CA1052271A - 1,2 - and 2,3 - epoxy alkanes - Google Patents

1,2 - and 2,3 - epoxy alkanes

Info

Publication number: CA1052271A
Authority: CA; Canada
Prior art keywords: composition; formula; epoxy; carbon atoms; epoxy alkanes
Prior art date: 1974-03-11
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.): Expired

Application number

CA221,651A

Other languages

English (en)

French (fr)

Inventor

Jacques Debat

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.)

Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA

Original Assignee

Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA

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.)

1974-03-11

Filing date

1975-03-10

Publication date

1979-04-10

1975-03-10 Application filed by Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA filed Critical Institut de Recherches Chimiques et Biologiques Appliquees SARL IRCEBA

1979-04-10 Application granted granted Critical

1979-04-10 Publication of CA1052271A publication Critical patent/CA1052271A/en

Status Expired legal-status Critical Current

Links

239000004593 Epoxy Substances 0.000 title abstract description 16
150000001335 aliphatic alkanes Chemical class 0.000 title abstract description 16
150000001875 compounds Chemical class 0.000 claims abstract description 14
210000002307 prostate Anatomy 0.000 claims abstract description 13
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
229930195733 hydrocarbon Natural products 0.000 claims abstract description 9
230000003248 secreting effect Effects 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 16
239000003937 drug carrier Substances 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 abstract description 6
206010036940 Prostatic adenoma Diseases 0.000 abstract description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
238000000034 method Methods 0.000 description 16
210000000981 epithelium Anatomy 0.000 description 12
239000000047 product Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
230000000875 corresponding effect Effects 0.000 description 10
LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000003981 vehicle Substances 0.000 description 7
VHMBMZSDFOQAHR-HWKANZROSA-N (e)-icos-2-ene Chemical compound CCCCCCCCCCCCCCCCC\C=C\C VHMBMZSDFOQAHR-HWKANZROSA-N 0.000 description 6
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
239000007787 solid Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 5
150000004965 peroxy acids Chemical class 0.000 description 5
VGYBKPBFRIXAST-UHFFFAOYSA-N 2-heptadecyl-3-methyloxirane Chemical compound CCCCCCCCCCCCCCCCCC1OC1C VGYBKPBFRIXAST-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
150000001336 alkenes Chemical class 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
229940073584 methylene chloride Drugs 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
INJRDZMWIAYEMM-UHFFFAOYSA-N 9-Oxo-2-decenoic acid Natural products CC(=O)CCCCCC=CC(O)=O INJRDZMWIAYEMM-UHFFFAOYSA-N 0.000 description 2
INJRDZMWIAYEMM-SOFGYWHQSA-N 9-Oxo-2E-decenoic acid Chemical compound CC(=O)CCCCC\C=C\C(O)=O INJRDZMWIAYEMM-SOFGYWHQSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
-1 chloromethylene Chemical group 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
238000004821 distillation Methods 0.000 description 2
210000004907 gland Anatomy 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
RHEVFAMQJMWLFS-UHFFFAOYSA-N icosan-2-ol Chemical compound CCCCCCCCCCCCCCCCCCC(C)O RHEVFAMQJMWLFS-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
239000004006 olive oil Substances 0.000 description 2
235000008390 olive oil Nutrition 0.000 description 2
150000002924 oxiranes Chemical class 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
HFOFYNMWYRXIBP-MOPGFXCFSA-N 2-methyl-7S,8R-Epoxy-octadecane Chemical compound CCCCCCCCCC[C@H]1O[C@H]1CCCCC(C)C HFOFYNMWYRXIBP-MOPGFXCFSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
238000003747 Grignard reaction Methods 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
206010061926 Purulence Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000027326 copulation Effects 0.000 description 1
YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000010908 decantation Methods 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
229960004132 diethyl ether Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000036732 histological change Effects 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
206010020718 hyperplasia Diseases 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA221,651A 1974-03-11 1975-03-10 1,2 - and 2,3 - epoxy alkanes Expired CA1052271A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB1068374A GB1453392A (en)	1974-03-11	1974-03-11	Epoxides and their therapeutic application

Publications (1)

Publication Number	Publication Date
CA1052271A true CA1052271A (en)	1979-04-10

Family

ID=9972360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA221,651A Expired CA1052271A (en)	1974-03-11	1975-03-10	1,2 - and 2,3 - epoxy alkanes

Country Status (18)

Country	Link
JP (1)	JPS50135008A (de)
AR (1)	AR206223A1 (de)
AT (1)	AT342612B (de)
BE (1)	BE826488A (de)
CA (1)	CA1052271A (de)
CH (1)	CH594652A5 (de)
DE (2)	DE2559764C2 (de)
DK (1)	DK80375A (de)
ES (1)	ES435479A1 (de)
FI (1)	FI60001C (de)
FR (1)	FR2263761B1 (de)
GB (1)	GB1453392A (de)
IE (1)	IE40822B1 (de)
IL (1)	IL46785A (de)
NL (1)	NL7502845A (de)
NO (1)	NO144151C (de)
SE (1)	SE420724B (de)
ZA (1)	ZA751489B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3633655A (en) *	1970-09-23	1972-01-11	United States Steel Corp	Construction for connecting and aligning sections of a guide-roll rack
US4890714A (en) *	1986-02-14	1990-01-02	Brown H Gary	Conveying system

1974
- 1974-03-11 GB GB1068374A patent/GB1453392A/en not_active Expired
1975
- 1975-01-01 AR AR257927A patent/AR206223A1/es active
- 1975-02-28 DK DK80375*#A patent/DK80375A/da not_active Application Discontinuation
- 1975-03-05 DE DE2559764A patent/DE2559764C2/de not_active Expired
- 1975-03-05 FR FR7506913A patent/FR2263761B1/fr not_active Expired
- 1975-03-05 DE DE2509503A patent/DE2509503C3/de not_active Expired
- 1975-03-10 SE SE7502641A patent/SE420724B/xx unknown
- 1975-03-10 CA CA221,651A patent/CA1052271A/en not_active Expired
- 1975-03-10 ES ES435479A patent/ES435479A1/es not_active Expired
- 1975-03-10 BE BE154179A patent/BE826488A/xx not_active IP Right Cessation
- 1975-03-10 NO NO750785A patent/NO144151C/no unknown
- 1975-03-10 IL IL46785A patent/IL46785A/xx unknown
- 1975-03-11 AT AT185975A patent/AT342612B/de not_active IP Right Cessation
- 1975-03-11 IE IE525/75A patent/IE40822B1/xx unknown
- 1975-03-11 ZA ZA00751489A patent/ZA751489B/xx unknown
- 1975-03-11 JP JP50029975A patent/JPS50135008A/ja active Pending
- 1975-03-11 NL NL7502845A patent/NL7502845A/xx not_active Application Discontinuation
- 1975-03-11 FI FI750692A patent/FI60001C/fi not_active IP Right Cessation
- 1975-03-11 CH CH308675A patent/CH594652A5/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU7897575A (en)	1976-09-16
ES435479A1 (es)	1977-01-01
DE2559764C2 (de)	1983-05-05
ATA185975A (de)	1977-08-15
FI60001B (fi)	1981-07-31
AR206223A1 (es)	1976-07-07
FR2263761B1 (de)	1980-02-22
FI60001C (fi)	1981-11-10
NL7502845A (nl)	1975-09-15
IL46785A0 (en)	1975-05-22
NO144151B (no)	1981-03-23
BE826488A (fr)	1975-06-30
NO144151C (no)	1981-07-01
NO750785L (de)	1975-09-12
IL46785A (en)	1978-06-15
CH594652A5 (de)	1978-01-13
IE40822L (en)	1975-09-11
SE420724B (sv)	1981-10-26
FI750692A (de)	1975-09-12
GB1453392A (en)	1976-10-20
SE7502641L (sv)	1975-09-12
JPS50135008A (de)	1975-10-25
IE40822B1 (en)	1979-08-29
DE2509503A1 (de)	1975-09-18
ZA751489B (en)	1976-02-25
FR2263761A1 (de)	1975-10-10
DE2509503C3 (de)	1980-12-18
DK80375A (de)	1975-09-12
AT342612B (de)	1978-04-10
DE2509503B2 (de)	1980-04-24

Publication	Publication Date	Title
Van Duuren et al.	1967	Carcinogenicity of epoxides, lactones, and peroxy compounds. VI. Structure and carcinogenic activity
US4186211A (en)	1980-01-29	Higher alkanol compositions and the use thereof in treatment of prostate disorders
EP0036663A1 (de)	1981-09-30	Oxiranbuttersäure-Derivate, ihre Herstellung und Verwendung, sowie diese enthaltende Arzneimittel
EP0019377A1 (de)	1980-11-26	1-Hydrocarbyloxyphenyl-1.2-diphenylalken-Derivate, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzung
US4046914A (en)	1977-09-06	Therapeutically active substituted saturated and mono-and polyunsaturated alkyl-glycerylethers
EP0339549A3 (de)	1991-01-16	Tyr-Peptid-Analoge
CA1052271A (en)	1979-04-10	1,2 - and 2,3 - epoxy alkanes
FR2409259A1 (fr)	1979-06-15	Peptides, sels d'addition acide de ceux-ci et procede pour leur preparation
FR2518091A1 (fr)	1983-06-17	23-dehydro-25-hydroxyvitamine d3, son procede de preparation et composition pharmaceutique la renfermant
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