SU704456A3 - Способ получени -кетофосфонатов - Google Patents

Способ получени -кетофосфонатов

Info

Publication number: SU704456A3
Authority: SU; USSR - Soviet Union
Prior art keywords: ketophosphonates; preparing beta; solution; temperature; stirring
Prior art date: 1972-11-08

Application number

SU752182652A

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

1975-12-23

Publication date

1979-12-15

1975-12-23 Application filed by Пфайзер Инк., (Фирма) filed Critical Пфайзер Инк., (Фирма)

1979-12-15 Application granted granted Critical

1979-12-15 Publication of SU704456A3 publication Critical patent/SU704456A3/ru

Links

238000000034 method Methods 0.000 title description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
NIWUMFULEUZEOT-UHFFFAOYSA-N O=P1OOO1 Chemical class O=P1OOO1 NIWUMFULEUZEOT-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
-1 2-indanyl Chemical group 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
125000000217 alkyl group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229940094443 oxytocics prostaglandins Drugs 0.000 description 2
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
150000003180 prostaglandins Chemical class 0.000 description 2
INDCQOTULGRLGI-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-2-dimethoxyphosphorylethanone Chemical compound C1=CC=C2CC(C(=O)CP(=O)(OC)OC)CC2=C1 INDCQOTULGRLGI-UHFFFAOYSA-N 0.000 description 1
JZFOBTPKPKPPSX-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-2-yl)-3-dimethoxyphosphorylpropan-2-one Chemical compound C1=CC=C2CC(CC(=O)CP(=O)(OC)OC)CC2=C1 JZFOBTPKPKPPSX-UHFFFAOYSA-N 0.000 description 1
QDTUIHOOSMFIDM-UHFFFAOYSA-N 2-(5,6-dimethoxy-2,3-dihydro-1h-inden-1-yl)acetic acid Chemical compound C1=C(OC)C(OC)=CC2=C1C(CC(O)=O)CC2 QDTUIHOOSMFIDM-UHFFFAOYSA-N 0.000 description 1
125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 description 1
BBHJTCADCKZYSO-UHFFFAOYSA-N 4-(4-ethylcyclohexyl)benzonitrile Chemical compound C1CC(CC)CCC1C1=CC=C(C#N)C=C1 BBHJTCADCKZYSO-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
DWHMMGGJCLDORC-UHFFFAOYSA-N methoxy(methyl)phosphinic acid Chemical compound COP(C)(O)=O DWHMMGGJCLDORC-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

Description

Изобретение относитс к способу получени новых р-кетофосфонатов, которые могут найти, применение в фар мацевтической промышленности в качес не промежуточных веществ дл получени новых аналогов природных простагландйнов . Известен способ получени р-кетофосфонатов конденсацией фосфоната со сложным эфиром карбоновой кислоты в среде инертного органического раство рител в присутствии основани , например н-бутллити , при охлаждении, в атмосфере инертного газа. Целью изобретени вл етс раЗра ботка способа получени новых р-кетофосфонатов , простагландины на осно ве которых обладайт улучшенными свой ствами. Поставленна цель достигаетс спо собом получени (З-кетофосфонатов общей формулы 1 A-(CHj -c-CH-p: где А - циклоалкил С а- 1 адамантил , 2-норборнил, 2-Ц ,2,3,4-тетрагидронафтил ), незамещенный или замещенный галоидом, трифторметилом, низ шим алкилом или низшим алкоксилсэм 2- -инданил, п, - це-лое число 0-5, заключающийс в том, что диметилметилфосфонат подвергают взаимодействию со сложным эфиром общей формулы fl А - (CH2)ii COOAlK, где А и п, - имеют указанные значени , А1 к представл ет собой низший алкйл. Предложенный способ более подробно осуществл ют следующим образом. Раствор диметилметилфосфоната в тетрагидрофуране охлаждают до .-78°С в атмосфере сухого дзота, посл,е чего по капл м, постепенно добавл ют в него н-бутил.литий. После перемешивани покапл м добавл ют Сложный эфир форму.пы Г. После выдержки в течение 3-4 ч при температуре смеаь нагревают до комнатной температуры, нейтрализуют уксусной кислотой и выпаривают в роторн кГ испарителе до образовани белого гел . Желатинообразный материал экстра- гируют водой, после чего водную фазу экстрагируют хлороформом, органические экстракты собирают вместе, промывают, сушат и концентрируют с получением целевого продукта. Пример. Диметил-2-оксо-2- (2-инданил)этилфосфонат).

Раствор 20,4 г (164 глмол ) диме;тилметилфосфоната в 200 мл тетра гидрофурана охлаждают до 78° С в 5.тмосфере сухого азота В перемешива.емьай фосфонатный раствор добавл ют 82,6 мл 2,25 М раствора н-бутиллити в гексане по капл м в течение 20 кин с такой скоростью, при которой исключаетс возможность повышени температуры выше - 65°С, После дополнительного перемешивани в течфние 5 мин при -78°С по капл м со скоростью, позвол ющей поддерживать температуру ниже в течение 20 мин добавл ют 14,0 г (73,5 ммол ,6-диметокси-инданил-2 карб6к илата По истечении 1,0 ч выдержка при реакционной смеси даWT Нагретьс до комнатнойтемпера ,т ь|ры/ затем ее нейтрализуют 20 мл уг сусной кислоты и выпаривают в. роторном испарителе дообразовани белого гел . Желатинообразный материал экстрагируют 50 мл воды, водную фазу экстрагируют порци ми -по

Т. кип. с/мм. л рт. ст.

LC

о (0,2)

О

1 160-162 (0,2)

75 метиленхлорида (всего 4 порции), собирают органические экстракты, и промывают 75 мл. воды, высушивают над сульфатом магни и концентрируют в вакууме водоструйного насоса. Получают сырой остаток, который перегон ют т.кип. 150-160 С при 0,1 M|vi рт.ст) с получением 17,0 г (86,4/удиметил-2-оксО -2- (2--инданил) -этилфбсфоната.

На спектре ЯМР (CDCC, ) ;перегнанного продукта имелс синглет. 7,15сГдл ароматических протонов, дублет при 7,76(f(J-ll сПз) дл ОСН,. синглет при 3,25.cf дл бензиловьдх протонов, дублет при 3,18 cf ( D-23 сПз) дл РСНг и искаженный тр.иплет при 3,l8d ( 3 2 CJIa) дл СНСО.

Аналбгично примеру 1, использу соответствующие сложные, эфиры формулы 1 , получают целевые продукты формулы Г.

В таблице приведены температуры .кипени и данные ЯМР-спектроскопии полученн э1х продуктов.

6,73(ВЬ 3,.S6(S) 3,7B(d) 3,2,,2{d)

3,77(d)- 3,-06(cI), .2,,50(d)

209-212

(0,002)

3/70(d)f 2,93(d), 2,23(S)

195-200 (0,02)

3,75(d), 3,08(d), 2,53(n)

138-141 (0,3)

четкий Резонанс

,a

3,78(d)

3,05(3)

И p и м e p 2. Диметил-2-оксо-3- (2-инданил)пропилфосфонат..

Раствор 20,4 г (164 ммолей диметилметилфосфаната ) в 200 мл тетрагидрофурана охлаждают до в .атмосфере сухого азота. В перемешнва:емь1й фосфонатный раствор добавл ют 82,6 мл 2,25 М раствора н-бутиллити в гексане по капл м в теч .ение 20 мин с такой скоростью, при которой температура не превышает -65°С« После дополнительных 5 мин перемешивани при температуре по капл м добавл ют 14,0 г (77р5 ммол ) 5,6-диметокси-2-инданилацетата с такой скоростью, при. которой реак

SU752182652A 1972-11-08 1975-12-23 Способ получени -кетофосфонатов SU704456A3 (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
SU704456A3 true SU704456A3 (ru)	1979-12-15

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 Before (1)

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

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)	IL43571A (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)

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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
KR20010023837A (ko) *	1997-09-09	2001-03-26	데이비드 엠 모이어	Ｆｐ 작동약으로 유용한 방향족 ｃ16-ｃ20-치환된테트라히드로 프로스타글란딘
ID24845A (id) *	1997-09-09	2000-08-24	Procter & Gamble	Prostaglandin tetrahidro tersubstitusi c16-c20 aromatik yang berguna sebagai agonis fp
CA2303764C (en) *	1997-09-09	2005-02-15	The Procter & Gamble Company	Aromatic c16-c20-substituted tetrahydro prostaglandins useful as fp agonists
CA2364948C (en) *	1999-03-05	2011-04-26	Duke University	C16 unsaturated fp-selective prostaglandins analogs
US20020172693A1 (en)	2000-03-31	2002-11-21	Delong Michell Anthony	Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
US20020013294A1 (en)	2000-03-31	2002-01-31	Delong Mitchell Anthony	Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives
US20020037914A1 (en)	2000-03-31	2002-03-28	Delong Mitchell Anthony	Compositions and methods for treating hair loss using C16-C20 aromatic tetrahydro prostaglandins
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Publication number	Priority date	Publication date	Assignee	Title
JPS4864073A (ru) *	1971-04-30	1973-09-05

1973
- 1973-11-05 IL IL43571A patent/IL43571A/en unknown
- 1973-11-05 IL IL50310A patent/IL50310A/en unknown
- 1973-11-06 SE SE7315074A patent/SE412229B/xx unknown
- 1973-11-08 PH PH15197A patent/PH13261A/en unknown
- 1973-11-08 NL NL7315307A patent/NL7315307A/xx not_active Application Discontinuation
- 1973-11-08 FR FR7339758A patent/FR2205338B1/fr not_active Expired
- 1973-11-08 CH CH1570773A patent/CH593930A5/xx not_active IP Right Cessation
- 1973-11-08 DE DE2355731A patent/DE2355731C3/de not_active Expired
- 1973-11-08 ZA ZA738595A patent/ZA738595B/xx unknown
- 1973-11-08 NO NO4294/73A patent/NO143663C/no unknown
- 1973-11-08 JP JP12584373A patent/JPS5714347B2/ja not_active Expired
- 1973-11-08 CA CA185,366A patent/CA1033727A/en not_active Expired
- 1973-11-08 GB GB5199773A patent/GB1456838A/en not_active Expired
- 1973-11-08 DK DK603373A patent/DK143499C/da active
- 1973-11-08 IE IE2014/73A patent/IE40043B1/xx unknown
- 1973-11-08 FI FI3455/73A patent/FI58912C/fi active
- 1973-11-08 BE BE1005488A patent/BE807046A/xx unknown
- 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 FR7602434A patent/FR2291200A1/fr active Granted
- 1976-01-29 FR FR7602433A patent/FR2286147A1/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
AU6230273A (en)	1975-05-08
IN139265B (ru)	1976-05-29
FR2291200B1 (ru)	1979-01-05
FR2291200A1 (fr)	1976-06-11
SE7701523L (sv)	1977-02-10
SE7612262L (sv)	1976-11-03
GB1456838A (en)	1976-11-24
ES456279A1 (es)	1978-11-01
FI58912B (fi)	1981-01-30
DE2355731A1 (de)	1974-05-22
AT345999B (de)	1978-10-10
NO143663B (no)	1980-12-15
IL50310A (en)	1977-08-31
CH593930A5 (ru)	1977-12-30
ES444398A1 (es)	1977-12-01
DE2355731B2 (de)	1980-04-30
FR2286147B1 (ru)	1978-09-22
NO143663C (no)	1981-03-25
IL43571A0 (en)	1974-03-14
PH13261A (en)	1980-02-25
JPS49133357A (ru)	1974-12-21
PH13320A (en)	1980-03-13
FI58912C (fi)	1981-05-11
NO144385C (no)	1981-08-19
FR2205338A1 (ru)	1974-05-31
NO144385B (no)	1981-05-11
FR2205338B1 (ru)	1978-07-13
JPS5714347B2 (ru)	1982-03-24
IE40043B1 (en)	1979-02-28
CA1033727A (en)	1978-06-27
ATA941073A (de)	1978-02-15
IE40043L (en)	1974-05-08
DK143499C (da)	1982-01-11
SU667131A3 (ru)	1979-06-05
SE7612261L (sv)	1976-11-03
SE412229B (sv)	1980-02-25
DE2355731C3 (de)	1981-01-15
DK143499B (da)	1981-08-31
NO743616L (no)	1974-05-09
IL43571A (en)	1977-08-31
ES420386A1 (es)	1976-07-01
SE417957B (sv)	1981-04-27
NL7315307A (ru)	1974-05-10
ZA738595B (en)	1974-09-25
FR2286147A1 (fr)	1976-04-23
BE807046A (fr)	1974-05-08

Publication	Publication Date	Title
JPS5814433B2 (ja)	1983-03-18	ガンマ−ピロン類合成の中間体およびその製造方法
Janecki et al.	1989	A convenient Horner-Emmons approach to the synthesis of substituted ethyl 1, 3-butadiene-2-carboxylates, and related compounds
Zhou et al.	1998	Synthesis of novel thio (seleno) phosphate‐phosphonates and their biological activities
JPH01125392A (ja)	1989-05-17	メタンホスホン酸モノメチルエステルアンモニウム塩及びその製法
JPS6310710B2 (ru)	1988-03-08
WO1997033893A1 (en)	1997-09-18	Process for the preparation of tetraethyl methylenebisphosphonate
US3894026A (en)	1975-07-08	Production of thebaine
JP2023520135A (ja)	2023-05-16	ビタミンａの生成方法
US4288642A (en)	1981-09-08	Production of ω-alkene-1-ols
KR930005008B1 (ko)	1993-06-11	N-포스포노메틸글리신의 제조방법
SU1033498A1 (ru)	1983-08-07	Способ получени дигалогенангидридов 2-алкоксиалкенилфосфонистых кислот
Kirpichenok et al.	1990	Synthesis of 4-chloro-7-dialkylaminocoumarins
Morpain et al.	1990	IMPROVED PREPARATION OF DI-O-ISOPROPYLIDENE-1, 2; 5, 6-D-MANNITOL
SU1682358A1 (ru)	1991-10-07	Способ получени фосфорилированных полуацеталей полуаминалей кетена
SU410020A1 (ru)	1974-01-05
Trofimov et al.	1992	Addition of methyl mercaptoacetate to N-vinylpyrroles
Binder et al.	1991	Transannularly bridged di-µ2-thiotetraborane (10). Dynamics, cis–trans-isomerism, reversible rearrangement: bis (diboranyl)‘butterfly’structure
Facchin et al.	1988	Witting reaction on carbonyl-containing cyclotriphosphazenes: the case of hexakis (4-formylphenoxy) cyclophosphazene
SU487891A1 (ru)	1975-10-15	Способ получени алкиненфосфитов
SU722900A1 (ru)	1980-03-25	Способ получени алкиловых эфиров 2,3-дифинилинден-1-карбоновой кислоты
RU1773912C (ru)	1992-11-07	Способ получени @ -трифторацетил- @ -бутиролактона
SU761495A1 (ru)	1980-09-07	Способ получения растворимого полихлорфосфазена
JPS6363685A (ja)	1988-03-22	環状ホスホン酸モノエステルおよびその製造法
SU386953A1 (ru)	1973-06-21	Способ получения ацеталей, содержащих трехкоординированный атом фосфора
SU763350A1 (ru)	1980-09-15	Способ получени 2-оксо-2-этокси- 5-диэтилфосфоно-1,2-оксафосфоланов