IL38321A - Lactones of 1'-alkyl-2,2'-alkylenedioxy-5'-hydroxy-4'-cyclopentenyl propionic acid - Google Patents

Lactones of 1'-alkyl-2,2'-alkylenedioxy-5'-hydroxy-4'-cyclopentenyl propionic acid

Info

Publication number: IL38321A
Authority: IL; Israel
Prior art keywords: acid; formula; optically active; noted; meanings
Prior art date: 1966-08-25

Application number

IL38321A

Other languages

English (en)

Original Assignee

Roussel Uclaf

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.)

1966-08-25

Filing date

1967-08-22

Publication date

1972-05-30

1967-08-22 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1972-05-30 Publication of IL38321A publication Critical patent/IL38321A/en

Links

150000002596 lactones Chemical class 0.000 title claims description 16
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title claims description 7
235000019260 propionic acid Nutrition 0.000 title description 3
239000002253 acid Substances 0.000 claims description 37
238000000034 method Methods 0.000 claims description 19
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
-1 vinyl compound Chemical class 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 7
KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 claims description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 5
239000002585 base Substances 0.000 claims description 5
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 5
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
UPZFLZYXYGBAPL-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-dioxolane Chemical compound CCC1(C)OCCO1 UPZFLZYXYGBAPL-UHFFFAOYSA-N 0.000 claims description 3
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 4
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 claims 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims 2
150000008065 acid anhydrides Chemical class 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 2
150000000185 1,3-diols Chemical class 0.000 claims 1
235000001258 Cinchona calisaya Nutrition 0.000 claims 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 claims 1
BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 claims 1
150000004862 dioxolanes Chemical class 0.000 claims 1
229960002179 ephedrine Drugs 0.000 claims 1
229940095574 propionic acid Drugs 0.000 claims 1
229960000948 quinine Drugs 0.000 claims 1
239000001632 sodium acetate Substances 0.000 claims 1
235000017281 sodium acetate Nutrition 0.000 claims 1
150000003512 tertiary amines Chemical class 0.000 claims 1
BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 claims 1
229960000317 yohimbine Drugs 0.000 claims 1
AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 28
239000007864 aqueous solution Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 19
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 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
229910052708 sodium Inorganic materials 0.000 description 17
239000011734 sodium Substances 0.000 description 17
239000000243 solution Substances 0.000 description 15
238000002360 preparation method Methods 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
150000003839 salts Chemical class 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
239000011591 potassium Substances 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
238000010992 reflux Methods 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000002955 isolation Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000013019 agitation Methods 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
238000002983 circular dichroism Methods 0.000 description 3
238000005907 ketalization reaction Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
150000003431 steroids Chemical class 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
229940093476 ethylene glycol Drugs 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
WEBRDDDJKLAXTO-UHFFFAOYSA-N 2-ethyl-1,3-dioxolane Chemical compound CCC1OCCO1 WEBRDDDJKLAXTO-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL38321A 1966-08-25 1967-08-22 Lactones of 1'-alkyl-2,2'-alkylenedioxy-5'-hydroxy-4'-cyclopentenyl propionic acid IL38321A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
FR74179A FR1496817A (fr)	1966-08-25	1966-08-25	Synthèse de stéroïdes et produits intermédiaires ainsi obtenus
FR85043A FR91250E (fr)	1966-08-25	1966-11-25	Synthèse de stéroïdes et produits intermédiaires ainsi obtenus
FR113579A FR93372E (fr)	1966-08-25	1967-07-07	Synthese de stéroides et produits intermédiaires ainsi obtenus.

Publications (1)

Publication Number	Publication Date
IL38321A true IL38321A (en)	1972-05-30

Family

ID=27243517

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
IL38321A IL38321A (en)	1966-08-25	1967-08-22	Lactones of 1'-alkyl-2,2'-alkylenedioxy-5'-hydroxy-4'-cyclopentenyl propionic acid
IL28543A IL28543A (en)	1966-08-25	1967-08-22	Process for the preparation of optically active 13-alkyl gonapentaenes and intermediates
IL38321A IL38321A0 (en)	1966-08-25	1971-12-08	Novel lactones and their preparation

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
IL28543A IL28543A (en)	1966-08-25	1967-08-22	Process for the preparation of optically active 13-alkyl gonapentaenes and intermediates
IL38321A IL38321A0 (en)	1966-08-25	1971-12-08	Novel lactones and their preparation

Country Status (8)

Country	Link
US (4)	US3506693A (da)
CH (1)	CH485686A (da)
DE (1)	DE1793679C3 (da)
DK (1)	DK119005B (da)
FR (3)	FR1496817A (da)
GB (3)	GB1204922A (da)
IL (3)	IL38321A (da)
NL (1)	NL6711750A (da)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3855247A (en) *	1967-12-04	1974-12-17	Syntex Corp	Production of unsaturated carbocyclic ketones
US3954811A (en) *	1969-09-09	1976-05-04	Sumitomo Chemical Co., Ltd.	Production of cyclopentane derivatives
US3925419A (en) *	1970-06-22	1975-12-09	Merck & Co Inc	5-Cyclic ethylene acetals of 5-oxocyclopentane heptanoic acids and esters
US3898264A (en) *	1970-08-26	1975-08-05	Hoffmann La Roche	Steroid total synthesis process utilizing a cyanoalkyl A-ring precursor
US3975442A (en) *	1970-12-09	1976-08-17	Hoffmann-La Roche Inc.	2-Alkyl-2-(3-oxoalkyl)-1,3-cyclopentadiones
FR2181490A1 (en) *	1972-04-26	1973-12-07	Roussel Uclaf	Alkyl-2,6-dioxo-1-cyclohexyl propionate ketals - inters for steroids
US3897459A (en) *	1972-09-20	1975-07-29	Merck & Co Inc	5-Oxo-1{62 -cyclopentane heptanoic acid derivative
US4012420A (en) *	1972-10-25	1977-03-15	Schering Aktiengesellschaft	9,10-Secoestrane derivatives and their production
US3998847A (en) *	1972-10-25	1976-12-21	Schering Aktiengesellschaft	9,10-secoestrane derivatives and their production
US4001302A (en) *	1972-10-25	1977-01-04	Schering Aktiengesellschaft	9,10-secoestrane derivatives and their production
US4064173A (en) *	1973-12-21	1977-12-20	Hoffmann-La Roche, Inc.	9,10-Seco-steroids
US4495103A (en) *	1982-07-30	1985-01-22	Sumitomo Chemical Company, Ltd.	Preparation of optically active 4-demethoxydaunomycinone

1966
- 1966-08-25 FR FR74179A patent/FR1496817A/fr not_active Expired
- 1966-11-25 FR FR85043A patent/FR91250E/fr not_active Expired
1967
- 1967-07-07 FR FR113579A patent/FR93372E/fr not_active Expired
- 1967-08-02 CH CH1094567A patent/CH485686A/fr not_active IP Right Cessation
- 1967-08-21 US US661786A patent/US3506693A/en not_active Expired - Lifetime
- 1967-08-22 DK DK423167AA patent/DK119005B/da unknown
- 1967-08-22 IL IL38321A patent/IL38321A/en unknown
- 1967-08-22 IL IL28543A patent/IL28543A/en unknown
- 1967-08-22 DE DE1793679A patent/DE1793679C3/de not_active Expired
- 1967-08-23 GB GB8258/70A patent/GB1204922A/en not_active Expired
- 1967-08-23 GB GB8259/70A patent/GB1204923A/en not_active Expired
- 1967-08-23 GB GB38828/67A patent/GB1204921A/en not_active Expired
- 1967-08-25 NL NL6711750A patent/NL6711750A/xx unknown
1970
- 1970-01-21 US US8119A patent/US3637754A/en not_active Expired - Lifetime
- 1970-01-21 US US8120A patent/US3637755A/en not_active Expired - Lifetime
- 1970-02-06 US US13217A patent/US3637756A/en not_active Expired - Lifetime
1971
- 1971-12-08 IL IL38321A patent/IL38321A0/xx unknown

Also Published As

Publication number	Publication date
DK119005B (da)	1970-11-02
US3637755A (en)	1972-01-25
DE1668602A1 (de)	1972-04-13
FR1496817A (fr)	1967-10-06
IL28543A (en)	1972-07-26
FR93372E (fr)	1969-03-21
GB1204921A (en)	1970-09-09
DE1793679C3 (de)	1981-07-30
CH485686A (fr)	1970-02-15
DE1793679B2 (de)	1980-08-07
FR91250E (fr)	1968-05-03
DE1793679A1 (de)	1972-03-09
US3637756A (en)	1972-01-25
IL38321A0 (en)	1972-02-29
GB1204922A (en)	1970-09-09
GB1204923A (en)	1970-09-09
NL6711750A (da)	1968-02-26
US3506693A (en)	1970-04-14
US3637754A (en)	1972-01-25

Publication	Publication Date	Title
IL38321A (en)	1972-05-30	Lactones of 1'-alkyl-2,2'-alkylenedioxy-5'-hydroxy-4'-cyclopentenyl propionic acid
JPS60228441A (ja)	1985-11-13	光学的に活性なα―アリルアルカノイック酸の製造方法
JPH0333704B2 (da)	1991-05-20
US4673761A (en)	1987-06-16	Process for preparing anti-inflammatory cycloalkylidenemethylphenylacetic acid derivatives
US3953490A (en)	1976-04-27	Preparation of (3-trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile
JPS61218580A (ja)	1986-09-29	２−（２−アミノ−４−チアゾリル）−２−メトキシイミノ酢酸誘導体及びその製造法
JPS6341909B2 (da)	1988-08-19
US3590077A (en)	1971-06-29	Salts of chrysanthemic acid with 1-p-nitrophenyl - 2-n,n - dimethyl-aminopropane-1,3-diols
US2340268A (en)	1944-01-25	Esters of nitrohydroxy compounds
US2836616A (en)	1958-05-27	1-formyl-1-(3-keto-6-carboalkoxy-hexyl)-2-keto-10-methyl-1, 2, 5, 8, 9, 10-hexahydronaphthalene
US3578705A (en)	1971-05-11	Process for the preparation of homophthalic acid
FR2617484A1 (fr)	1989-01-06	Procede de preparation de l'acide (pyridyl-3)-3 1h-3h-pyrrolo (1,2-c) thiazolecarboxylique-7 dextrogyre
JPH0119371B2 (da)	1989-04-11
US3101354A (en)	1963-08-20	Process for the preparation of 19-nortestosterone and compounds used in this process
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