SU1709904A3 - Способ получени производных гидроксамовой кислоты - Google Patents

Способ получени производных гидроксамовой кислоты Download PDF

Info

Publication number: SU1709904A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mixture; stripped; added; product; solution
Prior art date: 1987-07-15

Application number

SU884356229A

Other languages

English (en)

Russian (ru)

Inventor

Энтони Сэлмон Джон

Пол Джексон Вилльям

Original Assignee

Дзе Велкам Фаундейшн Лимитед (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.)

1987-07-15

Filing date

1988-07-14

Publication date

1992-01-30

1988-07-14 Application filed by Дзе Велкам Фаундейшн Лимитед (Фирма) filed Critical Дзе Велкам Фаундейшн Лимитед (Фирма)

1992-01-30 Application granted granted Critical

1992-01-30 Publication of SU1709904A3 publication Critical patent/SU1709904A3/ru

Links

239000002253 acid Substances 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title claims description 5
230000015572 biosynthetic process Effects 0.000 title 1
238000003786 synthesis reaction Methods 0.000 title 1
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims description 2
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims description 2
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims 1
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims 1
239000000443 aerosol Substances 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
238000000338 in vitro Methods 0.000 claims 1
238000001727 in vivo Methods 0.000 claims 1
230000005764 inhibitory process Effects 0.000 claims 1
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 115
239000000203 mixture Substances 0.000 description 60
239000000047 product Substances 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000007864 aqueous solution Substances 0.000 description 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
239000000243 solution Substances 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
239000003208 petroleum Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 11
239000000284 extract Substances 0.000 description 10
-1 Phenoxyphenyl Chemical group 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000000605 extraction Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
239000000463 material Substances 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000000706 filtrate Substances 0.000 description 5
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 4
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 4
229960001171 acetohydroxamic acid Drugs 0.000 description 4
238000001816 cooling Methods 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
FZCDOAKFNUYYNN-UHFFFAOYSA-N 4-(3-phenoxyphenyl)but-3-en-2-ol Chemical compound CC(O)C=CC1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDOAKFNUYYNN-UHFFFAOYSA-N 0.000 description 3
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
KZNWHSVHYRGQOC-UHFFFAOYSA-N 1-(dibromomethyl)-3-(4-fluorophenoxy)benzene Chemical compound C1=CC(F)=CC=C1OC1=CC=CC(C(Br)Br)=C1 KZNWHSVHYRGQOC-UHFFFAOYSA-N 0.000 description 1
CQQKJQFZEKLGFT-UHFFFAOYSA-N 1-fluoro-3-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=C(F)C=CC=2)=C1 CQQKJQFZEKLGFT-UHFFFAOYSA-N 0.000 description 1
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 1
HTBZPEDBMOXWID-UHFFFAOYSA-N 3-(4-fluorophenoxy)benzaldehyde Chemical compound C1=CC(F)=CC=C1OC1=CC=CC(C=O)=C1 HTBZPEDBMOXWID-UHFFFAOYSA-N 0.000 description 1
RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000755093 Gaidropsarus vulgaris Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
239000004367 Lipase Substances 0.000 description 1
102000004882 Lipase Human genes 0.000 description 1
108090001060 Lipase Proteins 0.000 description 1
102000003820 Lipoxygenases Human genes 0.000 description 1
108090000128 Lipoxygenases Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241001602876 Nata Species 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000004568 cement Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940045803 cuprous chloride Drugs 0.000 description 1
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000010410 layer Substances 0.000 description 1
235000019421 lipase Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
230000003228 microsomal effect Effects 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229940088417 precipitated calcium carbonate Drugs 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000010008 shearing Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SU884356229A 1987-07-15 1988-07-14 Способ получени производных гидроксамовой кислоты SU1709904A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878716640A GB8716640D0 (en)	1987-07-15	1987-07-15	Aryl derivatives

Publications (1)

Publication Number	Publication Date
SU1709904A3 true SU1709904A3 (ru)	1992-01-30

Family

ID=10620673

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU884356229A SU1709904A3 (ru)	1987-07-15	1988-07-14	Способ получени производных гидроксамовой кислоты

Country Status (5)

Country	Link
CS (1)	CS274432B2 (cs)
DD (1)	DD281804A5 (cs)
GB (1)	GB8716640D0 (cs)
SU (1)	SU1709904A3 (cs)
ZA (1)	ZA885103B (cs)

1987
- 1987-07-15 GB GB878716640A patent/GB8716640D0/en active Pending
1988
- 1988-07-14 DD DD31794088A patent/DD281804A5/de not_active IP Right Cessation
- 1988-07-14 SU SU884356229A patent/SU1709904A3/ru active
- 1988-07-14 CS CS508488A patent/CS274432B2/cs unknown
- 1988-07-14 ZA ZA885103A patent/ZA885103B/xx unknown

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Патент US № 37АО'»37, кл. С 07 С 83/10, 1977.Патент БПВW 0196l8«t, кл. С 07 С 83/10, 1986. *

Also Published As

Publication number	Publication date
GB8716640D0 (en)	1987-08-19
CS508488A2 (en)	1990-08-14
DD281804A5 (de)	1990-08-22
CS274432B2 (en)	1991-04-11
ZA885103B (en)	1990-03-28

Publication	Publication Date	Title
EP0017332B1 (en)	1985-07-31	Pharmaceutical heterocyclic compounds, processes for their preparation and compositions containing them
EP0010951A1 (en)	1980-05-14	4-Hydroxy-2-pyrone derivatives, process for their preparation and their pharmaceutical preparations
EP0017195A1 (en)	1980-10-15	Derivatives of 2,5-disubstituted-cyclohexane-1,3-diones, process for preparation thereof and pharmaceutical composition containing them
EP0001534B1 (fr)	1981-08-12	Nouveaux dérivés du pyrrole, leur procédé de préparation et leurs applications en thérapeutique
NO136492B (cs)	1977-06-06
EP0239461A1 (fr)	1987-09-30	Dérivés de N-¬¬(hydroxy-2 phényl) (phényl) méthylène amino-2 éthyl acétamide, leur préparation et leur application en thérapeutique
EP0139584A2 (fr)	1985-05-02	Dérivés d'imidazoline, leur préparation et leur application en thérapeutique
EP0351255A2 (fr)	1990-01-17	Dérivés de [(pipéridinyl-4)méthyl]-2 tétrahydro-1,2,3,4 isoquinoléine, leur préparation et leur application en thérapeutique
SU910118A3 (ru)	1982-02-28	Способ получени N @ -глюкофуранозид-6-ил-N @ -нитрозомочевины
EP0006789A1 (fr)	1980-01-09	Composés bis (aryloxyalcanecarboxyliques), leur préparation et leur utilisation en thérapeutique
CH630623A5 (fr)	1982-06-30	Procede de preparation de derives de l'acide propionique.
HU211554A9 (en)	1995-12-28	Circulation-active dibenzo/1,5/dioxocin-5-ones
EP0074873A1 (fr)	1983-03-23	Dérivés de phénoxy-3 propanol-2, leur préparation et leur application en thérapeutique
US3994955A (en)	1976-11-30	Substituted phenoxydialkylacetic acids and esters
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
Baumgarten et al.	1960	Cinnolines. VII. The Neber-Bossel Synthesis1, 2
US4377704A (en)	1983-03-22	Hetero-prostaglandin derivatives and processes for preparing them
EP0091181B1 (en)	1986-12-17	Aroyl pyrrolizine compounds, process for their preparation and pharmaceutical compositions containing them
JPH02275846A (ja)	1990-11-09	カルボン酸誘導体
JPS606653A (ja)	1985-01-14	抗高コレステロ−ル血症活性を有する５−チアアルカン酸誘導体
Shriner et al.	1942	Synthesis of tectorigenin dimethyl ether
Johnson et al.	1950	The stobbe condensation with ethyl γ-anisoylbutyrate. A new route to some estrone intermediates
EP0080419B1 (fr)	1990-01-24	Haloalkyl-8-4H-(1)-benzopyran-4-ones, et procédés de préparation
Ganem et al.	1974	Improved methods for the side-chain degradation of lanosterol. Synthesis of 4, 4, 14. alpha.-trimethyl-5. alpha.-pregn-8-en-20-one derivatives
Chaykovsky et al.	1970	Transformation products of 2-(2-imidazolin-2-yl) benzophenone