전 스피커용 진동판 어셈블리 제조 방법

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6418640A (en) *	1987-07-14	1989-01-23	Kyocera Corp	Control system of image formation device
CA2114830C (en) *	1993-02-05	2000-06-06	Masayasu Tabe	Lactone compound and process of production thereof

1986
- 1986-01-30 JP JP1670586A patent/JPS62175496A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101445655B1 (ko) *	2014-06-11	2014-10-06	범진시엔엘 주식회사	압전 스피커용 진동판 어셈블리 제조 방법

Also Published As

Publication number	Publication date
JPS62175496A (ja)	1987-08-01

Legal Events

Date	Code	Title	Description
2005-02-12	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
JP3342047B2 (ja)	2002-11-05	ビタミンｄ化合物、該化合物の製造方法およびその中間体
US4554105A (en)	1985-11-19	Process for the preparation of 1-hydroxylated vitamin D compounds
US7645911B2 (en)	2010-01-12	Process for preparation of paricalcitol and intermediates thereof
WO1983004256A1 (en)	1983-12-08	METHOD FOR PREPARING 26,26,26,27,27,27-HEXAFLUORO-1alpha,25-DIHYDROXYCHOLESTEROL
JPH0662558B2 (ja)	1994-08-17	１α，７，８−トリヒドロキシビタミンＤ化合物
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JPS5823660A (ja)	1983-02-12	１α―ヒドロキシビタミンＤまたは１α―ヒドロキシ―プレビタミンＤ化合物の製造方法
HU207992B (en)	1993-07-28	Process for producing adduct-aldehydes as intermediates for producing vitamine d derivatives
US5886233A (en)	1999-03-23	Cyclohexanone derivatives, process for their production and intermediate products of the process
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US6255501B1 (en)	2001-07-03	Process for preparing antiosteoporotic agents
JP3715673B2 (ja)	2005-11-09	ビタミンｄ合成中間体の製造方法
JP3227263B2 (ja)	2001-11-12	光学活性オレフィンの製造方法
US5283345A (en)	1994-02-01	1β,7,8-trihydroxy vitamin D2, 1∘,7,8-trihydroxy vitamin D3 and their derivatives and method of manufacturing these chemicals
JPH07304732A (ja)	1995-11-21	含フッ素ビタミンｄ３類縁体
JP2743797B2 (ja)	1998-04-22	光学活性化合物の製法
JPH0672928A (ja)	1994-03-15	７−オクチン−１−エン誘導体およびその製造方法
JPH05246983A (ja)	1993-09-24	ビタミンｄ３誘導体及びその製造方法
JP2743798B2 (ja)	1998-04-22	光学活性化合物の製法
JP3391248B2 (ja)	2003-03-31	カルシトリオール中間体の製造法
JP3228486B2 (ja)	2001-11-12	ヒドロキシケトン誘導体およびその製造方法
JPH047757B2 (pl)	1992-02-12
JPH0873425A (ja)	1996-03-19	フッ素化ビタミンｄ誘導体および製造方法
JPH051278B2 (pl)	1993-01-07
JPH06157498A (ja)	1994-06-03	ビタミンｄ誘導体合成のための新規な中間体

JPH047755B2 - - Google Patents

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