SU944502A3 - Способ получени производных простагландина - Google Patents

Способ получени производных простагландина Download PDF

Info

Publication number: SU944502A3
Authority: SU; USSR - Soviet Union
Prior art keywords: formula; prostaglandin; mixture; added; reaction
Prior art date: 1978-01-30

Application number

SU782719054A

Other languages

English (en)

Russian (ru)

Inventor

Еномото Сатору

Асано Киро

Тамура Хумио

Танака Хиромицу

Original Assignee

Куреха Кагаку Когио Кабусики Кайся (Фирма)

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.)

1978-01-31

Filing date

1978-01-30

Publication date

1982-07-15

1978-01-30 Application filed by Куреха Кагаку Когио Кабусики Кайся (Фирма) filed Critical Куреха Кагаку Когио Кабусики Кайся (Фирма)

1982-07-15 Application granted granted Critical

1982-07-15 Publication of SU944502A3 publication Critical patent/SU944502A3/ru

Links

150000003180 prostaglandins Chemical class 0.000 title claims abstract description 13
238000000034 method Methods 0.000 title claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
239000011230 binding agent Substances 0.000 claims abstract description 4
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical class [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 13
230000021736 acetylation Effects 0.000 claims description 6
238000006640 acetylation reaction Methods 0.000 claims description 6
-1 alkali metal salt Chemical class 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000003431 steroids Chemical class 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
229910019142 PO4 Inorganic materials 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 4
239000000463 material Substances 0.000 abstract description 2
239000003270 steroid hormone Substances 0.000 abstract 2
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 abstract 1
230000002159 abnormal effect Effects 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
125000005843 halogen group Chemical group 0.000 abstract 1
239000005556 hormone Substances 0.000 abstract 1
229940088597 hormone Drugs 0.000 abstract 1
238000002513 implantation Methods 0.000 abstract 1
239000003112 inhibitor Substances 0.000 abstract 1
230000005906 menstruation Effects 0.000 abstract 1
210000004291 uterus Anatomy 0.000 abstract 1
239000000047 product Substances 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 18
239000000243 solution Substances 0.000 description 18
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
150000001875 compounds Chemical class 0.000 description 6
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229960005309 estradiol Drugs 0.000 description 5
229930182833 estradiol Natural products 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
150000003378 silver Chemical class 0.000 description 4
ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 4
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
239000012264 purified product Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229910001961 silver nitrate Inorganic materials 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
POKRQUNDSGAZIA-IPDJLGJESA-N (2E)-7-[(1R,2S)-2-octylcyclopentyl]hepta-2,4-dienoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCC=C\C=C\C(O)=O POKRQUNDSGAZIA-IPDJLGJESA-N 0.000 description 1
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
FLFKKGCOSMKXGX-UHFFFAOYSA-N 2-triphenylphosphaniumylpentanoate Chemical compound CCCC(C([O-])=O)[P+](c1ccccc1)(c1ccccc1)c1ccccc1 FLFKKGCOSMKXGX-UHFFFAOYSA-N 0.000 description 1
OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
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 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229940124558 contraceptive agent Drugs 0.000 description 1
239000003433 contraceptive agent Substances 0.000 description 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000004720 fertilization Effects 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000027758 ovulation cycle Effects 0.000 description 1
229940072033 potash Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
YAGXZDADEJXXMM-UHFFFAOYSA-M potassium chloride hydrate Chemical compound [OH-].Cl.[K+] YAGXZDADEJXXMM-UHFFFAOYSA-M 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
150000003254 radicals Chemical group 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000013049 sediment Substances 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000004685 tetrahydrates Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/04—Drugs for genital or sexual disorders; Contraceptives for inducing labour or abortion; Uterotonics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0066—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa
- C07J1/007—Estrane derivatives substituted in position 17 beta not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0074—Esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
- C07J5/0007—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa
- C07J5/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond not substituted in position 17 alfa not substituted in position 16

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Gynecology & Obstetrics (AREA)
Pregnancy & Childbirth (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU782719054A 1978-01-31 1978-01-30 Способ получени производных простагландина SU944502A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP53009652A JPS5850236B2 (ja)	1978-01-31	1978-01-31	プロスタグランジン類↓−ステロイドホルモン結合体

Publications (1)

Publication Number	Publication Date
SU944502A3 true SU944502A3 (ru)	1982-07-15

Family

ID=11726136

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782719054A SU944502A3 (ru)	1978-01-31	1978-01-30	Способ получени производных простагландина

Country Status (11)

Country	Link
JP (1)	JPS5850236B2 (fr)
AT (1)	AT373268B (fr)
BE (1)	BE873380A (fr)
BG (1)	BG34611A3 (fr)
DD (1)	DD141261A5 (fr)
HU (1)	HU182517B (fr)
PL (1)	PL127780B1 (fr)
RO (1)	RO77375A (fr)
SU (1)	SU944502A3 (fr)
YU (1)	YU42174B (fr)
ZA (1)	ZA79305B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU190007B (en) *	1982-05-06	1986-08-28	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu	Process for producing new aromatic prostacylin analogues
WO2021220061A2 (fr) *	2020-05-01	2021-11-04	Ripple Therapeutics Corporation	Compositions hétérodimères et méthodes pour le traitement de troubles oculaires

1978
- 1978-01-30 SU SU782719054A patent/SU944502A3/ru active
- 1978-01-31 JP JP53009652A patent/JPS5850236B2/ja not_active Expired
1979
- 1979-01-05 AT AT0007979A patent/AT373268B/de not_active IP Right Cessation
- 1979-01-10 BE BE0/192818A patent/BE873380A/fr not_active IP Right Cessation
- 1979-01-24 ZA ZA79305A patent/ZA79305B/xx unknown
- 1979-01-29 RO RO7996423A patent/RO77375A/fr unknown
- 1979-01-29 HU HU79KU540A patent/HU182517B/hu not_active IP Right Cessation
- 1979-01-30 YU YU208/79A patent/YU42174B/xx unknown
- 1979-01-30 BG BG042307A patent/BG34611A3/xx unknown
- 1979-01-30 DD DD79210712A patent/DD141261A5/de not_active IP Right Cessation
- 1979-01-31 PL PL1979213122A patent/PL127780B1/pl unknown

Also Published As

Publication number	Publication date
PL127780B1 (en)	1983-11-30
HU182517B (en)	1984-01-30
DD141261A5 (de)	1980-04-23
ATA7979A (de)	1983-05-15
PL213122A1 (pl)	1979-10-08
YU42174B (en)	1988-06-30
RO77375A (fr)	1981-11-04
JPS5850236B2 (ja)	1983-11-09
YU20879A (en)	1983-01-21
BG34611A3 (en)	1983-10-15
BE873380A (fr)	1979-07-10
AT373268B (de)	1984-01-10
JPS54103858A (en)	1979-08-15
ZA79305B (en)	1980-01-30

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US3991106A (en)	1976-11-09	16-Ethers of 8-aza-9-dioxothia-11,12-seco-prostaglandins
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