JPS53101385A - Method of producing phenyllpyrimidine - Google Patents

Method of producing phenyllpyrimidine

Info

Publication number
JPS53101385A
JPS53101385A JP1997778A JP1997778A JPS53101385A JP S53101385 A JPS53101385 A JP S53101385A JP 1997778 A JP1997778 A JP 1997778A JP 1997778 A JP1997778 A JP 1997778A JP S53101385 A JPS53101385 A JP S53101385A
Authority
JP
Japan
Prior art keywords
phenyllpyrimidine
producing
producing phenyllpyrimidine
Prior art date
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.)
Pending
Application number
JP1997778A
Other languages
English (en)
Inventor
Arthur Boller
Marco Cereghetti
Hanspeter Scherrer
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
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.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of JPS53101385A publication Critical patent/JPS53101385A/ja
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/515Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/02Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
    • C07C47/12Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing more than one —CHO group
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00Compounds having —CHO groups
    • C07C47/20Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/277Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/30Halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32One oxygen, sulfur or nitrogen atom
    • C07D239/34One oxygen atom
    • C07D239/36One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00Liquid crystal materials
    • C09K19/04Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06Non-steroidal liquid crystal compounds
    • C09K19/34Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/345Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
    • C09K19/3458Uncondensed pyrimidines

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Liquid Crystal Substances (AREA)
  • Liquid Crystal (AREA)
JP1997778A 1974-10-25 1978-02-24 Method of producing phenyllpyrimidine Pending JPS53101385A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH1431374A CH617452A5 (ja) 1974-10-25 1974-10-25

Publications (1)

Publication Number Publication Date
JPS53101385A true JPS53101385A (en) 1978-09-04

Family

ID=4399774

Family Applications (3)

Application Number Title Priority Date Filing Date
JP50127576A Granted JPS5180870A (en) 1974-10-25 1975-10-24 Fueniruupirimijinno seizohoho
JP1997678A Pending JPS53114788A (en) 1974-10-25 1978-02-24 Nematic liquid crystal matter mixture
JP1997778A Pending JPS53101385A (en) 1974-10-25 1978-02-24 Method of producing phenyllpyrimidine

Family Applications Before (2)

Application Number Title Priority Date Filing Date
JP50127576A Granted JPS5180870A (en) 1974-10-25 1975-10-24 Fueniruupirimijinno seizohoho
JP1997678A Pending JPS53114788A (en) 1974-10-25 1978-02-24 Nematic liquid crystal matter mixture

Country Status (18)

Country Link
US (1) US3997536A (ja)
JP (3) JPS5180870A (ja)
AT (1) AT349475B (ja)
AU (1) AU476921B2 (ja)
BE (1) BE834837A (ja)
CA (1) CA1042889A (ja)
CH (1) CH617452A5 (ja)
DD (2) DD128698A5 (ja)
DE (1) DE2547737C2 (ja)
DK (2) DK479675A (ja)
ES (1) ES442044A1 (ja)
FR (1) FR2309543A1 (ja)
GB (1) GB1473990A (ja)
HK (1) HK7278A (ja)
IT (1) IT1043486B (ja)
NL (1) NL176172C (ja)
SE (1) SE417962B (ja)
ZA (1) ZA756410B (ja)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61215372A (ja) * 1985-03-20 1986-09-25 Teikoku Chem Ind Corp Ltd 液晶化合物

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4062798A (en) * 1975-09-19 1977-12-13 Hoffmann-La Roche Inc. Phenylpyrimidine derivatives
US4180475A (en) * 1976-02-26 1979-12-25 Hoffmann La Roche Liquid crystal mixtures
US4052396A (en) * 1976-11-22 1977-10-04 Ciba-Geigy Corporation Process for the production of 2-alkyl or 2-cycloalkyl-4-methyl-6-hydroxypyrimidines
US4052397A (en) * 1976-11-22 1977-10-04 Ciba-Geigy Corporation Process for the production of 2-alkyl or 2-cycloalkyl-4-methyl-6-hydroxypyrimidines
JPS5411887A (en) * 1977-06-29 1979-01-29 Sharp Corp Liquid crystal composition
DD138558A1 (de) * 1977-12-08 1979-11-07 Frank Kuschel Nematische fluessig-kristalline gemische
JPS5483694A (en) * 1977-12-16 1979-07-03 Hitachi Ltd Nematic liquid crystal body for display device
JPS5941983B2 (ja) * 1978-02-17 1984-10-11 大日本インキ化学工業株式会社 トランス(エカトリアル↓−エカトリアル)1,4↓−ジ置換シクロヘキサン誘導体
US4309539A (en) * 1978-03-13 1982-01-05 Hoffmann-La Roche Inc. Pyrimidine derivatives
US4163848A (en) * 1978-08-08 1979-08-07 Ciba-Geigy Corporation Process for the production of 2-alkyl- or cycloalkyl-4-methyl-6-hydroxypyrimidines
JPS5534206A (en) * 1978-08-30 1980-03-10 Hitachi Ltd Nematic liquid crystal for display unit
DE2944905A1 (de) * 1978-12-13 1980-10-23 Werk Fernsehelektronik Veb Kristallin-fluessige substituierte 1,3-dioxane und diese enthaltende gemische
US4273929A (en) * 1979-02-05 1981-06-16 Hoffmann-La Roche Inc. Heterocyclic compounds
DE3014912A1 (de) * 1979-05-15 1980-11-27 Werk Fernsehelektronik Veb Nematische fluessigkristalline 5-cyan- 2- eckige klammer auf 4-acyloxyphenyl eckige klammer zu -pyrimidine und diese enthaltende gemische
DE3063497D1 (en) * 1979-08-20 1983-07-07 Werk Fernsehelektronik Veb Nematic crystalline-liquid 5-alkyl-2-(4-acyloxyphenyl)-pyrimidines for opto-electronic arrangements and process for their preparation
US4364838A (en) * 1979-11-14 1982-12-21 Hoffmann-La Roche Inc. Liquid crystal mixtures
CH652400A5 (en) * 1979-11-14 1985-11-15 Hoffmann La Roche Phenyldioxanes, and liquid-crystalline mixtures containing them
DE2951099A1 (de) * 1979-12-19 1981-06-25 Merck Patent Gmbh, 6100 Darmstadt Tetrahydrochinazoline, verfahren zu ihrer herstellung, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement
JPS56113768A (en) * 1980-02-15 1981-09-07 Seiko Epson Corp Compound
JPS56116774A (en) * 1980-02-19 1981-09-12 Seiko Epson Corp Nematic liquid crystal composition
US4335011A (en) * 1980-03-28 1982-06-15 Timex Corporation Cyclohexyl-dioxane liquid crystalline compounds
US4335012A (en) * 1980-04-03 1982-06-15 Timex Corporation 5-Substituted-2-(4-cyanophenyl)-1,3-dioxanes
DE3023989A1 (de) * 1980-06-26 1982-01-21 Merck Patent Gmbh, 6100 Darmstadt Fluessigkristallines dielektrikum
CH645102A5 (de) * 1980-10-14 1984-09-14 Hoffmann La Roche Disubstituierte pyrimidine.
JPS5790082A (en) * 1980-11-26 1982-06-04 Seiko Epson Corp Liquid crystal composition
JPS57117583A (en) * 1981-01-12 1982-07-22 Seiko Epson Corp Liquid crystal composition
US4452718A (en) * 1981-07-31 1984-06-05 Hoffmann-La Roche Inc. Pyridazines
CH651025A5 (de) * 1982-05-14 1985-08-30 Hoffmann La Roche Pyridazine und ihre verwendung als komponenten fluessigkristalliner gemische.
US4528114A (en) * 1981-12-18 1985-07-09 Hoffmann-La Roche Inc. Acetylenes
US5227484A (en) * 1982-01-14 1993-07-13 Merck Patent Gmbh Anisotropic compounds having nematic phase and liquid crystal mixtures
JPS58128356A (ja) * 1982-01-28 1983-07-30 Ube Ind Ltd 2−アルコキシメチレン−3,3−ジアルコキシブロパンニトリル類
GB2120242A (en) * 1982-04-30 1983-11-30 Erba Farmitalia Ergoline derivatives
JPS5939876A (ja) * 1982-08-26 1984-03-05 Chisso Corp ピリミジン誘導体
GB2133004B (en) * 1982-11-04 1986-06-11 Ici Plc Process for the extraction of metal values and novel metal extractants
DE3465192D1 (en) * 1983-03-16 1987-09-10 Hoffmann La Roche Liquid crystal components having an alkenyl chain
US4581155A (en) * 1983-03-31 1986-04-08 Chisso Corporation Halogenopyrimidine derivatives
DE3315295A1 (de) * 1983-04-27 1984-10-31 Merck Patent Gmbh, 6100 Darmstadt Fluorhaltige pyrimidinderivate
EP0136480B1 (en) * 1983-08-22 1990-01-17 Chisso Corporation 2,3-dicyano-5-substituted pyrazines and liquid crystal composition containing them
JPS60146877A (ja) * 1984-01-11 1985-08-02 Chisso Corp 2―置換―6―(5―置換―2―ピリミジニル)ナフタリン
US4609485A (en) * 1984-02-17 1986-09-02 Chisso Corporation Bipyrimidinyl derivatives
DE3411571A1 (de) * 1984-03-29 1985-10-10 Merck Patent Gmbh, 6100 Darmstadt Pyrimidine
DE3561395D1 (de) * 1984-05-25 1988-02-18 Hoffmann La Roche Phenylisothiocyanates
DE3577211D1 (de) * 1984-06-07 1990-05-23 Seiko Instr Inc Fluessigkristallverbindung.
JPS61152659A (ja) * 1984-12-27 1986-07-11 Chisso Corp 1,4−ジピリミジニルベンゼン誘導体
DE3500909A1 (de) * 1985-01-12 1986-07-17 Merck Patent Gmbh, 6100 Darmstadt Pyrimidine
JPS61180775A (ja) * 1985-01-22 1986-08-13 メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング ジヒドロアジン液晶化合物
JPS61197563A (ja) * 1985-02-27 1986-09-01 Chisso Corp トリフルオロメチルフエニル基をもつピリミジン誘導体
JPS61233689A (ja) * 1985-03-22 1986-10-17 メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング 複素環式ホウ素化合物
DE3667170D1 (de) * 1985-03-26 1990-01-04 Hoffmann La Roche Alkenylsubstituierte phenylisothiocyanate und benzonitrile.
US4980082A (en) * 1986-09-02 1990-12-25 Seiko Instruments Inc. Ferroelectric SmC liquid crystal composition which comprises pyrimidinylphenyl ester compounds
CA1341098C (en) * 1988-08-25 2000-09-12 Kazuhiko Sakaguchi Liquid crystal composition and use thereof
DE3928267A1 (de) * 1989-08-26 1991-02-28 Merck Patent Gmbh 5-oxy-2-phenylpyrimidine und fluessigkristallines medium
JPH07278545A (ja) * 1994-04-14 1995-10-24 Chisso Corp ネマテック液晶組成物
CN103965111A (zh) * 2014-05-05 2014-08-06 淮海工学院 一种含有水杨醛席夫碱的双子季铵盐及其制备方法
CN106660957B (zh) * 2014-07-08 2019-11-29 美国陶氏益农公司 4-烷氧基-3-羟基吡啶甲酸的制备方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH593495A5 (ja) * 1971-12-22 1977-12-15 Werk Fernsehelektronik Veb
DD107563A1 (ja) * 1973-09-27 1974-08-05

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61215372A (ja) * 1985-03-20 1986-09-25 Teikoku Chem Ind Corp Ltd 液晶化合物
JPH0552310B2 (ja) * 1985-03-20 1993-08-05 Teikoku Hormone Mfg Co Ltd

Also Published As

Publication number Publication date
NL176172B (nl) 1984-10-01
SE417962B (sv) 1981-04-27
US3997536A (en) 1976-12-14
JPS53114788A (en) 1978-10-06
DD124731A5 (ja) 1977-03-09
JPS5180870A (en) 1976-07-15
DE2547737C2 (de) 1982-09-16
ES442044A1 (es) 1977-06-16
ATA814575A (de) 1978-09-15
CA1042889A (en) 1978-11-21
SE7511902L (sv) 1976-04-26
NL7512497A (nl) 1976-04-27
FR2309543B1 (ja) 1978-04-07
AU8567075A (en) 1976-10-07
BE834837A (fr) 1976-04-26
FR2309543A1 (fr) 1976-11-26
JPS556631B2 (ja) 1980-02-18
AU476921B2 (en) 1976-10-07
DK382677A (da) 1977-08-29
NL176172C (nl) 1985-03-01
DE2547737A1 (de) 1976-04-29
IT1043486B (it) 1980-02-20
GB1473990A (en) 1977-05-18
DD128698A5 (de) 1977-12-07
ZA756410B (en) 1976-09-29
DK479675A (da) 1976-04-26
AT349475B (de) 1979-04-10
HK7278A (en) 1978-02-17
CH617452A5 (ja) 1980-05-30

Similar Documents

Publication Publication Date Title
JPS53101385A (en) Method of producing phenyllpyrimidine
CS188985B2 (en) Method of producing aryl-1-azolylmethanes
CS191960B2 (en) Method of producing novel 2-decarboxy-2-/5-tatrazolyl/-11-deoxy-omega-pentanorprostaglandins
JPS51125767A (en) Method of producing food
BG24812A3 (en) Method of obtaining 8-thiomethylergolins
ZA75496B (en) Method of producing 1-n-<l-(-)-alpha-hydroxy-epsilon-aminobutyryl> xk-62-2
BG24542A3 (en) Method of preparing carbonylaldiminomethanphosphonates
CS187318B2 (en) Method of producing acylureidocephalosporin compounds
CS188235B2 (en) Method of producing new derivatives ryfamicine
CS191882B2 (en) Method of preparing 7-methoxy-6-thia-tetracycline
CS191264B2 (en) Method of producing new pyridobenzodiazepinones
CS188938B2 (en) Method of producing xanthene-9-spiro-4-piperidines
SU677666A3 (en) Method of producing 7l-or extradiols
CS193042B2 (en) Method of producing thiocarbamates
CS183850B2 (en) Method of producing 5-fluor-2-methyl-1-/p-methyl-sulphinylbenzyliden/-3-indenylacetic acid
CS189635B2 (en) Method of producing bromderivatives of 4-imido-thioazetidin-2-one
CS182298B2 (en) Method of producing substituted benzendisulphon-amides
CS183785B2 (en) Method of producing s-triazolo-3,4-benzothiazoles
CS182292B2 (en) Method of producing melone
CS194733B2 (en) Method of producing novel 11-deoxy-omega-pentanorprostaglandins
CS179686B1 (en) Method of producing basic phenylethers
CS188945B2 (en) Method of producing 1-aryluracils
CS185674B2 (en) Method of producing 1-phenyl-4-amino-5-chlor-6-pyridazone
CS188978B2 (en) Method of producing 3-methyl-3-phenyl-pyrazolidin-5-ones
CS190494B2 (en) Method of producing pgf beta-prostaglandins