JPH0210153B2 - - Google Patents

Info

Publication number: JPH0210153B2
Authority: JP; Japan
Prior art keywords: group; hydrogen atom; thia; prostaglandin; formula
Prior art date: 1982-12-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP57221995A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59112962A (ja

Inventor

Atsuo Hasato

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.)

1982-12-20

Filing date

1982-12-20

Publication date

1990-03-06

1982-12-20 Application filed by Teijin Ltd filed Critical Teijin Ltd

1982-12-20 Priority to JP57221995A priority Critical patent/JPS59112962A/ja

1983-11-08 Priority to EP83306792A priority patent/EP0112633A3/en

1984-06-29 Publication of JPS59112962A publication Critical patent/JPS59112962A/ja

1990-03-06 Publication of JPH0210153B2 publication Critical patent/JPH0210153B2/ja

Status Granted legal-status Critical Current

Links

125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 15
229940094443 oxytocics prostaglandins Drugs 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 9
238000010511 deprotection reaction Methods 0.000 claims description 9
231100000252 nontoxic Toxicity 0.000 claims description 9
230000003000 nontoxic effect Effects 0.000 claims description 9
239000004215 Carbon black (E152) Substances 0.000 claims description 8
229930195733 hydrocarbon Natural products 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
230000014509 gene expression Effects 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
150000001875 compounds Chemical class 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
FGOJCPKOOGIRPA-UHFFFAOYSA-N 1-o-tert-butyl 4-o-ethyl 5-oxoazepane-1,4-dicarboxylate Chemical compound CCOC(=O)C1CCN(C(=O)OC(C)(C)C)CCC1=O FGOJCPKOOGIRPA-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
150000003180 prostaglandins Chemical class 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
238000004809 thin layer chromatography Methods 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
239000000243 solution Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
150000007514 bases Chemical class 0.000 description 4
230000001766 physiological effect Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 3
-1 triethylsilyl Chemical group 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000005103 alkyl silyl group Chemical group 0.000 description 2
230000001093 anti-cancer Effects 0.000 description 2
230000000767 anti-ulcer Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000004071 biological effect Effects 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
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
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 2
238000000605 extraction Methods 0.000 description 2
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 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
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
239000012046 mixed solvent Substances 0.000 description 2
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 2
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 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000010898 silica gel chromatography Methods 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
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
108090000371 Esterases Proteins 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
239000004367 Lipase Substances 0.000 description 1
108090001060 Lipase Proteins 0.000 description 1
102000004882 Lipase Human genes 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
230000036772 blood pressure Effects 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
235000011116 calcium hydroxide Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
208000021822 hypotensive Diseases 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP57221995A 1982-12-20 1982-12-20 ５―チア―δ↑７―プロスタグランジンａ類およびその製造法 Granted JPS59112962A (ja)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
JP57221995A JPS59112962A (ja)	1982-12-20	1982-12-20	５―チア―δ↑７―プロスタグランジンａ類およびその製造法
EP83306792A EP0112633A3 (en)	1982-12-20	1983-11-08	Novel 5-thiaprostaglandin, process for production thereof, and pharmaceutical use thereof

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP57221995A JPS59112962A (ja)	1982-12-20	1982-12-20	５―チア―δ↑７―プロスタグランジンａ類およびその製造法

Related Child Applications (2)

Application Number	Title	Priority Date	Filing Date
JP1016332A Division JPH02167A (ja)	1989-01-27	1989-01-27	５‐チア‐△↑７‐プロスタグランジンｅ類およびその製造法
JP3036611A Division JPH06739B2 (ja)	1991-02-07	1991-02-07	５−チア−△７−プロスタグランジンｅ類およびその製造法

Publications (2)

Publication Number	Publication Date
JPS59112962A JPS59112962A (ja)	1984-06-29
JPH0210153B2 true JPH0210153B2 (pl)	1990-03-06

Family

ID=16775433

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57221995A Granted JPS59112962A (ja)	1982-12-20	1982-12-20	５―チア―δ↑７―プロスタグランジンａ類およびその製造法

Country Status (1)

Country	Link
JP (1)	JPS59112962A (pl)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58198466A (ja) *	1982-05-12	1983-11-18	Teijin Ltd	５−チアプロスタグランジン類およびその製造法

1982
- 1982-12-20 JP JP57221995A patent/JPS59112962A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS58198466A (ja) *	1982-05-12	1983-11-18	Teijin Ltd	５−チアプロスタグランジン類およびその製造法

Also Published As

Publication number	Publication date
JPS59112962A (ja)	1984-06-29

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US4554105A (en)	1985-11-19	Process for the preparation of 1-hydroxylated vitamin D compounds
CZ158290A3 (cs)	1999-06-16	Interfenylen-7-oxabicykloheptyl-substituované heterocykloamidové prostaglandinové analogy, použití těchto látek pro výrobu léčiv, farmaceutické prostředky obsahující tyto látky a postup přípravy těchto analogů
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PL208188B1 (pl)	2011-03-31	Sposób otrzymywania kalcypotriolu
CH619930A5 (pl)	1980-10-31
JPH0141142B2 (pl)	1989-09-04
JPH0210153B2 (pl)	1990-03-06
EP0065638B1 (en)	1989-01-25	Substituted 7-(4-substituted-cyclopent-2-en-1-on-2-yl)-hept-2-transenoates
JPS60169459A (ja)	1985-09-02	フエノキシプロスタトリエン酸誘導体の製造法
JP4598429B2 (ja)	2010-12-15	ジハロゲン化プロスタサイクリン類
JPH029585B2 (pl)	1990-03-02
JPH023793B2 (pl)	1990-01-24
JP2872468B2 (ja)	1999-03-17	イソカルバサイクリン誘導体、その製造法および光親和性標識法
JPH04330053A (ja)	1992-11-18	５−チア−△７−プロスタグランジンｅ類およびその製造法
JP3608843B2 (ja)	2005-01-12	ビタミンｄ３誘導体およびその製造法
JPH025746B2 (pl)	1990-02-05
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JPH02167A (ja)	1990-01-05	５‐チア‐△↑７‐プロスタグランジンｅ類およびその製造法
JPS62175496A (ja)	1987-08-01	ステロイド化合物及びその製造法
JPH0220616B2 (pl)	1990-05-10
JP2703392B2 (ja)	1998-01-26	イソカルバサイクリン類の製造法
JPS62242643A (ja)	1987-10-23	イソカルバサイクリン類の製造法
JPS6345385B2 (pl)	1988-09-09
JPH0660155B2 (ja)	1994-08-10	イソカルバサイクリン類
JPH026755B2 (pl)	1990-02-13