SU667131A3 - Способ получени производных простановой кислоты или их эпимеров - Google Patents

Способ получени производных простановой кислоты или их эпимеров

Info

Publication number: SU667131A3
Authority: SU; USSR - Soviet Union
Prior art keywords: thereor; epimers; producing derivatives; prostanoic acids; prostanoic
Prior art date: 1972-11-08

Application number

SU731978255A

Other languages

English (en)

Inventor

Эрнст Гесс Ганс-Юрген

Кен Шаф Томас

Original Assignee

Пфайзер Инк. (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.)

1972-11-08

Filing date

1973-12-07

Publication date

1979-06-05

1973-12-07 Application filed by Пфайзер Инк. (Фирма) filed Critical Пфайзер Инк. (Фирма)

1979-06-05 Application granted granted Critical

1979-06-05 Publication of SU667131A3 publication Critical patent/SU667131A3/ru

Links

239000002253 acid Substances 0.000 title description 2
150000007513 acids Chemical class 0.000 title 1
-1 2-indanyl Chemical group 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
235000014121 butter Nutrition 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Description

3 irV при комнатной температуре в течение 18 ч с последующим концентрирова нием в роторном испарителе. Полученное масло хроматографируют на колонк с си йкагелем, элюиру смесью хлороформ-этилацетат . После элюировани менее пол рных примесей выдел ют 9с. 11(Л. , 15«А-триокси-15- (2-инданил) -цис-5-транс-13W -тр }норпростадиеновую кислоту, выход 156 мг (39%); т.пл. И4-115 с (этилацетат) . ИК-спектр (КВг), мк : 5,77, 10,25 В аналогичных услови х получают соединени общей формулы перечисленные в табл . 1 Соединени общей формулы перечисленные в табл. 2, получают подобным образом в виде масла. 14 Аналогичным образом получают соеинени общей формулы О где А - 2-инданил и X -5-тетразолил или CONHSOjCHj, в ИК-спектрб которых содержатс полосы 1740, 970 или 1740, 1720, 970 соответственно. Аналотачно синтезируют в виде масла МП эпимеры соединени общей формулы перечисленные в табл 3. В табл. 1 - табл. 3 МП и БМ обозначают менее и более пол рный эпимер при тонкослойной хроматографии в системе этилацетат - спирт. В аналогичных услови х получают также п-бифениловый эфир (2-инданил)-U ) -пентанор-РСРдд, т.пл. 134-135с, п-бифениловый эфир 15 (S)-2-(1,2,3,4-тетрагидронафтил ) -W -пентанор-РСЕ2, т.пл. 98-99с, и 2-дезкарбокси-2-Ттетразалил-5 )-15- (2-инДанил) -пентанор-PGF ., т.пл. 125-135с. Таблица 1

2-Инданил

2-(5,6-ДиметоксиИК-спектр сн т с использованием КВг,

1712,975

Масло

Т.пл. 110-112 0. Т. пл. 125-126°С,

Таблица 3

SU731978255A 1972-11-08 1973-12-07 Способ получени производных простановой кислоты или их эпимеров SU667131A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US30475072A	1972-11-08	1972-11-08

Publications (1)

Publication Number	Publication Date
SU667131A3 true SU667131A3 (ru)	1979-06-05

Family

ID=23177829

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU731978255A SU667131A3 (ru)	1972-11-08	1973-12-07	Способ получени производных простановой кислоты или их эпимеров
SU752182652A SU704456A3 (ru)	1972-11-08	1975-12-23	Способ получени -кетофосфонатов

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU752182652A SU704456A3 (ru)	1972-11-08	1975-12-23	Способ получени -кетофосфонатов

Country Status (20)

Country	Link
JP (1)	JPS5714347B2 (ru)
AT (1)	AT345999B (ru)
BE (1)	BE807046A (ru)
CA (1)	CA1033727A (ru)
CH (1)	CH593930A5 (ru)
DE (1)	DE2355731C3 (ru)
DK (1)	DK143499C (ru)
ES (3)	ES420386A1 (ru)
FI (1)	FI58912C (ru)
FR (3)	FR2205338B1 (ru)
GB (1)	GB1456838A (ru)
IE (1)	IE40043B1 (ru)
IL (2)	IL50310A (ru)
IN (1)	IN139265B (ru)
NL (1)	NL7315307A (ru)
NO (2)	NO143663C (ru)
PH (2)	PH13261A (ru)
SE (4)	SE412229B (ru)
SU (2)	SU667131A3 (ru)
ZA (1)	ZA738595B (ru)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1431561A (en) *	1973-01-31	1976-04-07	Ici Ltd	Cyclopentane derivatives
US3929862A (en) *	1974-01-08	1975-12-30	Upjohn Co	Substituted tolylesters of PGF{HD 2{B {60
JPS5823393B2 (ja) *	1974-03-14	1983-05-14	オノヤクヒンコウギヨウカブシキガイシヤ	プロスタグランジンルイジカゴウブツノセイゾウホウホウ
US4028396A (en) *	1975-07-02	1977-06-07	American Cyanamid Company	16,16-Spirocycloalkyl prostaglandin derivatives
US4074063A (en) *	1976-02-11	1978-02-14	Miles Laboratories, Inc.	Bicycloalkyl derivatives of prostaglandins
NZ183136A (en) *	1976-02-11	1978-11-13	Miles Lab	Monospiroalkyl derivatives of prostaclandis and pharmaceutical compositions
US4404372A (en) *	1977-06-13	1983-09-13	Pfizer Inc.	15-Substituted-ω-pentanorprostaglandin derivatives
DE2753995A1 (de) *	1977-12-03	1979-06-07	Bayer Ag	Neue bicycloalkenyl-prostaglandine und verfahren zu ihrer herstellung
JP2001515882A (ja) *	1997-09-09	2001-09-25	ザプロクターアンドギャンブルカンパニー	Ｆｐアゴニストとして有用な、芳香族のあるｃ１６〜ｃ２０が置換されたテトラヒドロプロスタグランジン類
IL134840A0 (en) *	1997-09-09	2001-05-20	Procter & Gamble	Aromatic c16-c20-substituted tetrahydro prostaglandins useful as fp agonists
DE69832513T2 (de) *	1997-09-09	2006-07-13	Duke University	Aromatische c16-c20-substituierte tetrahydro-prostaglandinen verwendbar wie fp agoniste
WO2000051980A1 (en) *	1999-03-05	2000-09-08	The Procter & Gamble Company	C16 unsaturated fp-selective prostaglandins analogs
US20020037914A1 (en)	2000-03-31	2002-03-28	Delong Mitchell Anthony	Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins
US20020013294A1 (en)	2000-03-31	2002-01-31	Delong Mitchell Anthony	Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives
US20020172693A1 (en)	2000-03-31	2002-11-21	Delong Michell Anthony	Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
ES2326558T3 (es) *	2007-11-28	2009-10-14	Bauer Maschinen Gmbh	Torno.
US8623918B2 (en)	2008-10-29	2014-01-07	Novaer Holdings, Inc.	Amino acid salts of prostaglandins
US8722739B2 (en)	2008-10-29	2014-05-13	Novaer Holdings, Inc.	Amino acid salts of prostaglandins
US20230097470A1 (en) *	2021-08-23	2023-03-30	Chirogate International Inc.	Processes and intermediates for the preparations of carboprost and carboprost tromethamine, and carboprost tromethamine prepared therefrom

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4864073A (ru) *	1971-04-30	1973-09-05

1973
- 1973-11-05 IL IL50310A patent/IL50310A/en unknown
- 1973-11-05 IL IL43571A patent/IL43571A/en unknown
- 1973-11-06 SE SE7315074A patent/SE412229B/xx unknown
- 1973-11-08 DE DE2355731A patent/DE2355731C3/de not_active Expired
- 1973-11-08 CA CA185,366A patent/CA1033727A/en not_active Expired
- 1973-11-08 ZA ZA738595A patent/ZA738595B/xx unknown
- 1973-11-08 NL NL7315307A patent/NL7315307A/xx not_active Application Discontinuation
- 1973-11-08 GB GB5199773A patent/GB1456838A/en not_active Expired
- 1973-11-08 JP JP12584373A patent/JPS5714347B2/ja not_active Expired
- 1973-11-08 IE IE2014/73A patent/IE40043B1/xx unknown
- 1973-11-08 FR FR7339758A patent/FR2205338B1/fr not_active Expired
- 1973-11-08 NO NO4294/73A patent/NO143663C/no unknown
- 1973-11-08 BE BE1005488A patent/BE807046A/xx unknown
- 1973-11-08 PH PH15197A patent/PH13261A/en unknown
- 1973-11-08 FI FI3455/73A patent/FI58912C/fi active
- 1973-11-08 DK DK603373A patent/DK143499C/da active
- 1973-11-08 CH CH1570773A patent/CH593930A5/xx not_active IP Right Cessation
- 1973-11-08 AT AT941073A patent/AT345999B/de not_active IP Right Cessation
- 1973-11-09 ES ES420386A patent/ES420386A1/es not_active Expired
- 1973-11-23 IN IN2583/CAL/73A patent/IN139265B/en unknown
- 1973-12-07 SU SU731978255A patent/SU667131A3/ru active
1974
- 1974-10-07 NO NO743616A patent/NO144385C/no unknown
1975
- 1975-12-23 SU SU752182652A patent/SU704456A3/ru active
1976
- 1976-01-16 ES ES444398A patent/ES444398A1/es not_active Expired
- 1976-01-29 FR FR7602433A patent/FR2286147A1/fr active Granted
- 1976-01-29 FR FR7602434A patent/FR2291200A1/fr active Granted
- 1976-05-25 PH PH18469A patent/PH13320A/en unknown
- 1976-11-03 SE SE7612261A patent/SE7612261L/xx unknown
- 1976-11-03 SE SE7612262A patent/SE7612262L/xx not_active Application Discontinuation
1977
- 1977-02-10 SE SE7701523A patent/SE417957B/xx unknown
- 1977-11-25 ES ES456279A patent/ES456279A1/es not_active Expired

Also Published As

Publication number	Publication date
GB1456838A (en)	1976-11-24
FI58912C (fi)	1981-05-11
NO743616L (no)	1974-05-09
CA1033727A (en)	1978-06-27
DK143499C (da)	1982-01-11
AU6230273A (en)	1975-05-08
NO144385B (no)	1981-05-11
FR2291200B1 (ru)	1979-01-05
SE412229B (sv)	1980-02-25
SE7612262L (sv)	1976-11-03
BE807046A (fr)	1974-05-08
IL50310A (en)	1977-08-31
JPS5714347B2 (ru)	1982-03-24
SE7612261L (sv)	1976-11-03
ZA738595B (en)	1974-09-25
AT345999B (de)	1978-10-10
IN139265B (ru)	1976-05-29
IL43571A0 (en)	1974-03-14
DE2355731A1 (de)	1974-05-22
DE2355731C3 (de)	1981-01-15
FR2291200A1 (fr)	1976-06-11
IE40043L (en)	1974-05-08
ES420386A1 (es)	1976-07-01
CH593930A5 (ru)	1977-12-30
FR2205338B1 (ru)	1978-07-13
FI58912B (fi)	1981-01-30
NO143663B (no)	1980-12-15
DK143499B (da)	1981-08-31
NO143663C (no)	1981-03-25
SE7701523L (sv)	1977-02-10
DE2355731B2 (de)	1980-04-30
SE417957B (sv)	1981-04-27
NO144385C (no)	1981-08-19
FR2286147A1 (fr)	1976-04-23
FR2205338A1 (ru)	1974-05-31
IE40043B1 (en)	1979-02-28
ES456279A1 (es)	1978-11-01
PH13261A (en)	1980-02-25
ES444398A1 (es)	1977-12-01
SU704456A3 (ru)	1979-12-15
FR2286147B1 (ru)	1978-09-22
IL43571A (en)	1977-08-31
NL7315307A (ru)	1974-05-10
JPS49133357A (ru)	1974-12-21
PH13320A (en)	1980-03-13
ATA941073A (de)	1978-02-15

Publication	Publication Date	Title
SU667131A3 (ru)	1979-06-05	Способ получени производных простановой кислоты или их эпимеров
Pike et al.	1969	Prostanoic acid chemistry
SU620207A3 (ru)	1978-08-15	Способ получени оптически активных соединений р да простагландинов
KR920000956B1 (ko)	1992-01-31	아줄렌 유도체의 제조방법
US3524867A (en)	1970-08-18	Process for producing cyclopenta (b)pyrans
US3778450A (en)	1973-12-11	Certain bicyclic lactones
US3835179A (en)	1974-09-10	Novel 15-substituted prostanoic acids and esters
Ziegler et al.	1971	Gibbane synthons via hexahydrofluorenones. Intramolecular Reformatsky reaction
US4118584A (en)	1978-10-03	9-Deoxy-9-methylene-16-phenyl-PGF compounds
US4001300A (en)	1977-01-04	2,2-Difluoro-16-phenoxy-PGF2 analogs
Huitric et al.	1956	The Infrared and Ultraviolet Spectra, Dipole Moments and Structures of Some New 2-(α-Hydroxy-p-halobenzyl)-cyclohexanones and Related Compounds1
US3886185A (en)	1975-05-27	Novel prostaglandin intermediates and process for the production thereof
JPH06345777A (ja)	1994-12-20	ジイソピノカンフェニルクロロボランのインシトゥー製造
US3758511A (en)	1973-09-11	Preparation of d,1-zearalenones
US4429123A (en)	1984-01-31	Preparation of 6-keto-7-oxo-PGF1α -derivatives
CA1060007A (en)	1979-08-07	2a,2b-dihomo-16,16-dimethyl-prostaglandin analogs
DK149859B (da)	1986-10-13	Fremgangsmaade til fremstilling af rifamycin p og q eller 25-deacetylderivater deraf
JPS6033826B2 (ja)	1985-08-05	フルオロプロスタグランジン及びその製造法
US3413338A (en)	1968-11-26	2-nitrocyclopent-1-enecarboxylic acid
US3998852A (en)	1976-12-21	Novel prostaglandin intermediates and process for the production thereof
US3935241A (en)	1976-01-27	11α-METHYLSUBSTITUTED PROSTAGLANDIN DERIVATIVES
CA1152504A (en)	1983-08-23	Prostaglandin derivatives of the .delta.2-pgf.sub.2 and .delta.2-pge.sub.2 series and process for their manufacture
US3897483A (en)	1975-07-29	Novel 1-acyloxy-2-(omega-carboalkoxyalkyl)cycloalk-1-enes
IE57058B1 (en)	1992-04-08	2,2-diethoxypropionic acid derivatives
US4055564A (en)	1977-10-25	Novel prostaglandin intermediates and process for the production thereof